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Lani Dickinson, Founder of Stealth and host of the Freedom To Exit Podcast, sharing expert business exit strategies and recurring revenue insights.

Key Man Risk: Your Business’s Silent Killer

March 18, 20254 min read

The One Thing That Could Kill Your Exit Deal

You’ve done the work. You’ve built the team, grown the revenue, and maybe even taken a few well-deserved vacations. But if your business depends too much on you—or just one or two key people—it might not be a business at all. It’s a liability.

Key Man Risk is one of the most silent but deadly threats to your business’s sellability. And most founders don’t even realize it’s there until the buyer pulls out... or slashes their offer.

What Is Key Man Risk—and Why Should You Care?

Key Man Risk is the potential that your business’s success (or survival) hinges on one individual: you or another critical team member. That’s a red flag for any serious buyer.

Think about it:

  • If you vanish for 30 days, would your business keep humming?

  • If your top salesperson, ops manager, or lead tech quits, do things fall apart?

  • Is all your client intel locked inside one person’s head?

If the answer to any of those is yes, your business has Key Man Risk. And that risk = reduced valuation, deal delays, or worse—no deal at all.

What Buyers Really Think

Buyers don’t want to inherit chaos. They want systems, stability, and a team that can run the show without you. If your departure—or the departure of a key player—would jeopardize operations, most buyers will do one of two things:

  1. Walk away entirely

  2. Offer a significantly lower price with heavy earnouts attached

And trust us, no founder wants to be trapped in a business they just sold, working under someone else’s rulebook.


How to De-Risk Your Business and Increase Its Value

Here’s what you need to do to eliminate Key Man Risk and turn your business into a sale-ready, scalable asset.

1. Get Yourself (and Your Face) Out of the Business

If you’re still the go-to for clients, approvals, or vision casting—it’s time to start removing yourself. This doesn’t mean disappearing tomorrow. It means creating a leadership team that can stand on its own.

2. Systemize and Document Everything

From sales to onboarding to client retention—make sure your processes are documented. Knowledge stuck in one person’s head is a ticking time bomb. SOPs (Standard Operating Procedures) aren’t sexy, but they are profitable.

3. Secure Key Person Insurance

This is a game-changer. Key Person Insurance is a life and disability policy the business owns on its critical people (including you). If something happens, the business receives a payout to cover losses, find replacements, or fund transition needs. It tells buyers: We’ve got a plan, no matter what.

⚠️ Common Mistakes:

  • Forgetting to get consent

  • Letting the policy lapse due to missed payments

  • Underinsuring (aim for 5–7x contribution value)

4. Create a Structured Retention Bonus Plan

Buyers want assurance that your top talent will stay after the sale. That’s where retention bonuses come in.

Here’s a proven structure:

  • Offer a bonus split over 3 years (e.g., $150K = $50K/year)

  • If the employee leaves early, they forfeit remaining payments

  • Stack this with existing annual bonuses for added incentive

This keeps your key people from jumping ship and ensures leadership continuity for the buyer.

5. Build a Pipeline of Talent

Don’t just rely on one rockstar. Cross-train your team. Develop a clear second-in-command. And make sure client relationships are distributed—not concentrated.


Start Fixing This Now—Not When You’re Ready to Sell

Here’s the truth: it takes 1–3 years to fully eliminate Key Man Risk. Buyers need to see a track record of stable, independent operations.

That means:

  • Strengthening your leadership bench

  • Implementing and using systems consistently

  • Keeping your team engaged with long-term incentives

Want to know if your business is too dependent on you or one key player?

👉 Take the Changes Assessment and find out exactly where your vulnerabilities are—and how to fix them before they cost you millions.


Free Resources to Go Further:

📌 7 Ways AI Can Boost Your Sales and Save You Time – Download this free guide:
👉 https://ai.activatetoascend.com/get-7ways-ai

📌 3 Ways Your Business Can Use AI TODAY to Stop Leaking Money – Save your seat for the free live webinar:
👉 https://webinar.activatetoascend.com/webinar-register-general

📌 Changes Assessment – Discover where your business is leaking time, money, and momentum:
👉 https://stealthfreedomtoexit.com/changes

Lani Dickinson is a former Fortune 175 CEO turned business strategist and founder of Freedom To Exit. With decades of executive leadership experience, Lani helps self-led entrepreneurs transform their companies into scalable, sellable assets—so they can achieve true time, location, and financial freedom. As the host of the Freedom To Exit podcast, she delivers straight-talking insights, powerful frameworks, and actionable strategies for business owners ready to exit for more.

Lani Dickinson

Lani Dickinson is a former Fortune 175 CEO turned business strategist and founder of Freedom To Exit. With decades of executive leadership experience, Lani helps self-led entrepreneurs transform their companies into scalable, sellable assets—so they can achieve true time, location, and financial freedom. As the host of the Freedom To Exit podcast, she delivers straight-talking insights, powerful frameworks, and actionable strategies for business owners ready to exit for more.

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