Vacation Is The Perfect Time to Think About Executive Evaluations (Mad Libs Style)

You are sitting at the ___ (beach, cabin, yoga retreat, hiking trail, family reunion) when hits you:

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 __ (school’s about to start, the board retreat is coming, it’s almost Q4) and you feel ___ (unprepared, uncertain, alarmed, uneasy) because suddenly you remember… the executive evaluation _____ (is coming, wasn’t done, has never been done, hasn’t been done in awhile, what is an executive evaluation?). 

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It snuck up on you because ____ (you are the executive) or because _____ (you are a board member). This one detail which should be routine… isn’t. Or, worse – it is routine, and you hate how it’s done.

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Okay, hate may be harsh. But it’s not far off.

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If this sounds familiar, let’s get you ready so that when you return from the ____ (beach, cabin, yoga retreat, hiking trail, family reunion) you have a real plan.

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The Essential Ingredients of a Good Executive Evaluation

Let’s start by looking at the essential elements that go into a successful evaluation process.

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1. Clarity about who’s involved
2. A relevant, thoughtful evaluation tool
3. A confidential and anonymous way to collect data
4. A supportive process for conversation and reflection
5. A clearly identified work plan (not just a rating)

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Let’s break each of these down.

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1. Who’s Involved – and Why It Matters

Who is involved in the evaluation process often gets glossed over, and it’s where confusion – and damage – starts.

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• Who conducts the evaluation? Executive committee? Full board? A separate committee? If it’s a sub-group, who selects its members – and does the executive have any input? (Answer: yes, at least some.)
• Who provides feedback? Is it the full board? Senior staff? Staff at all levels? Community partners? Clarifying this determines what kind of tool you need.
• Who collects the data? ⚠️ WARNING: Not a staff member. Too often, boards loop in the HR director because they have the skills. But they also have to report to – and work closely with – the person being evaluated. Even the most discreet HR leader can’t unsee what they’ve seen. It changes relationships, even subtly.
• Who delivers the results? Is it a small group? The full board? And what does the full board see? (Hint: At minimum, the executive summary. Ideally, the full report.)

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If you’re thinking, “Wow, this is more _____ (important, involved, coordinated, elevated) than I realized,” you’re not alone. That’s why structure matters – and why so many evaluations fall flat.

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2. A Supportive and Relevant Evaluation Tool

Think of this as a research project: what do you want to know? 

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At CoSpire, we build evaluation tools with questions that explore: 

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• The executive’s leadership style – especially in relationship with board and staff
• Operational effectiveness – how well they run the organization
• Resilience and adaptive leadership – how well they respond to change, challenge, conflict, or uncertainty
• Goal reflection – what was accomplished, what changed, and what was missed (and why) 

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Before you can evaluate performance, you have to define what performance means. And if your tool doesn’t help you do that? We can _____ (help, build it, fix it, upgrade it).

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3. A Confidential, Anonymous Way to Collect Data

This is where most boards – even well-meaning ones – make serious missteps. Confidential doesn’t just mean “please don’t tell.” It means no one can tell. And that requires a few things.

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• Independence – an independent party (like us) to collect and compile the data
• Anonymized surveys – where responses can’t be traced or speculated about
• Careful, contextual analysis - so that one or two critical voices don’t drown out a dozen thoughtful ones.

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We’ve seen executives get handed raw survey comments with no structure or support – and it wrecks trust. It can lead to resignations – not because of the feedback itself, but because of how it was handled.

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The takeaway? Data collection and interpretation should be safe, skilled, and done by people who ______ (are skilled at it, know what they are doing, have the tools for it, have experience in it, have time to do it, all of the above.)

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4. A Supportive Way to Talk About the Results

This part can’t be rushed. When we work with groups of people, we propose a three part process. We recommend:

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1. Private conversation with the executive. A small group (or the person who compiled the data) shares the results, and the executive gets time to process before responding.
2. Private conversation with the board (or evaluating body). The group meets without the executive to reflect on what the data means collectively – not just individually.
3. Facilitated conversation with everyone. Once both sides have had space, bring them together to:

• Highlight insights from the report
• Share reactions and perspectives
• Discuss what’s next

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This model helps everyone show up curious, not defensive. And it reinforces that feedback is ____ (part of growth, essential for self-understanding, a collective experience) – not a pass/fail moment.

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5. A Clearly Articulated Workplan

The result of an executive evaluation should be a shared roadmap for the year ahead. Often, an executive’s evaluation highlights operational and organizational improvements as well. Here’s what goes to the full board:

• The evaluation report (or a thorough executive summary) 
• A workplan with 3-5 goals that reflect strategy, leadership, and alignment.

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The board doesn’t vote on the evaluation, but it is essential that they have the information, especially if the evaluation was conducted by a smaller group. The board votes on the goals. That workplan becomes the foundation for future accountability and support.

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Final Thought

A great executive evaluation isn’t just about judgment – it’s about alignment. It helps the board and the executive come together, reflect, and recalibrate for the year ahead. We often hear executives and board members tell us that they look forward to their evaluation each year. So, yes, it can be done well. Even if you are reading this from a ______ (beach chair, yoga mat, log, lawn chair).