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The risky art of having

difficult conversations


  • The nodding crowd
  • Collective intelligence
  • Fuckups, obstacles & bad words
  • Happily Disagree
  • Ruinous Empathy is ruining empathy
  • How does Giving a Damn look?
  • Inner Conversations and Feedback


Many of us were raised with the belief that openly disagreeing with people is kind of rude, unnecessary and even demonstrates bad manners. This is why, in our adult lives disagreeing with someone can cause so much internal conflict.

Expressing different points of view to our colleagues, managers, partners and the random people we meet friend’s dinner parties can be difficult or even controversial.

If you have nothing good to say, don't say it at all

We always end up having to have these unavoidable conversations, but choosing to have them sooner, rather than later could prevent major work mistakes and losses.

Those ugly products that no one buys, the toxic new hires that become permanent or the time you snapped at a colleague in the middle of a meeting all happened because we didn’t speak out about what was troubling us.



Aversion to conflict is not the only obstacle when we are trying to contrast ideas, it is also the false understanding of what consensus really is.

We tend to think that consensus is reaching unanimity when what we’re really trying to achieve with consent is to think together (which has nothing to do with the idea of thinking equally). 

When people genuinely think together there will be debates and disagreements because our opinions are different and that’s the process we go through to reach a better solution. However, we must acknowledge that this isn’t a smooth process, a quiet vote and the crowd nodding after the very first solution is proposed, for the first stage creative destruction is required.

If everybody's thinking alike then somebody isn't thinking
George Patton

The nodding crowd; escaping from Group Thinking

Being part or reinforcing consensus as achieving unanimity or as Irving Janis called it Groupthink -the process of faulty decision making that can occur in groups as a result of forces that bring a group together- might be harmful and is killing teams and groups creativity to think in better solutions.

Here are some of the symptoms and behaviors described by Janis to identify the kinds of groups that don’t have diversity in their decision making.

Illusions of invulnerability lead members to be overly optimistic in risk-taking. No one wants to be the party pooper when everyone’s excited about boarding the Titanic.

Unquestioned beliefs lead members to ignore possible moral problems and consequences. Like when an all-white, all-male panel discuss diversity and inclusion and the famous “we have always done it this way!”

Rationalizing prevents members from reconsidering their beliefs, therefore ignoring warning signs. Kodak’s leadership didn’t believe digital photography was the future and they rationalized their assumptions.

Stereotyping leads members to ignore or demonize members who may oppose or challenge ideas. “You know how the Finance team is always against us”

Self-censorship causes people who have doubts to hide their fears. Loud “strong” leaders that move fast don’t make time or space to listen to the more introverted or analytical members, who then self-censor.

“Mindguards” behave as self-appointed censors to hide problematic information from the group. Like leaders that treat their teams like kids who can’t handle the whole truth.

Illusions of unanimity lead members to believe that everyone is in agree
ment and feels the same way.

Direct pressure to conform is placed on members who question the group, seeing them as disloyal or traitorous. Watch out for people who play the victim when their ideas or work are criticized.

Collective Intelligence: Why thinking different is better

Believing that a solution created by the majority of a team is better than a brilliant idea proposed by a genius, is key to protecting the collective intelligence of a group. Protecting this collective intelligence, above all else, especially after your idea gets dismissed by the team, is trusting in the greater good. 

That’s the first step towards building a safe space, where crazy innovative ideas can happen. By accepting that in our group everybody has their own opinion and that will cause conflict and debates, we generate trust in the team, allow for diversity and help to see differences as a key for more inclusive and creative solutions. 

Before diverging and jumping into diversity, we think these tips on how to manage, handle, and foster difficult conversations will help you on a personal and professional level.

How not to have any conversation

First, we need to visit the bad habits that cause us to engage poorly when we start an interaction. Before we prepare to engage in a situation where there is a different opinion to ours, we should consider how we normally address and initiate a conversation, do we unconsciously adopt attitudes that could lose or decrease the other person’s empathy. 

According to
Pilar de la Torre, these are types of violent communication:

Fuckups, obstacles & bad words

Beyond the obvious obstacles such as body language (showing someone your middle finger), facial expressions (rolling your eyes when someone walks into a room), or choosing the wrong words to communicate your thoughts (asking someone to do unpleasant things to himself), there are multiple ways to mess up your communication attempts.

Paralanguage. This is the way we use our intonation when sending a message verbally. Paralanguage creates a nonverbal communication barrier when it is misunderstood or applied inappropriately. For example, the tone of voice we use to say things.

