A Startup Hiring Philosophy

There’s a saying in venture that: “A-players hire A-players; B-players hire C-players.” Your ability to grow a business is often closely correlated with your ability to attract and acquire talent. But what does it mean to attract and hire world-class talent? Especially for functions you, as a founder, yourself may not be an expert in.

“A-players hire A-players;
B-players hire C-players.”

How does a first-time founder how to vet a seasoned sales executive? Or on the flip side, how does a non-technical founder learn to differentiate a good AI engineer from a great AI engineer?

While even the best founders, leaders, and managers make hiring mistakes, hopefully this post can act as a reference point as to what to look for. And while I have yet to master the craft, I’ll borrow 5 lessons from some of the best that has served as a guiding principle for me and for some of the founders I’ve worked with.

5 Lessons from 4 of the Greatest

  1. Hire passion; train skill.
  2. Desire/obsession > passion.
    • And, the ephemeral nature of passion.
  3. Hire VPs who can hire.
  4. Attract and hire intentionally.
    • On building trust.
    • On scaling yourself.
  5. To hire your best complements, ask people in your network 2 questions.
    • Who to ask? And what’s next?

1. Hire passion; train skill.

A few years back, I had the fortune of meeting one of the managing directors for a Fortune 500 corporate venture capital arm (CVC). And he told me something I thought was quite peculiar at the time. “Hire passion; train skill.”

Do understand that this doesn’t mean you’re hiring just anyone who’s really excited about you’re working on. This means hire someone who’s really excited about your product/market and has a baseline in skill, over someone who’s extremely skilled but couldn’t care less if you succeeded or failed. Ya, maybe upon success, that would mean the value of the equity they’re given means something. But that’s not who you want. Especially when you’re gonna go through hell or high water before you get there.

If you’re interested in learning what being in the
idea maze looks like, check out this post I wrote
last year.

Now there’s another nuance as to what “really excited” means. Simply put, they are obsessed about the problem space, not just passionate. They’ve spent time in the idea maze – where they may have reached similar and/or different conclusions compared to yours. And, the more detailed you can plot out how they reached their conclusions the better. And while you don’t have to agree with their conclusion,

  1. Be open-minded enough to entertain new perspectives.
  2. You might learn something in the process. And that means you don’t have to make as many mistakes to reach your goals as you might have needed to before.
  3. Hire people who think on different wavelengths to bring diversity of thought into your team.

2. Desire/obsession > passion.

As Thomas Keller, holder of 7 Michelin stars, puts it in his 2010 TED Talk:

“When I ask a young culinarian, ‘why do you wanna work here? Why do you wanna cook?’

” ‘Oh, Chef, man, I can’t tell you how passionate I am about what I do.’

“I go: ‘Okay, that’s interesting. Passion.’ I’m passionate as well. I’m passionate about the first asparagus I see. The first baby spring lamb that comes in the back door. I’m really passionate about that. But after a week or two, what happens? My passion, kinda, subsides. It goes down a little bit because I’ve already seen it. I’ve been experiencing it for a couple of weeks. I’m kinda over it a little bit. But I still have amazing asparagus. It’s still coming in the back door. I still have amazing spring lamb. What is it that’s important to me in recognizing that individual that he should be working at our restaurant? Or what is it in me that continues to drive me?

“It’s desire. Desire… Desire trumps passion every time. It’s nice to be passionate, and passion is going to help move that desire higher. But when that passion is not there, what do you need? That desire. That strong sense of desire.”

The ephemeral nature of passion

According to him, passion is fleeting – ephemeral. Desire, or what I call obsession, isn’t. Whereas passion is what keeps you alive in phases and sprints during the day, obsession is what keeps you up burning the midnight oil. Whereas passion is pursuing what you love, obsession is resolving what you hate. A desire to prove something or to someone. An obsession to conquer the seemingly unconquerable.

People who are obsessed have something to prove. Because of that, they learn fast. So fast that what they didn’t know how to do last week, they can do today. And what they can do today, they become your team’s expert in, next month.

“What is your selfish motivation?”

One of the alumni of the college organization I was a part of, who went on to become a senior leader at an NLP startup (later acquired), puts it best: “What is your selfish motivation?” When you’re in your darkest moments, what’s going to keep you going? What’s going to drive you irrationally forward?

For that, you’d need desire. Not just passion.

3. Hire VPs who can hire.

It may seem obvious when I put it like that. But when you’re in the thick of it, you tend to forget. And if so, you wouldn’t be alone. Even anecdotally I’ve chatted with many founders who don’t prioritize their VP hires by their ability to scale a team. Yes, you want them to have a track record for:

  • Managing teams,
  • Hitting milestones/quotas,
  • Leading initiatives,
  • Winning deals,
  • Building efficient and productive internal systems,
  • Building trust,
  • And being a culture fit for your startup.

But if you’re looking to scale, you want a team that can scale as well. As Jason Lemkin of Saastr, one of the greatest minds in the SaaS space, puts it in a Saastr blog post:

“This is job #1 for all your VPs. Recruiting.

“You’ll feel the pain fastest with a VP of Sales that can’t hire, because they’ll miss their number quickly. The impact for a VP of Product that can’t hire will be more delayed, it may take 6+ months, and several releases, to fully manifest itself. A VP of Marketing that can’t hire will hire terrible people — but it may take you a while to see it if they aren’t judged quantitatively. So the tangible effects of a VP That Can’t Hire may take you from 45-180 days to see, based on position.

