Most strategy sessions are theater.
Three hours in a conference room. A whiteboard full of aspirations. Maybe some Post-it notes about “customer centricity” and “market leadership.” Then everyone leaves, and exactly zero executable plans exist.
The problem isn’t that teams lack strategic thinking. It’s that most business strategy frameworks start in the clouds and never touch ground. Or they start with today’s fires and never lift their heads to see where they’re actually going.
I learned a different approach 25 years ago at the Air Force Academy, training to become an officer in what was then the early days of information warfare. We didn’t start with vision statements or OKRs. We started with maps.
That instinct—to visualize the battlefield before you move—has shaped every strategy I’ve built since. Whether I’m working with a fintech founder trying to break into mortgage lending or a B2B SaaS company fighting for market share, the pattern is the same.
Strategy isn’t about being the smartest person in the room. It’s about seeing the terrain clearly, understanding your resources honestly, and building a path your team can actually walk.
Here’s the framework I use.
The Two Strategy Mistakes Killing Your Momentum
Before we get into the framework, let’s talk about why most strategies fail.
Mistake #1: Getting pulled into immediate issues with fake urgency
Last month, I watched a CEO spend 45 minutes in a strategy session debating whether to switch project management tools. The real strategic question—whether they should pivot their ICP from mid-market to enterprise—never got addressed.
We drift toward easy problems. Familiar routines. Tactical fires that feel urgent but aren’t strategic. Meanwhile, the hard questions—the ones that actually determine whether you win or lose—sit untouched.
Mistake #2: Ascending into the clouds and forgetting where you are
The opposite mistake is equally deadly. I’ve seen teams build beautiful strategies for companies that don’t exist. They map out five-year plans that require teams they don’t have, budgets they can’t access, and market conditions that won’t materialize.
Strategy requires alternative thinking, but it can’t ignore current reality. You have to start from where you actually are—not where you wish you were.
The framework below solves both problems. It forces you to see reality clearly while thinking differently about where to go next.
Step 1: Map the Battlespace (Not the Vision)
Back at the Academy, every wargaming exercise started the same way: we’d study a map of the battlefield. Later, as I moved into information warfare, we called this the “battlespace” as war became more multi-dimensional and digitized.
The principle translates directly to business strategy. Before you decide where to go, you need to see where everyone currently stands.
I want a visual map of the competitive landscape. Not a spreadsheet. Not a list. A map.
Here’s what goes on it:
- Every meaningful competitor in your space
- Their market position and perceived influence
- Their messaging and positioning strategy
- Their key differentiators (real or claimed)
- Geographic or vertical focus areas
Why this matters:
A collaborative battle map session does two critical things. First, it aligns everyone’s mental models. Your VP of Sales sees the competitive landscape differently than your CMO. Your product team has different intel than your founder. Getting it all on one map surfaces the gaps.
Second, it reveals hidden knowledge. Someone on your team knows that Competitor X just lost their head of sales. Someone else knows Competitor Y is running out of runway. When you map the battlefield together, this intelligence emerges.
According to research on strategy mapping, visual representations surface gaps and opportunities that aren’t obvious in spreadsheets. More importantly, they make strategy discussions concrete instead of abstract.
How to Actually Do This
Don’t:
- List competitors in a spreadsheet
- Guess at their positioning without research
- Do this exercise alone in your office
Do:
- Plot competitors visually by market position and strength
- Research their actual messaging, funding, and market presence
- Make it a collaborative workshop with key stakeholders
- Update quarterly as the battlefield shifts
I typically use a simple whiteboard or Miro board with two axes: market presence (x-axis) and capability/strength (y-axis). Every competitor gets plotted. Every position gets debated. By the end, everyone sees the same terrain.
Step 2: Map Resources (Yours and Theirs)
Understanding positioning isn’t enough. You need to understand resources—who has what, and how long they can sustain their current strategy.
This is often where winners and losers are determined. Strategy isn’t just about taking ground. It’s about taking and holding ground. That requires resources.
The Resource Assessment Framework:
For each major player (including yourself), inventory:
1. Cash position – Who can outlast a price war? Who’s well-established and cash-flowing predictable revenue? Who has a war chest of investor capital? Who’s running out of runway or overleveraged?
2. Human capital – Who has the talent density to innovate faster? Who’s bootstrapped and resourceful? Who just lost their leadership team?
3. Distribution channels – Who owns the channels customers trust? Who has partnerships that create moats?
4. Brand equity and reputation – Who gets the benefit of the doubt? Who has trust built over decades? Who’s the scrappy upstart that nobody takes seriously yet?
