Newsletter 97: what the hell is a Chief of Staff?
Ever since I announced my new role as a Chief of Staff at Docquity, many people have reached out asking what the hell is a “Chief of Staff” (CoS). I have to admit that it does sound like an elusive job. Depending on the needs of the founding team, it can mean many different things.
So I naturally wanted to summarize my thoughts and cover the following:
My journey to a Chief of Staff
What is a Chief of Staff?
Is a job as CoS right for you?
Founder’s perspective on CoS
When do you know you need a Chief of Staff?
When is not the right time to hire CoS?
Conclusions
From a dishwasher to a Chief of Staff
As an expat living in Singapore, people often expect me to have had a very smooth career journey. Something like, graduated ivy league school, got a great job, worked hard, and then got promoted.
But that was not the case. Instead, my career felt like a rollercoaster of ups and downs. In fact, most of the time, I was confused, did not know where I was heading, and my progress felt dissatisfying. Only in the past few years could I see how my career was directionally right. As Steve Jobs used to say, “you can't connect the dots looking forward; you can only connect them looking backward.”
It seems like the trick is to zoom out and have a long time horizon.
People are often taken aback whenever I share about the early days of my journey. After all, I got my first job at the age of 14 and worked at a construction site. Then, I spent seven years taking on various roles in the hospitality sector. In that period, I covered everything from cooking to housekeeping and dishwashing. It took more than seven years until I was able to get my first office job.
Coming from a working-class family, I was raised to believe that there is no shameful job. So I took all kinds of funky jobs to support myself throughout high school and uni. Waiter, dishwasher, newspaper delivery boy, cleaning jobs, and everything in between.
Luckily, I got two things right. One, I read a lot, which helped me to understand what’s possible and how to think for myself. Two, I had the right combination of being ambitious and naive enough to make bold moves. Those circumstances set the right foundation. A foundation that kickstarted the right career trajectory.
Today, I am grateful to have had all those experiences. A journey that led me to my current role as a Chief of Staff at a series C startup Docquity.
What is a Chief of Staff?
I do not think I can do justice to the role if I try to offer a generic definition. A definition that fits all types of companies and stages of growth. So instead, I will focus on CoS at series B or C startups because that’s what I have experienced and understand.
The first myth I want to debunk is that CoS is a glorified executive assistant.
Perhaps there are organizations where the executive assistant and CoS roles are similar. That’s completely fine. After all, each founder must tailor the role to his/her unique needs. However, in my experience, good startup founders consider the two roles completely independent. Executive assistants have more admin-geared responsibilities. Whereas the CoS functions as an extension of the founding team.
I like to joke with Docquity’s founders that a fire is burning at any time in a startup. The founders’ ability to identify which fires are worth fighting and which can be ignored determines the company’s success. Sometimes the founding team does not have the capacity to address all major fires. At moments like that, they need a trusted lieutenant to solve problems. Someone with a strong operational background, founder mentality, a bias for action, and a t-shaped experience. This is where a Chief of Staff fits well. No wonder the CoS role has reached a tipping point. In the past, it used to be a common practice in the military and politics. But today, we see early-stage startups and trillion-dollar companies embracing the role.
This leads me to my first point. The core job of the CoS is to solve problems. The problems could be across the entire organization. In my short time at Docquity, I have worked on various issues. To name a few, recruitment for product roles, organizing leadership huddles, managing design sprints, automating manual processes, building MVPs for new ideas, and setting up company-wide objectives.
Second, a good CoS would act as the connecting tissues between different teams. Teams that otherwise would remain siloed. The job often throws you into the room where the sausage is made. So you observe how important decisions are being taken and what insights led to that. Immediately afterward, the CoS must identify the right narrative. A narrative that will help her to share those insights with other leaders and teams. In my case, I was tasked with setting up Objectives & Key Results across the entire organization. That’s one example of how you need to align all teams toward a common goal.
“A great CoS enhances and raises the game for the entire leadership of the company. They do that by providing effective feedback on ideas and proposals from team members. Sometimes they push back when the analysis has not been well thought through. In those cases, they pitch in and help make them better. They also let me know when someone is doing an exceptional job so that I can praise them specifically and effectively…”
Influitive CEO — Mark Organ
Third, you must observe, collect, and then communicate insights concisely with the founding team. You are their eyes and ears across the org. So you have to pay attention to everything important that’s happening on the ground. The bigger the organization gets, the harder it is to be on top of what’s happening. That’s why the Chief of Staff needs to spend time connecting with people across the org and building trust. Over time, employees from different teams start sharing their honest perspectives. That starts with the leadership team but then trickles down to everyone else. The CoS gets a unique 360-degree view of what’s happening, a perspective that the founders may not have. After all, most employees might be afraid to honestly share what’s on their minds when their boss asks.
