Is It Really a Leadership Hire?

A practical framework for diagnosing leadership capability gaps in investor-backed businesses

Investor-backed organisations often begin with a job title.

“We need a COO.”

“We need a Transformation Director.”

“We need someone more commercial.”

But the more useful starting point may be: What actually needs to change in the business?

Because an underperforming function, stalled transformation or missed growth target does not automatically mean the answer is another Executive appointment. Sometimes the constraint is leadership.

Sometimes it is structure, operating model, capability, incentives or decision making. Before launching a search, it is worth diagnosing the problem properly.

1. What outcome must change?

Start with the investment plan rather than the organisation chart. What needs to look materially different in the next 12–24 months?

For example:

• EBITDA or margin improvement
• Operational scale
• International expansion
• Acquisition integration
• Customer retention
• Cost-to-serve
• Digital adoption
• Workforce productivity
• Improved data and decision-making
• Stronger leadership succession

If the required outcome is unclear, the leadership brief will usually be unclear too.

2. What is actually constraining delivery?

Ask whether the problem is primarily:

Strategy
Is there genuine clarity on what needs to happen?

Operating model
Is the organisation structured to deliver it?

Capability
Does the business have the skills and systems required?

Leadership
Is somebody capable and accountable for turning the plan into execution?

These are different problems.

Hiring a new Executive cannot compensate indefinitely for an unclear strategy or broken operating model.

3. Has the business outgrown the leadership team that got it here?

The leadership capability required to build a £50m organisation may be very different from that needed to scale towards £150m.

This does not necessarily mean existing leaders have failed. The business may simply have changed. Common transition points include:

• Founder to professional management
• Single-market to international
• Organic growth to M&A
• Entrepreneurial decision-making to operating discipline
• Functional leadership to enterprise leadership
• Informal systems to scalable processes
• Transformation programme to embedded capability

The question is whether the current leadership team matches the organisation the investment plan is trying to create.

4. What must the incoming leader be able to do?

This is where many searches become too CV-led. Instead of asking only whether someone has held the same title or worked for a similar company, define the capabilities required.

For example:

• Build operating discipline without killing entrepreneurial pace
• Integrate acquisitions
• Restructure a function
• Improve customer economics
• Create performance visibility
• Drive adoption of new technology
• Lead through resistance
• Improve margin
• Build a stronger team beneath them
• Operate effectively with an investor or Board

The best candidate may not have followed the most obvious career path.

5. What happens if this appointment is wrong, or six months late?

Leadership searches carry a cost beyond recruitment fees. A delayed or unsuccessful appointment can affect:

• Transformation timelines
• Acquisition integration
• Customer performance
• Management confidence
• Employee retention
• Investor confidence
• Growth milestones
• The eventual value creation case

That makes speed important. But speed without clarity usually creates a different risk: appointing the wrong leader faster.

A simple diagnostic: Replace, Add, Develop or Restructure?

Before launching a search, consider four possibilities.

Replace
The current leadership capability no longer matches what the business requires.

Add
The existing team is strong, but new capability is missing.

Develop
The required capability may already exist internally with the right support, succession planning or development.

Restructure
The problem may sit in the operating model rather than the individual.

That distinction matters because the right answer is not always “hire another Executive”.

The investor lens

For investors and portfolio leaders, Executive hiring should ultimately connect back to value creation. The most useful question may therefore be:

What leadership capability does this investment thesis now require that the business does not currently possess?

Once that is clear, the search becomes much more precise.

Douglas Jackson works with investors and portfolio leadership teams to identify leadership capability gaps and appoint senior leaders across Operations, Transformation, Customer, Data and Strategy. Sometimes that leads to a retained Executive search. Sometimes it leads to an interim, fractional or different leadership solution. Either way, the starting point is the same:

Understand the outcome before defining the hire.

Discuss a portfolio leadership challenge →

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