Succession planning in pencil

Ben Kershaw

It always starts with a scrap of paper.

Not a spreadsheet. Not an elaborate framework. Just a messy, rough sketch of what the team could look like—if everything goes to plan.

I recently worked through this with a client. The goal? To map out what their organisation should look like at the end of their next growth phase. Not what it looks like today. Not how they feel about the team. But a blank-slate view of the business structure needed to hit their goals.

This isn’t a new idea. Jim Collins fans will recognise it as “right people, right seats.” But we added a twist: don’t just think about the seats for today—but the ones you’ll need in 12, 24, 36 months’ time. Then ask: who, if anyone, will be ready for those seats?

It sounds simple. It is. But it’s also revealing.

Start with the structure, not the people

In succession planning the mistake businesses can make is thinking about people first. Who do we have? Who deserves a promotion? Who’s stepping up?

It feels fair. It feels kind. It’s also a great way to lock in a structure that doesn’t fit your future.

Instead, start with the endgame in mind. What will the organisation look like if you hit your targets? What roles will be needed? What size will each team be? Who should lead them?

Draw that version of your org chart—based on what the business needs to succeed.

Then, once you’ve got that model, you can start pencilling in names.

Think in two stages: growth mode and next horizon

In this exercise, we did two versions.

First, we mapped out what the business would look like in 12 months—if revenue targets were hit and the hiring plan executed. This is usually the “next logical step” org structure. Most of the current leaders stay in place but with expanded teams or clearer lines.

Second, we stretched it further. What does the org chart look like in 2–3 years? What happens when the next level of complexity kicks in? That’s when things get interesting.

Leaders who seemed a great fit today start to feel like they’re being asked to wear shoes a size too big. Others might flourish with scale, but only if given the chance to prepare. And you realise: it’s not just about competence. It’s about appetite. Energy. Ambition.

Some roles might need to be reshaped. Some people may need to find new seats. Others need investment to stretch into their future seats.

The future-fit test

This isn’t about making immediate changes. It’s not about clearing the decks or making harsh calls on your existing team. It’s about asking good questions early:

• Is this person going to thrive in this role two years from now?
• Do they want it? Do they know what it will demand?
• Will they grow into the role—or grow frustrated by it?
• Is this person’s experience relevant to where we’re going?

And here’s the uncomfortable truth: just because someone has been with you from day one doesn’t mean they’re the right person to lead in year five.

That doesn’t make them any less valuable. But it does mean you owe it to them—and to the business—to think ahead. To be honest about the fit.

Succession planning for roles that don’t exist yet

Here’s the thing: you can’t succession plan effectively if you don’t know what the future roles are.

Too many leadership teams only plan successors for the jobs that exist today. But what if the head of operations needs to become a COO? What if your sales manager needs to build out a commercial function?

You can’t expect people to step into these roles cold. You also can’t assume they’ll want to.

So the real value of this exercise is in surfacing those future roles—before they’re urgent. Then you’ve got time to assess the gaps, build capability, and have honest conversations.

Not solving—just sensing

A word of caution: this is not a crystal ball exercise. You’re not trying to predict the exact structure of the business in 2028.

This is a sensing exercise. A way to spot risks early, test assumptions, and start the right conversations. It’s not about locking in names or building succession charts in PowerPoint.

It’s about reframing how you hire, promote, and plan.

Every time a new hire is approved, ask:

“Are we hiring for today—or for the business we want in two years?”

If it’s just about today, you may be locking in a short-term fix that slows your future.

If it’s about tomorrow, you’re more likely to attract people who will stretch, grow, and scale with you.

You don’t need a workshop—just a pencil

Yes, we can help with the complex stuff. Capability assessments. Readiness mapping. External talent planning. There are consulting models for all of it.

But the real magic is in the napkin sketch. The 30-minute chat with your senior team. The scribbled org chart that you revisit every time a role changes.

You don’t need a 60-page strategy document. You just need to ask:

“What does our business need to look like in 3 years?”
“And are we building towards that?”

Closing thought: the gift of turnover

It might sound ruthless, but some of your current team might be better off elsewhere in a few years. That’s not failure. That’s movement. Growth. The healthy turnover that comes with ambition.

It’s not just about getting the right people in the right seats.
It’s about building the bus you actually want to drive.

Contact Moxie to book a hiring strategy call.