All Articles Leadership Management 15 lessons learned from employees who left

15 lessons learned from employees who left

Every employee departure offers the opportunity to learn. Here are 15 lessons from Young Entrepreneur Council members.

7 min read



Kev Seto/Unsplash

The Young Entrepreneur Council is an invite-only organization composed of the world’s most promising young entrepreneurs. In partnership with Citi, YEC launched BusinessCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses. Read previous SmartBrief posts by YEC.

If you enjoy this article, join SmartBrief’s e-mail list for our daily newsletter for entrepreneurs.

Q. What lesson from an employee departure really stuck with you, and why?

1. Hire for values alignment, not just skill

Hiring for values alignment can be a challenging process, but the rewards are many: higher performance, lower turnover rates and a happier culture. We have strong values at our company, and they’re integral to our hiring process. However, in the first year of business, we didn’t make values alignment a priority and often hired wrong. It taught us the importance of hiring for values, not just skill. — Sunny Bonnell, Motto

2. Outliers seldom work in a team

We all would love to have an outlier in our team who can move the needle from point A to Z much faster and in a better way than any other. But most often, what we realized is that these outliers seldom work well with teams. Unless you can find a role that the outlier(s) can perform on their own, we would rather hire great people who can collaborate with others and work in teams. — Rahul Varshneya, Arkenea

3. Be proactive in addressing situations

The first time I had to fire someone was one of the hardest things I can remember. I had put my head in the sand hoping that a small problem would resolve itself. Unfortunately, that never works. It only grew to the point it was untenable for everyone. I look back on my failure to pro-actively address the situation often. Your culture is determined by the worst actions you tolerate. — Douglas Hutchings, Picasolar

4. Employees need to be comfortable approaching you

We had someone leave for reasons I did not know of until it was too late. It is important to switch perspectives, to look at myself as a manager, through the eyes of my employees. Do we communicate? Have I created a comfortable environment for my employees to approach me confidently to express any questions or concerns? Shredding a layer or illusion of “boss” is a simple way to encourage dialogue. — Phil Laboon, WUDN

5. It’s all about fit

We lost an employee who told us she loved working with us and our culture, but that she was no longer a fit for where our organization was growing. I realized that no matter how much we liked her, we had to let her go so she could go and grow someplace else. Since then, she has flourished; we just weren’t the right fit anymore. — Brandon Dempsey, goBRANDgo!

6. Companies should always ask staff about job satisfaction

When we had a long-time employee leave, it was such a shock and we had no idea that they were even considering it or were unhappy. It made me realize that it’s important to stop and take the time to check in with everyone and gauge their level of satisfaction with their jobs. That calls for more one-on-one sessions as well as regular performance reviews. — Andrew O’Connor, American Addiction Centers

7. Be clear about a leaving employee’s plans

When an employee decides to leave the company, make certain that you both keep open lines of communication about their plans, so as to avoid any potential hiring conflicts or confusion in the process. I had an employee leave after insisting she would stay a while longer, and the miscommunication left us scrambling to train her replacement. — Rachel Beider, Massage Greenpoint, Massage Williamsburg

8. Teach them life lessons when necessary

We use Gmail in the office. After an employee left we found hundreds of chat threads between co-workers and friends that she failed to delete, from complaining about the company to her sexy Friday night date. We were shocked. However, we decided to tell her of her snafu, so that in the future she knows to not discuss things on company channels or at least delete them before leaving the company. — Kim Kaupe, ZinePak

9. Documentation and standard processes are important

When an employee leaves, they don’t always leave behind a thorough understanding of how their successors can do their job. So, we’ve made it standard practice that we all try to document procedures and processes, which allows us to have a user manual, of sorts, that new hires can use to fulfill the role that the departing worker left behind. — Firas Kittaneh, Amerisleep

10. Make them comfortable about sharing long-term plans

I had a key senior employee leave and it could have been very disruptive to the business. But it wasn’t because of one crucial thing: He gave me several months’ notice. Make sure that employees feel 100% comfortable being open with you about their career plans, with zero percent fear of retribution. They will let you know as soon as they start thinking about a move, and it will buy you time to plan. — Roger Lee, Captain401

11. A single individual can make a huge difference to the culture

We’re taught to build organizations so they don’t depend on any one individual. That’s the right approach, but a single individual can make a huge difference to the culture, productivity and innovativeness of a company. Of course, we should design companies to be resilient to employee turnover, but we shouldn’t discount the importance of the people we work with to our overall project. — Vik Patel, Future Hosting

12. Don’t burn bridges

Employees, especially those early in their career, may not have learned the necessity for grace as they transition from their job. The tech industry is small and the desire for references is great. Forming a professional bond with your former employers will be advantageous for any employee as they move on and up in their career. Do not burn bridges: You may need to cross them again one day. — Jennifer Mellon, Trustify

13. Passion matters

Last year we had an employee leave after three months to pursue a job very specific to her degree. The lesson I learned: passion matters. Although she claimed otherwise, our organization was a stop-gap until she found something in her field of choice. — Ben Camerota, MVP Visuals

14. Happy employees are the best employees

I once had an employee who left to chase a more balanced schedule. It was then I knew I had to be even more open to flexibility when it comes to my employees’ needs. Happy employees are the best employees. You can’t always satisfy their every want, but when you can, you should. — Renato Libric, Bouxtie Inc.

15. It’s natural for employees to come and go

One of the first employees I ever hired left after working with me for three years to start a family. It was good reminder that while my business is a very big part of my life, for my employees, it is not their be-all, end-all, and that is OK! It taught me that employees come and go, but each serves a purpose for the time they’re with you, and that shouldn’t be taken for granted. — Leila Lewis, Be Inspired PR