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Fairly early on in my career, my mentor once gave me the directive “sometimes you have to train your boss.” This was a very direct approach that my mentor described as “managing up.” 

Train your Boss

Days before I was given this piece of advice, I made what I had thought at the time was a “reasonable” change to a particularly significant process at my organization. I discussed this change or exception with a couple of key stakeholders that would be directly impacted. In my mind, the proper communication and collaboration between the stakeholders and myself had taken place. So, I moved forward with this change.

However, my superior did not approve when he learned of my adjustment to this process. A couple of days afterward, he was in his assistant’s office having a conversation when he saw me walking by, “Hamilton!”, he barked. I walked into his office where he diverted his attention away from his assistant and proceeded to sternly reprimand me. He explained I was to do nothing of the sort ever again and that processes had been put into place for a reason. I quickly tuned out his voice as his assistant was just feet away, experiencing a front-row seat to the “improvement needed” tongue lashing. As I patiently waited for the berating to end, my face was red with embarrassment. At the end of his conversation, I could only muster a “yes sir, it won’t happen again.” Any kind of defense or discussion on my part in front of his assistant, I thought would assuredly bring a much worse outcome.

Later that day, I asked my mentor, “I have to confront him about this, don’t I?” I could feel my heart rate increasing. He quipped quickly, “Yep, sometimes you have to train your boss.” He said it like he was reminding me to change the oil in my car, just another maintenance item. But he did emphasize one key point, “just make sure you’re respectful and schedule a meeting. Don’t just walk in his office with this.”

Managing Up

I walked into my boss’ office at our scheduled time and said what I had rehearsed, “I am sorry for going outside of the process and I should have checked with you. That’s my fault.” I continued with a firm and respectful tone, “in the future, you are welcome to bring me in your office, one on one, and blow me up anytime I screw up like that. That doesn’t bother me, but never again in front of an assistant.”

I stopped there. He stared at me for a couple of seconds, but it felt like minutes. “I am sorry about the assistant,” he genuinely lamented. And it was over. It was at that point I was reminded of the fact that he was not just a “superior,” he was human too. He was just as capable of errors and bad judgment, similar to my error in judgment that had brought about the entire interaction.

The concept of “managing up” is what we refer to as corporate world lingo for understanding the dynamics of communicating and interacting with superiors, most importantly when involving hard conversations or disagreements.

There’s a very short, but powerful book called Management Courage by Margaret Morford.  She paints a clear picture of “managing up,” pushing back, or communicating tough items to a superior appropriately, not defensively or disparagingly. Morford excels with this in a chapter called “Take the blame.”

“Managing up” is much easier as long as you respect your superior’s humanity while honestly communicating yours. No one in a leadership position does it right 100% of the time. However, when a superior has crossed your boundaries of respect during an interaction, you need to have the courage to confront the issue in an appropriate, respectful, and confident manner.

Jared Hamilton

Executive Director of HR and People Development

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