How to Prepare for a Tough Conversation: Tips from a Communications Pro

Photo by  Kai Oberhäuser

I used to work in communications for a humanitarian aid organization. My toughest job was a year-long position in Port-au-Prince following the 2010 Haiti earthquake.
Remember all those pointed questions about where did all the aid money go? It was my job to field those questions from major media outlets like CBS News and NPR.
Yet the toughest conversation I ever had to prepare for was in 2013, when I had to tell my boss that I was quitting to take a sabbatical year.
That one really made me sweat. Would he be disappointed in me? Would he say I was making a big mistake?
This conversation felt very personal. I floundered about how to prepare for it. 
Then, the obvious struck me: I was a communications professional. I had many tried and true tools to rely on.
I realized I could put them to use – for myself this time. I went behind the scenes and did the work to prepare myself for a successful conversation.
It worked. I walked out of my boss’ office amazed at how well it had gone.
I was free; and our relationship was still in good standing.
Get ready for your own big conversation
Maybe you have an annual review coming up with your boss. Maybe you have an important job interview. Or maybe you need to establish some new boundaries with someone close to you.
Whatever conversation you’ve got ahead, the five steps below will help ensure you have the clarity you need to have a constructive conversation.  
These are best practices from the world of communications. Professional athletes, celebrities, CEOs, and even the President all rely on these practices to communicate consistently and confidently with the public and media. 

Here’s how you can use them too:   

1. Clarify what you want. What is this conversation about? Why is it important?
What is your goal with this conversation? How will you know you’ve been successful?   
Do you have an “ask”? What is it?
Pause for a reality check here: Is your “ask” specific enough for the person to understand? Is it realistic? Does the person really have the power to grant this to you?
You might realize at this point that this actually isn’t the right conversation to have with this person at this time.
Or you might be ready to continue on.
2. Identify potential pitfalls. How could this conversation go wrong? What are potential risks? What are your fears or worries? Where might you get pushback?
Write all these concerns down, as well as any questions that you dread being asked. As you go through the next three steps, you’ll want to find ways to address or mitigate these concerns.
3. Craft your key messages. Every communications campaign has a set of key messages. These are simple messages that you want to be sure to convey to others; you keep coming back to them.
As the saying goes: “That’s my story, and I’m sticking to it!” This is essentially what your key messages are.
Write 2-3 key messages. Make them so simple that you’ll be able to remember them even under pressure.
Use positive rather than negative language so that you don’t put the other person immediately on the defensive and you have a better chance at an open, productive conversation.
4. Draft talking points. You can bet that before Angelina Jolie goes on any talk show in the next few months, she will have practiced her answer to the question: “What made you decide to file for divorce from Brad?”
Does she want to be asked this question on TV? No. Will they ask her anyway? Yes.
This will happen to you too. The questions you don’t want to be asked will still be asked, and the best thing you can do is prepare for them in advance – when you can give it some good thought.  
Make a list of likely (and dreaded) questions and then craft your responses. You’re making your own FAQ for this situation.
You're not alone if you struggle with this one. You might feel torn between the answer you know is true for you – and what is safe to say.
For example, your boss asks you where you want to go next in the company. You’re not sure. In fact, you’re looking for another job. But you’ve got kids to provide for and you don’t want to say anything that would jeopardize your current position. So what do you say?
Often in tough conversations, our value of honesty bumps up against our need for safety. Find an answer that strikes the right balance for you between those two very real forces.  
Remember too that you can always graciously redirect a conversation or end it. Protect yourself.
5. Practice. Role play your conversation. Practice saying your key messages and answering questions. Find someone trusted to practice with, if possible. They might come up with helpful suggestions or offer another perspective.
Finally, imagine yourself walking into the room and starting the conversation. How do you want to show up? Who do you want to be?
If you need extra courage, give yourself a talisman: Wear something that reminds you of who you want to be in this situation.
I have a necklace with a feather pendant. It reminds me of the feather that Dumbo the elephant thought he needed in order to fly.  

One Last Tip from the Coach

Before signing off, I want to set aside my comms hat and step back into my role as coach, to offer one last piece of advice:
Stay curious.
Of all the things I’ve learned from coaching, this might be the most important.
In your upcoming conversation, say all that you’ve planned say, use all your excellent prep work, be confident – and also stay curious.
The benefit of staying curious is to stay out of your fears and assumptions. When the other person says no or disagrees with you, ask them about it, instead of assuming you know why they said it.  
Then, really listen to their answer.
Staying curious ensures that you have a real dialogue rather than a stand-off. It takes some courage, but it’s definitely worth it.