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Considering A Leadership Coach? Read This First.

It was the year 2001 and I had just been through a challenging divorce that forced me to rebuild my finances from zero. I was desperate to understand why it happened, and how to deal with my personal feelings of shame and confusion. At the same time, I was catapulting up the corporate ladder in New York City’s advertising industry faster than ever and starting to rebuild my bank account… but questioning everything in my life.

Inside I knew I was ready for a huge leap… and I knew something big was coming. I just couldn’t see what it was or how to get there.

And then 9/11 happened.

The tech crash soon followed.

In a few short months, I found myself out of a job, in the middle of a recession, with no clear direction and no savings.

When life turns upside down, you basically have two choices:

  1. The “Go-it-alone, trial and error, figure it out yourself” route, or the

  2. “Seek support, and learn from those who’ve been there and can show you how” path

In the time leading up to 9/11 and getting laid off, I had learned a LOT and had made impressive leaps up the corporate ladder, but I knew there was something much bigger calling me. Inside, I had a distinct knowing that it was my time to step up as a leader and this feeling like, “It’s now or never!”

I had never invested in “self-improvement” beyond stuff like massages or pedicures and paying for a coach at that time seemed insane. After all, I just lost my job, right? But I knew that I needed to do something radically different in order to see the radical change I wanted.

When I picked up the phone to call my best friend, I was hoping she’d talk me out of it. Maybe she’d tell me I was right; it was crazy, and I could just forget it. It didn’t make logical sense to spend thousands of dollars on a coaching package! I had given up my expensive Park Slope brownstone rental and downsized to a smaller place, but still, paying for a coach was way beyond my comfort zone.

My friend said to me, “Kim, it does sound kind of crazy, but it also sounds like something you should do. I say go for it!”

What my best friend saw was that this wasn’t an investment in my career path, it was an investment in ME. She also believed in me even more than I could believe in myself. (That’s what best friends are for anyway, right?)

So, even though I was afraid to spend the money, I was even more afraid to go back into a field that I didn’t feel aligned with — advertising. I knew it would be going back to the golden handcuffs, and something in me died at the mere thought of that.

I knew I needed the accountability and support and guidance of a leadership coach to really make the changes I wanted to see. I have not been the same person since I said YES to myself in that massive way.

Here are some of the things I’ve done since:

  • Fulfilled my dream of taking a year-long sabbatical

  • Lived in an ashram in India, meditating and studying the science of motivation

  • Co-facilitated coaching workshops in Israel

  • Relocated from New York City to a beautiful mountain town in British Columbia, Canada, where I found true community and wellbeing

  • Become a dual Canadian-US Citizen with two passports

  • Enriched my life by traveling to over 37 countries, many alone

  • Used my leadership coaching skills to grow a digital marketing agency in Canada by 90X in two years

  • Built my own leadership coaching practice that I run from a computer anywhere in the world

  • Coached hundreds of professionals in leadership, resilience, and business development

  • Ran my coaching practice from Bali for 6 months

Hiring a leadership coach is not for everyone, to be sure. Some prefer to stay in their comfort zone, grow little by little, and find their success that way, which is great. That was not my path. I wanted to make huge progress and fast and I knew I couldn’t do it alone.

If you are like I was — you know you’re meant for more, and you’re ready to make a huge leap even in the midst of the uncertainty and crisis — I want to help you find the right support.

Over the years I’ve had several coaches and mentors and I’ve learned (the hard way sometimes) how to pick the one that works best for you.

Here are a few questions to consider when choosing a coach or mentor:

  • Do they have a proven track record of people they’ve helped?

  • Did you trust them immediately?

  • Have they been in business as a coach for a long time? (You define that for yourself, but I’d say at minimum 5 years full time.)

  • Does their expertise fill your skill gaps?

  • Will they force you into their process or encourage you to trust yourself?

When you look for a leadership coach, be sure to find someone who constantly challenges herself and stays out of her own comfort zone. That way you know you’ll have someone who will encourage you to stay out of yours.

Most importantly, you want someone who will not only coach you to find your own answers but teach and share with you what they personally did right and wrong. Because even though you don’t want to suffer the same mistakes, you do need to gain the learning that comes from making them.