“But it will wreck you as you scale. Yes, maybe you can backfill a few hires. But not all of them.”

How do you know if your potential VP hires are good at recruiting?

Lemkin says: “Check who they hired.  Not inherited as a manager.  But hired themselves.  And make sure they hired at least 2 good folks.  And ask to talk to both of those 2 great hires.” What you’re looking for in the conversations with their 2 great hires are:

  1. What results did they accomplish?
  2. What kind of feedback and discourse did they have with your potential VP hire?

If you do end up hiring a VP who can’t hire, he suggests “top these VPs that can’t hire fast.” Hire a VP who can, on top of them.

4. Attract and hire intentionally.

This point is more or less of an add-on to what I mentioned in this post. It’s important to set culture from day 1, and dare I say, a shocking one as well. Your goal is to have candidates effectively self-select themselves in and out of your funnel. Why? Just as your cultural values aren’t unique and differentiated, your (potential) hires won’t be either. And it also means it’s harder to find folks who are truly obsessed about what you’re building.

On building trust

At the same time, keep in mind how restrictive your values may be as you scale. While it is useful to be strict early, requiring all employees to wear flannel with misaligned polka-dotted buttons every day will make it hard to scale your team. From the lessons of Carly Guthrie, who ran HR for Per Se, one of Thomas Keller and New York’s hottest restaurants, and at multiple startups:

  1. Trust your employees. And make sure your managers trust their team members, as well. Trust in the process of how and why you hired them.
  2. Deeply respect your employees’ time outside of work. This may be easier said than done for many founders, especially those who hold themselves to a high working standard.
  3. Foster a community of trust and care. “The hallmark of a healthy culture is that people feel comfortable bringing up problems with and offering feedback to their leaders and vice versa.”
  4. Let mentorship happen organically. You don’t have to force, but let your team know that the option is always open.

As you scale, hire world-class HR people who can build upon the above. As Guthrie puts it, “hire or contract someone who has the ability to tell you hard things you don’t necessarily want to hear — someone you can trust to give you a good reality check when you need it.” And your friends in HR may help to serve this purpose. At the same time, as vital as it is to trust your talent, trust the system you build.

On scaling yourself

With every hire before employee #20, the question you’re trying to answer is: “Can this hire help me check off at least 1, maybe 2, of my top 5 priorities in the next 6 months?” Or in a different light, “Can this hire help me get to at least 1 of my top 5 milestones this year, at least twice as fast?”

5. To hire your best complements, ask people in your network 2 questions.

While I hope you are building technical and non-technical literacy in the process of building a business, sometimes it’s hard to understand an industry/job function in 1-2 years, compared to someone who’s spent 10 in it. These days, there is also plenty of literature online – in the form of Substack newsletters, blogs, industry reports, YouTube videos, etc. All of which can help compensate for mistakes you may have had to make in the future.

So, I’ll tell you my little hack for building a repertoire of knowledge.

  1. Google top 10 blogs for X industry. Subscribe to all of them.
  2. Find the top 10 thought leaders in the space. See if they have content online. Reach out to them. Here’s a “template” for cold emails to help out.
  3. Then, ask the people in your network who you think are subject-matter experts (SMEs), or -subject-literate people who have a network that include SMEs for what you’re looking for. Ask them:
    • “Who are the 2 people in your network that you would go to, to solve [blank] problem?”
    • “And, who are the 2 people outside your network you would go to if you could?”

And you guessed it. Do your homework. Then try to get in touch with them.

Who to ask? And what’s next?

For the subsequent referrals, if you (a) know them well, (b) know you and your business well, and (c) are reasonably sure that they know the person you want an intro to well, then ask for an intro. If not, I would default on sending a stellar cold email/message to the relevant party yourself. Also, the reason I have the nuance of “subject-literate people who have a network that include SMEs” earlier is that there’s no point in asking folks who don’t understand the function/industry you’re asking about. It’s like going to a sushi buffet and asking the cook what hamburger they would recommend.

And do step 3 again and again, until you find when skill meets obsession about your problem space. As you pick a few candidates in your funnel, ask those same SMEs to help you with technical diligence on the candidates’ experience and skill level. Whether you have the respective literacy or not, it’s always smart to have others you trust check your blind side and offer a second opinion. So, you can make the most informed decision.

In closing

In all honesty, there’s no one rubric for hiring world-class talent to your startup. Everyone has a different practice, and different practices work in different scenarios and for different businesses. For instance, the way you hire for a consumer social business is different from a deep tech venture. There’s probably a lot less PhDs in blockchain technology than MBA product managers. Subsequently, different industries will have different benchmarks for what an expert entails. Some markets have been around less than 5 years, whereas others have been around for decades.

But I believe these 5 lessons are the common thread in most early-stage talent acquisition practices. When you’re hiring your first engineer. Or your first product manager. Or your first senior executive.

Some more thoughts on scale:

  1. If you’re curious about another perspective on scale, including hiring, culture, product, operations and growth
  2. Why it’s important that every team member can work well with every other team member

Photo by Jacek Dylag on Unsplash


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