The dating game: How to find the executive coach of your dreams

It’s an invaluable lesson that should be credited to my executive coach, Ashira. I can recall our conversation when she first uttered those words: 

I was tasked with developing a strategic plan. Great, I thought to myself. I’ve done plenty of those before. I pulled some samples of past strategic plans I’d developed, passed them along to my executive coach, and asked her for feedback on which she liked best.

It turns out I wasn’t quite as good at writing strategic plans as I’d thought. “These aren’t strategic plans, Jourdan. These are tactical plans,” she explained. “Stop looking at the ground, and set your sights on the moon.” 

Despite all the praise I’d received in the past, it turns out I’d been writing strategic plans inaccurately all along—but I never would’ve known if it wasn’t for Ashira. 

The saying goes: “What you don’t know can’t hurt you,” but what about everyone else? Not knowing is deeply problematic in the workplace—especially in HR. 

If you’re in an executive leadership role, you must get an executive coach. Your leader can help you understand and navigate the nuances of your role, but the CEO isn’t the one to really help you take that feedback and run with it. You need an outside partner for this, someone who will challenge you to elevate your approach, pushing you to become the best version of yourself. 

Mentors assist, but executive coaches elevate 

Executive coaches aren’t mentors. Mentors support, guide, maintain, assist, and help where needed.

Executive coaches elevate, enhance, curate, grow, evolve, expand, encourage you to create, and amplify your thinking.

See the difference?

When I first accepted my current role as VP of People and Places at Karbon, I requested support from an executive coach as part of my negotiation. At the time, it was a stand-alone HR role and I’d be the first person to step into the new position—so I knew I’d need someone to help me navigate through taking this business on a journey it hadn’t been on before. 

I knew this because this wasn’t my first foray into the stand-alone HR world. I’d learned from my mistakes and I knew that an executive coach would help me set my sights steps ahead of where they could be. 

Even the best leaders can’t lead alone.

A mentor wasn’t going to cut it. I needed someone who’d already been there—who’d walked in my shoes, scaled a SaaS company at pace, and knew the landmines that lay ahead. 

Thankfully, Stuart, Karbon Co-Founder and CEO, was already a big believer in the value of executive coaching. He’d had one for years. 

Since I joined Karbon, he and I have worked together to expand opportunities for the C-suite to partner with their own executive coaches. Not only does the program help the individual, but it also keeps groupthink at bay. 

When you’re just starting in your career or starting a new role, a mentor is great. When you’re stepping into an executive role, coaches help you see the forest for the trees and assist you in elevating your dialogue, approach, and strategic vision.

Swiping right and swiping left: the executive coach of your dreams is out there

Finding an executive coach is a lot like dating. Don’t settle. Instead, get to know one another and explore your options. You must date before you ask for their hand in marriage. 

First, know your type  

Before you can find the right coach, you have to know what to look for. An executive coach should:

• Work in your field, but be a few steps further along than you in their career—“they should have seen this movie before,” as Stuart says.

• Have strengths that compliment your blind spots 

• Possess that ‘something extra’ that informs their coaching in unique and engaging ways (for example, my executive coach, Ashira, is also a graphologist)

• Compliment (but not mirror) your work-style

• Challenge you—find someone who is going to hold up the mirror (so to speak) in a way you maybe haven’t before

• Connect with you in an authentic and meaningful way 

• Be vetted by a trusted practitioner in their field—Ashira was awarded HRPA’s Woman of Distinction in 2021

Then, put yourself out there and start your search 

I found my executive coach on LinkedIn, which comes as no surprise to those who know me. As an avid and active LinkedIn user, I’m quick to add a new acquaintance to my network. Some of my colleagues make fun of me for it, but let’s be honest here: that’s what LinkedIn is for. 

My now-executive coach shared an interesting post that popped up on my feed because someone in my network liked it. The post resonated with me, so I checked out her profile. I was impressed with what I saw and decided to reach out. That’s it; it was really that simple!

She and I wrote back-and-forth for a while, exploring the possibility of working together and assessing whether it would be a good fit. We decided to give it a go. 

As a graphologist (in addition to her incredibly impressive HR resume) she asked me to put some words to paper and draw a tree. (Odd, I thought.) For our first few sessions we unpacked her analysis of my handwriting. 

Throughout the process, I felt like she told me things about myself that were in my soul but no one had ever verbalized before. It was mind-blowing—but also quite scary. She takes our coaching beyond just the workplace challenges and takes time to unpack some of the personal things that could have led me to view various workplace matters in certain lights.

It was a definite match. 

LinkedIn is an ideal platform for finding an executive coach, so start there. Scour your feed. Peruse the networks of colleagues you admire. Don’t be afraid to ask for help in facilitating connections. Consult your leader for recommendations.

When you’ve found someone, go on a ‘date’ before you commit. Generate a list of what you’re looking for in an executive coach and ask questions. 

And if it doesn’t feel right, don’t do it! 

How my coach has enhanced my career 

I knew that I needed an executive coach because I knew I’d face great challenges helping a growing SaaS startup to scale. I needed someone who would test my perceived best practices. I needed someone who would question me and guide me through their seasoned lens of professional experience. 

Ashira helps me arrive at my own answers, often through guiding questions. Together we’ve explored questions such as: 

• Why do we do it this way?

• Should we do it this way?

• Is that really a best practice?

• Very importantly, am I being over the top?

Her feedback is rich and our conversations are invaluable. She stretches me to think bigger and aim higher. She’s worked with me on future-proofing our org design, facilitation strategies, and countless HR initiatives.

She’s also chock-full of practical advice, expanding my network and introducing me to new resources. And conversations with Ashira aren’t always high-level—she helps hone in on the details, like providing design recommendations for a presentation deck. 

She also helps to alleviate stress. We all make bad decisions from time-to-time and it can be a relief to chat with someone who can say, “Oh, yeah, I’ve been there, too”.

What are you waiting for?

Executive coaches fill a unique and vital role. Your leader can develop you and support you, but they can’t be your mentor or your coach. They can’t be an objective third-party voice. Executive coaches fill in that gap. 

And if you find the right match, they’ll help you look up and take aim at the moon.