Chris Costello

Chris Costello is an Instructional Designer based in Minneapolis. As a former teacher and graduate of the University of Minnesota’s M.Ed. program, he uses the best research-based methods to make professional learning effective, engaging and easy. He designs customer-facing and internal training that replaces outdated we’ve-always-done-it-this-way malarkey with methods that are proven to be effective. He is a two-time Pinewood Derby state champion. Find out more about Chris’ work at

Published Thoughts

Why I’m Skipping Why

One of the most significant differences between a successful project and one that merely ends is an understanding of the project’s why; what need is it serving, and does it actually serve that need. I’ve learned that when you want to understand the why of a project, “why” is the last question you want to ask.

“Why” feels like the place to start. After all, that’s the information we ultimately want to discover. The direct approach may not be the best tactic though, because why is elusive. If you come straight at why you’re likely to miss the mark. Other questions can help you find why, narrowing the borders around it and flushing it out like trained hounds. While “why” is a tempting question, it shouldn’t drive project kickoff meetings or needs assessments.

Why is accusatory

Why asks for a justification, and justifications make us feel like something went wrong. You can’t get good information out of someone who is on the defensive. Furthermore, asking someone whose job revolves around the who, when, where and what to talk about why is asking them to step a little bit outside of their comfort zone already. Our brains work differently when we’re stressed, so in addition to possibly provoking someone to bend the truth a little to defend themselves, you’re also creating a situation that might limit a person’s recall or clear thinking. Start with information that you think will be easy for them to answer. The more at ease your interlocutor is, the more willing and able they are to answer your questions.

Better questions: What does this do? What did you do on this project?

Why is subjective

Even if people do know “why,” everyone has a different why. A person’s why is based on their circumstances and point of view. If you ask two different people why a site is laid out a certain way or why the timeline is the way it is, you may get two different answers. Why opens you up to someone’s personal narrative of what’s going on, and this is often made up of supposition about things they have no firsthand knowledge of and possibly personal attacks or political fibbing.

It’s best to start with questions that have factual answers. Starting with “when” can help you to establish a timeline. Understanding what else was happening at the time can be a big step towards finding why. Gather all the facts that you can and follow where they lead you. This requires more time and brain power than just asking why, but you’ll know you can rely on the information as a foundation.

Better questions: What would happen if we did/didn’t do this? When did you start this?

Why is incomplete

People at the top don’t know the details, and people on the ground floor don’t know the whole story. This means that both sides often have to follow directions that they don’t know the whole background for. This is why you want to gather facts from both ends so you can piece together the real story. You might end up being the one person in the organization who really understands the why.

Once you have the facts, it might be time to move on to why. You’ll be able to spot omissions or misunderstandings and address them right there. If the problem is based on poor communication, you may be able to find a solution, just by getting the accurate information to the right people.

Better questions: Who requested this feature? What reason did they give you?

The approach you take in interviewing people can have a serious impact on the quality of the information you receive. It is absolutely worth your time to prepare your questions ahead of time and to use a little why on yourself. “Why am I asking this question?” Your answer should be a. To put the person at ease, b. to capture all perspectives on the issue, or c. to get all the facts.