Simon Sinek's Start With Why is a classic leadership book (and one of my favorites) for good reason. When inspiring a team to action, communicating the why -- the larger purpose behind the work -- increases commitment and leads to better results and morale. It doesn't hurt that the mandate in the title is memorable and actionable -- even benefiting those who never read past the cover.
However, when thinking about the word itself instead of the sentiment, starting with "why" can actually achieve the exact opposite purpose in a one-on-one setting.
Consider this scenario. Imagine that you made an informed decision to follow a different process for a task than the usual method. However, the new process didn't work as well as you thought, progress slowed considerably, and ultimately the decision to try something new resulted in a missed deadline.
During your next one-on-one, your manager starts the meeting by asking: "Why did you do that?"
How would you react?
I don't know about you, but my heart is beating faster just thinking about it.
Even though the question is logical and likely well-intentioned, the "why?" immediately puts you in a defensive position. What could have been a trust-building conversation where both people work together to diagnose the problem and identify lessons learned, that tiny, seemingly harmless word instead puts the parties on opposite sides of the table, and prompts justification instead of collaboration.
If this happens repeatedly over time, relationships can break down, and people feel less safe or willing to talk openly -- regardless of how they're approached.
To avoid this gloomy future, try to swap out "why" for "what." It's a small change, but it can make a big difference in the tone of a conversation -- and in the long term, the tone of a relationship.
For instance, in the above example, "Why did you do that?" could become, "What led you to try this new process?" While the "why" framing could be easily interpreted as blaming and consequently shut down any further conversation, the "what" version is much more likely to be received in good faith, and prompt an informative and honest back-and-forth exchange.
It might take some additional wordsmithing, but there's usually a way to swap out "why" for "what" in a way that still sounds natural. Here are some additional examples:
"Why are you thinking that way?" can be, "What is it that's causing you to come to that conclusion?"
"Why did you go there first?" can be, "What was it that prompted you to go there first?"
"Why are you angry with him?" can be, "What's behind your anger towards him?"
Questions are a powerful tool for managers to get on the same page with direct reports and collaborate on problem solving, but one of the simplest questions of all -- "why?" -- can thwart that exact purpose. To prevent killing a conversation before it starts, think twice before starting with "why?"