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How leaders turn difficult conversations into courageous ones

Carlinde Kallianiotis

How do we as leaders approach challenging conversations? This was one of the questions on our minds as we were deciding on the theme of Ginger’s recent Leadership Conversation event. To help us find an answer, we invited a group of senior, visionary and ambitious leaders to share their approach to high-stakes conversations and best practices on how to inspire others to speak up on important matters – in other words, how to be courageous. We posed three questions to our participants and received some powerful, actionable insights. 

What types of difficult conversations need to be had and why are they so important?

It’s important to say up front that these conversations aren’t only the ones we as leaders need to instigate and/or deliver – they’re also the conversations that other people need to have with us. This means that we need to reflect on our effectiveness both as messengers and receivers. 

Some of the topics that emerged in answer to this question included: when our personal values are violated; when we need to create changes in culture such as establishing more equitable practices or promoting diversity and inclusion; and when short-term thinking gets in the way of long-term strategy.

A business development leader identified a ‘silent veto’ in the room when it comes to short-term versus long-term goals. “There’s always somebody that has the power and it’s not necessarily the most senior person,” she said. “So how do you figure out who actually has the power to drive the initiative without ruffling feathers? That’s a difficult conversation.”

Sometimes the difficult conversation is hiding in the shadows. “There may be stated aims and goals but sometimes they’re being driven by something else entirely,” said a senior consultant. “And that creates a problem for the organisation as a whole.”

This led to the idea that decision makers are often pulled towards prioritising short-term wins over long-term rewards (a concept known as temporal discounting). One leader told us that she is working on building a coalition to create some comfort around long-term thinking, which is difficult in itself. 

And then there’s the difficult conversation about failure. According to the leader of a digital agency, “Everybody talks in the abstract about wanting to fail fast and learn from one another but the reality is very different. People start to backtrack. But painful and icky as it might be, once we’ve had the difficult conversations we come up strong at the end.” 

There was consensus in the group that leaders need to create a culture of psychological safety that makes it genuinely OK for people to fail. This led us into to the second question:

What top tips or best practices do you have for approaching these difficult conversations? 


In answer to this question, a leader in the tech sector introduced us to the concept of a plausible theory of success, which means a conversation that could have been difficult becomes a collaborative exploration instead. In these circumstances, it pays to dial up your curiosity.

A recurrent theme in the discussion was that strong relationships are the essential foundation for difficult conversations and you can successfully deliver hard messages if the other person believes that you truly want them to succeed and you still support them despite instigating a difficult conversation. This often means investing time in one-to-one relationships because people will be more honest in that situation than groups of more than two. A memorable metaphor that emerged here was, “You have to make the boat seaworthy before the storm arrives.”

It’s also about being open to different perspectives and giving people a structured environment in which to share, such as a town hall. But some people won’t feel comfortable in that kind of group setting. One of our leaders shared that, “Every six months I sit down with every member of the team and ask, ‘What am I missing? What are your boundaries? And what are your barriers to doing your best work?’”

Another simple tip is to write it down. Make a list of the difficult conversations you want or need to have. Prioritise them, pick one, plan it out and get the wording right so you’ll be well equipped to address any questions that arise. Once emotions get involved, it’s easy to forget what you want to say or how you want to say it. It’s also important to think about the setting and the context because if you’re going to say something that’s going to be hard to hear, you can’t do it in the hallway. In order to be effective, sometimes it’s better to wait for the proper setting and mindset.

As leaders we need to hold a clear goal in mind while seeking understanding. But how about thinking of your message or the information you’re sharing as a gift? How are you going to deliver it? Where are you going to deliver it? And how are they going to receive it in the best possible way? That makes the conversation more about them than you.

Then there’s a tip from the world of mediation, which is not to sit opposite the person or people you’re having the conversation with – sit next to each other as if you were in a movie theatre. Start by looking at the movie, at what has happened and what needs to happen next. This changes people’s perspectives – you’re not confronting each other, you’re orientated towards a collective goal.

A tip from us here at Ginger is to have a difficult conversation inside the relationship with that person. We care about each other’s needs and interests and try to lift each other up so that no one is being made wrong. On to the final question:

What can we do as leaders to support and encourage others to speak up and have difficult conversations?


First and foremost, we need to create a safe space in which people can speak openly and know they are being listened to. People will be more likely to speak up if they see their feedback being taken on board – the ‘you said, we did’ equation. 

Some great questions for leaders to reflect on are: 

  • How comfortable am I with being challenged?
  • How much tension can I tolerate while staying open and receptive?
  • How well can I role-model challenge and show that disagreement can be healthy?  

Here’s a selection of key insights from our participants:

  • The role of a leader becomes extremely important when they need to be the voice of those who aren’t willing to bring it into the group. They may need to step in and add a different perspective, even if it’s not their own.
  • Strive to be a caring and compassionate leader who is able to deliver messages with candour.
  • Focus on active listening – listen carefully and with full attention.
  • Show people what’s in it for them. If they have a difficult conversation and it doesn’t go anywhere, over time, people are going to start thinking, what’s the point?
  • Try a different approach with your language, for example, “This is my hypothesis,” which allows you to assert a position while being open to discussion.

To summarise, it’s critical for leaders to have courageous conversations that enable them to navigate intense emotions, opposing opinions and high stakes situations that could make or break business success. It’s also important for leaders to think about others during these conversations by demonstrating empathy, listening actively and openly and prioritising the wellbeing and growth of their team members. By doing so, they can establish a collaborative and inclusive culture that fosters open communication and creativity. 

Leaders who have the courage to engage in these difficult conversations can inspire their team members to do the same and create a positive and supportive working environment, promoting individual and collective success. Ultimately, courageous conversations can change the world by creating a space for understanding, empathy and progress – not just within teams and organisations but also in society as a whole. Learn more about our Courageous Conversations programme here.

Carlinde Kallianiotis

Carlinde is a partner and CEO of Ginger US, bringing over 10 years of experience as a director of training in an international franchise organization. She is an expert in coaching emerging leaders on strengthening their vision and voice and helping them to define and communicate their business strategy.

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