BogiDope, an F-16 executing a hard left turn.

Dear Boss

Breaking up is hard to do. 

Of the many stressful parts of separating from the active duty, a hurdle that some find higher than others is expressing this decision to your commander. Regardless of the kind of relationship that you have with this person, there is inherently some awkwardness here. But there doesn’t have to be. In fact, you should feel very comfortable by the time you have arrived at this point because:

  1. You and your family have made up your minds that this is the best thing for all of you. Therefore, you are not seeking counsel or opening up a discussion here- this is a statement. A one way conversation. There might be the suggestion from your boss to “take some time and think about x,y,z…” You need to be clear that you have done your due diligence, and that this decision is not going to change. You are not here to negotiate, you are here to be transparent about the next step of your life.
  2. You have done your homework. You should be familiar with what the next series of steps needs to be from a personnel/administrative standpoint because your commander may not be! Part of your conversation with him/her will entail your timeline and needed milestones to make this a successful separation. This will help put you and your commander on the same sheet of music as far as what needs to be done on both his end, and yours. Some of these things will fall on their end, some on yours, and a lot on both. You may separate on your own, but a lot of people and agencies are involved to help make that happen. 

If you are in a scenario (like most will be) and you know your commander, have worked with him/her, and maybe have even socialized together, then there’s no real need to schedule a formal meeting here. At the same time, don’t tell them as they’re walking down the hall, leaving for the weekend. Mondays aren’t particularly great either- maybe a ton of things arise that are going to take their attention to start the week. Adjust to the tempo of what’s going on, but typically early/mid week during the morning is a fair time to have this meeting in their office, or wherever you would have such a kind of conversation with them. 

If you have a new commander that you do not know, the same rules apply as far as the scheduling is concerned, but try to get on his/her calendar as a professional courtesy. Go through their exec/secretary if you must. Unlikely they will ask you what the meeting is about, but if they do, “Career Counseling” is a fair description. 

Now that you have the right time and place figured out, you want to have an idea of what you want to get out when you do sit down. It will probably start with some casual banter, and you can play that by ear as far as how long you want that to go. But get down to brass tacks sooner than later. No need to memorize anything, this isn’t the Gettysburg Address. But definitely don’t wing it either. You want to sound calm, confident, and collected, so maybe run it by a trusted agent or your spouse first. 

On that note, we all know how small a squadron can get, so don’t be surprised if this doesn’t come as a surprise to your boss! 

A Couple Quick “Do’s” and “Don’ts”… First the Do’s:

  • Express genuine thanks for the opportunities, experiences, and privileges that the military has given you
  • Express that your mind is made up, that this is the best decision for you and your family, and that your decision is not negotiable
  • Express that you would appreciate it if all parties involved would respect your decision, and help you through the myriad of tasks that will come with the formal separation process
  • Express that you will work as hard as you ever have until your last day on the job

Almost Equally Important, the Don’ts:

  • There’s no need to express your displeasure with any facet of what is going on with your current or previous job/coworkers in the military. This is not the place for that and it will muddy the water of your other points. You may get that question, “Are you leaving because of…” Don’t take the bait – stick to what you came in ready to talk about. Airing dirty laundry just clouds the clear path that you all need to be on to make this process as painless as possible. 
  • Don’t be combative or resistant if your boss insists on making you listen to other options they might want to put on the table. Depending on the phase of your career, they might want you to talk to one more commander up. This is ok, so don’t refuse to talk to anybody if your boss is insistent upon having you do so. As long as you stick with your talking points, they all get the same message, and they can all be on board with helping you. 

Maybe you already have a Guard/Reserve job lined up. Maybe you are completely cutting ties with the military all together. Maybe you’re moving across the country or just down the road. The last part to remember is that the intricate details of your plan and future do not need to be fully disclosed here. There’s a good chance you’re not going to have all the details figured out! Have the confidence to know that the pieces will fall into place in due time, and that confidence will shine through to your boss. 

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