Pick Your Boulders (Dear, New Ops Leader | Part 2)

Part 2 in a quick series on the things I wish someone would have told me about Ops leadership roles...

May 19, 2023

In case you missed it, this is Part 2 of a series dedicated to new Ops leaders. These are all things I wish someone would have told me when I was just getting started. If you’re just joining us now, read Part 1 here.

If you know someone ramping into a new ops lead role, share this piece with them (they will thank you!)

Part 2: Pick your boulders

Thanks to a former boss, I regularly think about the story of Sisyphus. If you haven’t heard it, in ancient Greek mythology, Sisyphus was a king, punished for his hubris. Hades sentenced him to push a large boulder up a hill, only to have it roll right back down, for ETERNITY.

(For all of you super productive Ops leaders out there, I know you agree that this might be our worst flavor of hell.)

I bring this up, dear new Ops leader, because throughout your tenure in this role, you will be ~~punished~~ presented with countless hills and insane boulders — and sometimes, you will have the opportunity to choose which are worth pursuing.

Some boulders will be worth it, and others won’t.

That large effort to implement a new financial management system that will allow you to finally get a handle on your cash flow and runway? Probably worth it.
That poorly-defined initiative to “improve how we work” company-wide? Slow down and think that one through.

But wait, isn’t that last one simple? Just a few templates and a wiki, right?

Sure, could be — but only under a few conditions:

Everyone you work with is a machine that can be reprogrammed with the flip of a switch.
The change is really simple, and you can just do it or …
The change requires some buy-in (and behavior change), but your entire leadership team is really aligned on following through, plans to model the new behavior(s), and will support their teams through the change.

The problems occur when you confuse #3 for #2 — and that happens, a lot.

That’s because behavior change is often harder than we imagine it to be. Also, your peers (and CEO) might be — ok, probably are — underestimating the complexity of what they are asking for. They may also be neglecting to internalize what the change means for them, personally.

For example: “we should improve how we do meetings!” could sound like a set of tools or guidelines that go out to all teams with standards that everyone follows (simple enough, right?)

Quickly, it becomes clear that the worst meeting offenders are on the exec team 🤭 (less simple)

Or, “we need to improve our hiring process” could sound like process tweaks for recruiters (great!)

But once you dig in, you realize it actually means more upfront planning and preparation is needed before roles are even opened, and that is a more complex problem to solve.

Know the warning signs.

Don’t worry, new Ops leader, you’ll become a better boulder picker over time.

And soon, you’ll even be able to spot peak “Sisyphus roles” coming in. (You know, the roles that are set up to ensure you’re boulder-pushing on Day 1). It’s when you hear things from a CEO like:

“I need an Ops leader to keep everything organized” (at our startup, where nobody knows which way is up)
“I’d like to move all of my direct reports under my new COO, so that I can just focus on Product (versus all of this ‘management’ stuff).”
“We don’t have anything documented, but we are going to scale headcount 5x this year. Our Ops lead is going to lead the charge.”

These are likely no-win scenarios – and do NOT let your confidence, optimism or excitement tell you otherwise (remember what got Sisyphus into this hell to begin with: hubris).

In all of these cases, things start off just fine. Some boulders actually get off the ground – but you know what happens next.

Boulders are everywhere — pick wisely.

No matter the ops role, it’s likely that by the time you arrive, the team is in some form of operational debt. You’ll see many opportunities to add immediate value, but before you jump in and start pushing — take a moment to ask yourself some questions.

“Will the effort I expend on this have the potential to return 10x the value?”
“Will this require unrealistic (or unsustainable) amounts of behavior change?”
“Are my peers (the exec team) really at the table here – engaging, owning pieces of this, stacking resources, getting curious?”
“Is this Initiative 3 on a list of things I’m going to try and do?”

Here’s a simple decision tree that you can use:

Misjudging the size of the boulder, or grabbing too many, is not the end of the world. But it tends to kick up lots of confusion and exhaustion around you, draining precious time and energy away from really important things.

So, focus. Your mental health will benefit from it, and your team will thank you.

And if you’re wondering what happens when you choose the right boulder: Yes, it comes rolling back down anyway, always. That’s startup life! 🤷🏻‍♀️

Don’t worry. You got this.

(Part 3 is here!)

Amanda