A Planning Workshop that Delivers
Photo by Elena Popova on Unsplash
How to Run a Planning Workshop that Delivers Clarity, Alignment, and Action
In today’s dynamic environment, yesterday’s plan can quickly be overtaken by events. Markets shift. Technology outpaces product roadmaps. Customers escalate. Competitors you’d never heard of six months ago are suddenly all over your feed.
That’s usually when someone says, “We need a planning session.”
Too often, what follows is little more than a budget review and an ever-expanding wish list driven by the loudest voices in the room, missing the opportunity for the conversation that truly matters: Where are we heading? What forces will shape our trajectory? And how will we adapt to the obstacles ahead?
Why Planning Matters More Than Ever
In fast-moving markets, strategic planning isn’t a luxury, it’s a lifeline.
It’s not a weighty slide deck that sits on a shelf gathering dust. Done well, it’s the discipline that keeps your company focused, aligned, and ready to respond.
Strategic planning connects today’s execution with tomorrow’s ambition. It provides:
Focus — the ability to say no to compelling distractions. Not every good idea deserves investment, and a clear strategy helps you tell the difference.
Clarity — the discipline to look beyond the next quarter. Even choosing not to act on a future trend is a strategic decision when made intentionally.
Coherence — alignment between long-term purpose and short-term action. It ensures every initiative ladders up to a larger mission instead of reacting to the fire drill of the day.
Without this discipline, companies drift into the tyranny of the urgent—chasing squeaky wheels, vanity metrics, or competitor moves at the expense of building lasting value.
Strategic planning breaks that cycle. It transforms reactive energy into proactive clarity.
Preparing for the Workshop
Good preparation is the difference between a transformational experience and a frustrating waste of time.
The first important decision is who should be in the room. Every key function needs representation. The value of the workshop isn’t just the deliverables that come out of it, it’s the shared understanding built across teams, the empathy for each other’s unique challenges, and the alignment on priorities, tradeoffs, and operating rhythm. When key voices are absent, ownership suffers and follow-through flounders.
At the same time, participation matters. The larger the group, the stronger your facilitator must be. Too many participants and the session becomes too expensive, and difficult to manage.
Given the investment, not only in time but in executive focus, it’s critical that the facilitator is experienced in running these types of workshops. A skilled facilitator makes the difference between a workshop that drifts and one that delivers lasting clarity and alignment.
The second preparatory step is gathering and circulating any useful background reading. These often include such items as:
Key business metrics
Product Roadmaps
Sales metrics
Win/Loss reports
Customer satisfaction metrics and churn reasons
Competitive intelligence
Now, schedule the time, book the room (ideally offsite for increased focus), and get ready to get started…
Structuring the Conversation
A proven way to structure your planning workshop is through the Three Horizons Model (popularized in The Alchemy of Growth).
It separate the conversation into today, what’s next, and what could be beyond that:
Horizon 1: Strengthen the core business. Defend, optimize, and grow what drives revenue today.
Horizon 2: Develop emerging bets. Adjacent opportunities, new segments, or evolving customer needs that could fuel the next stage of growth.
Horizon 3: Explore the future. Long-term technologies, disruptions, or shifts that could redefine your category entirely.
Visually mapping initiatives across these horizons helps teams see not just what they’re doing, but why, and where each investment sits on the timeline.
Defining the Horizons
Best practice is to define horizons not just by time, but by certainty and optionality. How much you know and how much freedom you have to act.
| Horizon | Definition (Modern SaaS) | Decision Characteristics |
|---|---|---|
| Horizon 1 | Known business model, validated markets, clear ROI | Operate → Optimize |
| Horizon 2 | Emerging opportunities with testable hypotheses | Experiment → Scale |
| Horizon 3 | High uncertainty, exploratory R&D or category creation | Explore → Learn |
Still, anchoring each horizon to a time window helps create shared context for the rest of the workshop. Typical SaaS ranges are:
| Company Stage | Recommended Horizons | Notes |
|---|---|---|
| Early (<$10M ARR) | H1: 0–12 mo · H2: 12–24 mo · H3: 24–48 mo | Rapid learning cycles and capital efficiency require shorter spans. |
| Growth ($10–100M ARR) | H1: 0–18 mo · H2: 18–36 mo · H3: 36–60 mo | Balance scaling current growth with exploring adjacent bets. |
| Mature (>$100M ARR) | H1: 0–24 mo · H2: 24–48 mo · H3: 48–72 mo | Larger orgs can afford longer horizons but should still revisit quarterly. |
Once you’ve agreed on the period of each horizon, you can start building the full picture.
