Episode 32: Having Uncomfortable Conversations

April 23, 2025

In business education, there is often a reluctance to engage in what a recent post described as "uncomfortable conversations" with students. But what do these uncomfortable conversations entail? In this context, they refer to discussing suboptimal ideas that students might propose for business plans or solutions to assignments and case studies.

I would like to share my experiences from the past two decades on how to address these less-than-ideal ideas from teams working on case studies. Additionally, I want to propose some strategies for integrating this approach into the education of all business students.

Having the Conversations

As a coach, I frequently face a dilemma: I believe in empowering my team to develop their own solutions while doing everything I can, within the rules of the competition, to support them. Over the years, I have encountered many ideas that were poorly developed and lacked adequate support. While there have certainly been a few genuinely bad ideas, most fell into the category of being underdeveloped.

In many cases, I think my teams sensed my thoughts about their ideas during their presentations. I tried to let go of my poker face during practice, but maintained it during critical moments. Often, I used the Q&A session to initiate the "uncomfortable conversation," delving deeper into the team’s thought process and the reasoning behind their solutions. This approach helped me better understand their positions and determine whether the issues stemmed from a lack of critical thinking or an inability to communicate their ideas effectively. It often turned out to be a mix of both; they struggled to articulate their support and missed answering key questions.

The example mentioned in the post about Shein highlighted several significant sustainability issues in the company’s business model:

• The mass production of cheap clothing is at an alarming rate.
• The exploitation of underpaid workers in unsafe conditions.
• The pollution of the environment is caused by low-quality, disposable clothing.

If a team presented something like this, I would first use the Q&A to challenge their ideas and seek clarity on what they were trying to communicate and how they arrived at their conclusions. At this point, the team is likely already aware of my thoughts and where we are headed in the debrief session.

I believe that judges, coaches, and instructors often use a "sandwich" method of feedback. While some positive feedback is warranted at times, my approach focuses on where we can challenge teams to improve with specific feedback. It's essential to be honest about what was delivered. Too often, judges and instructors hesitate to be blunt and tell the team what they truly think, whether through feedback or the questions they ask.

My Strategy

I believe that student evaluations and ratings on platforms like Rate My Prof and other evaluation tools can sometimes have too much influence, leading to a fear of having uncomfortable conversations. Many of my former team members and students did not rate their experiences highly at the time, but later returned to thank me for my honesty and for challenging them. They appreciated our discussions around their ideas and how they communicated their solutions. Why have I continued this practice for two decades? Over the years, about 70% of my team members have returned to contribute because they found value in those experiences and learned to engage in uncomfortable conversations with the individuals they mentor. Many of them adopted my approach of using purposeful reflection to understand everyone’s experience and make an impact in almost real time. I also applied this approach in my senior classes, which allowed us to address issues quickly.

An Honest but Often Uncomfortable Conversation

Evaluations are often conducted immediately after an experience, which can be influenced by strong emotions. I’ve noticed that right after a briefing, my team members often feel emotional, tired, and stressed from the experience. As a team of competitors and coaches, we negotiated how these sessions should unfold. The goal is to capture everyone’s immediate reactions while mitigating the emotional impact as much as possible. These conversations are often uncomfortable, but we aim to share honest opinions and identify one or two challenges for both the team and individuals to address next time. This is done through purposeful reflection.

Purposeful Reflection

This process involves reflecting on what was successful and what was not, and identifying one or two goals to achieve next time, both individually and as a team. My approach is to revisit the initial goals that were set, assess the insights gained from the experience, and determine whether those goals have shifted. It is crucial to discern what valuable lessons were learned on both personal and team levels that can be applied to future experiences. Although the specifics may vary from team to team, the overarching goals remain the same: to reflect as honestly as we can on what just happened.

For instance, during a competition in Budapest several years ago, after our first presentation, we discovered that we had placed fourth in a preliminary pool of four teams. That evening, the organisers arranged a dinner on the Danube River, which was a 15 to 20-minute walk from our apartments. During this walk, I had one of the most memorable coaching experiences of my career, engaging in an incredible conversation about what had gone wrong and how we could improve. Understandably, it took us longer than expected to reach the dinner. The following day, we participated in a cultural excursion that included a 12-hour bus tour through rural Hungary, which helped the team bond. These conversations provided a remarkable opportunity for purposeful reflection, resulting in a much improved presentation for their second presentation.