Run a Strategic Planning Workshop
Strategy · 1–2 days · Intermediate
The job
Facilitate a structured strategy day that moves from environmental analysis through positioning to a prioritised 90-day action plan.
What the sponsor gets
Each canvas and map from this playbook — PESTLE Canvas, SWOT Analysis, Prioritisation Matrix, OKR Canvas — exports as a PDF, or as PowerPoint on Pro, straight from the session, and the whole run exports as one PowerPoint for the sponsor. Nothing is redrawn.
The method
Conduct stakeholder pre-interviews
Interview 3–5 key stakeholders individually before the session. Focus on their view of the strategic question, what success looks like, and what constraints they see.
Tip: Send a 3-question pre-read 48 hours before the interviews to get richer responses.
Scan the external environment
Use PESTLE to systematically review political, economic, social, technological, legal, and environmental factors affecting your strategic context.
Tip: Use AI Generate to get a starting point from your industry context, then refine with the team.
Assess your strategic position
Create a SWOT canvas, pulling external factors from your PESTLE into Opportunities and Threats, then adding internal Strengths and Weaknesses.
Tip: Challenge the team to be brutally honest about weaknesses — this is where the real value lives.
Facilitate divergent ideation
Run a structured brainstorming session using the insights from PESTLE and SWOT. Use breakout groups to prevent groupthink, and give quieter voices space to contribute.
Tip: Set a timer and enforce "no evaluation" during divergence — clustering comes next.
Prioritise strategic options
Plot all candidate initiatives on an impact-vs-effort matrix. Force the team to make trade-offs rather than declaring everything high priority.
Tip: Give each participant 3 votes to spend — it surfaces genuine preferences faster than open debate.
Define 90-day objectives
Translate the top priorities into OKRs with measurable key results. Each objective needs a single owner and a review date.
Tip: Limit to 3 objectives — more than that and nothing gets focus.
Document commitments and circulate
Summarise the day into a one-page action plan with owners, deadlines, and the next review date. Send within 24 hours while energy is high.
Tip: Schedule the 30-day check-in before you leave the room.
The canvases and maps
- PESTLE Canvas
- Six fixed boxes — political, economic, social, technological, legal and environmental — so the room scans the whole outside world, not just the two forces it already worries about.
- SWOT Analysis
- Four quadrants split inside from outside and helpful from harmful, so strengths cannot hide threats and every point has to land somewhere.
- Prioritisation Matrix
- Impact against effort in four quadrants — quick wins, major projects, fill-ins and avoid — so the team trades off instead of calling everything a priority.
- OKR Canvas
- One objective, three key results and the initiatives beneath them, so ambition and measurement sit on the same page and no initiative floats free of a result.
What it doesn't do
It doesn't run the room for you or decide for the client. The steps, canvases and duration are a starting point you adapt; the judgement stays yours.