Knowing When to ask Why

When interviewing for a new job, there’s one question you need to answer, “Why do you want to leave your current job?” And it’s a good question to ask. Not just for interviews, but for yourself.

I’ve asked that question of myself for several months. It was prompted by company events and even more so after reading Culture Code and Creativity Inc. Asking that question led to my decision to look elsewhere.

I kept asking:

Why is Person B leading this meeting, when Person A is far more qualified?
Why are we making this decision, again? It really didn’t go well for us last time.
Why are we using this piece of technology when we really don’t understand how it works?
Why are we adding this feature which contradicts a previous feature?
Why am I bothered/triggered by this behavior?
Why do I feel I’m being passed over?
Why do I feel marginalized?
Why does this not feel like a safe place to express my opinion?
Why do I care that these issues exist? Are they important enough to do something about?

Point is, I kept questioning our decision making. I questioned why certain actions felt wrong and why I had such a strong reaction to them.

This became the tipping point.

We had a specific project that was a disaster. It was one wrong decision after another. It was poorly designed and executed. Instead of hitting the reset button, we forged ahead missing one deadline after another. The finished product is a total mess. It looks terrible and has dreadful functionality.

Instead of using it as an example of what not to do in the future, dozens of people were promoted. Several “senior” and “lead” positions were dolled out.

People should have been “rewarded” for putting up with trying times, but promotions? We encouraged people for doing less than their best.

Conversely, projects that didn’t go off the rails were ignored. Teams that rolled out new features on time and without drama didn’t get a mention. No one seemed to care when things were working well. All eyes and attention were glued to the shitshow.

So I began to ask questions of myself. I wanted to know if I was missing the big picture.

What information did I need for these decisions to make sense?

What questions do I need to ask to feel at ease with the decision making process?

The more I asked, the more things felt wrong. The more I expressed my concern over decisions, over leadership of teams and projects, the more passed over and marginalized I felt. Being honest was not met kindly.

I kept hearing, “I’m being transparent with you,” only to see a decision put into place that contradicted what we talked about.

When I stepped back, it felt like a game of favorites. There were the “chosen ones” and they could do no wrong. They had become friends with managers and were known for being “Yes men.” But, they were saying yes to bad ideas and bad process. They were saying yes to painting ourselves into a corner.

Lots of unhealthy patterns emerged. We were making the same mistakes over and over again. Problems with a project and within a team could be traced to the same group of people.

That’s when it became clear I needed to stop asking “Why” and start asking “Where?”

Where do I want to go next?

It comes down to this isn’t the work I want to do. These aren’t the people I want to work with. This isn’t the way I want to do my work.

I care about the companies I work for. I’m not interested in just getting a paycheck. I’m not interested in titles. I want to know more tomorrow than I do today. I want to be better at my job than I am today. I want to be faster and more accurate tomorrow.

I firmly believe in “fail fast.” I want to make my mistakes and learn from them. I want to make a dozen small mistakes, understand what went wrong, and do better next time. Failure is an option. And it’s not a problem as long as we learn.

If I succeed at the expense of the team or project, that’s still a failure. If the feature deploys to QA on time, but is riddled with bugs, is that a success?

Case in point, everyone who built the Titanic succeeded at their job.

After a review of all this, I’m better able to answer the question, “Why do you want to leave?”

I want to work for a company that upholds their values.
I want to work with people that learn from their mistakes.
I want to work in an environment where honesty is treated with respect, even when it’s something they don’t want to hear.
I want to be rewarded by my manager saying, “You did a great job. I’m proud of that effort.”
I want to work for a company where managing someone’s career is treated with respect for the privilege it is.