Make a plan and do your best

When I became an Engineering Manager, my to-do list ballooned with people to meet with, decisions to make, projects to track, questions to ask, and dozens of other tasks. And everything seemed hair-on-fire urgent! I was constantly shifting my attention from one task to the next, and I felt like one of those sharks that has to keep swimming just to keep breathing. I didn't have time for reflection or growth. I didn't even feel like I was succeeding – I was just trying not to sink.

John Cutler tweeted this image that triggered the same feeling for me:

A diagram of the complexity of running a business, by John Cutler (https://twitter.com/johncutlefish/status/1487161957916430337)

John's diagram is about the complexity of running a startup, but this kind of intractable graph of competing "#1 priorities" extends to leading a team, too. Is the roadmap up-to-date? Is the team executing on it? Are we blocking other teams? Are we measuring impact? Are people motivated? Are we hiring well? Onboarding new hires well? Managing performance well? At any given moment, a new priority will rise to the top of the list or get shoved onto the list by someone else, and they can all seem equally important. You can circle around forever in this sea, tossed about by currents, swimming and swimming...

These days, I feel less like a shark and more like a ship. I feel like I can set my own destinations and chart my own course, but I've got sails so I'm still a bit at the mercy of the winds and tides. But at least I'm navigating.

Part of what's changed for me has been my environment. I work with exceptional engineers and I'm supported by a set of strong peer leaders who own product management, technical leadership, and design leadership. These individuals combine in a way that makes challenges tractable in every respect. Everything really is awesome when you're part of a great team.

But what's changed for me on a personal level is my mindset and how it has affected my approach to work. I'm able to focus on the areas where I can make a critical difference and as a result I experience less stress and more satisfaction in my impact and growth. If you're feeling overwhelmed at work maybe you'll find some inspiration in how I've learned to cope.

Mindset

When you've got a to-do list that's constantly growing, you can be sure of two things:

Most of the tasks on the list won't get done.
It will take so long to sort the tasks by priority, that by the time you're done the list will have a dozen more tasks on it and you'll have to start all over again.

One time when my daughter was 3-years-old I heard her say: "Make a plan, do your best." I'm pretty sure she was parroting something she heard on TV. But the simplicity of it resonated with me! Making a plan and doing my best is basically all I can do. The rest is up to fate.

I will fail

Step 1 of Alcoholics Anonymous is to "admit powerlessness." In that program, recovering alcoholics are told that they won't be able to cope with their addiction until they learn to accept it. I had a similar breakthrough when I learned to accept that I am going to fail.

I can work around the clock, sacrifice time with my family, optimize every minute of the day, but no matter what I do I am always going to let someone down, or miss some deadline, or learn about some decision too late to influence it. Juggle enough balls and some of them will get dropped. All I can do is decide which ones end up on the floor.

But what's the process for deciding what gets done and what doesn't?

"Good enough" is good enough

Satisficing is the tactic of conserving costs during decision-making by selecting a "good enough" solution instead of "the best" solution. After all, I could spend all day just prioritizing tasks. By the time I've identified the absolutely most important things to work on, I won't have any time left in which to do them! And sometimes situations will be so fluid that the most important things will change in another month anyway.

Better to act quickly on something (anything!) important to maximize the odds that it will get done.

Approach

Selecting work

I select an "important enough" thing to work on using these criteria:

Is this a high-impact long-term investment? I think of these types of activities as building bridges before I need them and I've found that they're the only way I can transition out of fire-fighting, er, shark-swimming mode. Examples:

Instead of writing performance reviews for each of my team members I'll coach them on writing their own self-assessments, which we'll then review together.
Instead of coaching each individual on how to improve their interviewing ability, I'll design an interviewing system using written guidelines and shadowing so that team members can help each other.

Am I the only one who can do it? This criterion forces me to do the unrewarding work that I really don't want to do, like working through third-party contracting agreements with Legal and Finance. It's tedious, but essential.

There are two cases where I'll try to delegate the work:

If it can be done by someone who's not on my team but is in a better position to be effective or has a more vested interest in seeing the work through.
Even better if someone on my team can do the work, because then it becomes a sponsorship opportunity.

Will this work unblock others? Paraphrasing former Intel CEO Andy Grove, the formula for measuring a manager's impact is impact on their team plus the impact on peer teams. Therefore work that will unblock my team or unblock adjacent teams is high impact and I should prioritize the work.

Tracking work

An XKCD comic of a person saying, "I started the day with lots of problems. But now, after hours and hours of work, I have lots of problems in a spreadsheet."

I track my work in a Google Doc broken into three sections:

Today. Two or three things I want to accomplish that day. I like these things to be concrete and narrowly-defined, otherwise I tend to procrastinate. For example instead of "Create interviewing guidelines," I might have "Define criteria for progressing a candidate from the initial recruiter screen."
Tomorrow. Same as above, but for the next day. By sticking to two or three things per day I limit work-in-progress. This is a common concept in Agile, Kanban, Lean methodology, and other popular business philosophies that emphasize efficiency. I've found it helps me focus and maintain steady progress.
Someday. This is a backlog of things that seem important, typically 10-15 tasks long. Tasks tend to be more vaguely defined. I groom this list whenever I finish a project or when it grows too long, removing anything that's obsolete and converting high-priority items into tasks in the Today and Tomorrow lists.