5 Easy Steps to Having a Difficult Conversation

Here’s how to turn any challenging conversation into a respectful and productive dialogue.

In the Jewish calendar we have just celebrated two of our most important and sacred holidays: Rosh Hashanah, celebrating the New Year, and our most sacred holiday: Yom Kippur, the day of atonement. We are all imperfect and that means that we hurt other people and, inevitably they hurt us, knowingly or unknowingly. This is the time when we make peace with others and also offer ourselves a fresh start.

You don’t have to be Jewish to enjoy one of the most inspiring, important, and healing practices associated with this particular time of year. We call these the Days of Awe, during which you are tasked with the challenge of stopping to think, to cross the divides you’ve inserted between yourself and others (and perhaps the divide between you and yourself!). In the week between the two holidays, it is your responsibility to have many, many crucial conversations.
Are you avoiding a conversation you know you need to have? You probably feel it in your head, in your heart — or your gut. It likely saps your energy and you just can’t find the “right” time to have it. I just returned from the Global Institute of Leadership Development which was over 350 leaders strong this year. When asked, about 75% of people responded that there was a conversation they wanted to avoid but knew they needed to have (at home or work). 

Fortunately, there is a recipe you can follow in order to have better success in these conversations.  Here’s how to turn any challenging conversation into a respectful and productive dialogue:

1. Double-check your true intentions and start with the heart.

Let’s face it: Sometimes you don’t really want to have a conversation at all. What you want is to dump your hurt and frustration on “the offender” and clear the air by giving the other person a piece of your mind with no intention of listening to their side. That’s natural and happens to all of us. But it’s not on the ingredient list for a successful crucial conversation. The first ingredient has to do with coming up with at least one mutual goal you can begin with to help open up and have a direction for the conversation. Need to fire or break up with someone? One mutual goal might be to both end up being in a job/work situation/relationship that is easier, has flow, and feels like a better fit. Sharing an outcome you can both work towards — even in the midst of this most challenging situation, makes a huge difference.

2. Speak from the “I”.

The most common breakdown in crucial conversations is the dangerous mix-up of fact and feelings. Before you enter the conversation, identify your feelings and be prepared to allow yourself to be vulnerable enough to share them. When you do share your feelings, be sure to use language like: “I feel disrespected when you continue to be late for meetings”. Do not say, “You are disrespectful when…”. 

Just as important, don’t speak for third parties (“Everybody feels this way”). Speaking for yourself and clearly delineating your feelings from the facts of the situation will enable the conversation to stay in flow and headed toward your mutual goal.

3. Check for safety.

Crucial conversations require people to be vulnerable enough to admit mistakes, see another point of view, and change their way of thinking. Having an emotionally safe environment is essential for success. And emotional safety doesn’t just apply to your feeling emotionally safe — you both need to be open to the conversation. If your dialogue partner is clearly having a bad day, or is running late — or if someone else just shared some challenging feedback with them — then no matter how prepared you may be, the conversation will fall on deaf ears. If there is not enough safety for the conversation to be successful, I strongly suggest aborting your plan and taking it up at another time.

4. Be curious and know there’s another point of view to integrate into the ending. 

Suspend the false belief that yours is the correct point of view. I know, this one is really, really challenging. People generally don’t wake up in the morning and want to ruin someone else’s day.  Try to understand where they are coming from by asking genuine questions that require more than a yes or no answer. Practice empathy and really put yourself in their shoes. Repeat what you heard to confirm understanding. Request that they do the same. Being curious makes you more empathetic and has the greatest potential to positively impact the conversation.

5. Remember that the ending is just as important as the beginning.

Brené Brown has said: “Clear is kind”. Truer words have never been spoken when it comes to ending a conversation. To end a crucial conversation means to clarify where you were, how you progressed to now and where you go from here. Keep it short and simple. Avoid multistep solutions. This is a great time to wrap it up with a S-M-A-R-T (specific, measurable, realistic, and time-oriented) goal for you to agree upon. Then thank your partner for the conversation and move on.

No conversation will go exactly as planned. The important part is to be compassionate and open to the other individual involved. Use these steps as check in points if you feel yourself getting defensive, or see the conversation diverting from its intended goals.

As you think about the crucial conversation you know you need to have remember what the Buddha said: “Holding onto anger is like drinking poison and expecting the other person to die.” This month I want to challenge you to be thoughtful and intentional with the conversations you have, to create an environment where everyone involved has the opportunity to engage in the dialogue and contribute to the solution. 

B’Shalom (in peace),


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