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03. Building a team
Why is HR so painful?!?!
You, trying to hire a team. (Source: Meme generator)
Where to start? First, with the bad.
If you want to grow, no matter what type of business you are, you’re in the HR business. And HR is approximately 1.6 million times harder to do than tech.
No matter how good you think you are at HR, this will be painful.
Why? Because, at the start, it will always be your fault. The key to HR is realising this early, because it is baked into startups from the very beginning — don’t let it kill you. You also need to realise you are the one who has to do it. No one else. Remember: don’t go mad and don’t get mad. It’s going to be your fault. And that’s ok.
This sounds melodramatic, so let me try and provide an anecdote that might resonate.
I once had the person whose business judgment I trusted most come and sit in our office as they were between gigs.
Their feedback was that people liked coming to the office but there needed to be a culture of ‘more excellence and client focus’.
I then had to hit the road. I got a verbal OK on a very big, company-changing contract overseas. We raised a round. Everything looked great.
So I thought I’d try and address this ‘excellence and client focus’ point by talking about how — now that things were going well — we needed to be mindful this was the feedback etc. Then I went travelling again to keep selling (see also: Chapter Two... haha).
When I got back, I had a full staff revolt on my hands, and the person who pushed for more excellence sent me an email telling me my personality had changed and I wasn’t nice or kind any more, and this was — among other things — a failure of strategy. The two colleagues I was personally closest to both used this as a chance to tell me about my (many) personality flaws.
I was not feeling very good about the world at this point.
As part of figuring this out, I called a mate of mine who is very senior at an extremely successful AI startup for our usual half-yearly catch-up. We were doing the preamble chat, I said I’d been on the road and that we’d hit this milestone.
Quick as a flash, he said, “so, did staff revolt while you were away?”.
“Yep”, I answered.
“Then everyone questioned your strategy”, he continued.
“Yep”, I said.
“Ahhh, the usual”, he laughed.
I felt approximately 863% less rubbish. And it made me realise:
Anyway, enough of the cheery stuff! What can you do? This chapter is everything I quasi-figured out along the way — and wish I had at my fingertips before my anecdote above. Don’t be me. Trust me, it is very hard to come back from being told you’re not a nice person. It won’t be fun. (On the plus side, you will undoubtedly have less personality flaws than me).
The go-to reading for this chapter is by , who used to run HR at Stripe. (And yes, taking HR lessons from Stripe is sorta like asking Michael Jordan how to win more, but it never hurts to see how the best did it).
Start with your mission and kumbaya sh*t
First, no matter how painful: have a mission. You may think it’s bullshit. That’s ok. But you need to believe. If not, no one else will.
A mission will save you time, keep your investors happy, help keep your staff from leaving, and above all, save you from endless people asking you what your strategy is. Plus, once you have this in place, you can go out and hire. How? Because it helps you figure out the core of your business. From there, you can slice off various tasks others can do easily.
It also lets you know in your own head if something is bollocks or not. People can see whether you believe the real thing or not.
The problem is that there’s also a lot of bollocks in the opposite direction masquerading as a vision.
You, sharing your mission with the team (Source: GIPHY)
And, above all: your mission can be difficult to figure out.
So make your mission something less bullshit, and something that’s yours.
When to do this is tricky. If we trust our mates at Stripe, you should do it after you can’t fit in a single meeting room. That seems a pretty good start.
Once a company can no longer fit into a single meeting room, it’s time to start writing down your operating system and its component structures. Before this point—when you’re still trying to find product-market fit, for example—it’s too early. There’s no point articulating why you exist 🤔 if you’re still trying to figure out whether you should exist.
Ask yourself if you should exist first (Source: The Simpsons GIPHY)
How? Well, the classic way to do it is to start with your company values ⭐, which form the basis of your culture.
There are a bunch of different buzzwords that will come at you at this point:
Put all of this together and you get a big perfect house 🏠. (OK, OK, maybe just a roof over your head).
Another way to do this is a little more bottom up — think through what you do without thinking about it, or maybe just the things you say waaaaaayyyyy too much, and they can be your values.
For what it’s worth, here are Bilby’s current values:
These are unlikely to make sense to outsiders — which is kinda how we came up with them:
So to recap, having a mission is not bullsh*t.
It makes hiring easier. It makes fundraising pitches much easier. It makes HR easier (as it’s less personal — it’s always better to have someone leave because they want to chase a different mission than because they think you’re a jerk). It also means you can depersonalise stuff from you. And you really, really want to do this.
Finding your team
First up, I want to get something out of the way. Finding people is the easiest, and the most fun part. Walking out of a job interview where you’ve met some mega uber genius, checking their salary expectations and seeing they are in budget, and then thinking through all the things you can now make is FUN.
The hardest question is not in finding them, but knowing you are financially safe enough to hire them 💸. Be aware that this anxiety doesn’t really leave you for a long time. It’s super tricky to know when you should or should not hire. Everyone has an opinion and those giving you their two cents worth aren’t the ones waking up at 2am stressed over money or HR issues.
So: make your decision, and try and make peace with it.
Make sure you have the funds to hire in the first place (Source: Most Expensivest GIPHY)
That said, let’s assume you’re going to take the plunge. Let’s go through some of the methods to find people. I will assume for the sake of argument that your budget will mean using recruiters is not an option. While they have access to wider networks and can actively search for candidates, they cost a lot and they’ll hit 🤛 your inbox hard for many years to come.
