The Two Must-Ask Questions Before You Join a Tech Startup

Should you leave your steady corporate tech job to join a risky early-stage startup? I’m not the first or last person to wrestle with this decision, and I wanted to share my thought process. Before you jump into a startup, there are two critical questions to ask: 1) who are the people that shaped the company, and 2) do you believe in the problem they are solving? There are lots of other questions to consider as you would in any job. But these questions are the essentials when evaluating an early startup.

Spoiler alert: I joined Nobl9, a fast-growing company focused on bringing Service Level Objectives (SLOs) to software teams to improve reliability and productivity significantly. 

Sure, pivots happen. But if you don’t believe in the current direction and problem that the company is solving, you shouldn’t join.

Don’t get me wrong; I loved my old job. I was a part of a 2,000 person publicly-traded tech company. I worked with wonderful people every day, and I always had a chance to meet someone new. “Corporate life” has a lot of positives, but I knew I wouldn’t challenge myself until I tried a startup. Making the switch to a small company was vastly different than I had ever imagined. 

Successful early-stage startups have tightly-knit, high-energy teams who work very closely together. You can access C-level executives and founders often and easily (which can be intimidating!), and it offers an opportunity to learn like no other job. You can have a massive impact on the company and how things change daily. I am shocked by how much influence I can have on the roadmap when I hear something from a customer or have an idea for the product. Impacting roadmap at this level rarely happens in larger companies.

Who are the people that shaped this company?

What makes a company successful is the people who shape the culture and set the direction for the future. No one has all the answers in the startup world, so leaders need to be open-minded and listen to feedback and suggestions. It is also great to have an engineering team with the “Can Do” attitude without running away from a challenge. Sometimes CEOs and founders stubbornly insist on the company’s direction and don’t listen or pay attention to countervailing advice. These executives will often miss the cues from the market. A prime example of this is John Antioco, the latest CEO of Blockbuster, who refused a partnership with Netflix because he did not believe in the business model of Netflix; we all know what happened to Blockbuster.

When I looked at the people behind Nobl9, I found a wonderful group of people. I suggest you research the founders and watch the interviews and talks they’ve given. (If you can’t find any, this is a strong signal as well.) Beyond the founding team, Nobl9 has brilliant engineers that consistently improve the product to the executives who are always available for a quick chat and open to new ideas. The immediate team members impact your success, and I am happy that I am a part of the Solution Engineering team at Nobl9. I am excited every day to get online and continue introducing Nobl9 to engineers and software teams struggling with reliability.

Do I believe in the problem they are solving? 

Let’s be honest: most startups have to change direction at some point. A great example of a tech pivot is Slack. They started out building a massively multiplayer game but quickly realized the game was no longer viable. They looked for another idea to pursue and suddenly saw they had developed a world-class instant messaging tool, which later revolutionized how the world communicates at work.

Sure, pivots happen. But if you don’t believe in the current direction and problem that the company is solving, you shouldn’t join. This question is even more challenging than the first because you might be looking at a pre-product startup. Hopefully, you already profoundly understand and empathize with the customer base and the market they are targeting. Try out the product or look for content online such as demos and tutorials. If the product is not ready, research the space and decide for yourself if the problem the startup solves inspires you.

Nobl9 is tackling a problem that virtually every company needs to be more reliable and move faster. I’ve worked with companies in the past that desperately needed a product like Nobl9 to shift their reactive approach to reliability to adopt SLO and be more strategic and efficient. If you’re curious about what we do, please check out this blog post.

But wait, there’s more!

You still should ask numerous other questions, but make sure you spend time on the first two before tackling the rest. Once you find some passionate people in the company and connect with the company’s problem, spend some time researching the investors. How reputable are they, and what are some other companies they are backing? For example, one of Nobl9’s investors is CRV, which also backed Twitter and Doordash. 

Startups aren’t for everyone. There are risks in being part of a startup, and you need to make peace with them before joining. There are more chances of failure in a startup vs. an established public company. There are sometimes long hours, and direction could change drastically overnight. You may have to do very different things than your “official” role. Be ready for anything!

For me, working at Nobl9 has been an exciting direction so far. I know the people behind the company will lead us to success, and I’m 100% convinced the problem we are solving is significant. Let’s SLO!

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