Find Your People
Or why building a great team starts with knowing who you want
The Next Founder helps founders build great startups. We offer advice on managing your mental health and productivity, hiring and managing great people, building a strong culture, and keeping people aligned and working on the right things. See the series overview at Welcome to The Next Founder and find out more about me at My Story.
“I noticed that the dynamic range between what an average person could accomplish and what the best person could accomplish was 50 or 100 to 1. Given that, you’re well advised to go after the cream of the cream. A small team of A+ players can run circles around a giant team of B and C players.”
— Steve Jobs
“I constantly see people rise in life who are not the smartest, sometimes not even the most diligent, but they are learning machines. They go to bed every night a little wiser than when they got up, and boy does that help.”
— Charles Munger, 2007 USC Law School commencement address
“If he’s such a good hitter, why doesn’t he hit good?”
— Billy Bean, Moneyball, (Aaron Sorkin Screenplay)
A Tale of Two Bosses
You hired Angie and Bonnie as Directors of Marketing and Operations last month. They started at 9 am on a Monday, and by noon their paths had diverged. Now, four weeks later, they are in different zip codes.
Today’s staff meeting drives the point home. Bonnie presents an improved operating plan that shows she has completely digested your startup’s market, culture, and strategy. She introduces three new team members she hired, each of whom seems so talented they could do Bonnie’s job.
Angie’s update reveals she’s circling the drain. Marketing didn’t accomplish any of its goals this month, which isn’t surprising since she barely remembers those goals. She still can’t articulate what customers you sell to or why they buy from you. She presents the resumes of two people she wants to hire, each a junior clone of herself. You ask to hold off since it’s unfair to hire people you’ll have to let go right after you let their boss go, which you’ll do by the end of this week.
In the spirit of learning, you ask yourself why Angie and Bonnie turned out so differently.
You start with their resumes. Angie’s was actually more impressive. She did the same job at a well-known larger tech company, where Bonnie came from a failed startup you had never heard of. But it’s Bonnie who is firmly in control of her team, while none of what Angie learned at the BigCo has helped her at your startup.
You consider their experience in your market. Angie’s last company sold into the same industry you sell to, and you expected she’d leverage her knowledge and contacts. Bonnie’s company sold similar-sized deals but in a different vertical. Yet, Bonnie is building connections with your customers daily, while Angie burned through her handful of tentative contacts in her first week and hasn’t developed new ones.
You read the interview notes. Angie was smooth, polished, and professional. Someone commented she was like an actor playing a corporate executive in a Netflix series. Bonnie was a clear communicator but came across as geeky and introverted. She didn’t seem interested in small talk and dove down quickly into her recent projects and the teams she built to do them. But now everyone is confused about what Angie’s team is doing but blown away by what Bonnie’s team has delivered.
You are flummoxed. If you had to bet on Angie versus Bonnie when you interviewed them, you would have doubled down on Angie, but she’s the one who will be gone after the awkward 5-minute firing you have scheduled for Friday afternoon.
How can you hire more Bonnies and fewer Angies? You have to Find Your People.
“On paper” versus “on the ground”
Every product your startup builds will be built by a person. Every customer will be sold to and supported by a person. Every marketing campaign will be driven by a person. Every strategy, plan, and decision will be made by a person. Every one of those people will be hired by another person. And you can only build a big company if you beat your competitors, who are all merely collections of people.
This is not the first time you’ve heard that building your team is one of the hardest but most important things you’ll do, but when you think about building your team, you probably lose sleep over how to source candidates, interview them, check references, negotiate compensation, and convince them to join your company. These are all important, and we’ll cover them in future essays.
But one of the trickiest parts of hiring might seem to be the simplest: deciding who you want to hire in the first place.
Every search starts and ends with a job description. That job description will attract specific candidates and repel others. You'll evaluate candidates against that job description. It will drive what they work on and whether they are doing a good job. It will drive how much you will spend on each position.
