6 Questions to Ask Before You Take Your First Start-up Job

Photo by Jonathan Simcoe on Unsplash

August 2015, I had just graduated from Trinity College Dublin, with a degree in Economics. I had spent the previous summer interning with a 4 person VC fund based in Mumbai and had fallen head over heels for the start-up universe. Problem: I’d spent the last three years trudging through my economics degree and didn’t know how I, with zero tech experience, could access this world. Like many entering the world of full-time work today might be thinking, I decided the best way to learn about the inner workings of an early stage technology company was to go and work at one. So armed with my degree and no job applications, let alone offers, I moved back home and dove headfirst into applying to as many London based start-ups as I possibly could. That ended up being a grand total of 3 before I accepted an internship at a 5 person operation based in London and fell into a 20 month love-hate relationship with a firm that has shaped my outlook on assessing any opportunity I come across.

My advice to students or graduates looking to do the same is to think like an investor. It’s an early stage company — the likelihood is that you’re going to be interviewed by “upper management” and most likely the CEO/COO/CTO. Question everything. You have the advantage of youthful abandon as regards ideas and innovation, and are part of the demographic who are shaping face of technology to come. You are entering the world of work to gain skills and build your experience, but ultimately, you are making an investment. An investment of the years when you are capable of learning the most and completely giving yourself over to a company you truly believe in. So ask the right questions and really assess if the tiny company which you are going to end up staying up all night on a Sunday to make sure the customer gets a delivery/the product is ready to launch/the website is back up and running is one worth investing in. With entrepreneurship being the career buzz word of the moment, you have got to make sure you’re committing your time and energy to a place that is right.

So if I were interviewing for my first role with a start-up again these are the questions I would ask:

  1. When did you decide you were going to start {Company name}?
    You could ask them why they started this company 5 times, but founders will have that answer memorised like they’re reading it off the back of their hand. By asking about the precise scenario you’ll be able to understand if they faced this problem numerous times, couldn’t find a solution and so decided they NEEDED to build one. If the answer relies heavily on anecdotes about hating their previous job and wanting to be their own boss etc they are not going to be focused on building a product that solves a problem, in a way users love.
  2. What is your product development process?
    Whichever part of the business you are joining, understanding whether the product has been built through iterative testing and feedback loops with actual users or based off unvalidated assumptions is key. One would hope this was common practice, but I myself can admit to having been driven by my own assumptions and confirmation bias at multiple points in my life. It’s just human nature (behavioural economics was 100% the most insightful part of my degree; a short intro can be found here).
  3. How did you meet your co-founder and what are their strengths and weaknesses?
    Strained co-founder relationships can destroy company culture, product development and the company as a whole. Related to the next question — ask the people already working there about the cofounder relationship and if their styles of working are complimentary or very different.
  4. Can I speak to the people I will be working with?
    It is key that you meet the team that you will be a part of and not just the people who interviewed you. You will be spending more time with them than you will be with your partner, flatmates or parents (sometimes put together). They’ll be able to give you better insight into the culture, transparency and any issues the company may be facing than anyone else. You’ll also be able to ask them honestly about employee churn in the business. If they offer you a trial day, take it, it’s the best way to get this opportunity.
  5. How do you see the role I will be in developing over the next two years?
    It is important to assess how they see the role you will be filling progressing into the future. At an early stage start-up its all about the team, and founders should be thinking about how to retain the ambitious and intellectually curious talent they are attracting. If they aren’t thinking down the line to how your role will develop, odds are that they aren’t thinking very far into the future about quite a few things, and short-termism, kills morale, products and ultimately firms. You don’t want to be working in an environment where so many people come and go you’re worried to invest time making meaningful connections with your colleagues.
  6. How much of the share pool is allocated to employees, how is this structured?
    This question is particularly important for a team size smaller than 20. It isn’t about how many options you might get, but rather understanding how the founders view the value of their team. Everyone goes into a start-up knowing that you won’t be earning as much as you could have at a much larger firm. This question allows you to assess if founders value their team enough to let them share in the potential success and acknowledge their team’s commitment, no matter how junior that team member may be. Most importantly, it allows you to see how money focused the founders are. Yes, raising funds etc is key for growing their business but their customer and the product they are building should be the driving factor behind their decision making. An unwillingness to share even a tiny proportion of their stake in their business with the people helping build it, may suggest their motivations lie elsewhere.

Looking back at my time over the last 2 years, I learned more than I could have in any grad-scheme and got amazing opportunities to shape and build a product. I hope that by outlining these questions I can help you to make a more informed decision in your first major step into working life.

*I’m well aware that asking some of these questions may be daunting when taking your first job out of university, so if even if you feel like you can’t ask them, just keep them in mind when making your decision.