Yes, this will be YOU one day!
I always like to write about what my sellers are experiencing in real time – and right now, I have a couple who are facing a great “problem” to have: choosing between two excellent offers.
Why just two? Sure, it’s possible to receive more than two offers, but once you factor in culture fit, your personal geography (where you are located), and future opportunities for you and your team, the list usually narrows to a final two.
My job as the seller’s M&A advisor is to negotiate those top two offers to be so close in price and terms that the decision is no longer about money.
So, if it’s not about the money… what do you base your decision on?
Let’s Get Real: It Becomes Personal
In situations like this, we go beyond the spreadsheets and get into soul-searching conversations about life goals – for both you and your team. Here’s what typically comes up:
1. Age and Stage of Life
This is where most conversations begin: Who’s staying, and how long?
Age often shapes how you think about your future role. Sellers in the 40–55 range tend to have gas left in the tank. They’re ready for the next bite of the apple – maybe as a partner in a new venture or in an executive role at the acquiring company.
But sellers 55+ often prioritize how quickly they can transition out and whether a second bite of the apple even matters at this stage. Some buyers offer fast exits; others expect multi-year commitments. That alone can tip the scale.
2. Compensation & Incentives
If you plan to stay, then salary, bonuses, and equity incentives become key decision points.
One common issue? Many owners keep salaries low (and take distributions) to manage EBITDA. But if you’re staying post-close, this is the time to negotiate a market-rate salary – especially if it won’t negatively impact normalized earnings.
In some cases, I’ve seen highly sought-after CEOs command not just higher purchase prices, but also personal incentive packages that include performance bonuses and additional stock beyond any rollover equity.
3. Your Go-Forward Role
Let’s be honest: not every founder is built to work for someone else.
Even in a platform deal, things will change. If you’re not being sold as a platform company, you likely won’t remain CEO. You might report to someone else, and your tried-and-true systems and SOPs may get replaced.
Some sellers thrive in their new roles. Others quickly feel the weight of middle management with no real say – and regret staying on.
Be honest with yourself:
- Will you be happy not calling the shots?
- Can you thrive under a new leadership structure?
- Are you energized by the idea of building within someone else’s vision?
Ask your buyers about your future role. If they can’t articulate it clearly, consider that a red flag.
4. Taking Care of Your Team
When two offers are equal, how the buyer treats your management team can become the deciding factor.
Most PE deals allow only owners to roll equity, making equity a taxable event for employees unless handled carefully. But there are creative solutions:
- Some sellers absorb the tax hit as part of the deal.
- Some buyers will split or cover the tax entirely.
- Many PE firms offer Management Incentive Units (MIUs) that carry no tax burden at the time of allocation.
When you’re evaluating offers, negotiate a pool of MIUs that you can allocate post-close. It’s one of the best ways to reward and retain key team members—and it speaks volumes about a buyer’s commitment to your people.
Conclusion: The Best Offer Isn’t Always the Biggest
When you’re fortunate enough to have two great offers, choosing the right one means digging deep into your long-term goals—for yourself, your family, and your team.
While valuation, structure, and earn-outs are critical, your day-to-day reality post-close may matter even more:
- Who will you report to?
- What will your role really look like?
- How will your team be treated?
- How soon can you transition out (if that’s your goal)?
The best offer is the one that aligns with the life you want after the close.
So, when that day comes – and it will – you’ll be ready to make the decision not just with your wallet, but with your eyes wide open.
Make sure you read my earlier post on the 6 points to consider when choosing between offers for more insights on this topic.
Need Naked Tail…Insurance?