The art, science, and labor of recruiting: Getting started

Congratulations, you are now an executive at a venture-backed company! You survived the presentations, the term sheet shuffle and the due-diligence. Everyone is calling you the Founder (which is true), yet you are actually a technologist, an engineer or just a “great ideas person” with an instinct for the market. But now you have to recruit a team; perhaps, for example, a VP Marketing (maybe you have never been in a room with a real VP Marketing and don’t really know what one does or how to assess his or her capabilities!) Worse still, you might be recruiting a CEO but have never really understood what a CEO does or how to appraise one. How do you evaluate a candidate, especially for a management role that you do not have great familiarity with?

Knowing what you don’t know is important: Unfamiliarity of a role’s key characteristics is not necessarily a barrier for assessment. 

There are specific skills for a position that are important, and recruiting someone who has performed well in a similar position in the right context, scale and timeline is very helpful. You can, and always should, find a knowledgeable person to help assess candidates for pivotal positions such as VP Engineering or Marketing. A good venture capital firm will have, in its portfolio, people who fill similar positions in their other companies; these people can advise you. Their input will not only help you assess candidates, but will also teach you a lot about the responsibilities and potential pitfalls of that position. These are things you may be unfamiliar with and therefore cannot appropriately judge. Not only will a knowledgeable person help you find better candidates (and maybe even candidates who can grow from the small five-person early stage team to the very different manifestation of the same role when the team grows to fifty people…or five hundred), their knowledge may help integrate the new person more efficiently and help you better appreciate the role.

Entrepreneur / manager conflicts often arise from entrepreneurs not completely understanding the real constraints, tasks and roles of their core executive team. A good venture firm will have portfolio founders who have run into this situation and can advise you. At Khosla Ventures we also have operating partners who may be able to advise you.

However, specific skills are not the sole indicator of a candidate’s “fit” within an organization, and this, in my experience, is where novice entrepreneurs make the biggest recruiting errors. Secondly, few entrepreneurs know how to interview a candidate. In this document, I’ll make suggestions and outline techniques I have accumulated over the years to evaluate candidates, moving beyond the positive-sounding surface answers to something much more substantive and useful.


Before we get started, let’s be clear about three things:

  1. Even if you follow every piece of advice in this document, you’re never going to always get it right. Shit happens. Even after thirty years of doing this, I still make these mistakes.
  1. I don’t want you to follow every piece of advice in this document! It’s not a blueprint – it’s a guide and each situation is different.
  1. You may not even have the opportunity to really interview a candidate or reference check them broadly because they are not interested, or they have other offers, or there is not sufficient time. Furthermore, you may not have enough leverage because your opportunity is not yet attractive enough. The realities of recruiting may differ from your ideal scenario.


So, how do you find out what a candidate actually did, how they were really perceived in their previous role, and what they might be capable of? How do you ask questions about a domain you do not fully appreciate the nuances of? Essentially:


How do you get beyond the answers to the truth?

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