The Nonprofit Leadership Oasis

Learn From My Leadership Mistakes, Volume 2

Jill Fowler, Songbird Leadership Episode 13

We're back with more leadership blunders! In this episode, learn from my leadership mistakes so you don't repeat them.

Connect with host Jill Fowler on LinkedIn and Instagram.

This episode was brought to you by Songbird Leadership -- Amplify your organization's mission through outcome-based executive coaching, strategic planning, and capacity building.

Thank you for joining us today. I’m your host, Jill Fowler of Songbird Leadership.

In Episode 4, I shared some of the leadership mistakes I have made over the years and what I learned from them. Well, those weren’t the only mistakes I made or lessons I learned, so I thought I’d share a few more. 

Very early in my career, I had to fire my good friend, James. James was a really cool guy who made me feel like I belonged when I first joined the team. I looked up to him and respected the heck out of him. Over the years, we became friends, and I really valued our relationship. Sadly, James’ pregnant wife passed away after a brief illness. In the depths of despair, his performance at work plummeted, which was to be expected. Unfortunately, in spite of multiple efforts to support him during his time of grief, he made a significant error that was beyond repair, and he had to be let go. Of course, nobody wanted it to come to that, but it had to be done. And nobody wanted to do the deed since James was well-liked by all, so as the newest manager, I was assigned the task. It was a gut-wrenching conversation and James never spoke to me again after that day. It still makes me sad to think about it.

After that day, I swore I would never allow myself to become close with my coworkers in an effort to protect myself emotionally in case a future termination was necessary. I didn’t like firing my friend and I didn’t want to go through that again. So, for the next 15 years, I was friendly and professional toward my team, but I always kept my distance socially. It was strictly business. Sure, I’d ask about people’s weekends and how their sick kids were feeling. I’d remember birthdays and celebrate anniversaries. But I never socialized with anyone or provided much information about myself. I surrounded myself with an emotional wall and made an effort not to connect with people on a deeper level.

This avoidant behavior seemed to serve me well. It wasn’t necessarily easy or fun to have performance conversations or to fire folks, but because I wasn’t emotionally connected, it became a process to me. 

I went on like this for a while, sort of like a robot simply performing functions without being fully engaged, until I changed jobs and inherited a team of highly social, really wonderful people who oddly seemed to desire to get to know me on a personal level. As a leader, I wasn’t used to the team wanting me around socially. I guess they weren’t yet familiar with the “Jill” method. 

This group fully respected my boundaries, but never gave up their quest to get to know me socially. At this time, I was also in grad school studying leadership. I recall one of my professors discussing resonant leadership and its profound effects on others. I guess the combination of the meaningful educational messaging and the persistence of my team was just the right recipe to get through my thick head. That next week, much to everyone’s shock, I attended a work-related happy hour for the first time. I also started sharing a little more about myself in casual conversation around the office. Both of these things felt really awkward at first, but they provided me with something I was lacking as a leader – connection. 

Now, I still only sporadically attended workplace social functions, and I didn’t overshare personally, but by taking those small steps to help others better get to know me a little better, my already good relationships with my team members truly blossomed. While I always had their respect, what I experienced was next level. I became human to the group. I showed some vulnerability, people identified commonalities we shared, and it built trust and strengthened our team. Work became a little easier for everyone because we had created a deeper bond socially. It was really special.

The next leadership mistake I made was when I created a wellness program for our team. I thought it would be a fun teambuilding activity to gamify our wellness initiatives, so I broke our group up into teams and we had monthly wellness contests. The winning team won a wellness-related prize, such as a water bottle or a healthy lunch of their choice. We successfully held our contests for a few months. During this time, some teams really bonded, and it was proving to be a great experience. That is, until we had our step competition. Our teams were pretty evenly divided when it came to physical fitness, and it was proving to be a close race. Toward the end of the month, my team met to strategize. We decided to do a few things to help put us over the top for that month, including me taking the last day of the month off and walking or running for the entire day until we surpassed our rival teams’ steps. (I’m into ultra running, so this was a fun activity for me.) 

Well, my team ended up winning and each of our team members received logoed jackets. We had a celebration party and life was good…until the other teams voiced their concerns about our strategy. Some said we had an unfair advantage. Others felt we cheated. What started as a fun, teambuilding effort had turned into anything but. And it caused a real social rift within the office, which took a great deal of time and energy to repair.

The mistake I made in this case was getting too caught up in the competition and losing sight of the larger goal of the contest – wellness and teambuilding. I’m generally not super competitive, but in this situation, I was laser-focused on winning. As a leader, one should set the tone of things and make everyone feel included and valued and as though they belong. Instead, I was thinking about myself and my team and winning, disregarding how others experienced the contest. You really need to maintain that global view in all aspects of leadership, whether you’re setting goals, creating a strategy, or participating in a monthly wellness contest, for your team experiences each the same way.

To this day, whenever I wear my logoed winner’s jacket, I think of this story, and it serves as a good reminder of the type of leader I want to be.

My final blunder for today involves me losing my cool. I was sick. REALLY sick. (This was pre-Covid.) I had stayed home for a few days and came into the office just to attend a board meeting. As I was making copies to hand out at the meeting, I heard it. “I’m sooooo busy. I don’t think I can get all of this work done. Nobody is as busy as I am. How is it even possible to have this much work?” It was Christine. Christine’s favorite pastime at work was to loudly declare how busy she was and it drove everyone nuts, because they were all really busy, too. Christine and I had talked about her workload, which was heavy, but not unmanageable. She was doing good work and was able to get everything done with time to spare each day. She enjoyed working with us, she just had just never worked at a job that required the volume of this one. And she was very vocal about it, much to everyone’s chagrin. 

The copy machine was next to Christine’s desk. On the day in question, I felt like absolute crap, and as soon as I heard her start the “I’m so busy” speech to herself, I completely lost it. I responded with a terse, “We’re all busy, Christine, so just deal with it.” Christine fell silent. I quickly apologized, but the damage was done. 

This interaction was extremely out of character for me. I’m known for my even temperament, and I have never spoken like that to a team member, prior to or since that day. But I hate the fact that I did that. If you’re familiar with emotional intelligence, you’ll understand that I had a true amygdala hijacking – an immediate, emotional response that isn’t warranted by the situation. A good leader can keep their emotions in check, even during the most stressful of situations. This can take effort and a good amount of self-awareness to master. And I’m usually pretty good at it, but in this case, I failed. We can’t all be perfect all the time, and this experience had some extenuating circumstances, but it still shouldn’t have happened.

So, the next time you’re in a stressful situation and your blood begins to boil, observe what’s happening, take measures to control your emotions, such as stepping away or doing some deep breathing, and respond when you’re feeling a little more measured. Trust me, both you and your team will be happy you did.

To recap, in this episode, we touched on three important facets of leadership: Showing vulnerability when connecting with your team, maintaining a wide view, and keeping your emotions in check. What can you do in the coming week to work on one of these skills? Write it down in SMART format, put it in a visible place in your workspace, and do your best to honor it. Then, a week from today, reflect on your experience and the outcome, consider how you’d like it to be improved, if at all, and maybe try it again. In no time, it’ll be like muscle memory, and you’ll be performing your newfound leadership habit without even thinking about it.