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How to Have Difficult Conversations at Work Like an Optimist

Difficult conversations are defining moments – sometimes, things need to go wrong before they become right.

By Gustavo Razzetti

October 20, 2021

Conflict is a necessary force for culture change – embrace it with a positive mindset

Imagine inviting the CEO of a big oil company, a youth climate activist, and an activist investor to an open stage to talk about climate change. What could possibly go wrong?


The organizers knew that the TED Countdown forum in Edinburgh would be controversial. But no one expected the panel to explode in a confrontation. Lauren McDonald gave Shell CEO Ben van Beurden the treatment he deserved, but likely not the one everyone expected.

Van Beurden opened the conversation, followed by Chris James, co-founder of Engine No 1, a small hedge fund that's shaking big oil. "We share the anxiety of what's going on at the moment. We want to be on the right side of history." – Shell's CEO tried to present a hopeful view of the future.  

Scottish environmental activist Lauren MacDonald couldn't take it – the lack of accountability upset her.

"Mr. van Beurden, I think you should absolutely be ashamed of yourself for the devastation that you have caused to communities all over the world," MacDonald began, trembling. "Already, you are responsible for so much death and suffering."

Difficult conversations are defining moments – sometimes, things need to go wrong before they become right.

"We will never forget what you have done and what Shell has done," MacDonald said before storming off the stage and suddenly ending the debate.

The anxiety was so high that even facilitator Christiana Figueres, who got 195 countries to agree on climate goals in the Paris Accord, couldn't get the debate back on track.

Climate change is not just the biggest problem we all need to solve, but also a reminder of how divided we are. We want to win, to defeat the other side rather than solve a pressing problem.

The workplace has become as divided as our society, according to Gallup. Your organization likely has some deep divisions – either about sensitive topics such as returning to the office and vaccine mandates or more mundane issues.

Difficult conversations are not easy, but they necessary. You can't move your organizational culture forward if team members are not on the same page.

Effective social change agents are relentlessly optimistic – they believe that difficult conversations can turn rivals into allies. Let's apply their lessons to the workplace.

Nothing Gets Done without Optimism

Conflict is a necessary force. Friction drives energy - and energy drives creativity. You need to embrace constructive conflict if you want to bring your team together.

The TED Countdown panel turned out to be more challenging than expected – even for a seasoned facilitator like Figueres. However, she didn't see the event as a disaster. As Figueres reflected on what happened, she acknowledged that conflict was a necessary step to better dialogue.

"There are many theories of change; many ways of engaging. For people who are truly and deeply engaged – no matter how – there's not only a space for them, but there's a need for them." – she told QUARTZ. "It will take all of us coming together and pushing each other to find the solution."

Figueres knows that change is about effective conversation, not competition. We have to increase tolerance for the other side – even if they represent the opposite of what we stand for. "The only intolerance I have, frankly, is for indifference and apathy. But I embrace everything else," she stressed.

For the Costa Rican diplomat, holding tough conversations starts by holding a safe space for the many perspectives, emotions, and intensity levels. She considers conflict rich soil – we have to embrace the messiness.

All cultural transformations seem hopeless at first. The initial debate on climate change in Paris was no exception. How do you get 195 countries to agree on a common goal and agenda?  

When Christiana Figueres assumed the responsibility to resume dialogue, she realized it was an uphill battle. "Not in my lifetime," was her immediate response when asked by a journalist if an agreement would ever be possible.

She would soon regret those words.

Figueres was horrified when she reflected on the consequences of what she said. What about the children and future generations? She knew it was dangerous for a change agent to start with a pessimistic view of change.

As she shares in her TED Talk, "Impossible is not a fact; it's an attitude. I decided right then and there that I was going to change my attitude. And that I was going to help the world change its attitude on climate change."

The rest is history. Figueres is now widely known as the mastermind behind the Paris climate agreement.

"Nothing gets done without optimism" became Figuere's driving mindset. The diplomat realized that she had no idea of how to solve the climate change problem. However, if she was going to facilitate the dialogue, she had to change the tone. There's no way to drive change without optimism.

Optimism means courage, hope, trust, and solidarity. Figueres had to challenge pessimistic underlying assumptions about people. Rather than focusing on the differences, she chose to believe that humans can come together and find solutions to help humankind.

Reflecting on the TED Countdown forum, Figueres reminds us to focus on making progress, not just the outcome.

What could be seen as a disastrous moment for an uneducated eye was a successful first step for her. Regardless of their differences, all participants touched their vulnerability – a space of both strength and possibility.

Facilitating difficult conversations requires holding space and inviting everyone to embrace their vulnerability.

Figueres said it best: "It's about moving the energy – holding it where it was, deepening it, and then allowing everyone to move on. If you deny it, then you don't harvest the richness of that moment."

Pain is a powerful connector. Acknowledging everyone's sorrow helps find common ground – not in our views, but in our vulnerability.  

