Learn From My Leadership Mistakes

We all make mistakes and I've certainly made some big ones over the years. In this episode, I share some of my more memorable leadership blunders and what I have learned, so you can take steps not to 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.

Transcript

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

On today’s episode, I wanted to share a few of the leadership mistakes I’ve made over the years and what I learned to hopefully prevent you from making them, too. So, let’s get right to it.

I once worked for a really wonderful elder and special needs law firm. Among other things, I was responsible for the firm’s community engagement initiatives. We were going to have a booth at a local pride event, and I didn’t want the firm to come off as stuffy or unapproachable, because that’s not who we were. Plus, who likes to talk to lawyers unless you have to, right?! 

Anyway, I had a beautiful booth planned for the event that would be warm and welcoming. The décor was on point, the people staffing the booth had these great t-shirts from Human Rights Campaign. Our handouts and materials provided some really helpful information. We had a bubble machine and pride flags and candy and music. Aaaand we also had condoms. 

Now, because we wanted to be a fun and approachable booth at the event, these were no ordinary condoms. These were branded “condom pops” – condoms that looked like lollypops. Google it and you’ll see what I’m talking about. They had sticks with a bow that were topped with condoms in every color. They were beautiful – and a fun addition to our booth. The wrapper was clear so you could see the condom inside, and our logo was printed on the wrapper. Oh, and did I mention that our logo was the firm owners’ names?

My work at the firm was largely autonomous and I was given great leeway to pursue initiatives that I felt were a good avenue for firm development. I was left to my own devices, and I liked it that way.  Well, as it turned out, the firm owners were less than excited to have their names on condoms, and I had to throw them away. In fact, they hated them so much, I was forbidden to even donate them! That was more than 10 years ago and it’s still a running joke to this day. At least they had a sense of humor about it.

In this example, I was the sole decision-maker who was very task-focused – I wanted to create a fun booth at the event and show attendees that we weren’t the typical law firm. Unfortunately, that unchecked tunnel vision led to an uncomfortable situation that, unfortunately, damaged my credibility a little.

What I learned from this is two-fold. First, I should have put myself in the owners’ shoes and considered how they might feel about the swag. Instead, I was too heavily focused on the task at hand and completely devoid of any awareness or empathy. Empathy is a vital component of leadership, whether you are leading a team of people or an initiative. It builds trust, enables better understanding, and heightens morale, among other things. So, stop and take a moment to consider how your actions, no matter how exciting or innovative they seem to you, will impact others, and proceed accordingly. It’s a game-changer.

My other leadership takeaway from the condom debacle is that I was too focused on my own agenda and didn’t take the opportunity to collaborate. If I had, not only might the whole situation have been avoided, but we may have come up with an even better idea, one that never would have dawned on me working solo. Even though we were a small firm, several people were very interested in our community activities and would have gladly lent their creativity to the project. I totally missed the boat by not leveraging that resource and the project undoubtedly suffered because of it.

Let me tell you about another leadership mistake I made early on in my career. At the time, I firmly believed that one should keep their personal lives at home and their work lives at work and never the twain shall meet. Boy, was I wrong! Anyway, at the time, I had heard about a concept called the Hook Method that really resonated with young, foolish me. Basically, it’s the notion that, when you get to your workspace, you hang all of your personal needs and feelings and concerns on an imaginary hook and go about your day, thus forgetting about them and focusing on work. Then, when you’re ready to leave at the end of the day, you pick up all of your personal baggage, so to speak, put it back on, and go home. Sort of like taking off your coat in the morning and then putting it back on in the evening.

Well, I liked the Hook Method so much, I thought it would be a fine addition to an upcoming training I was scheduled to lead. Wait, it gets better. On the morning of the training, as I was brushing my teeth, I spied something in my bathroom that I thought would make the perfect addition to my training – the over-the-door hook I used for my bath towel. They always say the best presenters have a visual, so I removed the hook from my door, put it in my bag, and went to work to set up my training.

The training I was presenting was about our organization’s updated policies and procedures, and it was first thing in the morning, so my audience was already super excited to be there. I led with the Hook Method, proudly holding up my bathroom hook as I shared my pearls of wisdom. Needless to say, my message was not well received. And rightfully so.

