How To Pick A Strategy Facilitator?

Over the last 30 years I’ve lead dozens of teams through strategic planning as a CEO and as an outside facilitator. I’ve learned there are three essential characteristics for a good facilitator.

  • Strong listening skills
  • A coherent framework
  • A track record of success
  • Bonus Round: Market knowledge and insight

As you are deciding who should lead your process these criteria can help winnow the field.

Strong Listening Skills

A good listener knows how to ask questions and hear the answers in a way that helps everyone discover the truth. In your initial encounters with facilitators see what kinds of questions they ask and how they frame them. Are they trying to uncover the truth or manipulating the conversation? Do they hear your answers and ask probing follow-ups or do they barrel ahead with a fixed agenda? Did they probe deep enough that you get insights from your answers?

In the planning process this skill will help them be an effective referee for the differences across your team. Helping people state their case, feel heard, and develop deeper insights from the inquiry is the heart of the Socratic process.

Taking a team through a planning process taxes this skill at a high level.

A Coherent Framework

Nothing is worse than a planning meeting that wanders all over the place and leaves everyone more confused than when they started. Get it right the first time.

A planning framework insures the right topics get discussed in the logical sequence. A couple of good focused days can lead to months of productive action if the discussion has strong bones.

A good framework should touch on the following questions in one way or another:

  • What do we want to be as an organization?
  • Who is our target customer and what do they need?
  • Who is the competition?
  • What is the winning narrative for the customer and competition?
  • What tasks will bring this to life?
  • How do we measure success?

Your facilitator ought to be able to show you 2-3 approaches to tackling these questions and should tailor an approach to your specific requirements. Do you need a tune up or an overhaul? Those are very different planning processes even if they core questions are the same?

A related reason to use a framework is pacing. A facilitator who has used a framework knows where things are likely to bog down. They also know how to keep a team on track so that all the questions get addressed in the scheduled time.

A Track Record of Success

Planning is only useful if it leads to action and results. Action and results are destroyed by inconsistencies. Here are a couple of examples:

  • Don’t promise ease of use, but have a complex purchasing process that undercuts this message.
  • Don’t build a complex solution to a simple non-problem.

Being smart can help identify these inconsistencies, but experience trumps brains in this department.

Your ideal facilitator has implemented the approaches they recommend to you. It helps if they have had P&L responsibility in the C-Suite as well as experience as a facilitator. There are lots of decent facilitators who don’t bring management insights to the conversation. There are lots of executives who don’t know how to catch logical inconsistencies in real time. You need both.

It is also important that the facilitator have experience with executives. Challenging everyone’s thinking (including the CEO) is a critical part of leading this discussion. You want a strong listener who also won’t be pushed around by the group.

Bonus Round: Market Knowledge & Insight

All too often organizations go astray because what they think they know isn’t valid anymore. A facilitator who can challenge closely held assumptions (through good questions), who can force the team to think more deeply, is invaluable. To insure this happens pick someone with insight into your market.

Yes – there are awesome facilitators who can lead a planning meeting with limited market knowledge. But in an ideal world you’ll have both skill sets..

Inside Or Outside Facilitator?

An outside facilitator isn’t required. If your insider has these characteristics they can do a solid job of it. But, an outsider can add a lot because they are not steeped in the day-to-day operating assumptions of your business. This means they are more likely to catch logical inconsistencies. They are also not part of the formal or informal power and social structure. This means they can challenge your team to look clearly at the world.


Strategic planning is your chance to stop and check the map to make sure you are headed in the right direction. Pick the right facilitator so your team’s time is well spent and you end up with a clear path forward.

Facilitator Checklist:

  1. Takes the time to understand your planning needs, do they listen well?
  2. Has a range of planning frameworks to draw on
  3. Proposes a solution tuned to your needs
  4. Managerial experience (preferably C-Suite)
  5. Facilitator experience with executives
  6. Success based references from similar organizations
  7. Bonus Round: Market knowledge & insight