Lonely At The Top

NOTE: This is not a “woe-is-me” tale designed to manipulate and inspire sympathy. This is merely another leadership lesson that I learned the hard way, and that I share in the hope that you will benefit.

One of the most difficult parts about being towards the top of the professional food chain is not having people to talk to. Of course, I have My Chosen Few, and I love and cherish our relationships. However, none of these individuals know my organization on an intimate level or the nuances of my position and responsibilities. I process information by “talking it out”; it’s how I solve problems and achieve clarity in decision-making. It’s a little challenging when you don’t have people with whom you can “talk it out”, due to confidentiality or it simply not being appropriate – I really miss the connection I had with my old team.

As a lifelong extrovert and relationship builder, one of the hardest lessons of leadership for me has been to understand that, as The Boss, it’s incredibly difficult to be a friend AND The Boss. Not because you don’t want to be, but simply because it’s virtually impossible to effectively supervise a person with whom you have a close friendship. Interestingly, during my years as a department director, I was able to maintain exceptionally good relationships with the people who reported directly to me; we were undoubtedly close personal friends as well as colleagues. We used to spent time together outside of work, and these individuals truly were some of My Chosen Few for a long time. I used to joke with them when it was time to do a performance evaluation that I was taking off my “friend hat” and putting on my “boss hat”. Fortunately for me, we had such a bond of trust that my then-team members understood this approach and I was able to have tough conversations with some of them without our personal friendships being affected. As their leader, I didn’t have to look behind and make sure they were still following, because I knew they were there: they were my beloved crew, my squad, my team. They worked incredibly hard to serve our clients and every day I was proud of what they achieved.

I understand now that this is very unusual. It is a rarity to be able to be an effective boss and a true friend. I’m sure there’s a connection to my personality type – I’m a bit of a bleeding heart and I love to listen to others, help solve their problems, provide sincere encouragement and invest in their future success.

[Sidebar – I’m a total believer in the Myers Briggs personality test – yes, yes, I know it’s flawed and reductionist but I’ve been using it for years and have found it to be SO helpful when trying to figure out effective communication strategies and determine why people behave certain ways. I’m an ENFJ, if you’re interested.]

In my current position, I supervise several individuals who at one point were my colleagues and equals. With the exception of one person, I am so grateful that we have been able to transition into our new working relationships relatively easily. I know this is because we had worked together closely for many years and had a strong bond of trust – we believed that each other truly was working for the “greater good” of our organization and our clients. So imagine my shock last week when one of my direct reports came to me to ask why I didn’t trust her. I was dumbfounded at her question, as I was convinced that she knew she was one of the people I trusted the most in the whole organization, not just on my team. My horror must have been clearly visible on my face, because she quickly explained why she felt that way and gave me a concrete example of a time when I did not communicate what she felt to be important information and she felt slighted. Not because she was interested in “gossip”, but because she truly felt she could not perform her job to the best of her abilities without all the pertinent facts. I hung my head, apologized profusely and even sent a card explaining the deep respect and trust I had for her.

I’ve been ruminating on this for a few days. Relationships are hard. They take work. You can’t put them on the back burner for a few weeks because you get busy with your daily tasks, or get caught up in your own emotional needs. The very essence of effective leadership is building AND maintaining professional relationships based on trust. I’ve realized that it doesn’t matter if I feel lonely sometimes – what’s important is that my team members don’t feel alone and that they always have me to “talk it out” with. And the more we work together on problem-solving and decision-making, the stronger our trust will be, and perhaps, one day, I’ll have another team like my old team, another Dream Team.

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