The Gambler in Agile Coaching

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The Gambler in Agile Coaching

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For some unknown reason, I was thinking of the Kenny Rogers song, The Gambler, the other day as I pondered some of today’s challenges in agile coaching. Here’s a famous excerpt from the song—

You’ve got to know when to hold ’em
Know when to fold ’em
Know when to walk away
And know when to run
You never count your money
When you’re sittin’ at the table
There’ll be time enough for countin’
When the dealin’s done

And I began to think how applicable these lines were to working as an agile coach. Yeah, I know, but I had some free time on my hands…

Here’s what I came up with.

I think of this as sticking to your instincts regarding our coaching. Perhaps being a bit more prescriptive with your clients or pushing a bit. This might also be the arena of radical candor, crucial coaching conversations, or asking tough questions.

This is when you need to pivot. Either experiment with something new or drop a tried-and-true approach for something out of your comfort zone. I think of coaches who are stick with one tool in their toolbox; this is that point to learn new things.

We’re not always the best coach for everyone. Sometimes one of the best things we can do for our clients is to leave them. Either at the beginning, knowing there isn’t a sufficient match, or when we’re no longer needed.

Sometimes we need to accelerate our departures. One example that comes to mind is ethical dilemmas or conflicts. Another is realizing that the client’s goals or objectives have significantly changed beyond your agreements, capabilities, or desires.

I equate this to being revenue-driven over client-service-driven. At some fundamental level, our coaching prime directive must serve the client over anything else we might focus on. Put another way, staying centered in our coaching presence and mindset.

Finally, I think of this as the reflection of closing an agile coaching relationship. Sure, you might want to invoice or otherwise look at the financials. But you should also reflect on your client impact and any improvements for your future coaching. Going through a personal retrospective, if you will. 

Kenny, thank you for the sage wisdom in this song. Now, while I’m not a gambler, I know when it’s time to run…

Stay agile my friends,


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