Beyond Doing: The Questions That Redefine Leadership.
When clients come to me for coaching, they often arrive with a clear goal: “I need to get better at emotional intelligence,” “I want to delegate more,” or “I need to stop coming across as too direct.” On the surface, it appears to be a request for behavioural change. But real change goes deeper.
As James Clear says, true behaviour change is identity change. How we see ourselves shapes what we do. Again and again, I see clients standing at the crossroads between the identity that got them here and the one that will carry them forward.
For many founders and entrepreneurs, this looks like an internal tug-of-war. The version of themselves that built the business is the one who worked tirelessly, controlled every outcome, and wore every hat. But what got them here, as Marshall Goldsmith says, won’t get them there. If they keep grinding at the same pace and holding on to every piece, they risk burning out, stalling the growth they crave, and losing the joy that once fuelled them.
Even in corporate settings, leaders who thrived by being the engine behind the team now need to step back, guide, and empower others to lead. They need to let go of the belief that their worth is tied to constant output and control.
And here is the fear that often surfaces quietly: Who am I if I am not this version of myself anymore?
This is where the work begins—not just in doing, but in questioning. The right questions help you step into a wiser, more spacious version of yourself. One who leads through clarity, not just urgency. One who fills their own tank before pouring into others. One who knows that true contribution isn’t measured by how much you do but by how you show up.
Below are questions inspired by Executive Coach Keith Leonard to guide you as you redefine leadership from the inside out, regardless of where you are in your journey. Let them invite you to pause, reflect, and allow the next version of yourself to emerge—not just for your growth, but for the people and the mission you’re here to serve.
Who Are You Becoming?
Don’t just ask, ‘What should I do?’ Ask, ‘Who am I being?’
If you were an imposter, would your results speak this loudly?
Who would you be if this current identity were no longer necessary?
What identity are you protecting, and what identity is trying to emerge?
If this new identity wasn’t about you building but about you becoming, what would it be called?
What would that version of you have to believe today in order to become real tomorrow?
What Are You Protecting?
You’re brilliant at protecting yourself. But:
What are you protecting that no longer needs protecting?
What part of yourself are you afraid will be lost if you stop operating the way you have?
What story are you living in that no longer reflects who you are?
What beliefs need to be redefined to support who you are becoming?
What fears come up when you imagine stepping into this new identity?
Redefining Your Value and Contribution.
What if your value has nothing to do with your output?
Contribution doesn’t mean emptying your energy bucket. What does sustainable service look like?
How can you shift from urgency to clarity?
What would clarity feel like if nothing in your external world changed?
What would become possible if your genius weren’t in the doing but in the designing?
What if you shifted your focus from perfection to contribution?
Letting Go Without Losing Yourself.
If you stepped away and went on vacation, would things fall apart?
What would happen if the company or team could thrive without you sitting in every meeting, pulling every lever?
What’s one area you could replace control with trust?
What's the cost of staying in control?
What would get exponentially better if you stopped holding on so tightly?
Delegating requires trust. Can you handle other people’s imperfections? Can you allow someone else to shine, even if it gets messy?
Navigating Fear and Growth.
Is this fear, or is this growth trying to emerge?
What is this fear inviting me to learn so I can grow?
Think about a moment of failure you’re afraid will happen. What would still be true about yourself after that moment?
If the part of you that’s trying to prove you’re enough is leading your company or team, what part of you could lead from purpose instead?
Moving from Urgency to Wisdom.
Are you making decisions from urgency or wisdom?
What’s one decision you could delay, delegate, or delete right now?
What’s the next tiny move that would feel doable right now?
What emotion are you avoiding by staying busy all the time?
What are you mistaking for urgency that might actually be avoidance?
Bringing It Back to Clarity.
What would bring clarity or relief to this chaos in the next 24 hours?
What’s one conversation you’re ready to have that you’ve been avoiding?
If this weren’t urgent, how would you approach it?
What’s the decision beneath the decision?
What would your future self thank you for doing in this moment?
Leading Yourself First.
How do you lead yourself in private?
What conversation do you need to have with yourself before having it with your team?
Where are you leaking energy right now? Where does it not need to go?
What distractions are you calling “strategy”?
What are three priorities you could put on hold right now?
The Legacy You’re Creating.
How do you empower others to lead after you’re gone?
What are you really here to leave behind?
What are you still building that doesn’t require your constant presence?
What version of leadership are you being called into next?
A Final Pause.
What do you know to be true about yourself, no matter what happens?
How do you want to show up, even here, even now?
Growth isn’t only found in what you achieve. It’s found in your willingness to ask better questions, to let go of what no longer needs protecting, and to lead from a place of clarity and wisdom, not adrenaline.
That is the version of leadership the world needs from you next.
Here’s to better questions,
Warm wishes,
Lori