7 Questions You Should Ask Every Employee That Leaves Your Company

In the startup world, scaling up is typically the major focus. But not every employee is going to be the perfect fit, so a little downgrading is sometimes necessary. And when that happens, getting feedback about why they left is more important than any investor meeting on your books. Well, maybe not any investor meeting, but it’s still really important. After all, it’s the most honest feedback your company could receive.

We asked seven entrepreneurs what one question you need to ask employees who announce that they’re leaving your company. Take a look at their answers below and make sure your startup is prepared to listen diligently.

What Can We Do Better?

There’s so many reasons for employees to move on: new relationships, new opportunities, difficulties with the job. One thing that I always want to know is what we can improve as a company. Once that employee has announced they are moving, they feel more comfortable being honest so they can really give us feedback. I ask for the good, the bad and the ugly — and then try to make improvements.

– Marcela De Vivo of Gryffin


Firstly, I want to find out if it is something I can control. If it is something I cannot control, then I know there is nothing wrong with our company or culture; it is just what they wanted to do. For example, we have had two employees in the last month go on two different reality TV shows. In this instance, I knew this decision did not come from them having a negative experience with our company.

– Jayna Cooke of EVENTup

Would You Be Willing to Continue the Relationship?

It’s a small world, and just because someone is leaving your employment now doesn’t mean you won’t have the opportunity to work with them again, either as an employee or in another capacity. I encourage all former employees to keep in touch so that they continue to be a beneficial part of our network.

– Alexandra Levit of PeopleResults

Would You Recommend a Job Here to Others?

Their reaction and response to this question, with some careful reading between the lines, tends to get us much closer to an honest assessment for the reasons motivating an exit. Those genuinely seeking a career change or unique opportunity tend to be very positive. For those who may otherwise conceal deeper frustrations motivating an exit, it opens up the conversation by depersonalizing it a bit.

– Jake Goldman of 10up

Did You Have What You Needed?

When employees leave, I want to know if they felt they were given the appropriate tools and resources to do their jobs, and how often they felt that way. I want to eliminate any gaps between what I’m asking my team to do and how I’m helping them do it.

– Simon Casuto of eLearningMind

What Are Your Next Plans?

This allows the employee to give you information about why they are leaving without directly asking why they are leaving. It also gives them the option not to tell you if they aren’t comfortable. It’s a more personal approach then just thinking about the company and filling that position.

– Phil Laboon of EyeFlow

What Did You Like and Not Like About Working Here?

I ask for feedback (both positive and negative) about their overall experience working for my company. I have learned not to take it personally when someone leaves, as the modern economy is all about rapid change. But I do want to know if there were aspects of working for me that the employee didn’t like. I also want to know what they did like. This is a good opportunity to get honest feedback.

– Shawn Porat of JudgementMarketplace

Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world’s most promising young entrepreneurs. YEC members generate billions of dollars in revenue and have created tens of thousands of jobs.

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Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world's most promising young entrepreneurs. YEC members generate billions of dollars in revenue and have created tens of thousands of jobs.
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