How Giving Second Chances Can Help Your Business

March 1, 2017, 2:00 AM UTC
The concept of choice
The concept of choice: many doors in a green field
pertusinas—iStockphoto/Getty Images

The Entrepreneur Insiders network is an online community where the most thoughtful and influential people in America’s startup scene contribute answers to timely questions about entrepreneurship and careers. Today’s answer to the question, “What are some of the biggest misconceptions about startup life?” is written by Carly Zakin and Danielle Weisberg, co-founders of theSkimm.

Once upon a time, we had a very nice stalker. (Editor’s note: We don’t usually respond well to this. This should not read as encouragement.) He was a senior in college and emailed us constantly about his love of the brand and why he wanted to work for theSkimm. There was something about his notes we liked, so we had our assistant meet him during his spring visit to New York City. She came back and said, “I don’t know what he would do but he is very smart.”

Other founders had always told us to be opportunistic for talent. We hadn’t been very good at that in the past and had hired based off of our current needs. But we knew we were getting ready to make a social media hire. So we gave him a homework assignment and hired him. He moved to New York City a few days after college graduation.

And then we realized we made a mistake. The work wasn’t clicking where it needed to be. He was trying and we were trying and after 30-plus days, we knew we had to make a change. There’s no better way to say this: It sucked for all of us.

See also: Why Entrepreneurs Shouldn’t Be Working Every Waking Hour

But then we told an advisor about the situation and she asked, “Is this person a culture fit?” The answer was yes. “Would you like to see this person work out?” Definitely, we said. “Well, is this person in the right role?”


Well, Captain Obvious threw us for a loop with that question. So we started giving it some thought and having our managers give him different homework assignments to narrow down his strengths.

We sat him down and said very honestly, “You’re in the wrong role. Be flexible with us and we will try to find you the right role.” To his credit, he listened and trusted us. And now, six months later, he is flourishing in a totally different role on our team, with a brand new skill set under his belt. He has always been driven and a great culture add —but now he is actually helping us expand a part of our company.


This was a pivotal moment for us as managers. We were always advised to hire slowly and fire quickly when we knew someone wasn’t working out. But we had to learn the hard way that sometimes, you hire people for the wrong role, and the right role may be right in front of you. Now we are constantly assessing whether everyone on our team is in the right role and for this lesson, we will always be grateful to this employee for happily proving us wrong.

When a job isn’t working out, think about why. Is it a culture-fit issue? Is the necessary skill set missing? Or is the right person in the wrong role? We’ve been labeled as founders who are slow to hire. And that’s true. We put a lot of thought behind each person we bring in to make sure they will be a good fit for the existing team and bring traits that we don’t already have.

That being said, when we decide someone isn’t a fit for the role they’ve been hired into, it’s never a surprise. We trust our team, and we want them to trust us that we want them to succeed—it’s an ongoing conversation. Don’t be afraid to change things up.

This piece originally appeared on Medium.

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