When embarking on a difficult conversation, you may fear how it will end up and how the other person will react could derail the progress you need to make. However, leading a powerful conversation with particular questions, and taking specific steps before talking, can set both you and your team up to have a conversation that spawns great ideas.

When you use powerful questions in your conversations, you will help shift focus from what’s wrong to what’s possible. Powerful questions show you’re committed to listening and understanding the other person’s perspective. These questions are framed as open-ended and asked with genuine curiosity.

The Five Steps To Leading Powerful Conversations

The result you will get from a conversation can often be decided before the discussion even begins.

Checking in with yourself and the other person before diving into the core of the conversation can help set the tone for a productive talk.

Take these key steps to ensure you lead your next challenging conversation with powerful questions:

  1. Check-in with yourself
  2. Evaluate the setting and time the conversation will take place in
  3. Get consent to start the conversation
  4. Ask powerful questions
  5. Elicit feedback

Photo By Christina @ wocintechchat.com

Step 1: Check-in With Yourself

Before you start your powerful conversation with someone else, you want to check in with yourself to ensure you approach the discussion with a level-head and no preconceived notions. This essential step needs to happen before you engage with the other person or people in the conversation.

Reflect on if you feel upset about something right now. Even if the powerful conversation feels urgent, you may need first to harness your emotions to be fully present in the conversation.

Next, consider your own emotional distortions. Check-in with your values and filters.

Finally, think about if you change your perspective and see the situation differently without talking to the other person.

Once you have done this and you still want to address and issues move onto Step 2 to lead a powerful conversation.

Step 2: Evaluate The Setting And Time

Now that you feel emotionally ready to tackle the discussion, ask yourself these three questions:

  1. Is this a good time?
  2. Is the place setting favorable for it?
  3. Is the person going to be receptive to it?

Think about the time of day, first thing in the morning, right before lunch, or right before the workday wraps up, might not lend itself to being an ideal time for a complicated, but powerful conversation.

Next, think about where the conversation will take place. Some people prefer in-person talks, some prefer calls, and others prefer emails. For in-person discussions, think about the venue. If all of your conference rooms are glass, pick one that’s not the focal point of the entire office so that you can have some privacy during a difficult talk.

Photo By Mimi Thian

Step 3: Get Consent To Start The Powerful Conversation

Now on Step Three, it’s time to engage with the other person you want to have the conversation with.

First, get consent to begin the conversation, to give them feedback, and to receive feedback.

Here are some helpful phrases to start the conversations:

  • Are you open to talking about this right now?
  • Are you available for a conversation about….?
  • Are you up for a chat about….?
  • Are you in the headspace to discuss this?

If the person replies no, ask, “When is a good time that would work for you?” You want the other person also to feel emotionally centered for the conversation to have the most productive result.

If the person does not know when is a good time, leave it alone. You cannot make anyone grow against their will.

If the other person says yes, then you can begin the conversation.

Pro tip: Don’t start a conversation by asking if you can give someone feedback. It doesn’t leave room for anyone to converse openly. As described in Step Four it’s more effective to ask powerful questions and lead a difficult conversation that includes feedback.

Step 4: Ask Powerful Questions

How you ask questions during your conversation will determine how much helpful information results from it.

Powerful questions will help shift focus from what’s wrong to what’s possible. When you frame your questions in a powerful way, it shows the other person you are committed to listening to and understanding their perspective.

Powerful questions are not statements disguised as questions. Powerful questions yield clarity. Powerful questions are also open-ended and asked with genuine curiosity on your part.

In the next section, we’ll dive into types of powerful questions and how to ask them.

Step 5: Elicit Feedback

To wrap up the powerful conversation, ask the other person for feedback. You can learn a lot here if you give the other person the space to answer openly without feeling guilty.

Elicit the feedback by asking questions like these:

  • What can I do better?
  • How could I have done this differently?
  • What can I do to be a better leader of this group?
  • How could I have acted differently?
  • What am I overlooking?
  • How can I change my delivery?

Create a space to allow your team to safely share their observations, feedback, guidance, and advice based on what they know and have seen. You may need to offer less feedback than you think. Letting people find their own way offers powerful results.

Types Of Questions To Ask In Powerful Conversations

To successfully lead a conversation with powerful questions, different types of questions will help you build understanding, achieve clarity, shape the conversation, and frame things positively.

