7 Powerful Coaching Questions
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Now, onto Issue 10.
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Today’s Issue
If we have any desire to help people get better in life — as parents, friends, managers, leaders, coaches, teachers, mentors or anything else — we need coaching skills.
Today, we’re going to learn the 7 most powerful coaching questions.
You can start applying these in your next conversation, and they’ll instantly make you a better leader.
Let’s dive in.
The 7 most powerful coaching questions
Inc
You’re a coach to someone in your life.
Whether you realize it or not, you play a role in someone’s development and growth.
This could be at work, on a sports team, in your family, in your community, in your group of friends.
Everyone coaches someone.
And if you care about helping the people in your life be their best — which I assume you do, if you’re reading this newsletter — then coaching skills are essential.
So, in the next few minutes, I want to help you build foundational coaching skills that you can immediately apply.
In his book “The Coaching Habit,” Michael Bungay Stanier lays out a series of 7 questions.
It’s the simplest and most powerful framework of coaching questions I’ve found.
They can be used in any leadership, management or development conversation you may have.
Here are the 7 questions and what makes them powerful.
1. “What’s on your mind?”
This is the Kickstart Question.
It’s designed to open up a dialogue about something impactful.
It’s casual enough to not be intimidating, yet forceful enough to initiate a meaningful conversation immediately.
Why it’s powerful:
The Kickstart Question is open-ended yet focused.
It gives the person you’re speaking with the autonomy to decide how to start the conversation, yet with guardrails.
It implies, “Tell me what’s exciting you, giving you anxiety or consuming your attention at this moment.”
It’s not an invitation to ramble or give you a vanilla update.
Skip “how are you?” or some other hollow small talk.
Start your coaching conversations with, “What’s on your mind?”
2. “And what else?”
This is the Awe Question.
This question is designed to go beneath the surface.
To get past default responses.
To get to the thing that’s truly critical.
Why it’s powerful:
Don’t be fooled by the simplicity of this question.
This question drives additional insight, discovery and self-awareness in an effortless way.
Just as important, it protects us (the coach) from giving into the human nature of giving advice.
Most managers and leaders hear a challenge from their people and launch into problem-solving mode. They want to “fix” it.
But that’s almost always the wrong call.
“And what else?” keeps you curious.
It keeps the conversation in discovery mode.
It’s a shovel that keeps digging up gold to be mined.
In addition to managing our desire to give advice, it buys us time to think.
Practice asking this question multiple times in a conversation before moving to the next stage (3 times is a good target).
You’ll be stunned to see how often the first response to “what’s on your mind?” is actually NOT the most important issue at hand.
3. “What’s the real challenge here for you?”
This is the Focus Question.
The purpose is to get to the heart of the issue and opportunity for growth.
Why it’s powerful:
When people begin talking about a problem, it’s rarely the primary problem.
They’re describing details, and it’s your job to get to the root.
This question is powerful for two reasons.
The words “real challenge” ensures you get to the right problem, not just any problem.
The words “for you” brings the conversation from the abstract back to the individual.
This is critical.
We can only coach the person we’re talking to, not somebody (or something) else.
To do that, we need to help them stop focusing on others and start focusing on themselves.
This question hones in on a meaningful problem and puts the focus on the person you’re coaching.
You’re now positioned to go a level deeper.
4. “What do you want?”
This is the Foundation Question.
It’s intended to reveal an individual’s desired outcome.
But there are surface-level desires, and then deep-rooted human desires.
This question opens the door to get to the latter.
Why it’s powerful:
Asking “what do you want” does two things.
It creates psychological safety and autonomy.
This question positions you on the same team as the person you’re coaching. It creates a feeling that you’re “in it” with them.
It also empowers them to choose the destination of this conversation.
This question is also a transition.
We’re now moving from reflecting, analyzing and dissecting into action.
We’re establish a target to move towards.
In order to have a productive conversation, we need to get the true “want” on the table.
5. “How can I help?”
This is the Lazy Question.
It’s intended to put the onus on the other person to take ownership of what happens next.
Why it’s powerful:
This question is powerful for two reasons:
It forces the person to make a direct and clear request
It stops you from thinking you know how to best help
Just like “and what else?” prevents us from giving advice, “how can I help?” prevents us from going straight to taking action before we truly know what action to take.
Once you ask this question and get the request, you have a few ways you can respond:
Yes, I can do that
No, I can’t do that
I can’t do that, but I could do this
I’m not sure - let me think about that
You are not automatically obligated to do the thing being asked of you.
Our goal is just to get clear on what the request actually is so we can move to the next step in the conversation.
6. “If you’re saying yes to this, what are you saying no to?”
This is the Strategic Question.
It’s intended to force focus and prioritization.
Why it’s powerful:
None of us have unlimited resources.
Money, time, attention, energy.
We can’t spend them on everything at the same time. We must make choices and tradeoffs.
With this question, we’re asking the person to be clear and committed to what they say yes to.
We’re also forcing an accompanying “no.”
There are two types of no’s - the no of omission and the no of commission.
The no of omission applies to options that are automatically eliminated by saying yes to something (eg. if you go to the game at 1pm, you can’t also go to the beach at 1pm).
The no of commission is what you NEED to say no to in order to commit to the yes.
This could be things like projects, relationships, habits or old beliefs that are taking up space.
Every “yes” needs the boundary of a “no.”
7. “What was most useful for you?”
This is the Learning Question.
It’s intended to give you critical insight into how you can continue helping this person develop.
Why it’s powerful:
People don’t learn when they tell you something.
They don’t even really learn when they do something.
They start learning and creating new neural pathways only when they have the chance to recall and reflect on what just occurred.
So near the end of every coaching conversation, ask this question.
It creates a learning moment by reinforcing key insights and takeaways.
This is what solidifies the “aha” moments in the conversation.
If you want learning to “stick,” create space for people to reflect and recall key learnings at the end of the conversation.
Summary
Let’s recap the 7 most powerful coaching questions:
What’s on your mind?
And what else?
What’s the real challenge here for you?
What do you want?
How can I help?
If you’re saying yes to this, what are you saying no to?
What was most useful for you?
You don’t have to use all of these in every conversation, or necessarily use them in this order.
But I’d highly suggest adopting them as your general coaching framework and working them in as much as possible.
If you remember nothing else, remember this:
It’s human nature to give advice.
Practice NOT giving advice when people ask for it.
The best way to help someone develop is almost always by asking questions and helping them come up with their own answers.
(P.S. Read The Coaching Habit if you want to go deeper on this framework. It’s excellent.
Teddy’s Recommendations
A few things I found interesting this week:
This Wall Street Journal deep dive on FTX founder Sam Bankman-Fried and the mess at FTX has a lot of lessons in it for anyone building or leading a company. Wild story.
My friend Sieva Kozinsky is a big library guy and dug up a cool list of free library resources that will save you money.
I’ve been rereading Tim Ferriss’ 4-Hour Workweek. I don’t really believe in the general concept (at least not when you’re in the early stages of building something), but Tim’s perspective on separating time from income and creating leverage in our lives is sharp. It’s worth thinking about how you can apply those concepts in a way that makes sense for you.
I’d love to hear from you
What’s your biggest takeaway from this issue?
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Thanks for reading.
See you next Sunday.
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