This is often hard to assess fully, but even partial intelligence changes your strategy. If you know Competitor A is burning $2M/month with 8 months of runway, you know they’ll get aggressive on pricing soon. If Competitor B just raised a $50M Series C, you know they’re about to flood the market with sales headcount.
The Resource-Based View in strategic management emphasizes that competitive advantage comes from resources that are valuable, rare, hard to imitate, and well-organized. When you map resources against your battle map, patterns emerge: who’s vulnerable, who has strategic flexibility, and where the real competitive advantages lie.
“Resources aren’t just cash. They’re skills, distribution, reputation, and time. Map all of them—not just the obvious ones.”
Often this assessment reveals that you have advantages you’re not leveraging. Or it shows that the competitor everyone fears is actually more fragile than they appear.
Step 3: Build From Constraints, Not Dreams
Now that you understand the market you’re operating in, it’s time to look at your own situation honestly.
This is where most strategies go off the rails. Teams build plans for the company they wish they had, not the company they actually have.
I build every strategy from constraints up, not vision down. Here’s why: if you can’t identify a reasonable path from your current constraints to your objectives, you don’t have a strategy. You have a wish list.
The Constraint Inventory:
What raw materials do you have? List your actual resources—budget, team size, technical capabilities, existing customers, market relationships.
What tools or advantages do you have? Product features competitors don’t have. Unique data. Proprietary processes. Strategic partnerships. Don’t list what you could build. List what you have.
What skills or experiences do you have? Your team’s capabilities aren’t theoretical. What have they actually done before? What’s reasonable to build, upgrade, or improve in the next 90 days?
What’s your actual capacity? Not your theoretical capacity if everyone worked 60-hour weeks. Your real capacity given current commitments, technical debt, and human limitations.
I typically map these constraints on a simple spreadsheet before we touch any aspirational goals. Here’s what that looks like:
| Constraint Type | Current State | 90-Day Improvement Potential |
|---|---|---|
| Team capacity | 3 marketers, 40 hrs/week available | Can hire 1 coordinator (8-week ramp) |
| Technical capability | Can build basic integrations | Can add API specialist (4-week search + hire) |
| Market access | 5,000 email subscribers, 2,000 LinkedIn followers | Can add 1,500 qualified subscribers (content + ads) |
| Capital | $50K marketing budget/quarter | Can potentially increase 20% if ROI proven |
Here’s the critical part: I want built-in tests and points of validation. I don’t want to put an objective in the plan that doesn’t have a reasonable path and probability of getting there.
If your constraint is “we have three marketers and 40 hours per week of capacity,” your strategy can’t require 80 hours per week of marketing execution. Either you hire, you cut scope, or you admit the goal isn’t realistic.
This sounds obvious, but I’ve reviewed hundreds of strategic plans that fail this basic sanity check. They require teams that don’t exist, budgets that aren’t approved, and capabilities that would take years to build.
Real example from a client engagement:
A mortgage lender wanted to “dominate digital lead generation in the Western U.S.” within six months. Great goal. Completely unrealistic given their constraints:
- 1 marketing person (the founder’s nephew)
- $10K/month ad budget
- No email list, no content, no SEO presence
- No CRM or lead management system
We rebuilt the strategy from constraints up: “Generate 50 qualified mortgage applications per month from digital channels within 90 days, then scale.” That was achievable. We could hire one experienced digital marketer, implement a basic lead management system, and launch targeted campaigns in specific metro areas.
They hit the goal in 87 days. Then we scaled.
Step 4: Assign Ownership Before the Plan is Done
This is where I deviate from most strategists, and it’s the move that separates strategies that get executed from strategies that die in Google Docs.
As soon as I have a rough outline of the strategy, I start identifying people to own parts of the plan—before it’s fully fleshed out.
Here’s why this works:
The worst thing you can do is hand a team a finished strategy. They’ll immediately overwhelm you with questions, constraints, and excuses. They’ll put every problem on you to solve. Why? Because it’s your strategy, not theirs.
Instead, I want to make sure it’s our strategy. I want execution owners to feel empowered and accountable to flush out the details, solve the problems, and map the journey to the objective.
Here’s how this plays out in practice:
Once I have the rough strategic outline—we’re targeting these markets, with these offerings, using these channels—I bring in the people who’ll own execution. Not to present the plan. To build it with me.
The CMO doesn’t get handed a demand gen strategy. She gets brought in to help shape it based on what she knows about our channels, our content velocity, and our conversion rates.
The VP Sales doesn’t get handed a quota. He helps build the model based on what he knows about deal cycles, close rates, and team capacity.