For us, using a high pitch could be “normal”, but perhaps it will make the other person feel attacked. To avoid this issue, remember to be sensitive to the other person. Communication always involves two parties, don’t make assumptions.

Silence. The lack of expression sends a message in itself, and it can be used in a positive or negative way. On the positive side, silence helps people think about the information they are receiving, however, it can also be used to ignore or threaten. Body language is helpful for understanding the tone of silence.

Silence is a big part of the communication process, and we need to embrace it. Remember to set the right tone for your silent moment, and if you are on the phone or on a web call with no video on, always mention that you need a minute to think.

How to actually have any conversation

Happily Disagree

So let’s get serious and start talking about how to have difficult conversations. The first thing is understanding that what we are trying to achieve is a bullshit-free zone with the people we work with, admire or share something. 

We want you to picture something, or at least try to. If we didn’t have all these mental barriers and reservations about how to approach certain situations, like how to say something without causing our colleagues, partners or parents to feel offended…

  • …how many mistakes could we have corrected already? 
  • …how would our communication look? 
  • …how much could we have positively impacted others?

Leave aside that offended reaction from your colleague or boss after you say she’s always late, your father’s reaction after confessing that you’re not as interested in yoga as he is. What difference does the difficult conversation make?

Mistakes can be corrected, that's one of our biggest blessings, we are unfinished animals, we can evolve.
Eric Jiménez
The Failure Institute

Embracing the idea, that one of the most valuable gifts you can give and receive is the opportunity to improve someone’s life, is the starting point for engaging in difficult conversations; happily knowing that even though hearing or to saying something specific might not be pleasant, it’s still the best thing you can do.

Ruinous Empathy is ruining empathy.

Kim Scott, the author behind the concept of Radical Candor once shared a personal experience:

Although one of her employees was not the best at his job, she decided that since she had nothing good to say, she would be nice and not to say anything… for ten years! In the end, the employee was finally fired by Kim herself. After the awful surprise the confused employee only had one thing to say during his offboarding:

Why for all this time didn’t anyone tell me?!

By not confronting the truth and sharing feedback, she unfairly took away her employee’s chance to change and improve his opportunity areas.

The phenomenon of choosing silence over telling someone something uncomfortable is what Kim called Ruinous Empathy, and it’s what we normally do when we face something unpleasant: turn around. and hope it magically fades by itself.

Maybe sometimes you will be lucky enough that the things get fixed without you doing anything, but the vast majority of times, you’ll need to do something and address the situation. This works both ways, sometimes you will receive information about yourself which is not pretty, and sometimes you will need to give information which is not pretty to others.

This is aligned with two variables of a relationship:

  1. Give a damn about others or, how we like to say, care personally 
  2. Be willing to piss people off or challenge directly.

This means that the other person is important enough for you to make them see that they need to improve something. You can’t just avoid the conversation because you want them to notice the issue and you know they can do better.

It is similar to noticing a hideous habit that you have and you can’t unsee or tolerate it, so inevitably you have to do something about it. This is what Radical Candor is, accepting the moral obligation to improve the lives of your closest circle of people.

Caring personally is not about sharing sordid details of one's life or forced chit chat at social events it's about finding time for real conversations.
Kim Scott
Radical Candor

How does Giving a Damn look?

How do you create an atmosphere in your social groups where anything can be said? How do you communicate that the healthiest thing to do is actually express our thoughts and feelings in the clearest, most transparent and caring way?

  • Protect diverse thoughts in your meetings. Even ask for them.
  • Avoid the nodding crowd.
  • Incentivize honesty, transparency and confrontations.
  • Make your team feel comfortable talking to each other when things are not working.
  • Encourage people to choose directness over talking behind people’s backs.

These are some points to think about everyday and reinforce as much as we can. Of course leading by example is the most powerful way to do it.

When conflict is to difficult to solve, people will avoid it.
Kim Scott
Radical Candor

Inner Conversations and Feedback

And as we like to say, the most important changes start within. You won’t be able to start having difficult conversations if you are not willing to admit the ugly truths about yourself, and more than admitting, reconcile with them.

Making yourself more aware of your dark side and starting to improve it, is the first and last step to becoming comfortable with the difficulty.

Feedback, and most important, Self-Feedback is an amazing tool and should be used to constantly review with how you are doing with yourself.

We want to ask you these interesting questions that The school of Life created about Candor:

  • How much can you be a friend to yourself and remain on your own side day-to-day?
  • How far can you admit something about yourself that you don’t necessarily like?
  • How much do you need to insist on your own normalcy and being right?
  • Can you explore in your mind the dark side of you without feeling compelled to look the other way?
  • How ready are you to listen when valuable lessons come in painful disguises?

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