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When to Cut Ties With a Longtime Employee

John Rampton

Entrepreneur and Connector

Startup culture is all about disruption. It’s perfectly normal for one person to work two or even three jobs within a year, bouncing from one organization to another in the hope of finding the right fit. It is hard when the time comes to cut ties with a longtime employee.

When an employee finds that fit, though, the bonds they form with their coworkers and leaders become as strong as those of a family. Teams lift one another up in the bad times and celebrate together in the good, all in pursuit of a shared vision.

Unfortunately, sometimes even the best partnerships break down. A longtime employee begins to disagree with the direction of the company, and a few small disagreements turn into irreconcilable differences. Whether it’s a day-one employee or a co-founder, sometimes even the longest tenured employees need a change of scenery.

What it’s like to fire an old friend.

I recently had to let go of a longtime employee because of a disagreement like this. We had worked well together for years, but recently, we had begun to see the future of the business in different ways.

While there are many valid ways to grow a business, no company can grow if the people within it don’t agree on the path to take. This employee and I disagreed on when to pursue financial growth, employee skill growth or opportunity growth. The projects he felt most passionately about, while they had great potential, did not align with what our business needed to accomplish to achieve the growth I envisioned for us.

We had one conversation about this issue. A few months later, we had another. Both of us realized that our minds were made up. Because the issues were central to the future of our company, I made the decision to let my longtime employee go to pursue opportunities that better aligned with his personal passions.

It wasn’t easy, but if the situation were to arise again, I would make the same decision. A company cannot push forward if the people running it do not agree about which direction is correct. I am grateful for the progress we made together, though, and believe that both of us will benefit from the separation.

Use this process to determine whether a longtime employee would be better off somewhere else:

1. Look for signs of vision mismatch.

Some longtime employees stick around despite mismatched visions, but most of them continue to work for the company because they believe in what it’s doing. When they begin to show signs of deeper disagreements, step in quickly to determine if the disconnect is temporary or more serious.

Has the employee begun to delay projects or submit work below his or her normal standard? Does the employee disagree more frequently with leadership or repeatedly address the same concerns? Employees and their companies need to agree on what’s worth doing before they can agree on anything else.

2. Have an honest conversation.

If the employee appears to be legitimately unhappy with the situation, don’t put off the inevitable. Schedule a meeting as soon as possible to discuss the issue. Maybe the employee is just having a bad month or two and taking it out on work. Whatever the reason, the only way to discover the truth is to ask directly.

Start the conversation by communicating the observations from the previous step, then sit back and listen. Encourage honesty -- some conflict-averse employees would rather suffer through vision disagreements, but it’s better to rip off the bandage early. If the issue involves something other than the company’s direction, handle that issue on its own. If the problem lies with vision, though, dig deeper.

Is the issue with a specific part of the vision, or has the whole thing become irreconcilable? Did a single decision set off this change, or has a series of events led to this moment? Does the employee have a point that the company should address, or is the company committed to this vision regardless of the criticism? The answers to these questions determine what kind of action the disagreement merits.

3. Consider alternatives.

Depending on the severity of the disagreement, both sides might be happy with a solution less serious than termination. Perhaps the employee could work in a different role, or the projects that started the problem could move to another department.

Don’t put extra work on other people just to keep one longtime employee. That’s not fair to anyone. Instead, look for a solution where the employee can continue to be productive without coming into conflict with the mindset that started the disagreement. If no such solution exists and the employee is not willing to budge, move to the final step.

4. Make the call that’s best for the company.

As a longtime employee, this person is probably a trusted friend and capable worker. However, if he or she has developed an irreconcilable disagreement with the company’s vision, both sides would be happier if the employee were to find somewhere else to work.

Hard though it may be, remember that the needs of the company come first. Retaining an employee who does not want to help the company achieve its current goal is bad for everyone. The employee might not want to lose the job, but in the face of long-term dissent -- and with the potential for that dissent to spread -- do the right thing for everyone and fire the employee with dignity.

No one wants to go through this process. I know I didn’t. Unpleasant as it was, though, it was the right call for my company’s future (and for the employee’s future, too). If this situation sounds familiar, follow these steps to determine whether a longtime employee is no longer the right fit for the organization.


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