7 Powerful questions to ask when you feel stuck

7 Powerful questions by Cathy Jacob at CathyJacob.com

Can’t find the answer? Ask a better question.

Not being able to see a way forward is different than not having a way forward. Great questions have the power to shift and broaden your perspective. They can point you toward something that is in your blind spot. Or can lead to powerful and even life-altering insights.

In the last 20 years of coaching, the most powerful moments of change and insight have always come after a great question at the right moment. Here are 7 of my all time favorite questions for getting unstuck.

1. What matters most to me about this?

This is a values question. If you’re feeling a profound sense of dissonance, there is likely a value that needs to be honored. Getting to what matters most, also shows you what doesn’t matter as much. This clarity can release you from worrying about the wrong things.

2. What would my future self want me to do right now?

This one is very useful at big life decision points. Think of yourself at different points in the future – two weeks, two years, two decades? How will you feel about this decision point? It can give you perspective on whether the decision is pivotal or trivial. It also invites you to take the long view.

3. What is the view from the balcony?

This question comes from the leadership classic, The Practice of Adaptive Leadership by Ron Heifetz and Marty Linsky. While the future self question asks you to take the long view, the balcony question invites you to the high view. From the balcony, you can lift yourself up and out of your situation to see the full picture. You can see more than you can at ground level. The other advantage of the high view is that problems have a way of looking smaller and less life and death from up there.

4. What’s the opposite of the question I am asking? 

This technique is also known as Inversion. Here’s an example. If you are stuck because all you can see are the risks in moving forward, ask yourself, what are the risks of not moving forward? If you can’t be sure of the right way forward; ask yourself what would be the wrong way? If you aren’t sure what you want out of a decision, ask, what don’t I want? Charlie Munger, Warren Buffet’s business partner and Vice-Chairman of Berkshire Hathaway, was famous for his use of this strategy claiming that many hard problems are best solved backwards.

5. What am I meant to learn from this?

Sometimes we are stuck because we’ve experienced a serious setback. This is a good time to ask what you need to learn from the situation. How might you create a future where this might be something you would be grateful for? Another way to ask it is, “What is the gift in this situation?”

6. How am I contributing to the thing I most want to change?

This has been a powerful question in my life and my coaching practice over the years. When you are asking yourself, “How did I get here again?”, this is a good time to look in the mirror. This question demands that you take a hard AND compassionate look at yourself and your own part in perpetuating this pattern. It requires maturity, honesty, and genuine openness to learn about yourself. It’s not an easy question but if you can stay open, it can lead to incredible personal insight.

7. Finally, one of my all-time favorites, What if this could be easy?

This is the question at the heart of Greg McKeown’s, Effortless: Make it Easier to Do What Matters Most. If you are like me and you tend to make things harder than they need to be, this question should be framed on your office wall. For many of us, the assumption that everything is hard is nothing more than a default setting. This question resets the default and can open us up to a simpler and easier way forward.

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    Cathy Jacob

    I'm Cathy Jacob. I am a writer, coach and co-founder of Fire Inside Leadership. After two decades of coaching leaders on how to inspire while navigating the challenges of demanding careers and lives, I’ve created this site to share the best of what I’ve learned from my courageous clients and leaders in the fields of psychology, leadership, philosophy and neuroscience on what it takes to live an inspired life.

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