A Better Way to Evaluate Executive Directors: Simple Monthly Check-ins That Actually Work

Stop wasting time with clunky evaluation processes. Here's how to create meaningful monthly check-ins with your executive directors that drive real results.

Arjun Rajkumar

Using the Monthly executive director evaluation form template

Setup automated daily check-ins with your own custom monthly questions. Your team receives the questions every month, and shares their updates with you.

This saves you time from having to create these questions manually every month. By automating it and getting everything written down at the beginning of every month, it increases accountability and keeps the whole team on the same page.

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Hey there — I'm going to tell you something that might sound controversial: Most executive director evaluations are broken. They're either too infrequent (yearly reviews, anyone?), too cumbersome, or worse — they don't happen at all. We've seen countless organizations struggle with this, which is exactly why we built Progress Updates.

The truth is, keeping tabs on executive leadership shouldn't feel like pulling teeth. It shouldn't require scheduling endless meetings or dealing with complicated forms. What if you could get meaningful updates from your directors every month, right in your inbox, without the overhead? That's exactly what we're going to show you how to do.

Why is a monthly executive director evaluation form template important?: Monthly evaluations create a rhythm of accountability without micromanagement. They're frequent enough to catch issues early, but not so frequent that they become burdensome. The key is making them lightweight and asynchronous. When executive directors can respond on their own time, you get more thoughtful, detailed responses. Plus, having everything in writing creates a clear record of progress and challenges — no more relying on memory or hastily scribbled notes from in-person meetings.
What makes a good executive director evaluation form template?: The best evaluation forms aren't about lengthy questionnaires or arbitrary rating scales. They're about asking the right questions that prompt meaningful reflection and honest communication. Think of it as opening a dialogue, not conducting an interrogation. The form should be easy to complete (no fancy software required), encourage detailed written responses (because numbers alone don't tell the whole story), and maintain a consistent structure from month to month so you can track progress over time.
How do I create a executive director evaluation form template?: Creating an effective evaluation form doesn't have to be complicated. Start with a simple online template that you can customize with your own questions. With Progress Updates, you can schedule these questions to go out automatically each month. Your directors can respond directly via email — no logins, no apps to install, no friction. Plus, you can add follow-up questions to dig deeper into specific areas without making the process overwhelming.
What's the best format for executive director evaluation questionnaire assessments?: Skip the PDF forms and Word documents that end up buried in email threads. The best format is the one that actually gets used — and that means going digital and asynchronous. Using a tool like Progress Updates, you can create a consistent monthly check-in that's easy to complete, easy to track, and easy to reference later. The responses are automatically organized and archived, creating a valuable record of progress and challenges over time.

Sample monthly questions:

You can add any monthly questions you want, and schedule the questions to go out to your team repeatedly at any time in the monthly via Progress Updates. Here are a few sample monthly questions related to Monthly executive director evaluation form template:

What key milestones or objectives did you achieve this month, and how do they align with our organizational goals?

This question helps track concrete progress while ensuring alignment with broader organizational strategy. It encourages directors to think beyond day-to-day tasks.

What's the most significant challenge you're currently facing, and what resources would help you address it?

Regular check-ins on challenges help identify and address issues before they become critical. It also opens the door for meaningful support conversations.

How are you developing and supporting your team this month? Any notable wins or concerns?

This focuses on leadership effectiveness and team health, crucial aspects that often get overlooked in traditional evaluations.

What's one decision you made this month that you're particularly proud of, and why?

This provides insight into decision-making processes and helps track leadership growth over time.

Looking ahead to next month, what are your top 3 priorities and how can the board better support you?

Forward-looking questions help maintain strategic focus and ensure proper support structures are in place.

The best evaluation process is the one that actually happens. By keeping it simple, consistent, and asynchronous, you create a sustainable rhythm of communication that helps both directors and organizations thrive. No more dreading annual reviews or struggling to remember what happened six months ago. Just clear, regular communication that keeps everyone aligned and moving forward.