How Working With the Right Career Coach Makes for More Successful Leaders

Ansley-working with the right career coach August 23, 2023 By: Kendra Ansley

One association leader shares how working with a career coach helped her manage her goals, advocate for herself and her team, and pushed her toward her next career opportunity.

Five years into my association career, I became executive director of a national association at 27. I was young and untested, but too naïve to know how much I had to learn. I wasn’t overwhelmed immediately, and I was bolstered by a board who were generous—both in giving advice and sharing a kind word.

However, almost three years into the role, it became clear that I had missed some critical lessons that come with time. My team and the association were expanding, and I was increasingly overworked and unsure, all without a peer network to draw on for support.

My board was not made up of association professionals, and my friends and peers were still relatively early in their careers. On top of that, I hadn’t yet tapped into the association network. I knew I was missing something and needed help.

Enter a career coach. My sister had worked with a coach to help her navigate a job change in a complex and demanding field. When she recommended her coach, I didn’t do anything at first. I would have to pay out of pocket, and it wasn’t inexpensive. I also didn’t know at the time I could have negotiated to have my employer pay for this. However, I needed to invest in my own success or risk burning out. Here’s how I went about selecting a career coach.

Finding the Right Fit

The interview phase is critical to having a successful coaching experience. Any coach should set aside this time before you agree to work together. During this call, I shared my challenges and discussed the support I needed.

For me, managing a growing team and an ever-changing and oversized board, along with navigating how to advocate for my team and myself, kept me up at night. I needed someone who had knowledge of similar challenges and could help me build confidence, prepare for difficult conversations, and encourage strategic thinking when I was stuck in the weeds. 

In the interview, Gail shared her philosophies and how she works with clients. Her approach had a therapy-based background and included regular contact. This meant I could share the emotional aspect of the work, gaining tools to manage the feelings and resolve the issue at hand.

We both took time to determine whether the relationship was a fit. For me, having a gentle approach combined with personal and client experiences like my own felt comfortable. We decided to work with each other after that call and still do today.

Being Held Accountable

As a young female, I served a male-dominated industry and had several staff over the years who took my kindness and age as an opportunity to challenge my authority. Gail was not an association professional or an expert in the sector I served, but she shared stories from her former career, as well as the experiences of her other clients who had many of the same challenges.

Our conversations helped me feel less alone—being the leader is an isolating role for which I was not prepared—and give me much needed tools to better manage. Hearing aggregated stories about people in similar roles having similar challenges was comforting.

As I worked through performance plans, asked for more staff to address the growing list of projects, asked for pay increases for underpaid staff, and advocated for my own pay, Gail helped me outline talking points, develop strong plans, and held me accountable for following through.

Without having to follow-up with Gail after these difficult tasks, I probably would have come in less assertive and asked for less than I had planned. Accountability was incredibly important for me.

Guiding to New Roles

Finally, it was Gail who helped me find a new role late last year after nearly six years as executive director. She helped me refine my skills, gave me new tools, and I left my role having many successes under my belt.

One simple practice Gail pushed me to begin was a confidence log—I charted my successes and every time I felt unsure or needed to advocate for myself, I went back to the log. I began to believe in my own capability and then I understood my struggle was not failure, but dissatisfaction in my role. As I realized I needed to make a change, Gail helped me uncover what I want and need out of my career today. This included not only figuring out what I like to do but also the organization and leadership that will help me grow.

Gail helped me overcome adversities that perhaps too many of us are familiar with, and she continues to help me charge forward into the unknown with confidence and tools I am grateful to have today.

I still pay for Gail’s support out of my own pocket, but it has been worth every penny.


Kendra Ansley

Kendra Ansley is managing director at the American Fraternal Alliance.