Twenty-Two Questions To Ask Before You Sign

THE TOOLKIT 

This toolkit is the companion piece for anyone who wants to go deeper into the tools and ideas we shared in our newsletter about designing a good partnership. Use it as a practical next step, not just a read.

Twenty-Two Questions To Ask Before You Sign 

Keep this. Use it on the next partnership someone brings you while everyone is still excited. 

Part 1 — Ask these alone, before anyone else is in the room 

1.  What can I only get through a partner, and could I get it faster by buying, hiring, or contracting instead? 

Why you ask it: Tests whether a partnership is the right instrument at all. Many alliances exist because someone liked the idea of one. 

2.  What happens to my business if this partnership never exists? 

Why you ask it: Names your real alternative. It sets the price of every concession you are about to make. 

3.  What is the smallest version of this that would still be worth doing? 

Why you ask it: Creates a floor. Enthusiasm inflates scope, and inflated scope is what makes exit expensive later. 

4.  Which of my people, customers, and intellectual property will be exposed to this partner? 

Why you ask it: Inventories what is actually at risk while it is still easy to ask. In month nine the same question sounds like an accusation. 

Part 2 — Ask these separately, then compare the answers 

5.  Why do you want this partnership, in your own words, not the press release? 

Why you ask it: Separates the motive from the announcement. Every later disagreement traces back to a motive somebody never stated. 

6.  Two years in, what does success look like for you specifically? 

Why you ask it: Surfaces divergent definitions of success while they are still cheap to reconcile. 

7.  What will you have to give up for this to work? 

Why you ask it: Reveals which concessions each side has already priced in, and which ones they have not noticed yet. 

8.  What is genuinely non-negotiable for you, and what only feels that way today? 

Why you ask it: Distinguishes real constraints from opening positions before either hardens into pride. 

Part 3 — The assumption audit: write these down separately, then exchange the pages 

9.  What do you believe you contribute to this partnership, and what do you believe we contribute? 

Why you ask it: The single highest-yield exchange on this list. Each side almost always believes it brings more. Better to see the gap in writing in month one than to hear it in a meeting in year three. 

10.  What must be true about the market for this to work? 

Why you ask it: Converts a shared bet into named, testable conditions that can be reviewed instead of argued about. 

11.  Whose customers are these, and who owns the relationship after we launch? 

Why you ask it: Channel conflict is among the most frequent causes of partnership breakdown and among the least discussed at formation. 

12.  Whose people will actually do the work, and who do they report to? 

Why you ask it: People expectations are rarely negotiated and reliably contested. Secondments, key-person commitments, and reporting lines belong on the table. 

13.  What are we each assuming that, if wrong, would break this? Would you bet on it? 

Why you ask it: The betting question separates conviction from habit. Anything you would not bet on should become a term that adjusts, not a hope. 

Part 4 — Ask these jointly: how we will notice trouble 

14.  What will we measure about the relationship, not only about the revenue? 

Why you ask it: Financial metrics lag. Relationship metrics lead. By the time the numbers show the problem, the trust to fix it is gone. 

15.  Who owns the health check, and how often does it happen? 

Why you ask it: A review nobody owns is a review that only happens after the damage. Put a name and a date on it. 

16.  What is the escalation path when two of our people disagree? 

Why you ask it: Builds a ladder from operators to alliance managers to the steering committee, so small disputes stop before they reach two CEOs. 

17.  Who is allowed to tell us this is not working? 

Why you ask it: Creates a legitimate channel for bad news. Often the honest answer is nobody, which is itself the finding. 

Part 5 — Ask these while goodwill is at its highest 

18.  Under what conditions would each of us want out? 

Why you ask it: Produces real termination triggers instead of the generic clause a lawyer will paste in at the end. 

19.  What must each of us protect on the way out? 

Why you ask it: Forces the list that matters at dissolution: intellectual property, customers, people, brand. It is unwritable once the relationship sours. 

20.  How do we break a genuine deadlock, and what stops either of us from using that mechanism as a weapon? 

Why you ask it: Buy-sell mechanisms favor whoever has more money. Notice periods, financing requirements, and a credible valuation method are what keep them fair. 

21.  What happens to whatever we build together? 

Why you ask it: Separates what each side brought in from what the partnership creates. Ambiguity here is where the most value quietly leaks. 

22.  What is the worst dissolution scenario you can imagine, and what would it cost you? 

Why you ask it: The fear question. It gets the most candid answers of anything on this list, and it tells you exactly what to design against. 

How to use it: Questions 1 to 4 are yours alone. Questions 5 to 13 are asked separately of each side and then exchanged in writing, because the value is in the gap between the two documents. Questions 14 to 22 belong at the table, together, before the term sheet exists. If a counterpart will not sit through Part 5, you have learned something more useful than any answer they could have given you.