Dear Sonia,
I’ve been working with a coach for four months, and I don’t think anything is happening. We talk, I feel good for a day, then I go back to being the same person in the same meetings. Is coaching supposed to feel like this? Or am I doing it wrong?
Wondering if it’s me
Oh, my love. You’re not doing it wrong. But you might be having the wrong conversation.
Here’s the thing nobody says out loud about coaching: it is not advice. It is not a pep talk. It is not somebody clever telling you what to do while you nod and take notes you never read again. Coaching works because of questions. Good ones. The kind that land somewhere behind your sternum and sit there for three days until you finally have to do something about them.
I have been coaching leaders for close to twenty years now. Executives, founders, CEOs, and brand-new frontline managers who got promoted on a Friday and were terrified by Monday. And in all that time, the moments that changed people were rarely the moments I said something smart. They were the moments I asked something simple and then shut up.
So here they are. Seven of them. I’m giving them to you not as a party trick, but because I want you to be able to use them on yourself, and on the people you lead.
And I want to be really clear about why. These questions aren’t designed to expose you. They’re designed to hand you back something you’ve been quietly giving away: your own authority over your own life. Every one of them ends in the same place, which is you, deciding. Not your boss. Not your board. Not the version of you who’s been waiting for conditions to improve.
Fair warning: each of them asks something of you the moment you answer honestly. That’s not a sign they’re hurting you. That’s the sound of courage being used. It’s a muscle, not a personality trait, and this is exactly how you build it.
1. “What are you pretending not to know?”
This one still makes me sit up straighter. I was asked it years ago by a mentor who had the infuriating habit of being right. I was talking around a problem in my business — very articulately, I might add, and he waited for me to finish, then asked me that.
And I knew instantly. Of course I knew. I’d known for about eight months.
Here’s what’s remarkable about this question: it doesn’t ask you to work anything out. It assumes you already have. It just invites you to stop performing confusion. Because most of us aren’t stuck because we lack information. We’re stuck because acting on what we already know would be expensive. It would mean a hard conversation. A resignation. An apology. Admitting we were wrong in front of people, we’d rather stay impressive for.
So we manufacture uncertainty. We ask for one more piece of data. We say things like “I just need to think about it a bit more,” which is the most sophisticated form of avoidance ever invented by a competent person.
The good news buried in that? You are not lost. You are not lacking. You already have the answer. You’re just standing at the door of it, deciding whether to open it. And doors are much easier to open than answers are to find.
What it sounds like in the room: Silence. Then a long exhale. Then usually — “I know exactly what you’re asking.”
How to use it on yourself this week: Take the decision you’ve been circling for more than a month. Write down the answer you would give if you weren’t allowed to gather any more information. That’s not a guess. That’s the thing you’ve been pretending not to know. Now you’re one honest sentence ahead of where you were this morning.
2. “What’s the story you’re telling yourself, and what actually happened?”
This is the question that has saved more workplace relationships than any process, policy or performance framework I’ve ever seen.
Chris Argyris gave us the Ladder of Inference decades ago, and Brené Brown gave us the language most of us now use for it; the story I’m telling myself. It’s the same insight from two directions: we observe a tiny slice of what happened, then we climb, fast, into meaning. She didn’t reply to my email → she’s annoyed with me → she’s undermining me → I’m being pushed out.
We don’t experience that as a story. We experience it as reality. And then we lead from it, hire from it, avoid people because of it, and lose sleep over it.
My whole Courageous Conversation DOD™ approach is built on getting people back down that ladder to the ground floor: Direct Observational Data. What would a camera have recorded? No adjectives. No motives. No patterns. Just what happened.
“He’s dismissive in meetings” is a story. “In Tuesday’s meeting, I made a suggestion, and he moved to the next agenda item without responding” is data. You can have a real conversation about the second one. The first one just starts a war.
And here is why this question is so freeing, rather than so confronting: the story is the only part of this you can’t do anything about. The data, you can walk straight up to and ask about. Most of the weight people carry into my coaching room isn’t from what happened to them. It’s from what they decided it meant and then never checked. You are allowed to put that down. You’re allowed to put it down this week.
What it sounds like in the room: A client mid-sentence realising they have been furious for six weeks about something they never actually verified.
How to use it on yourself this week: Take the person you’re most frustrated with right now. Write two columns. What happened. What I made it mean. Then go and check the second column with them. It’s a horrible, brilliant, life-changing five minutes.
3. “What are you tolerating?”
I love this question because it goes hunting for the things that don’t announce themselves. We are all fairly good at handling crises. What we’re catastrophically bad at is noticing the low-grade, chronic, entirely fixable irritations we’ve simply decided to live with.
