People are good at diagnosing what’s wrong. They’re not great at following through and fixing it.
They say things like:
“I think I need to ask my cofounder to step down.”
“I know this sales hire isn’t working.”
“That person is underperforming, and it’s putting the whole project at risk.”
“I don’t believe this strategy is going to work.”
If I ask the right questions, most founders can tell me exactly what’s wrong within the first ten minutes. Without intervention, though, the same issue is often still sitting there six, nine, twelve months later.
Nothing has changed, despite their having articulated the problem perfectly.
Why are we so good at diagnosing the issue, and so bad at acting on it?
Diagnosing a problem and fixing a problem are two completely different skills, and only one of them comes loaded with feelings you’d rather not have.
You can diagnose an issue entirely in your own head, over a period of months, without ever having a single hard conversation. If you’re close to your business, your read on the situation is probably right most of the time. It’s easy because it costs you nothing. It’s an objective read on a situation, done in the privacy of your own head.
Fixing it is different.
Fixing it means a confronting conversation with a real person, and that conversation is going to make you feel things you’d rather not feel. So you put it off. You tell yourself it might turn around on its own, or that maybe you’ve overstated the problem and it doesn’t really need fixing after all. What you’re actually avoiding is the emotion, not the decision.
Often, my job isn’t to help a founder see the problem. It’s to help them sit with the discomfort of fixing it.
Usually, there’s no magic wand that makes the discomfort disappear. If you have to fire someone you genuinely like, that’s going to feel bad no matter what I say. What coaching does is help you find a way to sit with that feeling long enough that it stops being the thing controlling your decisions. It stops feeling as consequential or scary, so you can take the action anyway.
In practice, that looks like three things.
- Name the fear. What do you think is actually going to happen when you have that conversation? What do you imagine you’ll feel in the moment you say it out loud? Most of the time, the fear is smaller and more specific than it feels in the moment. If we agree on what it is, we can start normalising it.
- Shrink the action. “Fire your head of engineering” is a big step you might not be willing to take straight away. But, “Have one honest conversation with your head of engineering this week about the thing you’ve been avoiding” is an achievable step.
- Borrow confidence. Sometimes all a founder needs is to hear, “Yes, that’s 100% the right call, I agree with you.” You can borrow that conviction from me to go and act, while you build your own confidence.
And underneath all three, there’s accountability. If you tell me this week you’re going to have the conversation, and you know you’ll have to report back to me on how it went, that alone makes you far more likely to actually do it.
If you’re stuck on something right now, ask yourself honestly if you already know what the right move is. If the answer is yes, stop looking for more clarity. You don’t need it. Ask instead what the smallest version of that action looks like this week, and what you’re actually afraid will happen if you take it.
Sit in the discomfort with me.
- Scott Handsaker is a startup and executive coach, as well as a co-founder at Redwood, a private network for Australian founders.
