6 Things I’ve Learned as a Chief of Staff

Last fall, I changed roles at SalesLoft. Again.

I have been involved in a variety of business areas here (perks of being early to a fast-growing company), and while job changes do ping my OCD pretty heavily, the chance to take on something new and help define it is too good of a challenge to ignore.

Our co-founders, Kyle and Rob, had seen the role of Chief of Staff done really well at another company (shout-out, Mike Arrieta!), and felt SalesLoft could benefit from it. So they kicked off a new position: an 18-month role that is a blend of strategic and tactical, with an all-access pass to everything that happens in the inner workings of the business, from busy board meetings to hard employee decisions. It’s meant to train future leaders of the company, from the ground up.

In two months, I will hand it off to someone else.

I have had the honor of setting up a framework for the next CoS, working out some of the kinks (yeah, it’s weird for both sides when you’re suddenly all up in someone else’s personal business, even with permission), and have gotten to see in person how much hard work, guts, grit and drive behind the scenes it takes to grow a business. I’ve learned more in this role in the past 16 months than in nearly any other job I’ve ever had, and wanted to share a few of the top notes for others looking into it.

1. Truly important people don’t have to act like they’re important. As a CoS, part of my role is also executive assistant to Kyle, so I converse regularly with top-level executives. And some of the fanciest people I’ve met have also been the nicest: They learned my name, the name of our receptionist, and everyone else they met between the lobby and the meeting room. They took the time to write me thank-you emails for setting up meetings. They had sincere conversations, like everyone was at the same hierarchical level. They were understanding of mistakes and flexible with changes. These people own small private islands, but they never acted as if they were “too good” for anything, whether it was pouring their own cup of coffee or caring about a typo in a name tag.

The people who treat employees as “just the secretary” or feel the need to ask “Do you know who I am???” for minor snafus are not, with rare exceptions, genuinely important; they’re insecure, and it shows in their treatment of others. Something to keep in mind if you’re climbing a corporate ladder: Be nice to everyone, regardless of job level. That’s what truly makes you important to others.

2. You have to think about the fries. Before I took on the CoS role, I did some research (there are few things I love more than research, as you know), and met up with several current and former chiefs of staff. I was lucky enough to get an intro to Gabby Sirner-Cohen, now VP of People Ops with FullStory but previously Chief of Staff and Diversity Communications Lead at Google, and she told me this was her CoS mantra: “You have to think about the fries.” It’s a reference to an episode of “30 Rock,” where Tracy Morgan’s character asks his assistants for a burger. They bring him a burger. But no fries. They say he didn’t ask for fries, and he loses it and shouts, “Where are the french fries I did not ask for? You guys need to anticipate me!”

That, in a nutshell, is how to be an exemplary CoS (and a good direct report, in general). You need to think two steps ahead of the team you’re supporting, and get there before them. You not only answer that first question, but also anticipate and preemptively answer the second and third questions, too. This is super hard but it gets easier the more you work with someone, because you get to be intuitive about what they’ll likely need, how they think and what they’ll want to know. (Note: Nobody is 100 percent perfect at this, so don’t beat yourself up when you miss it. Just remember it for next time.)

3. Plan for everything … but be ready for anything. Yes, those of us in these types of positions are invariably planners; we thrive through organization and calendars and scheduling and details. But we’re in this role specifically because most of the people we support are not planners. They are usually visionaries, people with the determination to break down any wall and the charisma to make it look fun and easy. They are not administrative professionals. (Usually.) So they are going to make changes, lots of changes, lots of last-minute changes, ones that have wide-reaching effects that ripple out into the universe and unseat the small army’s worth of meticulous planning that you’ve spent months agonizing over.

Since you’re a planner, you have a Plan B. Maybe a Plan C. And even possibly a Plan D. But here’s where you’re flexible and ditch them all. Take a deep breath, jump in with some enthusiasm, and look at it as an exciting new challenge where you get to hone a completely unexpected set of skills. (That time you spent planning is now a sunk cost. Don’t cling to it.) And let’s be honest, the new place you end up at on your visionary’s abrupt side trip may actually be better than the place you were originally headed anyway. Nobody ever innovated by following the beaten path.

4. There’s a delicate balance between being proactive and being presumptuous. It can sometimes be tricky to decide when you should be making a decision on behalf of your CEO (or whomever you support), and when you should be asking her more questions first. On the one hand, it can be hard to get something urgent in front of busy people and sometimes you have to make a choice right now, and on the other, if it’s irreversible and you make the wrong choice, it can be hard to do damage control later. I’m here to say you should trust your gut instinct; there were multiple times that I second-guessed if I should be taking an action or waiting, and inevitably I should have followed that first instinct. If you aren’t 100 percent certain, trust your gut.

5. Relationships are everything. Aside from the fact that this is just generally good life advice, a good portion of the CoS role is managing by influence. You can’t do that if you don’t actually know people, if you don’t have trust and a genuine connection. Get to know not only the executive team (which is where many people would stop — see #1, above), but as many people at your company as you can. I work for a relatively small company at around 350 employees, but we used to be a lot smaller, and I’ll be the first to admit that it’s a struggle to keep up with new faces. We fortunately use Pingboard, which has a nifty little gamification feature on the mobile app that challenges you to identify your teammates, and I try to stay in the top 10 on the leaderboard there. (I’m in second place right now — I’m gunning for you, Hunter Harris!)

There’s also the challenge of maintaining early relationships, especially when you’ve changed departments or roles multiple times. You inherently build a stronger bond with people you interact with every day, so when you shift seats you also place a heavier burden on keeping up with the many tangential strings that make up our lives. It’ll be harder to remember (or even learn to begin with) what people’s children’s names are, and you won’t know right away if they’re having a hard week. To combat this, I try to loop through the office regularly and stop and just chat with people. I go to happy hours and departmental lunches. I swing through the kitchen for a soda and stop to talk. I keep up-to-date on as many Slack threads as I can (we have some specialized for the #LadyLofters, for example, but also #random, which is a really fun place to learn about your team’s sense of humor but also can be like going down a YouTube suggested video rabbit hole sometimes), and when in doubt, you can always bribe people with coffee. Or baked goods, in my case. Whatever your approach is.

And finally: 6. Listen, and learn everything you can. This role puts you in a unique position to be involved in the day-to-day workings of smart, experienced people who have been in the trenches and on the winning teams. Listen to their perspectives, how they frame a particular question, and even what kind of questions they ask or topics they introduce. I cannot count the number of times one of our executive leadership team has said something in a meeting, and I’ve been blown away by how they approached the issue or how they got to the heart of the matter in one sentence. It’s also incredibly instructive to watch how they run their teams, handle employee challenges and suss out high performers. It’s certainly leadership goals for me, and you should soak it up like a sponge if you get the opportunity.

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I know there are more things I’ve learned, and will still be learning in the last few months of this role. (I learn something every day, to be honest.) So I’m starting with these six, but not to worry, I’m sure another post will pop back up again later when I wrap up my role — and my thoughts — in March and take on a new challenge at SalesLoft. Stay tuned!