The product leader doesn’t get handed a feature roadmap. She helps prioritize based on what she knows about technical feasibility and customer demand patterns.
This isn’t consensus-building theater. It’s practical strategy development. The people closest to execution constraints surface the real blockers before they become excuses.
Research on collaborative strategic planning consistently shows that strategies where execution owners help shape the plan have significantly higher success rates than top-down mandates. You’re not just building a better strategy—you’re building organizational buy-in and capability simultaneously.
I used to think that strategy required deep knowledge about the market or industry I’m supporting. But sometimes a bit of ignorance mixed with a lot of curiosity is often the best ingredients. The people closest to the work know things you don’t. Let them bring it to the table.
Step 5: Add One BHAG (But Only One)
Even though I’m a big believer in creating straightforward pragmatic plans, I think it’s essential to have one north star you’re trying to head toward.
Every strategy needs at least one BHAG—Big Hairy Audacious Goal.
You might not hit it. But I guarantee you’ll be much closer with it than without it.
The balance matters: Your constraint-based approach ensures you don’t build castles in the sky. The BHAG provides directional pull and prevents incremental thinking from dominating.
Here’s what makes a good BHAG:
| ❌ Bad BHAG | ✅ Good BHAG |
|---|---|
| “Become the market leader” | “Sign 100 enterprise customers in the mortgage lending vertical by end of 2026” |
| “Increase revenue” | “Hit $10M ARR with 40%+ gross margins within 18 months” |
| “Improve customer satisfaction” | “Achieve NPS of 70+ with zero customer churn in our top 50 accounts” |
Notice the difference. Bad BHAGs are vague aspirations. Good BHAGs are specific, measurable, and ambitious but not absurd.
The rule: One BHAG. Not five. Not ten. One.
If you have multiple BHAGs, you don’t have a strategy. You have a wishlist. Strategy is about choosing where to focus. That means choosing what not to pursue as much as what to pursue.
Your BHAG should be the thing that, if you accomplished it, would fundamentally change your competitive position. Everything else in your strategy should ladder up to that goal.
Jim Collins’ research on BHAGs from “Built to Last” showed that companies with clear, compelling BHAGs significantly outperformed their peers. The key isn’t just having a big goal—it’s having one big goal that everyone rallies around.
The Complete Framework (Quick Reference)
Let’s recap the five-step business strategy framework:
1. Map the battlespace – Create a visual representation of competitors, positions, and market dynamics. Make it collaborative to surface hidden knowledge and align mental models. Update quarterly as conditions shift.
2. Assess resources – Go beyond cash to inventory skills, tech, relationships, and reputation for each player (including yourself). Use a simple scorecard to understand who’s vulnerable and who has strategic flexibility.
3. Start with your constraints – Build realistic plans from what you actually have, with built-in validation points and reasonable growth patterns. If you can’t trace a path from current constraints to stated objectives, revise the objectives.
4. Assign ownership early – Get execution owners involved before the plan is finalized. Let them shape the details based on what they know about real-world constraints and capabilities. Make it “our strategy,” not “your strategy.”
5. Add one BHAG – Balance pragmatism with exactly one visionary goal that provides directional pull and prevents incremental thinking. Make it specific, measurable, and ambitious but achievable.
Strategy doesn’t have to be complex or abstract. Keep it visual, grounded in reality, collaborative, and adaptable. That’s how you build plans that teams actually execute—and that’s how you win.
What This Means for You
If you’re leading a team between 20 and 200 people, you’re at the inflection point where strategy actually matters. You’re too big to wing it, but small enough that bad strategy can kill you in two quarters.
The good news: you don’t need an MBA or a $50K strategy consultant to build executable plans. You need a framework that starts with reality, involves the people who’ll execute, and balances pragmatism with ambition.
The companies winning in your space aren’t doing 10x more strategy work. They’re doing it differently:
- They map the competitive landscape visually before making moves
- They inventory resources honestly (theirs and competitors’)
- They build from constraints up, not vision down
- They assign ownership before plans are final
- They pick one big goal and build milestones toward it
Your competition is probably spending this quarter in strategy meetings that produce PowerPoints nobody reads. You don’t have to.
“Strategy isn’t about being the smartest person in the room. It’s about seeing the terrain clearly, understanding your resources honestly, and building a path your team can actually walk.”
Start with the battlespace. Map what’s real. Build from constraints. Involve your team early. Pick one big goal.
That’s strategy that actually works.
Need help building a strategy your team will actually execute? I work with fintech founders and B2B leaders to turn strategic aspirations into executable 90-day plans. Schedule a discovery call to map your path from here to there.
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