Planning a strategy workshop: format, agenda, and methods for two days

The two-day agenda in detail, the preparation that makes or breaks it, and the question of whether to facilitate in-house or bring someone in.

By Christian Underwood ·

Sechs Platzkarten im Rechteck angeordnet, in ihrer Mitte ein flach liegender Rahmen; eine Karte ist hervorgehoben.
Contents (8 sections)
  1. What goes into preparing a strategy workshop?
  2. How long does the workshop need to be?
  3. Which three questions need a yes beforehand?
  4. Which methods fit which block?
  5. Who facilitates, internal or external?
  6. How do you capture decisions so they stick?
  7. What happens in the two weeks that follow?
  8. Frequently asked questions about strategy workshops

What goes into preparing a strategy workshop?

In the StrategyFrame®, this session is called Strategy Workshop I and belongs to the FOCUS step, the third of eight. What happens in it follows a fixed sequence: first the results of the situation analysis, then the shared insights, then the challenges, then the options for action, and only at the end the target picture. Change the order and you end up debating goals before it's clear what they're answering.

Preparation determines the outcome, and it starts four to six weeks before the session.

Three things need to be in place before the group comes together: an analysis of where the company actually makes its money, an assessment of how the market is developing, and interviews with the participants, who each say beforehand what they consider the most pressing question.

The interviews are the underrated part. What people say one-on-one differs systematically from what they say in the group. If you know those differences in advance, you'll run the two days completely differently.

Without preparation, the first morning is gone, reliably. That leaves a day and a half out of two.

How long does the workshop need to be?

Two and a half days. That sounds like a lot and it's the most common point of contention in planning. Time and again there are bosses who don't want to give up more than a single working day. The math against that is simple: it usually takes a full day before all participants have mentally arrived and genuinely accepted the starting position. If you only have that one day, you get exactly that far and go home without a target picture.

Time frame

What happens

Result at the end

Day 1, afternoon

Arrival, introduction to the agenda, presentation of the results from the situation analysis. Dinner together in the evening, no program.

Everyone is there and knows the numbers. The next morning starts without waiting for latecomers.

Day 2, full day

Build a shared understanding of the starting position, assess opportunities and risks, develop proposed solutions.

A shared view of the situation, including where it's uncomfortable. Plus options with their consequences.

Day 3, morning

Draft a complete target picture and plan the next steps.

Target picture, fields of action and decisions with names and dates.

The half day at the start isn't a buffer. It's the reason work can begin immediately on the second morning instead of people still settling in.

For everything beyond the actual task, less is more. Inspiring guest speakers who've completed an Ironman and extra team activities cost exactly the time you'll later miss for the target picture. Dinner together is enough.

Which three questions need a yes beforehand?

Three questions belong settled before the workshop starts. If one answer is no, postpone the session rather than hold it.

  • Is the situation analysis complete? Not started, not mostly done. Complete.
  • Have all participants been invited? Whoever decides in the workshop has to be there from the start.
  • Was everyone involved in the situation analysis? Through an interview, through working on a module, at least through the guiding questions. Anyone seeing the analysis for the first time in the workshop will discuss data quality there instead of direction.

Then comes the actual planning, along five guiding questions: the objective of the workshop, the duration and flow, the participants, the location and the facilitation. The agenda grows out of those answers, not the other way around.

Which methods fit which block?

The first block needs good materials, not a method. Methods only help once the discussion starts.

  • Collecting options: SWOT as a derivation, not as a list-making exercise. The question isn't "what are our strengths," it's "which of our strengths meets which market development."
  • Evaluating options: the same three to four criteria for every option, defined in advance. Define the criteria during the evaluation and you'll define them to fit your favorite option.
  • Making trade-offs visible: a list of what you will no longer do. Without it, every strategy is a declaration of intent.
  • Documenting: one sheet, one page, all decisions. If it doesn't fit on one page, nothing was decided.

Who facilitates, internal or external?

The honest answer comes down to one question: does the person facilitating have an opinion on the outcome?

When the managing director facilitates, two things happen. The group reads a judgment into every follow-up question, and the managing director can't argue his own position without giving up the facilitation. Both cost more than external facilitation does.

Internally, it works when someone holds the role but has no position on the topic, for example someone from a different part of the business. That's rare, but when it's possible, it's the cheapest route.

How do you capture decisions so they stick?

Three items per decision: what was decided, who owns it, and by when the first step becomes visible. If one of them is missing, it isn't a decision.

The minutes are written during the workshop, not afterward. Whatever gets reconstructed from notes three days later is the note-taker's memory. A decision that is written on screen for everyone to see while the group is still in the room is a different decision.

What happens in the two weeks that follow?

This is exactly where it's decided whether the workshop had any impact. Two weeks is the window in which the energy still carries.

  • Send out the one-pager, within two days at the latest. Not a photo of the pinboard.
  • Set the next date before everyone leaves the room. A meeting four weeks out that is agreed on in the room actually happens. One that gets scheduled later keeps moving.
  • Launch the first initiatives, even if the planning isn't complete. One visible first step is worth more than a complete plan in month four.
  • Inform the rest of the company. Not with the strategy paper. With what actually changes for each area.

Frequently asked questions about strategy workshops

How long should a strategy workshop last?

Two and a half days for the first workshop after the situation analysis: half a day for arrival and presenting the findings, a full day for the current situation, opportunities, risks and proposed solutions, and half a day for the target picture and next steps. A single day isn't enough, because getting everyone on the same page about the situation usually takes a day on its own.

How do I prepare a strategy workshop?

Start four to six weeks ahead. You need three things: an analysis of where the company actually makes its money, an assessment of how the market is developing, and one-on-one conversations with the participants. Without that preparation, the first morning is gone.

How long should a strategy workshop last?

Two consecutive days is the standard format for the decision phase. One day is enough for a status check, not for a decision on direction. The discussion needs a night in between.

Who facilitates the strategy workshop, someone internal or external?

What matters is whether the facilitator has an opinion on the outcome. The managing director can't facilitate and argue his own position at the same time. Internal works if someone takes the role who has no stake in the topic itself.

Which methods work well in a strategy workshop?

SWOT used to derive conclusions rather than as a list-making exercise, an assessment of all options against criteria defined in advance, and an explicit list of what you will not do. For the first block, you need good materials, not a method.

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