Maintaining authenticity as a leader while scaling a team 5x

In a previous post, I discussed my soft spot for zany metaphors that try to capture the surreal and exhilarating experience of working at a start-up.

Another trait that I’m known for on my team is telling long-winded stories “from, like, 10 years ago” that are tangentially connected to the topic at hand, and slow to get to the point. There is actually a philosophy underlying this approach to storytelling, and to some extent, my digressions are intentional. I’ll unpack the thought process below.

As the leader of a medium-sized Analytics function (~15 people at full tilt), my personal relationships with individual analysts are less close than they used to be. When we first scaled the team, I managed most of the analysts before building a middle management layer. As a result, the entire team had direct insight into my priorities, as well as my strengths and weaknesses as a leader. Even when I no longer managed these analysts directly, it wasn’t necessary to forge strong personal relationships — we’d already built them during our “trial by fire” start-up days, and had a wealth of shared experiences to draw from.

Given the recent turnover on the team, none of the current analysts have ever reported to me directly. But it’s still just as important for me to provide insight into the decisions I’m making — which, largely, are informed by prior experience. And, it also remains important to show vulnerability as a leader by sharing lessons I’ve learned the hard way, since those are often the greatest learning experiences. Since monthly coffees and occasional coverage for my managers aren’t enough to form the basis of such bond, I’ve had to find a scalable solution for building an authentic, credible bond.

Cue the wandering stories “from, like, 10 years ago.”

I try to keep the tone of my anecdotes approachable, and sometimes my approach to storytelling fails miserably. Our team meeting descends into heckles and giggles. But while the moral of my stories sometimes get lost, I don’t mind being the punchline of a joke if it’s a joke that brings us together. Camaraderie and psychological safety are just as important as the learnings I’m trying to impart, and laughter is an effective release valve.

This approach to establishing authenticity dovetails with another growth area for me, which relates to how I present our findings to the broader leadership of the company, including our leadership team. I’d describe this as prioritizing “truthiness” over the specific details of an analysis.

My role at Blue Apron has obviously evolved as we scaled the team from 0 to ~15. In my first few months at the company when our team was very small, I split my time between analysis and management. I got to know the data warehouse and customer dynamics really well, because I was the one analyzing them. Then, when we needed to grow the team quickly to support the entire business, my time switched over to 100% management as I focused on recruiting (first individual contributors, then a middle management layer). Most recently, a senior manager on our team was promoted to Director, further removing me not only from the details of an analysis but many of the strategic conversations about its objectives.

All of which is to say: my generalizations about the specifics of an analysis are often a matter of necessity rather than choice. The team’s scope of work is too broad for me to capture and precisely communicate all of the details, so I focus on persuasion and advocating for the recommendations that stem from an analysis rather than defending its methodology or clarifying nuances*.

At times, these changes to my role on the team — not having direct working relationships with 80% of the team, and becoming a consumer of their analysis (rather than a producer) — can be uncomfortable. In other words, the vulnerability I am sharing is authentic, but stemming from a different source than my peccadilloes and prior experiences. Moving further away from the data, the analysis, and team members can be disorienting and lonely. An unforeseen learning from my efforts to foster psychological safety have taught me that sharing my authentic self not only improves the well-being of the team, but my own job satisfaction as well.

* While the initial term “truthiness” coined by Stephen Colbert is accurate insofar as my characterizations often get minor details wrong, it’s important to note that I do my absolute best to highlight the capture the spirit of an analysis and the analysts’ best judgment.