Your big hiring mistake

In 2014, I learned an expensive and painful lesson.

Ampush had scaled from 5 to 100+ people and was poised to be one of the largest advertisers on Facebook. We had just won an award in Facebook's innovation competition.

And what do fast-growing companies need? Executives!

Our first hire? A CRO — chief revenue officer. We landed a resume from an exec who worked at a company that scaled to billions in Google ad search. He was an industry leader.

We interviewed him. Asked lots of questions. He aced everything.

He had the industry experience we lacked and knew all the right words. We hired him at a million-dollar comp package!

Three months later, he walked into a company town hall to present his 2014 sales strategy and claimed his "computer crashed" and that he lost the whole presentation.

When I asked him to share what was in it, he crumbled. The following week, he resigned.

What did we do wrong? Everything.

Now, over 10 years later, my executive hiring skills are STILL barely 50/50. Executive hiring remains one of the hardest things I think founders do.

So while this won't be a master class today, hopefully I can share a few things that have worked for me.

I think I stole this from Marc Andreessen. The biggest risk to most founders is that they have NO reference point for what excellence in executive leadership actually looks like.

His advice: Reach out to 5-10 of the best people in the world at their jobs — not to hire them (you likely can’t), but to establish a benchmark for greatness.

Once you know the bar, hiring becomes much easier.

When I was looking for a great VP of engineering, I took this advice to heart. I spent 45 days pinging other adtech CEOs, asking to meet their VP of engineering.

What I learned blew me away. I thought great engineering leaders were technical coders and whip smart.

What I learned was that, while some of those things were maybe true, these people were actually amazing leaders, project managers and entrepreneurs.

It changed my entire approach.

Most skilled executives have decades of experience, which is probably at least 10+ more years than you have. This presents two challenges.

Because they are (probably) more experienced in the industry than you, they can say whatever and you won’t be sure if they are right or wrong.

Even more confounding, executives, by their nature, are great at TALKING, especially those in sales.

One thing we realized about the CRO above was that he had 2 talk tracks mastered.

When we interviewed him, everyone heard 1 of the 2. He sounded smart and varied. The second we got past those talk tracks, he was terrible.

Looking back, there were signs: How he responded to emails, the way he pushed back on completing an activity mid-process, what some of his referrals said… But we were wooed by his words.

Instead, focus on actions. Always include exercises in your hiring process that DEMONSTRATE capability rather than just DISCUSSING it.

One of the great VPs of engineering I spoke with made an offhand comment to me, "At this level, fit is far more important than skills."

I chafed. Remember, I was only a few years out of Wall Street.

I thought, “No way. I want fast-thinking, super smart, technical, etc.”

I was wrong.

Yes, skills matter. But 90% of execs who have held that role multiple times at multiple companies are going to be fine skills-wise.

FIT matters way more. At Gateway X, this is core to how I support my CEO partners in their executive hiring.

Rather than always saying, "This is the best person,” I think more along the lines of, “Who is the RIGHT fit for you?”

Kasey, Adriane and Andrew are totally different people, and their execs, therefore, need different temperaments, strengths, etc.

How do you assess fit?  Here are a few ways:

A) Be honest: Talk about yourself and your strengths/weaknesses very honestly; especially don't hide from your flaws. The right execs are there to complement you.

B) Spend more time on the "how" vs the "what:” I.e., not, “What would you do to grow our sales?" But, "How would you deal with missing your number?" WHAT is easy; HOW is not.

C) Spend a LOT of time together: I've found most people can fake it for 2-3 hours. But after that, the truth starts to show up. That's not a bad thing — you want to see the truth as soon as you can.

I always think of executives as mini CEOs. Ultimately, their power is in their ability to mobilize a group of people towards a goal in a fun and effective way.

Is this person a leader? The easiest question by far is, would YOU follow them?

All my best executives always became mentors… To ME! They would share advice, observations and feedback. I would work for THEM!

Other important leadership traits: People-first, empathetic, has vision, can fly at multiple levels and, of course, strong executive functions (i.e., organized, methodical).

And, of course, my favorite leadership trait…

If I haven't said it before, self-awareness is what I view as the most important trait for any person (and, thereby, any leader). Self-awareness is like Wolverine's auto-healing power.

If you have it, over time, almost any issue gets resolved by the person themself! It’s amazing.

On the contrary, when lacking, people get stuck in loops they never seem to pull out of, regardless of smarts or talent.

Related to this is responsibility — i.e., do they view themselves as the "creator" or "victim" to their situation.

I dig into this by asking about failures and challenges they've faced. Of course, if they say, "None and never," then they are either lying or not self-aware.

Once they share a challenge, I ask them how they co-created the situation. This is a great one because, almost immediately, you can watch someone react.

Do they get uncomfortable, are at a loss for words and then continue to blame the former employee? 

OR do they look calm and happy, and proceed to tell you, "I’ve thought a lot about that. Here are 3 ways…"

When I see self-awareness and responsibility, I get very excited!

Does this mean you will now be an executive hiring ninja? No. I think 50/50 is a good hit rate! And, to that end, one of my last pieces of advice: Build in an offramp.

It does no one any good if it’s obvious to one or both parties that there isn't a fit and you keep forcing it. The next best thing you can do is a fast separation.

Indeed, sometimes this is the only way to get "good" at executive hiring.

Have a great week!

-jesse