Before You Begin
Session Setup
Fill this in before the conversation starts. Internal only.
1
Section 1 · Opening
Grounding the Conversation
These are relational questions, not diagnostic. They signal what kind of conversation this will be. Let them land before moving forward.
◆ Ask
"Before we get into the formal questions — what made you say yes to coaching? Not the professional reason. The real one."
Probe if needed
"What were you hoping would be different after this?" · "Was there a specific moment that made you decide now?"
Listen For
The difference between their stated reason and the real one. A long pause often means the first response is not it. The moment they name — if they do — is usually the entry point.
What you are hearing
External trigger
Internal pull
Burnout / depletion
Life transition
Stuck — can't see past it
Seeking clarity
Relationship friction
Unexpected opportunity
Professional milestone
Accountability gap
Quick note
◆ Ask
"What would need to be true at the end of this engagement for you to say it was worth it? Not goals — what would feel different?"
Probe if needed
"When you say that — what does it look like on a Tuesday morning?" · "Is there someone who would notice that change? What would they see?"
Listen For
Whether the vision is behavioral, relational, or emotional. The category tells you where the work lives.
How they define success
Behavioral shift
Emotional freedom
Relational repair
Clarity about direction
More confidence
Less noise
Pace and sustainability
Being more themselves
Leadership presence
External recognition
Quick note
2
Section 2 · Values Architecture
What They Actually Live By
Bill George: the most effective leaders are distinguished not by the values they espouse but by the ones they return to under pressure. Surface what is operational, not aspirational.
◆ Ask
"Tell me about a decision you are genuinely proud of — not because of the outcome, but because of how you made it. What happened?"
Probe if needed
"What made that decision hard?" · "What would you have had to give up or risk to make it?"
Listen For
The value being protected in the story. Watch for: what they describe as the cost, who was affected, and what they were willing to trade.
Value being protected
Integrity
Courage
Care for others
Equity
Excellence
Boundaries
Loyalty
Vision
Honesty
Autonomy
Justice
Trust
Quick note
◆ Ask
"Now tell me about a moment when you knew — in the moment or afterward — that you didn't show up the way you wanted to. What was happening?"
Probe if needed
"What got in the way?" · "If you could go back, what would you do differently — and what would that have required of you?"
Listen For
The values gap — the conditions under which it appears. What kind of pressure, who was in the room, what was at stake. This is often where coaching lives.
Condition driving the gap
External pressure
Fear
Competing loyalties
Speed / pace
Isolation
Self-protection
Role demands
People-pleasing
Unexamined habit
Scarcity mindset
Quick note
Values Identification Exercise — Do This Together
Read aloud or share the screen. This is a collaborative exercise, not something you do for them.
1Say: "I'm going to read you a list of values. As I read each one, just say yes or no — whether it feels like it belongs to you. Don't overthink it." Read each value. Click those they claim.
2Then say: "Now look at the ones you selected. Which three feel most central — not aspirational, operational. The ones you'd defend." Click those gold.
3Finally: "Of those three — if you had to give all the others up and keep only one, which one?" Click it again to mark it deepest (mauve).
Selected
Core — top 3
Deepest — the one
No values selected yet
◆ Ask — After the Exercise
"You named [their value] as the one you'd keep. Help me understand what that looks like in practice for you — not the definition, but a moment when you were living it."
Probe if needed
"What does it cost you when you can't live that value at work?" · "When it conflicts with what the organization needs — what happens?"
Listen For
The embodied definition. Also listen for tension between the value and the demands of their role — that tension is often where the coaching begins.
Quality of their answer
Specific story
Abstract / general
Fully embodied
Aspirational only
Tension visible
Role conflict named
Practicing it now
Lost access to it
Quick note
3
Section 3 · Leadership Identity
How They Understand Themselves as a Leader
Kouzes and Posner: credibility requires self-knowledge, not self-presentation. These questions surface the leader's working model of themselves, which may or may not match how they are experienced.
◆ Ask
"What do you think you bring to a room — or a problem — that is distinctively yours? What do you do that other leaders don't, or can't, do as well?"
Probe if needed
"If your team could only keep one thing about how you lead, what would they choose?" · "When have you felt most like yourself as a leader?"
Listen For
Whether they describe relational, analytical, or operational strength. Heavy qualification of a strength often signals insecurity, not genuine humility.
How they describe their edge
Strategic thinking
Relational intelligence
Systems view
Visionary
Execution
Empathy
Directness
Steadiness
Creative problem-solving
Translating complexity
Holding the room
Heavily qualified it
Quick note
◆ Ask
"Tell me about a time you received feedback that was hard to hear. What did you do with it?"
Probe if needed
"Did you believe it was accurate? In the moment, or only later?" · "What would have made it easier to receive?"
Listen For
The relationship between stated openness and what they actually did with it. People who say they're open often describe dismissing feedback in the details of the story.
How they processed feedback
Accepted — acted on it
Accepted — took time
Deflected at first
Defensive
Never fully believed it
Transformed how they lead
Still unresolved
Minimized it
Quick note
◆ Ask
"If your team could tell you one thing — honestly — about how you affect them, and you couldn't explain or defend yourself, what do you think they would say?"
Probe if needed
"What would the person who struggles most with you say?" · "Has anyone ever told you something like that — even indirectly?"