Start with the External Forces Shaping Your Future
Your company doesn’t operate in a vacuum. Begin by exploring the external forces influencing your market. Later, you’ll analyze how they affect your specific strategy.
Consider five categories:
Technological: AI, automation, integrations, XR, and platform economics
Regulatory: privacy, data sovereignty, ESG, and AI governance
Societal: expectations for transparency, sustainability, and brand integrity
Geopolitical: supply-chain dynamics, regional stability, and new trade environments
Competitive: new entrants, pricing pressure, and business-model innovation
To go deeper, use Porter’s Five Forces to analyze competitive intensity.
Map these categories across the three horizons. Add two dimensions, impact and certainty, to highlight what’s shifting fastest and what will matter most.
The real value comes from the conversation: debating, challenging, and ultimately aligning around the 2–4 most significant forces in each category and horizon. Together, these provide a powerful picture of the environment in which your organization operates now and into the future.
Spot the Tailwinds and Headwinds
Next, translate those forces into opportunities and threats.
Ask:
Which forces represent tailwinds, momentum we can harness to accelerate growth?
Which are headwinds, challenges that could slow us down or erode our advantage?
Plot each on a simple 2×2 grid: Impact (low–high) vs. Timeframe (near–distant).
This visual quickly reveals what requires immediate attention versus long-term monitoring.
Define Your Unfair Advantage
Once you understand the external world, turn inward and ask your team:
“What gives us an advantage that competitors cannot easily copy?”
These are your unfair advantages, the foundation of your defensible differentiation. They explain why customers buy from you and why they stay. They may include:
Deep customer intimacy and trust
Proprietary data or platform integrations
Brand authority within a niche
Domain expertise in complex or regulated markets
A culture of adaptability and innovation
Identify and define these strengths. They are the levers you’ll pull to amplify tailwinds and counteract headwinds.
Frameworks like VRIO can help guide this conversation.
Acknowledge the Weak Spots
Equally important is an honest look at what’s holding you back. This is often a difficult conversation that requires vulnerability from participants so set the facilitator should set the tone appropriately. Ask:
Where are we operationally or culturally constrained?
What capabilities are missing to pursue Horizon 2 or 3 opportunities?
What habits or assumptions must we unlearn to move faster and smarter?
No organization has unlimited time, money, or people. Recognizing constraints builds realism and trust, and helps ensure your resulting plan is feasible.
Strategy isn’t just choosing what to pursue; it’s also choosing what to fix and what to decline.
Use another 2×2 grid, (Impact vs. Timeframe) to prioritize which weaknesses demand immediate attention and which can be addressed later.
Summarize into the Horizons Framework
Now, pull it all together. For each horizon, capture:
The external forces in play
The tailwinds and headwinds you face
Your key strengths and weaknesses
Then, as a team, discuss each horizon and brainstorm the initiatives that will accelerate progress toward your mission and vision.
Collaborate to prioritize those initiatives. The debate itself is invaluable, surfacing differing perspectives and leading to a shared commitment.
Add the top priorities to your Three Horizons map. This one-pager becomes the foundation of your strategic plan, a visual snapshot of what matters most and when.
Turn Insight into Action
Finally, translate insight into action:
Prioritize initiatives across horizons: what do we scale, pause, or explore?
Assign ownership: every priority must have a clear champion.
Define learning goals for emerging bets: how you validate your hypotheses.
Establish cadence: this is a living document, revisit and refresh it quarterly to stay adaptive.
A strategy that isn’t updated regularly isn’t a strategy, it’s an anachronism.
A Living Strategy, Not a Static Plan
The most valuable outcome of a planning workshop isn’t the deck you create, it’s the alignment you achieve.
The conversations that shape the plan build empathy across teams, deepen understanding of interdependencies, and strengthen trust.
When everyone shares the same map of where they’re going, decision-making accelerates, execution sharpens, and confidence grows.
In a world defined by uncertainty, the goal isn’t to predict the future, it’s to prepare the team for multiple versions of it.
A great workshop connects purpose to action, turns chaos into clarity, and transforms short-term urgency into sustainable momentum.
