A guide to remote working for startups

When I co-founded my company in 2009, I had no choice about whether I was going to be running a remote, distributed business.

I was living in student accommodation, halfway through my second year at university. Money was limited so I built the initial product with one of my friends, bootstrapping the company from savings and then customer revenue. We couldn’t afford an office, and were happy working from home anyway – much easier to get to lectures on time!

Over the following 9 years, we grew the company on a remote-first, distributed model. All our engineers worked remotely and we only opened a physical office after 3 years so that we could bring the London team together. Later this evolved to deliberately building the commercial team in the office, but still operating using a distributed model for engineering.

At the time (2009), there were very few companies doing the same thing. Remote work was weird and rare. Most people commuted to an office.

That is still the majority of cases, but there are now companies operating at significant scale in a mostly or entirely remote, distributed way.

It is becoming clearer that office-based jobs can be done more effectively from home. It doesn’t work for everyone and remote working is not a magical cure to all the problems of an office. Indeed, remote working has its own challenges but it is becoming more desirable with clear benefits to both the employee and employer.

I fell into this mode of working through necessity, figuring out what to do through trial and error. This post is about how that worked and the lessons learned scaling to 20+ people globally.

Does working remotely work?

Yes, there are many of examples of successful companies operating on a remote, distributed model. It is not an unusual way to work.

The number of remote workers in the US grew by 79% between 2005 and 2012. The US Government issues annual reports on its approach to teleworking. For fiscal year 2017, they report:

improved attainment of goals in almost every area: improved employee attitudes; emergency preparedness; recruitment; retention; reduced employee commute miles; improved employee performance; and reduced real estate costs

2018 Telework Report to Congress

Cost savings were also tracked:

Over a quarter of Federal agencies were able to track some form of cost savings due to telework (29 percent). Those agencies increasingly reported cost savings achieved through telework, especially in the areas of transit/commuting, rent/office space, and reduced employee absences.

2018 Telework Report to Congress

Similar effects have been studied in private companies, too:

Nicholas Bloom and graduate student James Liang, who is also a cofounder of the Chinese travel website Ctrip, gave the staff at Ctrip’s call center the opportunity to volunteer to work from home for nine months. Half the volunteers were allowed to telecommute; the rest remained in the office as a control group. Survey responses and performance data collected at the conclusion of the study revealed that, in comparison with the employees who came into the office, the at-home workers were not only happier and less likely to quit but also more productive.

To Raise Productivity, Let More Employees Work from Home

The evidence is there to show that remote working has tangible benefits. The list of companies implementing this at scale is impressive.

Examples of remote, distributed companies

One of the big challenges I faced growing my company was there were very few businesses that were operating remote-first. Emphasis on “first”. There are thousands of distributed companies – any business that has more than 1 office has to deal with employees in different locations. However, whilst they might use many of the tools you will find in a remote-first company, they still apply office-based thinking to solving problems.

Today, we not only have startups adopting a remote-first model, there are companies at large scale doing this successfully.

Examples of remote, distributed companies: Automattic, GitLab, InVision, Zapier, Buffer and Basecamp

Automattic, the business behind WordPress, Jetpack and many other projects, has been doing this for over 15 years. They are now approaching 900 people.

Much like WordPress sought to change the way we publish on the web, Automattic has set out to change the way we work. We are an entirely distributed company — with more than 800 employees working from more than 62 countries, and no physical headquarters. We are a company that works on, and for, the web.

About Matt Mullenweg

Another company doing this at scale is GitLab. They have over 650 people working from 50 different countries, all-remote. To make this work, they have also adopted a culture of transparency both internally and externally. This has proven extremely helpful for sharing how they manage the company and setting them up to be a shining example of how to run a remote business.

At GitLab, everything is documented in a 2000+ page public handbook. From their all-remote manifesto to how they manage hiring and how their customer success team operate is covered. Writing is key to success for all businesses and GitLab go one step further by sharing this so others can see what might work for them.

Remote working has an influence on how your own products develop. Automattic developed the P2 theme which is what they use internally for communication. InVision have over 1,000 people working for them remotely, and this has influenced features in their own products.

For the team behind InVision Studio, working remotely has helped them do more than just communicate and collaborate better—it’s allowed them to spot gaps in their own workflow and then apply those solutions to Studio as they build it. What better way to know whether your platform’s features are intuitive, accessible, powerful, or complete unless you were thrust into the exact scenario in which they’d be most needed?

Building InVision Studio with a fully remote team

On the smaller side but still quite big (and growing), Zapier has over 100 people all working remotely. Another tech startup offering a technical product, Zapier have written extensively about how their company works and how to succeed in a remote, distributed model.

It’s not just companies selling to engineers or those in the same industry. Buffer is 80+ people, all remote. And Basecamp, one of the original remote-first companies who’s founders wrote Remote all about distributed work, are currently at around 50 people.

So is the remote, distributed model the future of work? Matt Mullenweg of Automattic certainly thinks so:

Core principles for a remote, distributed company

The tools used to run a remote, distributed company are relevant but you have to apply some core principles first. A degree of process is necessary in any company but is particularly important where remote work is concerned.

Many companies focus too much on technology and not enough on process. This is akin to trying to fix a sports team’s performance by buying better equipment. These adjustments alone might result in minor improvements, but real change requires a return to fundamentals.

Why Remote Work Thrives in Some Companies and Fails in Others


Communication is the hardest part of running any company. It is important for everyone to have a clear sense of the company mission and values, how things are going and what their impact should be.

This is harder in remote-first companies because it requires more effort than simply talking to someone sitting next to you.

That said, many of the strategies for addressing this will significantly improve the working environment and culture of any company, remote-first or not. I’ve written about this is much more detail so won’t cover it here:

Establishing a regular communication and reporting cadence is a standard part of running a public company – financials and progress get announced in an expected format on an expected timeline. If public companies can do this on a quarterly basis, there’s no reason why smaller companies can’t do it too, and likely much more regularly.

Communication inside startups – what and how


There are industries where trust is not necessary. Those are often environments where the job is based on rapid, repeat assembly work. Factories or perhaps certain types of manual labour. In these roles, employees are tracked so closely to try to engineer trust out of the equation.

That said I’d still argue that regardless of the job, you want to hire people you can trust otherwise you end up depersonalising the role. That’s not a good working environment.

The context of this article is knowledge-work such as technology, engineering, science, research, i.e. roles that could be office-based.

If you can’t trust your people to do what they should be doing without you standing over their shoulder, you’ve hired the wrong people. That’s not a process problem, it’s a people problem. 

I Swear I’m Wearing Pants: 5 Misconceptions About Remote Employment

The worst kind of work is where you are simply following orders.

Sometimes issuing specific tasks is necessary e.g. preparing a spreadsheet of KPIs or fixing a reported bug. However, most knowledge-work is best driven by outcomes, leaving the individual to decide how to achieve it (guided by the company mission and values).

Managers should not be defining “how” and need to take deliberate steps to avoid being controlling.

Very few knowledge workers bill by time increment. Engineers, programmers and academics are usually paid fixed salaries.

Lawyers are a good counter-example. Some projects can be scoped to a fixed budget but legal questions often require research which can’t be time estimated. Such things require reading, writing, editing and conference calls plus discussion with colleagues. You are paying for their ability to locate and synthesise information so as to form a technical, legal opinion.

Another example might be software engineering. There are many freelancers who will charge based on number of hours. Whether this is the correct way to charge for development is debatable. The best consultants work with customers on the basis of the value they deliver, not the amount of time spent.

The main thing holding my rate down for the early years was personal discomfort with being “worth” the types of rates which I desired to charge. I dealt with (deal with?) impostor syndrome frequently and had little context for what alchemy one needs to work to justify professional rates.

Spoiler alert: there is virtually no difference in the mechanics of work done between $100 an hour, $200 an hour, and $30k a week — all of the leveling up there is in sophistication on who you go after, what engagements you propose and deliver, and how you package things for clients.

By the end of my consulting career, I pointed to a small pile of mostly satisfied customers and other evidence that I could do the work, sketched out a “Here’s how I plan to create a couple million dollars of value for your company” in proposals, and then just announced my rate. I received rather less pushback than I expected and virtually never negotiated on rate, using a trick from Thomas Ptacek (“If a client says you’re out of the budget, start talking about the scope of the engagement to find something they can afford rather than slipping your rate.”)

Talking About Money

Understanding whether someone is performing in a salaried role is more complicated than correlating minutes tracked, lines of code written, emails sent, bugs fixed, tickets replied to, or whatever arbitrary and irrelevant metric your manager might be able to come up with.

