What Color Is Your Parachute
Leaders & Managers
DropRegion · Lessons from What Color Is Your Parachute · Richard Bolles

What Leaders and Managers Can Learn from What Color Is Your Parachute

You're not job hunting, but you're probably stuck in the same rut this book was written to fix: waiting for the next role to be posted internally, or assuming your path forward means doing more of what you already do. Leaders often treat their next move — a promotion, a lateral shift, a new challenge — as something that will simply appear if they perform well, instead of something they can actively shape by knowing what they want and talking to the right people. The book's ideas apply just as well to moving inside an organization as to leaving one.

01 · The Book in One Minute

The whole book, compressed

01Question Whether Your Current Lane
02Have Real Conversations With People
03Make The Case
04Keep Re-examining What You Want

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 next move is often invisible until it's announced, unlike an external posting you can see and react to.
You have internal relationships already, but may never have used them to explore beyond your current lane.
Advocating for yourself can feel at odds with a leadership identity built around advocating for others.
Your team watches how you handle your own career, whether you intend that or not.
Politics and structure matter more here than in an open job market — visibility and trust matter as much as skill.

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03 · Core Lessons

The core lessons, applied to you

Question Whether Your Current Lane

Question whether your current lane is really the only one that fits you

The idea

Many leaders assume their next step must extend their current function, without ever checking whether their real strengths and interests point somewhere else in the organization.

What it looks like

A strong operations manager gets nudged toward a bigger operations role every cycle, never mentions that the part of the job she loves most is mentoring junior staff, and ends up leading a larger team doing work that drains her.

Try this

List the three parts of your current role that energize you most and the three that drain you, then check whether your assumed next role has more of the first list or the second.

Have Real Conversations With People

Have real conversations with people doing the work you're curious about, before a role opens

The idea

Waiting for a posting means competing for a role once it's already visible to everyone; a conversation with someone doing that work months earlier tells you what the role really involves and puts your name in the room before it's a competition.

What it looks like

A manager waits quietly for a director role to open, assumes seniority will carry the decision, and is blindsided when someone who spent the past year having informal conversations with the hiring committee gets the nod instead.

Try this

Pick one function or leader you're curious about and set up one genuine conversation this month — not to ask for anything, just to understand their world.

Make The Case

Make the case for what problem you'd solve, not just your track record

The idea

A resume of accomplishments tells people what you've done; naming the specific problem you'd solve for them next tells people what you're for.

What it looks like

A manager pitches herself for a stretch role using a list of past wins, and the decision-maker, who is trying to solve a specific gap on his team, can't tell if she's even aware the gap exists.

Try this

Before your next internal pitch, write one paragraph naming the specific problem the team or role is facing and how your particular strengths address it — lead with that, not your resume.

Keep Re-examining What You Want

Keep re-examining what you want as your role and organization change

The idea

What energized you two roles ago may not energize you now — treating your fit with your current position as something worth periodically re-checking, rather than settling it once, keeps you from drifting into a role that no longer suits you.

When the clusters compete

Being curious about other paths can look like disloyalty if you're not careful; keep your exploration conversations low-key and framed as learning, and stay visibly committed to your current team's success while you do it.

04 · Choose Your Priority

Name one thing, honestly

If no one else were watching or judging the choice, what kind of work would you actually want to be doing a year from 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

List the three parts of your current role that energize you most and the three that drain you, then check whether your assumed next role has more of the first list or the second.
Pick one function or leader you're curious about and set up one genuine conversation this month — not to ask for anything, just to understand their world.
Before your next internal pitch, write one paragraph naming the specific problem the team or role is facing and how your particular strengths address it — lead with that, not your resume.

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06 · Small Experiment

Run this for seven days

Before your next internal pitch, write one paragraph naming the specific problem the team or role is facing and how your particular strengths address it — lead with that, not your resume.

07 · Remember This
If you remember only 4 things
01Question Whether Your Current Lane. Many leaders assume their next step must extend their current function, without ever checking whether their real strengths and interests point somewhere else in the organization.
02Have Real Conversations With People. Waiting for a posting means competing for a role once it's already visible to everyone; a conversation with someone doing that work months earlier tells you what the role really involves and puts your name in the room before it's a competition.
03Make The Case. A resume of accomplishments tells people what you've done; naming the specific problem you'd solve for them next tells people what you're for.
04Keep Re-examining What You Want. What energized you two roles ago may not energize you now — treating your fit with your current position as something worth periodically re-checking, rather than settling it once, keeps you from drifting into a role that no longer suits you.
08 · Your Next Step

What will you do differently because you read this?

For the deeper framework behind clarifying your strengths, reaching out directly, and pitching yourself around a specific problem, read Richard Bolles's original book, What Color Is Your Parachute.