Every week in coaching conversations, I ask questions designed to shift someone’s thinking. Not shame them, fix them, or tell them what to do, but to draw something out of them that was already there.
Here are five questions from this week. You don’t have to be a coach to use them. They’re potent, practical, and worth sitting with:
1. What would the hero version of you do right now?
I’ve read hundreds of books, attended more programs, and listened to more podcasts than any single person should. I can tell you this with full certainty: you won’t get what you want until you master the moment. Life isn’t lived in years, months, days, or hours—it’s lived in the present moment. You have only ever been, and will always remain, here in the present. If you are committed to living your best life, simply repeat this question throughout your moments. It is the fertilizer for your growth.
2. Will your current habits carry you to your desired future?
As a coach, my job is to help my clients create radical clarity on their visions and then map their decisions to that future. Habits are decisions we make automatically—without awareness. Unfortunately, many of our habits were chosen for us, not by us. Learning how to identify and install habits is a superpower we all possess. If your answer to the question above is yes, then all you need is patience while things unfold. If the answer is no, then it’s time to program the habit stack you need to create what you want.
3. What are we optimizing for right now?
The assumption a lot of coaches make is that everyone wants the same thing. I’ve found that isn’t true. It depends on the season of life the client is in. Some people are good with the amount of money they make and want more time. Others have the time and want a relationship. Some have both but are seeking better health and energy. Asking this simple question creates tremendous awareness and allows people to view their lives and businesses through a different lens.
4. If your kid owned this business and called you for advice what would you tell them?
It’s amazing how clearly we see the truth when we’re giving it to someone we love. The hard part is offering that same clarity to ourselves. My job as a coach is to help my clients access the wisdom of their heads and their hearts. I haven’t found a more effective way to do so than through the advice we would give those we love, especially our children. We just won’t limit other people the way we limit ourselves. You’ll know what to do if you lean into the courage it requires to act on this question.
5. Have you ever worked so hard to avoid a fear that you accidentally created the very outcome you were running from?
Fear doesn’t just whisper worst-case scenarios, it inflates them. It’s a mental markup, a kind of fear inflation where the cost of the imagined pain skyrockets far beyond the price of reality. And when we buy into that inflated fear, we behave in ways that ironically make it more likely to come true. Fear shapes action. And often, the actions it drives create the very failure, rejection, or outcome we were desperate to prevent.
You can use these for journaling, reflection, team meetings, or the next hard conversation you’re avoiding.
And if you want more like this, check out The Freed Method, a coaching membership for people who want to lead themselves and others better.
live freed,
Jordan
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