How to facilitate a DIY strategy session

A well-facilitated strategy session helps an organisation gain clarity, alignment, and momentum. Not through a slick presentation or a motivational offsite, but through genuine consensus, shared understanding, and a sense of ownership over what comes next.

Done properly, a strategy session gives a business a clear view of what success looks like, what matters most right now, and how progress will be measured over the next few years. The person facilitating it plays a significant role in making that possible. A good facilitator creates the conditions for a group to honestly consider its aspirations, its purpose, the realities of its current and future situation, the resources it actually has available, and the needs of everyone who has a stake in the outcome.

The problem is that experienced strategy facilitators cost money. And sometimes a business needs a strategy session before it can afford one.

When that happens, someone internal usually gets the job by default, or the most senior person in the room ends up running the session while also trying to participate in it. They turn to Google for guidance. What they find is either too generic to be useful, too complicated to apply in a real session, or both.

This post is the practical alternative. It covers what needs to happen before, during, and after a strategy session, at two levels: what an experienced facilitator does, and what a capable internal person can do instead when budget does not allow for that.

BEFORE THE SESSION

What an experienced facilitator does:

Preparation is where most of the real work happens, and it is the part most DIY sessions skip entirely.

Before the session, an experienced facilitator will conduct a thorough desktop review of the organisation, the external environment it operates in, and any legislative or regulatory frameworks that apply to its work. They will design and distribute surveys targeted at key stakeholder groups, including employees, customers, and other relevant parties, to gather honest insight on internal challenges, external conditions, and issues that might not be visible to the people who will be in the room. They will also meet with a key contact inside the organisation to finalise the structure, planned content, and agenda for the session before it begins.

This preparation means the facilitator walks into the room already informed. The session can move faster, go deeper, and avoid the common situation where significant time is spent in the room establishing context that could have been gathered beforehand.

What to do if you are facilitating a strategy session yourself:

If you are preparing a strategy session without external support, the preparation phase is still non-negotiable. You simply need a structured way to work through it.

The DIY strategy session facilitator preparation guide below contains the questions to work through before your session to ensure you are properly prepared:

DIY strategy session - Facilitator Preparation Worksheet - copyright Juanita Vorster.pdf

Download PDF • 160KB

Use the guide in a way that supports you rather than overwhelms you!

For example: The information in the "next" column might already be available, or it might be exactly what needs to be discussed and decided during your strategy session.

DURING THE SESSION

What an experienced facilitator does:

A skilled facilitator guides the group through three phases during the session itself, without rushing any of them.

The first is helping the group establish focus: what the organisation is trying to achieve, what it stands for, and what it wants to be known for. This covers the organisation's ideal outcome, a scan of the scenarios most likely to affect it, and the formulation or refinement of its vision, mission, and values.

The second is helping the group honestly analyse the situation: the external environment, the internal environment, the needs of key stakeholders, and the gaps and obstacles that stand between where the organisation is now and where it wants to be.

The third is guiding the group to co-create a plan: what outputs are expected, what outcomes those outputs should produce, what impact the organisation is aiming for, how resources will be allocated, and what performance targets and indicators will be used to measure progress.

The facilitator's job throughout is to keep the group moving forward without letting it gloss over the hard questions, and to make sure that what gets agreed in the room is genuinely agreed, not just accepted by the loudest voices.

What to do if you are facilitating a strategy session yourself:

Running a strategy session from the inside is harder than it looks. The person facilitating needs to guide the group while also being part of it, which creates a real tension. A few things make it more manageable.

Separate your role clearly. Make it explicit to the group at the start that when you are facilitating, you are not participating as a leader or decision-maker. This helps others feel free to speak, and helps you resist the temptation to steer the conversation towards your own preferred outcomes.

The participant positioning worksheet below can help with that, and can also be a great opener of the session (without resorting to cringey ice-breaker games). It will give your nerves time to settle and will also help the group to gain broad insight into the needs of everyone participating in the session:

DIY strategy session - Participant Positioning Worksheet - copyright Juanita Vorster.pdf

Download PDF • 1.32MB

Ensure that the worksheets are completed anonymously. You can then summarise the anonymous contributions on flipchart paper in order to identify if the group needs to think a bit broader or narrower during the session.

Then use the three "experienced facilitator" phases above as your structure. Do not skip the analysis phase to get to the plan faster. The quality of the plan depends entirely on the honesty of the analysis.  It might also be valuable for the group at this point if you then share what you've discovered during your preparation for the session as a starting point for further discussion.

AFTER THE SESSION

What an experienced facilitator does:

A strategy session is only useful if what was agreed in the room gets captured accurately and followed through consistently.

During the session, an experienced facilitator will ensure that all decisions taken were accurately captured. After the session, they will guide the client on how to consolidate those decisions into documentation that will help the strategy to move from paper to implementation.

They may also provide structured support during implementation to evaluate whether the strategy is holding up and what, if anything, needs to be adjusted. This ongoing involvement is what separates a strategy session that produces lasting change from one that produces a document that sits in a folder.

What to do if you are facilitating a strategy session yourself:

Documenting the outcomes of a DIY strategy session does not need to be complicated, but it does need to be done deliberately. Resist the temptation to tidy up what was said in the room. The documentation should reflect the actual agreements made, in language that the people who made them will recognise and feel ownership over.

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A DIY strategy session might not produce the same outcome as one facilitated by someone with deep experience in the room, but that is not a reason to avoid it. A well-prepared, well-structured DIY session is significantly better than no session at all, and it can provide a strong enough foundation to build on as the business grows and the budget for more expert facilitation support becomes available.

For more in-depth guidance on how to prepare to facilitate a DIY strategy session, use the free Strategy Diagnostic Tool.