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Dec 3, 2019 | Updated Apr 27, 2022

Workplace Culture: How to Make Hard Conversations Easier

Even people with considerable power — owners, CEOs, board chairs — are often reluctant to have the tough talks that are required for them to achieve the outcomes they desire.

Workplace Culture: How to Make Hard Conversations Easier

Image: Two former Blink engineers at work in our Seattle studio. We did not take a photo of an actual tough conversation.

One of my favorite TV shows is “Kitchen Nightmares” with chef Gordon Ramsay. I love it because Ramsay exposes the toxic organizational dynamics behind the failing restaurant that he comes to redeem. Inevitably, Ramsay has to have a tough conversation with the owner/chef/manager in which he tells them the truth about their poor leadership, mediocre menu, and bland food. Usually, the staff is waiting in the wings fearfully and hopefully, anxious for Ramsay to deliver the news that they have been unable to communicate to their boss.

Though Ramsay is blunt and hard hitting, he also delivers the message with hope and the promise to get the restaurant back on track. Like any good consultant, he knows how to have high stakes conversations.

As user experience design and research consultants, the core of our work is to help our clients recognize where their products and processes can improve. As a result, part of the job is to have hard conversations. We have learned that delivering this kind of communication well is a rare and highly appreciated skill.

Whatever the reason, people who are comfortable initiating high stakes conversations are remarkably rare in today’s society and there are few organizations where hard conversations occur on a regular basis. Even people with considerable power — owners, CEOs, board chairs — are often reluctant to have the tough talks that are required for them to achieve the outcomes they desire.

As a result of this reluctance, people don’t get the feedback they need to improve their products, processes, or performance. Cumbersome systems, processes, and people remain in place long past their usefulness. Mediocrity goes unchallenged and becomes the norm, and the race to the bottom begins.

Image: "Difficult Conversations" Illustration by Holly Prouty

Practicing the truth

High stakes conversations happen in multiple contexts in our lives, not just with our clients. They are crucial in preserving relationships with co-workers as well as our family and friends. Like any skill, the ability to have hard conversations needs to be practiced. The more you do it, the easier it becomes. And, importantly, the more you do it, the more skilled you become.

Most people have experienced tough conversations that are awkward, hurtful, and even damaging. Often, these situations occur because the people involved have waited too long to bring up the problem, hoping the issue would resolve itself. Or, they have avoided the conversation out of fear of hurting feelings or damaging their relationship. It is only when they’ve reached a point of being fed up and even angry that they finally say what needed to be said long ago. This usually results in an interaction that becomes needlessly adversarial, disrespectful, and in some cases, damaging.

Hard conversations don’t have to be this way. When you learn to do them well, you don’t have to put them off until you’ve reached a breaking point. Instead, you can use them to create positive outcomes, just like chef Ramsay.

Here’s how


Think carefully about the message you want to deliver. It might help to write down your main points.

Be specific

Avoid generalities and exaggerating. It is rarely useful to use the words “never” and “always” (for example, “you are never on time” or “you always look like you are falling asleep in meetings”). Go over what you want to say with someone else who you trust to give you good feedback.

Start from empathy

Your motivation should start from the idea that you want the person to reach their full potential. Give them the benefit of the doubt and assume they are doing their best. Put yourself in their place. How can you best deliver the message in a way that they can hear it and see a positive result? What is important to them?

Time it well

Be sure to give yourself enough time to talk it through. Find a place that is private. Make sure the other person is in a state of mind to receive the message.

End on a hopeful note

Make sure the person understands the positive steps that can be taken in order to move forward.

Whether the problem is with a client, colleague, friend, or family member, you don’t need to call in a consultant to have a tough conversation. Develop your skill and practice it regularly. Before long, it will come naturally and gracefully.

For more reading, Blink’s CEO has a similar approach and talks about her experiences in her blog post, “Why the Toughest Conversations Matter Most.”

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