Part 3: Leading during a startup’s growing pains

I’m embarking on a series called Growing in High Growth that covers some learnings from my time at Cedar, an early stage healthcare startup. For those who would appreciate more context, check out the overview.

Photo by Matt Howard on Unsplash

A central paradox of startups is that in the pursuit of achieving scale, the primary outcome is not the joy of success but rather pain from the growth. The pains that you experience most acutely will depend on the inherent strengths and weaknesses of your particular organization with some common variations including:

• Pain from the large number of new hires onboarding in a short amount of time.
• Pain from the need to stand up processes that weren’t necessary a few short months or even weeks ago.
• Pain from the ambiguity of whether or not the crisis du jour is a standard bump in the road or an existential threat to the business.

The list goes on and on. Regardless of the specific combination you may be experiencing, the end result is a razor thin line between exhilarating and all consuming. Navigating that line myself was made far more complex by the fact that not only was I serving as a first time guide for others, I was also in a position to support or undermine its underlying sturdiness.

While I learned a lot about supporting others, the main takeaway was realizing you have to first help yourself, before you can be in a position to effectively help others.

How should you address bad news?

Don’t do this.

We often talk about early stage companies being “rocket ships” but in my mind, a more apt analogy has always been a “rollercoaster” as new heights can often be followed by precipitous drops.

It is during the times of hardship that your merits as a leader will really be established. While difficult to do well, I found time and time again that acknowledging bad news ends up being not just cathartic, but a demonstration of the consistency needed to earn the trust of the broader team. For me, one of the best representations of addressing a difficult situation was done by Cedar’s CTO (Hassan S.).

Over the span of a few months, Cedar had a series of departures, many of which came from engineering and culminated with the announcement that a highly respected tech lead was leaving. However, at a macro level, the attrition rate had been so low prior to that period that even with those departures we were still below the average for companies in our peer set.

It’s important to acknowledge how common it is to go down the following thought process:

• People will understand the positive perspective (i.e., attrition rate is relatively low)
• The most likely outcome of not addressing the issue is that people will eventually move on.
• The very act of addressing something gives it greater weight.
• Intentions are not always reflected in execution and acknowledging difficult news is particularly challenging to execute well.

Because all of those statement are true, it’s easy to take the path of least resistance and largely leave the issue unaddressed.

Hassan did not do that. In fact, he took the suggestion from a member of team to hold smaller group discussions since the bimonthly All Hands had grown too large. He scheduled four one hour sessions to ensure people had the opportunity to voice their questions and concerns. And because acknowledging bad news is a skill that can be refined, he did mini retrospectives after each session to learn how to improve for the subsequent one.

I was lucky enough to join for the majority of those sessions and not only saw firsthand the value of acknowledging mistakes in bringing the team together, I learned to think about earning trust as a function of consistent actions over time.

The reality is that consistency waits for no one. It’s easy to be consistent when things are good, true leadership is maintaining that consistency when things are bad.

Are you overly invested?

Maybe this is an obvious answer coming from someone writing a multi-part multi-page document on their learnings but I was truly surprised at the extent my well-being became caught up in the challenges of the role.

During a particularly fraught stretch, I found myself struggling to sleep more than 5 disjointed hours a night. When I managed to dream, they would frequently be work related and quite often, I would transition so seamlessly into active problem solving that I wouldn’t be aware I was awake for several minutes.

Stressful situations are an inevitability at work, especially in these environments. Given that, it is important to find coping mechanisms and strategies to improve your well being. While everyone will likely take a different approach (we are in the age of personalization after all), I turned to a combination of therapy, journaling and long distance running.

Developing tools to address stress is undeniably valuable, but equally important is identifying the root causes. In reflecting on that period, I identified two main sources:

1. A bout of imposter syndrome — Having never before been in a leadership position, the questions were natural and unending: Am I even qualified to operate in the role that I am? Was that mistake due to my lack of experience? Do I feel like this is a big problem just because I haven’t seen it before?
2. Lack of clarity on how much I was responsible for problems that spanned functions — As the number of specialized functions grew, coordinating solutions to the growing pains became increasingly ambiguous since it wasn’t always clear who was responsible for identifying and rolling out a solution. The end result was inconsistent implementations that either added to the confusion or extended exposure to the pain. Given #1, questioning if I should or could have done more simply added to the self doubt.

In hindsight, the best mantra for addressing these sources of doubt is simple:

You are not alone.

Who can you turn to for help?

Leadership often involves learning new skills that are not directly related to the ones you honed as you progressed through your role and is further exasperated by the slower feedback loops since it takes longer to see the impact of what you do. Given that, it’s easy to imagine how one mistake can lead to the next and quickly spiral out of control.

The reality of course is that you will make mistakes, literally pages and pages of them. The only way to break the cycle is to ask for help. The good news is it can come from many places, not even counting the support network you can build outside of the org.

Your Team

It’s quite appropriate to start with the place that I forgot to turn to the most. While I felt good about how I delegated domain ownership, it took some time to figure out a framework where individual team members could contribute to solving problems faced by the team as a whole.

As the team, the product and Cedar grew, the number of processes to define, dashboards to create, discussions to be had with other functions grew as well. While I was able to prioritize and focus on the highest value items, the things that started to fall below my personal capacity line became more and more painful to leave unaddressed.

The approach I took involved a recurring one hour meeting with the following agenda:

• Update: Everyone shares status updates on their outstanding items.
• Brainstorm: Collectively whiteboard any pain points felt by the team while doing their job since the last meeting. Discussion should focus on clarity and not prioritization.
• Prioritize: Each person votes on what they believe to be the top 3 pain points for the team.
• Delegate: I would weigh in to figure out the new top priority items to delegate and then assign someone on the team to be accountable for finding a solution, while factoring in personal and team capacity.

Beyond increasing our velocity in dealing with team-wide challenges, this framework had the added benefit of giving the individual PMs greater perspective on the challenges facing the entire team and why certain items they may be feeling more acutely had to fall below the line.

Your Peers

Since this avenue is likely the most common, I won’t deliberate too long.

However, I will reiterate that it’s important to cultivate a relationship with your peers where there is mutual comfort sharing frequent and direct feedback. By virtue of working the most together, even more so than your team or your leaders, your peers will have the most data points and examples to share. Lastly, discussing feedback with your peers tends to be an effective way of preventing imposter syndrome from spiraling out of control.

Your Leaders

It may sound a bit silly but I frequently forgot there was a limit to my accountability. The reality is that some problems are simply not yours to solve and learning how to differentiate between your accountability and the founders can reduce some of the cognitive load that can negatively impact your well being.

The framework I ended up using was to flag and discuss the problem, be explicit about who was accountable for the solution and remind myself that due to my limited vantage point and the fact that many of these decisions end up being judgement calls, I may not always agree with the solution.

To be fair, these conversations tend to be challenging. It can be hard to tell if you are accountable so flagging issues may feel like you’re either shirking your responsibilities or adding to the already full plate on the founder(s). However, leaving the problem unacknowledged is likely to create far reaching ramifications, not just on your well-being but also for many others in the company.

Beyond an upcoming bonus on enterprise healthcare, this part concludes the Growing in High Growth series (for now). As I mentioned in the introduction, I’m sure new experiences will help refine and expand these learnings into new areas. Even before then, I look forward to hearing how other people may have tackled these same challenges so please don’t hesitate to reach out!