LEADERSHIP COACHING
A place to think clearly when the stakes are high
Practical, confidential coaching for CEOs, founders, and other senior executives navigating consequential decisions, high-stakes conversations, and the patterns that emerge under pressure.
At the senior level, the hardest challenges rarely belong to just one part of the business. A decision about a person may also affect performance, culture, investor confidence, and the management team’s ability to operate without your intervention.
You may have smart people around you and still lack a place to examine the situation candidly. Some concerns cannot easily be worked through with an employee, colleague, board member, or investor.
Coaching provides a place to slow the situation down, question your assumptions, consider perspectives you may be missing, and determine how you want to proceed.
When coaching can be useful
Senior executives often turn to coaching when:
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Too many consequential decisions continue to make their way back to them
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A capable management team is not operating with the judgment or independence the company now requires
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They face a decision with legitimate competing concerns and no clean answer
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They are preparing for a high-stakes conversation with an employee, partner, board member, or investor
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The leadership habits that helped build the company are becoming less effective as it grows
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Pressure is making them more controlling, avoidant, reactive, or certain than they intend to be
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They want a candid thinking partner who is outside the organization and has no stake in its internal politics
The goal is not to provide generic advice or turn you into someone else. It is to help you see the situation more clearly, expand your choices, and act with greater intention.
Coaching grounded in the Middle Path
The Middle Path is central to how I approach coaching—and to the management-development workshops I teach.
Coaching does not follow a predetermined curriculum. The work begins with the decision, conversation, responsibility, or recurring pattern that deserves your attention.
Middle Path principles help us look beyond the first explanation, question apparent either-or choices, and consider the individual, relational, and structural forces at work.
Senior executives regularly encounter tensions such as:
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Holding people accountable while remaining supportive
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Moving quickly while involving the right people
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Producing business results while operating with integrity
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Retaining appropriate control while giving others meaningful authority
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Speaking candidly while protecting an important relationship
The Middle Path is not about splitting the difference. It is about identifying the legitimate concerns on both sides and finding a more integrated response.
A practical reference for Middle Path thinking
The table below summarizes several principles that frequently inform my coaching and workshops. We draw on them when they help illuminate the situation—not because there is a prescribed sequence to follow.
You may recognize yourself leaning toward one side or the other depending on the circumstances. The aim is not perfect balance. It is to notice when an apparent choice is narrowing your thinking—and recover the concerns that matter on both sides.
What working together looks like
Our conversations remain connected to real work. You may leave with a conversation to conduct, an assumption to test, or a different approach to try. When we meet again, we examine what happened, what you learned, and what the situation now calls for.
I will offer questions, observations, frameworks, and candid feedback. You remain responsible for deciding what fits your situation and what you will do next.
A structured engagement—with room to adapt
I typically structure coaching in seven-hour blocks. A block gives us enough time to establish a meaningful focus, apply the work to real situations, and determine whether continued coaching would provide enough value to warrant another block—without requiring an open-ended commitment.
Executive coaching begins with Hogan
For executive coaching, the first block includes the full Hogan Leadership Assessment suite, a two-hour initial session devoted largely to interpreting the results, and five additional one-hour coaching sessions.
The Hogan assessments provide insights into:
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How others are likely to experience you from day to day
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The blind spots and patterns that may derail your effectiveness under pressure
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The values and motivations that influence your decisions
Hogan does not provide a verdict or prescribe a development plan. It gives us a rigorous starting point for examining patterns in how you lead.
Subsequent blocks of coaching consist of seven one-hour sessions and continue the work where it is producing the greatest value.
Coaching is also available for mid-level managers and others with significant responsibility. In those situations, the starting point and structure are adapted to the leader and the work in front of them.
Using Hogan for hiring or promotion? Learn about Hogan for executive selection.
Coaching one person—or strengthening the management system?
Sometimes the challenge sits primarily with one executive or manager: a consequential decision, a high-stakes conversation, a transition, or a recurring pattern.
At other times, the same problems appear across a management team. Coaching one person may help, but the larger management system may also deserve attention.
When a company wants to strengthen an entire management team, I generally begin by looking at that larger system rather than coaching people in isolation.