Breakthroughs, Careers, Close Your Power Gaps, Inspiration for Change, Work You Love How To Choose The Ideal Career Coach For You: 8 Questions To Ask Written by: Kathy Caprino

Part of Kathy Caprino’s series “Building a Powerful Support Community”

This month, I heard from a corporate executive (let’s call her “Linda”) who shared her story about a career coach she hired last year. The long and the short of it is that it didn’t end well, and she’s now wary of coaches as a whole. I don’t blame her at all.

This coach turned out to be of zero help to Linda, and in fact, set her back several steps, demoralizing her and leaving her more confused than before.

Sadly, I’ve heard this type of story countless times in the past 13 years in my work a career and executive coach. This coach had Linda take a battery of expensive tests, and the results showed that she was in an ideal job for her interests and skills. The problem was, she’s deeply unhappy in this career of 30 years, and she wants to leave it for a variety of well-founded reasons. The coach also told her that due to her age (she’s in later midlife), she’ll have a very hard time reinventing and finding a new job and suggested not doing it.

Wow, thanks a lot for the motivation and inspiration, sir!

While it’s certainly true that reinventing in midlife has its deep challenges (I know this from experience as I transformed in midlife from corporate exec to marriage and family therapist to career coach, writer and speaker), it is doable if you engage in the process with your eyes wide open and with the right steps, strategies and support, integrating all your new learning as you go.

I had a similar experience back in 2000 with a career coach I hired. I had built a corporate marketing career for 18 years and experienced a good deal of outer success. But as I approached age 40, I experienced some serious crises and challenges (which I now know are common among thousands of professional women) that brought me to my knees, including chronic illness, sexual harassment, gender discrimination, toxic bosses, zero work-life balance, unethical management, and more.

What was even more painful was the feeling that what I did for a living offered no positive, contributive value to the world. It was totally lacking in meaning and purpose for me, and as I turned 40, that began to feel like a situation I could no longer live with.

I had been in these types of high-level marketing roles for a long time, and I had such a longing to change my career and do different work that helped people and offered more personal fulfillment. I dreamed of a new direction, but simply couldn’t figure out what to do on my own, without losing everything that I’d worked so hard to achieve.

After hundreds of dollars’ worth of meetings with this coach, and a series of expensive assessment tests, he shared, “Well, looks like your current job is a great match for you and meets all your key needs.” I was so angry and demoralized at his response and at the wasted time and money. If it met all my needs, why am I so desperately unhappy in this work? Why am I “breaking down” from the stress, exhaustion, crushing competition, and lack of connection to my work?

The reason he concluded that my career was right for me came from his limited perspective and limited ability as a coach. He just didn’t understand that you can hate work that seems to fit your skills, and he didn’t know how to help me brainstorm, flesh out and test viable new directions. He wasn’t skilled in helping me leverage what I was good at and also apply that to a new direction that would be more fulfilling for me.

I did eventually transform my career and move into the helping profession (thanks to a pivotal conversation I had with my therapist after a brutal layoff in the days following 9/11). But what I needed was a real breakthrough – a “paradigm shift” that would allow me to recognize the true value of my skills and experiences and embrace new opportunities and directions that would be a great fit.

How did the coaching process go wrong, then? 

The career coach and assessment tests I took identified my professional needs and talents but the key thing he missed was that while my current work was indeed tapping into various talents and skills I possessed, I was pointed in the wrong direction. The outcomes that my career focused on felt wrong and “off” to me – not positive or helpful to the world.

And this coach missed the single most important aspect of what I wanted in my working life – to feel good, right and proud about work I was doing that could benefit others.

This coach also missed exploring other vital dimensions to a joyful and successful life and career, including:

  • Your standards of integrity – what you will and will not compromise on
  • Your life intentions – what you want to create and achieve by the end of your life
  • Your life purpose – the unique purpose you’d like to fulfill in your life and why you’re on this planet at this time
  • Your natural skills and talents – those talents and skills that have been with you since your early years that are a deep joy to use
  • The outcomes you want to work toward – the projects, initiatives and results that make you proud to be engaged in
  • The type of people you want to work with and the culture you’re immersed in – people whom you admire and respect, and who align with your core values and your definition of positive and helpful
  • The timing of your life right now and what’s a fit with your other top priorities
  • Your financial, geographic and other needs and desires

Career coaches who don’t touch on the above aspects of building a fulfilling career aren’t going to be successful for you. They disregard the most important dimensions of professional life.

