Are you ready for the Leadership Arena?



Let’s face it – 2020 has been WILD!!!  Work life, home life, and everything in between.  It seems we cannot catch a break from uncertainty.  There have been some BIG challenges for leaders in the last few months. In times like these, we look to our leaders for guidance and support. We look to them so that we know what to do, how to act and for a sense of direction. We all sort of look around to see who is going to be the one to pick us up by our bootstraps and say, “Yes, this sucks right now, but let’s keep going.”

Do those needs and expectations from your team cause you to worry...? 

Do you find yourself questioning your confidence as you say, “we got this”...?

Leaders, you’ve had to encourage your team probably more than ever before. There have been so many changes that it has probably been difficult to keep your team connected with their eyes on the prize. That end goal looks different today then it did on February 28. So you have had to keep talking, reframing the end goal and how everyone is going to get there.  You have had to model the way so that your team could feel, see and believe that everything would, eventually, turn out okay. 

It’s been about 5 months now since our world first shut down. How do you perceive how your team is doing during this time? Are they adjusting? Are some rocking it? Are others floundering? 

No matter how your team is doing, I believe leaders can always get better. 

Better at recognizing shortcomings, better at recognizing strengths, better at communication, better at teamwork…better at creating the culture we want in our company. 

I firmly believe in the 6 rings of leadership and what working on each one of these can do for you and your team. 

Here are some questions to get yourself thinking about the rings of leadership regarding your team:

Self-Awareness: Do you understand your role in the problems/issues? (Hint: If your answer is that you do not have a role, you need to think again!)

Other-Awareness: Do you understand your team members? Their preferences, habits, triggers and how they perceive information and interactions? Are you able to anticipate your teammates’ behaviors?

Communication: Are there conversations you’re not having? Is there free-flowing communication in the form of positive praise and constructive criticism which helps us grow? Or do you feel like you are talking to an empty room?

Leadership:  Are your team members equipped with the tools they need to provide leadership, support, guidance, and mentorship to their people?

High Performance Teams: Is there vulnerability-based trust among team members? Or is there an undercurrent of unease and distrust, preventing important conversations, inhibiting accountability, and distracting the group from focusing on clear results?

Culture:  Does your company’s culture embody the company’s core values and advance its effectiveness?

There’s a famous quote from Teddy Roosevelt called “The Man in the Arena” which has gained renewed awareness through author and researcher Brené Brown. If you have never read it, you need to. It could be the definition of Leadership! There will always be critics. There will always be those that will point out how you have stumbled. The ability to tune those critics out, be true to your values, learn from mistakes, and get back up is what being a leader is all about. But not everyone feels ready for that arena – do you?

In our Leadership Lab 20/20 program (the 20/20 stands for clarity and vision….not this wild year!), I’ve watched professionals come in a bit skeptical, then experience a-ha moments as they explore the 6 Rings of Leadership. They share how they have applied what they learned among their team, peers and whole company. This group of individuals, all from different companies, gets to talk about what holds them back, and how they can move past those blocks and plan to excel. They learn how to be in that arena and succeed.

My prize? I get a front row seat to watch these transformations unfold, see these leaders elevate their capacity to lead, and lift up their teams. AND that is the best freaking feeling EVER. 



Cheyenne Bennett is a Leadership & Talent Coach at Compass Point. Cheyenne developed the Leadership Lab 20/20 curriculum to help leaders focus on self-awareness, communication and healthy conflict. These are skill sets needed to cultivate high-performance leaders and teams within the family business.  Along with being a Certified High Performance Coach, Cheyenne is also DiSC Certified, experienced with Myers-Briggs as well as Gallup StrengthsFinder. Learn more about Leadership Lab 20/20. 

Wondering if Executive Coaching is a better fit for you? Check out our High Performance Executive Coaching program.

Contact Cheyenne at to discuss your vision of leadership.

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