The Gambler — Agile Coach’s Perspective

Stuart Oakley
3 min readJun 8, 2021

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Although I am not a country music fan, I am aware of this song by Kenny Rogers: The Gambler. One of the teams that I have been coaching lately, really gave me some perspective. Now I have this song raging in my head. To you out there reading this, sorry that you might have it raging in your head now too! 😉

https://www.youtube.com/watch?v=7hx4gdlfamo

You Got to Know When to Hold Them

This is the scenario where you are coaching a team that are really interested in not only learning, but are keenly looking to improve! Teams like this are every coach’s dream.

Know When to Fold Them

Sometimes you are engaged to a team that despite all your efforts, they are not where you want them to be. As much as my stubbornness tries to prevent me, I do have to realize that some people are either just not ready to change or may not be receptive to my personality or style of coaching. And as much as I would like to please everyone, I also need to recognize that I can’t always get through, and I need to be ok with it. It doesn’t reflect on me as a person or my coaching style. What I should do at this state is acknowledge that I have tried my best and it is the people I was working with are not ready for this journey yet.

Know When to Walk Away

Two scenarios come to mind when I think about the “Walking Away” from coaching a team:

  1. The team has reached a level in their Agile journey that you as the coach feel that you are no longer adding value to the team. This is the scenario where I think is the ideal scenario: You have coached yourself out of a job! This is a good thing and you should feel proud of the fact that you have given your all and the team appreciates your efforts. It is here that the mother bird can feel comfortable that her chicks have to the skills to survive and even flourish!
    The important thing I always leave with teams that I have coached is that they are still always able to reach out to me to chat or even work through a problem so that they never feel fully left on their own.
  2. The other scenario that comes to mind is when you feel the team is in a state where they have either reached that false plateau or they’re not realizing the need for coaching. It is here that you can choose to walk away with the hope that at some point in time the team will realize where they are and want to do something about it. They might reach back out to you or they might reach out to another coach.

Know When to Run!

This is where I find myself with one team. A good friend of mine and former co-worker, Frank posted: THE COACH’S DILEMMA, which got me really thinking. When you have a team that is not only struggling with their journey, but you hear crickets chirping when you offer thoughts or insights, do you run, or do you “exercise mollycoddling or tough love?” This is where Frank very effectively stated: “And, if there is no desire where they are, then maybe it’s time to pause or leave.”

Coaching is an Art

Like any knowledge work, it takes experience and tenacity. There are many different types of coaches out there and also there are many difference styles of coaching. This blog post was meant from the coaching perspective, but you can very easily relate this song to stakeholders, teams and leaderships as well!

Stuart is an Agile Coach, ICAgile Authorized Instructor, Educator, Conference Speaker based out of the Greater Toronto Area in Canada. Constantly looking to build his Alphabet Soup of certifications. An active member of the Agile Community and Founder of the Halton Agile/Lean Network Meetup Group.

If you want to find out more about Stuart and Useful Change, please check out:

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Stuart Oakley
Stuart Oakley

Written by Stuart Oakley

Stuart is a Business Modernization Expert, Agile Coach, Accredited Kanban Trainer (AKT), ICAgile Authorized Instructor, Professor, and Conference Speaker

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