The New Must-Have Skillset for Business Leaders

(Disclaimer: Hey Fitness People! To avoid any confusion, when I use the word coach in this context I’m talking about the umbrella term for any professional who guides and instructs and not specifically a personal trainer or fitness coach. Cool? Disclaimer over.)

Coaching often gets a bad rap these days, and it makes sense. There are life coaches, business coaches, career coaches, executive coaches, relationship coaches, fitness coaches (the list could go on) and it’s hard to tell what is useful and what is totally bullsh*t. And to be fair, there is lots and lots of bullsh*t. 

The coaching industry is relatively young. It’s still the wild west where anyone can call themselves a coach, which leads to a field of professionals that are nearly impossible to differentiate. 

While this isn’t an article about how to find a great coach (I’ll write about that soon. Pinky promise!) I am here to make the case to you that coaching as a craft is something every business leader should learn.

I’ll go further to say that in the next 5-10 years business leaders who are not proficient in coaching skills will be forcibly ejected from the workforce.

Seriously. I mean it. 

We no longer live in a workplace culture that accepts old-school methods of management and leadership where bosses can run around the office barking orders, making people cry then asking them to leave their feelings at home. “It’s not personal, it’s just business” is no longer a mantra that this or future generations will tolerate. 

Work is personal. Many of us give our lives to work, spending more time with colleagues than we do with family and friends. So isn’t it time we stop pretending there is some great wall between our work selves and our personal selves? It’s not true and it’s not helpful. #stoptheillusion (<—- I’m low-key starting a revolution here. Haha.)

As Millenials have taken over the workforce (56 million of them as of 2017) they have brought with them a perspective that work is personal and they demand to bring their full selves to work every day. They demand that their work be fulfilling and that bosses are not dictators — instead wanting bosses to be collaborators, mentors, and coaches who help them succeed. 

In short, the workplace is becoming more human. 

At the same time, our robot overlords are slowly gobbling up all the jobs that can be boiled down to zeros and ones. Our workplaces are (by necessity) becoming more steeped in creativity, collaboration, and critical thinking. Ask any artificial intelligence expert and they’ll tell you the last jobs that will be taken over by robots are jobs that require the three C’s I just mentioned, plus other uniquely human traits like empathy, compassion, humor, and trust-building. 

Those skills are, by and large, coaching skills. The skills needed for leaders to thrive now and in the next 100 years are coaching skills. 

A great coach does three things. They help others clarify their goals, overcome obstacles, and hold them accountable for consistent action. How much better would your work life have been if all of your bosses were experts in those three skills?

Listen, I know I’m biased here. I’ve been a Certified Professional Coach for the past seven years and done thousands of hours of coaching work with clients. But here’s what I know… 

Becoming a coach has been the single greatest thing I’ve ever done to improve myself as a leader.

Now, I’m not going to turn you into a competent coach with just one article. Hell, I couldn’t do it in 100 articles. It takes loads of practice. But I guarantee that if you take time to master Our Ultimate Coaching Conversation Cheat Sheet below you will see immediate benefits in your work. 

Let me tell you what this cheat sheet is all about. This handy outline gives you a roadmap for virtually any coaching conversation — any conversation where you want to help someone else clarify their goals, overcome obstacles and commit to action. 

If you simply follow the seven steps when working with other members on your team you will more quickly build trust and rapport, create more collaborative relationships, and help people get unstuck faster for better results. 

Without knowing anything else about coaching you can start using this cheat sheet right away. I’ll walk you through the seven steps briefly, then I encourage you to download the cheat sheet and start using it in your conversations right away. 

Let’s dive in. 

Click Here to Download the PDF

Step 1: Get Started

  • What would you like to talk about today?
  • Where would you like to start?
  • What’s on your mind?

Your first step is simply to get your coachee talking. Start by asking an open-ended question to let them know you are here for them and on their agenda. 

