How the Chief of Staff Role is like a game of Survivor (Part I)

The Chief of Staff (“CoS”) role within an early-stage startup is somewhat of a mystery. And while the popularity of this title has increased amongst “jack of all trades” people looking for strategy roles that don’t quite exist, the role itself has many perceptual hurdles within the companies four walls (or today’s zoom grids). Looking back, I liken my experience back the do whatever it takes, without getting voted off too early, reality show Survivor.

Jeff Probst, Survivor Host/Guru

Before I get into the specifics, a little background on myself. I started off on the traditional finance path, two years as an investment banking analyst and another three years serving my time in private equity. During these years I came to a crossroad that many in a similar position face, continue on the well worn financially secure path where my time, friends, and family would be an afterthought or go to more obscure route — following my passion to be in the “build things” ecosystem (whatever that may be). While in business school, the next years involved an intense focus on finding the right opportunities — but if you’re interested in how I broke into the startup world from finance check back in for another article.

Okay, now back to the CoS role specifically. I joined my first startup within 6 months of the company’s existence. This was going to be one of those rocket ships, I thought to myself. I started a month after my business school graduation with the grand title of “Business Operations Intern”. Alongside me were another three undergraduate interns and one additional MBA intern. Why join as an intern? In reality, this was a dress rehearsal as my primary responsibility was to serve alongside the CEO on whatever company critical company initiatives were necessary. I didn’t realize at the time that this was a de-facto Chief of Staff role, and here’s where I made some of my first big mistakes.

Lesson 1: The way you enter a company is going to define how people perceive you and your role

For those who do not tune into Survivor, the start isn’t unlike most reality shows. First appearances are critical to how other players will go about their strategy of who to align with and who to keep a watchful eye on.

It’s not unusual for the strongest players to get voted off first if they came off viable threats to win. Little did I know when I joined as an intern, I would be involved in all the intern related training and tasks. When I started to skip out on certain programmed activities, often to attend meetings with the CEO, I could sense that the rest of the team involved were beginning to think that I was “above my position”. Nevertheless, I shrugged this off and I had gotten what I wanted which was a seat at the executive table.

Lesson 2: Threats don’t just come from below, but also from above

Back on Survivor, the best players are keenly aware that their own fortunes can be improved by sowing doubt and weakness on their biggest threats. Even when those threats are playing the game to a tee, a sudden blindside from a coalition of contestants can have those players sent home without warning. About two months into my “internship” I was feeling really good. The CEO had given me more and more responsibility in all areas of the business, an encouraging sign of my performance and value-add. Similar to my previous roles, I took initiative before that had been asked of me and called on the support of the remaining team thinking that I had the power and justification as the right hand of the CEO. Wrong.

As I edged my way into more parts of the business, I could sense that certain executive members would leave me out of important meetings or email chains. Believing these were honest mistakes, I pressed on being included, reiterating my responsibility to the CEO to keep him informed.

By the end of month three I was ready to talk about my full-time role, and once again had only received positive signals from the CEO and COO on my progress. As we sat down for my review a few days later, this view suddenly changed. I had received some feedback from selected senior executives that I had encroached on their roles and showed a severe lack of EQ. What’s more they knew I was analytically capable for the job, but were unclear if I was a “culture fit”. The offer: extend the internship for two months while they evaluate my ability to play nice with others.

I’m not going to get into the specifics but this was an old-fashioned Survivor blindside. Not only has my EQ been a career defining strength in previous jobs, but this feedback had only been given at the last minute — when the votes were tallied to see who gets booted off the island. I mistakenly thought I had stashed away some “ hidden immunity idols” through my relationship with the CEO and through the Type A quality work I delivered day in day out.

Lesson 3: Be transparent and define your role early and often

A common complaint for a Chief of Staff title is the lack of definable requirements for the role. In my case, these lack of known guardrails led to suspicion and disagreement in how my position should and would be viewed be peers and executives alike.

When I joined I had been soft-served by the CEO that my role would be heavily cross-functional and strategy focused, a naïve jack of all trades dream situation. Looking back at some of my earlier colleague conversations I should have noticed some obvious red flags.

• First, in speaking about my supposed responsibilities several peers recounted similar pitches about their roles when they had joined the company. I should have caught those subtle cues, but my enthusiasm in starting in a new environment loomed large. Even worse, I failed a key Survivor test, a lack of empathy as my presence was now deemed a competitive threat.
• Second, many of my early tasks were informal. I often sat in the CEO’s office talking off the cuff and then went off in execution mode. Little did I know that our conversations never made it to the rest of the team, providing no context to those directly and indirectly involved. It’s almost as if I were sent to Island of the Idols and bestowed secret knowledge which gave me an ulterior motive — of course I would have a target on my back.

Third, if you’re not sure about your own job description then you better bet others will share in that confusion.

• My Chief of Staff title came out a necessity to define my role after the title of intern began losing its luster. Sensing some of this growing tension, my COO wisely asked me to write up my own job description. After failing to secure a Head of Strategy title, I stumbled across an article on Medium about the Chief of Staff role (thanks Scott Amenta) which seemed like an innocuous yet recognizable enough title to assume. After solidifying that JD with the CEO/COO, I felt very confident that the confusion would be put to rest.
• Last, but not least. Make sure that JD is shared with the team. Maybe call me naïve again, but I only learned during my critical review that my JD had never been distributed. So while I had thought the ambiguity had been behind me, the lingering questions about my role continued long after we identified and acted on a potential solution. There’s no room for finger pointing on this one, you don’t see the host getting kicked off the show.

Some key takeaways

What are some key things a would be or current Chief of Staff can do to avoid some of the early mistakes I made?

• Write up a clear job scope with your direct report (CEO/COO/etc.) that is also then shared with the rest of the executive team and any other relevant team members. Ensure that the team is bought into the idea or at least will not immediately reject the thought.
• Understand where you can assert your opinion, and when to “stay in your lane”. Sure, I come from a background in finance and may know a thing or two, but the Head of Finance controls that part of the organization and must and should be included in any relevant conversation/decisions.
• First impressions matter, and people often warm up as they see you’re not a threat but rather want to help make their lives (and the company’s prospects) even better. The role that I had been promised by the CEO had also been pitched to several other team members, creating an unknown and competitive tension. I also wish I took some real time to slow down and get to know my team members before going full tunnel vision on my responsibilities.
• There’s a risk of hoarding immunity idols (sorry Kellee). I thought I was safe from any threats given I had the perceived favor of the “tribe” leaders. Even leaders need to answer to the collective opinions of influential members of the team.
• Be humble. You will not get any brownie points for walking in and saying you have an MBA. Oh and respect the elders who have been through these experiences countless times before.

Assess the environment, know the players, form your strategies. And most importantly, don’t get voted off the island before you even get a chance to play.

Thank you to the CoS Network for banding together a group of like-minded individuals trying to navigate ambiguous lives. Special shoutout to my MBA classmate and Survivor contestant Kellee for the creative inspiration.

The game doesn’t end here, check back in for Part II which will go into more detailed strategies of how I was able to handle some additional minefields (both personal and external) to mature in the Chief of Staff role.