Remember these questions should be open-ended and framed without bias to be successful.

Build understanding

When entering a difficult conversation, approach it truly believing the other person has a different perspective than you that you can learn from.

Ask these questions to uncover what is important and to shift focus:

  • What challenges are you facing?
  • What is important to you about this?
  • What is the best possible outcome?
  • What did you get out of it?
  • How can you see this differently?

Clarifying Questions

To effectively lead a conversation with powerful questions, the entire discussion can’t be scripted. If you plan the entire conversation ahead of time, you eliminate the opportunity for follow-up that can help you learn more about what the other person faces.

After the other conversation participant shares their perspective, ask these clarifying questions so you can learn more:

  • Where would I find this?
  • When is a better time?
  • Can you give me more detail about….?
  • What is a good example of this?
  • How can I learn more?

Shape options

As a leader within your business, you want to help your team generate new ideas to fix problems. When someone comes up with the idea themselves, they’re more bought-in and likely to execute it effectively.

As a leader, it’s your role to guide them to that solution and you can do so with powerful questions.

Ask these to help generate ideas:

  • What works for you?
  • What options do you have?
  • What needs to happen for this to come true?
  • What is true for you today?
  • What would you have to believe for this option to be right?

Positive inquiry

Finally, you want to end the conversation on a positive and proactive note. After a strong conversation that generated good ideas, you want the team to act on them.

Ask these questions to clarify what should happen next:

  • What do you need?
  • How do you see this work?
  • What works best for you?
  • What do you think about…?
  • How can I help?

Photo by Adam Winger

Why Steer Clear Of The WHY Questions In Powerful Conversations

When you think of how to frame an open-ended question, stay away from starting the inquiry with “why.”

“Why” is not an open-ended question. “Why” is often a way of communicating disbelief, implying something is wrong. When someone hears “why” it can feel like code for “explain why this went wrong.” It has an undertone of shaming and it suggests the idea of finding blame. It puts everyone on the defense and into contemplation.⁠

For example, if you ask “Why did we not meet the deadline?” there’s already a built-in assumption of failure in the question. Or if you ask, “why did you take that route?” there’s an implication that the decision was wrong. Instead, ask something like “What other ways could you have handled the situation?”

“Why” questions can really close down learning because they take us backward. They are past-oriented inquires.
From a coaching perspective, why-questions will not result in strong solutions. ⁠Even worse, when people try to answer a why question they often feel put on the spot they tend to go with whatever comes to mind first, which defeats your real goal. ⁠

Rarely, if ever, is the information someone gives from answering a”why” question insightful or useful because the responder switched to defense.

So how can you frame a “why” question differently? Try these:

  • What can we do instead?’
  • How did you arrive at this decision? Can you provide clarity?
  • How can we improve this?
  • What do we/you need?
  • What makes you feel that right now is a good time to make this change?
  • How can we move faster?
  • Where do you need help?
  • Can you tell me more about…?
  • What is the main focus now?

Photo by Christina @ wocintechchat.com

How An Executive Coach Can Help You Have Powerful Conversations

You can learn how to perfect the art of asking powerful questions.

Asking powerful questions is a skill that can be honed and improved upon. Working with me as your executive coach, we can practice this skill in role plays and implement powerful questions in conversations you have with your co-founders or direct reports.

Over time, you’ll see previously difficult or emotional conversations now result in unique ideas to help your business prosper.


What Are Powerful Questions?

Powerful questions will help shift focus from what’s wrong to what’s possible. When you frame your questions in a powerful way, it shows the other person you are committed to listening and understanding their perspective.

Powerful questions are not statements disguised as questions — they are open-ended and yield clarity. Genuine curiosity on your part is required for powerful questions to work.

What Are The Five Steps To Leading Powerful Conversations?

Try these five steps to lead a powerful conversation:

  1. Check-in with yourself
  2. Evaluate the setting and time the conversation will take place in
  3. Get consent to start the conversation
  4. Ask powerful questions
  5. Elicit feedback

What Are Different Types Of Powerful Questions?

Different types of questions will help you build understanding, such as clarifying questions, shaping questions, and positive inquiry. Avoid “why” questions when framing your questions.