Tips for Entering and Staying with Tough Dialogue

The toughest conversations often offer the most important learning. Sometimes we really need to enter the conversations we work hardest to avoid. Tough conversations can be hard to navigate and risky. So how do we “go there” in a healthy way?

Below are some tips for entering and staying with tough dialogue. Tough dialogue ought not be feared, and can bear gifts to those who dare the journey.

1.       Be genuinely curious. When we don’t want to learn, understand or see the viewpoint of another, we won’t. Enter dialogue with open questions you really care about and with a real desire to deepen your understanding of where the person is coming from and what is behind his/her position. Expect information that may actually challenge your ideas in a healthy way and encourage personal positive growth.  

2.       Don’t enter to “win.” Open and honest dialogue is not about winning a fight or taking sides:  it is about hearing each other, respecting one another’s viewpoints, and believing we can both move to a better place as a result of the interaction.

3.       Talk less, listen more. When we are passionate, especially when the person we are talking to is not as passionate as we are, we can get excited, talk faster and fill more of the time. This can shut the other person down or make them defensive. Watch how much you talk, and know you will learn more by listening. It takes courage to share what we are most passionate about. Work hard to invite people in; help them feel safe; ensure they know you are genuinely curious about their viewpoints. In other words, be quiet.

4.       Use good questions for understanding. Ask open questions to gain understanding: “What do you think about … ?” or “What has been your journey to … ?” Ask digging deeper questions to encourage deeper sharing: “Tell me more about … .” or “You mentioned …, what more can you tell me about that?” Ask powerful open questions: “What would you need to hear or see to have you … ?” or “What would have to change in your work or family to enable you to more fully … ?”  These types of questions (and taking time to truly hear the response) tells the person you are with that you care and want to understand.

5.       Ask head and heart questions. Our beliefs and passions are directly and deeply connected to our heart and our emotions. It is helpful to ask what people “think” about things as well as how they “feel” about them—both will offer insights. Head and heart questions shed light on what they believe and why they believe it. Both are part of who we are as human beings.

6.       Be gentle. Talking about issues we care deeply about and feel strong about is not easy, for either side. Be attentive to energy and know when it is enough for now. If the dialogue was respectful, then seeds have been planted and there will be other opportunities to further our learning journeys.

7.       Prepare yourself. We don’t always know when we will enter tough or challenging dialogue. However, when you are aware this is likely to happen preparing yourself for it is wise. Calm yourself, know deep listening will be needed, and enter the dialogue with genuine curiosity.

8.       Stay humble. We all know and believe what we do because of our personal experiences, education, faith, family and environment. Since this is unique to each of us, it makes sense that our beliefs are also our own. We all have insights to offer others and also have much to learn. Enter with humility and know life is a journey of surprising discovery.  


Entering into dialogue with someone about challenging topics that are important to us can be rewarding. Which of these tips do you find especially helpful?

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