As evaluators, it’s our job to ask questions. When I tell people about what my company does, I tell them we help organizations that do good, to do better, by asking the right questions and answering them. Through asking and answering questions, we frame our evaluation projects, unearth data, and share helpful insights and recommendations.

Many of us arrive in evaluation because of our penchant for asking questions. And even though we’ve all been told “there are no dumb questions,” sometimes it feels like we really should know the answer already. It can be intimidating to speak up and admit your lack of knowledge or understanding.

But evaluators need to get comfortable asking questions, silly or not. Ever heard the term “playing the fool?” The idea behind that phrase is that if someone behaves in a silly way, or repeatedly asks silly questions, they’ll be seen as, well, silly. They won’t be taken seriously. What evaluator, whether an internal employee or contracted consultant, wants to look silly? Well, there are some important reasons to consider asking some silly questions at your next evaluation meeting.

Michael Quinn Patton has likened the role of the evaluator to that of the court jester, also called a fool. The jester’s role in English courts was to entertain, and they had the special privilege of being immune from punishment for what they said. Their unique role enabled them to question, to bear bad news, or to present new or unwelcome perspectives without fear of reprisal. Personally, I’ve latched on to this metaphor and love the idea that evaluators can occupy a special position, speaking truth to power without (too much) worry for their position.

Here are a few situations where thinking of yourself as a court jester, playing the fool, can help you to be a great evaluator.

1. When understanding how an initiative operates

As an outsider, you probably don’t have all the details of the initiative you’re evaluating. Even if you are an internal evaluator, there may be some aspects of a program that you’re not familiar with, or don’t make sense. By positioning yourself as a person in need of educating, you create an environment in which those important details can be shared. In a project kick-off meeting, I like to say very directly that I will probably ask some silly questions and ask the team to help me learn.

2. When certain questions aren’t being asked, but should be

In setting the context where I’m seen very clearly as a non-expert, I can also query the “why” behind puzzling aspects that other team members can’t safely ask about – but may very well also be questioning. After all, I, this silly outsider, shouldn’t understand why a process was set up in the way it was, or how a decision was made. But an internal team member who may also be wondering the same thing doesn’t necessarily have the same psychological safety to ask that very question. By playing the fool here, I can ask about that “elephant in the room” that nobody seems to be addressing.

3. When the group needs to know it’s safe to query

Not every workplace operates with psychological safety. In some settings, the organizational culture is such that people are afraid to fail, or they have a very realistic concern that their job would be at risk if they asked too many questions. An evaluation project requires trust and honesty; when those qualities are absent from an evaluation, the project risks being able to fulfill its purpose. As an evaluator, you can be very intentional about modelling question-asking and encourage the team you’re working with to also speak up when something doesn’t make sense.

4. When important but unwelcome insights need to be shared

We always hope that evaluation projects are driven by a true desire to learn and improve. That’s not always the case, though. As much as we prepare clients for the possibility of both positive and negative outcomes, and potentially scary recommendations, they’re not always ready to hear those findings. I note that with great empathy – as a business owner myself, I wouldn’t be super excited to hear that things aren’t going well and major adjustments are needed, either. It’s tough to hear that you may have been misdirecting your efforts. But in the best interests of all, those insights do need to be addressed. You can lead with your inner fool by being curious, vulnerable, and creating that safe space for receiving unwelcome news. A bit of well-placed humour can help to reduce defensiveness and bring a bit of joy to an otherwise dismal event.

Now don’t take this imagery too far! You don’t need to intentionally appear less intelligent than you are, and you don’t need to wear a goofy hat with bells on it. I’m not suggesting that you ask outright stupid questions (not that you would anyway). Nobody said that the court jester was dumb – far from it, that royal fool was full of crafty insights and clever language (just like you!). You know that your “silly questions” are actually a very intentional way to get people talking about the important things. As a skilled court jester, you’re carefully navigating humility and professionalism to create a safe environment for constructive conversation. And your evaluation project will be better for it.