Coaching Questions for Leaders – November 17, 2020
- Carol Pfeiffer

- Nov 17, 2020
- 5 min read

Asking good questions is what I do for a living and I’m passionate about it, because asking the right question at the right moment can help someone break through old patterns and approach their situation in a powerful new way. In the coaching world, we call these “curious” or “powerful” questions.
But asking powerful questions isn’t something only a coach can do: it is a critical skill that leaders can develop. The key in your role as leader is to coach and develop your team to think for themselves and solve their own problems. Your job is to identify and draw out their natural talents and instincts, and to invite them to be part of the process rather than a bystander.
Asking curious questions is a great way to do that.
Leaders Don’t Need to Know all the Answers
I recently had a conversation with a client who was preparing to step into a new leadership role. She expressed some fear and reticence about diving into challenging conversations with her new team. She was worried about feeling like she needed to know all the answers.
This is a common misperception for leaders at any level, and it causes leaders to feel a lot of pressure and in some cases, end up making poor decisions. The truth is that leaders do not need to know all the answers, nor should they have all the answers (how disengaging is that for the team??). Leaders need to know how to ask curious questions of their team members so that, together, they can come up with the best solution.
I reminded my client that the whole point of having a team of people reporting to her is so that she can leverage their knowledge. These are people who are smart, they want to contribute, and they have a wealth of information and insight into their areas of expertise. If you dictate to a team like this, you will shut them down. Instead, engage them! Ask questions. Facilitate intelligent conversations that lead to solutions.
That is the whole point of putting together teams.
Take the “Coach Approach”
In your work with your team, I invite you to take on a “coach approach,” and embrace the power of asking curious questions to support team members in thinking for themselves rather than waiting to be instructed. It will help you build a team of people who know how to solve problems on their own and feel empowered to take initiative.
According to PositivePsychology.com, the most powerful questions have the following qualities:
They generate curiosity in the listener
Stimulate reflective conversation
Surface underlying and new possibilities
Generate energy and forward movement
Channel attention and focused inquiry
Touch on a deeper meaning
Evoke more questions
Travel well
Stick with participants
And are thought-provoking
The Right Kinds of Questions
Most of us learn the difference between open-ended and yes/no questions in fourth grade, but we forget what a big difference it can make to change a yes/no question into a what/how question. Effective questions encourage the other person to reflect and elaborate; asking questions such as, “What’s important about what you learned today?” or “How will you apply what you learned today?” open up a chance for real insights to emerge. On the other hand, asking a closed ended question such as, “Did you learn anything today?” shuts down the conversation.
I also suggest staying away from asking solution-oriented questions, at least in the beginning of the conversation. If your team jumps into finding a solution right away, before first talking through and pinpointing what, exactly, is the right problem to solve, you may find that the solution you land on addresses the wrong problem (or is actually just a Band-Aid).
Questions to Get You Started
Here are some of my favorite coaching questions to help you engage your team members in a more powerful way.
What can we celebrate today?I ask this of all my coaching clients at the beginning of the call. It’s amazing to witness even the most down-on-their-luck person perk up when they’re asked about their “wins.” Guiding the conversation in a positive direction from the beginning can change the course of the entire discussion, for the better. Often, our mindset will shift into the mode of seeing what’s possible instead of getting stuck in what can’t be done or what’s hard.
What choice do you want to make?
Sometimes we feel like we don’t have any options, but we always have choices to make, whether they’re small (like whether or not to attend a meeting) or they’re big (like choosing whether to leave a job). I like to help people shift their language from “I have to” or “I should” into “I choose to” and “I get to.”
What is keeping you stuck?
There’s always a benefit in staying stuck, or else we wouldn’t let it happen. If I decide not to lose twenty pounds, the benefit is that I get to keep eating Cheetos! If I stay in a toxic work environment, no matter how bad it gets, the benefit is that I don’t have go through the challenging process of finding another job. In every choice we make, there is a benefit. Being able to see the benefit in a “stuck” situation can be enlightening.
What would be better or different?
In my work with clients, I always try to help them connect to the change that they’re ultimately attempting to bring about. If someone tells me they hate their job, my question is, “What would be better if you changed jobs?” They might say, “Well, I won’t dread Sunday nights because I’ll actually look forward to work on Monday. I might not have such a short fuse with my kids every night.” If you were to achieve your goal, to make the change you really want to make, get really clear about what would be better or different. Grounding yourself in your “why” can be incredibly motivating to help you move forward.
Five years from now, what will you wish you had done today?
I ask myself a similar question every day. “What would my 55-year-old self want me to do today?” The answer is usually something like go for a walk, spend time with my son, or eat my veggies. This is my most favorite question because it generates such a clear answer: your future self with either thank you for an activity… or not!
Asking powerful questions of yourself and of others can be a game-changer. If you’d like support in building and developing this skillset, contact me today.
Photo Source: CarlyAnderson.com




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