What to think about when making your first hire

And every hire after that

Making your first hire - or any hire - is an exciting and nerve wracking experience. It’s awesome if you get it right and expensive if you get it wrong.

The easiest way to hire well is to not hire at all. Sometimes hiring just sounds like a cool thing to do, but if you can put it off, you should.

But if you absolutely need to grow the team, you can maximise your chances of success by thinking critically about who you hire, what they’ll do, how you’ll find them, how you’ll evaluate them, and how confident you are in them. Let’s dive in.

you, dealing with the consequences of a bad hire because you didn’t read this

0. Should you hire?

Everyone thinks that hiring will be quick and easy. You’ll quickly find the perfect candidate. They’ll immediately hit the ground running and solve the problems you need solved, which are clearly defined and ready to work on.

Anyone who’s hired before is chuckling now, because the reality is nothing like this. Hiring & onboarding are skills, and like any skill you won’t be good at them initially. Even when you are good at them, they still take a long time.

Once you get really good, you could go from defining a need to having a person in the role adding value as quickly as 3 months. 6 months is more typical. 6 months!? Yep: assume you’ll spend 6 weeks looking for the right candidates and arranging interviews, 6 more weeks interviewing and negotiating, 1 month from when the candidate accepts your offer to when they finish their current job, and then 2 months for them to ramp up. And these are optimistic numbers!¹

If you’re making your first hire, your company might not even be 6 months old yet. It’s very hard to imagine what it will look like in 6 months time. If you want to hire someone because you feel a burning need to get some task done today, will that need still exist in 6 months time? Maybe, but it’s pretty likely it will have fundamentally changed.

So before doing any hiring, you want to be really confident that you’re actually going to have concrete work for the person to do to justify the 6 month commitment just to get them started. To increase changes of success, I like to focus on finding the right people that will be competent and flexible no matter what tasks they’re given, rather than getting too focused on the specific tasks that need doing today.

1. Tap into your networks - aggressively

Before thinking deeply about which roles to hire for, think deeply about who you know that might work for you. If you have smart, capable friends, you can probably find a role for them. Don’t convince yourself that a specific friend would never work for you - maybe their current job is too senior, or maybe (you think) your company isn’t legitimate enough. And maybe you’re right, but you owe it to yourself to ask. Let them reject you, don’t do it for them. And if someone unfriends you because you kept badgering them to join your team, maybe you’re better off without them.

It’s tempting to put all your eggs in one basket here. If we just hire this one person, then all our problems will be sorted. Resist this, and instead try to find as many smart friends as possible. If you can’t think of at least 3 friends, acquaintances, or past colleges that could make good hires, then you should get better friends.

2. Hire for roles you know how to do

Often startups will say things like “we are great at building a product and supporting customers but hate sales - our first hire will be a salesperson”. They’ll hire someone to “do sales”, give that person no guidance, and set no standard for performance or expectations of outcomes. They will have no way of knowing if the person is doing a good job, so will blindly hope for the best. A year later that person will have achieved nothing and everyone will be upset. Learn from their mistakes.

It’s very hard to hire someone to do something you don’t know how to do yourself, so if you are doing that, you should be hiring someone who you trust to set the standard.² The much simpler approach is to hire people to do things you already know how to do. Set a baseline by doing it yourself, and then only hire people who will do the same tasks better than you would have.

This doesn’t mean you have to spend a year cold calling before hiring a salesperson, but if you haven’t sourced and closed some deals yourself, you’ll have no way of knowing if that person is doing a good job or not.

3. Recruitment is sales

It’s tempting to put a job ad up and wait for the applications to role in. This is similar to how it’s tempting to make a website and wait for the revenue to role in. Any salesperson in an early stage startup knows that doesn’t work - outbound marketing and direct sales is a thing. It’s the same with recruitment. Think of recruitment like sales before you have marketing support.

You can even use the language of sales to guide your thinking. Write a job description so that you have some collateral to send prospects once you’ve started a conversation. Focus on benefits to the candidate, and avoid feature bashing.³ Once you connect with a prospect make sure you follow up and are always conscious of the next step in the cycle. Ensure you are following up quickly, keeping your commitments, and respecting the prospect’s time (particularly if you decide not to proceed, otherwise karma will get you).

4. Have someone less desperate do an interview

When you really want to hire someone, you might overlook some legitimate concerns. Sometimes these are legitimate technical concerns (the person can’t actually do the job), but more likely it’s cultural issues (the person will suck to work with) that you convince yourself can be overcome. This is like going shopping when you’re hungry, but with much more serious consequences.

To mitigate the risks of a bad hire, it’s helpful to have someone who is less invested in the role do an interview. This could be a co-founder, a colleague, a trusted advisor, or a friend - frankly, you can make up their role in the company if you need to. Just get someone who you think is a decent judge of character.

They aren’t testing for technical ability, or for alignment with the role (though if that’s wildly off they should tell you). They are just giving a yes or no: is this a good person to spend lots of time with?

If you aren’t sure who should do this interview, avoid having the most optimistic (they’ll be least likely to say no) or most charismatic (they’ll sell the dream instead of evaluating the candidate) person in the company do the interview.

5. Hell Yeah or No

There’s a lot of things to be sure on before locking in a hire. You should be sure you want to hire anyone at all, sure this person is a great person to work with, sure they can do the job, and sure you’re willing to spend 6 months helping them be useful.

If you have any doubts, just say no. Once you’ve signed the employment contract, the costs in time and dollars to say no increase a lot. If you aren’t “hell yeah” about signing that contract, it’s not too late to say sorry and move on.

Things I have no advice on

I think recruiting is a process that you have to tailor to your company. There’s some things you just need to get right - I’ve tried to cover them above - and lots of things that you should just do whatever suits you best. For example:

• How should you technically evaluate candidates?

• How junior/senior should your candidates be?

• Will you take interns?

• What pay should you offer?

If you’re not sure where to go on these, follow your gut and it’ll probably work out.

Finally, a good post to read before each interview is Traits You Can Change, and Traits You Can't.

Good luck out there!

1. A month notice period is pretty hard to screw up, but all the others can very easily double if you don’t keep a close eye on them.

2. Often this is referred to as a VP level hire.

3. To some candidates, an office is a benefit, particularly these days. To others it’s a detractor. This makes it a good thing to focus on in a job ad. By contrast, saying something like “competitive pay” is feature bashing. Nobody will run a job ad that says “bad pay”.