Fourth, you need to lead without authority. Whereas other senior leaders have large teams to look after, the Chief of Staff does not. In turn, many senior leaders do not take you seriously at first. Your ability to come prepared at all times, communicate clearly, listen attentively, and, most importantly, lead through influence determines your success. One way or another, you will end up working with different teams. Often, that happens when a big enough problem reaches the founders. If the problem persists, you will be sent to go and fix the mess. In the process, you must quickly investigate what’s happening and guide everyone toward a solution. At first, people will push back and reject your help. In their eyes, you have not earned the right to come in with guns blazing and dictate who needs to do what. No matter how much authority the founders give you, it’s never enough. It’s still your responsibility to build healthy relationships. Otherwise, you will have a hard time solving the problem on your own.
Fifth, you have the chance to do all kinds of random but important jobs:
Executive recruitment
Enterprise sales
Fundraising
Speaking at events
M&A
Coordinating external vendors
Investor relations
Reports
Or sharing your two cents on how to solve the company’s largest problems when the founding team asks for help.
Is a job as CoS right for you?
In my experience, you first need to have an honest talk with the founding team. That will help to understand their expectations. As mentioned earlier, different companies would look at the role in an entirely different way. Sometimes, the founders need a very smart and capable executive assistant. I personally would not like to handle people’s schedules and make decks all day. But some people do like that, which is fine. My perspective here is that you need to have an honest conversation and figure out a win-win solution. An agreement where the role a) satisfies the needs of the business and b) meets your personal growth objectives.
I think ex-founders who want to take/have taken a break from running a business can be an amazing fit. Entrepreneurs clearly remember the challenges of building great organizations from 0 to 1. In turn, they will empathize with the problems of the founding team. Ex-founders would have built the necessary skills and will easily fit as an extension of the founding team.
Other than that, here you go some of the core skills that I consider a must-have when hiring a CoS:
Clear communication and storytelling — half the job is being the connecting tissue top-down (founders to leaders) and bottom-up (staff to founders).
High horsepower — solving problems at a fast-growing business is quite difficult. In turn, you need the willpower and energy to go through what it takes.
Executive presence — especially relevant post series A when the c-level team starts shaping up.
Strong execution — your ability to convert strategy into results across all layers of the organization is foundational.
Experience building high-performing teams — as a CoS at Docquity, I spent 25% of my time recruiting rockstars. Sometimes for my team, but more often for other teams who struggle to bring the right talent in.
Comfort working in high growth, constantly changing environment — I cannot emphasize this enough. Perhaps at a later stage in businesses, i.e., post series D or IPO, the role becomes more stable. Yet, earlier than that, changes happen quite frequently.
Founder’s perspective on CoS
Lastly, I would like to cover a few points on how founders must think about hiring a CoS. When is the right time to hire one, and when isn’t?
When do you know you need a Chief of Staff?
Here you go a few thoughts on when it could be the right time to bring a CoS:
The organization’s complexity is accelerating. The team is getting bigger and harder to manage. In Docquity’s case, we quickly grew to 300 people across seven countries and multiple product lines.
Too many fires are burning, and addressing them is getting increasingly harder. So the founding team wishes they could multiply themselves.
The founders have way too much on their plate and are concerned about burning out. Once again, I am not talking about too much admin work. I am referring to many complex responsibilities. Challenges requiring executive presence, context, and quick execution.
When is not the right time to hire CoS?
Too early, say pre-seed or seed phase — if you are considering getting a CoS at that time, sleep on it. You most probably need a co-founder.
You have not reached product-market fit yet — you cannot outsource finding product-market fit. That’s the founding team's responsibility. The more people you add to the team, the more that will hurt your focus.
“This is a high-risk, high-reward hire. Most likely you’ll know when you need a chief of staff. You’ll feel that void where you wish you had someone helping with certain aspects of your job…”
Influitive CEO — Mark Organ
Conclusion
The CoS role is incredibly fulfilling for the right person. You are able to execute important projects while observing how other senior executives are leading their teams. Of course, there are frustrations at times. After all, you need to lead without authority. But the overall learnings are amazing. Not to mention the opportunities to have an impact. Collectively that outweighs the problems you may face.
From the founding’s team perspective, the right CoS can be an important partner in crime. A trusted lieutenant to solve the company’s most complex problems. A highly skilled SoC can, in fact, push the executive team to even better performance.