Yet most job descriptions are fired off without a lot of thought, often cloned from the horrible boilerplate job descriptions that big company HR departments cut and paste onto job boards. These job descriptions often have a long list of required credentials and experiences but manage to tell the applicant almost nothing about the company or the team they’d be working with. You might want to put a little more effort into yours for a few reasons:
You are a high-growth startup
More people have worked at medium and large companies than at startups, so many people who apply for jobs at your startup will come from larger companies with established brands, large customer bases, and playbooks for their primary business functions. A high-growth startup builds those things from scratch, which demands different skill sets and, more importantly, different attitudes and expectations.
You are doing something new
Any startup worth starting is building a product that has never existed before and often is tackling a new market. You can’t hire someone who has done precisely what you are doing since no one has. You might find people who have solved similar problems for similar customers, but you are hiring people to help you figure out your business, not replicate what they did at their last one.
You have a small team
Your startup has to research, design, build, and deliver your product. It has to attract prospects, turn them into customers, and make them successful. It needs to hire people, pay them, and fund the company. It does all this with a tiny team — even a startup with only a few people has to cover every one of these functions, so anyone working at a startup will have to cover more ground than at a larger company. They have to be willing to jump in and do jobs they’ve never done and where they have no experience or training.
Your startup will change
A large company can hire people into jobs that won’t change much, but roles at startups change constantly as the startup pivots its product and experiments with different strategies to attract and keep customers. A startup often hires someone to do a job that doesn’t exist in the same form in a few months, and startups often promote their team members since they grow so quickly.
You can’t pay as much
Most startups are racing the clock to keep from running out of money before they make enough progress to raise more or get profitable. You have to find people willing to sacrifice some cash for stock options and are looking for the learning and career acceleration a startup can provide.
These differences mean you have to put a great deal of thought into what kind of people you need to succeed, how you’ll attract them, and how you’ll evaluate them. No two startups are identical, but as you build your team, you can think about a few things:
Don’t “hire by keyword”
You know the work that needs to be done at your startup, so you’ll be tempted to look for people who did that exact work at their previous gig. If you are building machine learning pipelines in Python, you might write a job description requiring 5 years of experience building machine learning pipelines in Python. If you sell CRM software to financial services companies, you might only consider sales reps who have sold CRM software to financial services companies.
Looking for people who have already done the same job can work, but asking someone to cut and paste their last job often backfires for a few reasons.
First, you aren’t a Google or an OpenAI, where thousands of applicants will respond to each of your job postings. You have to expand the pool of candidates you can go after, and every time you add a “must-have” qualification, you drain the pool. I’ve seen startups write job descriptions with so many “must-have requirements” that almost no one applies.
And you are building a new product and using new technology to build it. When you’re on the bleeding edge, you won’t find many people with years of experience in the relevant technology stack. Reddit is full of threads mocking job descriptions written by HR departments demanding “5 years experience” working with technology invented 12 months ago.
Should you at least find people who have sold into your industry? It can be helpful, but when you make industry experience a requirement, not only do you limit the pool of people you can recruit, you might find that experience isn’t very helpful anyway. Airbnb is full of people who have never worked in hospitality, including the founders. Netflix was not startup by anyone had worked in Hollywood. Many of my worst hiring mistakes happened when I got enamored by candidates with experience in the industries we were trying to crack. Many of them couldn’t adjust to a new approach to their industry, and they didn’t last long.
Don’t write a “unicorn job description” where, if taken literally, the Venn diagram of people who could check every box would yield almost no one.
Be open to people who have worked with adjacent technologies and markets and who have the desire and ability to learn your business quickly. That profile describes the founders and early teams of many successful startups.
Hire for the future
Some founders assume that hiring is like reading applications for an elite college, where you look at a candidate’s qualifications and achievements and pick whoever has the most impressive list. But a credential happened in the past and is only helpful if it predicts what the candidate will do in the future when they work for you.
