“Imagine we’re talking a week from today and your week was a success. What made it so?”
When I finish a weekly session with a client, I always ask that question.
I’m listening for 2 things:
1. Their definition of success.
What it looks like, feels like, sounds like.
2. Their priorities.
What needs to go into the calendar, and, most importantly what needs to get deleted.
That single question forces people to choose what actually matters instead of drowning in what they could/should do.
And it’s the same question I lean on every Monday morning when I feel scattered or overwhelmed.
It stops the chaos.
It forces clarity.
It makes me reconsider everything on my to-do list. It makes it manageable and appealing.
But clarity isn’t enough.
Life rarely works on our plan. Schedules blow up. People run late. Unexpected fires pop up. We’re terrible at estimating time things take.
That’s why the second question matters just as much:
“Imagine a week from now you failed at that success. What got in the way?”
Again, I’m listening for 2 things:
1. Patterns of self-sabotage or fragile systems that used to get in the way in the past.
Where things usually fall apart.
2. Awareness that they need better support systems, not more willpower.
And then comes the most important question of all:
“So how can you make sure these things don’t derail your success? What’s the game plan for the messy parts?”
That’s where the real value of coaching begins - designing the safeguards, the tools, the tiny systems that keep success possible even when life is inconvenient, unpredictable, unfair.
Because it will be.
And at the end, there’s always the reminder::
Prioritize what you can control: the reps, the effort, the focused action.
Let life respond how it responds, and learn from it instead of fighting it, which is pointless and a waste of your time.
I ask my clients these questions every week.
And I ask myself the same questions every day.
TL;DR
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What would success look like for you by the end of this week?
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What actions do you need to prioritize to make that success likely?
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What will cause you to fail?
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How can you make failure less likely to get in the way?
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Are you trying to control life, or are you focused on what’s actually in your control, actions?
What are your honest answers this week, dear reader?
