5 Lessons of an Imperfect CEO

I am an imperfect leader.

I work with imperfect leaders of imperfect organizations.

I specialize in helping CEOs of small organizations become more intentional and more confident that the strategies they’re using to bring the right people to the team, put them in the roles that optimize their impact, and encourage them to build careers there are in place to drive growth and impact. 

In December 2022 (full post linked here), I wrote about 10 lessons I learned as an Imperfect Leader, most of which were from my corporate experiences.

I’ll share those highlights and then 5 new ones since I’ve been on my entrepreneurial journey. 

The Original 10

1. Just because someone is your boss doesn't mean that s/he has all the answers.

2. You can't prioritize the fun stuff and let the more tedious (though critical) work slide.

3. Your stress behaviors are probably more obvious to others than you think.

4. Sometimes it's not about being right and saying what you think.

5. We would like to believe there's always a right or wrong answer.

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.

7. You have to be big enough/have the courage to try to fix what's not working.

8. I expect a seat at the table; sometimes, I will not get it.

9. Having a high bar of expectations for yourself can be good, but it may not always be a fair bar for your team.

10. Being direct and candid is good, but you can't forget to express your perspectives with care.

Most of these lessons were uncomfortable but helped me become a different (and hopefully more effective) leader. We have to be willing to hear how we're being perceived. Even if we have the best intentions, our delivery may not be perfect, so we must be open to the discomfort of not being a perfect leader for ourselves or others. 

The Additional Five

1.     Trying to do it on your own isn’t a strength. 

When you try to do it alone, you end up tired and overwhelmed and will have missed the value your colleagues or mentors could have offered. 

I was embarrassed to share when I was hitting a wall.  I was uncomfortable asking people to share an email or a post about a program.  When I started asking, people said yes.  And, when they said no, it wasn’t because they didn’t want to help but because they didn’t have someone to share it with.

2.     If you’re not clear, no one else will be. 

Whether you’re selling an idea, a product or a service, you need to be clear about what it is, what problem it solves, and why someone might want it.  Over the years, I have often struggled to clarify who I wanted to help and how I would do it.  It took some tough love from people who cared for me to go deep and figure out how I wanted to run my business.

3.     Nothing will go exactly as planned. Some things will go better, and some things will fail.  

You can set intentions and create plans but don’t control all variables, so the outcome is never certain. 

One recent example…I thought last year would be a scaling year in business because I saw many positive signals, but many things didn’t come to fruition as I expected.  It turned into a year of introspection that resulted in my personal growth.

4.     More of my time needs to be spent thinking, planning, and reflecting than I thought. 

This is the case for all leaders…it’s not just about doing.  It’s about being able to see around the corners for what’s coming and clear the hurdles that are in the way. 

I have had to consciously focus on being more intentional with my days consciously…blocking time so that I’m not back-to-back, prioritizing time to read and write, and dedicating specific time to work on projects vs. just trying to fit them in.

5.     It’s all about relationships. 

This seems like it should be common sense, but we forget that business is all about the people – how you make them feel, whether they trust you, if they will refer you for an opportunity, etc.  Building relationships takes intentional effort. 

I know I often get too preoccupied with what I’m working on to nurture relationships, particularly those that are newer.  I recently re-listened to Adam Grant’s TedTalk about Givers, Takers, and Matchers. In 2024, I want to be viewed as a Giver in more situations and a Matcher only when appropriate.

I will always be an imperfect leader, but I am 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.

What lesson(s) have you learned over the past year that has influenced you as a leader?