You can't stand under my umbrella

Photo by Engin Akyurt.

This story takes place several years ago in a conference room at a well-funded startup.

There's a boss and a direct report having their weekly 1:1. The boss has been hired, in part, because of extensive startup experience. The direct report is early in her career. While it's not her first-ever job, it is her first startup job.

Her eyes are glassy and she's staring at the table. She says, "It keeps changing. Just when I think I have a handle on something, it changes again. When is everything going to stop changing all the time?"

She looks up, expectantly, at her boss.

The boss says, "It won't. And you don't really want it to. You're in an early-stage startup and if it stops changing, it's time to look for a new job because it means the company is about to die."

There's an unsympathetic read if you're looking for one. A boss, faced with a direct report near tears, refuses to say the words that would bring relief. Calming words, like "there's just one more major push before the upcoming launch but it will all cool down after that." Or reassuring words, like "don't worry, I'll take the project off your plate and go fence with the departments who can't agree on a timeline."

The boss in the story doesn't say any of those words. Despite the fact that the direct report desperately wants them to. And despite the fact that it would likely make their own life easier.

The boss in this story is Melissa. And the story is one we reference often. Not because of the unsympathetic read. But because of how hard it is to disappoint your team, more-so when someone is close to tears. And how hard it is to manage teams through change. Even when those changes are positive (new funding, new hires, new projects). But especially when those changes are negative (layoffs, projects cuts, spending freezes).

Stuck in the middle with you

Over the past few weeks, several leaders have reached out to ask for help with change management. The noteworthy thing is not that orgs need help working through change. That's pretty common. The part that caught our attention was that the middle managers were the ones asking for support.

Most change management plans start at the top. By the time middle managers are on the hook for change, it's usually a done deal. Decided somewhere else in the org. And now their job is to communicate to the team, get folks on board, and sort out any adjustments to their work.

When the middle reaches out to us about change management support, it means one of two things. Either they're annoyed at the decisions that are coming from the layer above. Or they worry the org has exhausted its capacity to handle change.

That second thing is a big problem. Skilled bosses listen to their teams. It's part of what they get paid to do. But when bosses feels like their teams can't stomach more change, it's not the change that stops.

Put away your shit umbrella

A lot of managers draw identity from their ability to protect their team from distractions. They call themselves shit umbrellas. Or crumple zones. We used to work with a VP Eng whose business card read, "Administrative overhead." All drawing from this idea that the people on your team are the ones doing real work, and your job is to keep all the noise away from them.

To a point, this sounds swell. If you're a manager who gets their team what they need to thrive, and clears the decks of needless distractions — hey, what can we say? Gold star.

But not all distractions are needless. Sometimes a distraction is just about who has to deal with Gary's 3am emails. But other times it's that something important has changed. Sometimes the market has changed. Or our customers have. Or our finances. Sometimes the reality on the ground has changed so fast, so profoundly, that our existing plans are obsolete. And when the shit hits the fan, an umbrella doesn't help.

When things are steady, and people know the right things to work on, teams are constrained by velocity. We know the course we're racing, the question is just how fast we can go. In that context, it makes sense for a manager to clear every obstacle out of our way.

But during times of significant change, teams are constrained by agility. It's not that velocity doesn't matter, it still does. But when everything has changed about the race, we need the ability to steer. A manager who tries to preserve velocity at all costs risks running us into a wall.

The kicker is that it isn't always obvious which situation you're in. Especially when change hits fast. Especially when it's change you don't like. And so there's a temptation to dismiss all that change as noise. As something to insulate your team from. So that they won't get distracted. And it's exhausting. For every fight you win to keep things stable, you wake up to some new email thread pushing more changes. There are times in every org when you have to fight for what your team needs. But when what you need is at odds with reality, you eventually lose.

AAA

The other day a man ran past us wearing a t-shirt from some Canadian armed forces unit. We didn't clock the regiment, but we both saw the slogan on the sleeve. It read:

Accept

Adapt

Act

We generally avoid military metaphors. Tech is very fond of self-describing in military terms (ahem "War-time CEOs") and it's always felt really self-important, disrespectful, and... gross. Selling software isn't war, and people shouldn't pretend that it is. But we will take good tools from anywhere, and this is a good tool. AAA (and other tools like it) are designed to cut through the noise and focus your attention on the decision you need to make. And you don't need to be military to understand how tough that can be.

Accept is the hardest step. When reality changes in ways that you're not excited about, you can get stuck for a long time in, "but I liked my old plans." Acceptance doesn't mean that you can't feel your feelings, just that you don't let those feelings keep you in denial. The faster you accept the new reality, the faster you can figure out what matters now (Adapt). And then, with your feet back under you, Act.

Organizations that can do this quickly and consistently are obviously more agile, and likely more effective, too. But organizations can only adapt as fast as their people do. And here's the thing: staring down a difficult reality and finding your way to acceptance is hard enough. But having a manager conceal that reality from you makes acceptance impossible. Whether that manager is trying to spare you the distraction, or the tears, or simply hasn't accepted it themselves yet, the result is the same.

So. If you feel like your team, or your org, has a difficult time handling change right now. If you feel like they are resistant, or misaligned, or lack the urgency that your current reality demands. A good place to start is to agree on what that reality actually is.

- Melissa and Johnathan