Subscribe to Veteran Led


Episode 31

Episode 31: Terminal Leave: Crafting Legacy Through Connection


Leave it better than you found it. In this episode of Veteran Led, John will navigate the complexities of bidding farewell to a role or brand after years of dedicated effort. He’ll share how leaders and team members can build relationships that stand the test of time, leaving a lasting impression on both personal and professional fronts.


Welcome fellow veterans. From the tip of the spear to in the rear with the gear, I went from active-duty Infantry to reserve-component logistician. I’m your host, CEO, entrepreneur, trial lawyer, and Lieutenant Colonel Retired, John Berry. The military lessons that I learned helped me grow an eight-figure business that has maintained consistent annual double-digit growth, landing on the Inc. 5000 list of fastest growing companies in America every year for the past seven years and has allowed me to continue to serve America’s heroes.

Terminal Leave: Leaving the Organization Better than you Found it.

If you served you likely served in multiple positions; you would transition from one position to the next every two to three years. As you approached your final days in uniform or your retirement ceremony, you probably thought back on your greatest accomplishments in the military. You reminisced about the best of times, and you still have fond memories about your military service.

Your civilian organization should be no different. There should be great right/left seat rides, and when someone leaves your organization, they should be proud of their service and proud of their accomplishments. It’s like colleges, right? Many of us went to college for four years and most of us are proud of the organization or the institution from which we graduated. You see the Alabama grads on football Saturday, they’re all wearing their Alabama shirts, they’re proud to be an alumni.

Let me ask you a question: If someone left your company today, would they still wear the company gear? Would they still wear the company logo? Would they be proud that in their past, that they were a part of your organization, of your team? Just like any university or the military, alumni relationships are key to your organization. So you have to look at how you leave the organization when you leave it. Do you leave it as a better place? But also, when team members leave, did they leave it as a better place? Did you help them to achieve skills? Did you make them a better person, a better leader by the time that they had graduated from your business?

Those relationships are important to you professionally, and they’re also important to your organization because as people leave, they will talk. And they will talk about the experience they had. And your former team members can be your best recruiting team members because they can go out and spread the word of a great experience and great opportunity they had. Similarly, if they didn’t have a great experience, they can bash you, which can thwart your recruiting efforts.

It’s also important to keep in mind that as team members leave your organization, they will maintain relationships with other team members. So we have to be intentional about nurturing relationships within our teams so that those relationships go beyond the employment relationships and spread into our futures.

As the leader of your organization, your legacy is your leaders. And it’s not just the leaders that stay that you develop, it’s the leaders that you develop that leave and legacy is important to any organization. Legacy ensures longevity.

One of my favorite recruiting commercials came from the Navy about 20 years ago. I saw it on the TV and there’s all these action photos of people jumping in boats and scuba diving. And the caption was, “Do you live the type of life that someone will want to write a book about?” When we reframe this question to fit your organization, the better question becomes, “When a leader leaves your organization for a bigger, better future, and they write that book, that autobiography, are they going to mention your company?” Are they going to mention you as a leader? Did you do something worth mentioning? Did you develop and help them in a way that they cannot forget you? That is the test of leadership. Will they remember the impact that you had on them? 

This is also why leaving on bad terms can be a horrible thing. Whether someone leaves your organization on bad terms, or you leave an organization on bad terms. There are a few reasons for that. First of all, if you leave on bad terms and you badmouth that company, people aren’t really paying attention to what you’re saying, they’re viewing you and your reactions and your emotions, and they’re probably going to see you as a negative person, and so it doesn’t always have the effect that you want it to have.

Similarly, if you have a team member leave your team and you’re saying bad things about them publicly? That makes you look like a bad leader. And it also makes it look like you’re a sour, angry person. And so you have to cut out the negativity. Whether you leave the organization, or someone leaves your organization, it is always best that that team member leaves on good terms.

And there’s another reason for that too. That team member dedicated their most important asset to you, their time. And they dedicated their time to you in exchange for money and they were paid, but the service they provided your organization is invaluable. It is important that they are recognized and honored for their dedication to the team for the time they spent. Whether they were a superstar or whether they were mediocre, regardless, you need to honor their commitment to the team. That should be part of your culture, that you recognize that people decided to be part of your team and your obligation as the leader is to recognize that commitment.

