Learnings from Keith Rabois: Evaluating and Hiring Executives

Imagine you’re the CEO of a high-growth startup and you’re looking to hire your first CFO. You’ve never directly worked with a CFO as your background is in product and engineering. How do you hire and later manage an executive in a function for which you have no experience?

In this two-part piece, we’ll look at a few tactics for evaluating and managing executives based on feedback from Keith and CEOs at our portfolio companies. We’ll start with the hiring side in this post, followed by tactics for managing in the next post.

Hiring

It’s much easier to hire for a role when you understand how a great person for the role operates. As an example, it’s a lot easier to hire a VP of Engineering if you’ve been an engineer. If you don’t have a background in that role, there are a few ways to approach hiring.

Talk with the Best in the Role to Create a Baseline

As an example, pretend you’re looking to hire a CFO and you’ve never worked with one. The first step is to learn how a great CFO thinks, which you can do by seeking out the best CFOs and learn from them. Find the best 2-5 CFOs and have a casual coffee chat with them to understand how they think about their role and how they operate. The goal is purely to learn from them, not to hire them, as ideally the people you’re talking with are so great it would be impossible for you to hire at your current stage.

You may be wondering how you find these best CFOs. Start by asking friends and former colleagues; you want to talk to the person who is the first to come to mind for people as amazing. Talk to your investors as they see executives across many companies and may be able to recommend a great person to talk with.

Once you’ve talked with these CFOs you should have a good understanding of how a great CFO thinks and operates, which will help you pattern match as you interview your own candidates. It’s the same process regardless of what role you’re hiring, whether that be marketing, engineering, product, finance, operations, sales, legal, people, design or many others.

As a bonus, one of these people might be willing to become an advisor and provide you and your new executive with feedback. This is not the primary goal of the process, but may happen.

Have Someone in the Role Interview Them

You can have someone who is excellent at that role help you with interviewing. Let’s say you’re looking to hire a Head of People and you have a friend who is a Head of People at a different company. You could include them on the interview panel to provide feedback. This could be a trusted friend whose opinion you respect or one of the people from the last section if they’re willing to be more involved and advise you.

Work on a Real Problem Together

You can work on a real problem together for a couple days and have them write up their thoughts, whether that be a brief roadmap, problem statement and solution, or mocks. You’re embarking on a long-relationship together, so spending a few days working together on a real problem is a great investment of time for both of you to ensure there is a good fit.

Hire a Mid-Level Person

You can hire a mid-level person to start, whom you can learn about their function from, before hiring a more senior person. Imagine your engineering org is growing with dozens of engineers and a few engineering managers all reporting to you. You don’t need to hire a VP of Engineering or CTO straight away. You can hire a Director of Engineering whom you learn from before hiring a VP of Engineering. Alternatively, you can work closely with the existing engineering managers to understand more about engineering before hiring a more senior person.

Next Steps

Now that you’ve hired a great executive, how do you tell if they’re actually doing a good job at their function? In the next post, we’ll look at how to evaluate executives when you don’t have expertise in their domain.

In the meantime, please let me know what has worked for you with hiring and if you have any specific topics you want covered in the next post. Please reach out on Twitter with thoughts.

Thanks to Delian Asparouhov, Max Rhodes, Jeff Kolovson, Sadi Khan, Matt Fernandez and Keith Rabois for providing feedback.