As a technology leader, I often get asked, “Zach, what keeps you up at night?” People ask me this to derive my priorities, but it’s an odd way to do that. It’s an extreme question if taken literally. As an executive, should I lie awake at night, staring at the ceiling, riddled with anxiety and inner conflict? I hope not.

Also, the question is somewhat rhetorical. I think people expect me to answer with a major high-stress project, digital disruption, a production failure, or a data breach. Those are all good answers, but they aren’t my answers. When asked this question, I answer honestly:

“I sleep pretty well, actually. However, occasionally, I do lose sleep due to lack of alignment.” That’s it. That’s my answer.

While data breaches, production failures, digital disruption, and my number one project give me plenty to think about during the day, they don’t keep me up at night. Misalignment can and does, but fortunately, not often.

Control

I am not a control freak. I try hard not to worry about things I cannot control. I pray the serenity prayer often: “God grant me the serenity to accept the things I cannot change, courage to change the things I can, and wisdom to know the difference.”

Even the things I can control, I ask myself if I should control them or not. For instance, I can control everything my team does. I wouldn’t be a very effective leader if I did, but I could.

I choose not to control the decisions of my team members as often as I can. I allow them to make choices and I hold them accountable for the results.

What do I mean by alignment?

This article is about alignment. While self-explanatory to some, I’d like to expound and define the term for context. Alignment means that you and I are going the same direction. We may have differences of opinions on approach and tactics, but ultimately, we agree that we want to wind up in the same place. If we are heading 90 degrees or 180 degrees in different directions, disaster ensues.

There are different kinds of alignment that matter to me.

Strategic alignment

Many of us have been in the unfortunate situation where we are operating under misaligned strategies with our coworkers. It happens all the time. Department X is fighting with Department Y. The amount of wasted energy is horrifying. Imagine if that energy was instead spent on adapting to external conditions, serving customers, and beating the external competition.

Infighting in an organization not only has opportunity cost, it also threatens psychological safety and erodes the culture.

As for me, this absolutely causes me to lose sleep. If am I trying to work in one direction and others in my same company are working against me, I cannot live with that. We need to find a way to resolve that conflict and align our strategies.

The solution is simple but not easy. It’s not difficult to have thousands of employees on org chart. It is an ongoing challenge to have them all working in the same direction. As far as I am concerned, it’s one of the highest art forms of organizational leadership.

The solution is clear strategic priorities that start at the top and get contextualized all the way down to individuals. These need to be communicated clearly and frequently. They also must be compelling and connected to an aspirational vision of the future. Progress needs to be measured and people need to be held accountable.

None of that is easy, but if I want to sleep, I have to do the hard work.

Values alignment

I love diversity of thought, but I do not like diversity of values. I’ve had the unfortunate experience at previous companies where I didn’t see eye to eye with other leaders on important values. For some, the ends justify the means. Not for me. The means matter.

Environments like this are incredibly stressful for me. It’s easy to say, “just stick with your values.” That’s what I did, but the disharmony that comes along with that can be unbearable. That’s more than enough to keep me up at night.

Getting through those periods takes really hard work. You can fight for what is right, try to change the culture, or just leave. There are no easy answers. Right now, I am very happy and satisfied to work alongside leaders with a common set of values. I rest easy.

Those my thoughts on alignment. As you can tell by now, I am an alignment freak. It’s the only way I know how to get a good night’s rest. How about you?

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