Learning to Be Comfortable Being Uncomfortable: The Power of Courageous Conversations

I know it sounds obvious... but a team is a collection of individuals. All with different backgrounds... approaches... struggles... aspirations... wants and needs.

Throughout my leadership journey... some of the strongest... longest lasting and most meaningful relationships with my team members have also been the hardest fought. Not just for me...but for them as well.

A Story...

It was early in my days at Keane and we were growing... taking on new clients and projects. This meant we had to shuffle some of the team leadership around so more experienced leaders could on-board new clients and teams.

In one of these shuffles... I was asked to take on a development/support team for Putnam Investments. It was a very mature team who had been together for a while and my role was to build on the client relationship while they continued to deliver. The leader I was taking over from was beloved by the team and to say they were unhappy that he was taking on something new and I was coming in would be an understatement.

One of the big adjustments for the team was that I was not a life long coder and their previous leader would often roll up his sleeves and help out or work with them to troubleshoot when they ran into difficulties. I was NOT going to be able to do that.

Having said that... the team lead was incredibly strong... knew her stuff... and had the confidence of the other developers AND the client. This seemed to me like the perfect situation... she could shine and play to her strengths and I could help the team shine with my strengths.

As YOU can probably guess... that is not how it went...

Right from Day 1 it was obvious that they wanted their other leader back and no matter what I did... or what I said... they were not going to accept me. This was particularly true for the team lead. She had built up a trust and friendship with the other leader that left no room for someone new... especially me. She was also very influential with the rest of the team and I could feel the tension each day as I walked into our office cubes.

I tried everything I could think of to do some team building and show early wins with them but nothing worked. The team lead had made up her mind that I had to go... and if I did... their former boss would come back and they could all get back to normal.

The Importance of a Courageous Conversation

After several weeks of the "cold shoulder" treatment and weekly 1:1s with team members... it seemed as if things were moving in the right direction with everyone...everyone that is EXCEPT the team lead. Our 1:1s continued to be awkward... uncomfortable... with no signs of thawing.

So... after some soul searching... I decided our next 1:1 I would just lay it all on the line... have a very open conversation and see if we could put an end to the stalemate.

I prepped as much as I could in advance for the conversation. I have to admit I was nervous and emotional thinking about it. I really wanted to make it work but knew that without her support one of us had to go... and that most likely meant me since she was SO critical to the client.

It was many...many years ago... but here are a few things I remember about it:

• I opened with describing how I was very aware that I was NOT the former guy and I would never be. Having said that I felt I brought skills and capabilities that would help us grow and succeed

• I talked candidly about the impact that the team's behavior and her behavior was having on me personally AND on our ability to move forward as a team to deliver effectively to the client

• I also acknowledged that we were very different people and that is what made us a perfect pair to lead the team. She could focus on guiding them technically and I could focus on the client to trumpet our success and win new business (things she admitted she didn't like to do)

• My closing comments were honest and tough to deliver. If she could not find her way to work with me that one of us had to go and that most likely was me. I was VERY CLEAR that DID NOT mean her old boss was coming back. She would be trading me for someone new... and she could start all over again. No guarantee who the next person would be and if she gave me a chance...a real chance... I knew we could be the most amazing duo to ever lead a team at Keane

So... How Did it End?

Turns out honesty and vulnerability paid off and she acknowledged her actions and how much she missed her former leader. I told her I admired him too and that he wasn't far away. She could still spend time with him and he was welcome in our cubes anytime to visit with the team.

She agreed to give me a shot and that she would end the stand off between me and the team. Her demeanor instantly changed and it felt as if a weight had been lifted.

In my opinion... we did go on to be one of the greatest duos to ever lead a team for Keane. I continued to earn her trust and she continued support me... guide me... and be one of the longest standing relationships that I have that also had the roughest beginning.

In Closing...

There were two things this week that brought this story top of mind....

• I attended a leadership training on how to have courageous conversations. As we went through the material it made me smile and reflect on the many conversations I have had over the years... including the one above

• It was International Women's day this week and Facebook reminded me of a post that my friend Joy (aka the team lead) posted a couple of years ago....

I guess I would sum it all up to say... lean into uncomfortable conversations and don't be afraid to be vulnerable. Courageous conversations can make us all nervous and emotional yet the rewards can be numerous both personally and professionally. Who knows... YOU may earn the trust and respect of someone that YOU didn't know was possible as well as learning so much from them in return!

Leadership Questions of the Week for YOU!

• What is YOUR earliest...or most memorable courageous conversation?

• What is YOUR advice or learning for others about how to have a courageous conversation?

• Who do YOU owe a "shout out" to this week to tell them how much they made a difference in YOUR life and career?

Thanks for reading and remember...YOU make a difference!

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