Don’t be spooky

It’s possibly the best advice for managers I’ve given so far. When you’re communicating with your team, lead with context and reassurance. Never message someone on your team, “let’s talk when you get a minute”. That’s void of information and scary as heck!

I have to remind myself of this when I’m rushing. It’s faster to ping someone to arrange a synchronous talk than it is to write out what I need to say and cover all the bases. But that doesn’t give me license to skip all the context. Broad strokes are okay. An information vacuum is not okay.

Accidental spookiness invites story-crafting. Minds race. Lacking information or context, we tell stories. They often aren’t happy stories, regardless of how good your relationship with the team. We humans are better at convincing ourselves to fear something (survival instinct) than the other way around.

Avoiding spookiness reduces the chance of people telling themselves negative stories. Context and clarity counteract reading the tea leaves and world building. Even more important, it prevents people from pre-gaming the conversation. That way, they don’t prepare for a conversation that happened in their heads, instead of one that’s about to happen. (Avoiding pre-gaming is important on both sides of the conversation, as it turns out.)

A corollary to “don’t be spooky” — deliver constructive but critical feedback as close to the “original sin” as possible. Receiving feedback that you did poorly weeks after the fact is disconcerting. It can lead the recipient to wondering what other things they’re doing poorly but won’t hear about until later. Which leads to story-crafting, and the whole negative cycle starts a-new.

Give your team enough context to pre-game conversation based on the real context, not conjecture. And don’t hold on to feedback for “that perfect time”.

“Rationalize and solve” doesn’t help someone who is venting

If you’re doing the whole servant leadership thing, you’re gonna hear some people venting frustrations. Yihwan Kim, When a 1:1 turns into a vent session:

As an engineering manager, I’m learning that a big part of my job (perhaps my only job) is to help people solve problems. I happen to enjoy solving problems myself. So it’s only natural that when someone starts venting, I want to rationalize the conversation, correct inaccuracies, and discuss actionable next steps.

I always have to remind myself: don’t.

Relatable. It’s easy to react to someone venting by rationalizing and solving. As Yihwan points out, that’s not the card to play here. The win condition for these is to 1) hear your colleague out and 2) help improve the cause of the vent if your teammate wants you to.

One priority is like wind in the sails

It’s true that I can scale myself, teams, and organizations to walk and chew gum at the same time, but it is surprisingly effective to focus on one thing at a time. This is the essence of “priority” — put all my energy into one outcome until it’s done. Then the next one, the next one, etc. as my efforts start to compound.

I, like many folk, do much of my best work in coffee mode. When that deep, coffee mode work aligns with my priority, everything is operating smoothly and life is good. If my priority (singular) changes and I need to go deep on something else, that’s not ideal but not so bad either. As long as I can still focus, things are good. When I’m asked to go deep on two things or pulled to work on deep but unaligned tasks, that’s when things get gnarly.

A useful activity that looks like (and is often called) prioritizing is sorting (“triaging”) a list of potential work by what’s most impactful or important. This is more of a planning activity than a priority exercise. It acknowledges there’s a lot to do and time is finite. The result sends a clear signal: this thing at the top of the list is more important than all the things below it. In particular, any of the top items are more useful to work on than all the things further down the list.

Get better at finishing projects. That’s working smarter, not harder. Finished projects, axiomatically, don’t need prioritizing against other work. Limiting work in progress is difficult to pull off in the moment but a crucial tactic to apply when things get intense.

Possibly controversial: multiple priorities is about the same as having no priorities. The trick that priorities pull is freeing us of the energy-sapping process of deciding what’s most important and what trade-offs to make. A single priority is a note from your past, well-considered self saying “this is more important than all the other things; work on it before anything else”.

Systems of “one priority”:

Multiple priorities make it unclear what expectations are for individuals. Choosing what to work on becomes difficult and a burden. A single priority is a mission, a clarity of work. Get this thing done, declare victory, move on.

Planning focuses our ideas

Planning is essential. But, not too much. Mostly in the next 90-day window (with apologies to Michael Pollan).

Humans are, with few exceptions, awful at planning. It’s impossible to see the future. We rely on our previous experience over data too often. Or, not enough. Or, in the wrong combination for this scenario. Beyond a few days, the world we operate in is too complex, people too hard to predict, and all of it is interconnected in surprising ways.

Even worse, humans easily deceive themselves with plans. It’s so easy to look at basically any kind of ambition or outcome and say “yeah sure, given 6-18 months this seems totally feasible.” (With apologies to our ambition, it probably is not feasible.)

Yet when we account for those hazards, planning is essential (apologies to Dwight Eisenhower). Most things won’t go to plan, but making one forces us to think things through, ahead of time. Outcomes without a plan are worse than outcomes from a plan that has to change when reality punches us in the face (with apologies to Mike Tyson).

I find that periodically looking 90 days into the future to think about what I want to focus on and outcomes I hope to realize is a pretty dang good way of setting myself up for “luck favors the prepared”.

Planning the work is an essential part of doing the work. An ambitious but uncertain 6-month idea becomes an ambitious but plausible plan in steps. Make a 90-day plan by breaking it into chunks. Organize them into a coherent fraction of the 6-month idea. Make trade-offs to decide what’s most important or risky. Start on the first thing. Rinse and repeat.

Iteration is part of planning. Unknowns, predicted and unpredicted, rear their head. Risk turns into caution turns into incidence. Nothing goes exactly to plan. So, we take another swing at the plan, armed with new information.

We’re always smarter than we were last week or last month when we made the plan. Sticking to the plan is foolish. Updating or overhauling the plan makes much more sense than trying to argue with it.

Planning is like writing. They both focus our thinking. An idea that flops when we take it from our brains to the page probably needs more work, whether it’s writing or planning.

Onboard new teammates with a 90-day plan


My new boss had written up a 90-day plan for me the week before I started. This was perfect timing. I was already starting to put a bow on my current work and my focus was wandering. Now my brain could start working on ideas for the next gig. Plus, I had a much better idea of what I’d start working on and how to make an impact than I did coming out of my interviews. It was one of the better emails I’ve ever received.