I’ve been coaching women in leadership ranging from Director to C-Suite for a long time now. Over 200 sessions analysed, patterns noticed, and patterns confirmed. Across all of it, what I know to be true is that transformation rarely comes from a framework, a model, or a five-step plan.
It comes from a question that lands somewhere the person wasn’t expecting.
I had a client tell me, “Madeline, you deliver questions that rock you to your core in the nicest possible way”
That’s because the right question at the right moment doesn’t just make someone think differently about a situation. It makes them think differently about themselves. That’s where the real work is.
That’s what I mean when I say I activate women, not coach them.
These are five questions I come back to again and again. I’m sharing them here because I want you to sit with them. Don’t skim them. I know you are busy. I know it’s easier to keep pushing even if you are exhausted and even if you know you need to face yourself.
Actually sit with them.
See what comes up.
Because your answer will tell you something. Something real and true.
So here goes:
01. “What did you know to be true about yourself before the role, the organisation, the title got hold of you?”
This is the question I ask when someone has become so shaped by the environment they’re in that they’ve forgotten who walked through the door in the first place.
It happens more than people realise.
You join a company as someone bold, direct, and full of ideas. A few years of being subtly managed down, rewarded for compliance or overlooked for promotion, and you start to wonder if you imagined the bold version of yourself.
You didn’t.
She got squeezed out.
I’ve had women tell me that she’s gone; the women there were 10, 20 years ago. But here’s the good news – she didn’t leave. She’s still there, waiting. But you have to go back and find her before you can take her forward.
Sit with this one.
Before the career, before you learned what was rewarded and what wasn’t, what did you know yourself to be?
02. “Whose voice is that, really?”
When a woman sits across from me and starts explaining all the reasons why she can’t go for the role, ask for the pay rise, speak up in that meeting, or start the thing she’s been thinking about for three years, I listen carefully.
Not to the reasons; they aren’t really what’s going on. I listen to the voice delivering them.
Because nine times out of ten, that voice isn’t hers. It’s a parent, a manager who didn’t rate her and told her so, a system that was never built for her or even a culture that called her too much or not enough.
Guaranteed she inherited the voice and started using it as if it were her own.
The truth is – it’s not her voice.
It wasn’t an inheritance that she was supposed to accept.
The moment you can name whose voice it actually is, something shifts. You stop arguing with yourself and start seeing the real conversation that needs to happen.
Think about the thing you’ve been telling yourself you can’t do. Now ask yourself: whose voice is telling you that?
03. “What would you do if you already knew you were enough?”
I’ve worked with women who are extraordinary. Multiple degrees, twenty years of experience, high IQ’s, change-makers, transformational, with teams that would walk through walls for them and senior leaders who sing their praises.
Yet, they’re still waiting to feel ready.
Here’s what I’ve learned: the feeling of readiness doesn’t come first.
Action comes first.
Then confidence follows. Not the other way around.
And before the action – clarity.
Most people have this the wrong way round and spend years waiting for permission from others and themselves that’s never coming.
This question dismantles the loop.
It says: stop waiting. Assume you’re enough. Now what?
One of my clients, Michelle, was working until eleven at night most evenings, convinced that the hours were what was making her visible. When we lifted the lid on this, she shifted her belief when she stopped asking ‘when will I have done enough to deserve the recognition?’ and started asking ‘what does someone who already knows her worth actually do?’
She started stopping at six.
She still got the MVP.
If you already knew you were enough, what would you do differently this week?
04. “What are you tolerating that you’ve stopped noticing?”
Humans are remarkably good at adapting. Give someone a difficult enough environment for long enough, and they’ll find a way to function.
After a while, they start calling that functioning ‘fine’. You ask them how they are; ‘fine’ is the response. How are things going? ‘Fine.’
What’s actually happening is slow damage.
I ask this question because by the time most women reach me, they’ve adapted so thoroughly to what isn’t working that they can no longer see it clearly. The micromanaging boss has just become ‘how he is’. The all-male leadership team has become ‘just the reality here’. The Sunday evening dread has become ‘everyone feels like this’.
They haven’t.
And you shouldn’t have to either.
This is one of the most important questions in the Realigning stage of my work, because you cannot build clarity about what you actually want until you’ve gotten really honest about what you’ve been quietly accepting.
And yes, it’s quiet acceptance; it creeps, and before you know it, your standards have gone out the window.
What’s become wallpaper that you would never have accepted five years ago?
05. “Who benefits when you stay small?”
This one is more confrontational. I use it deliberately, and I use it at the right moment.
Because here’s the thing: playing safe, staying under the radar, not putting your hand up, not claiming the space you deserve, not challenging what needs to be challenged, none of that is neutral.
It’s like in sales: a sale always happens whether you get the sale or not because someone may have sold you their no.
Someone benefits from you playing small. Systems benefit from it; leaders who don’t want to be questioned benefit from it; cultures that rely on women to do more than they’re paid for benefit from it.
When you reframe shrinking as a structural choice that serves someone else’s agenda, rather than a personal failing, everything changes. The shame falls away, and the strategy becomes crucial and visible.
You’re not failing.
You’re playing a game whose rules were written by someone else, for someone else.
Not you!
Who in your world needs you to stay exactly where you are?
What comes next is up to you
These questions are the ones I return to because they work.
Because they’re honest.
Because they cause you to pause.
Because they make you question what’s really happening.
They go to the place most conversations skip over.
You can sit with them on your own and get real value from that. What I know from years of doing this work is that the real shift happens when you have someone in the room with you who won’t let you get away with a surface answer.
That’s what I do.
I activate the version of you that already has the answers. I just ask the questions that bring her forward.
If something in this has stirred something in you, I’d love to hear about it. Message me and tell me which question made you reconsider.
And if you’re ready to go deeper, the Circle of Brilliance Collective and my one-to-one Activation Access work are both spaces where this kind of work lives.
Come and find me.
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