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questions to help your team solve problems on their own

9 Questions to Help Your Team Solve Problems On Their Own

by | Jan 2, 2021 | By David Dye, Winning Well |

Help Your Team Become Rock Star Problem Solvers

The more you can get your team to solve problems on their own, the more time you have to do the work that only you can do. This 9 What’s Coaching method works like magic to develop critical thinking and problem-solving skills on your team. It also works as a human-centered coaching tool, to help guide any team member (e.g. a direct report, co-worker, project team member, or mentee) who is working to achieve a specific goal. 

Effective Problem Solving: The Struggle is Real

“David, I just don’t have time. My team constantly needs my help, but I need them to do more and solve problems on their own. There’s so much to do that some days I just want to give up!”

Lynn was a mid-level manager in a mid-sized healthcare company. She’d sought out coaching because the demands of her job were nearly unbearable. Between the needs of her team members and her supervisor’s expectations, she’d been working 60-hour weeks, her health was suffering, and she’d reached the end of her rope.

Have you ever felt like Lynn? If you feel overwhelmed, you’re not alone.

If you ever struggle with feeling like you’re doing your team’s thinking for them and don’t have time to do your own work, these are signals that your team needs help to think and solve problems more effectively.

Hero or Harassed?

Most managers respond to these signals one of two ways: they get upset or they dive in to “help” by offering solutions. Unfortunately, neither response gets you what you want: more time for your work and more responsibility from your team.

On the one hand, if you get upset and chastise your team for coming to you to solve problems, they will stop bothering you.

They’ll also resent you and begin dragging their feet rather than solve problems that need attention. But hey, they’re not bothering you anymore, right?

On the other hand, if you play the hero and jump in with answers, the immediate problems get solved and work continues. But next time an issue comes up, your team still can’t solve problems on their own, and, worse, you’ve now taught them that if things get difficult, you’ll just figure it out for them. Yes, you’re the hero, but say goodbye to your own productivity!

The good news is that there’s a better way.

9 Questions For Better Problem Solving 

When a team member comes to you for help (assuming they’ve been trained and this is a problem they should be able to solve on their own), rather than jumping in with the answer, you have an opportunity to develop their critical thinking and problem-solving skills.

The following nine questions will help you to free up your own time and increase your team’s ability to think and problem-solve on their own.


solve problems on their own by asking these questions1. What is your goal?

Start here to check for understanding and ensure that the team member has a good grasp on defining the problem.


2. What have you tried?

This question ensures you don’t spend time covering the ground they’ve already explored to solve the problem. It also requires your team member to make some effort before requesting help.

3. What happened?

Finish gathering facts by asking them to talk about the consequences of the solutions they’ve already tried. Sometimes just the act of talking about it will help them figure out a new solution.

4. What did you learn from this?

With this question, you ask them to reflect on their experience. Often, the act of examining what happened and what learning they can draw from it will spark a new approach to solving the problem.


5. What else do you need?

This is a check to see if there is additional training or equipment they need. Sometimes your team member will say something like: “You know, if I knew how to use pivot tables, I think I could do this.” Great – connect them to a spreadsheet guru for a quick lesson and get them moving.

6. What else can you do?

Now it’s time to have them generate some new options. When you ask this question, one of two answers usually happens. Your team member might say, “I don’t know” or they might offer some options, eg: “Well, I was thinking I could try option A or I could try option B.”

If they say, “I don’t know,” we’ll come back to that with question #9. Let’s assume for now that they offer some options.

7. What do you think will happen if you try option A? What about option B?

You’re asking your team member to explore the potential consequences of their proposed solution. This gives you insight into their thinking and helps them think through what makes their choices viable or desirable.

If they are missing a critical piece of information, you can supply it here without telling them what to do. Eg: “One additional factor you will want to know is that the customer considers that a vital feature.”


8. What will you do?

This is the critical step that you’ve been leading up to. As you helped them review the facts, reflect on what they learned, explore alternatives, and the consequences of each choice, the goal is for your team member to choose their solution.

When they choose it, they own it. If they choose something that seems to be a clearly inferior option, you can ask them to help you understand why they think that’s their best option. If they don’t understand some of the other issues affecting the decision, you can also add those to the mix.

Enter The Super Bonus Question to Help Your Team Solve Problems

9. Super-Bonus Question

You might be wondering what to do if the person replies to one of your questions with, “I don’t know.”

“I don’t know” can mean many things. Rarely does it mean the person has zero thoughts about the issue.

More often, “I don’t know” translates to:

    • “I’m uncertain.”
    • “I don’t want to commit before I know where you stand.”
    • “I haven’t thought about it yet.”
    • “Will you please just tell me what to do?”
    • “I’m scared about getting it wrong.”

