Issue 36: 9️⃣ Elements of a High-Performing Chief of Staff
...from the perspective of a Principal
Welcome back, aspiring and current Chiefs of Staff 👋🏼
This week’s issue is brought to you by Ambient, a new AI Assistant for the Chief of Staff designed to return time to the Chief of Staff and help fast moving teams drop fewer balls.
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This week’s issue is guest authored by Lawrence Coburn, founder of Ambient, a new AI Assistant for the Chief of Staff designed to return time to the CoS, and help fast moving teams drop fewer balls. Prior to founding Ambient, Lawrence was the CEO and Founder of DoubleDutch, a Series F and later acquired category leader for Live Engagement Marketing.
What Makes a Chief of Staff Successful?
I’ve spent the last 9 months getting as close as I can to the Chief of Staff role in order to understand it (and to build purpose built software for the role). I’ve personally spoken to more than 200 Chiefs of Staff during this period, at companies and organizations of all shapes and sizes, not to mention attending meetups, summits, and conferences.
There are some wonderful resources and communities out there for Chiefs of Staff (such as Ask a Chief of Staff)! Most of these resources and communities are peer focused and experience based, which is an excellent place to start.
But I thought it might be helpful for Chiefs of Staff to hear one principal's perspective on a highly successful Founder / Chief of Staff relationship, and what made it work.
🎬 Setting the Stage
The year was 2015. The company I founded, DoubleDutch, was growing historically quickly (we were the third fastest growing B2B startup in the world) and everything was breaking, despite the exceptional quality of my leadership team.
One of my board members suggested I hire a Chief of Staff to help fill in the gaps (all the special projects that were falling through the cracks), and help me increase my bandwidth.
I happened to have the perfect guy on my team already. Matt had interned with us between his first and second year at Harvard Business School and came from a consulting background. He had joined us after he finished school and had deep relationships with everyone at the company.
Crucially, Matt had already made a huge personal sacrifice to join DoubleDutch - his previous employer had paid for his graduate school on the condition that he return to work for them when he was finished. When he decided to join DoubleDutch instead, he had to pay back that money, which was obviously a huge decision for him.
Put another way, not only did I know Matt really well by virtue of him being with us in the earliest days (our families knew each other, we hung out socially, we played sports together), I knew that Matt was heavily invested in our success.
Reason Number 1️⃣ Chiefs of Staff are Successful: There is built up trust even before they start as a Chief of Staff
I’m aware that many Chiefs of Staff don’t have the luxury of a preexisting relationship with their principal, but I see it as a huge advantage, and one of several reasons that I’m a fan of hiring a Chief of Staff from within. If you’re an aspiring Chief of Staff looking to make the leap into a new role, look internally at your company to see if there is already an opportunity to create the role or step into it.
🎢 The Rollercoaster
It is incredibly intense to work at companies that are going through hyper-growth. To make matters even more intense, we had surging business in EMEA and APAC in addition to North America - quite literally, the work never stopped and things were happening 24/7.
And it certainly wasn’t all wins - along the way we lost critical customers, key employees, there were some painful HR issues, and heartbreaking losses.
And through all the ups and downs, Matt never once broke my trust. He always kept my best interests front and center and he always did his best to keep me out of trouble. He had founder level access to all of the company secrets, but he used profoundly good judgment in how he used that info. It’s one thing to start with trust, but it’s another to never, ever break that trust.
Reason Number 2️⃣: Chiefs of Staff never, ever break their principal’s trust
The other thing about running a global, category leading business with a relatively small team was that 9-5 was never going to cut it. I remember many, many days that I would start my day insanely early with Europe, then work California hours, and then close out the day working APAC hours.
When stuff flared up, as it invariably did, I needed to pull Matt in - at all hours. And Matt always picked up the phone.
It’s not uncommon for founders to run through walls to try and make things work, but it’s far less common for non-founders to make those sacrifices.
Reason Number 3️⃣: Chiefs of Staff always pick up the phone
💸 Founders Sell and Chiefs of Staff Need to Help
Perhaps the most critical skill of a CEO / Founder is to sell. Of course you need to be good at selling your product, but you also need to sell your vision: to employees, potential employees, investors, partners, etc.
One of the ways that founders need to sell is through very high stakes presentations. In that final presentation for a 7 figure contract, or in our case, an 8 figure investment, you either pass or you fail. You need to be able to get your point of view across.
The consulting background probably helped: Matt was exceptional at making slides. I can think of two slides in particular that were able to simplify a complex thought in such a way that they literally helped close crucial deals.
Reason Number 4️⃣: Chiefs of Staff should be really good at slides/general story telling
If you don’t have direct slide making experience, think about how you can build or hone your storytelling skills. Being able to tell a crisp, clear narrative is a crucial skill that will benefit any Chief of Staff.