Skepticism kills change initiatives even before they even start.

As a consultant, I often hear how teams are skeptical about improving their company culture. "This is not going to work here." "We already tried it in the past and it failed." "Our CEO will never change their mind." Limiting mindsets shut down possibilities and creativity, getting us stuck in rehashing past issues.

Being a stubborn optimist has been crucial for Figueres to achieve what most people thought impossible. There's a difference between seeing only the bright side and being a relentless optimist when dialogue seems to collapse.

As Figueres reflects, "Nothing gets done without optimism. Have you known a breakthrough that started with pessimistic thoughts about its potential? But our optimism cannot be naïve and ignorant: We must acknowledge the many challenges along the way, not as road blockers, but as challenging invitations to find a better path."

Relentless optimism shifts conflict from differences to possibilities.

Transformational Conversations Turn Rivals into Allies

Rivalries are everywhere. They exist in sports, business, interpersonal relationships, and so on. Rivalry encourages us to take more risks, motivating us to perform at higher levels.

The major problem with rivalries is that we distance ourselves from the people we compete against. As Adam Grant explains in Think Again, the emotions at play keep us from finding common ground with the other side.

While it's natural to take sides when discussing hot topics, it's also polarizing. Rivalries strengthen our bonding with one side, making us ignore – or even hate – those in the opposite camp. Thus, we respond with hostility when rivals challenge our views.

Facilitating difficult conversations can turn rivals into allies. I understand your skepticism. We live in a society that's more divided than ever. But it's not the first time; norit will be the last.

In The Best of Enemies, a historical drama based on a true story, Bill Riddick is tasked to solve a pressing challenge: school integration.

After an elementary school for black children is damaged by a fire, local officials – all white, all male – resist school integration. Black parents want their children to attend classes in a school reserved for whites, but the officials don't want that to happen.

Bill Riddick is tasked with organizing a charrette – a collaborative session of representatives of both camps– to find a solution through conversations. He knew that the window of opportunity was closing and didn't have much time to find common ground.

So, Riddick decided to make a bold move. He selected two unlikely rivals to co-chair the charrette: a black community organizer who dealt with discrimination and a Ku Klux Klan chapter leader.

If you think you have to handle tough conversations at work, think again.

Expectations were high on both ends. However, most people thought the charrette was a fancy way of prolonging the inevitable: school integration would fail.

If the battle felt uphill, the rivalry between the two co-chairs lowered the expectations.

They avoided speaking to one another and any possible interaction – even sitting at the same table in the cafeteria. Civil rights activist and co-chair Ann Atwater recalls refusing to attend the first meeting until her boss threatened to fire her if she didn't show up.

In just ten days, the story would take an unforeseen turn.

Rather than getting them off the hook, Riddick pushed both co-chairs to put their differences aside. He facilitated difficult, but necessary conversations. Using non-judgmental questions and flexible thinking Riddick pushed both to put their differences aside and find common understanding. Adam Grant describes this effective strategy as the Collaborative Approach – one in which we show more humility and curiosity and invite others to think more like scientists.

Handling difficult conversations, Ann and C.P. Ellis discovered that their life experiences weren't all that different. Both grew up in poverty and shared a concern for the education of young people in the community, including their own children.

After spending most of the time arguing and fighting each other, Ann and C.P.  realized that their rivalry was clouding their judgment. By defending their positions, they'd lost perspective of the ultimate goal: to help the children, not win an argument.

When Ellis and Atwater heard that the kids wanted to go to school with each other, they realized they were arguing about the wrong thing. Both missed the opportunity to do anything to make the school system better.

As Ellis shared in the An Unlikely Friendship documentary, "Ann and I got deeply involved in that school program simply because the young people were involved and they were hungry, they were dissatisfied, and they didn't like what was goin' on. She wanted to make some changes and I did too, but I think our purpose was (supposedly) different."

Finding common ground changed the conversation. It took courage to start seeing each other as allies, not enemies. They embraced vulnerability, connected with each other, and realized they were fighting the same enemy.

As Ann reflected on the journey: "He told me 'You ain't as bad as I thought you were,' and he started talkin' to me, and we started talkin' back [and forth]. We went in the office and cried because we had been doing things the wrong way just because one was black and one was white."

Moving forward, they put the emphasis on the schools instead of on each other – just like allies do.

How to Facilitate Difficult Conversations at Work

1. Agree on how you'll address conflict as a team

Avoidance is never the answer. Conflict is a signal of the gap between what a team is and what it can be. Difficult conversations help team members turn cultural tensions into fuel for growth.

Facilitating difficult conversations is tough.

Even the most seasoned facilitators get caught off guard from time to time. If not, ask Figueres about what happened at the TED panel. However, having clear rules of engagement helps. She knew that inviting people to touch a space of vulnerability can open Pandora's box – like having someone storming off the panel.  However, once people cross the line only good things can happen.

