Why Piloting Executive Coaching Reduces Risk and Increases Impact
By the time you get to this stage in deciding how to choose executive coaching services, you may feel ready to roll out coaching to a wide population of leaders.
Resist the temptation to go straight to scale.
A well-designed pilot allows you to:
- Test your assumptions about outcomes, audience, format and methodology.
- See how leaders actually respond to the coaching in your culture and context.
- Learn what needs to be adapted before you invest at scale.
In other words, a pilot is not a tentative, watered-down version of the “real” programme. It is the first, deliberate phase of doing it properly.
What a Good Executive Coaching Pilot Looks Like
A strong pilot has a clear scope, purpose and design. It typically includes:
- A defined population
For example, the CRO plus a handful of regional VPs, or a small cohort of Heads of Sales and Enablement.
- Clear objectives
What you want to learn, not just what you want leaders to experience.
- Time-bound duration
Often 3–6 months, long enough to see behavioural shifts and early signs of impact.
- Structured evaluation
Agreed touchpoints to review progress, capture learning and decide on next steps.
Think of the pilot as a controlled experiment in how executive coaching works in your specific organisation, not just a sample of sessions.
Define the Purpose of Your Pilot
Before you design the details, be explicit about why you are running a pilot.
Common pilot purposes include:
- Fit and credibility
Testing whether the provider and coaches are a good fit for your leaders and culture.
- Format and logistics
Seeing how different formats (1:1, team, group, blended) work in practice and how easy they are to coordinate.
- Engagement and readiness
Understanding how willing leaders are to engage with coaching and how it lands alongside other priorities.
- Impact and measurement
Exploring what changes you can realistically observe and measure within a short timeframe.
Capture 3–5 clear questions your pilot should answer, such as:
- “Do our regional VPs find this style of coaching helpful and credible?”
- “Can we see tangible changes in how pipeline reviews are run?”
- “What support do line managers need to reinforce coaching?”
These questions will shape who you include, how you design the pilot and what you pay attention to as it runs.
Select a Representative, High-Influence Cohort
Who you include in the pilot matters.
Aim for a cohort that is:
- Representative
Includes leaders from key regions, functions or business units where you ultimately want to scale.
- High influence
Leaders whose behaviour and advocacy will affect others – for example, the CRO, key regional VPs or Heads of Sales.
- Ready to engage
People who are open to coaching and willing to give honest feedback on the experience.
Avoid using the pilot as a place to “park” the most resistant or problematic leaders. You want a realistic test, not a guaranteed failure.
You can also include a small comparison group – leaders who are not in the pilot but whose metrics and behaviour you will track for context.
Design the Coaching Experience for the Pilot
With purpose and population defined, design the pilot coaching experience.
Decisions to make include:
- Number and cadence of sessions
For example, six 60–90 minute sessions over four months, plus contracting and review meetings.
- Mix of formats
Will you combine 1:1 coaching with team or group sessions? How do these fit together over time?
- Focus areas
Core themes aligned to your outcomes – for example, pipeline reviews, decision-making, cross-functional collaboration.
- Practice and assignments
Specific experiments leaders will run between sessions, and how they will be reviewed.
- Integration touchpoints
How coaching connects to operating rhythms such as QBRs, leadership meetings and enablement activities.
Design the pilot in collaboration with your chosen provider and your internal sponsors so expectations are shared from the start.
Set Baselines and Decide What to Measure
Measurement in a pilot should be practical and purposeful, not burdensome.
Before the pilot begins, capture a simple baseline, such as:
- Quantitative data
Relevant metrics by leader or team – for example, win rate, pipeline quality indicators, forecast variance, engagement scores.
- Qualitative input
Short sponsor, peer or team feedback on current leadership behaviours in key moments (pipeline reviews, decision forums, etc.).
During and after the pilot, track:
- Leading indicators
Changes in how leaders run meetings, coach their teams, make decisions and collaborate.
- Lagging indicators
Any movement in the commercial metrics you identified, recognising that coaching is one of several contributing factors.
You don’t need complex analytics. You do need a consistent, transparent approach that lets you say, “Here’s what we saw change.”
Build in Feedback Loops From Coachees and Sponsors
Feedback is one of the most valuable outputs of a pilot.
Plan structured opportunities to gather it from:
- Coachees
How relevant and useful they found the coaching; where it helped them behave differently; what could be improved.
- Sponsors and line managers
What they have observed in leader behaviour and impact, and how easy it has been to align coaching with business priorities.
- Coaches
What they have learned about your culture, systems and constraints; what they would recommend changing in a larger roll-out.
You can use short surveys, structured debrief conversations or a mix of both. The important thing is to capture insights systematically, not just rely on anecdotes.
Plan Clear Stage-Gates and Decisions
A pilot is only useful if it leads to informed decisions. Before you start, agree:
- When you will review progress
For example, at the halfway point and at the end.
- Who will be involved
Typically HR / L&D, the CRO or equivalent, and key sponsors.
- What decisions you will make
For example: scale as planned, scale with adjustments, extend the pilot, change provider, or stop.
Use your original pilot questions and success criteria as a guide. Be honest about what worked, what didn’t and why.
Document your conclusions so they inform future decisions, even if you choose not to scale with that particular provider.
Make It Easy to Scale – or to Stop
Your commercial and contractual arrangements (see Step 8) should support piloting.
Aim for:
- A clear pilot commercial
Defined fees for the pilot phase, with options to expand if agreed criteria are met.
- Simple scaling mechanisms
Pre-agreed rates and structures for extending coaching to more leaders, regions or formats.
- Low exit friction
The ability to stop or change direction at the end of the pilot without punitive costs.
This keeps both you and the provider focused on creating value, rather than just fulfilling a contract.
Communicate the Pilot Clearly Inside the Organisation
How you communicate the pilot internally shapes how it is perceived.
Make sure you:
- Frame it as a strategic investment
Not an experiment on leaders, but a thoughtful first phase of building a coaching culture.
- Explain selection criteria
So those included don’t see it as remedial, and those not included don’t see it as favouritism.
- Set expectations on confidentiality and reporting
So leaders know what to expect and feel safe to engage.
- Signpost what comes next
Explain that the pilot will inform future decisions about coaching for other leaders.
Clear communication builds trust and prevents misunderstandings that could undermine the pilot.
How Step 9 Completes the Decision Process
Running a low-risk pilot before you commit is the final step in a robust process for how to choose executive coaching services.
Together, the nine steps help you:
- Define the outcomes you want coaching to support.
- Decide who coaching is for and how it should be delivered.
- Evaluate providers on methodology, sector expertise, practice and governance.
- Agree commercial terms and ROI expectations.
- Test, learn and refine before you scale.
Done well, a pilot gives you real evidence – from your own leaders, in your own context – that the coaching partner you choose can help change what leaders do every day, not just what they talk about in the room.