How do you evaluate an executive director fairly?

It’s April. Someone on the governance committee notices the executive director’s review was supposed to happen in February. Three board members are asked to “share any thoughts,” two of them reply with a version of “the ED’s doing great,” and the chair writes a warm page-and-a-half based mostly on how the last few meetings felt. The ED reads it, says thank you, and both sides quietly agree not to think about it again for eleven months.

Nobody in that story behaved badly. But that isn’t an evaluation. It’s a compliment delivered late.

Here’s the direct answer to the question: an evaluation is only fair if the goals were set at the beginning of the year, in writing, by the board and the ED together. Everything else — the forms, the process, the conversation — is downstream of that one decision. If the board didn’t say in September what success would look like, then in April it is grading against a standard the ED never saw, which is unfair no matter how kindly it’s written.

So the fix isn’t a better form. It’s an annual cycle.

Start in the first month of the fiscal year

Sit down with the ED early in the year and agree on three to five goals. Not fifteen. The goals should be the things that, if accomplished, would mean the year went well — usually a mix of organizational results (enrollment, revenue, program outcomes) and leadership work (build a development function, stabilize the staff team, get the facilities plan out of study and into a bid).

Write each one so it can be answered yes or no, or with a number. “Improve fundraising” can’t be evaluated. “Grow individual giving from $180,000 to $220,000, and bring the donor count above 200” can. Where a goal genuinely resists measurement — culture, staff morale, community relationships — say out loud how you’ll judge it instead. “We’ll know this went well if the leadership team is intact in June and the exit interviews say what we hope they say” is a legitimate standard, as long as it’s agreed to in advance.

Then both parties sign off on the list, and the board keeps a copy. That document is the evaluation. The rest is procedure.

A note on how the goals get made: it should be a real negotiation. Goals handed down to an ED tend to be unrealistic, because the board doesn’t know where the constraints are. Goals written entirely by the ED tend to be safe. The useful ones come from an hour in a room where the ED says what’s possible and the board says what’s needed.

Check in at the midpoint

Around month six, the chair and the ED go through the list together. Not a review — a check-in. Where are we, what’s off track, what’s changed, does anything need to be renegotiated?

This meeting exists to do one thing: remove every possible surprise from the annual review. If the ED is struggling with a goal, they learn it in month six, when there’s still a year to work with, not in month twelve when it’s a verdict. If the environment shifted — a funder disappeared, a state rule changed, half the staff turned over — the board can adjust the goal formally rather than pretending the original list still applies.

Boards skip this step more than any other, and it’s the one that does the most work.

Gather the input

Six to eight weeks before the review conversation, run the collection.

The ED writes a self-assessment first. Give the ED the goal list and ask for a written response: what got done, what didn’t, what they learned, what they need from the board, and what they’d set as next year’s priorities. Ask for it before board input goes out. A good self-assessment reframes the whole exercise — it’s remarkable how often an ED grades themselves harder than the board would, and how often it surfaces obstacles the board didn’t know existed.

Every board member responds, with structure. Send the same short form to the full board, organized around the agreed goals plus a few standing questions — communication with the board, financial stewardship, staff leadership, external representation. Ask for comments, not just ratings; a row of 4s teaches nobody anything. Set a deadline and hold it.

Two cautions here. First, board members should answer only about what they’ve actually observed. A trustee who attends meetings and reads reports can speak to board communication and organizational results, not to whether the ED is a good supervisor. Give people permission to write “no basis to judge.” Second, the form is about the organization’s results and the leadership behind them — not about likability. It’s worth saying that explicitly in the instructions, because unstructured evaluation drifts toward personality with almost gravitational reliability.

Staff input: be careful. Some boards gather it; many deliberately don’t. The case for it is obvious — the staff sees the ED’s actual management. The case against is real: staff members depend on the ED for their livelihood, and an evaluation channel that runs around their supervisor to their supervisor’s boss can do lasting damage to the organization’s lines of authority. If you do it, do it deliberately: a professional, anonymized survey with enough respondents that no one can be identified, run on a predictable annual schedule rather than in response to a rumor, with results summarized in aggregate and never handed over as raw quotes. If your staff is small enough that anonymity is impossible, don’t pretend otherwise. And know that once you start, stopping sends its own message.

Synthesize, then talk

Raw feedback should never go to the ED as a stack. Someone has to read all of it and write one coherent document — the chair, or a small committee of two or three (the chair plus the incoming chair plus one other is a good combination, since it builds continuity).

The written summary covers each goal with the board’s honest assessment, names two or three strengths with examples, names one to three areas for growth with examples, and closes with what the board commits to doing differently. That last section matters more than boards expect. A great many ED frustrations are actually board frustrations — decisions that never get made, committees that don’t function, a chair who doesn’t return calls.

Then the conversation. The chair and one other person, an hour, scheduled, private. Give the ED the written summary in advance so they aren’t reacting live. Spend the first half on the year, and the second half on next year’s goals — because the best evaluation meeting ends by setting the next cycle’s list. The meeting closes the year and opens the new one in the same sitting, which is how the process becomes a habit instead of an annual ordeal.

Keep compensation in a separate conversation

Run the performance discussion first, on its own. Have the compensation discussion later — a different meeting, and typically a different group (an executive or compensation committee, with the board approving).

There are two reasons. The practical one: when money is on the table, nobody hears the feedback. Every sentence gets read as a signal about the number, and the developmental conversation you wanted evaporates. The governance one: compensation should be set against market data for comparable organizations, the board’s budget reality, and its own policy — not purely as a scorecard on the year. Both conversations are legitimate. They just work badly at the same table.

The unglamorous parts

Keep the evaluation on the annual calendar with a date and an owner, the way you’d treat an audit. “No news is good news” is not a management philosophy; it’s how a board arrives at a crisis having sent no warning, and how an ED gets blindsided by dissatisfaction that had been accumulating in the parking lot for two years.

And keep records deliberately. Written evaluations are personnel documents. How they’re stored, who can see them, how long they’re kept, and how they interact with your state’s employment law and any open-records obligations are all worth a conversation with your attorney once — then write down what you decided and follow it.

The one-sentence version

Set written goals together at the start of the year, check in at the midpoint so nothing is a surprise, collect structured input from the ED and every board member, have one person write one honest summary, talk about it in a real conversation that ends with next year’s goals — and talk about money on a different day.