Today, if you Google the Hook Method, you’ll get lots of content about fishing and crocheting, which is good. There’s no room for that thinking in our present workspace. I’m embarrassed to admit how off the mark I was on this one. For as strongly as I believed in the separation of home and work back then, I believe just as strongly in the notion (if not the value of) showing grace with the overlap today. 

Today’s workplace culture is all about flexibility and fluidity. Your team isn’t made up of unfeeling robots who come to work with laser-focus on their task lists alone. They’re human! And humans can be messy and complicated, and they’ll sometimes bring their fight with their partner or their health scare or their financial concerns to work with them, and you must make space for that if you want to have a long-tenured team with high morale. 

And I’ll take that a step further. Not only should work/home overlap be expected and supported, as a leader, you should also be in tune with what’s going on within your team. I’m not talking about being nosey or knowing too much or any inappropriateness whatsoever. What I mean is that by being genuinely curious and caring and having some overarching knowledge of where your team is coming from, you’ll be better able to make them feel seen, heard, and valued. You’ll be in a better position to effectively communicate with and delegate to them. For instance, if you know someone’s dog died, you might be a little more understanding if an error was made than if you didn’t, which will mean a lot to your team member. It’s interesting to observe that empathy is popping up here, too.

Anyway, of course, work must get done and deadlines must be met and your community must be served. What I’m saying is you can do all of that well while also having some grace with your team. So, expect the overlap of home and work while authentically supporting your team. It’s culture changing. 

While I could go on and on about the lessons I have learned as a leader in the last 30 years, my final example of a leadership mistake for today’s episode was learned when I was doing avian research for a local park district. In that role, I led a team of employees and volunteers in the field collecting scientific data as part of a large grant and community partnership initiative. Those of you who are into science know that protocols are vital. They must be purposefully set forth and rigidly followed. On my team, I took that very seriously, from procedures about proper bird handling, down to the type of equipment we used.

My team’s charge was to capture birds in the field, band them, record data, and forward it to the ornithologist who was in charge of the project. I had a very specific way of doing things that I liked. Everything had a “right” way, such as how the bird bags were secured or what kind of pencils we used, and with good reason. 

One of our volunteers, Phil, was a retired engineer. He showed up every day wearing a utility vest with pockets brimming with every tool imaginable. Tweezers, tape, magnifiers, zip ties – this guy was ready for anything. Phil had a really different way of approaching the protocols of the project than me. I was the blind rule follower. Granted, they were my rules, but still. Phil was always thinking of new and better ways of doing things. Once, he brought three different kinds of lanterns to try out to see which provided the best light for pre-dawn bird collection. Another time, he brought several different kinds of hammers to test which would most efficiently set up our equipment. 

At the time, I was a little frustrated by Phil’s ingenuity. We had everything in place for a successful project. It was tried and true. So why mess with success? Today, I have such a better appreciation for the value of different styles. My way isn’t the only way or the best way. (Well, sometimes it is. Just kidding.) As a leader, by welcoming the differing viewpoints and unique gifts of others, you’re creating opportunity for creativity and the growth of something potentially much better than the original concept. You’re also allowing your team members to take ownership and thrive and be leaders themselves. By the way, to this day, I still use Phil’s preferred lantern and hand sledge when banding in the field.

Phil came to mind the other day when I was in a coaching session with a client. The client was wrestling with how to proceed with an initiative about which I have some expertise. As a coach, I’m a neutral third party who asks meaningful questions in an effort to help the leader chart their own best course of action to meet their goal. The steps this client created to achieve the goal were the exact opposite of what I would have recommended as an advisor, but led to an amazing outcome for her. Simply put, my way isn’t the only and best way, as proven by both Phil and the client. 

These three examples of mistakes I have made over the years highlight some crucial leadership qualities. In short, lead with empathy, foster a spirit of collaboration, meet your team members where they are, and celebrate the unique style and gifts of others. In doing so, you’ll build a lasting culture of belonging and support that will be a sustaining life force within your organization.