The other thing that happens when team members leave on bad terms is that they lose relationship capital or social capital with the former team members. And when a team member leaves on bad terms, that team member is an outcast. So, if you leave an organization on negative terms, you’re probably going to lose some relationships. Conversely, if you let a high performing team member leave on bad terms, they may have the social capital to pull some team members with them.

So it’s important that if we don’t get along, if there’s reasons for the split, we have to act like professionals. We have to honor the team members that leave, and we want them to leave on good terms. It’s never good when someone leaves on bad terms. It’s just not good for the organization. 

Now, that being said, you will have team members that will leave on bad terms. It’s inevitable. The more you grow as an organization, the more likely it will happen. There’s a great book about culture and reducing workplace drama by an author named Cy Wakeman. The name of the book is “No Ego.” I’ve also heard Cy speak publicly, and I can’t remember where this came from, the book or from one of her speeches, but she talks about team members leaving and blaming the boss. And there was a study that was conducted over ten years, and they asked employees that left organizations why they left. And they noted a large number cited the boss or the leadership. They followed those employees for over ten years, and what they found is over the ten year period, those employees had three to four different jobs, and in all of those jobs, the reason why they left was because of the boss or the leadership.

This is quite telling, right? If someone leaves because of the boss or leadership one time, that could be accurate. But if they’re always leaving the team because it’s the boss or the leadership’s fault, then we probably have an accountability problem. It’s like the friend that’s been married four times and they’re getting ready to get married for the fifth time, and they’re wondering if they have the right selection criteria for a partner. No, the problem is probably you, the common denominator is probably you.

No matter how great your interview process, you will eventually end up with team members who have low accountability, and they will show you in their work. And when they show you who they are, believe them. Unfortunately, there isn’t much you can do to help them or to fix them. They are going to leave the organization and probably going to leave the organization on bad terms. But that doesn’t mean that you, as a leader, don’t take the high road. You must always take the high road. Don’t wrestle in the mud. Treat them with respect. Treat them with dignity. Give them the opportunity to be a success somewhere else.

You just have to deal with the reality that not every team member is going to work out and when they don’t, some of them will take responsibility, but others will blame the leadership or blame the organization, blame anything and anybody but themselves, because that’s just something that they’ve done their entire lives. And this is contrary to what we’ve learned in the military. This is why I like to hire veterans. I like to hire former athletes. I like to hire kids that grew up on farms, that know what a hard day’s work is worth, and that also know that accountability is everything.

One of the best ways I’ve heard of to stop this problem is to go back to the interview process and ask one simple question: “Tell me about your worst boss.” Notice the pause. After you ask the question, pause and let them answer, and let them go as long as they want to go. And from that answer, they will show you who they are. They will either slam all their bosses or slam one boss pretty hard. And if you see a pattern of slamming bosses, then you know that you’re going to be the next boss that they’re going to slam.

Another technique that I learned from an HR professional was that when you ask for references, don’t just call the references, ask about other coworkers and get information to contact them. That was some of the best advice I got, and I know that some HR teams love to do that. And I’ve heard from some of my friends, some of my peers that say that has been invaluable.

And I can think of a one team member that I hired that he had glowing references from everybody. And I asked, I said, “Well, who else have you worked with in these organizations?” And I got names. I contacted those individuals. They gave even better, even brighter glowing recommendations. And that’s why I knew I had to hire this individual immediately because his references said good things about him, but the people that he didn’t list as references said even better things about him, so I knew that this kid was a winner and I had to hire him.

To recap, this is what right looks like when someone leaves your organization: They’re a proud alum. They’re proud that they worked for your team for however long they worked there. Number two, they continue to refer clients and customers to you because they believe your organization is the best fit to solve that type of problem. And number three, they continue to refer their peers to you, their friends, to you as employees. They are not only sending you clients, they are sending you team members because they believe in the organization and they want it to continue to grow.

And hopefully they’re still wearing your swag, just like the university of Alabama graduates who show up every Saturday with Alabama shirts. If they’re still wearing your swag if they leave your team, wow, that says something. They were proud to be part of your organization, and that tells me that you as a leader have built something special. 