You might think you should look for people who have already done the job you are hiring them to do, but that filters out many of the best candidates. Ambitious people want to learn and grow, not spend the next five years doing the exact job they did for the last five years. They won’t join if you ask them to.
Look for people on the upward trajectory of their careers who might be doing the job for the first time. If you are hiring a VP of Marketing, your best candidate might be a Director of Marketing who was second in command working for a great VP at another startup. They might join you because you give them a chance to do the larger role for the first time, and they’ll tackle the job with energy and enthusiasm, seeing it as an opportunity to make their mark.
Look for “learning machines”
Experience is important, but anyone joining your company will have a steep learning curve regardless since your business is new and unique and will continue to morph and pivot as your market changes and as you learn how to win that market. Find people who love to learn and know how to.
Great learners don’t usually have elite educations. Sure, someone who went to Stanford probably has some brainpower (unless their parents donated a building), but for every elite college grad, dozens of others went to less prestigious schools (or no school at all) and can learn just as quickly. You can also hire them without competing with the thousands of other companies who target prestigious degrees, especially since that degree might come with a level of entitlement that makes them a poor fit for a startup anyway.1
At one of my companies, we built our backend systems using the Go programming language, but we didn’t list Go as a requirement in our job descriptions. We would have cut our candidate pool by 95% and excluded many amazing candidates. The kind of people we hired would be smart enough to pick it up quickly anyway. Some even joined us because we offered them the opportunity to learn something new.
Hire for your stage
Most founders want to build a big company and are told they need to “learn to scale.” Some assume that scaling means hiring people from already-scaled companies, like Salesforce or Google. Hiring those people can work, but it can easily backfire.
Just because someone works at a big company doesn’t mean they know how to build a big company, any more than driving a car means you know how to build a car. Many BigCo people sell mature products into established markets using playbooks that someone else wrote years ago. You and your team are building your product, defining your market, and figuring out what works and what doesn’t. You want people willing to sign up for that rollercoaster and not get frustrated by constantly shifting projects and priorities.
Also, many positions at large companies are narrower and more specialized. They have enough people to slice responsibilities thinly. An early-stage startup only has a handful of people, each of whom has to cover more ground.
Many of your best candidates will come from other rapidly growing startups. Some might come from failed startups, where they learned some things not to do and are eager to do better the next time. They know what to expect at a startup and have probably picked up the skills and resilience needed to thrive in day-to-day startup life, where every day is different, and pivots and course corrections are constant.
Make it personal
We have talked about hiring people who are ambitious, want to learn, embrace change, and know that sacrifice is needed to build a great startup. Are we talking about culture?
We’re starting to. Culture is a big topic and will be the subject of future essays, but you need a sense of what kind of culture you want to build because, spoiler alert, that culture is a mashup of the founders and the people you hire. Your culture attracts the right people, and you build that culture by hiring those people.
Hiring for “cultural fit” has gotten a bad reputation, and, yes, it can backfire. No, don’t only hire people the same age, gender, nationality, and personality as you, or your startup’s diversity and creativity will suffer. Don’t only hire people who approach problems like you do and won’t challenge each other. But have a point of view about the kind of people you want, and don’t be afraid to go after that.
Expose your culture at every touchpoint of the recruiting process, starting with your job descriptions and the recruiting section on your website. Share why you are excited about your startup, and be explicit about the kind of people you want to bring on the journey. Don’t be afraid to repel the people you don’t want. The very definition of culture is that it attracts some people and not others. Let your personality shine through and make your content conversational and friendly. There are no HR gods in the sky who will crack down on your company because your job descriptions aren’t written like the ones down at the DMV.
At this point, you might be wondering, once you know who you want, how do you find them, get them interested, evaluate them, and get them to work for you? We’ll start answering those questions next in “Build a Talent Magnet.” (Coming soon)