But, as Einstein pointed out, we cannot solve a problem on the level of consciousness that created it. We often do need outside help to shift our understanding of ourselves and to see more clearly what we have to offer and what matters most to us.

If you are interested in receiving outside help from a career coach to build a happier professional life, below are 8 questions to answer that will help you vet this coach and make sure he or she can help you shift what needs to change and propel you forward to your ultimate visions and goals:

#1: Do they feel great to talk to?

Talk to the prospective coach for 15 minutes to gauge your chemistry and your fit. Share your situation and get their feedback. Then check in with yourself about how you feel right after the call. Do you feel energized and hopeful, and perhaps a bit “scared?” I’ve found it’s a good sign if my prospective clients feel really excited and inspired by the discussion, but also a bit scared. This typically means that you’re inspired to grow, ready to commit to the process, but part of you is “scared” because you know there will some stretching involved. Feeling a bit scared often signifies that the coach will facilitate your moving beyond your comfort zone (which is essential if you truly want growth).

#2: Do they understand deeply what’s required to transform your career?

I believe that when you want to change careers, it’s best to find a coach who’s done what you want to do in the world. Don’t buy into that myth that the coach doesn’t have to know a thing about what you’re trying to do. That’s false.

For instance, if you want to make significantly more money in your new business, don’t go to a “life coach” – go to a coach who possesses deep entrepreneurial experience, has lived what you’re trying to do, and has had great success in helping others do it.

If you want to transform your career, find a great, experienced career coach who’s also reinvented their own career successfully and has helped hundreds of others do the same. Select a coach who truly understands from a personal perspective the living realities of what you’re trying to accomplish.

#3: Are they offering powerful thought leadership and a proven model for change?

Review their articles, blogs, videos, assessments, webinars, etc. What does their body of work reveal about them? Do you love their website, their LinkedIn profile, their articles, their guest posts, their interviews and media work, and other components of their thought leadership? After watching their videos and reading their material, do you feel like you simply can’t wait to work with them?

#:4 What’s their energy?

Get a sense of their “energy.” Every person on this planet, and every helper that you work with, has their own style, approach, worldview, mindset and energy underlying their work. Make sure their energy and approach is a strong fit with your style and energy.

#5: Is their training strong?

To be in the helping profession and be highly effective at catalyzing change and helping people become more resourceful and resilient in the process, these helpers need to be highly trained and seasoned in their work. Becoming an effective change agent for others requires much more than just a few months of taking an online class or studying a textbook. It takes years of hands-on training, and deep internal and external work.

#6: Do their former clients say great things about them and do those comments speak to you?

Check out what the coaches’ former clients say about working with this individual. Make sure that what they’re saying speaks to you at a deep level and instills confidence in you that this is the right fit for what you need.

#7: Do they know how to work with the deeper aspects of your life, personality and emotions that are influencing your career success?
I’ve found that what holds the vast majority of professionals and executives back from greater success, happiness and reward are actually not “professional” issues at all. They are personal ones. After all, you’re a person when you show up to your profession.

So often, it’s our mindset, beliefs, fears, trauma from the past, childhood pain, lack of confidence and self-esteem and other deeper aspects of our human experience that are preventing us from finding joy and success in our work, or asserting the necessary boundaries and communicating in ways that will protect us from pain and mistreatment. Does this coach understand how to deal with the deeper level of what’s going on in your career?

8: Did they help you in the first 15 minutes?

Finally, in your introductory call, did they offer you great help right there in the first 15 minutes? Do they seem to “see” and get you clearly and understand what you’re experiencing, and echo back that understanding? Is what they’ve shared helpful to you right in the first call? If not, pass.

* * * * *

Getting outside help from a trained coach can be a positive and transformative experience, if you’ve selected the right helper. Don’t shy away from getting the support you need. Just be very selective about who you put your faith and trust in, as you deserve to be supported at the very highest level to achieve the career and professional success and reward you long for.

For expert hands-on career, executive and leadership development coaching, visit Kathy’s Career Breakthrough programs, her Amazing Career Project course, and her Amazing Career Coach Training program, and tune into her Finding Brave podcast.

3 thoughts on “How To Choose The Ideal Career Coach For You: 8 Questions To Ask”

  1. It’s interesting to know that a good career coach will help you to choose a job with the type of people that you want to work with. My brother is thinking about what career to choose, and we are looking for information. I will recommend him to hire a career coach to help him choose the best career for him.

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