How to Better Handle Difficult Discussions

Learn to navigate tough talks with active listening, sodas & snacks, and empathy.

What do you do when you need to have a difficult discussion?

Like having an argument with one of our loved ones, explaining to him why it is so important we finish this project, even if it means we are less available for the couple’s activities. Or vigorously debating workloads and deadlines with our manager, telling her we cannot fit 2 litres in a 1-litre bottle and her planning is completely unreasonable.

For many, it is tempting to start overthinking these discussions.

For instance, when we know a difficult discussion is coming, we begin to imagine different possible scenarios, intensively prepping answers while slowly building up our anxiety and stress to such an extent we just cannot sleep at night¹.

Or after the conversation, we imagine how we should have answered and behaved. We think, “If only I had done this, I would have looked so much smarter and in control.” Then, we blame ourselves for not having thought about this at the moment and we become regretful².

However, it is possible to change this dynamic and prevent our overthinking with two specific steps. The first one requires reframing the difficult discussion. We need to shift our perception from a confrontation between two people to a confrontation between an issue and two people teaming up. We are not against one another; we are together against a common problem.

Source: Lison Mage

One of the first things firefighters must learn is to control their instinctual urge to run away from a fire to perform their duties and save lives. So, they train themselves to stay close to the fire and endure the heat.

Similarly, moving from opposition to collaboration is an essential mindset shift to brave and defuse the heat of the discussion. It enables us to repress maladaptive behaviours such as avoidance or blame, which would exacerbate the negative aspects of the conversation.

And this mindset also creates space for a constructive discussion. When we perceive the other party as contributing to the solution, we are more willing to listen to them. They can then tell us what they want, which leads us to our second step — perspective-taking.

When we actively listen, we form a bridge we can cross to change our point of view. As we go on the other side, we can understand where the other party comes from and get hints on how to solve the issue. But most interestingly, we can also push our interlocutor to come on our side too! The bridge can be crossed both ways.

Source: Lison Mage

Former FBI hostage negotiator explained that once your counterpart has explained what she wants, we can use a calibrated question to push her to consider our point of view. Basically, she has to walk a mile in our shoes and this will develop her ability to see things from our point of view³.

An excellent example of a calibrated question is, “How am I supposed to do that?”

In the case of a difficult discussion with our manager, she explained she needed to add new deliverables to be completed before the next customer meeting. The planning is already full, so we simply ask her how we are supposed to do, which pushes her to think as if she is in our position. It will help her understand our difficulties and think about possible solutions.

We made her cross the bridge!

Indian-American Indra Nooyi has regularly ranked among the Top 100 most powerful women in the world. She worked at PepsiCo for 24 years, including 12 as the company’s CEO, leading significant business transformation towards greener and healthier products while delivering tremendous results.

As part of her many talents, she undoubtedly masters the art of having difficult discussions.

One of them happened with Michael White, chief executive of PepsiCo international, in 2006. He was competing with Nooyi to be appointed to the highest position in the whole company. When the board of directors announced their decision to nominate Nooyi as CEO, she immediately flew to Cape Code, where White lived.

As a result of this succession process, the losing candidate generally jumps ship. Many analysts expressed concerns about White, managing one of the most important subsidiaries of the company, leaving.

Nooyi spent two full days with White, laying out the bridge between them. And she ended up asking him, “Tell me what I should do to keep you on board,” nudging him in her direction⁴. Beyond increasing his remuneration package, she offered him a seat on the board of directors and publicly recognised his crucial role in the company.

White ended up staying in PepsiCo for four more years, which is quite a phenomenon for the corporate world and an incredible outcome to credit to Nooyi’s negotiation skill.

Collaborative approach and perspective-taking are undeniably great tools to manage difficult discussions. They make us a better negotiator, but they don’t necessarily make us a better person.

For this, we need to add one last component — empathy.

Beyond our ability to understand what the other person thinks, we have to connect to what she feels. It requires exploring the heart, not just the head. And this can be challenging at first.

Fortunately, like any skill, we can develop empathy.

A straightforward way is to engage with new people. Talking to strangers at the bus stop, inviting a colleague or a neighbour we don’t know well to lunch. It requires us to go beyond small talks and genuinely engage with our interlocutors to get to know them better.

As we repeat this exercise, paying attention to the verbal and non-verbal communication of the other person, we are training our empathetic muscles.

So for this month, let’s set ourselves the goal to go out of our usual social circle and begin new conversations!

PS: If you are interested in working with me (either doing workshops in your company or for your personal development), join my next workshop => click here.


[1]- Guastella Adam J., Moulds Michelle L., “The impact of rumination on sleep quality following a stressful life event,” Personality and Individual Differences 42 (2007): 1151–1162.

[2]- Roese Neal J., “The Functional Theory of Counterfactual Thinking: New Evidence, New Challenges, New Insights,” Advances in Experimental Social Psychology 56 (2018): 1–79.

[3]- Voss Chris, Never Split the Difference: Negotiating as if Your Life Depended on It (Century -Trade, 2017)

[4]- Gandhi A.K., Indra Nooyi — A Complete Biography (Prabhat Prakashan, 2021)

Picture of Lison Mage

Lison Mage

I help clever individuals and teams conquer overthinking and perform at their full potential. Together, we can go from a place of uncertainty and being paralyzed by doubt to gaining clarity on your current situation, where you want to go, and how to get you there!


Feeling Courageous and Want To Discover More?

Thank You!

Complete the form below to get your access to the free Gratitude course and I will contact you shortly after.

5DGC HR Registration Form

Get Started Now!

Complete the short form below to get your free access to the 5-Day Gratitude Challenge.
5DGC Registration Form

Join Us!

Today, become part of the Growth Explorers Community.

Get inspiring and exclusive content to help you get more of what you want from Life, right in your inbox.