What’s the best question to ask yourself when making a big decision?
In decision-making, it’s tempting to dive straight into solving problems or to take the closest path at hand.
But as Roger Martin, strategy professor and author of Playing to Win, suggests, impactful strategy often requires stepping back to really evaluate what options are in front of you.
Martin’s question - What would have to be true for (X) to be a good option?” - is one of my favorite questions to ask. I use it all the time, not just with clients but in my own life, as well.
I love this question because it focuses less on fixing immediate challenges and more on identifying the core conditions for success. This upstream approach allows leaders to define what success would look like before they commit to action, framing the path forward not by wrestling with obstacles, but by envisioning and constructing the conditions that would make success possible. It’s a subtle shift that promotes clearer thinking, robust plans, and ultimately, more resilient outcomes.
In my coaching practice, I often turn to his deceptively simple yet powerful question:
What would have to be true for (X) to be a good option for you?
Here’s how this question plays out in real-life scenarios:
For Leaders
Innovation Buy-In: What would have to be true for you to get support for your big, innovative idea at work?
Successful Reorganization: What would have to be true for your reorganization plan to succeed?
Scaling Up: What would have to be true for your next round of investment to be more certain?
For Job Seekers
Considering a New Role: What would have to be true for a new job opportunity to be right for you?
Evaluating a Specific Role: What would have to be true for THIS new job to align with your goals?
Presenting Your Value: What would have to be true for YOU to be a good option for THEM?
For Board Searches
Seeking a Board Position: What would have to be true for you to be considered for a board role?
Fitting Board Work Into Your Life: What would have to be true for a board role to fit into your current schedule?
For Fractional C-Suite Roles
Launching a Fractional Practice: What would have to be true for a fractional role to align with your needs?
Attracting Clients: What would have to be true for a client to see value in a fractional leader?
Building Steady Work: What would have to be true for you to secure a consistent flow of fractional roles?
Why This Question Works
Asking “What would have to be true?” goes beyond surface assumptions. It forces us to consider what upstream conditions need to exist and what downstream effects might look like. It also identifies where we may need to gather more information or do more groundwork before jumping into action.
Next time you’re considering a new direction, try out this question for yourself! It’s amazing how often it brings clarity to complex choices.