8 prompts to kick-start an important conversation about your board’s approach to executive performance management.

Executive Director performance management is one of the most important responsibilities a nonprofit board holds. But for many boards, it feels like an awkward chore or a generic annual checklist item. Few board directors stop to ask whether their performance management process is effective, meaningful, or aligned with organizational values. And that’s a big problem.

A thoughtful approach to executive performance management not only helps your board meet its governance obligations, it also clarifies expectations for the ED, supports strategic goals, and strengthens leadership across the organization.

If your board is ready to reflect on what’s working (and what’s not), having some focused, generative conversation is a great place to start. Here are eight key questions to guide your discussion and help your board move toward a more intentional approach to executive performance management.

1. What does success actually look like?

Conversation Prompt: Do we have a shared understanding of what “success” looks like for the ED in their role? Where might our expectations be misaligned or unstated?

Why it matters: Boards often assume everyone’s on the same page, but executive success can mean very different things to different people. Unspoken expectations lead to confusion, mixed messages, and frustration, for both the board and the ED! It’s worth checking in to see if the board is aligned on how success is defined for the ED.

2. Are we equipped to have hard conversations?

Conversation Prompt: Have we ever avoided difficult conversations about performance because we didn’t have the right process or tools? What kinds of supports would help us feel more equipped?

Why it matters: Boards sometimes shy away from giving timely, constructive feedback to the ED, not out of negligence, but because they don’t feel prepared. If you’ve ever delayed or diluted feedback because the process felt clunky or unclear, you’re not alone. Reflect on what could make those conversations easier and more effective.

3. Are we reinventing the wheel each year?

Conversation Prompt: Is our current process consistent from year to year? Does it feel like we’re starting from scratch each time? What would make it easier to implement consistently?

Why it matters: Inconsistency undermines fairness and effectiveness, and it wastes time. A solid executive performance management process should be repeatable and sustainable, not something that gets built from the ground up every time. It’s important to ensure that the board has the tools, training, and timelines needed to keep this process on track.

4. Does this process connect to our purpose?

Conversation Prompt: How well does our current process support our strategic goals? Are we using the process to drive progress on our impact goals?

Why it matters: Executive evaluation shouldn’t be a generic checklist. It should reflect your organization’s core purpose, values, and strategic direction. If your current process feels disconnected from your actual goals, that’s a sign it needs some realignment.

5. Are we building trust, or eroding it?

Conversation Prompt: Does our performance process strengthen trust and collaboration with the ED? Can we think of a recent moment that built trust, or eroded it?

Why it matters: Performance management is a relationship-building opportunity. Done well, it strengthens board-ED alignment and encourages mutual accountability. Done poorly, it can damage morale and deepen divides. Consider how to integrate the goal of trust-building into your process and outcomes.

6. Are our performance conversations a one-way street?

Conversation Prompt: Do we create space for two-way dialogue during performance conversations? Does the ED feel safe and supported in offering feedback to the board?

Why it matters: Performance management shouldn’t be a monologue from board to ED. A healthy process includes space for the ED to reflect, share concerns, and offer their own perspective on how the board is doing in its support and oversight roles. This helps strengthen the organization’s leadership and governance in a broader way.

7. Is our process fair, transparent, and aligned with our values?

Conversation Prompt: Are we confident that our process is fair, transparent, and appropriate for our organization’s size and values? What would improve equity or accessibility?

Why it matters: Many small organizations end up adopting ‘best practices’ that were designed for very different organizational contexts – and the result can be ineffective at best, or harmful at worst. In addition to being ‘right-sized’ for your context, your performance management process should be built on fairness, transparency, and equity, and reflect your organization’s values. Think about where bias might show up, and how to design something that works for your unique context.

8. Does this help us govern better?

Conversation Prompt: Do we feel confident in our current process as a tool for monitoring the ED’s effectiveness? Does it give us the information we need to fulfill our oversight role?

Why it matters: Ultimately, the board is responsible for ensuring that the organization is well-managed, using resources effectively, and advancing its core purpose. If your current approach doesn’t give you the clarity and insight you need, it might be time for a change.

Ready to strengthen your board’s approach to ED performance management?

Use these discussion prompts at your next board meeting or retreat to start important conversations that will strengthen your governance. Use them to reflect on your current practices and identify opportunities to strengthen your organization’s approach to nonprofit executive performance management.

Nic Gagliardi is a nonprofit governance consultant with 18 years of experience helping boards and executive leaders build stronger, more effective organizations. Want to improve your ED evaluation process? Check out the ED Performance Management System designed specifically for small nonprofits.

The views expressed in this article are the author’s alone and do not necessarily represent those of CharityVillage.com or any other individual or entity with whom the authors or website may be affiliated. CharityVillage.com is not liable for any content that may be considered offensive, inappropriate, defamatory, or inaccurate or in breach of third-party rights of privacy, copyright, or trademark.