The Genius of Woo

How to 100% sure you hire the right executive

Consider this — We date someone for years before we marry them only to spend an average of 4 waking hours per day with them. Yet, we interview for only a week to choose a company where we will spend 12 or more waking hours per day.

That’s nuts.

It seems absurd to me that we hire in this manner. In a startup even one bad seed can severely rock the boat. And as you scale up, hiring the exact right leadership can dramatically impact the entire future of the company. Yet, the entire ecosystem of recruiters, human resource professionals, and hiring managers simply give a collective “Well, that’s the way we’ve always done it.” excuse for what is so clearly an absurd practice.

So, I got to thinking. Can this be changed?

Specifically I was thinking about hiring executives. One of the things that sends me to take a cry shower the most is thinking about hiring senior management. Being a founder and scaling is about wisely delegating without abdicating and nothing puts this to the test more than hiring someone who is about to take ownership over something you hold dear. It could be product, engineering, design, or sales — but it doesn’t matter which it is because the only voice in my head is saying “If I hire the wrong person in the role, I could sink the ship”

“Worse, I could hurt my baby!”

But the problem is that executive recruiters, venture capitalists, and all of my advisors tell me the same thing. You can’t “try-before-you-buy” an executive. They’ll simply walk. All of my advisors said you simply need to find a way to make it work within the system that exists. “Choose your battles wisely they said. Invent on product, invent on technology, but why invent on hiring?” It’s just too much all at once and increases the risk too high. Plus, everyone else does it this way, why can’t I? And lastly, my favorite, “It’s already competitive as Hell, so why make it harder to hire. We should be making it easier!”

But I think we should raise the bar, not lower it.

I have this saying that when hiring, there’s “YES!” and then there’s everything else. The idea is that “YES!” is a definitive OMG I need to work with this person immediately. I love them, and when I think about them coming into the office, I get super excited. But the really important part is that there’s no such thing as “NO!” The reason is that nearly everyone has some good qualities. What the saying helps me to do is to eliminate the possibility of me negotiating with myself. It helps me NOT bring someone in who’s not perfect.

But can you really get to an accurate “Yes!” with just an interview?

The answer is no. I did this exercise where I looked back at all of the executives I hired in the past 10 years and I asked myself “how many of them were truly ‘Yes!’ versus honestly ‘everything else.’” The answer scared me to death. The majority, the vast majority, were people that if you pointed a gun at me, I’d have to admit were “everything else-ers.” They were people that were ok, but not great. People that would pass any interview as a “Yes!”, were good enough for now, but in my heart I knew they were really a “Meh…”

Sound familiar?

So I decided to talk to other founders, other people who hire executives, and low and behold I found pretty much the same thing, plus a harsh reality. All of these people said kind of the same thing: “if I’m publicly asked then I’ll tell you these people were brilliant and I’m even more brilliant for hiring people smarter than me.” but in private I’ll tell you that in reality all of these people weren’t me. They where here to take the company to the next level and those who didn’t, simply got cut. It was a numbers game — hire a team, those who scale stay, those who meh… die.

I didn’t want to build my company this way.

There’s a ton of reasons why this pattern of hiring, firing, and growth was something I thought could use some improvement. So I listed out all of the problems caused by this type of growth.

• The moral hit of hiring and then exiting a leader is tough on the team.
• The confidence hit from the board, the press, and the public reduces optionality for a CEO.
• A rotating door of executives may seem like it’s something you can get used to as a CEO, but it’s more difficult than you’d imagine. No matter how you play it on the outside, when one of your team members fails, you feel the failure on yourself as well. Accumulate years of plowing through people and it weighs on you.
• It just feels inhuman to hire this way. I want to know my executives, to trust them, and to be in for the long haul.

In the end, I think interviews aren’t enough. The best way to interview someone, is to actually work with them.

So the first thing I did was assess how long it took me work with these past executives and get to know them — functionally this is “work” dating. After several interviews my gut felt at most 50% sure, but after working with someone for a week, I felt my confidence could go to 75% and at two weeks was at 90%. I wondered how could create a construct where I could work the equivalent of two weeks (roughly 120 hours) with someone. If I could do this I knew that my confidence rate and my success rate would be unlocked.

So I experimented.

Here’s how it started. It was at a time that I needed to hire a VP of Sales— the exact type of executive role where I thought “interviews” where bullshit. I then said to myself, “ok, assuming they are in for a joint woo’ing what would I want to know about them that cannot be tested in an interview.

Here was my list of questions.

• Could they supercharge our warm intros to perspective customers
• Do they really know the industry and can they amplify me
• Do they really have empathy for my customers
• Do they really have empathy for my team
• Are they a deal closer. i.e. how well do they think on their feet
• Can they amplify my sales team to be super closers
• Are they a strategic mind, i.e. how well can they think ahead
• Can they lead, i.e. could they earn the respect of the team they would be leading
• Can they hire, i.e. can they scale my team

Then I created the construct of the Woo

The key to dating in real life is that it is mutually beneficial. When we start dating we want to be attracted to the person, to their mind, and to their heart. But we also want to know if they are a serial murderer too. So when it comes to the woo’ing of an executive, the key is to make it mutually beneficial.

