Stopover Leadership Development · Coaching Practice

A place to think the decision through.

A place to think through the situations that won’t resolve on their own. Real conversations. Specific next steps. Judgment that gets steadier over time.

Book a 20-minute call →
What leaders carry into this work

There comes a point in every leadership career where something stops moving. The thinking isn’t getting easier. The team can’t help. You need a room where the only job is to think with you.

  • "A decision has been circling for months. I can’t close it."
  • "A team tension keeps resurfacing. I keep starting from scratch on it."
  • "A program or direction no longer fits the reality of where we are."
  • "I want a second opinion. From someone who isn’t on staff or the board."

Bring the situation. Take the step. Watch what moves.

What it is

A thinking relationship, not a program.

In each session you bring a real situation from your work. Together we examine what’s happening, the pressures around it, and the leadership responsibility that sits with you. Through careful questions, reflection, and occasional challenge, the goal is to reach the leadership judgment the situation requires.

Each session ends with one practical step. Between sessions, your job is to take it and notice what happens. Over six months, situations that once felt stuck begin to move. Decisions become clearer. Leadership becomes steadier and more deliberate.

How it works
1

Map the landscape.

Session 1, often a walk. Map the pressure landscape and set the six-month arc.

2

Name the focus.

Session 2. Two or three focus areas, desired outcomes, and your accountability mirror.

3

Work the situations.

Sessions 3 through 23. Real decisions, real tensions, specific next steps from each session.

4

Read the arc.

Session 24. What changed, what you learned, what carries forward.

What you leave with

Steadier judgment. Decisions that close.

  • A named six-month arc. A clear picture of where you’re going and what a meaningful shift looks like.
  • A live read on the pressure pattern running in your system right now. And what to do about it.
  • A working record of the decisions you made. The Coaching Progress Tracker holds the thread, session to session.
  • An accountability mirror. One person inside your organization who watches for shifts and tells you what they see.
  • A discipline that outlasts the engagement. The thinking pattern keeps working after we stop.
What it costs
$500 / month
Nonprofit & charitable-sector leaders

Four hours of coaching per month over a six-month engagement. In person, by phone, or video.

$645 / month
All other leaders

Same engagement. Same time commitment. Different audience.

On confidentiality. What we discuss stays in the room. Details of our conversations are not shared with anyone inside or outside your organization.
Begin

Ready for a partner to support your work?

Book a 20-minute call →
En route, but aren’t we all.