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Kevin Ryan’s Tips for Hiring and Firing

Every month, we host a CEO breakfast for our founders and we recently had the pleasure of hosting Kevin Ryan. Kevin has an incredible track record of success, co-founding six companies (DoubleClick, Gilt, MongoDB, Zola, Kontor and Business Insider).

Here are takeways from Kevin’s tips on hiring and firing:


As a founder, you’d be smart to pay attention to who and how you’re hiring.

In the early days of building your company there’s a ton to focus on, but one of the most important lessons we learned at breakfast with Kevin is that a founder’s involvement in hiring early on makes a significant difference in the company’s culture and retention down the road.

What to Look For In Early Hires: People are expecting to grow and be promoted up through your company when they are hired, so you should look for candidates who you believe will be be doing amazing things in 10-15 years. If you play your cards right, they’ll be doing those amazing things still working at your company.

Red Flags: If someone comes to you having held 3 Director roles, chances are they won’t be great at what they do (otherwise they likely would have been in a VP role by now). Consider if you were to hire a Manager for the same Director position, chances are that person would be thrilled for the opportunity, feel optimistic for advancement, and potentially work harder. It’s not easy, but it’s important to try and find those underdog hires.

Keep In Mind: Your manager is desperate to hire someone because not having that person is a pain point for them.  At times you may need to flex on your hiring standards, but it’s your job as the founder (while you’re small) to maintain the quality of the team members you bring on. “You should feel great about every person on your team.”


References trump interviews.

Interviews are a test of how a candidate can interview, not of their skills or their style of work. Kevin suggests that reference checks are the key to understanding whether a person is, in fact, good at the work that they do.

How to Conduct a Reference Check: Do reference checks in person.  If that’s not possible, you should at least try to keep reference providers on the phone for a few extra minutes.  The more you allow someone to talk, the more they will typically share.

Getting Honest Answers: A great way to establish trust with a reference provider is to let them know how vital a hire this is for you and your company. Highlighting the importance of the role also communicates the importance of them answering your questions candidly.

Keep in Mind: The loyalty of a past employer or coworker will be with the candidate. They don’t want to hurt this person by providing insight that might discourage you from offering them the job.


Take action to retain the talent that you worked hard to find.

It’s important to know both what’s happening at your company and how your employees feel. This may sound simple, but as you scale up your team, it will become increasingly more difficult.

Retaining Early Hires: Know who your top 20 people are at any given time. Keep a list of them if you need to and make the effort to frequently connect with them. “Small gestures go a long way” Kevin reminded us. The people who once had a direct line to you want to know that they still matter.

Retaining Talent at Scale: People will stay at your company if they like their manager and feel that that person is open and honest with them. Be careful not to be fooled by a manager who presents their best face to you, but has a team that is not performing well. If team/manager relations are not good, you’re going to lose one or the other eventually.

Keep In Mind: Knowing how you are perceived as a leader is highly valuable. Consider having a 360 review done of yourself once your team is over 40 people.


Hiring is only one piece of building a great team. Knowing when and how to let people go is just as important.

When a manager tells Kevin that they need to let someone on their team go, he asks them the question “Will [insert name here] be surprised when they walk into this room tomorrow?” If the manager say yes, then it’s clear to him that they haven’t done their job as that person’s leader.

Setting Clear Expectations: More often than most of us would like to admit, we, and our managers, are not as direct with employees and team members as we should be. When clear expectations have not been set, you must revisit the conversation as quickly as possible.

Keep it plain and simple: To measure an employee’s improvement, you’ll need to establish some metrics.  Give them tangible goals and a reasonable date to show their improvement by. If they have not shown signs of improvement by that date, they’ll know what to expect when they enter the room.

Keep in mind: In the end, letting an employee go is a hard thing to do, but if you can say that you were honest, fair, and communicative, you’ll have no reason to lose sleep at night.



Casey Taylor is the Director of Community at Female Founders Fund. Follow her on twitter at @casatay and @fcubedvc.