When do you hire? When you need it.
But know this: your first hires will probably be hit or miss — Swiss army knives often break in battle, yet broadswords are rubbish at opening wine. Knowing which one to hire when is far more art than science.
At the early stage, you’ll be broadly looking at three types of teams, with all very different types of people, and different needs.
The common denominator: you want people who are comfortable with ambiguity. But also, you want people you can trust. This is very hard, and it changes a lot. So the more you can find people from a background you understand, and the more you can specify what their role will be, the more likely you’ll get the person you want.
Where to find staff
The next thing you need to remember is that the best hire is different at different stages. Given this is a guide for early-stage folk, right now you probably want to maximise for breadth rather than depth. Get the Swiss Army knife. But remember, they will possibly hit limits when you grow, and that is your fault, not theirs. Different times need different types. You will need to help people adapt.
Claire Hughes Johnson called this “scaling to the call”—meaning that as a company grows, the individuals within it are called to lead in larger and more complex roles. Even if a person’s job hasn’t changed, the scope of it has, and the individual must ‘scale to the call’ to maintain their performance and produce results.
This sounds great. For the founder, it’s not always so good — because it is hard to put yourself in the shoes of the person who has just had their job changed on them again. My line is that if you scale, expect them to call ... you out. That’s a good thing when people do. Always better to have the bullets coming from the front rather than the back. And more importantly, it reminds you that with people, we as founders can always do better.
Assessing candidates
Ok, you’ve got folk from your list above. What next? Start with the basics — make a job description you’re happy with. Usefully, LLMs are excellent at writing these. Just plug in some basic biographical information about your company and your answers to the following questions:
Then put in salary and where you want them to work, and you’re ready to go.
How to see if they are good at their job or not is a much harder question. (Note: I will dwell on the tech answer to this with more detail in the next chapter because it is a bit different).
For me, what I look for is some sort of outperformance on something (ie: given X, you seem much better at Y than I would expect). The other thing I look for is that people are broad — ie, they’ve been able to jump around different things.
Note, as per above, this is all very dependent on the phase of your company. Early stage companies need breadth. As you grow, you’ll need more depth. Knowing when to shift is probably going to be a challenge for latter stages; the exception to this is your tech stack. I will write more on this in the next chapter, I promise!
Interviewing for cultural fit
Ok, so you have a rock star. Now, how will they fit in?
Judging this is much more art than science. But something that helps is not to use the interview process to figure out who you want. Start with a hypothesis (i.e., your job description document, see above).
Then cultural fit. If you feel like someone will learn fast and act as part of the team, then usually things can be pivoted.
The best interviews suss out how someone:
Here, the trick is to not get too abstract. Rather, think about how these values fit into what you are trying to make. There’s a Pablo Picasso quote they like to repeat at Stripe:
“When art critics get together, they talk about Form and Structure and Meaning. When painters get together, they talk about where you can buy cheap turpentine 🎨.”
(Note: Once your business is big enough that you can no longer meet every candidate, you have a quality control problem for cultural fit. The pros here recommend . This is sort of a sniff test. I haven’t got to this stage yet. When I do, I’m sure it’ll be awesome :)
Amazon’s Bar Raiser Programme explained
The Bar Raiser program was created to help Amazon hire consistently stellar employees.
Bar Raisers — as described in — are an exclusive group of interviewers who are considered good stewards of Amazon’s standards and culture. One Bar Raiser is included on every interview panel. The Bar Raiser is never from the team for which they’re performing the interview, and they run the equivalent of the hiring committee meeting. They can also single-handedly veto a candidate. Amazon invests heavily in training Bar Raisers to manage hiring decision conversations and to make sure interviewers are holding candidates to a consistently high and objective standard, and it’s viewed as a high honour to be a Bar Raiser at Amazon🎖️.
Onboarding
Recruiting can be expensive, particularly when you’ve gone through the effort of finding good people, and then they turn around and leave because they had a lame onboarding experience. So don’t scrimp here. The better the onboarding, the faster your new team members will be firing on all cylinders.
Follow the base outline below to make sure new hires feel welcome (Source: Brooklyn 99 GIPHY)
Onboarding checklist for new teams
Before Day One: Say “Hi” ✉️
Day One: Make them feel welcome 👋
Week One: Get on the same page 🎯
Month one and beyond: Keep checking in 📞
What to do with your team
OK, you’ve got all these people now working for you. Awesome!
But... now you are starting to grow a little. Or, you’re travelling a little more and the existing staff members don’t get to see you around the coffee machine as much.
That means decisions can’t be made face to face any more. Communication gets complicated because it flows through multiple channels, and trouble often breaks out as everyone outlines their preferred direction.
That usually means you need to find some way to manage people and get them to do what you want. And, as part of that, you suddenly become a manager.
This is emotionally really confusing and confronting. How do you stick it to the boss when, well, you are the boss?
For you, as a founder, this is when your team is likely to be rather unhappy with you. As I said at the start of this chapter, don’t be me. As much as possible, try and fix all of this stuff before it blows up — remember, when it does, you’ll be the one who jumps on the grenade.
How? I’ll outline a couple of possible ways below. But the key to remember is just do your best. Don’t question yourself. Don’t take it personally. Just don’t stop.
How do you make them better at their job?
The first and most obvious way to resolve any HR problems before they happen is to make everyone awesome at their job and get them to win.
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