Event Recap: WIN NYC x frog x Professor Todd Jick of Columbia Business School on Conversations on Politics and Diversity in the Workplace

For our first WIN NYC event of 2019, we gathered at frog for an evening with Todd Jick, Columbia Business School Professor, on a skill we could all stand to improve: Creating more meaningful discourse. As a leading expert in organizational change and leadership, Professor Jick guided us in an academic learning session and vibrant discussion. Using Google’s famous diversity memo as a jumping off point, we explored how we can lean into uncomfortable conversations instead of dodging them.

Read on for a playbook to grow this skillset – practice makes perfect, after all.


The Big Problem: Difficult Conversations Cause Stress and Avoidance

Globally, people feel more divided today than ever before. Whether over politics, social movements, technology, etc., vehement disagreement exists across all areas of our lives (see this SNL sketch for relatable discomfort.) It’s no surprise that 66 percent of us feel stressed or anxious if we know a difficult conversation is coming up. We fear confrontation (29 percent), agonize over how the other person will respond (43 percent), worry that we’ll fail to communicate clearly (31 percent), and/or dread that we’ll get emotional (29 percent).

These concerns often lead us to avoid uncomfortable conversations entirely – 57 percent would do almost anything to avoid having a difficult conversation. In the field of innovation, we need to be keenly aware of this instinct – embracing tension and differences in viewpoints is essential for discovering new insights and building better solutions. We simply cannot avoid it if we want to be successful.

The Dos and Don’ts for Having Difficult Conversations


If you choose to wade into a difficult conversation (you should!), here are tips from Professor Jick and WIN members:

Before: Prepare

Before you walk into a difficult conversation, consider your mindset and prepare. The most productive conversations occur when you arrive with curiosity, seek to learn about the other person’s perspectives, feelings, and experiences, and try to discover common ground.

Also, don’t forget to conduct yourself maturely and respectfully, so you can leave the discussion having a sense of satisfaction about how you conveyed your own perspective, feelings, and experiences.

Do not walk into a conversation with the intention to purely persuade the other person to change their core attitudes and beliefs. Prepare to disagree – frequently. And do not expect your partner to walk into the conversation with an equally open mind or the same goals.

At The Beginning

Set a constructive tone. Listen in a way that makes the other person feel heard. Speak in a way that helps others hear you.


When You’re There: Utilize T.A.L.K. (dive into this framework from the Dean of Fuqua here)

Think about framing the conversation not as difficult, but as an opportunity to come to constructive outcomes and new solutions

Always use clear, simple, and neutral language. Refer to specific examples and facts

Listen to what the other person is saying and show you care about their point of view

Keep the focus on the issue, not the person

When Wrapping

In an ideal world, every difficult conversation ends when two parties reach a consensus. When this isn’t possible, can you reach a compromise? When you can’t, it might be time to respectfully, agree to disagree and move on.

As a Friendly Reminder

Professor Jick shared a quotation that is great food for thought: “The biggest communication problem is we do not listen to understand. We listen to reply.” Let’s all try to do more listening to understand.

Do you have an interesting story on how you once handled a difficult conversation? Tips to add to the discussion? Drop us a line at team@womenininnovation.co – we’d love to add to this growing list so we can all feel empowered to finesse this important skill.


Written by Emma Anderson, Katie Burwick, Lauren Wong, and Sascha Donn. Photos by Katie Burwick. Special thanks to Professor Jick for an amazing session.

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