An Uncomfortable Question

October 18, 2026

Jerry Colonna, a venture capitalist turned executive coach, asks a question we often return to with clients: “How are you complicit in creating the conditions you say you don’t want?”

It’s an uncomfortable question, that’s why it’s effective.

Most of us can give a detailed account of what’s wrong. We can explain why our team isn’t stepping up, why our calendar is out of control, or why things feel tense at home. We have examples, and usually, we have a pretty clear sense of who needs to change.

Colonna’s question interrupts that account. It asks us to consider something we may have conveniently left out: our own contribution.

You want your team to take more ownership, but you keep stepping in before anyone has a chance to figure things out. You want fewer meetings, but you accept every invitation. You want an honest relationship with a colleague, but you’ve spent six months telling everyone except that colleague what’s bothering you.

The same patterns show up in families. You want your children to be more independent, but you solve every problem for them. You wish your partner would open up more, but when they do, you correct them or start offering advice. You resent being responsible for every family gathering, but you keep volunteering before anyone else can.

These choices make sense. We step in because we want to help. We put off a hard conversation because we’re worried about how it will go. And even when we’re worn out, it can feel good to be needed. These habits do something for us, which makes them hard to change—even when we wish things would turn out differently.

We ask clients about their complicity because it gives them somewhere to begin. You may have very little control over another person’s behavior, but you can choose to have the conversation you’ve been avoiding, set the boundary you haven’t established, or stop offering help that hasn’t been requested. Acknowledging your part doesn’t mean accepting blame for everything, but it does mean recognizing you have a say in what happens next.

To push a little further, reflection often becomes a satisfying place to stop. We recognize a pattern, have a good conversation about it, and feel we’ve made progress. Sometimes we get very good at explaining why we do the thing we continue to do.

Spotting the pattern is only the beginning. The answer must become an action. Let a team member work through a problem without rescuing them. Tell your colleague what you’ve been withholding. Listen to your partner without preparing a rebuttal. Let your child struggle with something they’re capable of handling. Then notice your urge to step back into the familiar role, that’s often where the real work begins.

The next time you hear yourself describing a condition you don’t want, ask Colonna’s question. Give yourself time to answer honestly. Then ask one more question: What will I do differently now that I know?

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