This is ultimately about working to outcomes and not micromanaging your team.

Being deliberate

Linked to communication, this means taking extra effort to ensure everyone is in sync. Symptoms of not doing this properly include:

  • Information disseminated by rumour.
  • Inaccuracies and mixed messages leading to confusion.
  • Incorrect understanding of roles, goals, methods of working and deliverables.
  • Not knowing how the company is performing.
  • Misunderstanding what everyone is working on and how you should be contributing.
  • Inability for teams to “do the right thing” and needing to wait for specific directions and task assignments.

The most common approach to address this is to write everything down, share everything, record/transcribe meetings, be as transparent as possible and not rely on informal methods of communication.

An engineering driven approach is to think about how to set up an organisational commit log.

This is where tools start to come in and becomes crucial for scaling past a couple of people. Do you use Slack as the primary communication method? Or email? What goes into a Google Doc vs a text file in a code repo? These are all important decisions but what you do and how you do it don’t really matter. It’s making a decision that counts. Everything should have exactly one “correct place” and everyone should know where that is.

Without formally documenting how the company operates, you end up with multiple channels and information all over the place. Sharepoint, Google Docs, Slack, Confluence, email, [other random tool used by just one team].

GitLab’s handbook offers a great example of how to they this. You could adopt the same approach or create your own. The point is to just make a decision, then document it.

How do you motivate a remote team?

There are 3 key elements to motivating remote, distributed teams:

  • Meaningful work: This is one of the main advantages of smaller startups – each person is a significant part of the company and has a large impact on overall success. As the organisation grows, roles necessarily become more specialised and the meaning of the work changes. In startups, you work on a large part of something used by a small number of people. In large corporates, you work on a small part of something used by a large number of people. This is leverage. Otherwise, it can be challenging to see what impact your work has. Bored people quit.
  • Care about your people: It might sound obvious but so many companies clearly do not care about their people. This can still be a competitive advantage in how your company culture, values and approach to management bring out the best in everyone. This isn’t about providing free lunch, unlimited holiday (which actually doesn’t work) or book allowances, it comes down to the fundamentals of managing humans. Do you feel like your manager cares about you as a person? Are they regularly making time to talk about not just work-related topics? Do you trust them and feel like they have your back? Companies are not families but they are quite close it it. The relationship is always going to be professional but it is in the interests of the company not just to care about revenue and profit because it is actually the people delivering those numbers. People don’t quit bosses, they quit jobs, but who is responsible for what the job is like? The boss.
  • Communicate regularly: This is a running theme of the post so I won’t add any more here other than continuing to highlight how important it is.

Notice how these are not unique to remote, distributed companies? You can apply them to any company. It is only the implementation that is different in a remote company.

Challenges of remote, distributed working

Personal connections

The most crucial lesson I learned was about how important it was to get to know the team in-person, and for the team to get to know each other.

Whenever we hired someone new at Server Density, I could separate their time with the company into two phases: before they met everyone, and after. Although new hires usually got on with everyone fine via chat and video calls, there was a noticeable difference in their engagement once they had met the whole company.

Early in the life of my company, full meetups were more ad-hoc and less frequent. But by the time of the acquisition we were trying to get the whole company to meet every quarter.

…even the best video chat experiences can’t quite match the fidelity of a face-to-face conversation in a physical space. There is so much nuance and context to human communication that is lost, especially when conversing in groups. It’s why distributed companies (like mine, Automattic) still have in-person team meetups and all-company gatherings — technology simply can’t replace the human connection of being together. 

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There are many ways to organise these meetups, from flying the whole company away for exotic retreats to just a few days all working together in one place. What matters isn’t so much the format but getting everyone together to work, socialise and get to know each other.

We try to get together every 9 months or so to get face-time with one another, build community, and get some work done! Since our team is scattered all over the globe, we try to plan a different location for each GitLab Contribute.

Contribute is not a mandatory trip or a department offsite, nor is it a vacation or incentive trip. It’s a chance for everyone to meet fellow GitLab team-members across all departments and regions: part team building, part education, part customer interaction, and hopefully all fun.

GitLab Contribute

This can be expensive, especially as the company grows, but is definitely worth the cost for the improvements to team morale and productivity in the long run.

Remote, distributed working is not a method of cost-saving. Money not spent on an office will instead be spent on travel expenses.

Buffer wrote about how they handle their meetups and also recorded a more recent podcast that goes into detail about how it all works.

Working on a single mission

Sometimes it’s necessary to bring everyone together for a sprint towards a single goal. Such occasions should be rare but where that shared sense or purpose is really necessary, it is beneficial to all be in the same physical location.

If I was starting a new company, I would include significantly more time working together from the same location. Critical times call for working in-person.The formation of a new startup is one of those times.

This is one of the arguments behind a tweet by investor, Arianna Simpson:

In a followup podcast she elaborated on the specific scenarios where she thinks it does make sense for everyone to be in the same location.

One thing I’ve noticed about startups that end up being very successful is often there is this strong sense of shared mission and shared energy, and that I find very difficult to replicate if you have people in different locations because you don’t have the same sense of camaraderie, the same sense of “You know what, this sucks but we’re gonna stay here until 10 PM and pound it out until we’re done ’cause we’ve gotta get this release out,” or whatever it is. So that is a really difficult intangible that’s hard to replicate if you have people in different time zones or different locations. It’s hard to muster up the same level of enthusiasm.

Is remote work ‘bull***t?’

Starting a new project is a similar situation where you might want to have the team together for the kick-off, planning, design and initial implementation.

The end of a project can also be a good time to have everyone together. Celebrating the launch and completion of a major project in person can have a major, positive impact on morale.

Remote, distributed-first does not mean exclusively remote, distributed-only.


You’ll note that communication is a common theme when thinking about remote, distributed teams. This is because it is so difficult to get right.

If the problem of working in an office is the constant interruptions, then the problem of remote working is the default to using real time chat. Slack is the most common example, but it applies to any kind of instant messaging.

I’ve written in detail about the challenges of communication in general and also about chat:

I personally dislike Slack (and any real-time chat) for anything other than general, social chat or deliberate collaboration on an ongoing project e.g. triaging a customer issue with a group of people in real time, doing incident response, or backchannel chat between participants during a sales meeting. These are all instances where a small number of people come together for a specific task and for a specific period of time, after which they disband. Real time chat is an awful tool for anything else because it implies everyone must be available and responsive immediately, at all times. Information is too easily lost.

Communication inside startups – what and how

My favourite article on the challenges of chat is “Is group chat making you sweat?“. Email is my preferred method of communication because of how flexible it is – I can choose my client, layout, set up filters and decide when to check it. It’s not perfect but it really does beat instant messaging:

So what about IMs? In short… they combine the worst of both worlds while having the strength of none of them.

In theory, IMs are supposed to be fast (“instant”), but in practice typing takes enough time, to make instant messages much slower than simply talking. Ironically, the expectation of a fast response forces everyone to write short and rather poorly structured short phrases that are hard to understand, especially out of the context of current circumstances.

In theory, IM communication is persistent, but in practice because of lack of structure, intertwined topics, and insufficient metadata, what have been persisted is mostly useless. Searching through the history of a Slack room is difficult, and rarely useful.

Kill Instant Messaging

That said, we have gone through a similar transition in the past – from no email to email – and similar problems arose. Email is certainly not universally loved.

In a 2011 study published in the journal Organization Science, researchers noted that while email was widely regarded as a “growing source of stress in people’s lives,” research also suggests that it affords people “flexibility and control by enabling them to communicate from anywhere at any time.” To attempt to address this contradiction, the researchers drew on interviews from nearly a decade earlier, conducted when email itself was still ripping through American offices, and producing its own stories of relief, ambivalence, and horror. Employees’ worries will sound familiar, and in hindsight maybe not unwarranted. “Although, in theory, email’s asynchrony should have granted recipients the leeway to respond at a time that was convenient for them,” the study said, “our informants described strong cultural expectations about not keeping senders waiting.” 

Slack Wants to Replace Email. Is That What We Want?

As with any workplace culture, it is important for management to set the example of what is acceptable.

Stephen R. Barley, a professor of technology management at the University of California Santa Barbara and a co-author of the paper, remembers subjects lamenting, nearly 20 years ago, the erosion of work boundaries as symbolized and enacted by email. “I think what they’re really expressing, and most white-collar workers would never say this, is that these technologies are appropriating time at the beginning and end of days, without any kind of payment,” he said in a phone interview. “It’s an encroachment of work into other spaces in your life.” 

