Surviving Startup Adolescence

Aviv Ben-Yosef
5 min readDec 6, 2022

Each startup is its own unique snowflake, and there’s no denying that. Nevertheless, after working with and talking to hundreds of founders, one can pick up many recurring patterns. While these might be harder to observe from the inside, an outsider’s perspective-which is naturally less entrenched in the details-can shed light on which problems are common and expected. One such scenario is what I’ve come to describe as “startup adolescence” when talking with my clients. It’s that limbo stage between the small startup stage and the this-is-a-business phase. These teenage years have a lot of ups and downs. While Paul Graham talks about an overlapping period as the “trough of sorrow” for business and motivation reasons, this article will share best practices to survive this as a leader of an organization.

Hitting Puberty

First, let me apologize, but I will probably overuse the analogy. It’s one of those things where finding the analogy helps one crystalize thinking even more. Anyway, things are simpler during the first years of a startup (infancy?). Again, for the sake of this article, I am putting aside business clarity and direction and discussing your team’s day-to-day management and leadership. Smaller organizations are simpler. Communication is nearly immediate. There is no room for politics to form.

In contrast, there are the later years. Once product-market fit is reached, the business machine starts to clarify, and growth is predictable, startups become “real” companies. While communication is not as straightforward, you already have processes in place to handle most daily needs. You can easily invest in clear career ladders, management training, etc. These two stages are very different, but the transition is even trickier.

Many people enjoy startups’ infancy or adulthood, but not the other. These are also the people who get lost during transition periods, which are volatile or considered less eventful by some ICs. Once your organization reaches this point, you, as the executive in charge, need to take active measures to guide your team across the chasm. I genuinely believe these formative years can be enjoyable if you view them correctly. In many ways, your company is metamorphosing entirely. As long as you’re inside the chrysalis, let’s make the most out of it.

Treating Acne

(I warned you about the analogy.) For teenagers, acne is problematic mainly because it is very visible, and everyone can see your “flaws.” However, that’s ridiculous given that one doesn’t have control over it, and it is a natural stage. Similarly, many people in startup adolescence find it problematic to admit that things are a bit ugly currently. There’s pressure from the industry around us to put on a facade that always touts how amazing things are, how cool your swag is, and show off the employee perk du jour.

To aid your team, embrace natural imperfection. Not every software release will go out smoothly. Some deadlines will be missed. You might be affected by a change in the market, but that is not necessarily the end of the world. When teams see uncertainty addressed and acknowledged, as opposed to being ignored, they are more likely to relax. I hear having less stress is an essential aspect of skincare.

Raging Hormones

Well, it might not be precisely the same, but many young companies are afflicted with people who seem to lean too hard in a certain direction. Just like the teenager that decries the entire world because of a bad hair day, this is how organizations get more dogmatic. Because things are changing and things are volatile, you often see team members become anxious. For example, they might be afraid they’ll lose the promotion to the first X (tech lead, engineering manager, engineering director, etc.) if they don’t try and mark their territory now. Or, you see politics starting to form where teams are not cooperating and becoming competitive.

This is where you, as a leader, have to mentor and guide your people about the changes happening and help them handle the innate volatility of this stage. With proper coaching, some people will grow with the company and “rise to the occasion.” However, there will be those who simply are not a good match for this-the employees who never enjoy larger companies. Finding out before the company matures and won’t have the time to handle these transitions is preferable.

Avoiding Peer Pressure

This is much more problematic for startups in one of the “hotter” tech hubs. People only share the major successes and highlights. Therefore, your employees feel like everyone around them is getting promoted, scaled up, or acquired. That is how so many junior employees get an urge to get promoted within a year or hop between companies relatively fast.

While the current cooling of the market helps relieve this pressure, it is always present. As a leader, you have to talk about it. Many of my clients have told me they hate doing it, but it is nevertheless part of your job.

Accepting Time

Lastly, we need to accept that some things take time. While you can accelerate some processes, you cannot rush everything. When you show a path forward and share the company’s vision and strategy, as well as regular transparent progress updates, you make it easier for others to “wait it out.” Just because things aren’t easy or perfect right now does not mean that’s how it will remain.

We’ll finish with a ChatGPT response that I personally found hilarious, depicting a startup coming to adulthood in the style of Tolkien’s Lord of the Rings:

The young startup stood at the threshold of its final journey, weary and battle-worn from the trials of its adolescence. It had fought valiantly against the challenges of the market, braving the treacherous currents of competition and the onslaught of competitors. But now, at long last, the time had come for the startup to seek its exit and pass into the realm of the established. Though the road ahead was uncertain and perilous, the startup’s team was steadfast and determined, ready to face whatever hardships may come. For they knew that even in the darkest of times, the fire of their passion and the strength of their unity would see them through to the end.

© Aviv Ben-Yosef 2022 — Originally published on the best newsletter for tech executives

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Aviv Ben-Yosef

I help startups triple impact-per-engineer with tightly-knit teams @ https://avivbenyosef.com