Lessons Learned from Messy Leadership

In a meeting to review a proposal over 20 years ago, I (as the youngest and by far the lowest level person in the room) spoke up about a concern I had about the proposal.

I quickly found myself cleaning up the mess created in my relationship with my boss. Whether it was leadership or insubordination was a matter of interpretation, as I explain here.

Looking through the lens of 25 more years of experience, I can see there was a lot to learn. If I could go back in time and give myself some advice, here is what I would say:

1.  Decisions are Not Made Based on Facts Alone; They are Influenced by Relationships.

I had missed the significance of the rift between the organizations involved and the leaders of those organizations. Until then, I had written off the breakdowns in relationship between my boss and the CIO as a personality clash, instead of understanding the stories that had gotten them (and their organizations) both so dug into their “us” vs. “them” camps.

It is important to understand both the facts and the relationships if you want to provide the leadership essential to making the best possible decisions. When you understand the story from both sides you are be better equipped to facilitate a more effective working relationship between the two organizations.

2.  Wherever You Are, Know Why You Are There.

I had made a lot of assumptions about why I was attending this meeting, based on my experience in my previous job. None of them matched why my boss invited me or what the purpose of this meeting actually was from his point of view. It was a big mistake to assume things were done here the way they were done “there.”  For my boss, this meeting was supposed to be a formality. I may still have chosen to risk speaking up, but there was no excuse for me to not be aware of why I was there and be awake to the risk and potential consequences.

3.  Understanding the Culture is Important to Being Effective

Whether I had committed an act of leadership or insubordination is a matter of interpretation that depends on the culture of the organization. In a command-and-control environment, the interpretation that I had stepped out of line was likely. In that kind of culture, the expectation is typically that you defer to your boss and never question them publicly, if at all.

In a collaborative culture, if I was invited to a meeting I would have been expected to speak up. Of course, reality is never quite so black and white. Despite the culture, individuals can lean one way or the other, so it is also important to understand the belief system of the people to whom you are accountable.

Ultimately I left the company because the culture was not a fit for me. We made it work while I was there. My boss and I found a way to repair our relationship. There were some truly fantastic people at this company and we accomplished much together. It was these pockets of collaboration that kept me going, but it quickly became clear to me my future was not there.

Image credit: alphaspirit / 123RF Stock Photo


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