How the Chief of Staff Role is like a game of Survivor (Part II)
This is a follow up to Part I, in which I talk about my experience starting off as CoS in an early-stage startup.
For those who are tuning back in, let me first say this; the Survivor analogy stops at some point. Survivor is a game where there is one-winner at the end — but in reality, navigating the startup workplace isn’t about becoming the last one standing. Rather, it’s a journey to find out how to best co-exist and carve the niche where you feel both valued and can provide value.
Okay, now that we’re grounded again let’s get back to the story.
Last we checked, I had some hiccups to overcome as a CoS. And while the blindside I alluded to earlier at the time felt difficult and unwarranted, it was probably the best thing that could’ve happened in a situation like this.
Why? This allowed for a hard reset.
In Survivor, awareness is another form of power. Each castaway will often risk their own favor for just a sliver of inside knowledge of how others perceive them to be. In this instance, I was handed the golden ticket.
After some light (ok heavy) meditation, the first thing I did after hearing the feedback is go right to the sources of potential conflict.
Here are some of the immediate takeaways and steps I took:
- Reaffirm your commitment to why you signed up in the first place. Probably the strangest part of Survivor is the prevalence of ‘challenges’ that can be as random as putting together puzzles. We can debate whether these challenges make any practical sense, but in my case the challenge equivalent was the ‘review’ that made me question why I was in this game in the first place. Looking past this moment in time, I was able to recognize that the outcomes I had been looking for, exposure and responsibility in a fast growing startup, were readily available — a shift in approach was what I most needed to continue on.
- Become conscious of your default mode. Entering a new environment and trying to make a great impression while also delivering high quality work is difficult. Even if you pride yourself on having all the interpersonal skills in the world, in pressure situations you might find yourself on hyperdrive in your default mode — in my case, heads down work that demonstrates competency.
- It’s never too late for that hard reset. I knew that in my role I had inadvertently stepped on a few toes. Instead of letting these transgressions fester, I approached the individuals on the team to address these situations and ask for feedback on how we can improve going forward. Importantly, I used these moments to be more vulnerable and recalibrate relationships to a more personal vs. transactional level.
- Reposition your alliances. Following on the above points of friction, I began reporting directly to the COO (with a dotted line to the CEO) so he could ensure others across the organization knew what I was up to and vice versa. Part of the perceived threat comes with people not knowing who and where directives may come from. This is further challenged by the competing demands for the CEO’s attention, both external and internal, so having a purely internal manager helped make sure the information flowed a bit smoother.
With the above recalibration, fortunes improved dramatically. Even better — after the hard reset — my senior managers were also able to recognize points of friction within their own communication channels and took steps to improve transparency moving forward. A win-win.
Probing the Chief of Staff Network I realized that while my problems were personal, the root causes were fairly common across companies of ALL sizes. The CoS role is unchartered territory for all involved.
So, that’s it?
No, it’s not. Far from it. But I’ll close up on one more important piece. While some CoS claim they could hold the title indefinitely, most are trying to figure out where this role leads to next. I’m no exception.
As a Chief of Staff you get to experience many things, get in on the high level meetings, and can sometimes feel like the most important person in the company.
But in the end you don’t own anything.
Coming back to the purpose of Startup Survivor, it’s not about coming out on top, but rather finding the place you want to be. My quest for ownership is another big reason I butted up against executives in the first place and I knew that desire would not go away.
And that’s when my chapter as a CoS would soon come to a close. My managers could sense this too.
The final challenge: take the opportunity you’re given, even if it seems unfamiliar
About 8 months into my role, a spot opened up to manage our Direct to Consumer (“DTC”) business. As part of my CoS duties I was able to unearth some serious low hanging fruit of value in this part of the business, but never had the authority to take action on these insights.
With the goodwill I had accumulated over the preceding months coupled with the desire to be an owner, I was asked whether I wanted to lead the unit.
This is the moment where that inside voice creeps in. “But I have no background in DTC” / “Do I really want to be a growth marketer?” / “Am I ready to give up my inside access as CoS?”.
I’ve now been in the role for over a year and I couldn’t imagine why I ever had any doubts. Not only were the fears overblown, but the autonomy and flexibility afforded with ownership were the exact ingredients I had been looking for. And what’s become especially useful is the macro understanding of the business and existing relationships across functions resulting from my initial CoS position.
I won’t lie, there are some downsides of moving from an all encompassing role to a functional position but I imagine these tradeoffs will be a personal preference.
The end (or the beginning?) of the journey
I said this story would diverge from Survivor at some point, but not just yet. Part of the genius of the show is the prominence of the jury.
The jury consists of the survivor contestants from the current series who had been eliminated, but still have the vital task of selecting the final winner of the show. And why is this significant? Because, the ones who have the best shot realize that short terms gains, i.e. potentially taking advantage of a fellow castaway, might lead to long-term punishment in the form of the final tally.
Remember when I said that the blindside was probably the best thing that could have happened?
Well I do. Without that knowledge (and without that hard reset), I would never had had the chance to take back control of the narrative and earn the trust of the team to take on a leadership role within the company.
Okay, well that’s where this story ends, at least for now. If you’re still reading this and this resonates in some way you know where to find me.
