Communication PSA: Rescue Hard Conversations with How Questions

Michelle Mains
3 min readMay 21, 2024

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The little kids behind me in the long grocery store line were as cranky as I was. Every time the mom tried to appease or distract them, they answered back in a chorus of, “Why, why, why?” She finally ran out of patience and said, “Anything in that voice is a ‘no’.”

The mom’s comment made me laugh because I’ve been in negotiation rooms with the same sudden shut-down reaction. “Why?” can seem like a necessary question. But have you ever seen too many Why questions backfire? You think you’re being curious or even playful, getting to the heart of the matter. However, with every “Why?”, the other person gets increasingly irritable.

What you don’t catch until it’s too late is understanding the other person’s unarticulated thoughts and emotions. That’s because they thought they explained their Why the first, second, and third time you asked. Pushing doesn’t seem inquisitive — it makes them feel insulted and second-guessed. That’s why they’re beginning to seethe (and now you have an extra problem at hand).

So, the next time someone resists drilling on the rationale or history, here’s your Communication PSA: Rescue hard conversations with How questions. “Why” can be misconstrued as a pointed put-down, kind of like, “Why did you do something like that?!”

By comparison, How questions are natural bridge builders. They are a way to affirm that you are working toward an implementation that works for everyone. That’s a much better reputation boost than someone thinking you’re auditioning for the part of a prosecutor on a Law and Order spin-off!

Let’s examine how switching from Why to How questions will help you create strong partnerships instead of combative, adversarial dynamics.

Empathy as a Communication Cornerstone

Feedback can be a tricky subject, especially for people at the beginning of their careers. However, according to the Washington Post, Gen Z employees are eager for input.

The trouble isn’t the feedback; it’s the delivery. The outcome is bigger than a single bad day or a few hurt feelings. Unhappy workers are backing up those feelings by quitting.

Yatri Patel, a 24-year-old software engineer at the Tennessee Valley Authority summed up the importance of swapping rushed, hard conversations with carefully crafted post-mortems. She remarked, “Rather than just saying, ‘Hey, you did this wrong,’ say, ‘I’d like to have a conversation on where your thought process was and where you went wrong. Help me understand.”

3 Ways How Questions Help Maintain Positive Communications

We’re discussing three communication missteps in the May series, Communication PSAs. The case study shows that rapid-fire Why questions can feel insulting, combative, and perhaps even a demonstration of superiority bias. Those feelings are not only bad for morale — they’re conversation killers.

What people forget to mention is that communication isn’t solely about information. It’s also about creating alliances, so people want to continue exchanging information with you. That’s how you get a steady flow of facts as well as the secret sauce. Because let’s be honest: We all want the inside scoop!

So, save a conversation going south by changing the focus. Questions like, “How will this task be achieved?” keep the group front and center. How questions blend curiosity and empathy, two critical people skills. Cultivating those skills is vital to maintaining a positive discussion.

Are you worried about what you’ll say to a skeptical team member who loves asking Why questions to play the devil’s advocate? You can overcome their objections by pointing out three ways How questions maintain positive communications. Going deeper on How a project is executed:

  1. Respects the work done to date;

2. Saves time by uncovering implementation gaps; and

3. Engages the whole team as everyone suggests ways to improve the project.

The next time you need to understand more, build alliances by knowing when there have been enough Whys and switch to a How. People will walk away feeling confident that you are an insightful, trustworthy person who wants the best outcome, not just your outcome.

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