10 Self-Coaching Questions to Get Unstuck

A few days ago I got an email from a brand new coaching client of mine. We hadn’t even had our first call together and she asked an interesting question:

Is there anything I can reflect on ahead of time to make our work together more productive?

I loved the question—mostly because it showed a lot of initiative and agency in a process that often elicits dependency and passivity.

I responded with a handful of questions. But writing the email to her prompted a funny hypothetical question in my head:

What if the only way to coach someone was to pose a series of questions—one question per week—to help them coach themselves through their current struggles?

In other words, if I knew nothing else about someone other than that they felt stuck in some aspect of their life, what questions would I ask to help them get unstuck?

I came up with 10 and they’re a mixture of questions I’ve heard from other coaches and mentors, questions I’ve developed myself as a coach, and a few that just came to me as I was writing this:

Are you running away from a problem or toward a solution? Outside of legitimately dangerous situations, fear-based motivation is usually counterproductive long-term.
If you hired a good friend to be the CEO of your life, what’s the first thing they would change? The real answer is usually so boring and obvious we overlook it.
What does good stress look like for you? When we’re stuck, we often need more challenge in our lives, not less.
Which part of your personality is in charge most often? Which part should be in charge more often? Self-leadership sometimes means firing your current CEO and promoting someone else.
What hard conversations are you avoiding? I’d say that in at least 40% of my work as a coach and consultant, the main bottleneck to progress is avoidance of hard conversations.
What would your ten-year-old self be most disappointed with you for? I find this question much more useful than its more popular sibling: What will you most regret about your life on your deathbed?
When was the last time you felt deeply proud of yourself? Pride might be the most underrated emotion.
How are you maintaining the problems you want to overcome? Self-sabotage comes in many shapes and sizes.
Which person in your life would you benefit most from spending more time with? Personal growth is almost always social growth.
Which person in your life would benefit most from spending more time with you? Ironically, we often stay stuck because we’re too focused on getting ourselves unstuck instead of asking how we can help others get unstuck.

Obviously, you can use these however you want. But if you’re intrigued and want to go a little deeper, try this: For the next ten days, carve out ten minutes per day, and free write or journal about each of these questions.

90% of good coaching is asking the right question at the right moment. And while having an outside person to ask you the questions can be helpful, there’s no reason you can’t ask them of yourself.