Teach your team to execute: Teaching a team to execute is one of the most important roles of a coach. Executing an average idea well is far better than executing a brilliant idea poorly. A good coach quiets the chaos that surrounds many teams, helps them set goals, and holds them accountable to those goals.

The number one leadership initiative in any organization today is improved coaching. Coaching empowers employees, empowerment drives engagement, and engagement drives performance. At its core, coaching is about transformation. Leading distributed teams requires transforming how we coach and changing our play calls and playbooks to get things done. As a part of our interview series called “Moving From Command & Control to Coaching & Collaboration; How Leaders and Managers Can Become Better Coaches,” we had the pleasure to interview Teddy Cheek.

Teddy leads the marketing team at The Escape Game headquarters in Nashville. He and the team have launched 30 category-leading escape game locations across the US with many more on the way. His superpower is building tight-knit teams and helping marketers and creatives improve.

URL: https://teddycheek.com

Thank you for joining us to explore a critical inflection point in how we define leadership. Our readers would like to get to know you better. What was a defining moment that shaped who you are as a leader?

I was asked to lead a marketing team for the first time about ten years ago. I was an Account Manager at a digital marketing agency in Nashville that represents some of the biggest artists on the planet — rock legends and Top 40 royalty. It was crazy stressful — all-nighters, constant client calls, etc. I loved it because it kept me close to music after my own band had failed to make it (yes, I am a Nashville cliché).

I was asked to lead because the two founders of the company were spending most of their time in LA launching our new office and needed someone to lead the Nashville crew. At the time, I had been in my role for less than a year and was excelling as an individual contributor. But here’s the thing — the skills that make a good marketer aren’t the same skills that make a great marketing leader. At the time, I had no idea how different.

Suddenly I was responsible for 25+ high-profile clients and a team of marketers. It was a jarring change, but I did have a few things working for me. Passion — I’ve got it. An insatiable desire to see my team succeed — check. An occasional good-ish idea — sure. But I certainly didn’t have the necessary leadership chops. But luckily for me, leadership is something that can be developed. It’s not something that you were either born with or without.

Over the next couple of years we not only survived but grew our team and client list. As I struggled to find myself as a marketing leader it became apparent to me that it was far more important for me to be a consistent and empathetic coach than a brilliant visionary.

John C. Maxwell is credited with saying, “A leader is someone who knows the way, goes the way, and shows the way.” How do you embody that quote as a leader?

At The Escape Game, our mission and values are the foundation of our culture, which is our most valuable asset. My most important role as the marketing leader is to live out our company values, infuse them into everything our team does, and encourage team members to buy-in to the culture as well. So many leaders put a huge emphasis on team building, fun rituals, inside jokes, and creating a fun environment. They believe it will create chemistry. While those are good things, aligning your team around a set of mission and values, is how you actually create chemistry. Alignment = Chemistry. And leaders can’t create chemistry unless they themselves are living out the company culture publicly and consistently.

How do you define the differences between a leader as a manager and a leader as a coach?

A manager executes what is expected of them by directing the actions of team members and by executing and optimizing processes. A coach grows team members, pushes them to reach their full potential, and teaches them how to win. I believe winning is a skill as much as an outcome.

We started our conversation by noting that improved coaching is the number one leadership initiative in any organization today. What are some essential skills and competencies that leaders must have now to be better coaches?

Most leaders like the idea of coaching but won’t actually do it. It’s scary. It’s uncomfortable. They would rather “hire great people and get out of their way.” That LinkedIn cliche is typically an excuse. It’s the fear talking. Team members need to be coached to reach their full potential. Coaching shows care for team members and their career.

  1. Coaches must be fearless: Great coaches are willing to face uncomfortable situations and have uncomfortable conversations.
  2. Coaches are passionate about their team, not just their own achievements: Great coaches love seeing their team win and grow their careers.
  3. Consistency: Coaching is something you have to do every single day. Saving feedback for a yearly review is lazy, and creates resentment, confusion, and distrust.

We’re all familiar with the adage, “You catch more flies with honey than with vinegar.” How are you inspiring — rather than mandating — leaders to invest in upskilling and reskilling?

Danny Meyer is the founder of Shake Shack and the author of Setting the Table. His coaching philosophy, Constant Gentle Pressure, has shaped how I coach.

Here’s how Constant Gentle Pressure works: Coaching must be constant. Standards must be upheld daily and team members should expect an active and engaged coach that won’t allow standards to slip. Coaching must be gentle. Coach with graciousness and kindness because you care about your team members as people and want them to succeed. Finally, on great teams there is pressure. Most coaches are scared to apply pressure, but the good ones do.

