Making the Awkward Jump from Peer to Boss

Awkward Turtle Hand GestureLife is full of awkward moments: the first kiss, an interview candidate having spinach stuck in their teeth, having your boss catch you leaving the wrong restroom. But one of the most awkward situations you can encounter in business is when someone goes from being a peer to being the boss. There are two sides to that awkward moment too – either you’ve become the boss or your peer has.

Usually this occurrence is an unexpected situation. Many organizations are actually wise enough to prevent it from happening exactly because of the weird dynamics such a change can create. Given that it’s unexpected, it prevents all involved from preparing for the impending change (which in turn makes it even more awkward when it happens). Many times such situations are the direct result of a reorganization or the departure of some individuals from the team which creates an immediate need for a fill for that vacancy.

There are three situations I’d like to explore: you become the manager, your peer becomes the manager, and you’re the big boss considering creating such a situation within your team.

Congratulations Charles! You’re in charge!

It finally happened! You’ve been promoted. Congrats! Break out the Martini & Rossi Asti Spumante (you’ve got great taste and it show-ohs!). Oh wait… what? You’re now leading the team just seconds ago you were a member of? Weird.

Suddenly people you were “buds” with become your subordinates. They’re instantly on pins and needles wondering how you’re going to behave as their manager since you’re now clearly no longer a member of the gang. You’ve moved from the proletariat to the bourgeoisie. You’re no longer privy to the snarky jokes or inside gossip about what’s going on in the organization – you’re now the subject of said comments, jokes, and gossip.  But if you handle the transition well by doing four simple things, it’ll go a lot smoother.

I was put in exactly such a situation. I worked with three other hard charging guys who were exponentially more intelligent than I. They knew their business units better than anyone ever had and we all got along quite well as friends. We shared ideas and thoughts on what was going well (and not so well) in the organization and we worked together very collaboratively. Then came the day of the reorganization and their three business units showed up on the org chart as reporting to me. The first conversation was a little tense and anxious.

Everything worked out fine. How?

– First, acknowledge the weirdness. It’s the elephant in the room. Get everyone to say it feels awkward and get them to commit to making it work (you have to make the same commitment by the way). Acknowledging discomfort is the only way to truly focus on it and make it go away.

– Second, articulate your leadership approach and philosophy (maybe even lay out a few leadership principles). Don’t lay it down as law – simply state how you plan on leading the team and what your expectations are. Also ask what their expectations are of you and commit to meeting them.  If you’re serious about doing a great job of articulating who you are as a leader and what you expect from them, I strongly advise you to grab this book and follow the method I’ve laid out in it.

– Third, let them do their job. They’ve been doing it well. In their minds, there’s nothing worse than someone (especially a “peer”) coming in and micromanaging them when they’ve been doing well before the change. Resist the urge to lay down the law or tell them how to do things because you think such behaviors will send the message that you’re in charge. Everyone already knows you’re in charge! The org announcement said so! Such “in charge” behaviors make you come across like an insecure bully.

– Fourth, remember you’re the boss and no longer their bud. Yes you can still goof around with them but you must establish that fraternization line and no longer cross it. Do these four things and the transition and relationship should go well.

Tony Danza in Who's the BossWho’s the boss?

It’s going to happen. The person you were just talking to complaining about your boss, the organization, and anything else you can find to gripe about is going to walk in one day and say “I’m in charge now.” You’ll quickly hit rewind to review every confidential peer conversation you’ve had with them to look for things that will put you at risk or on bad footing with your new boss (who used to be your bud and your confidante). This is the primary source of the awkwardness mentioned above.

Get over it. Quickly. They’re your boss. They feel just as weird as you do. The best (and most appreciated) thing you can do is make their transition easy. Give them the benefit of the doubt. Give them a chance to lead. Show some respect. Support them. Make your expectations and needs known and candidly give them feedback when they’re being too much of a peer (wishy-washy) or too much of what they think a good boss is (micromanager). Help them learn how to best manage you for the best results. You need to manage up in this situation and show respect rather than gossip and undermine your new manager. Remember – they were your peer and friend at one point. Treat them as such.

You’re the Big Boss

You have a vacancy you need to fill. You look into the organization and can promote someone into the role but it will create this awkward peer-to-boss dynamic. You can do it but set everyone up for success. Sit down with the new boss and explain your expectations of the role and highlight some of the transition difficulties of moving from peer to boss. Give them ongoing coaching during that period of change. Sit down with the team directly and let them know you expect them to support their former peer and acknowledge the awkwardness. Talk about how you’ll be coaching the new boss to ensure the team members can continue to do an outstanding job. Do your best to facilitate the change through the “weird” period.

Going from peer to boss creates an awkward situation for all involved. Call out the elephant and keep the dialog open and you’re chances for a successful transition go up exponentially.

Mike Figliuolo at thoughtLEADERS, LLC

P.S. That hand gesture at the beginning of the post is the “awkward turtle.”  During an awkward moment, this hand gesture is used to mark the situation as awkward, and, depending on the situation, makes it more awkward or clears the air. The awkward turtle is made by putting one hand on top of the other with the thumbs sticking outward and rotating forward. The speed of the rotating thumbs depends on the degree of awkwardness.

3 Responses to “Making the Awkward Jump from Peer to Boss”

    • Anonymous says:

      I have experienced all three of those scenarios. Without question, the easiest for me personally was being a gboss an promoting one subordinate over a number of his peers. Fortunately the selection criteria had two qualities that made it easier. First, the selection criteria was based in large part upon metrics and this went a long way toward mitigating any disagreement or displeasure. Secondly, the methodologyand weighting for the remainder of the selection criteria was clearly articulated and explained well in advance of the actual selection process.

      The more difficult of the three involved a subordinate who was politically promoted over me. Though I was not pleased, I made the decision to make the best of it. The real problem was my new boss. He well knew how he managed to gain the position and he was constantly trying to prove it was the proper choice. This created a great deal of tension and unnecessary conflict for several years, until he moved on from the organization. Unfotunately, it did not just affect me, but the entire organization. Others could readily see such circumstances and actions and recognized the negative impacts on their work environment. I wish I could honestly say that none of my reactions ever contributed to the situation, but that would not be true. I will say that most such reactions were just that, reactions, and not created by anger or resentment on my part. Perhaps though, some of those reactions may have been better left in the box.

  1. Chuck Hyde says:

    Having lived the experience of manager to director to CEO in the same organization, where our founder’s daughter is a director, I agree with your four points. We transitioned through the awkwardness well and had a lot of similarity to your four points.

    I would add that our success in this transition also had a lot to do with 2 things:

    How my former superiors/peers conducted themselves. They had a choice in how they responded and a lot of credit goes to them.

    What I’d done and the relationships we’d built before the promotion. Credibility and trust aren’t built in a day. If those are strong leading up to the promotion, it sure helps a lot following it.

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