Another key reason why it’s important that when you leave an organization, you leave it better than you found it, or when you have a team member that joins the organization, they leave a better leader, better person, better technician than when they came to your organization, is because they may come back around. I can remember a book I had to read in college in an English class. It was called, “You Can Never Go Home Again” by Thomas Wolfe and the premise of the book was that as you move through life, you can’t come back to the same place. And it’s almost like you never step in the same river twice. You change, places change, and you come back, and nothing really comes back the same.

But that doesn’t mean someone can’t come back to your organization. And if someone leaves on bad terms, yes, they should not come back to the organization. But if they leave on good terms and they develop new skills, then you should welcome them back, provided they’re qualified and they’re still a cultural fit.

Now, if you have a team member that is disrespectful and leaves on bad terms, do not hire them again. They can’t come home again. Because if you let them come home, they will not respect you, and they will not respect the team. But even worse, if you let them come back after that, your team won’t respect you. They will see you as desperate. You’re so desperate that you had to bring back the person that was disrespectful to you back onto the team. That just shows weakness as a leader and that’s the type of weakness that I would never want to follow. 

In my organization, whenever we get a new team member, we want to celebrate that. And when a senior team member or old team member leaves or moves on, we also want to celebrate that.

Back in ancient Rome, when a general would come back from war, the general would be praised and would parade the soldiers through the streets with the spoils of war, and the citizens of Rome would line up and cheer and clap for the soldiers. So parades go way back. And when Caesar came back from one of his battles, he was about to cross the Rubicon River to go back to Rome, and as he approached, there was a messenger from the other side. And the messenger said, “I have orders from the Senate. You will not cross the bridge under arms. You will not have your triumphal procession. You must report to charges placed on you by the Senate.” Caesar marched into Rome and took it, and history has told the rest of the story. Julius Caesar, the great general, became the Emperor of Rome.

Now, the lesson in all this was, do not fail to recognize your team. Caesar believed, as all generals did, that it was his religious right to have the triumphal procession, to be celebrated for his victories. And when he was denied that, he marched on Rome and he took it. The point is this, is that you as a leader can either celebrate the victories of your generals or you can put them in a position where they feel unappreciated, unwanted, unwelcomed, and they will create their own empires.

When you have that successful team member who leaves the organization and comes back years later, it may be great to bring them back, it may be in that organization’s best interest. Think about this; a young marketing intern leaves your team, goes to work for Fortune 500 companies, and five years later comes back qualified to be the CMO. Talk about a triumphal procession. That young leader that you developed went off into the big world, worked for companies a hundred times the size of yours, came back, and now wants to lead your organization. That is a great compliment. Give them that triumphal procession, celebrate them, invite them back into the organization. This is the individual who left for a bigger future and now wants to rejoin the team. I generally welcome those individuals with open arms. And if I have a spot for them on a team, I like to bring them back because I love the success story and I love the story that they were a proud alum who came back to the organization. And maybe you won’t have a position for them then, but they have all those contacts from their relationships with bigger organizations, and they can do you a lot of favors. In sum, always keep your door open for your champions, even after they leave. But if someone betrays you, shut that door forever and lock it.

One of the things that I love to discuss the most on the Veteran Led Podcast is building that really strong culture that keeps the team together, and that even when team members leave, they want to come back. But there is a downside to building a really strong culture, which is nobody wants to leave ever, even when they can no longer do the job. And that’s tough, because as a leader, you have to have that difficult conversation about performance. That conversation becomes even more difficult when that team member has a lot of close allies, and they get along so well that your team wants the underperformer to stay just because they like that underperformer so much.

And so when you have a really strong culture, one of the toughest things you have to do as a leader is to let the team member know who desperately wants to be a part of the team, who will do anything to be a part of the team, that they’re no longer part of the team. And that is the difficult part of leadership. But, if you’ve ever been in the Army school system, you know that you must have standards. And if an individual does not meet the standards, they don’t graduate.

Similarly, in the Army, we would say, we never leave a fallen comrade. And that’s true on the battlefield, but in garrison, we chapter people out. We administratively separate people. And that is the difficult thing about having a tight knit culture, is that everyone wants to stay, but not everybody gets to stay.  But that is when you know you have an elite organization.

So when is it good to leave? When is it good for you as a team member to leave your organization? When is it good for both the organization and for the individual? Well, if a team member has a skill and they want to develop that skill and you can’t give them the position that’s gonna allow them to develop that skill, it’s time for them to go. And that is a good thing. That should be celebrated.

