13 Lessons on Hiring the Right People from Founders and Investors

Lately, as I’ve been prepping to launch my new venture I’ve had the pleasure of speaking to a lot of people about hiring best practices and I wanted to share some of the most useful tidbits from the hundreds of conversations over the last few months:

  1. Once you give a candidate an offer, always put an expiration date on it and go out of your way to get them excited about the opportunity. Get multiple people from the team (even investors if possible) to make them feel special.
  2. I usually tell founders before hiring someone for a specific task perform the task yourself for a period of time so you’re familiar with the challenges and have a better idea who would be the ideal candidate.

Andres Blank, CEO and Co-Founder of Scout


The best hiring advice I’ve received AND would give to anyone else is to first and foremost TRUST YOUR GUT, and to develop a couple small “test tasks” that will give you an idea of the candidate’s communication style. Not everyone communicates in the same exact way which is fine, but especially in all-hands startup mode, making sure styles are at least in line with the company and team will cut down on a lot of headaches that could otherwise be avoided by clear communication!

Erin Elizabeth Finnegan, CEO and Founder of PuppySnob


My wisdom is to spend MORE time on reference checking than on interviewing the person. That’s the only half decent way to know what someone’s strengths and weaknesses will actually be!

— Jessica Mah, CEO and Founder of InDinero


My favorite question to ask is “Are you the type of person who asks permission or forgiveness?” It sheds light on the person. Also, the first thing I do to research a person is check instagram vs. LinkedIn. Sometimes I don’t even make it to their credentials on LinkedIn because I can already tell if they’re likely to be a culture clash.


  1. It’s best to hire generalists early on in your company trajectory. In the early stages, roles tend to be more fluid and require a breadth of abilities. As your company matures and you have a better sense of company direction, shift your focus to hiring specialists.
  2. Even when hiring for a generic role like a Software Engineer or Customer Success Manager, first identify the key focus areas where your existing team lacks experience or skill set. Be sure that the person you are hiring fills at least one of those gaps. This will invariably be beneficial at a later stage as your company grows.

Raj Sathyamurthi, CTO and Co-Founder of AirPR


The standard hiring process is a quick process with a few controlled candidate interactions, but it really takes time to get to know someone. You likely wouldn’t commit to someone romantically after one or two dates, but that’s often how many times you meet someone before you hire them and commit to them professionally. Take the time to really learn about this person. How do they think? How do they work with others? How do they react in stressful situations?

Maggie Hsu, Advisor at Zappos.com


  1. One of the biggest mistakes executives (particularly founders) make about hiring is starting the process too late. There’s always to be pressing time items that you think you need to do right now — but recruiting is one of them. You should spending at least a few hours a week thinking about your people… where there’re gaps, where there’s upskill / training potential, and where there’s misalignment.
  2. An important part of the hiring process that a lot of people miss is creating consensus on the ideal candidate (or creating a candidate “scorecard”) before you begin the recruiting process. It allows the recruiter (internal or external) to bring you better candidates, and it helps all the interview committee speak the same language, while discouraging implicit bias.

Stephanie Gantos, VP of Finance + Operations at Degreed


Before you fall in love with a candidate do reference checks … really detailed reference checks including both front door and back door references.

The single biggest mistake I’ve made, and I’ve seen others make, is that they go through a massive hiring process talking to many different candidates — finally finding one everyone clicks with — and at that point either out of fear, laziness, misplaced self-confidence or some other mashup of Munger’s biases (http://25cognitivebiases.com/) they fail to do *thorough* reference checks.

Even after the best process, people who have worked with the candidate in the past will have a better sense of them than you and the team do. Hiring isn’t an exact science and you will make mistakes.

Brad Gillespie, VC at IA Ventures


One of the first questions I ask any would be employee is “What does your perfect workday look like?

It tells allot about them if they don’t know.

Secondly I ideally look to have CV’s and cover letters sanitized of any and all names, gender or race identifiers before I review candidates and always look to keep job descriptions short.

Benji Rogers, CEO and Co-Founder of dotBlockChain Media


Solve the problem of freeing up the startup’s single most valuable resource — your time. Many founders will look for a head of sales before they’ll hire a virtual admin to handle minutia. That seems silly: your time is more valuable to the company than anyone else’s, so you should free it up in the least expensive way possible.

It’s hard to assess a skill you’ve never practiced (it’s like getting a specialist doctor, you pretty much have no choice but to trust the referrals of others).

Roy Bahat, Head of Bloomberg Beta


  1. Hire for aptitude and curiosity instead of experience. Experience is misleading, and will often get you someone who does something ‘their way’ and no other way. Most startup gigs require more ‘figuring out’ than executing, and taking on a slightly junior but hungry person will bring you a talent that will grow with your company.
  2. Don’t make yourself the smartest person in the room by hiring people worse than you.
  3. Make sure you set up new hires for success. Few things are worse than setting a good person up for failure because the company or the product wasn’t ready for them.

Vik Venkatraman, Bionic Entrepreneur, Co-Founder of Clothes Horse (now part of Rakuten)


Most managers screen on skills and experience in the recruiting process. I’ve found skills and experience are quickly and easily assessed but not predictive of how successful someone is going to be in a role. More often than not it is someone’s attitudes and behaviors that predict success and these can be assessed in the interview process but usually aren’t. With the right approach you can eliminate a lot of “bad hires.” The book “Hiring for Attitude” has a good approach for how to do this.

Bill Trenchard, Partner at FirstRound Capital


Once someone is excited to join one of the companies I’ve started and we’re excited about having them join, I sit down with them and tell them all the reasons not to join. I share all of the things I can think of that can go wrong. If they’re still excited then, they’re the right person for the job. If they’re not, than in spite of all the talent we saw in them, they aren’t right for us.

Andrew Weinreich, Entrepreneur, Investor and Podcast Host:


So there it is! If these quotes make you rethink your own hiring systems, please check out IN|DE and check out our Recruiting Ecosystem Audits—so you can ensure that your company’s hiring process is optimized for getting the best people into the right roles.