If you ask a yes/no question, you’re likely to get a yes/no answer. But what if the question you’re trying to ask should not have been a binary choice to begin with?

The wrong questions

One of the many ways we try to keep a team of 100% remote workers connected is to have a social or cultural question sent to everyone once a week. The replies are often enlightening and almost always entertaining, as they help each of us to better understand everyone else. If your remote team doesn’t have a process like this, I can highly recommend it for both entertainment and engagement with your team.

Recently though, I have found a number of questions to be very disappointing and I want to highlight three of them along with the reasons why they are so disappointing.

The questions are:

  • Have we made any recent decisions not aligned with what we say we stand for?
  • Do we ever say one thing, but do something else?
  • Is there any part of our team that is intimidating?

As you have likely guessed from the opening of this post, the core problem I have with these questions is how they expect and elicit a yes/no answer.

Recent decisions

The decisions of the past directly influence the choices that we have available now. Yet this first question fails to recognize this.

Have we made any recent decisions not aligned with what we say we stand for?

The yes/no nature of this question is a reduction of the intersections between societal norms, past decisions, current cultural and societal issues, and a company that is actively working to improve. It’s a question that provides opportunity for implicit bias to shine, for real issues to be ignored, and for unchecked problems that past decisions have created to be justified and ignored.

Say one thing, do another

It’s human nature to say one thing and do something else.

Do we ever say one thing, but do something else?

In the world of pschology, it’s well known that people expect others to speak and act in a manner that is consistent with stated beliefs. Yet the same people who expect others to be consistent are usually comfortable with their own decisions being inconsistent. This doesn’t mean it’s willful negligence or intentional harm. But it doesn’t negate the potentially harmful impact, either.


Intimidation is a matter of perspective and perception, informed by a person’s life experiences and the power dynamics at play in any situation.

Is there any part of our team that is intimidating?

There are many reasons to be afraid, anxious, nervous, intimidated, etc. Each and every one of these emotional responses to a situation are 100% valid. Your reaction and how you feel are always valid. This is critically important to understand.

But asking a yes/no question like this only allows us to further ignore very real problems. At best, there is an opportunity missed to discuss the problems. But more likely, denial will lead to gaslighting of those those who see and feel these problems in a company.

First, understand why you’re asking

The term whitewashing is used specifically to call out the societal malady of hiding inequities and injusticies to appease the shame, anger, and violence of white supremacy by rewriting history and current events.

The common thread between all of these questions is that of lost opportunities to improve while whitewashing and ignoring real problems. But there’s a question that goes deeper, looking for the reason a question is asked in a specific way.

Why are you asking?

People who don’t want to address the real problems, or don’t believe the problem exists in the first place, will often resort to yes/no questions with a tone that implies the answer should be “no”. These same people may believe they are asking because they really want to know the answer. But the question itself exposes the implicit bias of the questioner.

The way in which a question is asked is a subtle but meaningful example of intent vs. impact, as the specific wording of a question will directly influence the way someone thinks about the answer. To understand the impact, then, you need to think about the way you are asking the question. And if you want to ask the right question, you need to understand why you are asking the question. Are you looking for confirmation bias about a situation? Or are you truly seeking the real, often painful and difficult answers about the reality of a situation? My hope is that we would all ask the question in the right way to find the real answers.

Now ask the right questions

If we’re looking for the real answers to the questions above, we need to know why we’re asking first.

When I read these questions for the first time, I interpreted them from the perspective of a company that is heavily investing in DEI efforts—a company that has made significant changes already and has put their money where their mouth is. It’s that perspective that makes me want to change what is being asked.

The questions should not be “have we?,” “do we?,” or “is there?,” eliciting a yes/no response. To get the real answers, these questions need to be rephrased in a way that implicitly accepts the reality of Test Double being a flawed company, made of flawed human beings.

  • “Which of our recent decisions are not aligned with our stated values, or DEI goals?”
  • “When are we, as a company, saying one thing and doing something else?”
  • “What parts of our company are intimidating to you? And what steps can we take to remove that intimidation?”

Flipping the questions in this way will help to elicit more interesting and engaging answers by triggering thoughts about specific instances instead of a monolithic yes/no. This opens a world of possible responses, providing greater opportunity for someone to share their thoughts and feelings.

There’s hard work ahead of us

There’s no doubt in my mind that we’ve made progress as a company, and that progress should be celebrated! We should be encouraged, and we should continue to move forward. Real change is happening. But there is no end state we can reach where everything is perfect. That’s not reality.

Living up to our own stated values is a never ending journey and requires constant vigilance. Let’s create opportunities to be vigilant together by asking the right questions.

River Lynn Bailey

Person An icon of a human figure Status
Double Agent
Hash An icon of a hash sign Code Name
Agent 0069
Location An icon of a map marker Location
Waco, TX