Why Executive Director Evaluations Go Sideways

By Claudia Sandoval

Most boards either avoid evaluating their Executive Director (ED) or run a process they don't fully believe in.

It's not hard to see why.

You're a volunteer overseeing someone who does this work full-time, knows the organization better than you do, and probably built half of what's working. Giving that person a formal performance review feels — let's just say it — weird.

So boards do what anyone does when something feels weird: they either skip it or they download something from BoardSource and hope the process handles the hard parts.

Here's what often gets missed:

Most EDs actually want this done well.

It's an isolating role. They don't get much direct feedback, and a good evaluation can be one of the few moments where someone says, "Here's what's working, here's what we need, and here's how we'll support you."

That's not a threat. It's a gift.

But instead, six weeks later, the board chair is doing damage control over coffee.

The ED is quietly updating their LinkedIn. And everyone is wondering how something meant to help made things worse.

That's not because evaluations don't work. It's because the board skipped the part that makes them useful.

The Step Most Boards Skip

Before you evaluate, you need to agree on what you're evaluating.

It sounds obvious. It isn’t.

Consider this scenario: The ED thinks the priority is sustainability. The board chair thinks it's growth. Two other board members are worried about culture. None of this has been said out loud.

Then the evaluation arrives and becomes the world's least productive way to find out they weren't aligned.

If you don't have a shared understanding of priorities and success, you're not evaluating performance. You're defining the job.

And your ED is hearing it for the first time in a formal review.

A Simple Check

If your ED asked what they're being evaluated on this year, could you answer in two sentences?

If not, that's your first conversation before any evaluation begins.

Before you start an evaluation, make sure you can answer these:

• Do your board members describe the same priorities for the ED?
• Would you recognize a good year the same way?
• Are you coming to this evaluation with the same goal—or different ones?

If you’re not sure, you’re probably not ready to evaluate yet. That’s the step most boards skip. It’s also why I built the Board Alignment Snapshot.

Four questions. No prep. It shows you whether your board is actually aligned before you launch, so your ED isn’t hearing your priorities for the first time inside a formal process.

👉 Get the Board Alignment Snapshot

If you go through it and think, “we’re not as aligned as I expected,” that’s the work.

Why Executive Director Evaluations Go Sideways—and What to Do Before You Start

Boards often shy away or miss the mark on Executive Director (ED) evaluations.

But in our experience at Charity Search Group, when the foundations for those evaluations are adequately determined before the evaluation begins, EDs find great value in them.

This week, we dive into how to create successful ED evaluations without fear with guest writer Claudia Sandoval, founder of COS & Company.

Drawing from her over 20 years of experience working with nonprofit boards and senior leaders, Claudia shares her perspective in her piece titled "Why Executive Director Evaluations Go Sideways —and What to do Before You Start."

At Charity Search Group, we think about Board and ED relationships intentionally.

As part of our Executive Director search process, we work with boards to define clear 12-month priorities before a role is posted.

We also build onboarding frameworks that map early activities to those priorities—so there is shared clarity not just on what success looks like, but how it will be measured.

NEXT: Continue reading for Claudia's insights on ED evaluations!

Your Next Move Made Clear

Executive Director evaluations rarely fail because of effort.

They break down when expectations were never fully aligned to begin with.

Before your next evaluation—or your next hire—it’s worth stepping back and asking:

• Are we clear on what success looks like in the first 12 months?
• Have we defined measurable priorities, not just broad goals?
• Is there alignment between the board and Executive Director on how progress will be assessed?

When those answers are clear, evaluations become more constructive—and far more effective.

At Charity Search Group, we build this alignment into every Executive Director search. From defining first-year milestones to structuring onboarding plans, our goal is to ensure leaders are set up to succeed from day one—not evaluated against shifting expectations months later.

👉 If your organization is preparing for an Executive Director search—or looking to strengthen how success is defined and measured—connect with us to start the conversation.

Related Resources

• Nonprofit Leadership & Careers — our full guide on this topic.
• Ai Policy Quick Start Templates
• Executive Linkedin Profile Guide
• Learn about our executive search services