Why Your First Hires Can Make (or Break) Your Startup

There are many ways to fuck up when launching your startup, and hiring the wrong people is the most common one. Hiring is always a challenge in business, but large corporations have the resources to absorb a bad hire. For startups, however, a bad hire can be crippling. The high failure rate of startups (around 9 out of 10) tells the story. If you want to be part of the successful 10%, understanding why every hire is critical in a startup and what kind of profiles you should be looking for is crucial.

Critical Hire

I’m sure you’re familiar with the term ‘critical hire.’ In corporate speak, it’s that fancy title with outsized influence – the VP of Growth God or the Director of Disruption (whatever that means). Jokes aside, generally this refers to a role with strategic importance that directly impacts a company’s direction in a specific area, significantly improves KPIs, and is difficult to replace due to the person’s skills, experience, network, or a combination of all three.

I’m sure you’re already starting to see how this definition applies to everyone you hire for your startup. That’s because every hire is essentially a ‘Head of Freakin’ Everything’ until you reach at least 50 people. Why? Because in the startup trenches, it’s all hands on deck. In your early days, you need full steam to bring your idea to life, and only people who understand and share the early-startup mentality can make it happen. There are problems and resolutions that need to be delivered immediately – literally, now.

Someone might say this describes a very stressful environment, and that means you’ve grasped the point. It is indeed stressful, but it’s also the perfect environment for people with specific life values and mindsets. You need to be very clear about your expectations when you’re hiring.

Now lets talk about why, who and how.

Why?

You need a very strong understanding of why you need someone, the strategic areas they must cover, and the daily tasks they’ll be responsible for. Communicate this crystal clear (we’ll get to the “how” later).

For example, if you’re hiring an engineer to build your platform, you need to understand your customers, acquisition channels, and your primary platform (native app, web, desktop). Don’t worry if you lack technical expertise. Unleash your inner curious George during interviews and you will learn what you need.

As a side note, my main degree is in Law, believe it on not. But building my first tech business forced me to learn about microcontrollers, semiconductors, and more through interviews and supplier calls. Often, initial calls initial calls were like staring down a black hole of technical jargon and I didn’t even know what I actually needed. However, by the next call with another supplier, I had enough knowledge for a basic conversation. By the time I finished market research, I could even educate their salespeople (fast learning is crucial).

The key takeaway? Listen actively. Talk less, ask insightful questions, and treat interviews as workshops.

Moving forward, ask yourself if you can cover the needed business area without hiring. Is it a one-time task, a test project, or a core function? As a rule of thumb, don’t commit to a long-term contract to satisfy some fleeting fancy. If you need someone permanent, invest time in crafting a strong job description.

Next, let’s discuss the ‘Who’ section.”

Who?

As Geoff Smart said in his “Who” book – “Who, is where the magic begins, or where the troubles start”. As I already said, when you are tiny startup, every hire is critical, and Who is the most important part.

To illuminate the noise, ideally you want to focus on ex-founders, plan B is to look for people that has a strong sense of life in early stage startups, it can be someone who worked in a few very early startups already for a while and prefect, this is important, such environment. During the interview you want to look for “I like fast passed environment”, “My ideal life-work balance is to work 24/7” (trust me there are plenty of people enjoying such pace, check the Wall street statistics), “Company needs are the highest priority, no matter when”, “get shit done”, “looking for a full ownership”, etc. I was doing a course with 17h long days and 7 days a week for a month just to push myself to the limit, so I know what I’m talking about and I loved it.

In the same time having such people requires skills from you. First, is to be able to trust and delegate, any signs of micromanagement and they will run away faster than cheetah. You need to treat them as partners, you need to be fully transparent about every business aspect (marketing, sales, product etc). I always say that do not treat your team members as employees if you don’t want “employees” attitude.

Startup life is full of uncertainty, stress and work hard to chase the big dream so you need people that enjoy and thrive in such environment. As usual you must be very clear about that during the interview, you don’t want to waste your time and look for another person very soon, as it might kill your “baby”.

