On Hiring Your First Employees

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If there is one thing that will determine the fate of your company, it’s who you hire. Full stop.

Sure, luck and timing and your vision and your skills as a leader will all play a role. But companies win because they execute better than the competition and at greater velocity.

And if there’s one thing I hope you’ve learned by now, it’s that you can’t do it all yourself. You need a great team if you’re going to do great things.

If you listen to the people who have built successful companies you’ll hear this theme over and over: It’s all about the people.

“The secret of my success is that we have gone to exceptional lengths to hire the best people in the world.” - Steve Jobs, Apple

Unfortunately, platitudes such as, “It’s all about the people” and “hire top talent / build a great team” aren’t very helpful.

These cliches are easy to accept but much, much harder to operationalize.

For this post, I’m going to focus on the first step to building a high-performance team, namely figuring out who the heck you need to hire.

Having now worked with hundreds of hiring managers I can tell you that this is a lot easier said than done.

Far too often we *think* we know who we need, until we start interviewing candidates and trying to make hiring decisions. Then things get a lot more ambiguous.

Over the years, I’ve noticed that this ambiguity when a team is trying to decide whether or not to hire a candidate is often the result of not having enough information. Meaning, they interviewed the candidate but not about all the right things.

Now it’s time to make a decision and they can’t say for certain whether the candidate they just spent hours and hours interviewing has the one or two key things they need. This is obviously a colossal waste of everyone’s time.

The good news is this situation it’s avoidable.

We’ve written before on the importance of hiring process and interviewing but today I’m going to share with you the most common things hiring managers miss when they first begin their search.

What do I need?

There’s a really simple framework I like to use when I’m trying to answer a question such as, “Who do I need to hire?”

Ask "Why?" five times to short through what you think you need in an employee.

It’s called, “Ask Why? five times.” That’s it, literally all you need to do is ask yourself “why?” five times to get to a deeper truth. You can use this framework on any problem you’re trying to figure out but let’s use an example I saw recently -- a startup wanting to hire a Sr. Software Developer to work on their app. It goes like this:

I need to hire a Senior Software Developer.


Because we need more experience on the team.


Because we’re not hitting our product milestones.


Because the team keeps getting blocked.


I’m not sure.


I’m not a developer and I’m not sure how to evaluate what the team is telling me.

So now, by asking “Why? five times we’re starting to get closer to figuring out who to hire. We’ve learned the project is behind, the team is stuck, and the CEO isn’t really sure what the root problem is, i.e.: Is it a performance issue? A skills gap issue? Or a management issue? Or something else?

These are key questions for the CEO to answer in order to figure out what type of skill sets and personality to bring in.

For instance, if the team is underperforming because the project isn’t well planned, then the CEO might actually need a Product Manager rather than a Sr. Dev.

The point with asking “why?” five times is to be crystal clear on the problem you’re trying to solve when hiring. Let’s look at another example...

Grinder vs. Builder

There are lots of ways to classify work activity. Jobs can be “analytical” or “creative”, “repetitive” or “ambiguous” or some parts of all of the above.

One scale or dimension that’s important to be clear on, especially for early-stage companies hiring their first employees -- is what I like to call the Grinder -- Builder scale.

A Grinder is someone who loves working down a list of defined tasks and executing. A Builder is someone who likes to make something from nothing.

Startups hiring their first employees need people who are really good at doing both and are adept at switching between the two modes. Afterall, building a company in the early stages is equal parts figuring out what to do and how to do it, then grinding relentlessly to create momentum.

A common mistake startups make is underestimating just how much building an early employee must do. Let’s take a startup I worked with last year that wanted to hire their first sales person. First, we asked “why?” five times:

I want to hire a salesperson.


Because we need someone to do our sales process.


Because sales takes up too much time.


Because our process is manual.


Well, it’s the first thing we tried and it kind of worked so we haven’t really changed it.


We’re not sure what else to do.

While this startup was a team of brilliant technologists, sales for them was really just a means to an end. They did it because they had to, and overall it wasn’t going that well. Now they wanted to hire away the problem.

By thinking of the role in these terms, the CEO quickly realized that hiring someone just to grind away at their current sales process wasn’t going to really solve the problem. Instead, he needed someone with deep domain experience who liked putting sales processes in place at startups (building).

“Never hire someone who knows less than you do about what he’s hired to do.” Malcolm Forbes, Former Publisher of Forbes

This seems obvious but in practice startups often hire people they think can “figure it out” because they seem smart or look the part. Instead, they should be crystal clear on what needs to be built and find someone who has successfully done it before.

Intrinsic or Teachable

Naturally, when thinking about the people we should hire it’s easy to conflate qualities of temperament (intrinsic) with skill sets and work experiences (tachable).

For instance, I highly value intellectual honesty and curiosity in people I work with. These are temperament traits (intrinsic) and may or may not be important to doing a job. In fact, there are many jobs where these traits can be detrimental (i.e.: when a customer is wrong, you don’t necessarily want your customer success manager to engage in a high-minded discourse enumerating all the reasons the customer is wrong and debating them into submission. An agreeable person would be better at this job).

There are many things that we wrongly think of as intrinsic when in fact they’re teachable. Jeff Bezos wrote about this recently with regards to having high standards, which he argues is a teachable trait.

I agree with that and would add things like customer obsession and diving deep as teachable. Of course certain temperament traits may dispose some of us to being better or more natural at these things but it would be a mistake to think people can’t learn them.

So, when we’re thinking about who we need to hire and what they need to do, we should be asking ourselves a few key questions about our requirements.

  1. Is the requirement intrinsic or teachable?
  2. If it’s intrinsic, do we know how to assess for it?
  3. If it’s teachable, do we have the culture that will teach it?

The most successful companies are the ones that build the strongest, results-oriented cultures.

Hiring is sometimes like a game of Tetris.

These companies are diverse in style and methods -- often highly adapted to their industries and customers. But what they all have in common are enduring cultures that consistently generate value.

The odds of you building such a culture are highly correlated to your ability to hire great people from the very beginning.

Who you hire as your first employees will define your culture for years to come and in ways you probably can’t imagine.

For that reason, it’s worth it to put considerable thought and effort into your hiring process from the very beginning. Who you hire is largely in your control and probably the on of the single biggest factors in whether you’ll succeed.

Final thoughts

Hopefully some of these ideas are useful as you think about hiring your first employees. I have two last pieces of advice.

First, take your time. Breathe. I know there is tremendous pressure to hire, especially if you’re venture backed. But if you really want to increase your odds of success, spend a little extra time figuring out who you need and why, then putting in place a recruiting and hiring process to get them.

Second, get help! Ask your former managers. Ask your investors. Ask your peers. Get feedback from people who have done the job before. Talk to a reputable consultant or recruiter. Involve your co-founders. Bottom line is, don’t go it alone if you don’t have to.

I hope you found these ideas helpful. Don’t hesitate to reach out if we can ever help.

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