The Chaos Rolls Downhill

No, that title is not a reference to the current political situation. The current political situation, however, is partly to blame for my longer than usual period of silence here. Several times in the past few weeks, I sat down to write this post and and made the mistake of checking the news first.

Anyway, the chaos in the title refers to the somewhat controlled chaos of trying to get things done in a lot of workplaces, particularly ones that tend to be light on process. Everyone has multiple competing priorities, most projects require pulling together people from multiple groups, and no one is sure who is in charge of figuring out how to make it all work.

This isn’t a post about whether or not to bring in more process. There are advantages and disadvantages to running a process-light shop, and often the advantages outweigh the disadvantages.

But the following scenario is all too common, and can be avoided, even in a company that is light on process:

Big Boss wants something done and picks an arbitrary deadline based on, at best, intuition about how long it should take.

The goal falls under Little Boss 1’s purview, so Little Boss 1 sets out to make this happen. But to accomplish the goal, Little Boss 1 needs some work done by a couple of other departments, led by Little Bosses 2 and 3.

Little Boss 2’s department can accomplish their work in the time given, so that’s all good. Little Boss 3 has no idea if their team can do the work, because they have at best a rough guess about what the work entails and how long it will take. But Little Boss 3 doesn’t insist on time to scope out their part of the project. Feeling pressured by the fact that Little Boss 1 and Little Boss 2 both agreed to the timeline, Little Boss 3 agrees, too.

And so work starts. But no one really scoped it out, so there are a lot of surprises along the way. Little Boss 1 is nominally in charge of the whole thing, but is super busy, and doesn’t really understand the details of what Little Boss 3’s group does, anyway… and so requests for support often come late, and leave Little Boss 3’s group scrambling.

In short, it is a mess. But thanks to some extraordinary effort from Little Boss 3’s team, they pull it off, and meet the deadline. Big Boss is happy, but has no idea of the chaos the arbitrary deadline created, and is completely unaware of how fried Little Boss 3’s team is… so Big Boss asks for another project, with another arbitrarily chosen deadline, and the whole thing repeats.

And then, six months later, Big Boss wonders why Little Boss 3’s team has had such high turnover.

It didn’t have to be this way. Each of the bosses could have done things differently to save Little Boss 3’s team. Obviously, Big Boss could stop picking arbitrary deadlines. A lot of Big Bosses are under the mistaken impression that this is a great way to motivate people. It is not. It burns people out. It also selects for people whose lives can absorb frequent, unexpected crunch times, and this drives down the diversity of the team.

But the Little Bosses could push back, too. Little Boss 3 is the most obvious candidate to say something like: “I’d love to help you with your Super-Duper project, but I need to understand details X, Y, and Z a little better so that I can tell you what my team can reasonably delivery by your deadline.”

However, remember, Little Boss 3 is only getting marching orders second hand. Little Boss 1 was the person who first accepted the project. So really, Little Boss 1 was the first person who should have pushed back on the deadline set by Big Boss: “Let me go talk to the people who would need to work on this project, and confirm that we can get it done by your deadline.”

In an ideal world, then all three Little Bosses would meet, scope out the project, and go back to Big Boss with some options: “We can deliver this OK thing by your deadline, or we can deliver this Super-Duper thing a month later.” Maybe Big Boss has reasons for the deadline and will think the OK thing is, well, OK. Or Maybe Big Boss really needs the Super-Duper thing by the originally stated deadline, but now understands that achieving it will take extraordinary effort, and can try to make sure the team gets a reward at the end, or at least doesn’t get another unrealistic deadline dropped on them.

The amount of planning required to enable this sort of conversation is not as onerous as you might think. For most projects I’ve been involved in, it just takes one or two meetings involving at least one person who is used to thinking about things like lead time, risk, and dependencies. You don’t need to meticulously plan out all the details of the project. You just need to have the experience to recognize what the big chunks of work will be, how they depend on each other, and roughly how long they’ll take. If you’ve landed in a Little Boss role, chances are you have the experience required, even if you haven’t had a lot of practice at using it in this way.

But all too often, this doesn’t happen. Big Boss starts the chaos ball rolling by picking a deadline out of thin air. Little Boss 1 gives it another shove downhill by agreeing to a deadline even though there is work required by another department. Little Boss 2 jumps out of the way, and Little Boss 3 either can’t stop it or doesn’t see it before it flattens the team.

Picture of an avalanche
You don’t want to be at the bottom of this hill. Photo: Zacharie Grossen, via wikipedia

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