Listen For
Leaders who know themselves answer specifically and without deflection. A quick generic answer is often a defense. A pause and a specific answer is usually the most honest one.
Self-awareness signal
Specific and unguarded
Paused before answering
Diplomatic / hedged
Generic / deflected
Surprised themselves
Named a pattern
Blind spot visible
Asked for your read
Quick note
◆ Ask
"What is the one thing you most want to change about how you lead? Not what you think you should want to change — the thing that, if it were different, would make you feel most like the leader you want to be."
Probe if needed
"How long have you known that about yourself?" · "What has kept that from changing so far?"
Listen For
The stated change — and the question "what has kept that from changing" is the beginning of the competing commitments conversation. Note it. It comes back in Section 4.
Nature of the desired change
Behavioral
Relational
Emotional regulation
Communication style
Decision-making
Delegation
Visibility
Boundaries
Trust-building
Slowing down
Taking up space
Quick note
4
Section 4 · Competing Commitments
What Might Be Working Against the Change
Kegan and Lahey: behind every stated commitment that isn't being kept is a competing commitment — something the leader is equally committed to protecting. Move slowly here. This is the most important and most tender territory.
◆ Ask
"You said you want to [their stated change]. I want to sit with that. What have you already tried? What happened when you tried?"
Probe if needed
"Was there a moment when you started to make the change and then pulled back? What were you protecting?" · "What did you tell yourself in that moment?"
Listen For
The pattern of the failed attempts — not just that they tried, but what derailed it each time. The recurring derailment is the competing commitment showing itself.
Pattern in failed attempts
Never fully started
Started — stopped
External barriers
Internal resistance
Recurring derailment
Needed permission
Got close — pulled back
Works / fades cycle
Quick note
◆ Ask
"I want to ask you something that might feel like a strange question. What would you lose if you made this change? What might you be protecting by keeping things the way they are?"
Probe if needed
"If you let go of [the behavior they want to change], what are you afraid would happen?" · "What would others think? What would you think of yourself?"
Listen For
The competing commitment is almost always a reasonable thing to protect. Your job is not to name it for them — it is to hold the space for them to find it. If they find it, it is theirs. If you hand it to them, it is yours.
What they are protecting
Safety
Control
Identity
Relationships
Status / credibility
Approval
Certainty
Not disappointing others
Being liked
Competence perception
Stability
Quick note
◆ Ask
"Where does that belief come from? Is there a moment — earlier in your career, or before — when you learned that lesson? When something happened that made that protection feel necessary?"
Probe if needed
"Did that belief ever serve you — was it the right lesson at the time?" · "Does it still apply now? Have the conditions changed?"
Listen For
The big assumption — the formative experience that made the competing commitment feel rational. If they share it, it is an act of trust. "Was it the right lesson at the time?" often opens the door for change more than any direct challenge would.
Origin of the belief
Formative story shared
Workplace origin
Early career origin
Childhood or family
Cultural / community
Unexamined — just true
Recognized in the moment
They challenged it themselves
Quick note
5
Section 5 · Context and Conditions
What They Are Working In and Working Through
Leadership does not happen in a vacuum. These questions are gentler — they are about the full person, not just the leader.
◆ Ask
"What is the hardest thing you are carrying right now — at work? Something that is genuinely taking up space."
Probe if needed
"Is that something you can affect, or something you're waiting out?" · "Who else knows how hard this is?"
Listen For
Whether the hard thing is external, relational, or internal. Also: whether they feel alone in it. Each points to a different coaching need.
Nature of the burden
External — can't control
Relational
Internal
Structural / systemic
Carrying it alone
Has support
Decision pending
Unresolved conflict
Quick note
◆ Ask
"Is there anything outside of work — in your life — that is affecting your capacity right now? You don't need to share anything you're not comfortable sharing. But if there's something I should know to support you well, I want to hold space for that."
Do not probe
Ask it once and let them choose. The invitation is enough.
Listen For
What they choose to share — and what they don't. If they share something significant, hold it with care and don't make it the center.
What they chose to share
Shared openly
Hinted — didn't name it
Said not relevant
Physical health
Family or caregiving
Grief or loss
Financial pressure
Relationship strain
Quick note
6
Section 6 · Behavior Observation
What You Are Noticing
This section is yours to complete — not theirs. Rate what you observed while they answered the questions above. 1 = Rarely evident · 5 = Consistently evident.
Complete during or immediately after the conversation. Rate based on what you observed, not what they said about themselves. Click again to deselect.
7
Section 7 · Closing
Landing the Session
End with something they can carry. The last question they answer before they leave sets the tone for everything that follows.
◆ Ask
"We've covered a lot of ground. Before we close — what is the one thing from this conversation you want to stay with? Not what you should focus on. The thing that's actually alive for you right now."
Do not probe
Let them sit with the question as long as they need to. The answer after a long pause is almost always the most important one.
Listen For
Whether they land on something internal, external, or relational. Where they land is where the first session should begin.
Where they landed
Internal — something about themselves
External — something to do
Relational
Surprised themselves
Named the competing commitment
The values work
Needs space to process
Ready to begin
Quick note
Your Observations — What You Want to Hold From This Conversation
Generate the Coaching Profile
The profile is built from your notes and selections. Complete at least a few sections before generating.
Leadership Coaching Profile
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Core Values — Named in Conversation
Proposed Session Focus — First Three Sessions
Coaching Profile — Plain Text