Recruiting strangers to join your technology startup

Startups are hard. Finding people who want to work in them is easy. Finding people who are capable of working in them isn’t.

Between 2010 and 2015 I built and lead the operations and support functions of a FinTech startup until it was acquired for £105 million. I interviewed hundreds of candidates to join a small and fast moving team in a high intensity company. Of those who joined us, many flourished while some did not. Here’s what I learned.

Early stage startups can be intense, stressful, demand long hours for little pay, lack job security, and can be both very rewarding or very painful depending on the challenges and successes of the business in any given week. There’s a reason why startup teams are often portrayed as young people living together in a small office, working long hours to pump out iteration after iteration of their product. If you’re looking for a nice 9–5 with a great salary plus bonuses and work-life balance, a startup probably isn’t for you.

For those reasons and more it is important that you find the right people to join your team. If you don’t manage expectations from the start you might end up with unhappy people who left safe and secure jobs for what turned out to be their worst nightmare. For the sake of the company it’s even more important to find people who are self motivating, independent, highly capable, and require little management other than to be pointed at a problem and told to ‘go take care of that’. You need the right mix of creativity and discipline. People who will find ways to make things happen without going off on an unproductive tangent. People who get things done.

Startups are usually short of resources, time, and money. Because of this you need strong people who can work on their own to achieve the company’s goals. There is nowhere for weak people to hide in the way they can in large corporate environments. If someone isn’t pulling their weight it shows quickly and obviously.

It’s hard for me to call it a mistake as the long term outcome delivered three hugely valuable assets (people) for the company and local workforce, but in the early days I took on three trainee apprentices through local government schemes. In the fast pace of a startup taking time out of your or your team’s day to support and train people is a huge time sink, even if the long term results are highly-capable professionals with the right skills and attitude towards work. Mistakes will be made and you’ll need to spend additional time recovering from them. You simply can’t carry the weight and still move fast.

Good but untrained people with the right mindset are an excellent investment in larger companies but in a startup you need experienced people who can work on their own to deliver results. Whether you’re looking at apprentices, graduates with little or no work experience, or junior people with a year or two of experience, think carefully before taking a chance on them. Yes, they can and most likely will do great things in the long term, but can you afford to invest in them at the same time as investing in your company?

Other than the legalities of discrimination, excluding or favouring candidates based on age, gender, or other background attributes will do you a disservice. Despite the stereotype, not all young people are fit for startups. Likewise, more mature and experienced people with families can certainly be an excellent asset for your team.

Suitability is always down to the individual candidate. Before hiring anyone be sure that they fully understand the demands and hours of the role, including overtime (especially if you’re expecting unpaid overtime), on-call requirements, lack of bonuses, and so on. If personal commitments make this undesirable then the company is not for them.

Having read thousands of CVs for startup capable people it is now obvious at a glance who has a chance and who does not. Reviewing these is a skill you will develop over time. My review is as follows:

  • Skim read each paper looking for relevant keywords related to what you need.
  • Asses job titles, companies, and time spent at each position, looking for a narrative of good career progression and recognition of performance while watching for warning signs such as unusually short placings or lots of moves without clearly stating contract work.
  • Skim read personal statements and profiles. These are largely useless but occasionally obtain some gems. Worst case, they might give you an ice breaker at the interview stage if they make it that far. (Tip for candidates, employers probably don’t care if you’re into mountain biking or spending time with your friends. This doesn’t make you stand out. If you lead a local agile group, have won awards, or do other non-standard things, write those down, otherwise you just blend into the minutiae.)
  • Look for clear statements of achievement. People who recognise their own achievements are more likely to achieve further success in future. Situation, task, action, result.

Once I have a reasonable shortlist it’s time to arrange an interview, either a phone call first if I’m unsure on a few things stated, or straight into face to face interviews.

The Interview

Unless you can offer a small paid project to assess a candidates suitability for a role, the interview process is the only chance you have of determining if a candidate is right for your team and more importantly, if your company is right for the candidate.

Over the years I interviewed hundreds of people, experimenting with different ways of conducting them. I researched different techniques used by large and small companies and tried to incorporate elements that I found interesting. Sometimes they worked reasonably well. Other times they were absolute disasters. I can only apologise for the early ones that ended like a car crash.

