Anybody can write a name down. That’s not a plan.
What does make a good succession plan?
It’s a question we find ourselves asking more and more as we grapple with all the change (planned and unplanned) that can happen over decades-long relationships. The reality is that we’ve had mixed results in succession planning ourselves, both at our portfolio companies and here at Permanent Equity.
On paper, it seems like choosing a successor, getting them ready, and setting them up for success should be straightforward (not to say easy). A quick google search will beam you any number of 5- or 7- or 17-step guides to succession planning you could want.
And yet. Succession has lackluster rates of success everywhere from mega-corporations to small, family-run businesses. Despite the plethora of advice about getting it right, the chances of actually doing so seem vanishingly small. Why? “On paper” doesn’t generally account for the fact that people are messy. Retirements, promotions, hirings – changes that seem neat on an org. chart – run into emotions, ego, relationships, and identities once they move off paper and into the real world.
So, we’re on a mission to find out not only what works and what doesn’t in succession planning, what elements are needed in a good plan, who should be responsible for it, and what it should look like, but also the motivations, incentives, and interactions that can send the best plans sideways.
In short, this project is a living documentation of what we know and don’t know about succession planning and the people involved. It’s not meant to be exhaustive, but it’s an ongoing collection of questions we’ve asked, methods we’ve seen, tools to help plan, and considerations to take into account – our FAQ for succession planning.
In these installments, you’ll find one of the “big questions” we’ve been pondering around succession planning. Think:
What should be included in a succession plan?
Who should own the process?
How do you identify the right candidates?
When does a plan need to be updated?
What steps can you take to begin?
When do you (or do you) tell your people?
How do you tailor a succession plan to your organization?
How do you get someone ready to step up?
What if there’s an emergency?
How do you choose who needs a succession plan?...
We’ve broken each question down into “On Paper” (what the research and best practices say about it) and “Our Take” (what we’ve seen and tried, how we think about it, and where adding people to the equation may make it messier). Then, there’s a “Character to Consider” – someone from business, history, or literature, who has wrestled with the issue, what the fallout was, and some lessons we might learn from their relationship to power and the transitioning thereof.
Within Permanent Equity, developing this resource required a group effort. As Managing Editor, Sarah George-Waterfield took the lead on curating existing research and character stories. She’s also the illustrator and designer. Tim Hanson and Emily Holdman, CIO/President and Managing Director, respectively, contributed Our Takes based on sometimes all-too-real operating experiences. And we worked together to hone a format and sequence intended to be constructive both for you and for our own leadership teams.
Our hope is that by deep diving into these questions, sharing our approach, and personifying some of the messiness with you that we’ll clarify our thinking on leadership transitions and open source a repository of research, ideas, and practices to make succession more successful for all.
– Tim, Emily & Sarah
Weekly editions being released through Spring 2025. Sign up to get them when they drop.
The Questions
001
002
003
004
005
006
When do you (or do you) tell your people? ➔
007
How do you tailor a succession plan to your org? ➔
008
How do you get someone ready to step up? ➔
009
How and why build a deeper talent bench? ➔
010
What if there’s an emergency? ➔
More to come Spring 2025.
The Resources
What specific challenges do small businesses face?
What’s the role of the outgoing leader?
What specific challenges do small businesses face?
Who should own the process?
What should be included?
What are the first steps you can take?
How do you tailor a plan to your org?
How do you get someone ready to step up?
How and why build a deeper bench?
What specific challenges do small businesses face?
Who needs a succession plan?
Why plan anyway?
What should be included?
Who should own the process?
How do you know when a plan needs updated?
Why plan anyway?
Who should own the process?
How do you identify the right candidates?
Why plan anyway?
What’s the role of the outgoing leader?
Can you plan for a new direction?
What if you want to keep the secret sauce?
When do you (or do you) tell your people?
What specific challenges do small businesses face?
What are the first steps you can take?
How do you get someone ready to step up?
Who needs a succession plan?
What if you want to keep the secret sauce?
What if you want to capture the secret sauce?
What should be included?
How do you identify the right candidates?
Who needs a succession plan?
What if you want to capture the secret sauce?
What should be included?
Who needs a succession plan?
How do you fill the top spot?
What’s the role of the outgoing leader?
How do you make sure a transition sticks?
What if you want to capture the secret sauce?
How do you fill the top spot?
What are the first steps you can take?
What specific challenges do small businesses face?
When do you (or do you) tell your people?
What’s the role of the outgoing leader?
What’s the role of the outgoing leader?
Who should own the process?
How do you identify the right candidates?
How do you know when a plan needs updated?
How do you fill the top spot?
What if there’s an emergency?
What if there’s an emergency?
How do you identify the right candidates?
Who should own the process?
How and why build deeper talent bench?
How do you identify the right candidates?
What’s the role of the outgoing leader?
What specific challenges do small businesses face?
How do you identify the right candidates?
How do you get someone ready to step up?
What if there’s an emergency?
What’s the role of the outgoing leader?
Can you plan for a new direction?
How do you fill the top spot?
What’s the role of the outgoing leader?
When do you (or do you) tell your people?
How and why build a deeper talent bench?
Can you plan for a new direction?
What if you want to capture the secret sauce?
Who needs a succession plan?
Why plan anyway?
Why plan anyway?
Why plan anyway?
What should be included?
Why plan anyway?
How do you tailor a succession plan to your org?
Who needs a succession plan?
How do you tailor a succession plan to your org?
When do you (or do you) tell your people?
How do you get someone ready to step up?
How and why build a deeper talent bench?
What are the first steps you can take?
How do you get someone ready to step up?
Why plan anyway?
What if you want to keep the secret sauce?
How do you make sure a transition sticks?
What’s the role of the outgoing leader?
Can you plan for a new direction?
The Characters
Inflection points | Knowing when it’s time | Legacy
The peculiarities of a sole succession planner | What makes a good transition | Inheriting succession woes
Recognizing change | When there are no good options | Identifying rot
Loyalty tests & long-term strategy | Trust erosion & dangled promises | Houses of cards & power vacuums
What you say vs. what you do | Flat-footed, wrong-footed, on the back foot | Any step forward is a step
Travis Kalanick
Blind on all sides | From smooth transition to scramble
Willy Wonka
Knowing your org | Recreating the unrecreatable
Henry IV
Legacy & lack of preparation | Divergent paths | The weight of expectations
Mark Hurd
When the bench is empty | And the next guy doesn’t last
Henry VI
From warrior king to unprepared heir | Lack of guidance & vision | Internal Conflict, Competing Factions & Fragile Foreign Alliances
Vito Corleone
Relationships matter | Options are limited | Legacy & Evolution
Spiro Agnew
Don’t skimp on the risk assessment | Replacements for the replacement
Kevin Plank
There and back again | Founder-dependent | Dependent founder
Jack Welch
Control, legacy, obsession | A cult of performance & a horse race to the top | Double-edged charisma
Viserys Targaryen
Certainty ≠ Consensus | More than a title | Unresolved ambiguities
Steve Ballmer
Recognition & response | Pushing the reset button | Slow pivots?
Steve Jobs
Cloning vs. complementing | Institutionalize vision, not person | Different successors → Different companies
Howard Schultz
The danger of being the keeper of the flame | When the leader can’t quit | Great CEO ≠ Great succession planner
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