Exit planning isn’t just a financial or legal exercise — it’s a strategic one. And like any strategy, it benefits from structure, reflection, and intentional goal-setting. That’s where planning frameworks like SWOT analysis and OKRs (Objectives and Key Results) come into play.
In my journey building and exiting multiple businesses — most notably Pepperjam, which was acquired by eBay in 2009 — these tools helped bring clarity and control to what can otherwise be a chaotic, emotional process. Today, through Legacy Advisors and our podcast, we guide founders through these same frameworks to help them exit on their terms.
In this article, I’ll walk you through how to use strategic planning tools to guide your exit prep — not just tactically, but as part of a broader vision for unlocking value and attracting the right buyer.
Why Strategic Planning Matters in Exit Preparation
Too often, founders think of exit planning as something that happens in the final 6–12 months before a sale. But that’s backward. The most successful exits are engineered years in advance, shaped by clear goals, structured thinking, and regular checkpoints.
Strategic planning tools give you:
- A framework to assess where you are
- A language to communicate goals with your team and advisors
- A lens to prioritize what truly moves valuation
- A feedback loop to keep you aligned over time
Let’s dive into the two most powerful tools we recommend: SWOT and OKRs.
Using SWOT Analysis for Exit Strategy Planning
What is SWOT?
SWOT stands for Strengths, Weaknesses, Opportunities, and Threats. It’s a classic business analysis tool used to assess both internal and external factors that affect your strategic position.
While it’s often used in early-stage planning, SWOT is extremely powerful in exit preparation when used with exit criteria in mind.
How SWOT Supports Exit Prep
Strengths
This is your chance to spotlight the core drivers of valuation. Ask:
- What assets or capabilities give us a competitive edge?
- What are buyers likely to see as our moat?
- What customer love or loyalty can we prove?
In my Pepperjam exit, we identified our brand equity, affiliate network, and team culture as key strengths. We invested in amplifying these before sale.
Weaknesses
This is where you identify friction and risk from a buyer’s perspective.
- Where are we founder-dependent?
- What financial or operational gaps exist?
- What areas might cause concern in due diligence?
Remember: weaknesses become leverage points for buyers if you don’t address them.
Opportunities
This is your “what’s next” section — and it’s gold for buyer narratives.
- What product expansions or verticals are we poised to dominate?
- What strategic partnerships or markets are emerging?
- What use cases are underdeveloped but high potential?
A SWOT-aligned narrative helps buyers envision the upside post-acquisition.
Threats
Think proactively about what could erode valuation.
- Are there looming competitors with more capital?
- Are there legal, regulatory, or IP risks?
- Could market trends reduce demand?
Use this section to build a risk mitigation plan, not just a risk list.
When to Use SWOT in Exit Prep
- Annually as part of strategic planning
- Two years out from a target sale date
- Before engaging advisors or bankers
- As part of CIM development to shape positioning
Applying OKRs to Exit Readiness
What Are OKRs?
OKRs stand for Objectives and Key Results. Popularized by Google and other high-growth companies, they’re a goal-setting system that aligns teams around measurable, time-bound priorities.
Here’s how they break down:
- Objectives: Clear, ambitious goals that inspire
- Key Results: Quantifiable outcomes that track progress
OKRs create focus and accountability — two things every founder needs in exit mode.
Structuring OKRs Around Exit Goals
Here’s how to turn exit prep into actionable OKRs across different departments.
Objective: Increase company attractiveness to strategic buyers.
- KR1: Grow MRR by 20% in vertical X (strategic segment)
- KR2: Reduce customer churn from 15% to under 10%
- KR3: Build 3 new strategic partnerships with ecosystem players
Objective: Strengthen operational resilience ahead of due diligence.
- KR1: Hire VP of Finance to lead audit readiness
- KR2: Document 100% of client contracts and SOPs
- KR3: Reduce founder-led sales from 80% to below 25%
Objective: Improve valuation-driving metrics.
- KR1: Increase NPS from 45 to 60
- KR2: Raise gross margins from 58% to 65%
- KR3: Decrease CAC payback period from 12 to 8 months
OKRs Are Not Just for Startups
Even established companies preparing for a sale benefit from OKRs. Why?
- They force prioritization — no chasing vanity metrics
- They connect team execution to strategic outcome
- They create a scoreboard you can show buyers
OKRs keep everyone rowing in the same direction — and that direction is toward a clean, compelling exit.
