Preparation Overlooked: How to Prepare for Difficult Conversations

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In an average week during college football season, student athletes can spend up to 30 hours a week practicing for an upcoming game. This includes physical practice, meetings to breakdown plays, and exercise, all for what amounts to 1 hour of actual game time. A professional orchestra musician spends 40-50 hours a week practicing and honing their skills while only playing an average of 6 hours in front of an audience. Similarly, in our professional lives, we spend countless hours preparing for a project rollout or a presentation for important stakeholders.

You don’t typically have to convince people that practice and preparation are an important part of performing well. But when it comes to important conversations, we often assume we’ll figure it out in the moment. We tend to avoid thinking about it or put it off until the last minute, leading to anxiety and ineffective communication. In this article, we’ll explore why people overlook preparation in difficult conversations and the correct way to prepare so you can feel confident going into high-stress conversations.

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Why Do We Avoid Preparing for These Conversations?

Difficult conversations can be uncomfortable, emotional, and unpredictable. We worry about saying the wrong thing, hurting someone’s feelings, or damaging a relationship. As a result, we tend to not only avoid these conversations – we also avoid thinking about them. Our brains don’t know that it’s only practice, so it’ll still bring up the same feelings of anxiety or stress. However, when we’re not prepared, we struggle to articulate our thoughts and emotions. Or, we may react impulsively without considering the consequences.

Another reality is that we often underestimate the complexity of the situation. For example, if we need to deliver negative feedback to a team member, we may assume that we already know what to say. However, this oversimplification can lead to missing context clues, or we forget to take into account the history and dynamics. By taking the time to prepare, we can anticipate different scenarios, questions, and objections, and develop a more effective communication strategy.

What Goes into Effective Preparation?

As the saying goes, “Practice doesn’t make perfect. Only perfect practice makes perfect.” It’s not enough to just practice. If you shoot 100 free throws at practice but miss all of them, did you really improve? Effective preparation for difficult conversations involves a combination of mental and logistical preparation as well as finding ways to rehearse what and how you’ll say what you need to say.

Here are the things you’ll need to prepare and ideas to practice:

  • Think through your goals: What is the problem or issue that needs to be addressed? What is the desired outcome or resolution? Clarifying the purpose and goal of the conversation can help us stay focused on the big picture and avoid getting sidetracked. The goal needs to be observable and measurable.  For example, if you need to discuss a team member’s performance, the purpose may be to help them improve their skills, while the goal may be to increase their productivity and morale.
  • Research and gather information: What are the facts, data, or evidence that support your perspective? What are the other person’s perspectives and concerns? How can you find common ground or solutions? By gathering and organizing information, we can support our arguments, anticipate questions and objections, and show respect for the other person’s perspective. For example, if you need to negotiate a contract with a client, you may need to research the market rates, analyze the client’s needs and preferences, and develop multiple scenarios and options.
  • Reframe your limiting mindsets to successful mindsets. Identify the mindsets that bring you the stress and anxiety about the difficult conversation – do you worry about ruffling feathers? Are you worried about being seen as aggressive? Do you worry about the potential for the other person to yell or become emotional?  Instead, ask yourself, how can I reframe this situation to be a positive purpose? How can I reframe hearing “no” or receiving pushback as a good thing?
  • Identify your emotions and triggers: How do you feel about the conversation? What are your fears, assumptions, or biases? How can you manage your emotions and stay focused on the goal? By acknowledging and managing our emotions, we can reduce the risk of getting defensive, angry, or overwhelmed. For example, if you feel anxious about the conversation, you may need to practice relaxation techniques. Deep breathing or visualization before and during the conversation is one way to cope with this.
  • Understand the dynamics at play: What is the other person’s communication style? How do they process information – internally or externally?  What questions or concerns might the other person have? How can you address them respectfully and persuasively? By anticipating questions and objections, we can prepare more effectively for difficult conversations and avoid being caught off guard. We can also show that we’ve done our homework and are willing to engage in a constructive dialogue. For example, if you need to convince a coworker to support our proposal, you may need to anticipate their reservations, such as cost, feasibility, or impact on their workload, and prepare evidence and counterarguments.
  • Write down your plan and your “script”. While you don’t have to write out everything, you should still jot down key phrases or points to hit. Consider also writing down reminders for you to slow the conversation down or to take deep breaths when you’re feeling stressed.
  • Practice and role-play: How can you rehearse the conversation and get feedback? Who can help you prepare? Practicing and role-playing the conversation can help us refine our communication skills, improve our confidence, and anticipate different scenarios. You can also get feedback from a trusted colleague, mentor, or coach who can provide constructive criticism and support. For example, if you need to deliver bad news to a customer, you may need to practice your tone, language, and body language, and role-play different reactions and responses.


Difficult conversations aren’t easy, but it’s essential for effective communication and relationship-building.  Effective preparation can make all the difference in how the conversation goes.  A boxer who spends months eating well, exercising, and sparring will always be more successful than the boxer who does that same preparation for a couple of weeks.

Effective preparation can develop the skills and mindset to approach these conversations with confidence and empathy. Whether you need to deliver feedback, negotiate a deal, or resolve a conflict, you can use these tips to prepare more effectively and achieve better outcomes. So, the next time you’re facing a difficult conversation, remember to take the time to prepare, and you’ll be more likely to succeed.

Chris Wong
Chris Wong

Chris Wong started his career as a direct care staff member for adolescents in a psychiatric inpatient hospital. He enjoyed working with the youth so much that he went to Boston University School of Medicine, where he received his Master’s in Mental Health Counseling and Behavioral Medicine. After graduating, he worked as a licensed therapist in a variety of settings, including an adolescent residential treatment center, outpatient clinics, and mobile crisis evaluations in the Boston and Cambridge area.

In 2016, he started work as a training manager at a non-profit child welfare agency, developing and facilitating trainings to support staff around clinical interventions, cultural humility, and any needed training support for programs. In 2019, he moved into a new role as Director of Employee Learning and Development, where he oversees leadership and career development for the organization. This includes training and coaching for leaders at all levels of the organization to both strengthen and build a leadership pipeline.

Chris is a certified executive coach and works with HR and L&D leaders on difficult conversations, conflict resolution, building powerful relationships, leadership development, productivity, leading change, diversity, equity, and inclusion.

Connect with Chris on LinkedIn.

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