But with Slack, there is no perfect equivalent to inbox zero; an instant message from your boss during the day might demand not just a quick response, but an instant one; it will be up to us, but mainly our bosses, to establish what a late-night Slack message means or demands, as compared to an email, and what noise or vibration it should cause in the phone that many of us have moved closer to our beds.

Slack Wants to Replace Email. Is That What We Want?

Chat is here to stay and so this means developing a simple set of rules for where communication should take place. One approach is to delete messages after a short period of time. This makes it clear that chat is ephemeral. How often do you actually search chat logs and find something useful?

Density of expertise

Despite the major advantage of remote, distributed work being that you can hire the best people anywhere in the world, expertise still clusters in specific locations.

My conclusion is that whilst you can quite easily build out product, engineering and customer support teams within Europe and the UK, it is very difficult to do the same with early stage commercial teams. There’s the occasional highly talented individual who has done it before in the UK, but otherwise it’s almost impossible to recruit for commercial roles here. The initial sales, marketing and customer success hires need to be in the US.

Challenges of running an enterprise SaaS business in the UK

Whilst you can build these teams remotely, it may place you at a disadvantage against competition who can leverage the benefits of a specific location.

If you are building a high-growth, venture funded startup in a very competitive industry, this will matter at very specific stages of the company lifecycle. It matters who the initial founding team are. It matters when you start to build out that first commercial team. And it matters again when the company goes into scale mode, leading into an IPO.

So why are industry towns so powerful?
1. Talent base. Great engineers, sales people, product people, etc. exist all over the world. However, the highest concentration of outstanding ones are concentrated in industry towns (just as the highest concentration of great actors in the USA live in Los Angeles). Similarly, the people who know how to scale technology companies are concentrated in the tech epicenters in the graphs above. Many companies come to the SF Bay Area to fundraise post product-market fit to access this talent base and know-how.

Industry Towns – Where You Start A Company Matters

Outside of those critical turning points, and for businesses that are operating on a different growth model, then this matters less.

It will be interesting to see how GitLab progress towards their Nov 2020 IPO date but despite being an amazing example of how to run a remote, distributed company, it is interesting that the CEO is based in San Francisco.

Tips and tricks for remote, distributed teams

At Server Density, we developed a number of mechanisms to help run the remote, distributed team. These evolved over time from 2009 to the acquisition of the company in 2018.

Weekly roundup

This started as a weekly standup for the whole company to report on what they had been doing that week but it eventually changed primarily to be a social discussion.

Meetings are a necessary part of working with multiple people but using them to distribute status updates is very inefficient and expensive. Status updates can be provided in writing, asynchronously. Meetings are for discussion and debate. But when you have a team all working remotely, regularly getting together to “see” each other also has a social benefit.

It was also the only compulsory meeting during the week. Unless you were on holiday, you had to be in this call.

At one point, we stopped the meetings for a few months and experimented with just using written updates. We quickly had requests to bring back the meetings so we could talk to each other!

The format we ended with was as follows:

  1. CEO Update (~5 minutes): Any announcements or important news as well as a quick update on the key business metrics, with a more detailed writeup shared later. I also highlighted one or two things I’d seen during the week that particularly stood out – deals closed, great responses to support issues, tricky bugs fixed, etc. The important thing was to mention one or two people and some specific piece of work I thought deserved everyone knowing about.
  2. Team updates (~1 minute each): Every person would say something they found interesting during the week. Updates could include work as well as something they had read or watched. We used a random order generator to mix up the order of speakers every week. After each person had finished speaking, there was an opportunity to ask questions. This often prompted some good discussions.
  3. Anything else: An opportunity for anyone to mention something not already discussed.

With 20 people we were usually able to complete this meeting within 30 minutes. It breaks some of the rules for meetings e.g. no status updates but we were deliberate in what the format was about – hearing from your colleagues about what they had been doing.

This worked nicely for us but I’m not sure how far this would scale. Even being strict about times, people tend to go over their 1 minute. The format we used above worked for us at 20 people but is quite different from what we used at 5 and 10 people. GitLab have blogged about how they changed their weekly 40-person meeting into a 10-15 minute podcast.

Random calls with team members

Working with people in an office usually means some socialising outside of work hours where you get to know your colleagues personally. This is more difficult for remote, distributed work because “out of hours” should mean disconnecting completely!

Every week, everyone was paired up for a 30 min call with someone random from the company. There was no particular agenda so they could discuss what they liked. Even on a small team, this helped connect team members who might rarely (or never) talk to each other.

This scales well even with large companies because as the team grows, you become more siloed in who you interact with on a daily basis.

What have you been working on?

Knowing what your colleagues are doing is one of the challenges of communication made more difficult by remote, distributed working. One fix we tried was a regular prompt for people to answer the question: “what have you been working on [today | this week | recently]?”

We used Basecamp to automatically ask this every day (and also tried it more infrequently e.g. a couple of times per week). It was never compulsory and different people wrote at different frequencies to suit them, and when they had done something worth broadcasting to the whole company. There are Slack bots available to do this too.

The important thing was that it was voluntary and non-specific. Anyone could write whatever they liked. Tracking of bugs, epics, tasks, stories and other precise units of work is for other tools.

This worked for a time but usage declined over time to the point where not enough people were using it to make it worth continuing. It was replaced by the weekly roundup (see above).

However, one thing we did find was that there was a weird political element to “likes” of posts. Feedback I received indicated that there was an almost addictive aspect of checking posts for likes, seeing who had liked them and whether your own post had more likes than others.

Not having to think about likes having ditched Facebook and Instagram is a nice side benefit I’ve noticed. It definitely influences your behaviour in negative ways. Basecamp discovered this themselves, replacing the feature with Boosts. A good move.

Final thoughts

There is no “one true way” of running a company that will automatically deliver total productivity in every situation. Whether you run entirely in an office, entirely remotely or a mixture of both, every organisation needs properly thought through processes.

Those processes will differ as the company grows. Smaller organisations need minimal overhead to remain agile and able to iterate quickly. Larger firms need to be able to coordinate multiple teams working on various projects. But no process at all is just as much a decision about working practices (probably in an environment of chaos) as writing a detailed handbook would be.

The challenge of remote working is that it needs a much more deliberate approach to running things. There are fewer organisations using remote, distributed working methods. Not as much shared knowledge exists. But that is changing.

Companies that do not allow remote and/or do not properly consider how to effectively incorporate remote working into the long-term are going to fall behind and fail to attract the talented people that are crucial to success. The form that takes will be different in every case so it is important to avoid “remote purism”. It is clear when things aren’t working but there are many ways to make it work well.

Should you encourage your team to write their own blog?

When I started my company, Server Density, the first thing that went public was a blog post. The majority of the posts were about our technical challenges, with only occasional product/company related articles. I wrote a post almost every single week and after 9 years built the readership to +100,000 monthly uniques and +25,000 email subscribers. All organically and without paid promotion.

Of course, this was my own company so my identity was linked to the business. There’s an argument to say you should put 100% of your effort into building the brand of your business, not your personal brand.

Perhaps this is true for founders, but is it applicable to non-founder team members, too?

Employees have very different incentives from founders. They might be aligned with the success of the venture (if they’re early) but really they are negotiating an exchange of time and expertise for compensation (cash, stock, etc). They can leave at any point and when it’s time to move on, they will need to pitch themselves to a new employer. Their tangible output might be owned by the company but what about lessons learned?

When hiring someone, their past experience is relevant. Skills and capabilities are the usual filters for any hiring process, but what about personal brand?

There are many great examples of high profile “internet people” who have built up a personal brand through writing. Some of those now work for well known organisations. Some run their own companies or consultancies. Some are investors and some even employ some of the others!

Being “internet famous” isn’t even that important, but writing about and sharing experiences is. Note how they all do this through their own website as well their job. It’s their own place on the internet independent of whatever they might be doing now.

There are plenty of high profile CEOs and founders who do not blog or write but there are just as many who do. The same applies to non-founder team members – writing about experiences and sharing stories is valuable, not just for the individual to get experience writing but for everyone to benefit.

It’s not reasonable for a company to expect to control 100% of employee output. Even founders aren’t really expected to do this. Very few run their business for life. Startups fail. They are acquired. Founders move on. You wouldn’t invest all of your money into a single project, so why do the same with your time? A healthy life balance means side projects, multiple investments, hobbies and other interests.

Indeed, there is tangible benefit to the company in actively encouraging team members to write, even on company time. Writing is a skill that needs to be developed. Doing so will have major benefits for communication internally. Not only that, gradually building a brand is valuable not just for the individual but benefits their employer too.

