Hold Still, This Might Hurt: Tough Conversations in the Workplace

By YPO Member Michael Cohen, COO of Whistle Sports

There are some conversations in life that are just more difficult than others. They’re awkward, a bit embarrassing and simply put, they make you uncomfortable. Whether it’s with your partner, your boss or even unruly team members, there comes a time when inevitably you find yourself elbow deep in an awkward conversation.

These conversations can never be avoided; in fact, they’re necessary. Whether you’re having a tough conversation with your partner that leads to a more fulfilling relationship, or a tough conversation with your coach that results in a better batting average, they all lead to growth somehow. In a business world obsessed with growth, whether it’s revenue, headcount, profit or geographies, these conversations become essential. Business moves fast, and we iterate in sprints, which means your team needs to move themselves equally fast, renegotiating their boundaries and their expectations rapidly. The reality is that these conversations are avoided, and growth becomes stunted, for both the individual, team, and the company.

Of course, it’s easy to avoid them, because for the most part, no one likes confrontation or hurting someone’s feelings, but being nice is achieving nothing but incrementalism, and while marginal gains are positive, I’m guessing you’re looking to achieve more with your company than marginal gains.

If you are struggling to have those difficult conversations, here are some tips that I’ve found to be helpful over the years.

Start asking “so what?” and “why?”

  • “So what?” You’ve completed one portion of the project, but so what? What does it mean for our team, our customer, our audience, or even our strategy?
  • “Why?” Why did you approach it this way? Why is this the best outcome? Why did you use the people you did? Why did you use the resources you did?

Create a culture of challenge

A culture of challenge isn’t necessarily one with competing coworkers, but rather an environment where peers challenge each other and hold one another accountable. We can easily complain to our peers and moan about work problems, which sometimes is necessary for emotional sanity, but limit it to the first few minutes of a conversation, and then challenge one another to push forward.

Neutralize the emotion

It’s easier said than done, but hang-ups, insecurities and past grievances block growth. It’s your job to ascertain how to create room in other people for growth. If the person you’re speaking to does get emotional, honor them and acknowledge their feelings. Then let them know you trust and believe in them and this difficult conversation does not negate previous accomplishments.

Create safe spaces

Difficult conversations are private and should be treated as such, an opportunity for vulnerability and honesty. Let your people know that exchange is not politics or office games, but rather a space wholly for them.

Manage up

Difficult conversations exist across hierarchies, which means you might have them with your seniors, but that doesn’t mean you have to call your boss out, because no one in their right mind is going to do that. However, you can align expectations, discuss what is expected of you both and set non-negotiable touch points that holds all parties accountable.

Those five things make huge differences, but they aren’t happening in business today. One of them might be, but certainly not all of them, and the result is high attrition rates and unproductive teams that lack motivation. Have the tough conversations and the awkward chats, have them often. Eventually your people will thank you for it, and you’ll be moving your business forward, which as a leader, is what you’re here to do.

YPO member Michael Cohen is COO of Whistle Sports. He holds a bachelor’s degree in finance and marketing from Goizueta Business School at Emory University. The impact of human behavior on businesses and organizations has long-fascinated him. Cohen’s expertise covers ways to collectively empower, inspire and create room in those around us as part of company strategy, operations, finance, talent management and leadership functions. The approach helps develop transparent and collaborative teams that drive top-line growth and scale operations while finding efficiencies and increasing productivity. His background spans investment banking, private equity, consulting and startups.

With more than 26,000 members in more than 130 countries, members of YPO are peers who share in common the achievement of success at an early age; a commitment to learning as a lifelong adventure; and a desire to connect authentically in an environment of trust and confidentiality. If you are a member interested in contributing, please email blog@ypo.org.