Eventually I found my own style. If it’s your first time hiring, or your first time interviewing without the rigid corporate interview processes that larger companies follow, I suggest you prepare by identifying exactly what you’re trying to get out of each interview and determine the best way to do that. My approach has two primary goals:

  1. I want to understand how people think
  2. I want to determine whether or not they will be able to work with the rest of the team under extreme pressure

That’s it. To do this I ask questions that involve telling me stories about things they’ve done, why they did it, what they learned, what challenges they faced and how they overcame them, and how they failed and then recovered. I do a brief technical verification of their CV through their storytelling but that’s not what the interview is really for. If you’ve lied about technical abilities on your CV but can answer a few questions successfully, well that’s why we have the probation period. If you can’t back up your claims once you start you’ll be gone pretty quickly.

The first 5 minutes of the interview I spend my time painting an honest picture of the company. I talk about how little resource we have available to do things, how little time we have to do them, the challenges we’re facing, and all of the other truths that might put somebody off. If after I’ve finished they’re still interested in joining the team then we’re off to a good start. Only at this point will I start to sell the strengths of working with us.

In my first few interviews I used the standard HR question set and included some technical assessment questions to fact check CVs. This approach didn’t serve me well and was soon abandoned. My approach now involves probing into their current and previous positions from their CV, asking questions to pull out details that give indications of how they think and how they perceive challenges.

My approach is conversational and somewhat informal. I purposely arrange seating so that rather than facing off over a table I’m sitting next to the candidate around the corner of a desk. This diffuses the confrontational nature of sitting against a line of people and in my view makes the candidate feel like part of a group discussion instead of an interrogation. (I never interview alone).

Rather than reel off a list of questions then make notes and disregard the answers as some interviewers do, I listen intently and ask further questions that explore the area’s they’re talking about, steering conversation in a way that attempts to pull out the information I need to hear, hopefully without prompts from me.

By the end of the interview my aim is to have established a reasonable assessment of character. My team are my second family and I’ll do anything to protect them. That includes from unproductive people who burden them, or personality clashes that will cause more problems than they solve.

Over the years I’ve seen some strange and undesirable behaviours from candidates. A few of the things I watch out for are:

  • Excessive use of ‘we’ instead of ‘I’. I want to hear about what the candidate did, not what the team did. Lots of ‘we’ tells me they were being led rather than leading. A startup needs leaders — people who will own their work and overcome whatever is required to get it done. A leader doesn’t need direct reports. Leading is a behaviour, not a function of management. Leaders in your team find ways to make things happen without bottlenecking at you.
  • Forced body language. I’ve seen several people using forced, ‘confident’ body language. Please don’t do that. It’s just weird. If you want to appear confident you need to be confident in your self and abilities. Moving from posture to posture in a robotic fashion does the opposite of what you’re trying to achieve. Relaxed and natural confidence is what I look for. Not to be confused with arrogance which is a huge red flag.
  • Lack of enthusiasm when describing previous roles and tasks. If you’re not interested in what you’ve done I don’t expect you to be interested in what you’ll be doing for me.
  • Lack of self reflection. When I ask ‘what’s the worst mistake you’re ever made?’ in relation to your work history, I really don’t care about what went wrong. Nor do I care about who was to blame. I’m looking to see if you can reflect on your own performance and identify areas for improvement. I want to see if you can learn on your own. And I want to see if you can blame yourself instead of the people around you, and be comfortable doing that.
  • The vague techno waffle of charlatans. If it can’t be explained without jargon then you don’t understand it.
  • Anyone who doesn’t actively seek out things to do when their work runs out, or anyone who uses a variation of the term ‘but that’s not my job’.

Making a decision

I have a simple rule for deciding if someone joins the startup team. If my reaction isn’t a definite and excited yes, it’s got to be ‘no’. If I don’t wish they worked for me already they don’t make the cut. If that means nobody gets the position this round then that’s OK. I’d rather keep looking and find the next great person than settle for anything less.

Aspiring writer, Cybersecurity Architect, Bug Bounty Hunter, Musician, Movie Producer, Failed Skydiver.

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