The Top 5 Questions to Ask Yourself before a Difficult Conversation

Are you tired of avoiding difficult conversations?

Or perhaps you find yourself ruminating about what you should have said, after the fact.

If you’re thinking, “Heck yes, Nayla!” then this post is for you.

That’s because I’m sharing 5 power-questions that have proven time and time again to help my clients have difficult conversations with more clarity, confidence, and ease.

If you feel like you’re spinning your wheels in this area and wonder where to begin, read on.

Difficult conversations come in all shapes and sizes. Perhaps you need to speak to your boss about her management style, or that coworker who is constantly sarcastic towards you, or perhaps it’s that family member who is kind of a mooch.

We often shy away from these conversations or blunder mindlessly into them like a bull in a china shop because let’s face it, they’re just plain awkward.

How do you tell your boss that she’s a micro-manger? Or your coworker that his communication style sucks? Or your family member that she’s a freeloader?

No one wants to hear these things. And you’re right about that… with one slight nuance: no one wants to hear those things in that way.

When we learn how to authentically hit that sweet spot between candor and diplomacy, the world of difficult conversations changes drastically for us. We actually see results from our efforts and we no longer avoid these conversations like the plague. I will even venture so far as to say that we begin to look forward to them.

The 5 questions below are a simple, yet powerful way to prepare yourself for a difficult conversation. They will help you take your best shot at achieving the impact and results that you want.

So let’s delve right into them:

(1) In 10 years from now, when you look back on this conversation, how do you want to see yourself having handled it?

This first question will help you tap into your personal core values so that you can align your conversation strategy with your BEST SELF. If you nail this question, the rest of them should flow effortlessly.

(2) How can you begin the discussion in a way that highlights your positive intentions?

The first few moments of any difficult conversation are crucial. When you set the tone well and reassure the other person of your positive intentions, they are much more inclined to be open to listening to what you have to say.

(3) How can you say what you need to say in a way that they’ll be able to hear it?

You may want to call the other person a liar, but if you do this, they will check-out of the conversation and this is not your goal. So spend some time on framing. Saying something like, “You told me X and then I heard you say Y two days later… help me understand, I feel like I’m getting mixed messages.” will take you much further.

(4) How might you have contributed to things and how can you acknowledge this?

This is an easy one. If you said or did something that you regret, acknowledge it… up front. Even if you don’t believe that this is the right thing to do, it will help the other person hear your perspective (which is one of your goals).

(5) How prepared are you to hear the other person’s side of things? 

Be totally honest with yourself when you answer this question. If you’re not prepared to hear their side, then don’t expect them to hear yours. I often spend a lot of time on helping clients work through this piece.

So there you have it! The top 5 questions to help you prepare for difficult conversations. There are many more that I cover with my coaching clients, including what they will do if the conversation falls off the rails, but that’s a topic for another post.

So, now that you’ve seen the 5 power-questions…

Which question do you like the best and why?
Which one is the most challenging for you and why?
What else would you do to prepare?

Feel free to share your responses – I always love hearing from you.

Happy reflections!