To cut through the noise, ideally focus on ex-founders, but those are rare breeds. Plan B? Seek out for people with a strong understanding of early-stage startup life. This could be someone with experience working in several early-stage startups for an extended period, preferably in a similar environment (this is important).

Here’s the Vasile’s interview bingo card:

  • “I thrive in a fast-paced environment” (translation: caffeine is my fuel).
  • “My ideal work-life balance leans towards working 24/7” (yes, these people exist – see Wall Street).
  • “The company’s needs are my top priority, no matter the time” (because deadlines don’t sleep).
  • “I’m a get-it-done kind of person” (we need warriors, not wusses).
  • “I’m looking for a role with full ownership” (because babysitting ain’t in the playbook).

Full disclosure: I did a course with 17-hour days and 7-day weeks once (talk about pushing your limits!). Let me tell you, I loved it. But that kind of hustle ain’t for everyone.

However, managing such beasts requires specific skills from you. Micromanagement is the kiss of death – they’ll bolt faster than a cheetah on Red Bull. Treat them like partners, with total transparency across the board (marketing, sales, product, etc.). I always say: Employees give you employee mentality, partners bring the fire.

Startup life is inherently uncertain, stressful, and requires hard work in pursuit of a big dream. You need people who thrive in the chaos. Be upfront about this in interviews. Don’t waste time on the wrong fit. A bad hire can be the final nail in your startup baby’s coffin.

Your ideal profile?

  • Ex-founder
  • Risk-taker: Fear of failure? Leave it at the door.
  • Self-driven: Forget hand-holding. They’re internal combustion engines, fuelled by hustle.
  • Results-obsessed: Forget empty promises. They live and die by the metric gods.
  • Full ownership: Micromanagement is a four-letter word. They crave autonomy and bleed responsibility.
  • Communication ninja (we’ll dissect this later, it’s a big one). Words matter. They gotta articulate a vision that rallies the troops.

Oh, and domain skills? Yeah, that’s a no-brainer. You wouldn’t launch a spaceship with a pilot who can’t fly, would you?

Next stop: How to Find such people.

How

It’s up to you how many interviews you want to have, but you want to check:

You might guess that we will start with job descriptions. Please don’t “look for a rockstar” unless you are hiring for your band. Job description must contain “You will” with the list of specific types of tasks that the person will be doing, those should be very similar to OKRs as they should be easily measurable, “grow daily active users by 20%” not “be awesome. “You have”, also be a list of measurable skills or knowledge that person can demonstrate. Once you have measurable requirements, you can use scorecards to evaluate all candidates equally to make the right decision. You can’t afford a random guess, it’s not a lottery, and again wrong hire can kill your business.

  1. Background with references. Always ask for their previous bosses, and if your position includes managing others, ask for references from people they managed. You want to know both sides of the coin. Your startup startup can’t afford a toxic environment, and each new person will have a huge impact on your culture.
  2. Competency – always ask “what, how and tell me more”. Ask “What” the candidate was doing in the last few companies. Here you are looking for tasks that might be similar to what needs to be done in your company. Theoretical skills are great but experience is better. “How” is the next big one as you want to know what is the decision-making process, reasoning and how the person approaches different problems. Do they consider alternatives or jump on the first option, it will also show you the experience and the level of domain knowledge. I already talked about “tell me more” when you want to learn things for yourself, but you need to be curious about details in the background, and ask a lot of follow-up questions. If it’s hard to pull the information, take it as a fail on the communication side.

For sourcing, always start with your network. The closer you know the person the better as it will help you to get an honest intel on their background, skills and attitude, which means fewer problems with reference checks. Don’t be shy to DM people on LinkedIn, it costs nothing.

Direct applicants from your website are the next option as it means the person has a genuine interest in your company, especially when your company is small and none of Google’s algorithms know about your existence.

The last is recruiters, but this is when you are really desperate. Recruiters are useful when you are hiring 20+ people at a time but not when you are building kind of a founding team.

This approach is not easily scaled, but this is not your problem for now, and if you do it wrong, and scaling might never be a problem. Look for partners who are natural communicators and you will get great results very soon.

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