Anytime a team member can get a bigger, better future at another organization, you need to celebrate that and encourage that team member to leave as much as it may hurt you. That is the selflessness of leadership; that you care enough about your team members that you will personally suffer to ensure that they get to the next level. And I’ve had that conversation where I’ve told a team member, it hurts to see you go. We’ve invested a ton of time and money in your training. I personally like and respect you. I’ve loved seeing you develop, but I can’t provide you the opportunity that that other company is offering you, and so I would be failing you as a leader if I didn’t tell you to go.

The second example of when it’s good for a team member to leave is when they want to leave to start their own company. They can say, “John, we’re so inspired by what’s happened in this organization, we want to build our own. We want to do what you’re doing.” Great. I respect that. And that may be painful, we may be losing key team members, but if that’s their heart’s desire, we have to support and respect that. And we have to be proud that our courage was enough to give them the foresight and the courage to leave the organization, to do what we do.

Another good news story when a team member leaves, is when they leave to support a partner or a spouse. We’ve had this happen where our team members start families, and they decide that this is not the right season of their life to do what they’re doing, and they want to do something different. That’s okay. That’s a good news story. That shows our team that we provided value, and we provided our team member enough support that they felt that they could live the life they wanted to live and now that they’re in a different season of their life, they want to do something different, we want to support them. Who knows? Maybe they’ll come back. And if they were great, you’ll want them to come back. You’ll want to stay in touch with them and you will want them to be proud alumni of your organization.

The final good reason for someone to leave your company is retirement. Now, retirement is tough because a lot of times when an individual retires from your team, they may have 10, 20, 30 years of experience and there’s this gaping void of institutional knowledge that is now just gone, wiped out when they leave. It’s important that you capture it. But when they leave to retire, that’s a good news story because your organization provided them with the financial stability to retire. You provided them with the sense of accomplishment so that they can retire and feel like they had a fulfilling life’s work in your organization.

Now, that being said, when team members hold on too long, it can get ugly. And I have seen this happen in other organizations where the lawyers do not want to retire. They want to die with their boots on, but they start to lose their mental edge. They start to lose their capabilities and it doesn’t end as they thought it would. So the reality is, having a team member retire and retire on their own terms is a success story that you should be proud of.

As we conclude this segment on terminal leave and leaving the organization better than we found it, I want to share my experience of terminal leave. Like many of you, I had to sell back my leave when I got out. And when you sell back your leave, you generally lose money. My unit was going to NTC, the National Training Center, and I didn’t have to go. I had my terminal leave built up. I could have went on leave, but the team asked me to go with them. And I wanted to make sure that I left the organization better than I found it. I wanted to make sure that I gave everything that I had. Why? Because I saw all the military leaders before me do that. When we finally get to go on terminal leave and end our military careers, getting those last few weeks of paid vacation, we can rest and enjoy it because we know we gave all we had and that our organization is going to be even better after we’re gone.

After Action Review for Terminal Leave: Leaving the Organization Better than you Found it:

  1. Keep your alumni network strong. 
  2. You can return and you can allow your great team members to return.
  3. Some turnover is good.

Three Down:

  1. Never leave an organization on bad terms and if you’re the leader of an organization, don’t let your team members leave on bad terms if you can help it.
  2. If a team member leaves on bad terms and they are disrespectful to you or the organization when they depart, they can never come back.
  3. When someone shows you who they are, believe them.

Thank you for joining us today on Veteran Led, where we pursue our mission of promoting veteran leadership in business, strengthening the veteran community, and getting veterans all of the benefits that they earned. If you know a leader who should be on the Veteran Led podcast, report to our online community by searching @veteranled on your favorite social channels and posting in the comments. We want to hear how your military challenges prepared you to lead your industry or community, and we will let the world know. And of course, hit subscribe and join me next time on Veteran Led.

Berry Law

The attorneys at Berry Law are dedicated to helping injured Veterans. With extensive experience working with VA disability claims, Berry Law can help you with your disability appeals.

This material is for informational purposes only. It does not create an attorney-client relationship between the Firm and the reader, and does not constitute legal advice. Legal advice must be tailored to the specific circumstances of each case, and the contents of this blog are not a substitute for legal counsel.

Subscribe to our newsletter

The Service Connection

Our monthly newsletter features about important and up-to-date veterans' law news, keeping you informed about the changes that matter.

Skip to content