Lessons in Chief of Staff-ing

Some friends asked me what I've learned in my 9 months as a Chief of Staff at Oracle (Cloud Engineering Ops team, about 1500 people). CoS is an odd job - it's primarily about making sure that your executive, or "principal"--one single person--is successful. Your job is ensuring that their strategic vision is translated into operational reality. So you fill in a lot of cracks by juggling?strategic oversight, operational management, and executive support; whatever you've got to do so that your principal can focus most effectively on high-level strategic decision making. You're in the clouds and in the weeds in the same day, possibly in the same hour, figuring out how to?bridge the gap between executive strategic intent and ground-floor operational execution to make sure the org's immediate actions are aligned with it's overall goals.

If you like being in the mix, being in "the room", getting shit done, having broad business and strategic exposure, learning uncomfortably fast, being hair-on-fire busy...then it could be a good role for you. I'm really enjoying it! But it's not easy; reading back over this list I've made it sound kinda miserable. But while a lot of the job realities aren't much fun, they're not unique; they're all good practices for increasing your effectiveness in many other roles.?

So here's what I've learned about how to excel as a Chief of Staff. (Caveat: the CoS role has a broad set of potential responsibilities, so take this with a grain of salt; it might not match other CoS positions! My role is currently more aligned to the "run the business, make the principal's life less chaotic" end of the spectrum than the "be a strategic advisor and direct proxy" one.)

Be low-ego yet high-responsibility, and don't require a lot of attention

This is paradoxical combo; most people increase their ego attachment to a thing in proportion to how responsible they are for it.?There is a remarkable amount of stuff that happens in large orgs without a true owner, and if your principal said it needs to happen and didn't delegate an owner,?you're the owner until further notice. You must be wiling to take ownership/responsibility, possibly until completion, for stuff that doesn't really seem like your job, in areas that aren't your area of subject matter expertise.

Further, you won't be praised by your principal for a lot of this work, since a lot of what you do is meant to be invisible. You do the stuff your principal doesn't want to hear about–which means you'll mostly do things without telling them, and then only be on their radar when you're blocked and they must pay attention to the thing they don't want to pay attention to (so you get it done as quickly as possible).

Take care of people when you can, but also develop a thick skin, cause you'll give people lots of reason to be irritated

You affect others' perception of your principal. You can do a lot of good and create a lot of goodwill by ensuring that the needs and concerns of various parties are addressed quickly. So make hay when the sun shines. Followup fast. Take concerns seriously. Be super conscientious. Deliver good news with enthusiasm. Praise good work. Dole out favors generously. Invest as much as you can in good relationships, because the day will come when you've gotta make big withdrawals from those relationship accounts, and you need to avoid overdrafting. Sometimes you'll have bad news to deliver. Pretty much always you'll create work for people. You will butt into people's business with no warning and not much context, since your principal wants info or outcomes. You'll ask questions, you'll be a time suck, you won't be helpful, the thing will get done anyway, and you'll have been a fifth wheel...maybe? Who knows, it could be that you asking questions was helpful in moving a thing along–so in this case you're just a useful pot-stirrer or "bad cop", which aren't roles that everyone relishes.

And sometimes you'll need to divorce yourself from a personal sense of empathy. You'll know secrets–a reorg, a RIF, a upcoming change of management–that you'll have to keep to yourself. That means insincerely talking to people as if it's BAU, or pointing them in directions you know to be fruitless, or undermining them secretly. This does not feel nice, even if it's for the greater good.

Get comfy with ambiguity - aka "managing shit at the grey"

You're not in charge of everything you need to influence, so most of it's "at the grey". You've got to be aggressive about reducing ambiguity, while accepting that you'll live with a lot of it. Get used to saying "I don't know, but I'll try to find out".

Get comfy with change - the goalposts will move

Your principal gains context faster than you do, the situations are dynamic, and (surprise) people change their minds. In fact, two important parts of being an effective exec are 1. stating opinions with total conviction 2. switching directions without losing momentum. So just because they told you a thing with moral certainty yesterday does not mean that the opposite can't be "absolutely" true today.

So, since your principle is right, that means, lucky you, you get to be wrong, or at least ignorant. And there's no eventual vindication coming, since your goal is to ensure your principal's success. Get used to saying "you're right, I'm dumb, thank god you're here". (do keep in mind that's what your principal gets to say to their own bosses.)

Get comfy with urgency - everything comes down to the wire

Execs are so backed up that often the only things they're thinking about are urgent. Plus, you're insulating them from a lot of the details, so they ask you for things without knowing how long things actually take. ?

Even if you don't manage people, you manage people...and you'll only have the time to be a bad, absentee manager

You gotta get things done, so you've gotta leverage the inherited power you're getting from your principal. This is easy to do suboptimally. If you underdo it, your results aren't as good as they might be. If you overdo it by, you hurt your credibility (and your exec's), and randomize/deplete team resources that could have been put to better use.

Actually, a risk of involving yourself in a project is that it can create apathy--people feel insulated from the exec's judgment since you're in charge of polishing everything for your principal. So you need to delegate clearly, yet be ready at a moment's notice to take charge of messy collaboration or subpar deliverables.

Know when to ship things that are imperfect but good enough

CoS attracts a lot of "A" students, but your scope will be too broad for you to excel at everything; you gotta decide which classes you can get "Cs" in.?You must decide where to consider the task "Pass/Fail" vs something where real excellence and attention to detail is worth it. This means you won't put your best foot forward all the time, you will disappoint some people, and you've got to try not to feel bad about it.?

Case in point: this list isn't perfect, but it's good enough, and I've spent too much time on it already!