Are you dreading a challenging conversation, particularly in a work setting? Do you fear that it might not go as planned? You’re certainly not alone; many of us share this apprehension. Based on the experiences of my clients, here are some common reasons for avoiding difficult conversations:

People pleasing: Fear of giving away your fair share because you tend to please.

Preserving relationships: Concerns about damaging existing relationships.

Maintaining personal image: Worries about appearing too rigid or sensitive when setting expectations.

Emotional overload: Becoming too emotional and losing track of your points.

Uncertain outcomes: Not knowing where the conversation might ultimately lead – what if it worsens a bad situation?

Fear of failure: Apprehensions about facing disappointment or rejection, aka failure.

You may be able to relate to one or more of these. While avoiding a hard conversation may be a safer bet, there are times when you may get stuck if you don’t address it. As we grow and assume more significant responsibilities, managing difficult conversations becomes necessary for us to thrive. So here is a process my clients have used to make strides in such situations.

Take it as a learning process

Consider the skill of difficult conversation as a learning process akin to learning how to play the piano. Just as a beginner can’t effortlessly play an entire song, you may not handle difficult conversations smoothly initially. However, with preparation and discipline, you can gradually learn to navigate these conversations, even if the experience isn’t always seamless. As you continue to prepare and apply your learning to new situations, you’ll inevitably improve your ability to handle them. And the best part is that it helps you grow and have better personal and professional relationships.

This quote below summarizes the underlying philosophy of this approach:

“Ultimately, preparation is more about being centered and present than anticipating every possible outcome.” –Mark Nepo, An American poet, spiritual adviser, and author of over 23 books.

Here are some steps you can follow to better prepare for difficult conversations.

Before the conversation

Clarify your goals: Determine what you want to achieve in this conversation. Examples include giving feedback, sharing concerns, or communicating a difficult decision.

Detach from an external outcome: Avoid fixating on a specific outcome. Instead, focus on how you want to conduct yourself during the conversation.

Process your emotions: Take time to process your emotions related to the topic or the person you’ll be talking to. Journal or discuss these feelings with a trusted individual to clear your mind. It will reduce the possibility of unexpected outbursts or breakdowns during the conversation.

Shift from transactional to relational: Remember that one conversation won’t solve everything. Approach it as a starting point, not the end. Progress often depends on the level of trust and relationships. Focus on building trust rather than a win-lose transaction.

Prepare your main points: Write down the key points you want to convey during the conversation. Not everything you’re unhappy about will be relevant, so get an objective perspective. Focus on facts rather than interpretations.

Right before the conversation

Prepare mentally and physically: Allocate time for mindfulness exercises, like a short walk or deep breathing. Ensure you’re in a good physical state, such as not too hungry, tired, or over-caffeinated. Have water on hand to stay hydrated.

Review your talking points: You don’t need to memorize them, but ensure you understand them thoroughly.

During the conversation

Manage your emotions: Pay attention to emotional build-up and physical tension. Practice mindful breathing to regulate internal tension or take a break if needed.

Keep your talking points handy: Having your written points nearby helps you stay on track and allows you to jot down important insights during the conversation.

Listen actively: Avoid becoming too entrenched in your perspective. Instead, listen and acknowledge the other person’s viewpoint before presenting your own. This approach fosters collaboration and avoids confrontational tendencies.

Observe emotional cues: When the topic is challenging for you, it is natural that it could also be hard for the other person. So, pay attention to their tone of voice and facial expression to see how they interpret it. If you notice intensity, check on them and ask if they want to take a break.

Concluding the conversation

Every conversation deserves a proper conclusion, whether dictated by a predetermined time limit or when you conveyed the main points you prepared earlier.

Recap the key points: Ask about the other person’s main takeaways if you initiated the discussion. Encourage them to share their interpretation instead of insisting on a verbatim repetition of your words. Focus on establishing a shared understanding, as it marks the initiation of ongoing dialogue rather than an endpoint.

Establish follow-up actions and a timeline: Even if you discussed any follow-up actions during the conversation, it’s beneficial to summarize them at the end. Sometimes, the action items could come after you and the other party have had time to internalize the message better. So, depending on the situation, this part could be as simple as suggesting, “Let’s take some time to reflect and then reconnect in a few days.” Such a summary ensures clarity and commitment to any next steps identified during the exchange.

Follow-up after the conversation

Like the pre-conversation preparation, the post-conversation phase could also benefit from emotional processing and reflection. Write down your thoughts and learnings from it. Examples: “I listened better at the beginning, but towards the end, I got overwhelmed by my own emotions.” “I will clarify XYZ in the follow-up conversation.”  

If a specific timeframe was agreed upon, honor it. Additionally, if there were any other commitments or action items discussed, ensure to provide updates on those. The primary objective is demonstrating a commitment to ongoing engagement rather than viewing the initial conversation as a one-time event.

Getting through these steps might not be a breeze, but using them can help you stay centered, moving you forward instead of staying stuck. Take Stacy, for example, a director at a biotech company. She recently tried out this framework in a tough conversation and was pleasantly surprised that even though she didn’t achieve all her goals, she felt liberated. In her own words, she shared, “It gave me the confidence that I can indeed navigate such conversations,” accompanied by a genuine smile.

Sharmin Banu, an Executive Coach since 2009, draws on her extensive tech industry background, notably at Microsoft, and coaches senior leaders in Fortune 500 companies and startups. Specializing in emotional intelligence (EQ) and Executive Presence, Sharmin facilitates leadership excellence that drives team productivity. She holds a BS and MS in computer science and is a Professional Certified Coach (PCC) accredited by the International Coaching Federation. A native of Bangladesh and living in the United States for 26 years, Sharmin infuses her coaching practice with a rich global perspective.

sharminbanu@gmail.com