How to Assess Your Leadership Skills - jennwhitmer.com

Oct 7, 2022

How to Assess Your Leadership Skills

Years ago, I sat at a new-to-me-but-actually-old desk, wondering,
“Can I really do this job?” 


I wasn’t worried about the tasks — training the trainers, creating schedules, talking with stakeholders, keeping records — I was worried about me dealing with all the people issues that come with a leadership role.

I was excited about moving up, but also mildly terrified of leveling up. All the what-if, doubting questions were paper-cuts to my confidence.

Then I got into the thick of it. I felt like no one understood what I meant when I sent emails. I felt judged by my different experience without the “right” degree. I felt like I couldn’t make any mistakes because it would all come crashing down. As you can imagine, exhaustion, overwhelm, and waves of loneliness followed.

My work as a school leader was deeply meaningful. I wanted to succeed, but really I wanted to lead well so the faculty, the students, and the community thrived. And could there be a way that leading felt energizing and not draining?

All the confidence and joy felt elusive — until I had the mac-daddy of all revelations about leadership: it starts with me. 

All the people-issues and problem-solving and vision-casting and teamwork doesn’t happen if I don’t do my own personal and professional development. I had to lead myself first, and then I could lead others.

And I’m here to tell you: all of those leadership skills are attainable for you. You have to do a little investment in yourself.

Make it concrete.
It’s easy to get overwhelmed with all. the. things. swirling inside your head. To start growing as a leader, you have to get it out of your head and into a framework that shows you where you are as a leader.

Assess your location.
Once you have a framework, you need to assess your skills. Is your ideation communication strong but your follow-through weak? Or do you have incredible attention to detail, but little patience for others’ flexibility? You need a shame-free way to observe yourself.

Take the next small step.
We all have areas to work on. But which one first? AHAH! It’s easy to get paralyzed by choices and decisions. You need to choose the ONE next step to improve as a leader.

I was struggling trying it all on my own. A tornado of exhaustion, fear, and overwhelm led me to overwork and weariness. I wanted wholehearted joyful work again. I needed to look at myself, and see what skills needed work (and which ones were helping me!)

The process of investing in myself transformed me. I had boundaries again. I could manage the demands of work. My communication improved. A lightness and energy returned.

That’s what I want for you. What would it feel like to get energy from your work? To feel skilled at handling the people issues and demands coming at you? And most of all confident you are on the right path to help you and your team flourish.

Here’s the catalyst that will impact your growth as a leader. Choosing the next step.
And I’d love to help you.

Book a Spark Call with Jenn.

I will walk you a short process to take a look at what’s working and what isn’t, uncover the most pressing problem that’s keeping you stuck, and identify what’s next for you as a leader. Isn’t that worth 15 minutes?


You may be sitting at your very own new-to-you-but-actually-old desk, wondering,
“Can I really lead?” 

I promise. Yes, you can.

Book a Spark Call now.

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