You structure a Series A. The term sheet is clean. The founder is diluted but keeps control, the lead investor gets standard terms, the angels roll over their notes. Everyone signs. Three months later you are on a call about the option pool: the founder thought it came out of post-money, the lead assumed pre-money, and the angels are furious nobody told them their percentage would drop again.
The deal structure was mapped. The stakeholder expectations were not. Every party read the same terms through their own lens, and you assumed they all understood it the same way. In fifteen years of transaction work, this is the failure I have seen sink more deals than any drafting error — not what the document said, but what each side believed it said.
Lawyers are trained on the mechanics: cap table, valuation, protective provisions. Necessary, not sufficient. A model helps here precisely because it is loyal to no one at the table — it will map the perspective of a party you do not represent, and name conflicts that are uncomfortable to raise.
The prompt
Analyse this transaction from each stakeholder's perspective. For each
party, work out what they actually care about, what they're assuming,
and where their interests collide.
Situation:
[deal structure, key terms, the parties, what's been agreed]
For EACH party:
1. PRIMARY CONCERNS — what do they really care about? What keeps them
up at night about this deal?
2. HOW THEY READ THE TERMS — what do they think they agreed to?
3. WHAT THEY'RE NOT SAYING — which concerns haven't they voiced? What
are they hoping works out without negotiating it?
4. DEAL-BREAKERS VS PREFERENCES — what makes them walk?
Then:
5. MAP THE CONFLICTS — where do interests directly collide?
6. WHAT NEEDS TO BE EXPLICIT — which assumptions should be written into
the documentation before signing?What it surfaces
Run it on a Series A: founder and co-founder, three angels on convertible notes, a lead putting in €3M at €12M pre, a 10% option pool, participating preferred, a 2-2-1 board.
The map pulls the hidden conflicts into the open. The founder reads “participating preferred” as standard and assumes the independent director votes with them — the lead knows the preference bites in a modest exit and plans to influence who that director is. The founder thinks the 10% option pool is settled; the lead knows it needs to grow to 20% pre-money, which dilutes the founder further. The co-founder, who built v1 alone, is quietly resentful at equal vesting and wants acceleration protection nobody has discussed. The angels expect pro-rata rights that were never offered and information rights that are not in the draft.
None of that is in the term sheet. All of it surfaces later as a “wait, I didn’t agree to that” moment. So before signing you schedule three conversations: founder and co-founder on vesting and acceleration; founders and lead on option-pool sizing and the participating-preferred waterfall; everyone and the angels on rights. You do not eliminate the conflicts. You make them explicit, so when issues arise nobody is ambushed.
When to run it
Before you send a term sheet, to catch misalignments before anyone is committed. On any deal with three or more stakeholder groups. And — counterintuitively — when a deal feels too easy: if everyone agrees quickly, usually someone has not understood the same thing as everyone else. If a party has gone quiet, that is the one to map first.
Clean structures only work when the expectations behind them line up. The drafting is the part you are already good at. This is the part that quietly decides whether the deal holds.