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.