Passages in Caregiving
Leaders & Managers
DropRegion · Lessons from Passages in Caregiving · Gail Sheehy

What Leaders/Managers Can Learn from Passages in Caregiving

Marcus took over a three-year systems migration in its exciting first month, when the team ran on adrenaline, late nights, and the thrill of building something new. He led that way for the whole project: constant urgency, daily war-room stand-ups, praise reserved for visible heroics. Eighteen months in, the work moved into a long, unglamorous maintenance stretch, fixing edge cases, supporting existing users, waiting on other teams. Marcus kept demanding the same wartime pace. His steadiest engineers, the ones actually keeping the system running, began transferring out quietly, one by one. He was blindsided in their exit interviews, insisting nothing had changed, when in fact almost everything about what the work required from him had.

01 · The Book in One Minute

The whole book, compressed

01Naming What Stage This Team
02Getting Help That Matches Where
03Preparing The Team
04Meaning In The Long Unglamorous

This edition works through 4 core lessons — take them one at a time, not all at once.

02 · Where Are You Now?

What's different for your conditions

Tap whichever ones sound like you. Nothing here is sent or saved — it's just for your own noticing.

Your team is the ongoing responsibility, and different members can be in different stages of the same effort at once, not one shared timeline.
Organizational systems, reviews, promotions, headcount, are often built for one stage and quietly punish behavior suited to another.
You are expected to project steadiness for others even while privately recognizing you're in over your head at a new stage.
Support for you as a leader usually has to be sought sideways or upward, from peers or your own manager, rather than offered automatically.
The ending of a leadership responsibility, a reorg, a handoff, stepping down, is rarely as clean as a project's official close date.

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03 · Core Lessons

The core lessons, applied to you

Naming What Stage This Team

Naming what stage this team or project is actually in

The idea

A launch stage rewards urgency and visible heroics. A maintenance stage rewards patience, quiet reliability, and recognition of unglamorous work that rarely gets applause. A crisis stage rewards decisive, transparent communication above all else. Leaders who keep running launch-stage energy through a maintenance stage exhaust the people who are actually sustaining the work, then wonder why steady performers start leaving for less demanding, better-recognized roles elsewhere.

What it looks like

A manager keeps calling emergency meetings and rewarding visible firefighting long after a project has settled into routine operation, training the team to manufacture crises for attention.

Try this

Ask your team directly, once a month, what stage they think the work is actually in, and compare their answer to yours.

Getting Help That Matches Where

Getting help that matches where you are, not where you started

The idea

Early in a role or project, a leader mostly needs information and validation that the plan is sound. Later, the same leader may need help managing burnout, navigating a layoff, or having a hard conversation about scope. Continuing to seek only tactical, how-to advice once you're facing a people or morale problem means missing what would actually help.

What it looks like

A manager brings a team-morale crisis to a project-management mentor and receives scheduling advice for a problem that is actually about trust.

Try this

Before asking for help, name the actual problem type, tactical, emotional, or political, out loud first.

Preparing The Team

Preparing the team, and yourself, for what's coming

The idea

It is tempting to assume the current team, budget, or momentum will hold steady. Leaders who prepare their people early for a coming transition, a reorg, a handoff, a slower season, reduce the shock when it arrives. Preparing honestly does not mean alarming people; it means naming likely changes plainly, before they become surprises that erode trust.

What it looks like

A leader hides a likely restructuring until it's announced, and the team's trust in every future update quietly erodes.

Try this

Identify one likely change in the next six months and mention it plainly in your next team update, even without full details.

Meaning In The Long Unglamorous

Meaning in the long unglamorous middle

The idea

It is easy to measure a leadership stint only by its final metrics, whether the project launched on time, whether the numbers hit target by the deadline. But most of what a leader actually builds, trust, a team's capability, a culture that survives your departure, forms during the long ordinary middle, not the launch or the closing report. Noticing that growth while it is happening, not only in a retrospective, is part of the job.

When the clusters compete

Preparing your team honestly for hard changes ahead can undercut the steady optimism a team needs to stay engaged day to day. Resolve this by separating audiences and timing: keep daily work focused and confident, while sharing honest, calibrated previews of likely change through smaller conversations or one-on-ones, so foresight does not have to come at the cost of morale.

04 · Choose Your Priority

Name one thing, honestly

What would you do differently this week if you admitted, honestly, which stage your team is actually in right now?


Good. Now look back at the "Try this" line under whichever lesson feels most connected to what you just wrote, and treat that as this week's actual assignment — not all 4 at once.

05 · Put It Into Practice

The practices from this edition

Ask your team directly, once a month, what stage they think the work is actually in, and compare their answer to yours.
Before asking for help, name the actual problem type, tactical, emotional, or political, out loud first.
Identify one likely change in the next six months and mention it plainly in your next team update, even without full details.

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06 · Small Experiment

Run this for seven days

Identify one likely change in the next six months and mention it plainly in your next team update, even without full details.

07 · Remember This
If you remember only 4 things
01Naming What Stage This Team. A launch stage rewards urgency and visible heroics.
02Getting Help That Matches Where. Early in a role or project, a leader mostly needs information and validation that the plan is sound.
03Preparing The Team. It is tempting to assume the current team, budget, or momentum will hold steady.
04Meaning In The Long Unglamorous. It is easy to measure a leadership stint only by its final metrics, whether the project launched on time, whether the numbers hit target by the deadline.
08 · Your Next Step

What will you do differently because you read this?

For a fuller picture of how a long responsibility for people changes shape over time, Gail Sheehy's Passages in Caregiving offers a framework worth adapting well beyond caregiving; if you are also navigating a parent's actual care, bring in a qualified doctor, counselor, or elder-law professional before any real decision.