The Complicity Question
Ask how you helped create the conditions you claim you don't want, to reclaim your agency
- Difficulty
- Moderate
- Time to result
- ~ongoing to results
- Steps
- 4
- Confidence
- 95%
A single self-inquiry question that surfaces the ways you unconsciously perpetuate the situations you complain about. It deliberately uses 'complicit' rather than 'responsible' so the point is not self-blame but recovering agency — seeing where a hidden payoff keeps you stuck. It is a repeatable daily practice, not a one-time exercise.
Origin
Jerry Colonna's signature coaching question, developed over his 27 years as an executive coach and central to his book Reboot.
Core principles
- 01Complicit means accomplice, not culprit — you drove the getaway car, you didn't rob the bank
- 02The goal is to evoke agency, not to assign fault
- 03Behind a stated aversion often sits a hidden reward that keeps the behavior alive
- 04Naming the payoff is the first step to choosing a more conscious way to meet that need
How to run it
- 1
Name the condition you say you don't want
State plainly the recurring situation you complain about — e.g. 'I don't want to feel busy all the time.'
Pro tip Use the exact 'I say I don't want ___' phrasing to keep it in your own voice.
- 2
Ask how you have been complicit in creating it
Distinguish complicit (accomplice) from responsible (culprit). Look for the small ways you enable or feed the condition rather than blaming yourself for it.
Watch out If you slide into 'how am I responsible for the mess in my life,' you've missed the point — that self-blame shuts down inquiry.
- 3
Surface the hidden payoff
Ask how it serves you. Colonna's example: feeling unnerved and disconcerted when the agenda isn't jam-packed reveals that busyness is meeting a need for a certain feeling.
- 4
Choose a more conscious way to meet the need
Once you see the payoff, look for a healthier route to that same feeling instead of the self-defeating one, and repeat the question regularly as a practice.
Pro tip This is a question you can ask yourself every single day, not once.
In the wild
Colonna offers himself as the example: 'I say I don't want to feel busy all the time but the truth of the matter is I feel really unnerved and disconcerted if my agenda isn't jam-packed.' Radical self-inquiry then asks how it serves him to feel busy to the point of exhaustion.
→ The busyness is revealed as a chosen way to get a feeling of security, opening the door to getting that feeling more consciously rather than 'feeling like crap all the time.'
A CEO of a 15-person company asked why nobody on her team could make a decision without her. Colonna asked who hired them (she did) and how she felt when they made a decision she disagreed with — 'I'm furious.' Her intolerance of disagreement was her complicity in the very dependence she complained about.
→ Reframed as her 'growth edge': to build a scaled leadership team she has to tolerate people making boneheaded decisions about things she cares about.
Common mistakes
Reading it as a blame question
Hearing 'how have I been complicit' as 'how am I responsible for the shit in my life' turns a tool for agency into self-flagellation, which paralyzes rather than frees.
Treating it as a one-off
People ask it once during a crisis and move on. Colonna frames it as a daily practice of 'continuous inquiry' — the payoffs and complicities shift over time and need re-examining.
Is it for you?
Best for
Founders, executives, and high-achievers who keep complaining about a recurring condition (busyness, a dysfunctional team, a stalled relationship) they feel powerless over
Not ideal for
Situations of genuine external victimization where the person bears no agency and the framing would wrongly imply self-inflicted harm
From the transcript
“How have I been complicit in creating the conditions I say I don't want?”
“I purposely chose the word complicit because complicit does not mean responsible.”
“you are driving the getaway car. you're not sticking up the bank teller.”
“The purpose of this question is actually to evoke your own agency.”
“I say I don't want to feel busy all the time but the truth of the matter is I feel really unnerved and you know…”
From the episode
How have I been complicit in creating the conditions I say I don’t want?
Jerry Colonna (CEO of Reboot, executive coach, former VC)