Mastering Difficult Conversations

I recently listened to a talk from Dartmouth’s president, Sian Beilock, about the current state of affairs at US colleges. While discouraging, I was not surprised to learn that Dartmouth and many schools across the country are seeing more and more students academically unprepared for college - specifically in areas of reading, writing, and mathematics. However, she goes on to say that her biggest concern regarding incoming first-year students isn’t academics-related, but is actually their inability to have difficult conversations. 

A Quick Personal Anecdote

The comment struck me especially hard because I recently listened to a phone call  between my friend and her younger sister - a 15 year-old starting her first year of high school. The younger sister was calling for advice and support with a crisis - she had borrowed her roommate’s backpack and spilled a tub of nail polish inside! 

I absentmindedly listened in as my friend consoled the panicked sibling, and ultimately advised that she needed to do the unthinkable… tell her roommate what happened! This advice was met with a wave of resistance.

“I will wash the stain out with nail polish remover”

“I will hide the backpack and hope the friend forgets she lent it to me”

“I will make up a lie”

I listened to the exhaustive list of ways to avoid the inevitable difficult conversation with her roommate. 

I didn’t think much about the conversation at the time, but as I’ve researched more into the topic of the difficulties students are having navigating difficult conversations, it struck me as an excellent anecdotal example of the phenomenon.

Nobody likes sitting down with a partner, friend, family member or colleague to address an issue or admit a mistake or reflect on past mis-doings. In business school we used to call this idea “putting the fish on the table” because otherwise, if you try to hide or suppress the “fish” it will inevitably start to stink worse and worse.  So why are students and younger generations having particular difficulties with this practice? 

Why are Students Struggling?

There are plenty of reasons why this feels like such a hurdle for today’s students.

• Less practice in person: So much of our communication now happens asynchronously over text or Instagram messages. We get less practice reading facial expressions, sitting with awkward silences, or working through emotions in real time.

• Pandemic disruption: COVID took away a couple of formative years of face-to-face interaction, making things worse.

• Social media “perfection”: Online, we see the curated, polished versions of life, never the messy moments when people apologize or admit they made a mistake. That makes tough conversations feel abnormal or even shameful.

• Echo chambers: Algorithms keep us surrounded by people who agree with us. When we do run into someone who doesn’t, it’s easy to shut down rather than work through the disagreement.

The result is that problems sit and fester. Students hesitate, delay, or try to work around the issue instead of dealing with it directly.

What can we do?

1) Formal instruction and education on the topic

Just like math and science, having difficult conversations is a skill that can be taught. A large component of my MBA last year was spent intentionally studying and practicing ways to improve emotional intelligence (EQ). My only regret is that I hadn’t had the opportunity to explore this topic earlier in my academic career. 

During lectures we were equipped with powerful frameworks to navigate this space. If you find yourself facing a difficult conversation I strongly recommend the GROW Framework:

Goal – Clarify what you ultimately want to achieve from the conversation.

Reality – Assess the current situation honestly, including facts and emotions.

Options – Brainstorm possible paths forward, considering multiple perspectives.

Will – Commit to a specific course of action and define next steps.

While learning the theory is a start, the real impact came when putting these skills to the test. During class (and even as homework! ) we had numerous demonstrations and simulations where we needed to play out difficult conversations in both business and personal situations. As many of my classmates would attest, we also had plenty of opportunities to practice these skills in the real world as we navigated the high-stress environment of research deadlines, job applications, and consulting projects. 

Dartmouth’s Sian Beilock summarizes it nicely:

“All of our students go through Dartmouth Dialogues to learn how to have conversations with people you disagree with… We believe it is like a muscle; you have to train it through practice."

2)  Leverage AI and ChatGPT 

As a company focused on AI and education, I’d feel remiss not providing a couple ways AI could be leveraged in this field. 

AI can be an EXCELLENT resource in preparing for a difficult conversation. For example, if you know you will have to fire an employee in the coming days, you can work with ChatGPT to review strategies on how to approach the situation, scenario plan depending on how the employee reacts, and even develop next-step plans to help the employee navigate the future. You can even practice difficult conversations using the Voice Mode on the phone. 

Just as important as preparing for a difficult situation is how you learn from the experience. ChatGPT is a great tool to help someone reflect on a situation; with ChatGPT as a sounding board and thinking partner, explore “What went well?” “What could I have done better?” “What lessons will I take from this experience going forward?” AI-assisted reflection is an incredibly powerful tool to continuously improve your process and become a better more empathetic communicator. 

3)  Be a Role Model

While AI and frameworks are great, perhaps the best way you can help your students become comfortable with and adept at navigating difficult conversations is to be the best possible role model. Learn the theory yourself, practice with a friend / colleague / ChatGPT, and engage with your students on the topic.

“Putting the fish on the table” is never a pleasant experience, but is integral to forming strong and lasting relationships. We need to ensure the next generation is well equipped to engage in dialogue that is uncomfortable, while always leading with empathy and respect.