How To Manage Difficult Conversations With Ease

How To Manage Difficult Conversations With Ease

Leadership | Posted by - April 20, 2020 at 12:30 am

There’s no denying that honest conversations can be uncomfortable. Stomachs can curl at the anticipation of a team member’s reaction to critical feedback. But the consequences of avoiding conversations can be worse: a person won’t know how you feel, they won’t have the opportunity to improve, and you won’t receive honest feedback in return. Teams then lack the opportunity to grow. 

San Francisco-based entrepreneur Kim Scott learned the value of giving criticism from Sheryl Sandberg while they worked together at Google. Scott wanted to bring this style of candor - challenge directly while caring greatly, as she defines it - to other entrepreneurs. In 2016, she co-founded Radical Candor and a year later published Radical Candor: Be a Kickass Boss Without Losing Your Humanity, a New York Times bestseller. 

“Radical Candor is a simple idea, but it’s not easy for most of us humans to implement in our everyday lives,” said Scott. Now she’s gone a step further to help leaders prepare for difficult conversations through a new program, Improvising Radical Candor in partnership with Second City Works. Sweet Fish Media, Gather, and ZenHub are some of the first companies to complete the course.

“Practicing improv helps leaders strengthen problem solving skills, stay grounded in the moment, and listen to focus on others instead of their own comfort.” Scott shares examples to help you manage difficult moments with ease:  


When a team member gives you feedback, your first reaction might be to defend and explain yourself. When you criticize the feedback you receive, people will be less likely to open up in the future. 

Focus on understanding what the person is telling you and try to learn something. When the person finishes speaking, check that you understood correctly. You could say, “So what I hear you saying is…” Repeat the issues they’ve raised, as you understand them. Ask, “Do I have that right?” Ensure you honestly understand the point of view. 

When I worked at Google in San Francisco, I delayed the start of a meeting with our team in Dublin because I didn’t want to cut my morning short with my newborn twins. I thought everyone would understand, but a young father on the call pointed out that I pushed the meeting into the team’s dinner hour. I was ashamed, but I was grateful he spoke up. I heard the feedback, understood what he was saying, and course corrected for the future.


Stay grounded in the moment instead of thinking about the past or the future. Being present allows you to tune out distractions and focus on what’s in front of you. This practice can sometimes be uncomfortable, especially if you have to endure prolonged silence. 

For example, if you ask your team: “Is there anything I could do or stop doing that would make it easier to work with me?” and you are met with “Oh, everything is fine, thank you for asking,” you may be tempted to move on and pat yourself on the back for even asking the question. 

Don’t do this. Stay in the moment and ask again. One technique is to count to six before responding, forcing someone to endure the silence. The goal is not to be a bully but insist on a candid discussion—to make it harder for the person to say nothing than to share what they’re thinking. 


You can’t practice candor if you don’t care about your team members as people. Being others focused means being committed to the success of others. When I worked for Sheryl Sandberg at Google, she once gave me feedback after a presentation. After praising me for delivering a successful presentation, Sheryl told me that I said “um” repeatedly, and she offered to get me a speech coach. I brushed her off and made a shoo-fly gesture with my hand. Sheryl laughed and said, “When you do that thing with your hand, I feel like you’re ignoring what I’m telling you. I’ll have to be direct to get through to you." She then said that although I was one of the smartest people she knew, saying “um” every other word made me sound stupid. This time I heard her.

Sheryl gave me direct feedback because she cared about me, and she didn't want something that I could correct to impede my success at Google. She said I “sounded” stupid rather than I was stupid, and she offered to help fix the problem.

Tags: business, business advice, communication, entrepreneur, google, leadership, management, problem solving

Kristen Marano

Kristen Marano covers women and their work for publications around the world. She has interviewed some of the most influential business leaders in Canada and the most passionate change makers in towns and cities as isolated as Perth, Western Australia. Most recently she interviewed Canadian businesswoman Zita Cobb about reinvigorating the economy in Newfoundland through the arts. Kristen's work encourages women to share honest and open perspectives about the emotional challenges of their journeys.

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