Staying connected to the front line

As companies grow, more responsibilities get delegated. The team gets larger and the distance between the CEO and the lowest level employee expands. Same with customers. Front line support takes over, shielding engineering and management from direct contact with users.

This is a challenge for startup CEOs. Weekly one to ones with every employee eventually become impossible. At some point it becomes impractical to read every incoming support email. But as this becomes more difficult, it becomes more important.

When was the last time you, as an employee, spoke to the CEO or your manager’s manager? When was the last time you, as the CEO or manager, spoke with a customer, and not just the top accounts?

The CEO is always the last person in the company to know about a problem. If someone is thinking about leaving, if there is a major bug, if a big customer is planning to churn, you can bet that it is already well known within the organisation. Communication is hard.

It is impossible to completely solve this but as the CEO or as a manager, you must still work to stay connected to your organisation.

Staying “in touch” as a manager or CEO #

• One to ones are crucial to understanding your direct reports, but there is an upper limit of about 7-10 people you can effectively manage. Any more direct reports than that and you have to sacrifice quality. Weekly one to ones become difficult to schedule and poor managers end up cancelling or making them more infrequent. This is fixed by reducing the number direct reports by adding a new management layer but this increases the distance between you and the front line workers. You must still meet with as many of your team as possible, just less frequently. This is known as the skip level meeting and applies across reporting lines as well as within your own organisation. At large companies it will eventually become impossible to meet every employee but you should still speak to a representative sample across all teams.
• In a small startup it is easy for everyone to do support but this becomes difficult when you have hundreds or thousands of customers. At my old company, Server Density, even though we had a dedicated support team, everyone received the initial “new ticket” notification with details of the opening issue. This worked at 20 people and 10-20 tickets per day. At larger companies, you can do things like sending out summary reports of top reported issues and rotating everyone into the support team for a week a year. This is especially important for engineers building products so they get to understand their user’s problems. Good quality writing is a crucial skill and communicating with customers is a great way to practice.
• After the early stages, one of the few things the CEO should be focused on is speaking to new and existing customers. The CEO is the ultimate salesperson and after product-market fit, their involvement in deals is usually limited to the biggest and most important customers. However, it is still important to understand the full cross-section of your user-base, not just the most valuable users only at steak dinners. If Jeff Bezos (Amazon), Richard Branson (Virgin) and Tony Hsieh (Zappos) can do this, so can you.
• Buy and use your own product. As the supply chain gets increasingly complex, there will be more opportunity for issues to creep in at various stages. Browse your own website. Attempt to sign up. Explore the onboarding and then buy with your own credit card. There may be multiple teams responsible for the various stages but the customer is only going to experience it as a single flow. Have someone own the full delivery stack to ensure it all ties together.