Combining SWOT and OKRs: A Real-World Example
At Legacy Advisors, we recently worked with a tech-enabled services firm preparing for an exit within 18 months. Their SWOT revealed:
- Strengths: Proprietary platform, long client tenure
- Weaknesses: Heavy founder involvement in ops
- Opportunities: Emerging demand in healthcare vertical
- Threats: Two new well-funded competitors entering the space
Using that analysis, we helped them build quarterly OKRs:
- Hire and onboard Director of Ops (reduce founder dependency)
- Launch v2 of platform tailored for healthcare clients
- Sign 2 lighthouse healthcare clients within 6 months
- Migrate 80% of customer service tickets to Zendesk
These actions led to a successful acquisition by a private equity-backed roll-up, 14 months later.
How Strategic Planning Affects Valuation
Here’s the truth: buyers don’t just want performance — they want predictability and professionalism. Strategic planning signals:
- Organizational maturity
- Cultural alignment
- Operational discipline
- Leadership credibility
When buyers see a clean SWOT, aligned OKRs, and execution data, they assume a smoother transition — and that means more cash up front and fewer earnouts.
How to Kickstart Strategic Planning for Exit
- Set a target exit window (even if it’s 2–3 years out)
- Facilitate a SWOT session with founders and key leaders
- Define 1–3 strategic objectives that align with valuation drivers
- Assign measurable KRs across marketing, ops, sales, and finance
- Review quarterly and adjust as you learn
- Document your wins — they’ll go straight into your CIM
You don’t need a Bain-level strategy offsite. You need clarity, accountability, and rhythm.
Final Thoughts
A great exit is a designed outcome, not a lucky break. If you want to sell for what you’re worth — or more — you need more than traction. You need a strategic foundation that proves you’re worth acquiring.
That starts with:
- A clear SWOT that identifies your assets and gaps
- Focused OKRs that close those gaps and drive valuation
- A team aligned behind the mission — and ready for the opportunity
Exit planning isn’t a secret. It’s a discipline. Use the tools. Create the rhythm. Control your narrative.
Because when the right buyer comes along, you’ll be ready — and they’ll know it.
Frequently Asked Questions About Using Strategic Planning Tools to Guide Exit Prep
How can SWOT analysis improve the success of an exit strategy?
SWOT analysis provides a structured way to evaluate both the strengths you can leverage and the weaknesses you must address before a sale. It helps founders look at their business through the eyes of a potential buyer — revealing risks, differentiators, and opportunities for value creation. For example, identifying founder dependency as a weakness lets you prioritize leadership hiring before due diligence begins. SWOT also frames your company’s story in a way that buyers appreciate: strong internal assets, market opportunities, and well-managed threats. By regularly updating your SWOT in the years leading up to exit, you’re proactively shaping valuation and buyer confidence.
Why are OKRs especially valuable when preparing for a business exit?
OKRs turn strategic objectives into measurable, actionable priorities — which is essential when preparing for a complex process like a business exit. They help ensure that every department is aligned with the broader mission of maximizing valuation and reducing acquisition risk. From improving customer retention to reducing founder involvement, OKRs make intangible goals tangible. Buyers love seeing OKRs because they reflect operational maturity, team discipline, and a data-driven culture. It shows that your company doesn’t just talk about growth or readiness — it tracks it. This level of transparency and goal accountability can help streamline negotiations and increase trust in the deal process.
When should a founder start using SWOT and OKRs to plan for an exit?
The best time to begin using SWOT and OKRs to guide exit prep is 18 to 36 months before you want to sell. That window gives you time to make meaningful improvements to valuation drivers and remove red flags that could stall or reduce an offer. Starting early also ensures that these tools are embedded in your culture — not just used as window dressing. You’ll be able to track progress, course-correct, and demonstrate improvements across multiple quarters. In fact, many of the most successful exits I’ve seen involved companies that began planning at least two years out and used these tools continuously.
How do these tools impact the buyer’s perception during due diligence?
Buyers are looking for signs of consistency, clarity, and professionalism. A company that presents a clean SWOT analysis and OKRs aligned with growth and exit milestones tells a very clear story: “We know who we are, where we’re going, and how we get there.” This gives buyers confidence not just in your business model, but in your team’s ability to execute during and after the transition. It also minimizes surprises, which is crucial in due diligence. Buyers are far more likely to pay a premium when they believe the seller is competent, proactive, and prepared — and these tools provide that proof.
What’s the biggest mistake founders make when using these tools in exit planning?
The most common mistake is using SWOT and OKRs as one-off exercises rather than integrated, ongoing systems. A SWOT that sits in a drawer or OKRs that never get reviewed won’t impact your exit readiness. These tools are only effective when they shape real decisions, drive prioritization, and are shared with your leadership team. Another mistake is failing to align these tools with the buyer’s lens. If your OKRs focus only on top-line growth and ignore risk mitigation, you’re missing the opportunity to position the company in the most compelling way. Used correctly, these tools are not just internal trackers — they’re valuation levers.