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Pop-Up Coaching Sessions: Why I Offer 15 Minutes Between Regular Sessions

Pop-up coaching sessions are 15-minute conversations my clients can book between our regular monthly or every-two-week sessions, when something comes up that shouldn't wait. I offer them because life doesn't follow a calendar, and I want to be a resource and partner, not just a standing appointment.


What is a pop-up coaching session?

It's a short, focused check-in. No agenda prep, no long lead time. A client has something happening now, and we use 15 minutes to get clear on it.


Here's what clients typically bring:

  • A difficult conversation they're preparing for

  • A better way to present something to their senior leader or CEO

  • A win worth celebrating, especially one tied to what we worked on in our last session


Why do I offer them?

Because the moments that matter most rarely land the day after a session. A hard conversation gets scheduled for Thursday, and our next session is three weeks out. I'd rather be there for that moment than hear about it afterward.


I'll be honest: not many clients take me up on it. But the ones who do get a lot out of it.


What does it look like in practice?


Executive Coach Jeff Stafford with client

One client, a director, was about to present a reorganization proposal to their CEO. Our next session was weeks away. They booked 15 minutes and walked in with a 14-slide deck and a lot of nerves.


I asked one question: "What's the one thing your CEO needs to walk away knowing?" Within ten minutes, they'd cut the deck to six slides and rewritten their opening. They also decided to lead with the decision they needed, not the background. That's the whole point. Small window, real movement.


Are pop-up coaching sessions just a time to vent?

No, usually not. One client asked me this directly, and it's a fair question. But they aren't paying me to listen the way a therapist would. As their coach, I'm helping them create clarity, focus, and action.


Feelings show up, of course. Sometimes a client needs 60 seconds to say what's frustrating them. Then we move. Going back to what I say on my website, success isn't a client saying "that was nice." It's them knowing what to do next.


3 Key Takeaways

  1. Pop-up sessions are short by design. Fifteen minutes is enough to get clear when the question is specific.

  2. They're for real moments. Difficult conversations, high-stakes presentations, and wins worth naming.

  3. They're about action, not venting. Every pop-up ends with a clear next step.


Wondering how coaching could work for you? Explore 1:1 coaching or work with me.


Jeff Stafford is a Minneapolis-based ICF Certified Executive Coach with Orange Slice Training + Coaching, helping leaders and teams grow through Gallup Strengths, EQi-2.0, and Design Your Life. Learn more at OrangeSliceTraining.com.

People. Potential. Purpose.



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