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Tuesday, August 9, 2022

Why Uncomfortable conversations are critical for success

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Uncomfortable conversations come in all shapes and sizes and for a variety of reasons.  Getting comfortable with uncomfortable is essential for a fulfilled life. Uncomfortable conversations aren’t fun. They’re the conversation you put off until the last minute, anticipate with dread, and worry about. However, stepping into them is an essential ingredient for effective leadership and a hallmark of a successful career.

Reasons for avoidance 

There are two main reasons for avoiding conversations, you:

  1. Worry about the outcome 
  2. Don’t know what to say 

In the first category, shying away from such conversations may appear on the surface to be the easy option, but experience shows that avoidance doesn’t work.  It merely sends the problem underground to fester and then blow up, more significant and more troublesome than if you’d stepped in earlier.

There are also times when you don’t say what needs to be said because you’re putting your feelings first.  When someone around us – be it a work colleague or friend – experiences something unexpectedly sad, we often don’t know how to react.  They may have been made redundant, lost a loved one or experienced a troublesome circumstance.

For example, recently, a former work colleague was made redundant.  What surprised them and made the situation harder was the reaction of their work colleagues.  They simply stopped speaking with them, making the person feel like they didn’t matter.

It’s unlikely that this was their colleagues’ intent. Instead, because the work colleagues felt awkward and unsure about the person’s emotional state and likely response, they walked away from reaching out.  Their uncomfortableness and concern about saying the wrong thing meant they did nothing – leaving the person feeling hurt, confused and isolated.

Connection matters

In these situations, by avoiding the conversation, the opportunity to deepen and strengthen relationships is missed.

Conversations are at the root of human connection. 

Research by Jian Guowei (Cleveland State University) and Dalisay Francis (University of Hawaii) – Conversation at Work: The effects of leader-member conversational quality – found that the quality of the conversation between leaders and team members had a significant impact on employee’s organisational commitment.  

How we talk, when we talk, and how much we talk to each other matters. 

By having an open conversation, being transparent with the other person about the value you place on the relationship, and understanding their intent and background, you open the path to building a more stable and healthier relationship.

Having a healthy working relationship with a work colleague doesn’t mean you always have to agree with them.  It does, however, require you to take the time to see things from their perspective.

It’s easy to make assumptions about a person’s intent, particularly in an organisational context and if your relationship with the person is challenging.  We can wrongly infer a harmful intent, which impacts how we react to their opinions and ideas. Consequently, each time we have a challenging conversation, we learn and grow from the experience.  It broadens our perspective and reminds us not to be closed to other people’s opinions.

When you make the first move, reach out and initiate the conversation it puts you in a far better position to navigate how it will proceed. 

Dr Brenè Brown in her book Dare to Lead refers to these conversations and actions as your arena moments. These are the moments when you are called to show up, be brave and walk into the arena despite your fears. 

Before stepping into the arena, it can help to consider your approach.

Getting ready

In getting ready for the conversation, keep true to your principles.

For example:

  1. Acknowledge yourself and that feeling uncomfortable is ok
  2. Enter the conversation with good intent, a genuine interest in the other person and a desire to achieve a mutually beneficial outcome 
  3. Strive to ensure the person knows you value them
  4. Put yourself in the other person’s position and consider how you want to be treated
  5. Abandon any assumptions you hold about the other person’s intent. Instead, be curious and, where relevant, inquire and clarify so you can be clear on what’s said
  6. Where possible, have the conversation face to face recognising the importance of body language in communication, and a time when neither you (nor your colleague) are rushing or anxious. It’s essential to be centred, present and calm.
  7. Create space for the other person to feel fully heard; listen, get comfortable with silence and don’t talk over the other person
  8. Consider in advance your core message. People hear words differently and to have a hearable message you need content that connects with them on a cognitive and emotional level.

Remember, there is no perfect time. There’s ‘now’ or ‘later’, and the problem with later is it often never arrives.

As Author Tim Ferris remarked: “A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.”


Written by Michelle Gibbings.

Have you read?

Best CEOs In the World Of 2022.
TOP Citizenship by Investment Programs, 2022.
Top Residence by Investment Programs, 2022.
Global Passport Ranking, 2022.
The World’s Richest People (Top 100 Billionaires, 2022).
Jamie Dimon: The World’s Most Powerful Banker.


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