10 Lessons I’ve Learned During My Imperfect Leadership Journey

We are all imperfect leaders of ourselves and others. However, along our life journey, we have the opportunity to learn lessons that we can take forward as we become more intentional leaders. Though these lessons were hard at the time, I am thankful for the experiences and the leadership coaching I received that have helped me become more intentional in my style.

Here are 10 of the lessons I’ve had the opportunity to learn during my career.

1. Just because someone is your boss doesn’t mean that s/he has all the answers. Probably not the exact phrasing as it’s been 10–15 years, but this is what I learned: “Melissa, your bar of expectations for me as a leader is too high. I don’t have all the answers. I’m figuring it out just like you.” At the time, this was a serious ah-ha moment, and I’m not sure I loved that answer. It’s hard when you put people on pedestals. As you wear your leader hat, consider that others may think this about you.
2. You can’t prioritize the fun stuff and let the more tedious (though critical) work slide. Sometimes your leadership will reset your priorities for you if you can’t do it yourself. I found myself spending more time on some work that was more energizing for me but less impactful at the time for the organization. My boss made the call to say, “you need to sit this trip out and focus on this critical effort.” I was sad but respected the decision. It was a lesson I needed to learn about really understanding the most critical business priorities.
3. Your stress behaviors are probably more obvious to others than you think. I’ve had several situations where this has come to light, but the one that impacted me the most was when a leader told me, “you look like you’re always stressed/upset. You’ve been given a nickname” (it was not flattering in the least). Wow…that one was hard to hear, but once I got past the emotion of it all, I could see how I could be showing up with those expressions. Though I wished I didn’t have to hear that one, it was critical for me to recognize how I was showing up as a leader, unintentionally.
4. Sometimes it’s not about being right and saying what you think. It’s often tempting to just blurt out what you’re thinking. Early in my career, I did exactly that in a weekly portfolio meeting of our leadership group. I expressed a retort to a leader’s comment that publicly blamed them. Once it came out of my mouth, I knew it was too late to take it back. I was terrified all day that I would be fired while I waited for the opportunity to be able to apologize. I’m still not perfect at choosing my words and timing, but I am definitely more conscious about picking the right words and setting.
5. We would like to believe there’s always a right or wrong answer. Unfortunately, circumstances always play a role, and most of the time, we need to be comfortable living in the gray. I’ve often come down strongly on one side of the decision fence only to then hear more details of a situation and need to rethink my approach. What I thought was black and white was definitely not. We need to be open to revisiting our decisions and being comfortable that there are rarely perfect answers.
6. Just because it seems like the right thing to do and leaders agree doesn’t mean you skip the stakeholder and change management of a new initiative. I was so excited about launching a new program and was confident that our employees would like it though I knew some concerns would be raised. I didn’t do the due diligence needed to better understand how we could address those situations up front. Unfortunately, those details were a bigger deal than I had assumed. I could have avoided a retraction/redo of the program if I had done more due diligence with a broader stakeholder group.
7. You have to be big enough/have the courage to try to fix what’s not working. I spent so much negative energy on a situation where I was sure the person didn’t like me and was purposefully working against me. What a waste of energy because we often agreed when we actually talked it through. Thank goodness they were willing to take that first step because I wasn’t brave enough to do it.
8. I expect a seat at the table, and sometimes, I will not get it. Sometimes, we feel we should be at a leadership table based on our role. Unfortunately, sometimes it’s not a guarantee, and we have to work through how to handle this. When this happened to me, I was initially shocked that they didn’t want or need me to be part of it. I never fully changed this leader's mind, but I built a layer of trust and respect for my work over time. Trying to muscle our way in is not the best solution when the door is not open.
9. Having high expectations for yourself can be good, but it may not always be a fair bar for your team. It’s important to meet your team where they are against that bar and raise it over time. I was often told that my expectations were high for what good/great looked like. I assumed people thought like me, worked like I did, and prioritized as I did. I was wrong, and this bar of expectations sometimes impacted the team's morale because I was pushing too hard. Our desire for a one-size-fits-all approach doesn’t work when it comes to motivating people.
10. Being direct and candid is good, but you can’t forget to express your perspectives with care. The concept of radical candor is so key for this one…you have to care first so that you can be honest with the best of intentions. Making sure that the caring comes out is still often difficult for me in moments of high stress, and that requires that we slow down and be intentional in how we communicate.

Some of these lessons were more uncomfortable to learn, but they have helped me become a different leader. We have to be willing to hear how we’re being perceived. Even if we have the best of intentions, our delivery may not be hitting the mark, so we need to be open to feeling the discomfort of not being a perfect leader for ourselves or others.

I will always be an imperfect leader, but I am much more intentional about how I want to show up as a leader, what I want to be known for and how I get work done through my teams.