The Greatest Question Ever Asked
“What would it take to send a man to the moon and bring him back safely by the end of the decade?”
When President John F. Kennedy asked this question in 1961, it wasn’t just a bold statement—it was a game-changer.
It forced people to think beyond what they thought was possible, to innovate, collaborate, and commit to a goal that seemed unimaginable at the time. And it worked.
By 1969, Neil Armstrong set foot on the moon.
This is the power of a great question.
It challenges assumptions, sparks action, and turns big ideas into reality.
In your mastermind group, you might not be launching rockets, but asking the right questions can make all the difference.
A well-timed, thoughtful question can help your accountability buddy refine their goals, push their limits, and unlock breakthroughs in their business.
Questions To Stress-Test a Goal
Questions to Challenge a Goal
These questions are designed to stress test the goal and ensure it’s realistic, well-thought-out, and aligned with their bigger vision:
- What does success look like for this goal? How will you measure it?
- Is this goal pushing you enough, or could it be more ambitious?
- What could go wrong, and how will you handle it if it does?
- Have you thought about the resources (time, money, people) you’ll need to achieve this?
- Does this goal align with your long-term business vision? Why or why not?
Questions to Motivate Them
Sometimes your accountability buddy needs a bit of encouragement to reignite their passion for the goal. These questions help shift their mindset and get them excited:
- Why is this goal important to you?
- What will achieving it mean for your business or life?
- What would it feel like to accomplish this goal? How would you celebrate?
- What’s the first, small step you can take to get started?
- What’s one strength you have that will help you crush this goal?
- Who else will benefit when you achieve this? (Family, team, clients?)
Questions to Keep Them Accountable
Accountability is all about staying on track. These questions focus on ensuring your buddy is making steady progress and sticking to the plan:
- What’s your next milestone, and when will you hit it?
- What are you prioritising this week to move closer to your goal?
- Have you done what you said you’d do since our last check-in? If not, what happened?
- What’s getting in the way right now, and how can I help?
- If this goal slips, what’s your plan to get back on track?
Questions to Refine or Pivot a Goal
Sometimes goals need to evolve, and these questions help your buddy decide whether it’s time to adjust course:
- Is this still the right goal for you and your business? Why or why not?
- What have you learned so far, and how could you use that to tweak your plan?
- Are you still excited about this goal? If not, what’s changed?
- What’s the biggest lesson you’ve learned so far?
- How will that impact your next steps?
- If you started over today, would you still set this goal? If not, what would you change?
Questions to Identify Potential Obstacles
These questions help them anticipate challenges and plan accordingly:
- What could get in the way of achieving this?
- Have you faced similar challenges before? How did you handle them?
- What’s your plan if things don’t go as expected?
- Who or what might be holding you back from getting started?
Questions to Explore Their Plan of Action
These questions dig into the how of their goal:
- What are the key steps you need to take to reach this goal?
- What’s your timeline for hitting milestones along the way?
- What resources or tools will you need to achieve this?
- Who can you rely on to help you along the way?
Questions to Measure Progress
These help your buddy stay on track and evaluate how far they’ve come:
- How will you know you’re on track to hit this goal?
- What specific metrics will you use to measure progress?
- Have you reached any milestones yet? If not, what’s the holdup?
- What’s one thing you can do this week to make progress?
Questions to Encourage Creativity and Innovation
These help your buddy think outside the box:
- What’s a different way you could approach this goal?
- What would you do if time, money, or resources weren’t an issue?
- What’s a bold, unconventional idea you could try?
- Who else has solved a similar problem, and what can you learn from them?
Questions to Reflect on Lessons Learned
These encourage them to evaluate and grow from the experience:
- What have you learned from working on this goal so far?
- What would you do differently if you started over?
- What’s one thing you’ve discovered about yourself during this process?
- How can you apply what you’ve learned to future goals?
Questions to Push for Bigger Thinking
These challenge them to dream even bigger:
- If you doubled this goal, what would it look like?
- What would you do if you weren’t afraid of failing?
- What’s one bold step you could take right now?
- What’s stopping you from making this goal even more ambitious?
Our Summary: How to Stress Test Business Goals with Smart Questions
The best accountability buddies don’t just nod and say, “Great goal!”
They ask smart, thoughtful questions that push you to think, adapt, and stay motivated.
Whether you’re challenging a goal, cheering someone on, or helping them pivot, your role is to be curious, supportive, and honest.
So, the next time your accountability buddy shares a big business goal, think like JFK and ask a question that changes everything.
Who knows? It might just be the question that launches them to their moon.
Liked this blog? Check out this next one on How to Be a Great Accountability Buddy in Business.
