How to ask why at work without upsetting anyone

In open organizations, asking "why" isn't unusual. But you should avoid hurt feelings when you do it.
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I remember an evening, years ago, when I was sitting on the couch watching a movie with some friends. This was in the era of small flip phones, when having a cell phone at all was still a big deal. Many glasses of various beverages littered the coffee table, and my friend Rachel casually tossed her flip phone down as she sat on the couch.

It landed right inside a plastic cup full of beer.

Everyone just stared in silence for a few seconds, trying to absorb the significance of the moment.

"Why did you do that?" I asked, naively, breaking the silence.

"I didn't mean to!" Rachel said, her face turning red. Everyone started laughing as Rachel fished her phone out the beer cup and hopelessly tried to dry it off—the realization that this moment would cost hundreds of dollars started to sink in.

Why at work

At work, we are constantly facing situations with multiple variables, where people are making decisions continuously, and many things are unfolding every day. Often, things don't go according to plan, or something unexpected happens. Many times in a given week, I'm tempted to ask—with the same amount of incredulity I extended to Rachel—"Why did you do that?"

Why did you make that decision? Why is this project a month behind schedule? Why didn't you know about this upcoming event? Why didn't you tell me about that? Why are people sending me complaints about such-and-such?

Today, when I think about about how my friend Rachel must have felt when I asked her why she dropped her cell phone into a cup of beer, I realize I might as well have just asked: "Why are you such an idiot?"

Asking someone "why" they did something, or "why" a certain circumstance exists, is essentially asking them explain their decision making process (or that of a peer) that resulted in a bad outcome. Of course, accidents and other undesirable outcomes happen all the time. While our first reaction might be a desire to get to the bottom of it, it's important to avoid blame or anything that makes the situation worse.

Asking "why" often seems like the most direct way to get at a point, but it can also:

  • Feel like an accusation
  • Trigger a defensive reaction
  • Put someone on the spot and make them feel uncomfortable or embarrassed
  • Imply lack of trust
  • Serve to place blame rather than to find a solution

As with many lessons, I learned this one the hard way. Although asking "why" rarely results in positive outcome, I would often do it reflexively without realizing the ill effects. It wasn't until somebody specifically pointed out to me the dangers of this habit that I finally reflected on my own behavior and realized how often I was doing it.

Alternatives to why

So the obvious question that follows is: "What can I ask instead?"

In their book 50 Top Tools for Coaching, Gillian Jones and Ro Gorell offer several suggestions, starting with asking "What made you do it that way?" or "What made you decide to use that process?" rather than "Why did you do it that way?"

I've used several "Why?" alternatives, including:

  • What is the ideal outcome in this situation? (Follow up: How do you think this situation could have unfolded differently to get to that ideal outcome?)
  • It looks like we're behind schedule. What are the real challenges you're facing with the project? (from The Coaching Habit by Michael Bungay Stanier)
  • How can we set up a communication process to keep us in sync with each other?
  • What were the reasons for that decision?

Before jumping into questions, consider your goals. Did something undesirable happen, and are you looking to extract lessons to prevent it from happening again? Does the team need to solve some ongoing issue? Are you trying to provide coaching to nudge somebody to increase their self awareness and consider their behavior more carefully?

Or are you just curious?

Make sure you understand your own motivations before diving in and asking "Why?"—you may discover that your motives are more about your own curiosity or a reflexive desire to place blame rather than about moving the situation forward. Opening a door you might not need to open can cause more problems than it solves, and focusing your questions on a specific goal will make for a more natural and less confrontational discussion.

Picture of Sam in his home office smiling at the camera. Sam is a white man. He has long curly brown hair and is wearing a dark green zip up fleece hoody.
I lead a team in Red Hat focused on providing context, knowledge, connection and alignment to our Product and Technologies employees, as well as working to ensure they have an inclusive, equitable, and safe environment to work and grow in. I am a late-diagnosed autistic person and I co-chair Red Hat's neurodiversity employee resource group.


I will sure be reading this a few times, and learn from it. As I'm a "why" person myself. I am always curious, and especially in work related situations I want to understand the context for something I work on, so always ask and use why a lot.

Great advice, Sam. I sometimes forget how contentious/confrontational asking "Why?" can be. At least with some people and at certain times. I'll definitely keep coming back to what you wrote in this article!

Thanks, great article!
Another great way to ask could be "what if" and suggesting a few alternatives to extract out the original reasoning behind the chosen way to do things.

Thanks for the fantastic article, definitely something I can relate to! I'm also very used to saying "why the heck did you do that?" with a very genuinely shocked face, and it does seem to give of a very judgemental and accusing impression. Time for me to tame my reaction a little and start to be more empathic :)

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