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  • Writer's pictureMaria Wade

It’s time to talk: How to prepare for tough conversations*

* this article has been originally published on HRKatha

Many of us have tough conversations almost every single day. They happen at work, at home, with friends and a variety of other stakeholders. We discuss the next promotion, a raise, conflicts, ideas and initiatives at work. We have tough conversations with kids, spouses, partners, siblings and parents. These conversations can push us (and those around us) forward, can improve performance at work and can strengthen bonds. Even through the toughest of conversations, we have a chance to improve our relationships with the people we communicate with.

In reality, however, we prefer not to have these important conversations. We put them off, and in the process, lose an opportunity to solve the issue, seize an opportunity, resolve a conflict, or advance an idea. We put our life on pause, lose days, months, sometimes years, as we tell ourselves, we’ll have that conversation “someday…”

What makes some conversations difficult?

Why do we put off certain conversations? What’s so challenging about them? It has all to do with the uncertainty of outcomes. We have something in our mind that we want to achieve or get from the conversation, but our major fear is that the result will not meet our expectations.

It doesn’t have to be this way. We can leverage other tools at our disposal to make difficult conversations no longer something to be feared, but something to be embraced; just another aspect of moving through the world. To shift this thinking, we need an actionable plan that can help us to get unstuck and overcome the fear of having uneasy conversations through planning and preparation. A tool that exhausts all possible situations and outcomes would be challenging to navigate, so here, I’d like to offer a universal framework that can be easily tailored for each unique situation.

Preparation: What can be your win strategy? What do you do before the conversation?

A few simple questions have helped my clients design a flow to support them through this type of conversation:

How can you reduce stress during this type of conversation, amplify the benefits, and minimize the risks of negative effects?

How can you stop postponing a tough conversation and start acting?

These questions can provide a starting point to guide through the preparation process, which can include the following:

Clarify intent: Get clear on your intent and what you want to accomplish through the conversation. What is the purpose of the conversation? Be honest with yourself, it will help you discover a possible hidden agenda and make sure you understand possible outcomes.

Research your counterpart: What do you know about this person? What kind of personality do they have? What ruffles this person’s feathers? What is their value system? It’s important to understand how to build the conversation, whether to use more data, present the material in a more structured or less formal way, appeal to emotions, or use metaphors and so on.

Plan: Be aware of your own emotional triggers, needs and fears. Create a plan for how you are going to centre yourself if things go out of your control. Be clear on the personal boundaries that you’d like to keep and see respected.

Draw a list: Make up a checklist of topics/ideas/aspects you want to discuss. In a hard conversation, the increased stress may play with your memory. Having a list of key points to cover will help you stay focused and ensure you don’t miss anything important.

Consider the risks: Consider the best-case scenario. It will keep you motivated and engaged. Consider the worst- case scenario. It will help you evaluate risks. Ask yourself whether you can tolerate a possibility of the worst-case scenario. Through this work, you may find out that there is nothing to fear. In some cases, the risk of the worst-case scenario may outweigh the desired outcome, and the best way to act is to hold back the conversation and reconsider your options.

Rehearse. Practice makes perfect. Sometimes, you have very clear thoughts and ideas in your head, but when it is time to speak you cannot articulate them. Having challenging conversations is a skill that can be developed. Choose a person you trust (this can be your coach, friend, or mentor) to rehearse your part of the conversation. Ask them whether your intent is clear, whether your words deliver your message and how they feel at the receiving end.

During the conversation

While begin the conversation, stay positive, keep in mind the desirable outcome, believe in yourself. As Stephen Covey wrote in his book, The 7 Habits of Highly Effective People, first seek to understand then to be understood.

  • Listen carefully as new information intake may help you adjust your strategy, shift your perception, or change your perspective. Listen not to respond, but to understand. Do not interrupt and let go of your immediate reaction. Reflect on what you heard by paraphrasing your partner’s arguments, use key words that your partner uses to make sure that you really understand them.

  • Do not assume, ask. Assumption is a killer of relationships and conversations. Stay centered, keep your integrity. Acknowledge your partner’s point of view, but don’t allow anything to break your boundaries. Brené Brown in her book, Dare to Lead, writes, “leaders need the grounded confidence to stay tethered to their values, respond rather than react emotionally, and operate from self-awareness, not self-protection.”

  • Stay curious and open-minded. Don’t seek to be right, seek to get right.

  • If you’re stuck, brainstorm. Invite your partner to brainstorm to find the best win-win solutions.

  • Breathe. When you breathe deeply, it sends a message to your brain to calm down and relax.

  • Smile. People reflect each other’s emotions. What do you want your partner to reflect?

What if something goes wrong?

Even with all the planning in the world, you cannot script out the conversation’s outcome. Something may not go as planned.

Don’t take a rejection or a verbal attack personally. As one of my teachers taught me: It’s not about you, and they will never stop.

Don’t burn the bridges even if everything is greased for the skids. Give an opportunity to all other parties to calm down, think again, and try to find a win-win solution again, next time.

The good news about difficult conversations is that another one will be right around the corner, offering you an opportunity to continue to hone and develop in this area.

I hope that this step-by-step approach will help you to start an important conversation that you didn’t previously dare to have. Don’t wait for the next time or “someday…” to come (what if it doesn’t?)…carpe diem.

Sources on nurturing relationships and strategies for tough conversations that I have found insightful are as follows:

Brené Brown, Dare to Lead: Brave Work. Tough Conversations. Whole Hearts. (2018)

Mark Goulston, Talking to Crazy (2018)

Nicole Unice, The Miracle Moment: How Tough Conversations Can Actually Transform Your Most Important Relationships (2021)

Stephen Covey, The 7 Habits of Highly Effective People (originally 1989)

P.S. A friend of mine said that it looked like the preparation takes more time than the conversation. Yes, it’s true. Sir Richard Branson, spent nearly 17 years on Virgin Galactic development to achieve his dream and reach space; his flight lasted for just 90 minutes.

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