The Conflict Management Canvas is a visual tool to help your team align on how they want to address conflict together. It helps people build on their previous experiences dealing with conflict. The purpose of this tool is define a shared approach to deal with conflict.

Check out this article to download the canvas and learn how to facilitate it.

2. Integrate diverse views and beliefs

Most conversations fail when the desire to win overcomes the will to solve a problem.

The best solutions tap into collective wisdom. Like other change methods based on open conversations, the charrette solves problems by integrating multiple views, stakeholders, and skills.

Be ready to deal with chaos, confusion, and conflict.

Conflict is an opportunity: it's a signal that different voices are being heard.

Preparation ahead is critical to establish trusting relationships. Riddick could have chosen easier co-chairs but, by selecting the most polarizing figures possible, he sent a message that everyone's opinion was welcome – no matter how extreme.

Well-designed charrettes focus on understanding people. The process emphasizes listening, making room for all viewpoints, and integrating diverse ideas instead of seeing them as exclusive.

If you're curious about this method, read this post about how to facilitate a lean charrette.

3. Turn their arguments against them

Rather than trying to change how people think, use their arguments against them.

Daryl Davis is a living example of Gandhi's way of non-violent resistance. After being told by a Ku Klux Klan officer (a Cyclops) that black people had a genetic predisposition toward violence, he realized that he had to give him a taste of his own medicine.

When Davis explained that he was black but had never shot anyone or stolen a vehicle, the Cyclops told him that his criminal gene was latent – it hadn't come out yet.

To beat the KKK officer at his game, he challenged him to name three black serial killers. When he couldn't name any, Davis shared a long list of well-known white serial killers. Using the Cyclops' same logic, Davis told the Cyclops that either he was a serial killer or that the gene was latent.

The confused Cyclops found Davis' argument stupid. He soon realized that his stereotypes were based on the same (absurd) logic. He finally quit KKK – he was the first of 200 Klansman who Davis persuaded to give up their robes.

4. Find a common enemy

The best way to stop a rivalry is to let go of the differences. Start by finding a common enemy.

After days fighting with Atwater, Ellis realized that the problem wasn't black people, but the system. Both black and white students were suffering from the same educational issues. The system that held the communities down was their common enemy, not each other.

By shifting from an adversarial approach to a collaborative one, Ellis and Atwater replaced judgment with curiosity. They stopped blaming each other and started exploring new possibilities to deal with the system and help their children.

5. Start with a goal, not a destination

Great conversations help us uncover solutions. Starting with a solution in mind not only makes us miss possibilities, but accentuates differences.

If you are planning a charrette (or other collaborative problem-solving methods) with one solution in mind, don't bother. Charrettes will only be successful without hidden agendas and predetermined destinations.

Instead, start by finding a purpose that will encourage people to have difficult conversations. Focus on a challenge that is attainable, yet demanding. Begin by building trust and listening.

Effective conversations – especially when dealing with complex issues – require a collaborative process. The best solutions always come from unexpected places. Invite diverse stakeholders. The three feedback loop (proposing, listening, and revising) used in charrettes allows participants to "get it wrong twice."

Focus on the journey, not the destination. Don't rush the process. Allow people to express their needs, opinions, and ideas - everyone should feel listened to and included.

6. Don't Impose Your Ideas, Use Questions

In his book, Grant cites the story of a woman in Quebec who gave birth to a premature child. The mother was against vaccination, but her child would benefit enourmously from a measles vaccine. To change her mind, a "vaccine whisperer" was appointed.

This person used motivational interviewing to reassure the mother and help her rethink her stance.  

Motivational interviewers don't try to persuade or advise. They don't want to impose their ideas. Instead, they facilitate conversations, helping others reflect and arrive at a beneficial conclusion or decision.

Mind the difference between sustain talk and change talk. Sustain talk is about maintaining the status quo, while change talk addresses the desire or ability to make a shift. Motivational interviewers pay more attention to change talk; they listen and ask people to elaborate on it.

Consider the three pillars of motivational interviewing: open-ended questions, reflective listening, and encouragement to change.  

7. Be relentlessly optimistic

To make change happen, you have to believe that a better future is possible. This mindset is vital to achieving success. It's the most important thing. That's why I left it last – as a reminder.

If 150 countries could find common ground to address complex issues like climate change, why shouldn't your team?

Throughout my career, I've faced many organizational transformations. Many felt like mission impossible. However, people wanted to believe. They were desperately looking for a signal, some sign of how to help them reengage in a conversation.

People are not afraid of change, especially if it's for the better. They simply don't want change to be imposed on them. Involving people in open conversation is critical to driving engagement. If the problem affects your team, let them be part of the solution.

We can all find a solution despite our differences. Be relentlessly optimistic. Make people believe that change is possible – show them the way.

Handling difficult conversations is not easy. But it's better than having to deal with the consequences of the conflict we avoid.

What do you think?



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