Step 2: Identify and Explore the Core Issue


  • What do you think is the core issue?
  • If you had to guess, what is the underlying challenge here?
  • What does your gut say is really going on?


  • What makes you think that is true?
  • Where does that idea come from?
  • How long have you felt like that was true?
  • What else could be going on here?

In Step 2, you are working to uncover the core issue at hand. While there might be multiple issues at play, your job as a coach is to excavate the single greatest issue from all the rubble, dust it off and help your coachee examine it. 

A key mindset for you as a coach must be one of curiosity. Your role in this coaching process is not to be a problem-solver but to ask great questions to help your coachee solve their own problem.

Step 3: Identify and Explore the Core Feeling


  • How does that make you feel?
  • When this happens, what are you feeling?
  • What did it feel like to be in that situation?


  • Where do you think that feeling comes from?
  • When did you start feeling this way?
  • Tell me more about that feeling.

At this point, you’ve identified and explored the core issue, now it’s time to unpack how your coachee feels about that issue. Don’t skip this step. Talking about how the issue feels is often a key component to understanding it and finding the next best step forward. 

In this step, you might consider normalizing or validating your coachee’s feelings with phrases like “It makes perfect sense you feel that way because…”

Step 4: Define the Cost of Action and Inaction

  • What would happen if you do nothing?
  • What does the current situation cost you emotionally?
  • How would it feel to take action on this today?

In Step 4, you are now clear on the core issue and feeling. This is the moment to explore what’s at stake. What would be the consequences emotionally, practically, financially, and so on, to taking action or not taking action?

Taking inventory on what’s at stake can help to provide some valuable perspective. 

Step 5: Create a Vision of an Ideal Outcome

  • If you had a magic wand, what would happen next?
  • What is your ideal vision for how this turns out?
  • Imagine that you wake up one day and this problem is resolved. Walk me through your day and how it will be different. 

This might be my personal favorite step. In Step 5, you are helping your coachee imagine a vision of future success. It’s hard to overstate the power of vision-building. What separates humans from most other species is our ability to see in our minds possible future scenarios. It allows us to rehearse potential decisions before we have to decide. 

We’re hard-wired to constantly be dress-rehearsing future threats in our mind, that’s easy and it serves some obvious evolutionary benefits. However, dress-rehearsing success in our minds is much harder. It’s not as natural, so a coach can be an incredibly helpful facilitator of this experience. 

Step 6: Explore All Possible Solutions

  • If you had to take action today, what would you do?
  • What are all the possible paths you can take?
  • What would “future you” say is your best course of action?

Step 6 is designed to get all the ideas out on the table. Once your coachee is clear on the core issue and how they feel about it, what’s at stake, and what their ideal future might be, this is the moment to make sure no stone has been left unturned. 

Your job as a coach here is to help your coachee explore every possible perspective. 

Step 7: Create S.M.A.R.T. Action Steps & Accountability

  • On a scale of 1-10, how ready are you to take action?
  • What do you think you can accomplish in the next week?
  • How would you like me to hold you accountable for that?

The final step of every coaching conversation is to help your coachee define an action step and agree on how you will hold them accountable for following through. 

A S.M.A.R.T. action step is one that is Specific, Measureable, Attainable, Relevant, and Time-bound. That means “I’m going to think more about it” isn’t an action step. Your role as a coach is to dig for the most specific version of the action step possible and define a clear method for following up with your coachee to ensure it’s done. 

Accountability can simply be “I will ask you about this during our meeting next Wednesday.” or “Are you open to emailing me when you finish this task on Friday?”. 

That’s it. Boom. You did it! Bravo!

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Now take a deep breath, and go do it again. Practice makes permanent! 

?Click Here to Download the PDF

I invite you to give this cheat sheet a try.

If you simply follow the seven steps when working with other members on your team you will more quickly build trust and rapport, create more collaborative relationships, and help people get unstuck faster for better results. 

Comment below or email me once you’ve used the cheat sheet in real life. I’m here to help and answer any questions that pop up!

Happy Coaching!

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