Everyone should have their own website with their own content. Tweeting is one outlet but the benefits compound from writing on a domain you control. Whether you are an employee or a founder, it should be encouraged. It’s not difficult to start.

Writing as a core company value

As communication is the hardest problem facing any organisation, writing well should be one of the core values for every company.

When I hired for engineers at my company, Server Density (now acquired by StackPath), the first part of the selection process was a writing exercise. We asked every candidate to spend no more than 1 hour researching the answer to a simple question such as “Compare and contrast MySQL and MongoDB”.

The purpose was not necessarily to test their technical skills but to assess their written communication. Errors with spelling or grammar meant immediate rejection but the ability to convey complex ideas was the main focus of the assessment.

Although anecdotal, I found there was a strong correlation between writing capability and engineering skill. Showing that you take the time to proof-read your work is a good indicator that you will put the same care into your day job. This is especially important for coding.

Chris Laffra on LinkedIn

I would now apply this to all roles, not just engineering. The ability to convey ideas accurately, precisely and in such a way that others can understand is a crucial skill.

Examples from successful companies

Some of the most successful companies follow this sentiment.

Amazon famously uses 6-page narratives in order to propose new ideas and read in silence at the beginning of each meeting. Not only does the exercise force everyone to consider the details, it also ensures a significant amount of time and effort goes into the idea in the first place.

We don’t do PowerPoint (or any other slide-oriented) presentations at Amazon. Instead, we write narratively structured six-page memos. We silently read one at the beginning of each meeting in a kind of “study hall.” Not surprisingly, the quality of these memos varies widely. Some have the clarity of angels singing. They are brilliant and thoughtful and set up the meeting for high-quality discussion…

…The great memos are written and re-written, shared with colleagues who are asked to improve the work, set aside for a couple of days, and then edited again with a fresh mind. They simply can’t be done in a day or two.

Amazon 1997 Letter to Shareholders

This results in Amazon consistently operating at a high level of efficiency:

Imagine for a moment that you could go into a meeting and everyone in the meeting would have very deep context on the topic you’re going to discuss.  They would be well-versed in the critical data for your business.  Imagine if everyone understood the core tenets you operate by and internalized how you’re applying them to your decisions.

How great would it be not to be constantly interrupted by clarifying questions?  How great would it be not to have the decisions in the meeting based on the social networking advocacy that happened before the meeting?  How great would it be if executives deeply understood your organization from your perspective before asserting they know better how to do it?  How great would it be to be able to review the core data going into a decision rather than have someone summarize it and assert that correlation is causality without revealing their work?

This is what meetings are like at Amazon and it is magical.

The Beauty of Amazon’s 6-Pager, Brad Porter

It’s not just Amazon. If you have ever used any Apple apps on iOS or macOS, you will have noticed how consistent they are in design and style. This is because they have strict, detailed Human Interface Guidelines for all their platforms.

Design consistency is an indicator of quality and the same applies to writing. Apple has a style guide which is just as relevant as the Interface Guidelines:

The Apple Style Guide provides editorial guidelines for text in Apple instructional materials, technical documentation, reference information, training programs, and user interfaces. The intent of these guidelines is to help maintain a consistent voice in Apple materials.

Writers, editors, and developers can use this document as a guide to writing style, usage, and Apple product terminology. Writers and editors should thoroughly review the guide to become familiar with the range of issues involved in creating high-quality, readable, and consistent materials. Apple developers and third-party developers should follow these guidelines for user-facing text.

It’s not just the large, successful companies that take this approach. It applies to smaller, successful businesses as well. Basecamp, a ~40 person company, uses a very similar written pitch to propose and discuss ideas for feature development:

Why don’t we pitch in person? For a few reasons:

1. We feel it’s better to write something up completely. This forces the floor — the person who’s making the pitch can’t be interrupted. They are guaranteed to be able to present their story completely, exactly as they want.

2. Further, we believe writing things out makes you consider them at a deeper level.

3. We’re big believers in asynchronous communication — write it down now and other people can absorb it later when they’re ready. Real-time communication in person or virtually forces synchronization of schedules which is highly inefficient.

4. And last, when it’s posted to Basecamp as a message, all feedback and follow up questions are automatically attached to the original post. This keeps all communication about the pitch centralized in one place on one page so everyone has access to the same story. One version of the truth.

Pitching an idea

Indeed, the importance of writing skills is something that Basecamp consider as part of their hiring process:

Our top hiring criteria — in addition to having the skills to do the job — is, are you a great writer? You have to be a great writer to work here, in every single position, because the majority of our communication is written, primarily because a lot of us work remotely but also because writing is quieter. And we like long-form writing where people really think through an idea and present it.

Jason Fried of Basecamp on the Importance of Writing Skills

Writing really is crucial to successful communication, and success in general. There are too many examples of poor writing. Why not make it one of your core values?

Parachuting tasks because available time is fixed

There are 24 hours in a day. 8 of those are the standard length of the working day, of which an even shorter total make up the time we can spend actually doing focused work.

The available time does not change. You might be able to develop a system to increase the number of focus hours but you cannot increase the number of available hours.

If you read that paragraph in isolation then it is an obvious fact. Of course you can’t increase the available hours.

So why is this ignored when we’re actually planning work and progressing through a task list?

An interrupt-driven culture whereby new tasks appear without reducing the pool of tasks the team are expect to complete is something I see on a regular basis across many companies.

This is especially prevalent in engineering teams. A sprint or development cycle will begin with a set number of tasks, and then mid-cycle new tasks will be dropped in due to critical bugs, customer complaints or other reasons. This doesn’t necessarily have to be an issue – it becomes a problem when those tasks are forced in without removing other tasks. The available time is the same but suddenly there are now more things to do.

The results of this include:

  • Deadlines being missed – the work still has to be done, it’s just there is now more of it than when the original time estimate was discussed. Without adjustment then it is inevitable that everything will now take more time.
  • Existing work taking longer than expected – if a critical bug comes in that needs to be dealt with immediately, that will cause a context switch that has an impact on individual or team productivity.
  • Multiple teams being impacted – the original work plan may have external dependencies from other teams e.g. a marketing campaign launch.
  • Requests for overtime – the team may be expected to work longer and later, despite this not actually correlating with productivity.

At my company, Server Density, we eventually implemented a solution to this we called “parachutes”.

  • Development cycles were a fixed length.
  • All the tasks to be completed were scoped in tickets each of a fixed length.
  • Every member of the team had a known level of productivity i.e. how many tasks they could complete in a cycle.
  • This gave us a total known capacity for the cycle, which allowed us to slot in the tickets that would be completed in the cycle.
  • We discussed which tickets needed to be done for each cycle, with stakeholders across the business sponsoring the tickets they prioritised, everyone debating the priorities.
  • As a result, each ticket had a priority relative to the other tickets in the cycle.
  • If an unexpected task came in, it was first triaged to scope and size it. Once agreed that it needed to be dealt with urgently, the lowest priority ticket in the current cycle was “kicked out” and this new ticket “parachuted” in to replace it.

This resulted in knowing what we were sacrificing to get the new ticket solved, with the stakeholders for the kicked-out ticket being involved in the discussion about whether to parachute it. The cycle remained a fixed length and meant that we had a good level of certainty about what was going to be completed and when.

Dropping a new task into an existing cycle always has a cost. If you don’t acknowledge that time is fixed then the cost ends up being hidden under overtime, surprise missed deadlines and frustration from supporting teams. It is better to explicitly incur that cost in a defined way by sacrificing some other known task than to keep it hidden behind a bad process.

Parachuting tasks is always frustrating, especially for the owners of the kicked out ticket. But the key is visibility and shared decision-making. Without this, teams continue to maintain a fiction that everything will still be completed on time with the same effort, until it isn’t. That’s significantly more frustrating.

Communication inside startups – what and how

Once you have more than 1 person in a company, I think communication is the biggest challenge. I don’t think it matters whether you’re working 100% remotely or have everyone in the same office, the challenge of communication remains similarly difficult.

The challenge and how to solve it changes depending on the size of the company but there are common questions that everyone should have a concise and precise answer for at all times:

  • What is the overall mission of the company? Why are we doing what we’re doing? How is the company tracking against that mission? What is going well and what isn’t?
  • What are the company values? How should we evaluate the ways of achieving our mission?
  • How do we work and collaborate together?
  • What is expected of me today, this week, this month and this year? How does that link to the overall mission? How am I tracking against those goals? What is going well and what isn’t?
  • What is the rest of the company doing?

Practicing complete transparency is the best way to smooth the flow of information to different people across the company, whether they are employees, executives, board members or investors.

