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Three-quarters of the work to sell a business happens long before the first meeting with a buyer. Our interim executives, who have taken dozens of companies to exit, share their insights and the cautions they’ve learned along the way.
We asked the interim executives on our RED Team, leaders who have collectively taken dozens of companies to exit, a simple question: What does it actually take to get to a sale?
The answer was a 192-step roadmap.
Those 192 steps break into six distinct stages.
Stage 1. Making the Decision to Sell
The critical question to ask yourself at the start of this journey: What’s your motivation for selling?
The answer to that question determines who buys, how fast, and for how much.
Then, the key to getting the best deal is timing your exit around market appetite and at least two quarters of verifiable upward momentum. That allows you to set valuation expectations based on recent comps.
As interim exec Phil Morettini put it: Take the emotion and excitement out of the decision.
2. Prepare Before Hiring an Advisor
Keep early deliberations confidential and align your stakeholders, including family and board. Alignment matters because, as interim executive John Zombolas notes, most deals never happen.
This stage, which ideally happens 12 to 24 months before the target sale date, is also the time to begin the valuation enhancement process.
Score your business on 15 value drivers, from customer concentration to owner dependence. Next, clean up the lawsuits, unprofitable lines, and working capital problems that quietly erode proceeds.
The last steps of this stage ask you to look at your business as a potential suitor would so you can understand how buyers will actually value you.
Now, it’s time to line up experienced transaction counsel and an investment banker.
3. Choose Your Advisors
In this short but critical stage, you’ll choose the bankers and advisors who will shepherd your deal through to close. Ask for recommendations on bankers that would want you as a client and start informal talks with industry- and size-appropriate bankers, investment advisors, and external valuation companies so you can hire the right people six to nine months ahead of your target date.
Do not skip this stage, InterimExecs CEO Robert Jordan says.
I don’t think sellers going to market without a banker do any better. Likely, they do far worse.
-Robert Jordan, InterimExecs CEO
4. Prepare for Market and Diligence
This 92-step stage can feel like a slog.
It covers:
- The deal team and communications plan: Who knows, who doesn’t, and what each group hears and when. Assume the news will leak.
- Records, operations, and people: Audit financials, clean tax returns, document SOPs, sign retention agreements for key employees, and move personal expenses out of the business. As interim exec James Pitak says, “Nohing chases away buyers faster than messy accounting.”
- The financial model: Develop monthly statements, normalized earnings, and best, likely, and worst-case scenarios, because buyers won’t pay for value they create after close.
- The story: Create an investment narrative, not an asset list. Every buyer will also expect an answer on AI.
- The data room, legal cleanup, and buyer list: Appoint a data steward early, resolve the sale-stoppers, and build a target list of strategic and financial buyers.
- The operations: Keep the company operating at top capacity by engaging an interim CEO, CFO, or COO to focus on operations or, conversely, engage them to manage the sales strategy so your operating executives can stay focused on business needs.
5. Go to Market and Negotiate
Once you launch, urgency is everything, says interim exec Doug Olds, because “delays often favor the buyer as it provides more time for negative events to occur.”
Keep the news cycle positive and hit your projections. Run a roadshow, collect first-round bids, and aim to keep at least two suitors “to provoke the first into a transaction,” says interim exec Owen Carton.
Don’t take the first offer, focus on cash at closing rather than milestones that rarely pay out, and craft earnouts carefully. Above all, don’t get greedy late in the deal. Our contributors have seen too many good deals fall apart that way.
6. Close and Transition
The deal isn’t done until the money is in the bank. Form a transition team, document your know-how so it transfers to the buyer rather than out the door with you, tell customers your intentions, and plan the IT and operational integration, which might require an interim CIO experienced in combining tech stacks.
The Hidden Cost: Transaction Drag
A sale can consume your best people for months, and a distracted leadership team can erode the very value you’re trying to sell. That’s why our contributors repeatedly recommend interim leadership to fill critical gaps and keep the business running while management focuses on the deal.
Selling often takes longer than expected, and the business can’t pause while it happens.
Get the Full Roadmap
You can walk through all 192 steps, with expert commentary from 56 interim executives, in our full checklist of steps to sell your business.
Our Experts
These 56 RED Team interim executives built the list:
Adam Boris, Amy Mosser, Anthony Gargiulo Jr, Anthony Hartman, Babs Ryan, Bill Mince, Buddy Willard, Dan Weinfurter, David Esposito, David Sheehan, Dennis Cagan, Don McIsaac, Doug Olds, Frank Tsai, Gregory Kalush, Ian Smith, Jack Didinger, James Pitak, Jan Gensheimer, Jan-Patrick Schmitz, Jane Turlo, Jennifer Crews, Jeremy Sanders, Jim Long, John Racioppi, John Zombolas, Joshua Katz, Karma Israelsen, Keith Brooks, Kelly Haggerty, Kevin Coen, Kyle Murphy, Leah Bailey, Len Chermack, Lloyd A. Perlmutter, Mark Brewer, Mark Nechita, Mike Capetanakis, Narasimha Krishnakumar, Nora Baker, Owen Carton, Peter McCann, Peter Wokwicz, Phil Morettini, Ralph Shayne, Rich Bialek, Robert Jordan, Ron Herardian, Russ Reeder, Sharon Ephraim, Sri Srinath, Steve Hummel, Steve Vivian, Susan Rittscher, Vini Meirelles, and Zeeshan Kazmi.
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Frequently Asked Questions
Our interim executives, who have taken dozens of businesses to exit, have found that the most profitable exits happen when owners spend 12 to 24 months identifying valuation gaps, diversifying customer concentration, removing owner dependencies, and cleaning up financial statements. Doing this groundwork early prevents costly retrading, accelerates due diligence, and puts you in the driver’s seat during negotiations.
Transaction drag occurs when a founder or C-suite team becomes so consumed by running the deal—answering due diligence inquiries, populating data rooms, and meeting prospective buyers—that daily operations falter. If revenue dips or milestones are missed while under a Letter of Intent (LOI), buyers get nervous and often cut their offer. Bringing in experienced interim leadership to run operations or lead the transaction prep protects core business performance and maintains deal momentum.
Ideally, formal exit preparation should begin 18 to 24 months before you plan to go to market. This timeline gives you sufficient runway to run a comprehensive valuation enhancement process, transition to auditable accrual accounting, settle lingering legal or tax liabilities, and build out a sustainable leadership team that proves the business can thrive without you.
Investment bankers and brokers are outside advisors who focus on the sale, valuing the business, marketing the deal, and negotiating with buyers. Interim executives can be engaged to work on the deal, but they also can be engaged to focus inward. Either way, they become an integral part of the C-suite. They embed directly into your leadership team to fix operational bottlenecks, clean up messy financials, build out virtual data rooms, and manage daily business performance so existing leadership doesn’t burn out. Rather than brokering the sale, an interim executive optimizes the company so the banker can command the highest possible multiple.
Getting greedy or attempting to retrade on agreed terms late in the process. Once an LOI is signed and diligence is winding down, deal fatigue sets in on both sides. Introducing unexpected demands, stalling over minor points, or trying to squeeze out extra concessions often damages trust and gives the buyer an excuse to walk away or renegotiate downwards. Aiming for a firm, fair close with clear transition terms protects the deal and ensures funds actually hit the bank.
