Coaching Question of the Week
A weekly series exploring the questions that make coaching powerful — the kind that spark reflection, shift thinking, and open up better conversations. Each one is a question worth sitting with, drawn from real coaching practice and built to help leaders show up more curious and more present.
Where do you see yourself?
Visioning questions are so powerful because they help to explore what the future could look like.
What would "they" do in this situation?
It can be helpful to think of who would be valuable to explore different perspectives. This could be a mentor, customer, friend or family member. Sometimes we can be so deep in the situation that we aren’t able to step outside of it and look at it from a different angle.
What have you not yet explored?
Asking “What have we not yet explored” helps everyone jump out of the first viable solution and move into more creative problem solving.
Who else will benefit?
This question can help with that extra push to help someone achieve their goals knowing the impact it has on other people.
What difference will that make?
Asking “What difference will that make?” is a great way to halt the spinning and help the person look at the goal with a sharper frame of focus. Activity for its own sake is not always a good thing. This question can help people get at the “why” behind the action.
What actions feel right?
“What actions feel right” is such a great question because it helps move beyond logic and into accessing that gut feeling that is often telling us something important.
What would be interesting?
It's a great one to bring into a team when you're building commitment and buy-in. Asking what would be interesting opens up new ways to approach a problem — and often surfaces who's actually the right person to run with it.
How will you know when you have it?
Oftentimes, people come to a conversation with a lot on their mind, making it hard for us as leaders and coaches to determine what would be most helpful in that session.
What do you need to set aside for now?
When someone shows up to a coaching conversation with a lot going on in their lives they sometimes need to start with just getting it all off their chest. During the check in part of a coaching conversation they may just need to say it all out loud to someone.
What’s different this time?
When we fall into a pattern, it can be hard to see where circumstances are different. Maybe they’ve done something a hundred times before. But maybe they’re more tired today. Maybe the audience is different. Maybe the goals have changed slightly.
What is the most courageous thing you could try?
We love a good question that gets people thinking outside of the box. This question helps people get creative and innovative and consider things with no attachment to the outcome. It’s a simple yet effective way to have some fun and shake things up.
How will this help you grow?
Sometimes, we take action before we stop to think about why we’re doing it. This question, “how will this help you grow,” gets us to stop and think not just about why we’re doing what we are, but also what to focus on to get the most out of it.
What are some other ways you could achieve your goal?
Each time you ask this question, you’re opening up your team for expansive ideas generation. That way, when you’re ready to pick something to move forward with, you have options to choose from.
What do you need to let go of?
It sounds straightforward, but this question asks people to do something most avoid — look honestly at what's actually standing in the way. Sometimes it's a real structural barrier or resource gap, but often it's a mindset or a story they've been telling themselves that's running the show in the background.
What advice would your mentor give you?
We can all get stuck holding onto a certain perspective, we think “this is the way it is” because “this is the way I see it”. A question like “what advice would your mentor give you” helps someone detach from their current viewpoint and get outside of themselves.
If there were no limits, what would you do?
It’s incredible to see what happens when you remove all of the limits, all of the constraints on a problem and see the creative ways your team will come up with solutions.
What if this were 10x more successful than you thought?
What assumptions are you putting on either your goals or the goals of your team?
What strengths do you have that you could apply here?
We see this so often, when someone is in their element, they’re more likely to take action and feel good doing it.
What assumptions have you made?
We get on a track — the thinking feels logical, the direction feels obvious — and nobody stops to ask what's actually underneath it. What assumptions are we basing it on? This question comes in from the side and asks someone to make their assumptions explicit. Not to tear them down or to necessarily change course, just to see them clearly.
What are the benefits of achieving this goal?
Most people skip straight to the how. The goal gets set, the plan gets built, and everyone jumps into execution mode. And that energy is great but it skips something important.