Before You Say “Yes” To A Business Partner: 4 Questions That Saved Me

Research cited by Harvard Business Review ties roughly 65% of startup failures to cofounder conflict. That’s not rare—that’s the norm when you get this wrong.

At the same time, about half of new U.S. employer businesses don’t make it to year five—so if your partnership cracks, your business odds drop even more.

And while it’s a different context, corporate alliances between established companies fail 60–70% of the time. Translation: collaboration at the top level is hard—and you should plan like it is.

Below are the four filters I used before choosing my partner, Ron—and the guardrails we put in place so the relationship strengthens the business instead of sinking it.

1) What does God think?

I fasted for 24 hours and prayed—not “Should I do this?” but “Give me a reason NOT to.” I wanted a safeguard against excitement blinding judgment. As a guiding principle: “Watch over your heart with all diligence, for from it flow the springs of life.” (Proverbs 4:23)

Try this: fast (even a meal), pray, and write down only red flags. If none rise to the surface, you’ve passed the first filter.

2) Is he a man of integrity?

I met Ron 15 years ago. Under pressure and office politics, he chose the right thing—consistently. Integrity isn’t proven when everyone agrees; it’s proven when it costs you.

How to assess:

• Ask for three situations where they chose principle over popularity.

• Talk to former bosses, peers, and direct reports—look for consistency across roles.

• Give a small, high-trust task with ambiguity and a deadline. Watch how they handle it.

3) Do our skills complement—not clone?

Two captains sink a ship. Ron brings agency-building, training, and asset-protection expertise. I bring building, sales/marketing, leadership, and the tech stack. Overlap is fine; duplication is not.

Practical move: Map skills in a simple 2×2—Growth, Ops, Finance, Product/Service. Assign a DRI (Directly Responsible Individual) for each and write it into your agreement.

4) Do our personalities fit under feedback?

I’m intense—Ron’s chill. But here’s the tell: when I asked for permission to be brutally honest if he sucks at something, he leaned in. Low defensiveness is priceless.

Stress-test fit:

• Run a “hard feedback” drill—deliver direct critique and see how each person responds.

• Share your worst-case scenario about working together; ask them to do the same.

• Agree on a conflict ritual (see below).

Build the guardrails before you build the brand

Even great partners need structure. Put these in writing now:

• Roles & decision rights. Who decides what, and how do you break ties?

• Founder vesting. Standard practice is 4-year vesting with a 1-year cliff so equity is earned over time—protects both sides if someone leaves early.

• Buy-sell & deadlock. Include a shotgun clause (the “I name the price—you choose buy or sell” mechanism) as a last-resort way to break 50/50 paralysis. I

• Dispute ladder. Written steps: 1) cool-off, 2) live discussion, 3) mediated session, 4) binding arbitration.

• Cadence. Weekly leadership sync, monthly KPI review, quarterly offsite—on calendar now.

• Values non-negotiables. Integrity, transparency, bias to action, low ego—define behaviors you will and won’t tolerate.

A quick pre-partnership checklist

• We’ve prayed/paused and tried to “talk ourselves out” of it first.

• Our skills are complementary, and DRIs are assigned in writing.

• We’ve exchanged hard feedback and handled it like adults.

• Our operating agreement includes vesting, buy-sell, deadlock, and dispute provisions.

• We’ve scheduled weekly, monthly, and quarterly partner check-ins.

Why this level of rigor?

Because partnerships amplify everything—good and bad. When cofounder relationships fracture, companies die at alarming rates. Build the partnership on principle, structure, and truth-telling—and your odds improve dramatically.

What question would you add before partnering?