Admitting Your Weaknesses And Hiring To Support Them

Here’s how to fight the fear, let go of control, and make moves towards a well-rounded company.

Admitting Your Weaknesses And Hiring To Support Them
[Image via Wikimedia Commons]

One of the most difficult tasks for any leader is hiring someone for a job you can’t actually do yourself. Whether you’re a founder of a new company or growing your team, at some point the skills needed for your expanding organization exceed your own experience.


Admitting that you don’t really have the skills the business requires is the first and most difficult step.

I have seen the benefits of this honesty first-hand many times. It happened most recently when I was working with the 16z portfolio company Local Motion and it came time for the cofounders to do some early announcements around their fleet-management company.

The cofounders possess engineering and design backgrounds from elite institutions, and they built their product–hardware and software–themselves. Both are also experienced mountaineers, and so they have this engrained sense of self-sufficiency, which is valuable both for building companies and scaling mountains.

When it came time to work with the industry press to tell the story of their company, in some ways they had to suppress their self-sufficient instincts. The founders were self-aware enough to know they had not done this before and agreed to enlist the help of those who have depth and breadth of experience.

The pros showed up and spent time learning about the team, the business, and the story. They came back with a plan, roles, responsibilities, and defined what success would look like. It was amazing to watch how the founders absorbed and learned at each step all those things, which they had not personally experienced before.

The lesson of letting go and letting professionals do their work is clear: delegating is never easy for most, but it is spectacularly difficult if you don’t know what the other person is going to do, especially when the outcome matters a whole lot. Still, you need to let the specialists into your carefully engineered world.


There will be moments of terror and maybe even defensiveness when you watch people talk about your product using tools and techniques you are unfamiliar with to connect with your potential customers.

The key to success here is avoiding these mistakes when you are in the hiring process:

1. Asking candidates to teach you.

A good candidate will of course know more than you. Their interview is not a time for them to teach you what they do for a living. The interview is for you to learn the specifics of a given candidate, not the job function. The best bet is to do your homework. If you’re hiring your first sales leader then use your network and talk to some subject matter experts and learn the steps of the role ahead of time.

2. Expecting a candidate to know or create your strategy.

It is fine to expect engineering candidates to know the tools and techniques you use. You wouldn’t, however, expect an engineering candidate to know your unannounced product, of course.

It is equally challenging to expect a new marketing person to have a marketing plan for your product. Even if you ask them to brainstorm for hours, keep in mind the inputs into the process–they only know the specifics you have provided them.

For example, don’t expect a marketing candidate to magically come up with the right pricing strategy for your product without a chance to really dive in. On the other hand, you can expect a candidate to walk you through in extreme detail their most recent work on a similar topic. You can get to their thought process and how they worked through the details of the problem domain.


3. Interviewing too many people.

You will always hear stories about the best hire ever after seeing 100 people. On the other hand, you rarely hear the stories that start with “we could not find the perfect QA leader so we waited and waited until we had a quality crisis.”

Yet these latter stories happen far too often. You should not compromise, but if after bringing a dozen or more people through a process you are still searching, consider the patterns you’re seeing and why this is happening. A good practice if you haven’t found the right hire after going through a lot of folks is to bring in a new point of view. Consider recruiting the help of a search firm, a board member, or a subject matter advisor to get you over the first hire in a new job function.

The most difficult part of hiring for a job you don’t know first-hand is the human side. Every growing organization needs diversity because every product and service is used by a diverse group of people. The different job functions often bring with them diversity of personality types that add to the challenges of hiring.

The challenge of making a human connection is one for the person doing the hiring to overcome. Often that’s the biggest opportunity for personal growth when hiring people to do a job you can’t.

Steven Sinofsky is a board partner at Andreessen Horowitz, an adviser at Box Inc. and an executive in residence at Harvard Business School. Follow him @stevesi.