The meeting that shouldn’t exist. The team member whose behaviour everyone has quietly agreed to work around. The email you re-read every day and don’t answer. The role that stopped fitting you eighteen months ago. The system that adds forty minutes to every Thursday.
None of these will ever be urgent. That’s precisely the problem. Nothing that is merely annoying ever makes it onto a priority list — so it stays, and it drains, and you can’t work out why you’re so tired when nothing dramatic is happening.
When I ask leaders this, they usually name three things in about eleven seconds. Which tells you they’ve known all along. (See question one. These things are related.)
But notice what that speed actually means. It means the diagnosis is already done. Most of what’s exhausting you isn’t a great mystery requiring six months of reflection — it’s a short list of things you have permission to change and haven’t yet given yourself. That’s not a failing. That’s an opportunity sitting there with your name on it.
What it sounds like in the room: A list. A long one. Delivered slightly too quickly, with a laugh at the end that isn’t really a laugh.
How to use it on yourself this week: Write down ten things you’re tolerating. At work, at home, in your own head. Then circle the three that would take under an hour to eliminate. Do those three. The energy that comes back is genuinely disproportionate — and so is the confidence.
4. “And what else?”
The smallest question here. Possibly the most powerful. Michael Bungay Stanier calls it the AWE question in The Coaching Habit, and he’s right that it’s the best coaching question in the world, because it requires no cleverness at all. You just have to be willing to not fill the silence.
Here’s what happens. Someone tells you the problem. It’s a good, coherent, reasonable-sounding problem. You are now extremely tempted to solve it — because you’re a leader, and you got promoted for being good at solving things, and there is a genuine dopamine hit in being the person with the answer.
Don’t.
Ask “and what else?” instead. Then again. Then, if you can bear it, once more.
The first answer is the rehearsed answer. The second is the honest one. The third — the third is usually the actual thing. In my experience the real issue turns up on the third pass roughly nine times out of ten, and it’s almost never what walked through the door.
“The project’s behind.” And what else? “The team’s not communicating.” And what else? “…I don’t think I have the authority I was promised and I’m too embarrassed to say so.”
There it is. You would never have coached your way to that with advice. Use it on yourself, too. When you catch yourself explaining your own situation in a tidy paragraph you’ve clearly said before, that’s your cue. Ask yourself twice more. The tidy version is rarely the true one, and you cannot solve a problem you’re still describing politely.
What it sounds like in the room: Awkward. Genuinely. There’s a pause after the second one where both people feel it. Sit in it anyway.
How to use it this week: In your next one-on-one, ban yourself from offering a solution for the first ten minutes. Ask “and what else?” three times. Watch what surfaces.
5. “Whose permission are you waiting for?”
This is the one I wish someone had asked me a decade earlier, and it’s the reason I’ve put it on this list.
Almost every capable person I coach is holding at least one thing in a holding pattern, waiting for a signal that is never going to arrive. The nod from the executive. The restructure to settle. The right moment. The person who is finally going to say yes, you, now, go.
Ask them directly and they’ll tell you the wait is strategic. Sometimes it genuinely is. But far more often it’s the last respectable place for fear to hide, because “I’m waiting for the right time” sounds so much more professional than “I’m frightened, and if I don’t ask, no one can say no to me.”
Here’s the part that shifts things: in most cases nobody is actually withholding permission. There is no gatekeeper. There’s a vacancy — and you’ve been standing in front of it, politely queueing, for two years.
Sometimes the answer is a real person and a real conversation, and then your work is to go and have it this month rather than next quarter. But most of the time, when a leader traces it all the way back, the person whose permission they’re waiting for turns out to be themselves. That’s an extraordinary thing to discover, because it means the thing you thought was blocked was never locked.
What it sounds like in the room: A pause, then a slightly indignant laugh. Then, quietly: “…no one, actually.”
How to use it on yourself this week: Name the thing you’ve been waiting to be allowed to do. Write down exactly who has to say yes. If you can’t name a person, you already have your answer. If you can, book the conversation before you close your laptop today.
6. “Who do you need to be for this to change?”
This is the one that undoes people. Every other question on this list is about doing. This one is about being, and it’s the one that separates a nice conversation from an actual transformation.
Because you can hand someone a perfect action plan and they will not execute it — not because they’re lazy or unmotivated, but because the plan requires them to be a person they don’t yet believe they are.
The plan says to have the direct conversation. Being that person means being someone who can survive being disliked. The plan says to delegate the client work. Being that person means being someone whose worth isn’t measured by how indispensable they are. The plan says to put your hand up for the role. Being that person means being someone who doesn’t need permission first.
