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What to expect from our Difficult Conversations Workshop

Mastering the art of difficult conversations is essential for fostering a culture of open communication, collaboration, and continuous improvement.

Raquel Rojas
September 14, 2023
What to expect from our Difficult Conversations Workshop

Embracing failure as a natural part of sustainable growth of any organization is a necessary mindset. This is why we believe that mastering the art of difficult conversations is essential for fostering a culture of open communication, collaboration, and continuous improvement.

In this article, you’ll discover how the Difficult Conversations Workshop focuses on the importance of these courageous dialogues and provide you with practical strategies to not only survive but thrive while communicating with your team. We'll also share some cases where this workshop may not align with your company’s needs.

Difficult conversations vs. crucial conversations

We all have experiences with conversations that are loaded with emotional charges, leaving us drained or even disoriented. But what if we told you that you could reframe these talks into something positive and beneficial? 

In the Difficult Conversations Workshop, we'll explore how altering your perception of these "difficult" conversations into "crucial" ones can empower you and your team members to approach daily issues with a renewed perspective of empathy and understanding. 

We will provide you with practical, effective strategies rooted in our deep understanding of interpersonal communication dynamics within Failure Culture.

Vices of communication

When we find ourselves facing a crucial conversation, our defense mechanisms kick in to protect us from potential attacks from the other person. Ironically, these attitudes that we anticipate are the same ones that end up making the interaction more challenging.

Despite having learned to call these conversations "crucial," they still involve intense ideas and emotions that can test our patience and ability to communicate effectively.

Although it's not our fault, it is our responsibility to rationalize our behavior and choose a different tone when communicating from a place of intense emotions.

In this module of the Difficult Conversations Workshop, we’ll explore the practices to avoid in order to communicate our ideas effectively. 

Radical Candor

Kim Scott created the term Radical Candor, which involves being honest and challenging others while genuinely caring about their potential for improvement. 

This practice requires empathy and affection and centers around two key factors: personally caring about the other person and being willing to address them directly. In this module of the Difficult Conversations Workshop, you and your team will discover how to apply Radical Candor and how it can enhance your teamwork.


In our workplaces, there are often long stretches of time where things seem to be going well, and there are no pressing issues or discussions that require crucial conversations. However, the reality is that there is an ongoing process of continuous improvement happening behind the scenes, and it occurs more frequently than we care to acknowledge.

One of the most important conversations that occur in the workplace is feedback. Despite its significance and frequency, feedback is often a conversation that we avoid, downplay, or underutilize due to the perceived discomfort that it may bring. Unfortunately, these beliefs prevent us from using feedback as the valuable tool that it is.

In this module, we aim to explore the true value of feedback in the workplace and provide some tips on how to handle these conversations effectively.

The conflict and its resolution

Conflicts are a common type of crucial conversation that seems to lack order. Unlike other types of conversations, conflicts are more chaotic and have varying reasons and intensities. However, even though they may seem out of control, there are basic principles and tools that can help manage them effectively.

No one likes difficult conversations, especially when it comes to conflicts. But it's essential to know how to confront and manage them because these skills are useful in any other similar conversation.

In this module of the Difficult Conversations Workshop, we'll explore the nature of conflicts, how to approach them differently, and some steps to find assertive and efficient solutions.

In which cases is our Difficult Conversations Workshop NOT a good fit for your team or organization?

  • You are looking for a quick solution

We propose this workshop as the first in a series of 5:

  1. Fear of failure
  2. Psychological safety and vulnerability
  3. Failure Management
  4. Communication and difficult conversations ;)
  5. Innovation

We recommend holding the Fear of Failure workshop as the first step towards building a Failure Culture that seeks tangible results in the short, medium, and long term. These results have to do with productivity metrics, talent retention, employee well-being, as well as employee engagement and commitment, and employee turnover. However, just like all our workshops, we’re dealing with taboo topics here. This brings us to another case where this workshop would not be ideal for your company: 

  • Your organization doesn't seem to prioritize the emotional aspect of work life enough

Talking about our emotions or fears can lead to rejection, causing people to avoid vulnerability in group activities.

Creating a safe space where employees can freely propose, test, and communicate ideas without fear, shame, or guilt is the first step to achieving a cultural change in your organization. This will benefit the company and create a happier and more productive workforce.

The Difficult Conversations Workshop is a service offered under The Failure Program, aimed at helping organizations embrace Failure Culture and use it to their advantage through vulnerability, authenticity, and creativity.

Ready to enhance your team's communication skills? Let's embark on this transformative journey together. Simply complete this form!

*Source: Failure Survey 2021-2022

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What to expect from our Difficult Conversations Workshop
Raquel Rojas
Marketing & Comms Manager
Neurodivergent, antiracist, queer, feminist, vegan for the animals, mother, sister, lover, Mexican, immigrant. Fan of music festivals by the beach, gin tonics, and annoying people with her unsolicited unpopular opinions.


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