It’s Not a Skills Gap. It’s a Character Problem.

Prioritization is key to strategy. Strategy, to sum up, is deciding what to say no to. Every day, we make dozens, if not hundreds, of decisions. Each of these decisions has trade-offs. A coherent strategy is a lean or tilt in these decisions towards some goal.

It’s saying yes to one thing and saying no to another.

It’s prioritizing something and deprioritizing something else. Ideally, in a coherent way.

Prioritizing ourselves is hard enough. But when our direct reports fail to do it, it can get painful very quickly. You might think that prioritization is a skill — and it is. But the main reason our direct reports fail to prioritize isn’t due to a lack of skill. You can send them to decision science workshops all year long, and they’re not going to necessarily get better.

A lack of prioritization, and therefore a lack of strategy, can often be traced to a lack of virtue. It’s not a skill issue; it’s a values issue.

Thus, while I’ll identify three common anti-patterns that lead to bad priorities here, I need to emphasize that your expectations for improvement should be tempered. Give feedback, yes, but this isn’t a thing people can learn; it is a thing people must choose (especially the last one), and not all of them will do so. Be prepared to manage out.

Passing The Buck

Let’s say you sit down with a direct report and say, Project X is coming up, and we need to get a plan together for it.

Weeks later, you learn that they instructed their team to drop project Y, which they were working on, and switch to project X. This frustrates you because Y was important too.

What happened, obviously, is they failed to prioritize. Instead of thinking about which project should be prioritized first, they just assumed keeping you happy was the goal of their teams. They didn’t communicate to you any trade-offs that might need to occur, so you could make an informed decision. Hell, you don’t even really remember asking them to switch gears at all.

This makes you afraid to bring up new topics with them, because it will lead them to jerk their teams around.

The Cause

This is primarily due to a lack of courage. They don’t know exactly how to handle these conversations, and are so afraid of looking bad in front of you, they fall into a pattern of just trying to do whatever you say (or anticipate what you say) as fast as possible.

But you don’t want mindless automatons working for you. You want leaders.

The Fix

In terms of constructive coaching, ask your subordinate to give you a menu of options when you need to make a decision. Ask them to create information radiators/dashboards so you can easily check in and reality check what their teams are working on.

In particular, you might ask them to set up dashboards that denote churn so you can keep an eye on that. Tasks moved out of Doing into To Do or the equivalent.

This ultimately is work they ought to be doing anyway, but if they’re new, they may not have been instructed. If they’ve been in a leadership role for awhile and their go to strategy is to not lead at all, but instead reflect what they think their boss is demanding, then they’re not worth their salary.

Asks for the Moon

Another way a subordinate may fail is to — instead of screaming at their team to change gears all the time — they scream at their team to be in all gears at the same time.

(By the way, yes, I use em-dashes. I have nothing against AI used responsibly, but these posts usually use it minimally, if at all.)

This is a version of passing the buck, but instead of just making you out to be the unreasonable bad guy, they make their team the unreasonable bad guy. It’s another way of casting blame.

Why didn’t project X get done?

“Geez, I dunno boss, I asked them to do X.”

Ask about project Y? Same answer.

Because they did ask them to do both. And probably dozens of other things. They have tricked themselves into thinking leadership is asking for everything and screaming when nothing is done.

The Cause

Lack of courage can also play into this. They’re refusing to make a decision, but instead of implying you made it for them, they have their team ultimately make the decision (they just don’t put it that way).

There are only so many hours in the week. The team is going to spend those hours on something. Without clear direction, the team will do its best to fulfill what it thinks the direction really is. And they’re usually wrong, because they don’t have any big picture information to make that decision.

Another cause of this anti-pattern can be a lack of vision. The direct report legitimately has no idea where the company is heading, and thus has no idea how to prioritize competing concerns.

The Fix

The same constructive coaching can happen for juniors — ask for a menu of options, get clear feedback on current work so you’re not blindsided. In particular, for this pattern, look for overwork — too many assignments. If assignments aren’t showing up in the dashboard, look for hidden work, or side-gigs and side-projects the manager is promising to others and then just not actually writing down, but still asking his team to work on.

To help build vision in juniors, ask them to capture all the things they’re being asked to do (honestly, they should already have this somewhere in that dashboard). Rather than a menu of next steps, have them construct a roadmap for you of those tasks. How would they propose they work them down right now, and why?

Roadmaps are not that useful an artifact to actually follow. That’s because new information comes in, and priorities naturally change. But thinking in terms of them helps people see long-term pacing and goals.

Naked Self Interest

The final reason your direct reports are failing to prioritize is the worst of them: they’re using their teams to work on their own pet projects.

Perhaps they’re shopping around to other leaders in the organization, promising tasks in return for favors. Maybe they’re gunning for a promotion or a raise by doing anything but delivering on their actual commitments.

Perhaps they just think they know better than you.

(If someone thinks they know better than me, they’d better damn well know better than me. Because if I find out they misprioritized out of arrogance and were wrong, I’d be furious.)

The Cause

There’s not much to analyze here. These are folks who think they’re entitled to run the company, and are already acting like it with as few resources as they’re given. They’ll ignore your requests, find reasons to play you against your colleagues, and manage to squirm out of any accountability.

Give feedback, sure, but that’s just because you should use the same process to manage everyone out to guarantee a sense of procedural justice (short of someone threatening violence or using a racial slur, which are fire-on-the-spot situations).

The Fix

Well, the fix is implied in the cause. There is no fix.

But you can mitigate and catch early using the same techniques as above. Dashboards to ensure what’s being worked on is what is prioritized, and no promises are being made in return for favors. This only helps so much, though, because this particular manager is going to try very hard to hide side projects elsewhere.

Skip-level meetings mitigate this, and reconciling what those folks say is happening in their world with what’s on the kanban can catch this early.

Do You Need Help Prioritizing?

Have you had these specific issues pop up with your direct reports? Or do you want help actually learning the skill of priorities (what Drucker calls “effectiveness”), and you think your values are well aligned?

Is there a pattern you’ve noticed that I didn’t list?

Reach out at [email protected], I’d love to talk. If you want advice, the first session is always free and gives you a sense of what future sessions would be like, so you can try before you buy. We’ll work through what problem you’re facing and brainstorm ways around it.