Underdog Conversations at Work

by Sebastian Oros

Though you might not have heard of an “Underdog Conversation,” you likely know exactly how one feels.

I’ve coined the term myself, so allow me to define it. In sports, an “underdog” is a competitor who has a slim to zero chance of winning. An “Underdog Conversation” is similarly doomed. It’s the kind of talk that you often dread. It’s the kind of conversation that feels hopeless – or at least dubious. People assume that Underdog Conversations won’t result in compromise, understanding, or solution-oriented outcomes.

Gloomy, right? 

Not necessarily. I don’t believe that underdog conversations are actually doomed – they just require much more effort, skills, and tools to steer them. 

What Types of Conversations Feel Hopeless?

Underdog Conversations could include:

  • Agenda driven conversations

These are conversations that have a set side already established before they’re begun. Often, one or both sides are already entrenched, and each knows that the other fundamentally disagrees with them. 

  • Emotion driven conversations 

These are conversations fraught with feelings. Emotions are running high from the get-go. 

  • “I” driven conversations 

These are conversations that are selfish and person-centered – at least on one side of the table. As a leader, you may find yourself forced into these types of exchanges.

  • Blame driven conversations 

When one perspective is driven by the desire to shame others, it’s not a recipe for success. 

Why Are Underdog Conversations So Challenging?

It’s always hard to have frank, clear conversations, but when you’re stepping into one of these types of talks, it’s even tougher. Not only do you need to consider the natural flow of the exchange, you’re up against some complications. 

As a leader, it’s even more critical to bone up on your conversational skills so you’re ready for these types of tangles. In my work with teams, I’ve developed some tips to remember when you encounter one of these types of Underdog Conversations.

  • Agenda driven conversations 

Try: “I see your perspective. Is it okay to share mine to see if we can shed some new insight into what we are thinking as a group?”

  • Emotion driven conversations

Try: “I can see you’re very passionate about this topic. Your feelings are heard on this topic. Are we able to explore how we can use your passion to serve our goal?”

  • “I” driven conversations

Try: “It’s obvious how much time and energy you put into this. Is there a way that we can use all that motivation for the greater good of our team?

  • Blame driven conversations

Try: “The idea that we may not be serving the purpose of our team has me thinking. Could we add to our team goals of serving a more cultural enhancement approach?”

We’re Here to Help

These are not easy topics, and managing relational conflict is one of the most challenging aspects of leading an organization. The Intention Collective offers specific workshops, training, fractional leadership, and a wealth of experience to help you bring your team further toward its goals. Reach out to talk

Related Posts

Download our Free Guide:

The 3 Stages of Building a High-Performance Team (With Your Current Constraints)

Knowing when and how to grow your team can be a challenge. This guide walks you through the process we use when helping our clients navigate how and when to hire.


Next Steps: Sync an Email Add-On

To get the most out of your form, we suggest that you sync this form with an email add-on. To learn more about your email add-on options, visit the following page (https://www.gravityforms.com/the-8-best-email-plugins-for-wordpress-in-2020/). Important: Delete this tip before you publish the form.