I was leading a training session this week as part of a yearly retreat and one of the topics we covered was how to have better conversations that might not be comfortable or easy. In all the work I do — helping leaders be better leaders, improving interpersonal relationships, coaching others to make a positive difference in the world on important causes they care about — navigating difficult conversations is an essential skill and an important catalyst for positive change.
Before going into an important conversation, consider what might derail it. What are your own personal comfort zones, subconscious fears, and reactive patterns that might impede open and generative dialogue? Are you hesitant due to the fear of hurting someone’s feelings? Are you worried they will get angry with you? Concerned that things will feel awkward?
The funny thing is, not addressing issues can often create the exact outcome you didn’t want to happen. For instance, avoiding a conversation so that everything feels harmonious, may result in even more difficulty and discord if it’s left to fester. If you fear the relationship will suffer from a frank conversation, often the unspoken tension or resentment emerges even more when things are left unsaid.
Here are some tips to have successful crucial conversations:
1. Think about the desired big picture outcome and purpose
Reflecting on the underlying motivation and purpose and imagining what success will look like following the conversation (i.e. the North Star) empowers you to approach it with intention and authenticity. This will serve as a framework for the conversation and it can also help you stay connected to why you’re even having the conversation so that any short-term discomfort will be worth it in the end.
2. Set the Conversation up for Success
Consider the environment, timing, and mindset that will really help the conversation go well. Make sure you have the space and time to actually have a proper conversation rather than squeezed between meetings. Perhaps meet in a new and soothing environment instead of in one of your offices. Enter the conversation with the best mindset: meet when neither of you is rushed rather than on a day when one of you is preoccupied with meeting a deadline or an important presentation. Be mindful of communication styles. For instance, some people need time to process things before responding so you might need to have two separate conversations with time to reflect in between. Make sure both of your needs are being met so you can have the most productive conversation.
3. Be Open and Curious
Curiosity is a powerful practice. Simply put, when you’re curious, you’re not being judgmental. And you’re indicating to the other person that you are really interested in their perspective and what they have to say. And true curiosity in this context is not the same as being analytical. There is a time to evaluate information and figure things out, but in a difficult conversation, the person in front of you is more important than the details of the content. True curiosity is the desire to explore, discover and learn. I find tapping into the words ‘wonder and awe’ help me shift my energy into curiosity.
4. Use Questions That Start with “What?” Not “Why?” and “How?”
Why and How questions are perfectly good questions for getting to the root of things and figuring things out, but they are not as effective as What questions are for creating more open conversations, especially difficult ones. For instance, Why questions, when directed at an individual and especially in a difficult conversation, tend to narrow the conversation, invite them to justify their position and also at times create defensiveness. How questions also narrow the conversation and put everyone into an analytical state. Instead start with questions like: What are you hoping for from this partnership? What are the benefits you want this to create? What are some of the conditions you considered when making that choice? What would success look like if we went forward in this way? What is it that you want me to know that you don’t think I’m seeing? The possibilities are endless.
5. Seek to Understand Before Seeking to be Understood
Listen first. Most of the time we go into a difficult conversation being impatient to tell them our perspective because we think that if they only knew what we knew, surely it would all work out. Instead, if you listen first, they will feel heard, and will also be more likely to listen to you. It also means that you may change your mind once they tell you their perspective (and you must be open to this). And listening doesn’t mean waiting for your turn. It means truly being curious and trying to see their point of view.
6. Use building language
Using language like “yes, and…” (instead of “No, but…”) or “what I like about that…” (which is not the same thing as “I like that”) or “building on that….” allows the conversation to be generative and build on each others’ ideas. It will feel less confrontation and more aligned and more like you’re on the same team trying to get to an outcome that works, rather than against each other. No matter how much you disagree with someone, you can always find at least 5-10% common ground. This really helps in difficult conversations.
7. Intent and Impact
This is a tricky one. We used to say “assume positive intent” about the other person because sometimes we can make up a whole bunch of reasons why people act the way they do when often it comes down to different styles, perspectives, and reactive behaviors’. So yes, intent does matter. I personally give a little grace when people are genuine with their efforts. But impact matters even more. Just because you didn’t mean to have the impact you had, you still have to be responsible for it. This is even more essential when considering diversity, equity and inclusion. The more you present to the world in the privilege of what society and systems generally support, be aware that you will have blind spots about how others perceive your words and actions. If you present to the world in any of the categories of white, male, cis, heterosexual, non-disabled, or neurotypical you definitely have blind spots about your impact. Keep this in mind when approaching difficult conversations and be open to listening just a little bit more.
There are many other things you can do, but these techniques really serve to make difficult conversations just a little bit less difficult. And the benefit is, these techniques will help all of your relationships and conversations.
Effective leadership necessitates the ability to navigate through difficult or uncomfortable conversations. It’s natural to feel discomfort when faced with discord, but leaders who prioritize these discussions and do them well, build stronger and more resilient connections, and create an atmosphere of transparency, trust, resiliency, adaptability, conflict resolution, continuous improvement and growth, engagement, safety, and inclusiveness.
I know each of you desires to make meaningful change on causes you care about. It’s impossible to do the work you want to do, be the leaders you want to be, and make the impact you want to have, without being uncomfortable sometimes. Your thoughtful and challenging conversations pave the way for innovation, growth, collaboration, and sustained success.
