Asking the Hard Questions

By Cat Miller February 4, 2019


There are weak spots in every company that no one likes to talk about. The network engineer who is the only one who can make changes to the firewall. The one person who has a great relationship with the difficult client and can talk them off the ledge every time. The system held together with duct tape that can never be recovered if it ever goes down...

Six months ago one of my teams went through a crisis. Despite being a generally happy, well-functioning and extremely productive team, I found myself with three people on it who independently needed a change at the same time. One person left the company for another opportunity. Another told me they wanted to transfer to a different team to have an opportunity to work on different projects. A third just told me that they were miserable. That meant that seventy-five percent of this team's engineering staff needed a change, in a part of the organization where we have high external deliverable risk and visibility. It was a full-on panic situation that we only got through by a complex game of Tetris involving a lot of different people who went above and beyond to get us through.

What happened? Why did everyone suddenly need a change at the same moment? Why didn't I see it coming, why wasn't I more prepared for it? Was I really that out of touch and unaware of what was going on with my team?

The answer was simple: I wasn't looking for the things I didn't want to see.

At the crux of the issue were my 1:1s with each direct report. Here's how things went wrong: I would sit down with a direct report, and they would tell me things that were top of mind. It would be a mix of current concerns and bigger picture ideas and planning. We might talk about how at some point they'd like to be working on thing [X], probably on team [Y]. Or how things were rough right now, but once [Z] happened, they would get better. I would listen, ask some follow-up questions, strategize about possible solutions.

Sounds kind of reasonable right? Not a total failure of Management 101. But I never asked the harder follow-up questions: How long are you willing to keep working on thing [X]? What if team [Y] doesn't have any openings? What if [Z] doesn't happen soon?

With one person, I had in my mind that a directional transition to focus on platform goals we had been talking about would happen within six months. That person had two months in their head.

With another, I knew that their role had grown to become something they didn't enjoy, but didn't probe on whether they would prefer something entirely different over incrementally fixing it. As a result, I was only looking to change the circumstances rather than find a replacement.

With a third direct report, I knew that they wanted to try working on a different stack. But although I agreed that was the right direction for their career and offered to help figure out options, we never made a concrete plan for what those next steps would be.

What I learned in that short period of time is how easy it is to fool yourself and everyone around you into believing you are a good listener, when you actually have selective hearing. There were weak spots that I feared pushing on, because I didn't know what I would do if they broke. It was scary and icky to contemplate this thing that my org wasn't ready to handle, and so I didn't dig to find it out. Had any of these people gave me an ultimatum, I didn't have a solution, so I didn't want to give them the opportunity.

We got through those months, unfortunately by putting added strain on team members other than myself. Lots of folks stepped up, which was wonderful to see, a true testament to our engineering culture. But we also took a revenue hit in contracts that we couldn't take on, which was not wonderful.

What I took away from the experience is to always ask the question you are most afraid to hear the answer to. "Is this something you can keep doing for another month?" "Do you think that it's unfair you didn't get a promotion?" "What would happen if this critical system failed tomorrow?"

For some indirect reports that I may not know as well, the questions might be pretty vague: "What's the thing that is frustrating you the most right now?" "What do you wish you could change about the team?" With some direct reports it's extremely specific: "Three months ago we talked about you moving towards plan [X]. We haven't made as much progress as we had hoped. What do you want to do now?"

Emotionally, I've had to get myself to a place where I can be more relieved to know the answer than I am scared to ask the question. Others who are less avoidant than I may not have this problem, but I've had to convince myself that it is unacceptable to leave a 1:1 without asking the scariest question I can think of. There is a reward on the other end in the comfort that comes with knowing where things stand.

There are weak spots in every company that no one likes to talk about. It's easy to slide back into assuming that everyone is ok unless they tell you otherwise. For now, the memory of disaster is incentive enough for me to continue ask the hard questions. Once that fades, hopefully I can re-read this and remember anew why I need to hold myself accountable for asking the scary thing.