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Struggling at Work? Here are Five Ways an Executive Coach Helped Me Tackle My Issues

hertelier has been named a FINALIST in the TravMedia awards, the Oscars for travel publishing. The ceremony takes place in London tonight and to simply be in the mix when the platform is just two years old is...MIND-BLOWING.

An honor even to be nominated, I realize that this achievement didn't happen by chance, and it makes me very grateful to the people who helped get hertelier to this point. Grateful to my partner, Nancy Mendelson, who has been at my side throughout, and especially grateful to you––our readers, our fantastic contributors, and the hundreds of women who have shared their stories!!

On this occasion, there’s another person who deserves a MASSIVE SHOUT-OUT and lots of gratitude…Kathy Hubler, Executive Coach from Ladies Against the Grain. While you may already be a fan of her excellent columns on job search, Kathy is indeed an Executive Coach. We started working together towards the end of last year, initially to help me get more organized, and to help usher hertelier to the next level.

Kathy Hubler Ladies Against the Grain

Why Work with an Executive Coach

Becoming an entrepreneur put all kinds of new challenges in front of me and I knew I needed help. What began as a "pandemic project,” hertelier took off quite quickly and Nancy and I soon realized the platform had the potential to become a viable business. With that, hertelier started to hoover up most of my time and I knew I needed to be more efficient to keep the site growing.

Kathy and I had connected through hertelier, having profiled some of her clients. Then she soon began contributing a few columns about job search techniques for the site, as well. So she seemed the natural choice to coach me, given her background in hospitality. Fun fact: before becoming a resume expert and career coach, Kathy went to the CIA (Culinary Institute of America) and worked in some of NYC’s top restaurants in their heyday–Daniel and Eleven Madison Park–to name drop a few! Her understanding of hospitality environments and issues runs deep.

Be Open to Coaching

Having never had a work coach, though I did do sports through school, it was all new to me. I tend to be a surface skimmer who likes to lean into my strengths––creativity, storytelling, and relationship building. Until now, I could get by ignoring areas I don’t enjoy or feel “good” at. But being an entrepreneur means you have to do it all, even the stuff you don’t like or consider strengths. Annoyingly, you have to attack the problem areas. Luckily, I do love getting advice and opinions (I’m a Libra), so coaching seemed like a smart way to level up.


To get started, Kathy helped me explore my weaknesses and my beliefs around them through a lot of questioning and deep and sometimes uncomfortable conversations. Before our first meeting, she sent me an extensive questionnaire and this was our starting point. Just talking through my fears or things that give me anxiety, helped make them more manageable. Kathy helped me break down these barriers and guided me with possible roadmaps around them.

Coaching is a bit of an Indulgence, But One You Should Justify

I’ve yet to meet a person that doesn’t love indulging in their own issues. The beauty of a coach is you can do this guilt-free, that’s what you hired them to do! Honestly, Kathy seemed to enjoy unlocking each problem no matter how mundane. List building? Task tracking? Daily habits? Nothing was too dull for Kathy. She approached each issue with fresh enthusiasm and encouragement. Also, I found it great to have access to her perspective, which was not mired in any particular outcome.

Meetings Over Zoom

Kathy and I would meet by Zoom for an hour per week over a few months. I had six sessions in total, but there were some holidays in the middle. She helped me set goals and each week I had "homework" following every session. Like everything in life, to get the most out of having a coach, you have to put your whole self into it and do the work!

Everyone is different, and the best thing about an executive coach, and Kathy in particular, is you get to pick what YOU want to work on! I personally struggle with organization and creating systems. I hate that kind of work. HATE IT. So that was my focus for development.

Five ways Executive Coach Kathy helped me the most:

  1. Tackle problems. Whatever the struggle, having a coach helps you raise your awareness and forces you to face them. It’s easy to let problems slide for weeks, months even years…but if you have a coach you have to address them in some way… and be accountable.

  2. Come up with new systems. Running a new business with constantly changing challenges, organization is an ongoing issue for me. Working with Kathy has helped me address that. She introduced me to Trello and offered tips on how to use it. I have since incorporated this into my workflow.

  3. Dig into underlying issues. Although new systems are great, working with Kathy also helped me dig into WHY I struggle with some areas in the first place. We all work differently, and it is important to learn the “why” before making changes.

  4. Realize the Importance of investing in yourself. I am a curious person by nature and great about reading and learning generally, but having a coach made me realize the importance of one-on-one skill-building. I had several breakthrough moments with Kathy. She helped me create the framework and structure for getting sponsors for hertelier. She advised me on systems for tracking and follow-up and helped with creating marketing visions and strategies.

  5. Coaching is a two-way street. I also loved getting to know Kathy better and now consider her a friend! This was an added bonus. Being an entrepreneur can be really lonely and having a coach also helps foster that feeling of camaraderie and connection that I miss from working as part of a team in an office.

Whether hertelier wins tonight, or not, I already feel like a winner. My growth as a businesswoman with Kathy's help has been tremendous. If you have plateaued in your career or have new challenges you find overwhelming, Kathy offers a free 30-minute session. She might be right for you too!

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