Learning by Shipping

One of the most difficult stages in growing your own skillset is when you have to hire someone for a job you can’t actually do yourself. Whether you’re a founder of a new company, or just growing a company or team, at some point the skills needed for a growing organization exceed your own experience.

Admitting that you don’t really have the skills the business requires is the first, and most difficult step. This is especially true as an engineer where there’s a tendency to think we can just figure things out. It is not uncommon to go through a thought process that basically boils down to: coding must be the hardest job, so all the other jobs can be done by someone with coding skills.

Fight the fear, let go of control, and make moves towards a well-rounded organization.

Nice try.

If you’ve ever tried some simple home repairs or paint touchup you know this logic doesn’t work—you only need to spend an hour watching some cable TV DiY show and you can see how the people with skills are always unraveling the messes created by those who thought they could improvise. The software equivalent can sometimes be seen as a developer attempting to design the user interaction flow in a paint program or PowerPoint. Sure it can be done by a developer (and there are talented developers who can of course do it all), but he or she can quickly reach their limits, and so will the user interaction.

Open up your engineer’s mind to embrace the truth that every other discipline or function you will ever collaborate with has a deep set of skills experiences that you lack. Relative to engineering, the “softer” skills often pose the biggest eye-opening surprise to engineers. Until you’ve seen the magic worked by those skilled in marketing, communications, sales, business development or a host of other disciplines you might not appreciate the levels of success you can achieve by turning over the task to trained professionals.

I have seen this first-hand many times. Most recently it occurred while working with the a16z portfolio company Local Motion when it came time to do some of the early announcements around the fleet-management company. The co-founders possess engineering and design backgrounds from elite institutions, and built the product themselves, hardware and software. Both are 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 the team, the business, and the story (professionals do that!). 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.

This sounds easy and pretty obvious. But if you put yourself in their shoes you know that this is not just bringing in a hired gun to get some press, rather this is hiring on a new member of the team and a new founding member of the family. What is vital to keep in mind, is that this kind of work is as important as every line of code and every circuit board. The lesson of letting go and letting professionals do their work is clear: delegating is never easy for most, but is spectacularly difficult if you don’t know what the other person is going to do and when the outcome matters a whole lot. Still, you need to let the specialists into your carefully engineered world.

There are moments of terror. You’re watching people talk about your product using tools and techniques you are unfamiliar with to connect with your potential customers. Even though it is a product, you are apt to feel as though this is a discussion about yourself. You question every step. You doubt the skills of the person you hired. You are certain everything will go wrong.

It is at that point—right when you start to panic and think that unless you do this yourself things will fail—that you need to let go. You need to say “yes” to hiring a person to do the work, and then let them do their best work.

Just keep reminding yourself that you’ve never done the job before, and that you’re role is to hire someone who knows more than you. Even when you’ve wrapped your head around that, there are a few ways you can get tripped up when you are 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 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 folks. You will always hear stories about the best hire ever after seeing 100 people. Those stories are legendary. 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. Again, 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’ve not found 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. Do you need the help of a search firm? Would you benefit from the help of a board member or subject matter advisor to get you over the first hire in a new job function?

These add up to the quest for the perfect hire. When it comes to engineering you give yourself a lot of leeway because you feel you can direct a less experienced person and because you can gauge more easily what they know and don’t know. When it comes to other roles you become more reluctant to let go of a dream candidate. This almost always nets out costing you time, and in a new effort time is money. That isn’t saying to settle, but it is saying to use the same techniques of approximation you naturally use when hiring people in your comfort zone.

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 highly analytical developer looking to hire a strong qualitative thinker for marketing, or the highly empathetic sales leader, is often going to face a challenge just making the human connection.

This human connection is a two-way street. Embrace it. Recognize the leap each of you are taking. Realize that the interpersonal skills required to call on customers every day are just different than the interpersonal skills used when hacking. The challenge of making that 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 (@stevesi)

Note: A form of this post originally appeared on FastCo.