If You See Something, Say Something: My New Mantra on Working in Tech

The best part about working in tech is that if something breaks, you have the power to fix it.

The worst part about working in tech is that things break all the time, and it’s up to you to fix them.

Popularized by the MTA, this is generally good life advice in tech.

Before working at Union Square Ventures, I spent four years at Stack Overflow. When I started there in 2012, the company was about 50 employees. When I left last year, we were rapidly approaching the 300-person mark. But when people ask me what I did while I worked there, it’s actually a pretty hard question to answer.

The conversation inevitably goes something like this:

Them: “You worked at Stack Overflow for four years? That’s so cool! What did you do there?”
Me: “Well…I started in sales but spent most of my time in marketing.”
Them: “Nice. What area in marketing?”
Me: “Um, a lot of different areas? I mean, it started with writing a lot of blog posts and case studies, then sort of morphed into events marketing and a few international launches, but in the end I was doing some mix of customer research, product strategy, and sales enablement. You know, whatever we needed at the time.”

With startups, it’s never quite so simple, is it?

After all, a lot can change at a company in four years. This is especially true in tech. Particularly when you work at a company whose monthly traffic metrics are consistently up and to the right.

And when the marketing team is 2 people (like it was in 2012), the job you perform is vastly different from when the marketing team is 20 people (like it was in 2016).

If you’re the kind of person who gets bored easily, there’s probably no better industry for you than tech. Because there’s literally. Always. Something. Else. To Fix.

But if you’re the kind of person who craves consistency and mastery around one particular process, this type of environment and industry is probably infuriating to you. Because things seriously change. All. The. Time.

I learned that I’m the kind of person who gets bored easily but also has a hard time adapting to change. Excellent.

By the end of my tenure at Stack Overflow, I got a lot better at accepting these changes. I stopped freaking out (as much) every time we rearranged our office and I had to change desks, and I started reframing how I thought about our company and my role.

I liked to imagine that Stack Overflow was a sort of cocooned animal that would morph into some new creature every six months.

Recognizing this helped me. I would tell myself that we were in a totally new place with new opportunities and new challenges. On a personal level, this meant that approximately, every six months, I would refocus and re-prioritize my own job to make sure I was still working on the most important things.

Hence, constant change.

Since then, I’ve learned that this is all pretty common. At Union Square Ventures, I have the unique privilege of getting to observe 65+ companies go through this process of growing and morphing and changing shapes.

Albert at USV refers to this idea as “leveling up” — like how when you play a video game and need to perfect one particular skill really well before you can achieve to the next level, at which point you need to perfect the next important skill.

I like to think of it like evolving one of your Pokémon.

With Eevee, you never know what you’re going to get. (Image via this blog post)

One day, you have a pretty normal dog-like Pokémon named Eevee that’s actually pretty weak in battle. The next, you may have a creature called Vaporeon that fights using water energy. Or one named Jolteon that uses electric shocks. Or a Flareon, which channels fire power. With each evolution comes new challenges.

When I was at Stack Overflow, these changes or evolutions came in different forms. Sometimes change would come with explicit directions from people around me as to how I should redirect my efforts. Sometimes change would happen so fast that it would take us all by surprise and we would collectively pause and regroup.

Sometimes we wouldn’t even notice that the change had happened at all. That kind was always the toughest to navigate.

Now that I’ve been exposed to a couple of these “six-month cycles” at dozens of other companies, it’s easier to see that all this morphing and changing and fire-fighting work is happening everywhere. This is part of what we hope our companies gain from engaging with our USV portfolio network and the reason why my job even exists at all.

Our theory is: If someone at one company figured out how to put out a fire in a certain way, maybe when another company “levels up” or “evolves,” that tactic can be useful for them too.

I know that line of thinking certainly helped me navigate the roundabout path of projects and jobs I had at Stack Overflow. If I hadn’t been able to talk with a marketer at Flurry about data analysis and best practices in survey development, I wouldn’t have been able to create a game plan to properly conduct research on our customer base. If I hadn’t gotten to know the PR lead at Foursquare, I would never have understood how complicated and thoughtful you need to be when telling your company’s story.

Of course, all of this is easier said than done. And it’s also much easier with a little perspective and hindsight, a luxury I have now but was not afforded when I was in the thick of it all.

I think a lot about what I wish I knew when I was there in the midst of it all. What would have helped me better navigate change when we were 50 employees, 100 employees, when crossing 200 people? But it’s hard to pin down anything precise.

The closest thing to advice that I’ve come up with is this: Pay attention.

If you’re currently working in tech at a startup, I think the best thing you can do for your company is to pay close attention to what’s happening around you. Be hyper-observant about any changes you notice inside the company and out, then take a minute to see if anyone else has noticed it too. If so, figure out whether or not that change may merit a behavior change or shift in focus.

The second thing I’ll say is that aligning on this stuff is key. After all, the sooner that everyone on the company agrees you have moved out of the “Eevee phase” and into the “Vaporeon phase,” the sooner you can invest together in the right strategy for that new phase.

With that, here are some basic questions to try asking yourself on a regular basis that may help you better assess which “level” or “evolution phase” you’re in right now:

• Recognizing change: How is this company different today than it was six months ago? What about from when I started?

• Identifying awareness: How have these changes impacted our goals and priorities? Do other people perceive these changes the same way I do?

• Adapting behavior: How can my team be the most helpful to the organization right now? Are we working on the right things? Am I?

In conclusion, I’ve decided that maybe startup life is less about having an “inside the box” job description that’s easy to explain and more about adopting the MTA’s slogan we see across NYC subway stations: 
If you see something, say something.

Like I said, the best part about working in tech is that if something breaks, you have the power to fix it.

The worst part is that things break all the time, and it’s up to you to fix them.