There are very few classes of information which may not benefit from full sharing – disciplinary and HR matters, complaints and perhaps individual compensation packages (but having a consistent, open set of salary bands makes up for that).

So what do these different areas involve? What are the key things that need to be communicated?

What is the overall mission of the company?

Later in the life of a company it should be obvious what the product is, but it may be harder to explain the why: Why are we building this? Why have we built that feature? What is the big problem we are trying to solve over the next 10-20 years?

This is crucial to understand because every other aspect of the company flows from this single mission. Everyone needs to know the mission because otherwise they cannot understand why the work they are doing is important to achieving that mission.

The best mission statements are short but specific. Easy to remember and obvious, but hard to achieve and involve playing the long game.

One of my favourites is Tesla:

…the overarching purpose of Tesla Motors (and the reason I am funding the company) is to help expedite the move from a mine-and-burn hydrocarbon economy towards a solar electric economy, which I believe to be the primary, but not exclusive, sustainable solution.

Secret Tesla Motors Master Plan

And SpaceX:

The company was founded in 2002 to revolutionize space technology, with the ultimate goal of enabling people to live on other planets.

About SpaceX

These are both very clear about the problem and what the company is trying to do.

But the mission doesn’t need to be as big picture or ambitious as what Elon Musk is trying to achieve – it’s just as important to have a clear mission if your goal is to build a small but successfully sustainable company.

Without a clear, written statement, you cannot align the rest of the company goals, understand how to prioritise what to do next and will certainly find it difficult to hire and retain your team.

Even simple mission statements require constant communication. The whole company need to know not just what the company is working towards but how things are tracking against that goal. With real numbers and commentary on both positive and negative progress, the mission will be reinforced.

This means having regular reporting of KPIs to the whole company. You are probably doing this for investors and your board already so this format can be reused for the rest of the company.

Information about company performance either gets out through actively sharing the real numbers or it is distributed through rumour and gossip. There is no option where information doesn’t travel, so why would you not want to be in full control of the narrative and detail?

Doing this builds trust in good times so that you can call on the team when you enter more challenging times. With everyone aware of the same numbers, everyone has the same context for making decisions, understanding why decisions were made and making their contribution as valuable as possible.

What are the company values?

The company mission is always very high level – it describes “what” and “why” but doesn’t really discuss “how”.

I used to think that the idea of “company values” was a cliché but that is only true if they are vague and written in generic management speak. If the company values don’t prescribe specific behaviour then they aren’t particularly useful.

Netflix has perhaps the most famous description of its culture and values, from the culture deck CEO Reed Hastings published almost 10 years ago:

More recently, these have been written out as a set of high level principles which they then break down into specific values.

Like all great companies, we strive to hire the best and we value integrity, excellence, respect, inclusivity, and collaboration. What is special about Netflix, though, is how much we:

1. encourage independent decision-making by employees
2. share information openly, broadly, and deliberately
3. are extraordinarily candid with each other
4. keep only our highly effective people
5. avoid rules

Our core philosophy is people over process. 

Netflix Culture

Whether you use the term “values” or not isn’t the point – it is about having a written description of how you approach things. They describe how the team behaves, help you recruit new people who match those values and evaluate the existing team as to whether they are meeting those expectations.

Note the keyword: written.

The task of writing down the values is a good thought exercise in itself but then they can also be referenced and modified over time. If they’re not written down then there is too much of an opportunity for digression, forgetting key values or people just misremembering.

Another example is GitLab, who are unusually transparent in everything they do. Indeed, this is one of their core values.

GitLab’s six values are Collaboration, Results, Efficiency, Diversity, Iteration, and Transparency, and together they spell the CREDIT we give each other by assuming good intent.

GitLab Values

The important thing is making them actionable, for example under “Results” they explain:

Measure results not hours
We care about what you achieve; the code you shipped, the user you made happy, and the team member you helped. Someone who took the afternoon off shouldn’t feel like they did something wrong. You don’t have to defend how you spend your day. We trust team members to do the right thing instead of having rigid rules. Do not incite competition by proclaiming how many hours you worked yesterday. If you are working too long hours talk to your manager to discuss solutions.

GitLab Values: Results

Making the values actionable and measurable is what transforms them from high level clichés into a true set of operating principles for the company.

How do we work and collaborate together?

Do you message someone directly on Slack? Do you send an email with an announcement? Is it expected that you will engage in discussion in the comments on a Google Doc? Does documentation go in Confluence?

These are questions everyone has when they first join a company and so should be part of the standard operating system of the business. Everyone should be using the same tools and processes and there should be exactly one way of doing things. You know this is going wrong when you see such behaviour as:

  • Missing crucial information because it was sent as a Slack message late at night in your timezone and there were hundreds of other messages afterwards so you didn’t see it.
  • Bugs getting reported through anecdote, mixing multiple issues that then get fixed in an ad-hoc way without tracking the resolution, often resulting in duplicated work as other people try to reproduce an issue that has already been fixed.
  • People don’t check their email often because they don’t get many messages and instead work in real time chat all day, meaning they miss meeting notifications or an important customer message.
  • Documentation is written in Confluence by one team but another team is using Sharepoint to work on a Word doc.
  • People are mentioned in document comments but the answer is provided through another channel and the original comment is left open and unresolved.
  • Information and documentation exists in one place but it isn’t easily searchable so people end up asking individuals for work that has already been done.
  • Decisions get made without you being aware and you only find out through luck or because someone happens to mention it in passing.

Discipline is easier when the company is small and just getting started – that’s the best opportunity to set the rules and processes, and tell new hires how to do things. When there is a lack of direction, teams will end up using their own tools and systems because it’s better for them but to the detriment of the overall efficiency of the company.

Sometimes changes to working processes are needed, especially when a new tool is discovered that makes a difference to the working practices of the organisation. But adopting something new should be a deliberate evaluation and decision process.

If teams end up spinning off their own processes and tools, that is an indication of poor direction and/or failure of an existing approach. Dissatisfaction with the status quo should trigger a review and debate rather than a secret team/deployment of a new vendor product.

I personally dislike Slack (and any real-time chat) for anything other than general, social chat or deliberate collaboration on an ongoing project e.g. triaging a customer issue with a group of people in real time, doing incident response, or backchannel chat between participants during a sales meeting. These are all instances where a small number of people come together for a specific task and for a specific period of time, after which they disband. Real time chat is an awful tool for anything else because it implies everyone must be available and responsive immediately, at all times. Information is too easily lost.

My personal preference is defaulting to asynchronous communication via email, where I can set up my own workflow, control notifications and respond in my own time and in appropriate detail. Chat has its uses but I consider it (and notifications in general) highly damaging for any kind of focused knowledge work like writing or coding. This is not a unique view:

What we’ve learned is that group chat used sparingly in a few very specific situations makes a lot of sense. What makes a lot less sense is chat as the primary, default method of communication inside an organization. A slice, yes. The whole pie, no. All sorts of eventual bad happens when a company begins thinking one-line-at-a-time most of the time.

Is group chat making you sweat, Signal vs Noise

With 10 years of remote working experience with the majority of that spent with chat as a core communication tool, my preferred working style now is to assume that everything is asynchronous by default, with the ability to do urgent interrupts rarely.

Real-time sometimes, asynchronous most of the time.

At Basecamp our perfect-world rule of thumb is “real-time sometimes, asynchronous most of the time”.

Basically, right now should be the exception, not the rule. That creates space and attention for the things that really do have to be discussed right now, and allows everything else to be thoroughly discussed asynchronously and thoughtfully over time.

Is group chat making you sweat, Signal vs Noise

Real time chat like Slack has its place, but should be limited by both configuration and convention. For example:

1. Slack is to be used for informal communication only. Only 90 days of activity will be retained.

2. If you use Slack, please avoid private messages. Private messages discourage collaboration. You might actually be contacting the wrong person and they cannot easily redirect you to the right person. If the person is unavailable at the moment, it is less efficient because other people cannot jump in and help. Use a public channel and mention the person or group you want to reach. This ensures it is easy for other people to chime in, involve other people if needed, and learn from whatever is discussed.

6. Slack messages should be considered asynchronous communication and you should not expect an instantaneous response; you have no idea what the other person is doing.

Slack, GitLab Handbook

Limiting retention forces everyone into the mode of the chat being ephemeral and minimising private messaging helps encourage transparency, avoiding interrupting specific people. And if it really does need to be synchronous, a video/audio call (which can then be recorded, transcribed and stored in a searchable format) is still probably better.

What is expected of me?

