Chapter 6 · Leading Deals
Your First Board Seat
Leading a deal usually means taking a board seat or an observer role. It's the part of the job with legal duties attached, and most investors learn it by doing it. This module covers the difference between an observer and a director, what a director owes the company, the conflict built into being a fund's representative on a board, how good board members actually spend their time, and the moments where it gets hard: down rounds, sales and replacing a CEO.
Observer or director
| Board observer | Director | |
|---|---|---|
| Attends meetings and receives materials | Usually | Yes |
| Votes | No | Yes |
| Fiduciary duties to the company | Generally no | Yes |
| Can be excluded from parts of meetings | Yes, for example to protect legal privilege or where there's a conflict | Rarely |
| Confidentiality obligations | Yes, by contract | Yes |
Observer rights are negotiated in the financing documents. Firms often take an observer seat on smaller positions, or where a director seat would create conflicts. As a principal, your first seat is often an observer role on a deal a partner leads, followed by a director seat on your own.
What a director owes
A director's duties run to the company. In Delaware, where most US venture-backed companies are incorporated, that means the duty of care (make informed decisions) and the duty of loyalty (put the company's interests ahead of your own). Canadian corporate law frames the core duty as acting honestly and in good faith with a view to the best interests of the corporation.
Neither version lets you vote the way your fund would prefer when that isn't what's best for the company.
The dual-fiduciary problem
An investor director owes duties to the company, and also owes duties to their own fund and its LPs. Most of the time those point the same way: everyone wants the company to be worth more. They diverge at specific moments:
- Insider-led financings and down rounds, where your fund is both setting the price and buying.
- Sales of the company, where preferred and common shareholders get very different outcomes from the same price (module 3.1 walks through the preference stack).
- Wind-downs, where the fund would rather stop funding and the company might survive with more.
In the Trados case (Delaware, 2013), a court examined VC-appointed directors who approved a sale in which the preferred holders were paid and common stockholders received nothing. The directors ultimately won, because the common stock would have been worth nothing either way, but only after years of litigation and a finding that their process fell short. The lesson investors took: in conflicted decisions, process matters. Independent directors, a special committee, a fairness analysis, counsel, and a written record of why.
What good board members do
- Prepare. Read the materials before the meeting. Well-run companies send them days in advance; if yours doesn't, ask.
- Ask few, good questions. The board's job is judgment on the big things (strategy, capital, the executive team, risk), not running the business.
- Help between meetings. Most of a board member's value lands in calls and introductions, not in the meeting itself.
- Use the executive session. Time without management, and time alone with the CEO, is where hard things get said early.
- Do the formal work properly. Approving financings, option grants, budgets and the audit. It's routine until it isn't.
The hardest calls
The decisions that define a board member are rare: raising money on bad terms to survive, selling the company, and replacing a founder CEO. Each involves the conflicts above, each needs counsel, and each goes better when the board built trust with the CEO long before it was needed.
Your board load
Every seat takes real time: meetings, preparation and the calls in between. Firms and LPs watch how many boards a partner sits on, because too many means each company gets less. Before you take your first seat, agree with your partners how many you can carry.
What this means for you
Treat your first observer seat as training for the director seat that follows. Watch how the lead director handles the CEO, the other investors and the hard votes. And when your own seat comes, remember whose interests you're legally there to serve: the company's.
Resources
The Venture Capital Board Member's Survival Guide ↗
Names the dual-fiduciary problem of the investor director plainly.
The Board Observer: Considerations and Limitations ↗
What an observer can and can't do, and the legal limits on the role.
The Board Of Directors: Role and Responsibilities ↗
Fred Wilson's plain-English account of what a board is for and what it decides.
The Board Of Directors: Board Meetings ↗
How a good board meeting runs, including the executive session, from a VC who has sat through thousands.
How to Prepare for Board Meetings ↗
A founder's guide to preparing a board meeting. Useful for knowing what a well-run one looks like.