The Transformational Power of the Question: “Tell Me What I Need to Know”
In the noise of modern business - where every leader is told to be decisive, visionary, and unshakable - there’s a quieter skill that often gets overlooked: the art of listening.
But not just any listening.
The kind of listening that creates space for truth to emerge, even if it’s messy. The kind of listening that says, I trust there’s something here worth hearing, even if I don’t like it. The kind of listening that has the power to transform how you lead and what your business becomes.
It starts with seven simple words:
“Tell me what I need to know.”
Why Most Leaders Don’t Get the Truth
Most leaders think they’re open to feedback. They ask questions like:
How am I doing?
Is everything okay?
Any feedback for me?
But here’s the problem: these questions are designed to be polite, not to surface the truth. They create a power dynamic that keeps honesty at bay - because let’s face it, most people would rather nod along than risk conflict.
Even well-meaning questions like Does that make sense? or What do you think of the plan? still tilt the conversation in the direction of your ego, not their insight.
And when you’re only hearing what people think you want to hear, you’re missing the chance to see what really matters.
The Power of the Right Question
Tell me what I need to know is different. It’s an invitation, not a performance review.
It signals that you trust others have valuable perspective - insight that you can’t see on your own.
It removes your ego from the centre of the question, making it safer for people to share what’s real.
It opens the door to what’s messy, unpolished, and often the most valuable: the truth that might otherwise stay buried.
When you ask this question - and really mean it - everything shifts.
An honest conversation
How It Worked for Me
I learned this firsthand in my first week as CEO of Teach Starter. No agenda. No PowerPoint decks. Just one question, asked of every team member:
Tell me what I need to know.
What I heard wasn’t always comfortable. But it was real. And because it was real, it was actionable.
Patterns started to emerge. Critical issues surfaced - things that had been hidden under layers of politeness and habit. In just a few days, I saw the roadmap for what needed to change - and more importantly, I saw where alignment was missing.
That’s the power of this question. It doesn’t just gather facts - it reveals the invisible forces shaping your business.
How to Use It as a Leader
So when should you ask this question? Anytime you need to move beyond assumption and into insight:
When you join a new team or project
During 1:1s or team meetings
After a crisis or a big decision
When you can’t quite name what feels “off”
And who should you ask? Anyone who has a perspective you value:
Your leadership team
Managers and team members
Clients and customers
Advisors and partners
Listening for the Signal
Here’s where the real work begins: when you ask, trust what comes.
Even if it’s not what you expected.
Even if it’s hard to hear.
Even if it feels…random.
Because what someone chooses to share is a clue - about what’s top of mind for them, what they care about, and what they trust you with.
It’s your job as a leader to listen for the pattern, not just the words. To notice:
What’s repeated?
What’s left unsaid?
Where is the emotional energy - hope, frustration, excitement - pointing you?
What are the unintended consequences of what’s not working?
When you listen with curiosity instead of seeking validation, you’ll start to see the bigger picture. And that’s where transformation lives.
The Invitation
The next time you’re stuck - or you sense there’s more to the story - don’t ask for validation. Don’t ask for agreement.
Ask for insight.
Tell me what I need to know.
Then pause. Let the silence do its work. And trust that whatever emerges is exactly what you needed to hear.
Because that’s how you lead with clarity.
That’s how you build alignment that lasts.
And that’s how you create a business that grows - on truth, not assumption.