Let’s Talk About the Questions That Matter Most

When organizations think about evaluation, the first thing they often think about is data collection. But before you build a survey, schedule interviews, or create a dashboard, there’s a foundational step that deserves your attention:

Deciding what questions your evaluation is meant to answer.

These aren’t your survey questions — they’re the deeper, guiding questions that shape the direction and purpose of your entire evaluation. These are your evaluation questions, and they are the backbone of a strong, intentional learning strategy.

A Grocery List (and Evaluation Questions)

If you’ve worked with me, you’ve probably heard my grocery shopping metaphor — but it’s worth repeating.

When you sit down to make your grocery list for the week, you rarely begin with “fish tacos” or “salsa.” You start with the big questions:
​What do we want for breakfast this week? Lunch? Dinner? What snacks do we need?

Those broad categories shape what ends up on your list.

Then come the specifics:
​Fish or bean tacos? What kind of salsa goes best?

That’s how evaluation works, too. Your evaluation questions are the big questions (e.g., “How are our programs supporting long-term stability for youth?”), while your subquestions are the more detailed prompts (e.g., “How do youth describe the impact of our financial literacy workshops?”).

Start big. Stay intentional. Then get into the details.

How to Develop Strong Evaluation Questions (Collaboratively)

Here’s a process I often lead teams through — and one you can facilitate yourself:

Step 1: Set the Table

Decide whether this will be a solo reflection or a team conversation. If it’s a group, bring together people who hold different perspectives — program staff, leadership, fundraisers, even community partners if you’re ready.

Set aside 45–90 minutes, depending on your group size and how much discussion you’d like.

Step 2: Surface the Questions

Start by giving each participant space to answer this prompt:

“What do you want to know about our work? What do you need to know?”

You can phrase this slightly differently depending on the audience — for example, “What do our funders always ask?” or “What do our participants wish we better understood?”

Have people jot their ideas down as individual sticky notes (or in a shared Google Doc or Jamboard). One question per note. Encourage them not to overthink or translate into “evaluation speak.” The goal is breadth, not polish.

Step 3: Group and Cluster

Put all the sticky notes up on a wall (physical or virtual). Then, as a group, begin reading them aloud and grouping similar questions together.

You might end up with clusters like:

• “How effective are our services?”
• “What’s the long-term outcome?”
• “Are we reaching the right people?”
• “What’s working well in our approach?”

You’ll likely also have outliers — questions that don’t fit a clear group. Don’t discard them. Set them aside. We’ll come back to them.

Step 4: Name the Clusters

Next, step back and ask: What is this group of questions trying to understand?

Write one overarching question that represents each cluster. This becomes a draft evaluation question — one that captures the essence of several smaller questions.

These are the “what’s for dinner?” questions — not the salsa brand.

Step 5: Connect to a Framework

Now, take a look at your draft questions and ask: What kind of question is this?

Most evaluation questions fall into one (or more) of these six categories:

• Process – How is the program being implemented?
• Outcome – What changes are occurring as a result of the program?
• Effectiveness – Is the program achieving its intended goals?
• Appropriateness – Is the program a good fit for the population and context?
• Cost-Benefit – Is the value of the outcomes worth the investment?
• Efficiency – Are resources being used wisely to achieve results?

You might have overlap — and that’s okay. Some strong evaluation questions blend types. For example:
​Under what conditions does our program most effectively support school readiness?
​This blends process, effectiveness, and even a little appropriateness.

Step 6: Prioritize What Matters Most

You probably have more questions than you can realistically answer. That’s expected.

Now it’s time to prioritize. Ask yourselves:

• Which questions are essential to answer this year?
• Which questions help us make decisions or adjust strategy?
• Which questions are required by funders?
• Which questions feel urgent or timely based on recent shifts?

Narrow it down to 2–4 core evaluation questions. These are your compass. Every tool you build — a survey, an interview guide, a dashboard — should help answer one or more of these.

The smaller, detailed questions? They become your subquestions — guideposts for how you design your tools and interpret your findings.

A Moment of Reflection

Think about the last time you launched a survey or wrote a report.

Did you know what you were trying to learn from the start?

Or were you hoping the data would speak for itself?

When we aren’t grounded in clear evaluation questions, we risk collecting a lot and learning very little.

But when we pause to ask the right questions — and ask them together — we move closer to meaningful, useful, human-centered evaluation.

Want help leading this process?
​Helping teams ask the right questions is one of my favorite parts of evaluation coaching. Whether you're just getting started or trying to recalibrate a scattered system, I can help you find clarity and alignment. Reach out here and let’s talk.

With curiosity and care,
​Kayla

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Exciting news at Bridgepoint: We gained a team member!

Meet Chayney Beard – Operations & Admin Sidekick

Chayney is a virtual assistant with a passion for bringing order to chaos and turning clunky processes into smooth-running systems. With over a decade of experience in small business environments, Chayney understands firsthand the value of time, clarity, and well-oiled workflows. Her specialties include process optimization, automation, project management, and bookkeeping—services she approaches with precision and care. Chayney is to Bridgepoint what Bridgepoint is for nonprofits - she turns chaos into clarity, creates approachable and advanced solutions, and does so collaboratively.

But beyond the spreadsheets and systems, Chayney brings heart to everything she does. Guided by values like loyalty, patience, and fairness, she works with genuine kindness and a strong sense of dedication. She believes in the power of thoughtful support and quiet strength to transform how teams function and flourish. When she’s not optimizing workflows, you’ll find her gaming, geeking out over planners and stickers, or preserving memories through her love of journaling and scrapbooking.

In short: Chayney is the behind-the-scenes powerhouse who helps teams breathe easier and operate better—one task at a time.