How to Improve your Boss’s Leadership Skills

I’ve worked for a growing tech startup the last three and a half years. At Contactually we’re very particular about our culture and we talk about our values. (I’m saying “we” here even though I’m not currently working there anymore.) One of our company’s values is Take Ownership. I still take ownership and act as if I’m an owner of Contactually because I did it for so long, I’m a share holder, and it doesn’t feel right to give that up now just because my life took me in a different direction.) The values are up on the wall and we even award individuals weekly who take actions that represent them. Our CEO Zvi Band, asked for nomination weekly looking for example of those taking actions that represented our values and gave them a mega-huge trophy to have at their desk for the week. I’d have to think Contactually is more focused on culture and values than most, but I’ve purposefully only worked at places that have put an emphasis on values and culture. Even with this focus on values, the day to day practice of getting the work done with people in an office creates conflict. People have different ideas for how to get to the end goal, or the process to use for accomplishing them. Often we end up feeling slighted by someone or we deal with someone in our office that is disrespectful because we fear the consequences of addressing the behavior. It might be cliche at this point to harp on conflict management skills in the work place but I see how it robs workplaces of productivity all the time. If you’re not familiar with Margret Heffernan’s TED Talks on the topic you should give them a listen.

There is one individual I can think of in our office that causes people a lot of internal conflict and puts them under pressure when they work with him. Let’s say his name is Mark. Mark is incredibly intelligent and driven which makes him a great asset for the business. However, because he’s so smart his management style puts people in a difficult position. He’s often so many steps ahead of other people he is always asking questions people haven’t necessarily thought about yet. People who work underneath him don’t feel like they can say, “I don’t know,” to one of his questions. His non-verbal cues make you feel like he’s disappointed with you if you don’t have good answers.

The funny thing about Mark is that he generally has no idea this is the affect he’s having on people. His intentions are pure. He’s always trying to find the best solutions and come to the best answers for how to grow our business. The problem is that he’s analytical mind often takes over and dominates his thinking to the point where he’s not aware of the effect he’s having on other people around him emotionally.

Some of you might be thinking, “How does Bradley know this about Mark?” The answers is I’ve worked as a direct report to Mark and I’ve talked to him directly about this. Initially I thought I just needed to be better. Think ahead more. Impress Mark with how I was thinking ahead just like he was. It didn’t work. It still felt like I was never meeting his expectations. I was in emotional knots about it and decided the only way I was going to be able to deal with it was talking to him about how I was feeling. I knew I was working hard, but I didn’t feel I was doing the right things.

Stop and recognize what just happened in your mind and body when you read the words, “talking to him about how I was feeling.” I’m going to guess a fair number of you had an emotional reaction to that statement. “We don’t talk about the way we FEEL at work! That fluffy bullshit is just navel gazing that doesn’t get us anywhere. I’d never do that, especially with my boss. It would make you look weak.” Let me show you why this is dead wrong.

During one of our one on one’s I got a little vulnerable and said,”I get the feeling that my work isn’t living up to your expectations. What do I need to change to improve.” His reaction was the opposite of what I was expecting. He said I was doing an excellent job and he didn’t want me to change anything. It turned out he was always so focused on the future and continuously improving the business that he never stopped to give positive feedback. He assumed I knew I was doing well. I took his constant future focus on what’s next as me falling short of delivering to the degree he wanted. He saw the work I was delivering as always enabling him to think further into the future for the business, or enabling him to do his job better. The vulnerable step I took enabled us to have a better working relationship but it also had another side effect. Mark, being the reflective, ever improving, awesome person that he is, realized he needed to do a better job of giving positive feedback to everyone that was a direct report to him and started implementing that learning right away.  That vulnerable step I took also created a different kind of trust between us. We both recognized strengths in the other we could mutually benefit from and started asking each other for more critical feedback on how we could execute and lead better.

Here’s what you should be taking away from this: vulnerability shows your authenticity, which leads to trust, and trust leads to accelerated productivity because it multiplies effectiveness across the organization. Frances Fei at Harvard Business School has a great TED Talk about trust, it’s component parts, and how it’s key to evolving our organizations. Can you tell I like TED Talks? Yes, I’m that guy and I’m totally ok with it.

So here’s an assignment for you, the next time you have a one on one with your boss, see if you can move the conversation towards how you’ve been feeling under their leadership. See if you can talk about something you feel you’re not doing well and ask for help. See if you can give them feedback about something they’ve done that didn’t help maximize your talents or abilities. It just might elevate your relationship to the next level and accelerate growth for both of you.

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