So here’s what I did.

I created a legal advisory board and called it the Product Council. I then sought out candidates through a recruiting firm paying them a cash bonus to add people to this Product Council. For those that joined the Product Council, I asked them to do several things to help answer my key questions that I listed above.

• Thing 1 — introduce me to 10 warm leads at the CMO level
  (can they supercharge warm intros?)
• Thing 2 — work with me to close those deals
  (are they a closer, empathy for my team?)
• Thing 3 — work with me to close 3 deals that I already have going
  (work with my team, empathy for my team?)
• Thing 4 — help mentor a sales rep that needs help
  (lead my team, empathy for my team?)
• Thing 5 — work with my ringer individual contributor
  (earn my teams’ respect?)
• Thing 6 — help me interview a candidate
  (can they hire?)
• Thing 7 — introduce 3 sales candidates
  (can they scale, empathy for my team?)
• Thing 8 — teach me about an industry
  (empathy for my customers?)

Then in return, I gave them a small options package which would be netted out of their total options package should they join. The options package was structured as a 12 month vest with 1 month cliff. Then I asked for the introductions in the first two weeks. If 50% of the introductions turned into meetings within the first month, I kept them. If they didn’t, I would let them know it probably wasn’t a fit for them to be on the product council, but I did my best to maintain a bridge.

Sounds brutal right? Sounds like something no one would accept right?

But you’d be wrong. The answer lies in human nature. Raise the bar, and I mean significantly rise the bar, to be hired, and you will be a beacon that calls out to the best. “A” players will respect you for creating a system that guarantees the bullshitters are caught and dismissed — and that’s because true “A” players only want to work with other “A” players. It’s a weird bit of math, but it turns out the harder you make it to be hired, the more people show up.

The result for me has been a true unlock .

Today, I now have 10 Product Council members all of which are productively introducing me to CMOs at the biggest brands in the world. We are now meeting as many as 10 CMOs per week and I’ve now expanded the Product Council to have similar programs to help me find my Head of Customer Success, My Head of Customer Strategy, and my Head of Marketing. On average it takes about 3–4 months of being on the Product Council to equal 120 hours of working together. But for each person that gets through the process, it’s been a godsend.

So how did people respond to the idea of woo’ing via the Product Council?

• 90% we invited to this new process thought it was a spectacular idea and saw it as a welcome and needed change. 10% ran for the hills.
• Those that had a job already saw it as a great way to get to know a new company and saw it as a net positive to get experience on a product council.
• Those that worked for larger companies were the most likely to like the idea because they saw it as an excellent way of de-risking the assessment of joining a younger company.
• Those that worked for a small startup were the most likely to NOT like the product council.
• Those that didn’t have a job, saw it as a great way get involved without needing to fully commit.
• Of these people, about 50% were a match to move forward,
• Of those 50% got approval from their company to join our advisory board. Note: we always made sure their existing company approved them joining our Product Council and that they were never asked to introduce us internally at the company that they worked for.
• Those that worked for entrenched incumbents were the most likely to love the idea and the least likely to get approval.

Of the people that ultimately joined the Product Council, 50% ended up as total bullshitters. And that’s the magic right there. It turned out that 50% of the people were simply talking a big game, had the logos, and the pedigree, but didn’t have deep trusted relationships in the industry, weren’t true leaders, and never gained the respect of the team. It turned out that asking them to do the job of VP of Sales, even in a minor way, was hugely enlightening. For those people, we simply dismissed them. No harm, no foul, no stock or even any money lost.

Even with these people we did our best to treat them like gold though.

Of the people that joined the Product Council and were the real deal, 75% ended up either not having the right passion match, the right like-mindedness, or were in the process of making a big change in their life.

Again, magic.

All of these people, and I mean all of them, would have been hired in an interview project. It wasn’t until I had worked the full 120 hours that I realized these things in these candidates. For these people, we gladly paid them their options and maintained the relationships. These are now some of most valuable advisors, critics, and truth-tellers.

And that leaves us with 5% of pure gold.

Which would be the 25% of the 50% of the 50% of the 90% that are the actual candidates for the role of VP of Sales. What’s amazing is that the normal process for hiring a VP of Sales is 3–6 months. But this process, the one that everyone said couldn’t be done, even shouldn’t be done, took me 3 months to get into gear and 6 to get where I am now. So for the same time, less money, and while creating a larger diaspora of people who love my company, I have changed my confidence level when I hire a key executive from 50% to 90%, maybe even 100%.

We now have an internal person in charge of tending the garden of the product council — it’s my Chief of Staff and her primary KPIs deal with the product council.

The candidates that become pure gold are the people that would walk through fire for me and I would take a bullet for them. These are the people that will amplify the highest of highs and be there in the lowest of the lows. These are my partners, my trusted compatriots, and who share every bit of the same crazy passion that I do. And the best part is that the ultimate test for knowing when it’s the right person suddenly becomes very similar to knowing when the person your dating is the right one for life.

It’s just easy.