6 Questions to Help You Prepare for a Difficult Conversation

Have you ever been stressed out just thinking about a difficult conversation you need to have? I know I have. And if we are already stressed before having the conversation, imagine how much more stress we’ll feel during the conversation.

The fact is, nearly all of us at some point in our lives will need to have a difficult conversation. That could be with a sibling, parent, child or friend who does not want to be vaccinated during a pandemic. Or with a colleague who isn’t pulling their weight in a group project. Or with your boss for their lack of clarity in communicating deadlines.

These are not easy conversations to have. And depending on the kind of relationship you have and the conditions precipitating the difficult conversation, there’s every chance a difficult conversation could turn into a disastrous one.

What can you do to minimise that possibility? One way would be to have a really clear outcome for your difficult conversation, before you have it. As Stephen Covey says, highly effective people always begin with the end in mind.

“To begin with the end in mind means to start with a clear understanding of your destination. It means to know where you’re going so that you better understand where you are now and so that the steps you take are always in the right direction.”
– Stephen R. Covey

Questions before you start

To help you get clear about what end you have in mind for your difficult conversation, here are some questions to ask yourself beforehand:

What steps can you take to prepare for a difficult conversation? Photo by Joe Yates on Unsplash.

What steps can you take to prepare for a difficult conversation? Photo by Joe Yates on Unsplash.1. The first question to ask is, “For the conversation to go really well, it will be like what?”This question trains your attention on what you would like to have happen. What kind of end would you like from your difficult conversation?

The clearer you are about the answer to this question, the clearer the end will be in your mind. And the clearer we are about what it is we want, the more likely we will put energy and creativity into what needs to happen next.

2. The next thing to consider is, how will you know the conversation has gone well? A useful question to ask around this query is, “And what will I see and hear that lets me know it’s going well?” This allows you to get clear about the evidence you’ll need to measure the success of the conversation. The clearer you are about evidence, the easier it will be for you to assess how well the conversation is going, or has gone.

3. Next, ask yourself, “And for the conversation to go really well, I’ll need to be like what?” This creates self-awareness and reminds you to take responsibility for getting what you want. Your answers could be anything from “I need to be on time” to “I need to be calm” or even, “I need to be fierce”.

4. Then ask, “And what will others see and hear that lets them know I’m being on time / calm / fierce / etc?”What is the behaviour you will be demonstrating to take responsibility for getting what you want? The more evident this is, the more you will be in charge of the kind of conversation you would like to have.

5. Next, ask: “And what support or resources will I need?”Difficult conversations are called “difficult” for a reason. That means we might need help or support so that we can be at our best while we’re having a difficult conversation.

Getting clear about the help you need will enable you to articulate the support you need. Just knowing I have support often makes me feel more confident about doing something difficult. Hence, this question is a real winner for me.

6. And finally, how will you know you have the kind of help you need? Ask yourself, “And what will I see or hear that lets me know I have the support I need?”

On your own or together

These questions are from a process called Clean Setup, that was developed by Caitlin Walker, the author of From Contempt to Curiosity: Creating the Conditions for Groups to Collaborate.

You can ask yourself these questions on your own, and record your answers somewhere. Or you could get someone to ask you these questions. If they haven’t been on the Building Trust Remotely or Drama@Work or Better Conversations programmers that we offer, then let them know you need them to ask you the questions only. You aren’t looking for their opinions or suggestions unless you specifically ask for it. The idea behind these questions is to give you a chance to figure out your own outcomes and how you will achieve them, without necessarily being influenced by someone else, unless that’s the kind of support you need.

Another way to use the Clean Setup is to have all the parties involved in the difficult conversation answer these questions, before you start. This makes transparent everyone’s agenda so that any conflicting agendas can be attended to openly, rather than being hidden. Having said that, unless you already have a high degree of trust and compassion in your relationship, it might be best to have a trained and independent facilitator do this for all of you.

Remember, there are all kinds of things you can do to prepare for difficult conversations. Taking the time to answer these questions beforehand will certainly help you prepare so that a difficult conversation doesn’t have to be more difficult than it needs to be.


Leave A Comment