Marshall Goldsmith said what got you here won’t get you there. This is the mechanism. The behaviours that made you excellent — the over-preparing, the over-delivering, the being-the-one-who-holds-it-all — are identity, not habit. And identity doesn’t shift because you read a book about it.
I’ll tell you where I met this question personally. I built LeadershipHQ in 2008 after around forty job rejections as a sole parent, and for years afterwards I ran that business as someone who was still, quietly, proving something to those forty people. Every yes I said. Every rate I didn’t raise. Every boundary I didn’t hold.
Nothing changed when I got better at business. Things changed when I stopped being the woman who needed to be chosen.
And I want you to hear the hopeful half of that, because it’s the half people miss. If the block is identity rather than capability, then you were never inadequate. You were miscast. You’ve been running a version of yourself that made sense once and expired quietly some time ago. You are allowed to write the next one. People do it all the time, at forty, at fifty, at sixty-two, and it is never as late as it feels at 11pm.
What it sounds like in the room: Long silence. Sometimes tears. Almost always a completely different conversation afterwards.
How to use it on yourself this week: Name the change you’ve been failing to make. Then finish this sentence honestly: To do that, I’d have to be someone who is willing to… Whatever comes after that is your actual work — and it’s a far better use of you than another productivity system.
7. “What’s the bravest thing you could do before Friday?”
We finish here, and we finish here deliberately, because insight without movement is just a very expensive form of entertainment.
Notice the word bravest, not biggest. This isn’t a question about dramatic gestures. Courage in real leadership almost never looks cinematic. It looks like one sentence said out loud in a meeting where you’d normally stay quiet. One number named without apologising for it. One reply that says no. One phone call you’ve been rewriting in your head since March.
Here’s what I’ve watched happen for twenty years: courage compounds. People come to coaching believing they’ll act once they feel confident, and it runs precisely the other way round. You do the small brave thing, you survive it, and your nervous system quietly updates its file on what you can handle. Then the next one costs you less. Confidence is the residue of courage, not the prerequisite for it.
The deadline matters too. Give yourself a fortnight and you’ll spend it preparing. Give yourself until Friday and you’ll have to do the version that’s imperfect and real, which is the only version that ever changes anything.
What it sounds like in the room: A very fast answer, followed by “…but I couldn’t do that this week.” They can. They almost always do.
How to use it on yourself this week: One thing. Small enough to be genuinely achievable, brave enough that your stomach dropped slightly when you thought of it. Put it in your calendar with a time attached. Then tell one person you’re doing it, because we are all significantly braver when someone is going to ask us how it went.
What I want you to take from this
Back to you, my letter-writer. If coaching feels like it isn’t landing, my honest guess is that you’re being supported but not asked. Comfort is lovely. Comfort is not change. A good coach will be kind to you and will still ask you the question you were hoping to avoid — because they believe you’re capable of hearing it. That belief, not the technique, is what makes coaching work.
But you don’t need to wait for someone else to do it. Not one of these questions requires qualifications, a budget, or anyone’s approval. Every one of them works on yourself, in a notebook, on a Sunday, with a cup of tea and a bit of honesty.
And notice what they have in common. Not one of them is “What should I do?” Every single one assumes you already know something and that the work is having the courage to look at it and then move. That’s the whole game, really. Courage first. Clarity second. Action third. Always in that order, and never the other way around.
You are not four months of failed coaching. You are someone who noticed something wasn’t working and had the nerve to say so out loud — which, if we’re being accurate about it, is the exact skill this entire list is trying to build. You’ve already started.
Now go and ask yourself the one you flinched at. You know which one it was.
With love and a bit of fire, Sonia x
Want someone to ask you the hard ones? I coach executives, founders and new leaders through exactly this work — the questions, the identity shift, and the small brave things that change everything. If you’ve read this far and one of the seven is still sitting behind your sternum, that’s usually a sign it’s time. Book a conversation at https://soniamcdonald.com/
Bringing your people together this year? I speak to leadership teams and conferences on courage, human leadership and what it actually takes to change — First Comes Courage, Regulate to Lead and Human First Always. Rooms tend to leave with the questions above and the nerve to use them. Enquire at https://soniamcdonald.com/ or through Saxton Speakers Bureau.
Want the questions with you all week? Worksparks is my AI-powered leadership coaching platform — built on the same frameworks I use in the room, so you can bring the meeting you’re dreading or the conversation you’ve been avoiding to it at 6am on a Tuesday. A$29/month, with a 14-day free trial. Start at https://worksparks.com/
Got a question you’d rather not say out loud? Write to me. Every column starts with someone brave enough to ask. Send yours to sonia@soniamcdonald.com.au — always anonymous, always answered with love and a bit of fire.