🧭 “Directionally Correct”
Another uniquely founder characteristic is that we are able to move decisively with incomplete information. I mean, we have no choice! As a tiny startup, often working on something that didn’t exist previously in the world, you are almost never going to have complete information. There is no market research study for the thing you want to do, but you have to move anyway.
Matt was unusual here: he thought like a founder. “I think that’s directionally correct” was one of his catchphrases and he was able to enthusiastically take action (e.g. open a new office in Phoenix, and not Austin! Or recommend that we buy tiny startup A, not tiny startup B), without having full information. Taking on an entrepreneurial and founder mindset allowed Matt to think more closely alongside me, which furthered our trust in working together.
Reason Number 5️⃣: Chiefs of Staff need to move quickly with incomplete information
✨ Master of the Special Project
Startup life is really a series of special projects. Functional lanes are not fully baked at most startups, which is why it often makes sense for new companies to hire “general purpose athletes” (people that are good at everything), rather than experienced domain experts.
Matt was the best I’d ever seen at the special project. He knew how to get in, get out, nobody gets hurt, on to the next one. It didn’t matter if it was a round of financing, a crucial hire, the decision to open a new office, a one off financial modeling exercise, or leading our offsite Core Values workshops.
Reason Number 6️⃣: Chiefs of Staff are also the masters of the special project
And speaking of Core Values, for Matt’s entire tenure with us, Matt was a powerful voice on the culture and values side of the business. He was there in the heady, early days when we were convinced we truly were building a new kind of company, and he never lost that passion for the culture side.
It was clear to everyone that Matt loved this company. And I think this gave him even more gravitas, even among the most senior execs (and we had some heavy hitters). Yes, Matt reported to me, and his primary job was to unlock me to move the dial, but the care that he put into the culture increased his influence.
Reason Number 7️⃣: A Chief of Staff’s values should be aligned with the company’s
🗣️ Not Afraid to Talk About the Hard Stuff
Let’s face it, giving upward feedback is hard and scary, and often a losing proposition.
Over the rocket ship and roller coaster years at DoubleDutch, we ran into some pretty dicey situations. Usually the hardest ones were personnel issues, but sometimes there were issues with customers, with investors, or with intra exec dynamics.
As an employee or an exec, it’s not the easiest thing to raise something unpleasant with the founder; you’re probably better off letting someone else walk into that uppercut.
But Matt never backed away from the hard convos. When stuff was broken, he would tell me - even if it was my fault, or involved people that he knew I cared a lot about. Maybe it was obsession with values, maybe it was the trust that he shared with me: he was always able to broach the trickiest convos with me with grace and maturity.
Reason Number 8️⃣: Chiefs of Staff are not afraid to talk about the hard stuff
📝 Do What You Say You Are Going to Do
In the early days of a company, particularly a good company, you really don’t have to hold people accountable. People are there because they are committed - they are there to change the world! With our first 20 employees, I more frequently had to tell people to go home than push harder. Early stagers are a special breed.
But as a company scales, the dynamic changes. There are more balls in the air, being fielded by slightly less committed people.
And from a “rhythm of the business” perspective, this is where Matt truly shone. He would run the weekly staff meetings, carefully take notes on who was supposed to do what, and help me follow up. It sounds simple, but when you have a million balls in the air and are traveling two out of five weeks, having someone who helped me keep the trains on time was incredibly important.
Reason Number 9️⃣: Chiefs of Staff help their principal hold people accountable
Ultimately, this last dynamic would be the inspiration for Ambient, the AI Assistant for Chiefs of Staff that my team and I are building.
This concept of accountability and helping fast moving teams drop fewer balls is so critical to a company’s success, that it seemed like a worthy problem to try and tackle with AI - not to replace people like Matt, but to give him the tools that unlock him to make even more of an impact.
In conclusion, here were the top 9️⃣ reasons Matt was successful as Chief of Staff at DoubleDutch:
I trusted him before he even started as my Chief of Staff
He never, ever broke my trust
He always picked up the phone
He was really good at slides
He could move quickly with incomplete information
He was the master of the special project
He truly cared about the company
He was not afraid to talk about the hard stuff
He helped me hold people accountable
These reasons help outline what a successful Chief of Staff looks like and can be the basis of any strong Chief of Staff and Principal relationship. Working on the skill sets that feed into each of these reasons will make you a stronger Chief of Staff and a stronger second in command to your principal.
🎥 Upcoming Events and Workshops:
February 27th: Defining the Chief of Staff Role
March 1st: Chief of Staff Virtual Coffee Mixer hosted by Ask a Chief of Staff, Nova Chief of Staff, Ambient (open to all!)
March 5th: How to Measure the ROI of an Offsite
March 21st: Generative AI 101
As a reminder, events and workshops are free for all Ask a Chief of Staff community members.
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