At this point we are down to the day to day activities of individual team members. If the above items are done well, each person will understand what the company is doing, what guides their approach and the key tools and processes they should be using. That leaves the question: what should I actually be doing?

The worst kind of work is where you are simply following orders. Sometimes specific tasks will be assigned e.g. preparing a spreadsheet of KPIs or fixing a reported bug. However, most work should be driven by outcomes, leaving the individual to decide how they achieve it guided by the mission, values and tools.

There are plenty of systems that can be used to decide what should be worked on, with the most popular (at least in startups and Silicon Valley) being OKRs. I’m actually not a big fan of them and couldn’t get them to work well at my company, but I do subscribe to some of the key principles of OKRs, specifically:

“The ability to track results on a quantitative basis.” Key results are not general or subjective actions you plan to take. They should always include numbers to make it clear how much has been achieved. For example, if Mary’s objective is to improve her sales prospecting skills, one key result might be to spend two hours a week shadowing Jennifer, the team member who demonstrates the most prospecting success.

How to Make OKRs Actually Work at Your Startup

Whatever system you use, the key is that people know what they should be doing and how it links to the overall company mission. OKRs are one way to achieve this but need to be implemented with all the other things discussed above – they won’t just magically solve a communication problem if there is no understanding of the company mission, values and processes. The team should not only know what they’re supposed to be working on and why, but be able to explain it to others:

Following the HR rep’s suggestion, I start to ask questions. Actually, a single two-part question: What are you doing, and Why?

For the What, I rely on a variant of my old I Can’t Be Stupid gambit: If I don’t understand what you’re saying, either you don’t actually know what you’re talking about, or you’re withholding something. As for the Why, please don’t say you’re just following orders — I know you have a mind of your own; and don’t hide behind “marketing demanded it” as if you respect marketing. Tell me how your work serves the common purpose. Does it improve performance, reduce cost, increase reliability, forge a killer feature? If you can’t tell me, perhaps you should go back to your desk, gather your thoughts, and come up with some answers that make me feel smarter and safer.

50 Years In Tech. Part 12: Cupertino Culture Trouble

What is the rest of the company doing?

With all of the above implemented, everyone should have a good idea of where the company is going and what is being worked on, at least at a high level. Knowing what is actually happening on a day to day basis is easier in small companies but as the team grows and the product becomes more complex (possibly with multiple products), it becomes harder to know who everyone is and what they’re individually doing.

This essentially comes down to two things:

  1. Transparency: are the systems, tools and processes open enough so that anyone can look at any document or ticket if they wish (subject to certain restrictions around confidentiality – GitLab again have good guidelines on what is not default-public)?
  2. Real communication: is there regular discussion from the executive team explaining what is going on throughout the business – whether that is highlighting big (and small) wins, releases, problems or just regular reporting on activities.

There is also a question of relevance. In a company of 10 people it makes sense for everyone to know everything, and to be specifically told about all activities. If you have 10,000 people then the level of detail needs to change. Information should still be available if individuals wish to look it up, they just might not be told the complete detail on a regular basis.

Most companies do a poor job at this, especially the bigger ones. Coordination across teams within a single department is often frustrating enough that trying to get all teams fully aware is a big challenge. That doesn’t mean it can’t be done.

One good example where this is a regular problem is with the selection of technology and building internal systems. Large companies, organisations and especially the public sector suffer from duplication of systems which can only really be solved through proper value chain mapping.

Wardley Maps are a great way to understand the landscape, something which most companies are awful at.

This doesn’t just stop at knowing who is building what but actually goes into the entire company strategy. That’s an entirely separate topic, though. Read the book on Wardley Maps for the real detail.

So how do you achieve this?

Establishing a regular communication and reporting cadence is a standard part of running a public company – financials and progress get announced in an expected format on an expected timeline. If public companies can do this on a quarterly basis, there’s no reason why smaller companies can’t do it too, and likely much more regularly.

At my company, I used to send out monthly updates to all my investors via email. This tied in with my monthly board meetings and included details about all KPIs, an analysis of the results and what the plans were for the next month. I sent out the exact same report to all team members internally as well.

I also ran weekly whole company meetings where everyone had a minute to talk about something interesting they had done during the week, and as the CEO I commented on positive developments, good work I’d seen and provided an update on challenges, problems or anything else that was relevant.

If I was implementing this again I would think about the following:

  • Reporting KPIs on a weekly basis via email and highlighting the top 2 metrics in the weekly meeting (likely revenue numbers). A good real-world example of implementing a system of reporting is described in The Founder’s Guide to Discipline: Lessons from Front’s Mathilde Collin, particularly around regular emails and meetings to highlight progress.
  • Building an internal KPIs dashboard with real time data that everyone could access.
  • Recording and transcribing all meetings so they are easily searchable and reference-able in future, then emailing this out to the entire company (for the whole company meetings, and having a good index for all other meetings).
  • Having all individual goals and measures for the “What is expected of me” section public on some kind of internal profile directory. This helps to answer the question of “What is the rest of the company doing?” and means people can directly link to their goals when helping others prioritise work. If everyone knows what you’re working on and why, they can figure out how their request can help achieve the goals of both parties.
  • Regularly discuss all aspects of the company mission, values and processes to get input on what is working and what isn’t. Just because you decide on an approach when the company is founded does not mean that you have to stick to it.
  • Being more deliberate about having a single source of truth for all documentation, values and the overall company handbook from the beginning of the founding of the company.

Communication is not static. The best way to do something today might change tomorrow. You have to repeat things and ask obvious questions. It can be difficult to know how well communication is actually working but you can certainly tell when it’s poor. Things are often getting done despite the communication overhead. People are guessing what they should be doing and there is a low level buzz about how well the company is truly doing. Nobody has any guiding principles helping them decide what they should be doing and there is often a lot of sudden urgency around arbitrary deadlines like working in a feature factory.

This is a big challenge all companies face, and it is one that is never solved. Whether you have an extreme level of secrecy and control like Apple or at the other side of the spectrum like GitLab, I think monitoring communication and actively working on improving it should be a top priority for the entire executive team.

Further reading

Influence is the product manger’s best tool

The product organisation is unusual in that it achieves its goals through influencing other parts of the company rather than through a managerial relationship with individuals that sit with its direct reporting line.

A typical product group will have a leader reporting into the CEO who then has product managers reporting into them. The number and complexity of those products will determine how deep that org chart is but the people actually doing the implementation are usually part of another reporting group e.g. engineers report up to the VP, Engineering (or perhaps the CTO).

This is of course a generalisation, but it’s rare to have engineers reporting into the product manager, for example. The same applies to other aspects of the company – marketing reports though the VP, Marketing or CMO. Sales is led by the VP, Sales or CRO. And so on.

Despite this, the product manager is working very closely with all these areas of the organisation. They define large parts of what the work is (but not the how) but are unlikely to be directly assigning tasks or “managing” the team they are working with.

This means that good product managers must rely on their powers of influence and persuasion to make a case and explain why something should be implemented. They have no direct reporting authority or rank, so must take care to build up respect and authority by the quality of their work.

In practical terms, this means:

  • Understanding the customer better than anyone else. Sales might know best about what prospects are looking for before they become customers, and support might understand key pain points in product usage for existing customers, but it is the product manager who should have the best understanding of the customer as a whole, across their entire lifecycle using the product. Product manager activities should involve bring on sales calls, visiting customers on-site, participating in UX reviews, dipping into support tickets and chats, running feedback sessions with sales and support, and triaging customer feedback.
  • Understanding the market better than anyone else. Marketing probably know how to generate the widest reach in the most targeted way and finance truly understand how margins should be optimised, but the it is the job of the product manager to understand why one marketing idea might be better than another based on an understanding of how customers consider alternatives, buy and then use the product. And to give finance the input they need about competitive pricing and operational costs. Product manager activities should involve collaborating on the go-to-market plan, reviewing funnel statistics, engaging with analysts, understanding infrastructure costs, testing competitor products, positioning product pricing packages against features and customer personas, discussing deal win/loss reasons with sales and understanding churn reasons.
  • Communicating across the organisation. Communication is the biggest challenge in any company, and only gets more difficult as it grows. There are so many levels of granularity in delivering a successful product so it is crucial that everyone understands the long term vision and how that translates into each feature release. Product manager activities should involve discussing the strategic plan with the CEO/executive team and with the wider product manager group, testing out pitches with real customers (can you articulate how you got to where you are today, and where the product is going?), sending out regular product updates to customers (newsletters) and internal groups (changelogs), building training decks for sales/support, then delivering the training itself, writing up roadmaps, converting feedback into product specs, helping debate the prioritisation of key initiatives and explaining to sales/support why something is going to be done (or not done).

