9 Bosses You’ll Encounter When You Resign
You did it! You landed your new gig, you’ve celebrated with friends, shared the news with family, and are ready for your next adventure! Until Sunday night…the night before you have to resign from your current role. You’re up all night tossing and turning, stressing out about talking to your boss. Are they going to yell at me? Are they going to tell me to pack up my things and leave? Will they pay out my vacation? Am I making the right decision? Oh my gosh…what if I cry?!
All of the emotions you are feeling are normal. You’ve spent months or even years working with this team, reporting to your boss, and giving this company your all. But it’s time for you to move forward in your career. Putting in your notice can be a daunting task and it definitely takes a toll on your emotions.
So here they are, the 9 types of bosses you will encounter when you go to resign:
Money Bags Mary:
Ah, Money Bags Mary. One of my favorites as a Recruiter. All of a sudden money is being thrown at you (that she somehow didn’t have 3 months ago during your annual revie) and promises are being made. I actually just asked for approval for you to receive a 20% salary increase and to get you stock options.
Empty Promises Edward:
Similar to Money Bags Mary, Edward will start telling you all the things you want to hear. You’re actually going to start leading a team, don’t you want that opportunity? We can put in place a new schedule for you where you flex your hours AND you get Friday’s off. Isn’t it funny how all of these promises get made when you’re on your way out the door? We see this a lot. All of the reasons you started looking for a new job in the first place will be “fixed” when you go to leave, only to have it all go back to how it was before, and you realize everything that changed was only temporary.
Disappointed Dave:
As someone who hates disappointing people, this one is the hardest for me. You’re leaving the team hurting, they really needed you, and here you are, moving on with your life and bettering your career for Dave to clean up your mess. They’ll play the disappointed dad card but act like they understand how you had to do it for you. They’ll push all of it off on HR and send you the “Best of luck” text on your last day.
Patronizing Payton:
Little comments they make after you resign may sound sweet and innocent, but the underlying idea of them are the exact opposite. After all, they were the one who trained you and put in all the hard work, long hours, late night calls that you took to ensure a product was released.
Passive Patrick:
He’s got no idea how to handle your resignation, so he hands everything off to someone else to handle. When he sees you in the hallway, he’s all smiles, but in team meetings he’s stressing to everyone how they’re all going to be bogged down with work since a certain team member is leaving them in a lurch.
Caring Catherine:
She’s so excited for you and knows you’re going to do amazing things in the future and she was lucky to have been part of your career journey. She welcomes a continued friendship once you leave and has already set-up a lunch with you in a couple of weeks to see how your new role is going.
Happy Hour Hank:
You’re leaving?! Okay…okay…we can make this work. That’s exciting for you. Let’s do a happy hour with the whole team this Friday so everyone can get a chance to say goodbye. The boss that is everyone’s friend and never the bad guy. He may be a little teary eyed at the HH, but he’s the life of the party and doesn’t want anyone to stress about you leaving (or the fact it could cause a domino effect) leading us to….
… Overcompensating Oscar
He’s upset you’re leaving, obviously, but he’s now freaking out about what will happen to the team and if others will start resigning. He starts overcompensating, being overly accommodating and eager to help out the team, overstepping and micromanaging galore.
Can’t you Stay Longer Carrie:
She takes the news you’re leaving well, but then keeps asking for more even though you’ve already put a plan in place for you to leave. Can’t you just stay until this release? We have junior engineers; we need your help developing just a little bit more. We need you to stay a week longer for knowledge transfer. The requests go on and on, and she makes you feel guilty for spreading your wings and moving on with your career.
In all seriousness, resigning from your role is hard, it’s emotional, and regardless of how your boss reacts you are going to second guess your decision. No matter your reason for looking for a new role and accepting an offer, change is hard, and if your boss starts promising things (that deep down you know they can’t deliver on) it will cause you to second guess yourself and maybe even stay. Do yourself a favor. Before you even start your job search write down why you are looking for a new role – and then revisit that list before you go in to resign.