How to Lead with Confidence: Lessons from a Difficult Conversation

blog Sep 27, 2023

Navigating Uncharted Waters

Have you ever found yourself in a conversation so uncomfortable and challenging that it haunted your thoughts for years? It may have left you questioning your leadership abilities and replaying the scenario in your mind, wondering what you could have done differently.

13 years ago, I had a difficult conversation that forever changed my approach to communicating with my team. This conversation taught me invaluable lessons about leadership, difficult conversations, and the courage to lead confidently.

Picture this: It was an ordinary Friday afternoon – when I should have been home with my baby. Instead, I was at the office, facing a situation that would shake me to my core. I was leading a growing team, and on that Friday, I was about to have one of the most challenging conversations of my professional life.

Little did I know that this encounter would become a cornerstone in my journey as a business leader.

The Gut-Wrenching Dilemma

Have you ever been torn between your intuition and the expectations of your team?

My instincts screamed at me to avoid the impending conversation and shield myself and my team from discomfort. Yet, my team believed that this conversation needed to happen (it did) and that it needed to happen now (it could have waited for me to be better prepared).

They believed it was an essential step for our collective well-being – which was true – but I wasn’t ready to have that conversation on that day, no less doing it with zero preparation and even less confidence in how to navigate it.

I had the excruciatingly difficult conversation with one of my staff members and ended up sobbing uncontrollably behind closed doors in my office afterwards.

There are so many reasons why avoiding difficult conversations is bad for business, but it’s crucial to be well-equipped before you initiate difficult conversations with your team.

Lessons from Hindsight

Hindsight is a powerful teacher, and looking back, there were several crucial takeaways from that pivotal moment that reduced me to tears:

Timing Is Everything

One lesson that stands out is the significance of timing.

Never, under any circumstances, should you have a difficult conversation on a Friday afternoon. It's a recipe for disaster. The impending weekend acts as a buffer, allowing misinterpretations and emotions to fester unchecked by the reality of the workplace.

Pick a time and a place to have a difficult conversation with intention and consideration for both you and the other person.

Guarding Personal Boundaries

Protecting personal boundaries is another vital lesson. While being a dedicated leader is commendable, it's equally important to assess the urgency of a situation. Sometimes, protecting personal time is paramount, ensuring you're mentally and emotionally prepared for what lies ahead.

Just because you feel pushed into a particular action doesn’t mean you have to rush into it headfirst and underprepared.

Listening with Discernment

Listening to your team is crucial, but remember, it's your job as a leader to distill their input into a well-considered course of action. While my team genuinely believed the difficult conversation was necessary, I should have listened, evaluated, and formulated a more effective strategy.

The Power of Frameworks

Approaching such conversations with a clear plan or framework can make all the difference.

While some people can "wing it," having a structured approach enhances your chances of achieving the desired outcome while maintaining professionalism and empathy.

Managing Reactions and Responses

Dealing with emotional responses in these conversations is a skill that can be developed. Remaining calm, even in the face of anger or frustration, can help de-escalate tense situations and create a more productive atmosphere.

If this isn’t your strength, plenty of training and resources are available to help you skill up so you can lead confidently when you next have to tackle a difficult conversation.

Seek Support and Guidance

Perhaps the most significant lesson I've learned is the importance of mentors, coaches, and a support network. Having someone to turn to for advice, guidance, or simply a listening ear can be a game-changer in handling difficult conversations effectively.

Ensure you surround yourself with the support you need at different stages of your growth as a leader.

So why share this deeply personal and challenging experience?

It's simple. I hope to spare you from similar ordeals by sharing the mistakes, lessons, and insights gained from that difficult conversation. I want you to embrace challenging conversations with confidence and skill, armed with the knowledge that you're not alone in facing these struggles.

Mastering the mental game of being a boss is no easy feat. It requires finesse, empathy, and a willingness to learn from your experiences.

Difficult conversations are inevitable when you’re a boss, but they don't have to be daunting or impede your and your team's ability to succeed. With the right approach, support, and mindset, you can navigate these challenging waters and emerge stronger as a leader and person.

Remember, you're not alone in this journey; there's always room for growth and improvement.

If you’re struggling with any aspect of your leadership journey, the team at People Powered Business is here to support you. We meet you where you are and collaborate to get you where you want to be: leading a thriving team confidently.

An invitation to join a thriving business community