On my team, there’s a lot of Constant Gentle Pressure or CGP surrounding developing expertise and growing skills. Ultimately, I don’t want to work with team members that don’t take personal responsibility for their own professional growth.

Let’s get more specific. How do you coach someone to do their best work? How can leaders coach for peak performance in our current context? What are your “Top 5 Ways That Leaders and Managers Can Be Effective Coaches?”

  1. Buy-in to company culture and expect your team to do the same: If you can’t buy-in to the culture at the company you’re at, leave. Go somewhere else. Culture is the foundation of every good team. It’s alignment around a shared mission and values that creates chemistry which is a vital ingredient in the recipe for success.
  2. Develop team members through Constant Gentle Pressure: Coach your team members every day (constant). Coach with graciousness and kindness because you are on their side (gentle). But also let your team know that there is an expectation to achieve and to produce excellent work (pressure). If you remove “constant” from the equation, you’ll give your team whiplash. If you remove “gentle”, you’ll become a jerk that no one respects. Remove “pressure” and the quality of work will drop.
  3. Require team members to take responsibility for their own professional development: It’s great when companies invest in upskilling, but ultimately team members should be passionate about honing their craft and improving. Professional athletes don’t only practice when specifically asked by their coach. Make it clear that improving is an expectation on the team. If your company is going to grow, the people at the company need to grow.
  4. Teach your team to execute: Teaching a team to execute is one of the most important roles of a coach. Executing an average idea well is far better than executing a brilliant idea poorly. A good coach quiets the chaos that surrounds many teams, helps them set goals, and holds them accountable to those goals.
  5. Appreciate, Recognize, and Encourage your team: Lee Cockerell, former EVP of Operations at Walt Disney World, says that appreciation, recognition, and encouragement are the free fuels that drive human performance. Give these 3 fuels out daily and in large doses. Just make sure that you only recognize things you want replicated.

We’re leading and coaching in increasingly diverse organizations. And one aspect of workforce diversity on the rise is generational diversity. What advice would you offer about how to effectively coach a multi-generational workforce? And how do you activate the collective potential of a multi-generational workforce?

I lead the marketing team at The Escape Game. After hosting millions of players in our escape rooms, I can tell you that the most collaborative teams and the best problem-solvers are multi-generational teams with a diverse set of perspectives. Everyone’s brain works a little differently and teams benefit most when everyone contributes.

To maximize participation, coaches must invite everyone on the team into a big, exciting vision and show them that their individual contribution matters.

You’re referring to emotional intelligence, in a sense. What are two steps every leader can take to demonstrate a higher level of emotional intelligence?

  1. Own their own mistakes: Every leader has made plenty of mistakes in their career. Talking openly about past mistakes and what you’ve learned from those mistakes creates a safe environment for people to share ideas, take risks, and sometimes make their own mistakes.
  2. When you give honest feedback to team members, talk about times you were coached by a leader. How has previous coaching helped shape you into the leader you are now even if it was difficult to receive that feedback at the time?

Words matter. And we’re collectively creating a new leadership language right now. What are the most important words for leaders to use now?

The first thing coaches need to say is “This won’t be easy.” If what your team is trying to accomplish is actually easy, then why would anyone care to buy-in or contribute? If it isn’t easy but the leader acts like it should be, that’s even worse. It’s very demotivating. Acknowledging the challenge and inviting your team to tackle it together — that’s inspiring.

The second thing leaders should say is — “You in?” Once you’ve shared the big challenge, ask the team if they are in. Think back to every heist movie you’ve ever seen. The leader always lays out the wild, nearly impossible plan and then looks across the room and asks “so, you in?” It may seem silly, but asking people to verbalize their willingness to participate invites them to put skin in the game and really commit.

I keep inspiring quotes on my desk. What’s your favorite “Life Lesson Quote,” and why does it mean so much to you?

I love my job, but it isn’t everything. My son is 6 and I am having so much fun being his dad. I constantly remind myself to be fully present with him at home and to make parenting my top priority. I recently came across a LinkedIn post from Jon Acuff that I keep on my desktop.

“You can fast forward childhood but you can’t rewind it.

You can make more money.

You can build more influence.

You can scale more companies.

You can win more awards.

You can achieve more success.

But the years with your kids are gossamer.

They’ll slip through your fingers if your hands are busy chasing things that matter a whole lot less.

Don’t blink.”

Our readers often like to continue the conversation. What’s the best way for readers to connect with you and to stay current on what you’re discovering?

I write about marketing leadership on my blog — https://teddycheek.com. And feel free to message me on LinkedIn as well — https://www.linkedin.com/in/teddycheek/. I’d love to chat with you about marketing leadership!

Thank you for a meaningful conversation. We wish you continued success with your mission.