Difficult conversations every leader must face

With startups on the rise, many young entrepreneurs now have the freedom to define their own leadership style and to chart a culture that will attract the right talent to join them towards their vision.

This requires a leader to be authentic, open, transparent, and more importantly, have the ability to address differences through mutual respect. And respect can be earned through empathy.

In a highly uncertain and stressful environment, this also means that many leaders are faced with tough decisions every day. But we weren’t taught how to deal with conflict or be better communicators in school.

When I was running my startup in Silicon Valley, I read the book Difficult Conversations, by Douglas Stone, Sheila Heen and Bruce Patton, which has been tremendously useful.

As I reflected on the book, I realised the one thing that ultimately matters and determines our happiness is our relationship with others in both professional and personal life.

Unfortunately, most of the time, people don’t talk about the things that matters most. We either avoid confrontation or we tend to argue, blame, and hurt each other.

Important lesson: The cover of the book Difficult Conversations, by Douglas Stone, Sheila Heen and Bruce Patton. One of the lessons in the book is that everyone has different versions of the same story coloured by their experience.

And then we don’t end up talking about our feelings and the underlying issues that caused it. When the roots of conflict are not resolved, it lingers and ultimately damages relationships. It takes so much to build trust and respect, but only one misstep to destroy it. One of the best lessons learned from the book is that everyone has different versions of the same story that’s colored by their past experiences, leading them to interpret the situation through that lens. But both versions could be true.

The best path to resolving differences is to be open enough to learn about the other person’s version and what lies underneath those reactions. Starting from a point of mutual understanding rather than going down a path of blame is already an improvement.

When we argue, we inhibit the opportunity to understand the other person’s worldview and make conclusions about their intentions and character. We compel them to change. Unfortunately, telling someone to change actually makes it less likely that they will. This is because people almost never change without first feeling understood.

For example, I once dealt with an employee who kept missing deadlines even with constant reminders. And when I brought it up, she got annoyed. I could have assumed that she was irresponsible or underperforming.

But when I shifted my purpose from trying to change her behaviour to trying first to understand her, then to be understood by her, the situation improved dramatically.

In the end, she described how stressed and overworked she was. In her mind, she had put a lot of effort into her work, and felt that I didn’t really appreciate it. In fact, I actually didn’t because I felt that she was not prioritising her tasks correctly.

On my end, I explained that I had to do extra work when she was late, and I explained that in great detail. She felt badly about it and it was clear she didn’t think about it from my perspective. Her performance changed for the better from that point onwards.