5 Execution Risks That Blow Up Post-Close (That Financial Diligence Can’t Catch)
Financial diligence is critical.
But it won't tell you if the ops manager is the margin. Or if the founder is still running the company from the parking lot. Over the past year, we’ve helped dozens of searchers and investors dig into what’s beneath the surface of a "good deal."
Here are five patterns we keep seeing, and how to spot them before they cost you real money.
1. You’re Not Buying the Org Chart
You’re buying the actual power structure. And it usually isn’t on paper.
Most founder-run businesses rely on a few linchpin people who control decisions, customer relationships, pricing exceptions, or vendor coordination. These roles often aren't documented and rarely cross-trained. If “Barb” leaves, the invoicing collapses. If “Steve” is sick, jobs don’t get scheduled.
What to ask:
Who touches every quote, every invoice, or every major decision?
If that person quits tomorrow, what breaks?
2. Marketing Isn’t Missing — It’s Invisible.
Many sellers say, “We don’t do any marketing.” That’s almost never true.
It’s just informal: vendor referrals, handshake deals, legacy relationships. No CRM. No pipeline. No predictable engine. When the founder steps out, so does the growth.
What to ask:
Where did the last 5 new customers actually come from?
If referrals stopped tomorrow, what would the next lead be?
3. The Product or Service Catalog is Killing You.
Businesses with 20+ SKUs or service types often only make money on a few. The rest? Operational drag.
Too many offerings means more quoting errors, longer onboarding, higher COGS, and slower sales. But most owners are emotionally attached to what they built.
What to ask:
What are your most profitable 3 offerings?
Which services do you secretly hate delivering?
4. The Team Isn’t Aligned.
The seller says the team will stay. The team isn’t so sure.
Most employees don’t know what happens post-close. They worry. They stall. And if they don’t know who’s in charge on Day 1, they default to confusion or churn.
What to ask:
Have you told your team you're selling?
What are their questions, and do you have the answers?
How will they be communicated to about the change in ownership, organization, and overall changes to the business?
5. The Founder Never Really Leaves.
Even if the documents say they do.
Many sellers don’t intend to interfere. But they can’t help it. They’re emotionally tied in. Customers keep calling them. Vendors ask what’s changing. The team waits for their cues.
What to ask:
Who will customers call after the deal closes?
What does "transition support" actually mean, and who defines it?
Want a checklist version of these questions?
Want help evaluating a target? Explore our Operational Readiness & Transition Support services.