Product management truly is the job with the most cross-company influence but is least able to rely on rank and position to derive authority. It means it is one of the more difficult roles to start from scratch in, but has the most opportunity to build influence and authority through results.

Product managers are not responsible for “how”

Product managers are responsible for two aspects of their product:

  • The product itself: what should we build, why, and when? This involves working with sales (deal win/loss reasons), support (patterns in support requests), engineering (product development, testing and release) and operations (supporting the infrastructure behind the product).
  • The go-to-market approach: what should we do to raise awareness and generate new revenue? This involves working with sales (training on new releases, working on sales collateral, being on calls with prospects) and marketing (influencing product marketing campaigns, attending conferences, creating content).

There are nuances within these categories e.g. if the release is about improving a difficult area of the product interface, the go-to-market approach may involve only existing customers and churn reduction rather than new revenue. Or a release may focus on reducing specific alerts and incidents for the on-call team, rather than direct customer functionality. But much of the day-to-day of a product manager will revolve around these two aspects.

Amongst all the things that the product manager is responsible for coordinating it is important to note the key aspect they are not deciding: how.

Whether you agree or disagree that the product manager is like the CEO of the product, once you get past the early product prototypes and have the scope to hire dedicated product managers, their job does not involve deciding how things should be done.

At the point when your team is big enough to include product management, it will also include specialists in engineering, operations, sales and marketing. They will have taken over from the generalist founders and should be much better than the original team who hired them. That’s why you hired them in the first place!

The same applies to product managers. Their job is to get into the details of what should be done and when, coordinating all the resources and people to hit product goals (revenue, launch, NPS, churn, etc). Their job is to define the outcome everyone is aiming for, not to determine how it should be done.

Designers decide how to build the best user experience.

Engineering decides how to implement a feature.

Operations decides how code should be deployed.

Marketing decides how to spend their budget.

Sales decides how to engage potential customers.

Support decides how to deal with inbound customer requests.

The “how” of product is deciding how the product delivers on the business goals through the teams that the product manager then has to coordinate. This involves “what”, “why” and “when”. It includes providing ideas and input into helping the other teams figure out their “how”, but that decision rests with the team actually doing the work.

How to onboard new employees

Most people seem to focus on the stages of the recruitment process before the employee starts. This is understandable given how difficult it is to source candidates, and then run the interview process.

However, it’s just as important to consider how new employees are onboarded into the new role. The first few weeks and months are critical to set people up for success, and determining if you actually made the right choice in hiring. There’s a reason most employment contracts have a probation period – this is the time to discover if your hiring process worked.

What does success look like?

The biggest mistake I’ve seen is that the job specification only describes the characteristics of someone who you would like to do the job, but no criteria for checking if that person is succeeding or failing. It should include a detailed description of what you expect the person to be doing and how you measure that output.

Indeed, how do any of your team know they are achieving what is needed for the business? There may not be quite as direct a correlation as with sales quotas, but there should be some objective criteria for every role which determines whether that person is performing or not.

This is idea behind OKRs – having objective measures which are regularly reviewed. We didn’t actually manage to make them work at Server Density but we still had metrics that we reviewed on a weekly basis to ensure that we were tracking towards our overall objectives, which were then discussed at the monthly board meetings.

For SaaS businesses, the key metrics are well understood. MRR, churn (net MRR churn and customer churn) and NPS are typically the three key numbers relevant for all areas of the business. Then each team might get something more granular e.g. cashflow for finance, funnel metrics for sales, critical out of hours alerts for ops, ticket satisfaction for support, CPA/payback rate for marketing, etc.

At Server Density, our new engineers had a goal of deploying to production by the end of the first day, although our expectation was that it would be a good 3-6 months before they were fully up to speed to work independently on the codebase. These short term vs long term goals really help set expectations.

Operational onboarding

This is where most onboarding starts and ends. It consists of setting up the mechanics of how the employee will actually get work done: laptop, email, chat tools, etc. This is obviously important, but should really be the easiest aspect of onboarding, and the one that is the most optimised.

That means all the crucial accounts, applications and systems are already set up and the computer the employee requested is ready to go. So much time is wasted with initial setup of laptops, creating email accounts, etc when this can easily be automated and be completed in advance of the first day.

Managerial onboarding

Everyone has a manager. This is someone who will help you get your job done, remove obstacles, act as a career mentor and hopefully offer proper feedback in one to ones. Getting off to the right start with your manager is often daunting – you don’t know how they work, what they’re like and how best to get what you need from them.

I like the idea of a Managerial Manual which describes exactly this. My favourite example is How to Rands, something I’ve seen implemented by several managers at my company, StackPath, as well.

Cultural onboarding

As the team grows, the culture will diffuses from “how the founders do things”, so the values and mission of the business need to become more formalised. This was something I wasn’t really aware of when I started Server Density – we were very informal about explaining how we did things and only wrote down our approach when we faced a problem with how something was being done.

The Netflix culture is probably the most famous and it is worth reading about what they mean by the term, but every founder and every company has a different approach to things. If I was starting a new company today, one of the first things I’d do would be to write out the mission and core values I wanted to build out. Values are what you hire against and describe how you operate. The mission is a short statement describing why the business exists through what it aims to achieve long term.

You also have to be careful of “culture fit” meaning “same as me”:

Finding the right people is also not a matter of “culture fit.” What most people really mean when they say someone is a good fit culturally is that he or she is someone they’d like to have a beer with. But people with all sorts of personalities can be great at the job you need done. This misguided hiring strategy can also contribute to a company’s lack of diversity, since very often the people we enjoy hanging out with have backgrounds much like our own.

How to hire, HBR

But you do need to find people who both understand and believe in the mission as well as agree that the values are the right way to achieve it.

Onboarding gimmicks

In addition to considering all the above, there are some impressive but gimmicky things you can do to make new employees feel welcome. I use the word “gimmick” in the sense that these are good ideas to impress someone on their first day, but aren’t really part of “onboarding” in the same way as the more important things above.

  • Swag – have a parcel of tshirts, hoodies, socks, stickers, etc ready and waiting for them on their desk. All correctly sized, of course.
  • High quality printed version of the company culture deck/values/mission.
  • Handwritten welcome note from their manager / the CEO.
  • Lunch / dinner with the management team / CEO.
  • Announcement introducing the new employee to the whole company.

Isn’t this a lot of work?

Yes. That’s the point. You can’t achieve anything without a great team, and it is absolutely necessary to spend a significant amount of time on the full end to end process: hiring, onboarding and then ongoing management.

To quote a good First Round Review article on this:

You say you’re too busy. You work at a tiny startup after all. But that’s no excuse, Guthrie says. “You’re not too busy. You just spent all this time, energy and money getting this new person to join. Blowing it is going to cost you even more when you have to start the hiring process again from scratch. Don’t make someone feel like you’re too busy to make them feel good about choosing to work with your company.”

Your goal should always be to make people believe on a gut level that your organization is so amazing that they couldn’t possibly work anywhere else. Building that attitude starts immediately once an offer letter is signed. And if you do it right, when the phone rings and it’s a recruiter on the end of the line offering the next big thing, they’ll say, “Sorry, I’m happy where I am.”

Questions for when things aren’t working

There are many times when you have a goal, you try something to achieve that goal, but it doesn’t seem to work. Whether it is in trying to grow a startup, writing a piece of code or in a more personal area of life, this will be a regular occurrence. It’s often called iteration and improvement, experimentation or trial and error.

But how far does that approach go? When does the trial become an error? What do you do when things aren’t working?

1. Define what “working” looks like

This should be obvious but unless you know what the end result should look like, how can you evaluate whether whatever it is you’re trying is “working”? The best way to do this is with a single number you can measure easily. That is not always possible but the closest you can get to a quantitive metric, the better.

2. Set a timeline

You can’t continue indefinitely. You need to see progress within a reasonable period of time. You already defined what the end goal looks like, but you also need a measure of “progress” towards that goal.

This has to have a time frame because how do you know whether to keep going or stop? Knowing when to stop something is just as important as deciding when to start something.

Are you almost there or do things just keep creeping forward? Is there an illusion of progress if you look at things in isolation, but when you zoom out on the timeline then you really haven’t come far at all?

3. Get a second opinion

It’s difficult to be objective when you are deep in something day to day. You have the full context to make micro, operational decisions but you also need someone who can consider things more independently. In business, this is usually the role played by the board. Talking to close friends is similar in a personal situation.

You need people who will listen and understand, but also who are not afraid to give their true opinion.

