Why Your Employees Leave And How To Keep Them

Carly Guthrie has been watching employees take and leave jobs for over 15 years. Turns out, the reasons people love and hate their work are largely the same across sectors. In an interview with First Round, Guthrie shares what she’s learned about why people quit, and what startups can do after an employee’s first day to make sure they stay happy, engaged in their work, and committed to your company (and to deleting every email they are most certainly receiving from recruiters)


There are a number of ways to keep your best people, but no silver bullet. As you think through your own retention strategy, remember the following:

  • Recognize that employees have lives outside of work — cultivate a deep respect for employees’ time. In Guthrie’s experience, employees will follow up with recruiters and other job offers if they’re even slightly angry, bored or dissatisfied “A really good CEO thinks about the bigger picture and realizes people have lives outside of work.” From 5 p.m. on Friday to 9 a.m. on Monday should be people’s own time, not the company’s. People do better work when they have lives of their own.

  • Employees usually don’t leave because of their boss. When employees leave because of their boss, it rarely comes from personality mismatches; it stems from a lack of confidence in you or themselves.  “Let’s say you’ve had a couple of pivots and you just don’t believe in the company or concept anymore. You lose confidence in the marketability or leadership,”

  • Counteroffers are (an expensive) band-aid; they won’t fix an employee’s fundamental unhappiness.  “When you tell an employer you’re leaving, you’re saying, ‘I’m unhappy. You may be able to buy me for another six months, but mostly, it’s the end of the chapter,’”

  • Building a genuine sense of community is crucial to employee retention. Make sure your hiring process incorporates and heavily weighs cultural fit.  “Your goal should be to make people feel like, ‘We’re all in this together and have a huge opportunity as a team.” This type of community enhances talent and collaboration and makes it very difficult to leave.

  • Hashing out a concrete “work from home” policy can improve employee happiness/retention, but it’s largely dependent on your organization’s needs. Work from home option can boost morale and encourage the employees to not consider going to work a mandated core. Managers need to communicate clearly to employees (and themselves) that they are results-oriented, while employees need to trust that it’s important and justified when managers ask for them to be in the office. It’s all about both sides respecting each other’s time and abilities — and, perhaps most importantly, communicating this mutual respect. Make sure you’re being fair across the board.

  • Good mentorship happens organically, and should be directed by employee interests and growth. It also creates another opportunity for a natural, short feedback loop you can definitely use.  Providing a good mentor, and making that relationship natural and easy, goes a long way toward keeping people in a role. It shows the employee that the company is invested in their personal growth, and that there’s someone (other than their manager) looking out for their best interests. But you can’t force it. Like mandatory fun, pairing people with mentors arbitrarily rarely works.

  • It’s never too early to invest in good HR, whether it’s processes or people. This can absolutely include HR contractors. An outside perspective can be invaluable for founders who need big-picture reality checks. “HR is not about algorithms. There’s a whole lot of humanity involved, and that gets messy. You need empathy on your team. You need someone who can say, ‘I might not agree with your choices, but I will put myself in your shoes and try to understand where things went off the rails.”

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