The Examination
A Guided Set of Questions for Leaders Who Are Ready to Look
Most leadership development asks you to look outward. At your team, your strategy, your organization, your results. This piece asks you to look in the other direction.
Not as a therapeutic exercise. As a leadership one. The questions below are the ones that surface what’s actually been driving your leadership: the instincts, patterns, assumptions, and costs that don’t show up in a performance review but shape everything that does.
Work through them slowly. Write your answers down. The ones that make you want to move on quickly are usually the ones worth staying with longest.
Instincts
Your instincts were formed before your current role. They were shaped by the leaders who developed you, the environments that tested you, and the moments that taught you what leadership required. They’re running constantly, mostly below the surface.
Where did your leadership instincts come from? Who shaped them and do you still agree with what they taught you?
What do you do automatically under pressure that you’ve never consciously chosen to do?
When your instincts have been wrong, what was usually true about the situation? Is that pattern still present in how you lead today?
People
Every leader has a filter through which they assess capability, potential, and fit. Most of those filters were built in previous environments and never updated. What you assume about your team is not always what’s actually true about them.
What do you believe about your team’s capability that you’ve never directly tested?
Who on your team are you underinvesting in, and what assumption is driving that?
When you think someone isn’t ready for more responsibility, how much of that assessment is based on evidence and how much is based on pattern recognition from someone you’ve led before?
What would your team say you consistently get wrong about what they need from you?
Patterns
Patterns are the most honest data available. They offer a thread back to where things started to shift or take root. After each of these questions, the helpful next step is to ask: When did you first notice this?
What kind of problem do people consistently bring to you? What does that reveal about how they see you?
What do you consistently avoid? Not the things you delegate intentionally, but the ones you quietly let slide because engaging with them is uncomfortable.
What has someone told you more than once about how you lead that you haven’t fully acted on? What has kept you from acting on it?
When you are at your worst as a leader, what is usually true about the conditions around you?
Cost
Leadership requires expenditure. Most leaders track what the role produces. Very few track what it takes. The leaders who sustain their effectiveness over time are the ones who’ve done the accounting honestly.
What does your current role require of you that you are genuinely glad to give?
What does it require that you are giving anyway, at a cost you haven’t fully accounted for?
What have you stopped doing, saying, or being since you took this role? Was that loss necessary or was it just easier?
What would it cost you to lead more honestly from who you actually are?
What to do with what surfaces
Don’t try to act on everything at once. Pick one answer that surprised you and sit with it before you do anything with it. Share it with someone who knows you well enough to tell you whether it’s accurate.
The leaders who grow most consistently over time aren’t the ones with the best answers. They’re the ones who keep returning to the right questions.
This is the second exercise in the Vox Formation examination series. The first, Mapping Your Leadership Terrain, ran last week. Both are available to subscribers in the archive.
Good luck out there,
-Charlie