Picture the scenario: A startup has got 18 months of runway, a product that’s gaining traction, and a team of six brilliant people who’ve been pulling 12-hour days to get them this far. Now they need to scale. Fast.
So they do what most startups do: they start hiring like their life depends on it. Because, well, it does.
But a lot of early teams seem to follow the same route.. They optimise for skills and experience, fall in love with impressive CVs, and convince themselves that the person who crushed it at that big tech company will obviously crush it for them too.
Then reality hits. That ”perfect” hire struggles with the ambiguity. They’re frustrated by the lack of resources. They want clear processes that don’t exist yet. Three months in, they’re gone, and the team are back to square one, except now they’re three months closer to running out of money.
This doesn’t happen because the founders were careless or the candidates were dishonest, but because people underestimate what really matters in early-stage hiring. And what really matters isn’t what most people think it is.
The Reality of Early-Stage Teams
Running a startup isn’t just a harder version of working at an established company. It’s a completely different sport with completely different rules.
At Google, if you’re building a feature, you’ve got user research, competitive analysis, and probably three different teams who’ve solved similar problems before. At your startup, you’re making educated guesses based on conversations with a limited set of customers and hoping you’re not completely wrong.
At Microsoft, if you’re in sales, you’ve got a proven playbook, established pricing models, and a brand that opens doors. At your startup, you’re having conversations that start with “So, what is it you do again?” and end with you explaining why your solution is better than the things they’ve always used.
The difference isn’t just scale, it’s the fundamental nature of the work. Established companies operate with certainty.
Startups operate with educated hunches and the hope that they can figure it out as they go.
This creates a specific type of challenge that requires a specific type of person. Not necessarily someone with startup experience (though that helps), but someone whose brain is wired for ambiguity rather than structure.
The Resource Reality Check
Let’s be honest about what you’re asking people to do. Your head of product isn’t just doing product management. They’re talking to customers, analysing user data, helping close deals and so much more. (Check out my podcast episode with Daragh Kan a 2x first-in-the-door PM, for a real-life snapshot of this sort of thing)
Position descriptions are more like guides than guardrails. There’s no such thing as “that’s not my job” and there’s no time for it either. This is an environment where everyone has to do what it takes to win.
Add to that, the parameters of a role will most likely change as the business needs change. What you hired someone to do in January might look completely different by June.
This isn’t about finding generalists, it’s about finding people who can context-switch without losing their minds. Some people thrive when they’re doing five different things in a day. Others perform best when they can focus deeply on one thing for weeks at a time. Neither approach is wrong, but only one works in your current reality.
It’s also about finding people who are comfortable to not only context switch but can also handle a complete change in direction. As Tim Kreger said in a recent podcast episode “I’ve been in teams where you go, ‘ah, the business has changed its mind. We want to go this way.’ And everyone throws their hands up and puts their heads in the hands and go, ‘ah, this is dreadful. We just spent three weeks on this work.’ Whereas a good, resilient team goes, ‘yep. Cool. Let’s just move on and let’s keep going.'”
The Pressure Cooker Problem
A major challenge for every startup is the need to get their new hires as productive as possible as soon as possible. They don’t have the luxury of a gentle onboarding process or a six-month ramp-up period. When someone joins your team, they need to start contributing almost immediately, probably without a huge amount of guidance.
This creates a paradox. You need people with enough experience to hit the ground running, but enough adaptability to thrive in an environment where “how we’ve always done it” probably doesn’t exist.
The solution doesn’t seem to be compromise, but clarity about what matters at that particular moment in time.
Speed vs Quality is the Wrong Question
I get the sense that many early–stage teams think they need to choose between hiring fast and hiring well. They ask things like “What happens if we don’t find someone good enough straight away? Do we just hire anyone?” Which is a perfectly valid question, and one they should ask.
But when we dig a bit deeper, I generally find that the real issue isn’t speed versus quality. It’s that they don’t have some kind of framework that lets them recognise the right person when they meet them, and the confidence to make decisions quickly, when they do.
Why Process Actually Makes You Faster
Most startup people I’ve met give a sort of silent shudder when I say framework or process. And in my mind, the best recruiters dont push process for the sake of it, but find a way to gradually incorporate what is needed.
I know what you’re thinking. “Process” sounds like the kind of corporate bureaucracy people leave behind when they start a company. But that’s not what I’m talking about.
The best startup hiring processes aren’t about slowing things down; they’re about speeding up the right decisions. When you know exactly what you’re looking for, you can spot it quickly. When you have clear evaluation criteria, you don’t waste time second-guessing yourself.
Think of it like this: if you were buying a house, would you make faster decisions with no criteria at all, or with a clear list of your must-haves and deal-breakers (# of bedrooms, lock-up garage, cinema room, rooftop pool, 9-hole golf course….?)
Obviously, the latter. The same logic applies to hiring.
Before you post any job, try answering these questions:
- What does success look like in this role after six months?
- What are the 3-4 skills or qualities this person absolutely must have?
- What are we asking this person to achieve immediately?
- What would make someone completely wrong for this position?
- How will we know if this person is working out?
Do that upfront work, and you’ll make better decisions faster.
When to Optimise for Speed vs When to Dig Deeper
Not every role is make-or-break for your company. A junior developer who doesn’t work out is a manageable problem. A head of sales who’s the wrong fit can set you back six months.
For the roles that really matter, for the people who will shape your culture and trajectory, take the extra time to get it right. For everything else, move quickly and course-correct if needed.
Now, this issue is sponsored by the team at Taly.
The reason I’m excited about this is that it ties directly into all the things I’ve talked about in this issue. Tally allows hiring teams and TA people to go beyond a CV and see how a candidate will really show up in the role. It’ll show how they think, how they communicate, how they make decisions, and how they thrive.
Taly uses science-backed data and deep behavioural data to turn into clear interview prompts, onboarding tips, and role fit recommendations that you can roll out immediately.
In last week’s issue, I spent an hour or so talking with Peter Treloar, the founder of Tally. I’ll put a link here. So that if you’re one of the few that hasn’t seen it, you now can.
If you’re thinking more deeply about how to engage, attract, and retain your people, speak to Peter and the team at Taly. I’m sure they’ll be able to give you some insight and some answers through the platform.
Next week I’ll be talking about values. Company Values, Personal Values and Behaviours and more. So you can add a different level of thinking about that good old line – “Culture fit”
And as I’m sure you’re starting to see, all this stuff is interlinked. It’s all intertwined. By focusing on just a few of these areas, you can make your hiring, retention, and engagement of teams so much stronger.
Before you go, can you help me out?
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Thanks for being here. Have a brilliant week ahead.
Weekly newsletter drop: Wednesday 1:30pm – The Main Issue: Usually a comprehensive guide with advice for teams & talent, plus the latest podcast
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Simon