Sometimes you can make a decision by yourself but asking a few, experienced people what they think gives you additional data points to align with. You might decide to discount their opinion this time round but each time you come back with the same result, your threshold for dismissing their opinion should increase.

4. Repeat, but not too many times

Whether or not it was Einstein who said it, the old quote applies:

the definition of insanity is trying the same thing over and over and expecting a different result

Going back and tweaking variables, making changes, taking different approaches. These are all normal responses when things aren’t working. This is how debugging works! But there is a limit to how many things you can try. Ask yourself:

  • How is it different this time from the last time I tried it?
  • Is it actually different, or just a minor tweak on something we already tried?
  • Do I need to make a minor tweak or should we have a major rethink?
  • If I am trying the same thing again, why would it be different this time?
  • What needs to change in my approach to get an order of magnitude difference in result?

5. What are the consequences of making the decision?

Jeff Bezos has an approach to decision-making based on whether the result is reversible or not.

Some decisions are consequential and irreversible or nearly irreversible — one-way doors — and these decisions must be made methodically, carefully, slowly, with great deliberation and consultation. If you walk through and don’t like what you see on the other side, you can’t get back to where you were before. We can call these Type 1 decisions.

But most decisions aren’t like that — they are changeable, reversible — they’re two-way doors. If you’ve made a sub-optimal Type 2 decision, you don’t have to live with the consequences for that long. You can reopen the door and go back through. Type 2 decisions can and should be made quickly by high judgment individuals or small groups. 

Jeff Bezos, Letter to shareholders

Is it usually easier to take the path of least resistance and just “keep going”. Repeating with minor tweaks appears like it should be a type 2 decision, and it probably is for a while.

However, the cost of repeating compounds over time. Each time you try one thing, you’re not trying something else. This is the opportunity cost, and a type 2 decision can quickly morph into a type 1 decision.

6. What is the opportunity cost?

The expression in your while loop above needs to be determined by your opportunity cost. What would you otherwise be doing with your time/money/team/life if you weren’t doing the above?

Everyone has a different understanding of their opportunity cost but the cost is never zero. Nobody has unlimited time or money. And it’s not just your own opportunity cost you might be wasting – what about everyone else who is involved? What do you care about? What do they care about? Would you time be better spent pursuing those goals in other ways than what you are doing right now?

I think opportunity cost is the one most people under appreciate. It has the highest impact yet is the most difficult to see, because it only becomes obvious over a long period of time.

Startup holiday policies – unlimited time off doesn’t work

As an early startup founder, you have unlimited flexibility to work when and where you want, and for as long as you want. It only makes sense to extend that flexibility to the whole team, right? Indeed, that’s where the idea of “unlimited” holiday came about. I adopted this as our holiday policy when Server Density was founded in 2009.

However, it didn’t really work out as intended. The problem is that there is always something else you should be doing. It’s never a good time to go away and you certainly can’t disconnect completely. I travelled quite extensively in 2010 both to the US for the company and my first ever trip to Japan on holiday. But I didn’t ever have a true “holiday” in that I could completely disconnect from work.

If the founder and CEO can’t take real time off, how do you expect the rest of the team to be able to interpret the “unlimited holiday policy”?

Over 9 years at Server Density, we tried several different approaches to holiday policy. I’ve previously written about startup financial incentives so this post is about the different holiday policies we tried:

Unlimited holiday policy

With this policy, there is no quota and anyone can take as much time off as they like, subject to manager approval. The company does not count the days off each person takes, although it is of course still recorded so everyone knows if someone is off.


  • It sounds good, especially to those new to startups. Everyone likes the idea of “unlimited” because it means they don’t need to worry about whether taking a day from their allowance is a good use of time, and won’t miss out on events because they’ve used all their allowance.
  • You can use it to make the most of travel opportunities. The further away you go from home, the longer it takes to get into the timezone and so the more time you want to spend in a destination. I know 2 weeks is the minimum amount of time I would want to take for a trip to Japan.


  • There is no guidance about how much is “reasonable”. You will probably not hire someone who will take advantage and disappear for 3 months, but what is the right amount? Expectations are ambiguous and if the founders/senior team are not taking much time off, the rest of the company may feel pressure to avoid holiday.
  • Without guidance, some people will take off more time than others. Perhaps those will fewer deadlines or less pressure will find it easier to take holidays. Managers will be reluctant to approve holiday, especially longer trips. And when holiday is taken there will be an unspoken pressure to “check in”, with email or Slack.
  • If you don’t actually track time off, you can’t tell if someone is abusing the system or let other people know people are off. So you do have to track it, which means it is not “unlimited holiday” but “no measured allowances”.
  • The startup marketing doesn’t match the reality, which hurts your long term reputation. If a new candidate asks your team (or reads a Glassdoor review), will they be enthusiastic about the reality of working there?

Bonuses to encourage people to take time off

With the realisation that the pure “unlimited holiday” policy wasn’t necessarily working out for everyone, we decided to introduce an incentive to take time off. This amounted to a £1000 cash bonus at the end of the year if you took at least 25 days in the calendar year. This was originally a 50% salary bonus in the final month of the year but we adjusted that to a fixed amount because it became expensive.


  • Using a financial incentive to encourage behaviour is a well understood approach. It is used in all sorts of areas of life, from sales commissions through to encouraging people to give up smoking.
  • It makes it clear what the holiday policy expectations are. The actual number of 25 days could be changed but it sets a clear guideline for how many days you are encouraged to take.


  • It assumes everyone is incentivised by money.
  • How do you set the amount? £1000 means different things to different people but a percentage of salary is also somewhat arbitrary and can prove expensive.
  • How do you deal with edge cases e.g. someone who takes 24 days? Is it fair that someone who takes 25 days gets the bonus whereas the person who just misses it does not?
  • If someone suddenly realises towards the end of the year that they need to take time off, what happens if it is not a good time or lots of people are in a similar position? You could see lots of holiday requests right at the end of the year.
  • How do you deal with people who join the company part of the way through the year? Pro-rate the 25 days? Pro-rate the bonus?
  • It introduces a large cash outflow in the final month of the year. As your team grows, this could become a problem for cashflow.

Setting an expected minimum with active encouragement

After trying the above, this is the approach we were using before Server Density was acquired. We had an unlimited holiday policy, tracked all time off but set an expectation that everyone would take at least the UK statutory minimum – 28 days. Anything over that was generally allowed, subject to sufficient notice, availability of any cover and in consideration of occasional deadlines. In practice, we rarely denied requests for time off and most people were in the 30-35-days range each year. We also removed the bonus.


  • The expectation is clear and it follows the legal requirements. The UK fits nicely in-between the crazily low allowances of the US and the quite-high expectations common in Europe, so it feels like a reasonable middle-ground.
  • It is a good benefit to talk about when recruiting because it’s still unusual to have “unlimited” holiday in the UK, outside of tech startups.
  • It is down to managers to ensure their team take the minimum time off, spread throughout the year. This removes some of the responsibility from the team member and makes the manager think about any pressure they might be applying to work under unreasonable pressure.


  • It is still “unlimited” and so the value of having a day off is less than if each person had an annual allowance. To me, this means taking paid holiday doesn’t have the same feeling of value. If you can have as many days off as you like, you value them less. Using something like time off in lieu therefore has no effect and individuals may appreciate the holiday time less.
  • There is an upper limit. As a founder, you have to set the example and what if you want to go on a 3 week holiday? That’s almost all your allowance gone.

Conclusion – how would I do it today?

Unlimited holiday by itself simply doesn’t work. Many others have found this, too.

Introducing financial incentives also doesn’t work. The differences are marginal and it can end up being expensive for the company.

However, the motivations for exploring these kinds of policies are still essentially valid. You want employees to feel trusted to balance the needs of the business and their desire for time off, give them the flexibility to enjoy life and make expectations clear so that nobody feels unnecessary pressure to work so much they burn out.

If I was creating a new company holiday policy today, I would go with fixed allowances. This would probably start at the UK statutory minimum during the employee’s first year and then gradually increase the longer they have been with the business. This is similar to how Basecamp run things – 3 weeks plus a few extra days here and there if needed.

I would also be flexible e.g. if someone had used all their days off but wanted a day or two more for an important event, it seems unnecessarily mean to deny the request. I would also consider allowing some unused time off to be rolled over into the next year. This would encourage employees to think about time off as something of value, but also that the company encouraged people to use it.

Ultimately this is about balancing the requirements of the business and the needs of the team, which should align almost exactly most of the time. If employees feel rested and relaxed, and feel like they don’t need to strictly count time off, the business benefits as well as the employee. The advantage of early-stage startups is that you can experiment with these things.