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A Roadmap for Hiring Rockstar Startup Executives

You’re an entrepreneur- which is American for “I’ll figure it out”- and you’ve figured out a lot: product, investors, your first customers, and the market. But now it’s time to scale, and to scale you need more people.

If you’ve been on the startup scene for longer than 5 seconds, you’ll have heard that hiring is really important. In fact, there’s a general consensus in the startup world that it’s the most important thing you’ll do. Everyone wants “A players”. And everyone wants the ‘best of the best’ in their executive team. But how do you get started?

Hiring Well is Hard

My old boss used to say:

Hiring is really f*cking hard. It’s like strategy: everyone thinks their good at it, but very few actually are.

Most roles are not very simple, especially when hiring startup executives. You need multifaceted talent in uncertain environments. But the more criteria you apply, the smaller the population to choose from.

Furthermore, the smaller the population to choose from, the higher the investment necessary to reach them (either in money or in time). Many CEOs stand by long time periods between hires saying the cost is worth it for quality, but the cause of those long periods may be a flawed process.

To try and figure out if your process is flawed or you’ve a high-quality bar, ask yourself, “is our average time to hire decreasing?”. All things being equal, you should expect to yield hires more frequently over time.

Do I Really Want to Hire Rockstars?

Let’s make sure we’re operating on the same assumptions:

  • You need to hire someone to do X, but X is ill-defined (e.g. startup or highly dynamic environment)

  • Hiring a Rockstar is really important to you/your organization

  • You can feasibly attract Rockstars (e.g. by brand, mission, team, compensation, equity upside, or some combination of these)

  • You’re dedicated to doing this really well

  • You have a ‘growth mindset’ about hiring and you’ll solicit feedback to improve

  • You’re personally going to spend a lot of time on this (estimates vary from 20%-80% depending on a variety of factors)

The Rockstar Process

If it’s just you doing the hiring and interviewing, there’s a 6-step cyclical process:

  1. Define the criteria for a hire

  2. Synthesize and clearly communicate those criteria to others*

  3. Design and build a process on how to fully assess those criteria

  4. Generate candidates

  5. Assess candidates

  6. Hire (or don’t)

  7. Repeat

*Others can include: internal recruiters, external agencies, your colleagues, friends, family, business contacts, investors. Remember, most Rockstars come through networks, not job boards.

If it’s you and a team doing the hiring and interviewing, and you’re the hiring manager, there’s an 8-step process (who knew adding more humans makes things more complicated?):

  1. Define the criteria for a hire

  2. Synthesize and clearly communicate those criteria to others

  3. Design and build a process on how to fully assess those criteria

  4. Train the interview team on how to (a) judge those criteria and (b) elicit signal from candidates

  5. Generate candidates

  6. Assess candidates

  7. Deliver feedback to interviewers to help them understand what they’ve assessed well and poorly

  8. Repeat

Why Am I Repeating?

The likelihood you do this process once and get the perfect hire for the lifetime of your organization is approximately zero. But it is possible to learn from what you’re doing in real time. You will often have to resynthesize what you’re actually looking for, maybe tweak the process a bit, or look for a different type of candidate you did before. You may hire someone you thought was a Rockstar and 6 months later you’re letting them go after a probation period because of poor performance.

Understanding what you got wrong and what you should have seen is invaluable to improving the next time around. If you’re hiring more than one person, you’ll be more effective and quicker to hire if you repeat the whole process. This becomes even more important when you’re hiring with a team, because you’ll rarely all have the same judgement or opinion on candidates. It takes time to come to some kind of singularity.

A Bit of Bedtime Reading

If you want to find out more, here are some great reads on hiring:

You’ll note 2 of the 3 books recommended are written by Googlers, and that isn’t a coincidence. Google more or less pioneered a new approach to HR (modelled more on academia than business), and in particular recruiting, that’s since spread across Silicon Valley.

Eoin spent just over a year working on hiring for Palantir Technologies in New York, Palo Alto, and London. He’s personally interviewed over 1000 people. Since leaving Palantir, he's returned to Dublin and set up Cantillon Labs, a firm that helps European entrepreneurs scale their companies globally. This post originally appeared on Medium in January 2017.

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