Your job as a leader is to continue the dialogue – to ease the person through their anxiety and train their brain to engage. This is where the super-bonus question comes in.

With one question you can re-engage them in the conversation and move through “I don’t know” to productivity.

When someone says, “I don’t know,” your super-bonus question is: “What might you do if you did know?”

Why The Super-Bonus Question Works Like Magic

The person who was stymied two seconds ago will start to share ideas, brainstorm solutions, and move on as if they were never stuck. It’s amazing and hard to believe until you try it.

The super-bonus question works because it addresses the source of the person’s “I don’t know.” If they were anxious or fearful, it takes the pressure off with tentative language: “If you did know…” Now your team member doesn’t have to be certain or look for your approval and they’re free to share whatever they might have been thinking.

If he or she hadn’t thought about the issue or didn’t want to think about it, you’ve lowered the perceived amount of energy they have to spend. You’re not asking for a thesis on the subject, just a conversational “What might you do?”

Our brains can do amazing work when we remove the emotional blocks. When you do this for your team, you train their brain to engage, to push through their ordinary blocks, and increase their performance. Ultimately, they will be able to have these conversations with themselves and will only need to bring the very serious issues to you.

Celebrate Success

You’ll know you’re succeeding when a team member tells you: “I had a problem. I was going to come and talk it over with you, but then I thought, you’re just going to ask me all these questions. So I asked myself all the questions instead and I figured it out.”

Celebrate those moments and encourage them to start asking those questions of the people around them. You’ve just increased your team’s capacity for problem-solving, freed up time to focus on your work, and…you’ve built a leader!

Does your company need a Courageous Culture – with higher engagement and a results-oriented approach to innovation? Where your employees speak up, share their ideas and drive quality performance and productivity? Check out our Strategic Leadership and Team Innovation page to learn more about our programs. 

Ask Courageous Questions

See Also: How to Provide More Meaningful Performance Feedback

Stop Asking How Can We Improve: New Research Says the Best CEOs Do These 3 Things When Asking For Feedback (CNBC)

Your Turn

Remember, when a team member can’t solve problems, good questions are your best solution.

We’d love to hear from you: Leave us a comment with your questions about this business coaching process or share your best practice for helping team members improve their critical thinking and problem-solving.

The 9 What’s Coaching model is just one of the popular tools in our leadership training programs.  For more information, contact us at [email protected].

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Want more human-centered leaders in the workplace? Share this today!

Want more human-centered leaders in the workplace? Share this today!


  1. Michael Crist

    I love it when common sense and intelligence blends. Empowerment is a strong message. I enjoyed the article. Thank you!

    If you like this article, you might also learn to love Gary Vaynerchuk.

  2. Daniel

    So helpful.
    Great insight

    • David Dye

      Daniel, glad to hear it was helpful. Thank you!

  3. Jay Butler

    My experience is that team members know a lot more than they give themselves credit for. By asking very simple questions, like the ones you have listed gives the opportunity to reflect on past experiences. Another great question is “What has worked in the past with similar situations?”

    • David Dye

      Totally Jay – helping people tap into their own wisdom is great leadership!

  4. Karin Hurt

    Jay, thank you. GREAT addition.

  5. Dave Gregory

    The Super Bowl question “If you did know…” is such a great response to “I don’t know.” One of my best leaders, Dwyer Gruver, taught it many years ago and it’s proven to be very effective over the years. People really do know more than they are willing to share initially for all the reasons you listed. I’ve found people stop saying “I don’t know” when you use the Super Bowl question consistently. The creativity people have when they feel psychologically safe is amazing.

    One caveat when using it, it needs to be sincere. People need to know you are genuinely interested in their thoughts. If they feel it is sarcastic or uncaring, it will not work effectively.

    When executed appropriately, your team will benefit!

    • David Dye

      Dave, so true – as with many aspects of leadership communication, if we’re lacking sincerity, we’ll do more harm than good.


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David Dye helps human-centered leaders find clarity in uncertainty, drive innovation, and achieve breakthrough results.  He’s the President of Let’s Grow Leaders, an international leadership development and training firm known for practical tools and leadership development programs that stick. He’s the award-winning authors of four books including Courageous Cultures: How to Build Teams of Micro-Innovators, Problem Solvers, and Customer Advocates and and Powerful Phrases for Dealing with Workplace Conflict, and hosts the popular Leadership without Losing Your Soul podcast. David is a former executive and elected official. David and his wife and business partner, Karin Hurt, are committed to their philanthropic initiative, Winning Wells – building clean water wells for the people of Cambodia.

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