My Favorite (Self) Coaching Question

At the start of coaching sessions, clients often tell me a story about a challenge they're facing. 

There’s a frequent pattern to these stories. The way most of us synthesize what’s happening around us typically maximizes the virtue of our perspective and actions, while casting the perspectives and actions of others in a far less flattering light. We also sometimes ascribe agency to others or “the situation”—they’re acting upon us—making us the victim of the story. 

That’s where my favorite coaching question comes in: How are you complicit in creating the conditions you say you don't want?

That question is inspired by Jerry Colonna, who mentioned it on the Tim Ferriss Show in 2019. The reason I like that question is several-fold.

1)  The question  primes us to remember that we have agency. 

Colonna says the phrasing of the question is purposeful: ”I like to use the word complicit and not responsible. 90% of the time when I first ask that question, people hear…’How have I been responsible for the conditions?’ Complicitness is important, because [it relieves] the person from the burden of feeling responsible for all the [stuff] in their lives, because that’s not fair to carry that responsibility.”

But while we don’t have 100% responsibility for our situations, recognizing that we are a leading actor in our stories is often the first step to being able to resolve or move around the challenges. I may not be able to fix it, but I can fix my part of it. 

That reframing can clarify the challenge we face. It might sound like: 

• I have this problem because I’ve chosen not to fix it or raise a concern with the person who could. 

• It’s not the problem itself, it’s that I’m letting it bother me when I’m outside of work. In that sense, I’m making someone else’s problem become my problem. 

• That dude really is a jerk, but I can choose how I respond.  

2) The question can spark learning. 

By identifying our own complicity when reasoning through a challenging situation, it’s more likely that we go beyond resolving the challenge narrowly and instead identify ways that we can improve ourselves. And hopefully, that leaves us in a better position to prevent or avoid getting into the same challenge. 

That often sounds like:

• I realize that the problem got this bad because I didn’t solve it at its root the first time. How can I avoid that behavior in the future?

• I’m coming into these interactions tired, which makes me impatient with everyone. How can I better recognize when I’m feeling that way?

3) The question often helps us identify the things we say we want or think we're supposed to want, versus those things we actually want. 

Colonna expanded on the “say you don’t want” part of the question: 

“...[T]here’s something oftentimes about the way in which we operate and the way we set up the conditions of our lives to be in unconscious service to us. The psychological term is secondary gain. But there are ways in which we find ourselves repeating patterns in our life. We always date the same type of person. We are always finding ourselves in the same kind of job. We’re always frustrated by the same sorts of [situations]. And so it’s really useful to sort of start to unpack that.”

Essentially, if we continually make decisions to get into, or to stay in, situations we say we don’t like, what unstated value are we getting out of it? (If you don’t like getting punched in the face, what is it about being a professional boxer that makes it worth it?)

That’s often a difficult reflection because it requires us to recognize deep motivations, some of which can be tough to admit.  

That reflection might sound like:

• I dislike how much pressure there is at my high-powered job, but it’s worth it to me because I like feeling powerful relative to others. 

• I’m exhausted by everything on my plate, but it’s a boost to my self-esteem to feel like I’m needed. 

Obviously, those are challenging thoughts to resolve, but recognizing them can give us a path forward. 

4) The question has just the right amount of hostile. 

The How are you complicit… question is just a tad more polite than asking How much of this is your fault? 

Because those questions are so close to each other, I don’t recommend asking How are you complicit… of your spouse or friend who’s just letting off steam at the end of the day and wants comfort and validation. 

I know from experience that it won’t end well. 

Even in my role as a coach, where I have license to challenge the client’s thinking, I generally preface that question with Can I ask you a provocative question? to help it go down easier.

But it’s precisely because the question is jarring and provocative that I find it one of the best self coaching questions we can ask ourselves. It can take us out of a place of comfort and the self-indulgent explanations of our challenges.

So try it out the next time you’re facing a daunting challenge. How have I been complicit in creating the conditions I say I don’t want?