As a manager with nearly two decades of leadership experience, I’ve navigated countless scenarios, celebrated numerous successes, and learned from my share of mistakes. Some experiences are so deeply ingrained that I feel compelled to share them in the hope of helping others avoid the hard lessons I’ve encountered.

 

I firmly believe that 95% of leaders genuinely aspire to do right by their teams. They aim to build trust, foster respect, develop their people, and help them achieve their goals. However, many falter when it comes to initiating difficult conversations. The fear of damaging relationships often leads to avoidance, unintentionally achieving the very outcome they sought to prevent.

The Cost of Silence: A Missed Opportunity for Growth

Early in my career, I faced a situation with an employee who was technically proficient, even serving as a mentor to many, but struggled with cultural fit. The leadership team knew this individual wasn’t suitable for a leadership role, but this critical information was never explicitly communicated. When a leadership position opened up, this employee, confident in their abilities, asked if an application was even necessary. The disconnect between their perception of their performance and our view of their leadership potential was stark.

 

This led to an incredibly difficult conversation where I had to explain why they weren’t a fit for leadership. Their repeated question, “How could I not have known this?” hit hard. They were right. I had made a profound mistake by not having transparent conversations about their future within the organization. Perhaps a shift in their approach could have occurred, perhaps they were unaware of their shortcomings, and perhaps they would have worked diligently to develop the necessary skills. In the end, this person left with an extremely jaded view of the organization and of me as a leader.

 

As difficult as that experience was, it proved to be a transformative moment in my leadership journey. It taught me the profound importance of leaning into deeper conversations with individuals. I now strive to understand their goals, identify the gaps that stand in their way, and use this as the foundation for their development and growth. Where I see significant disparities, I engage in those tough discussions directly. It may be a “not now, but with continued growth, it’s possible in the future” conversation, or perhaps a “this may never be a fit” discussion? The key, however, is that these conversations happen.

Embracing Transparency: A Path to Unlocked Potential

Having learned this difficult lesson, I embraced tougher conversations and committed to ensuring my staff felt more supported in their learning journeys. Fast forward a few years, and I had an employee who was ambitious and aspired to leadership, but frequently made mistakes, making it difficult to trust their technical abilities. During a coaching conversation, I was direct: “You want to be a leader, but you can see how I’d have a hard time promoting you with the number of errors we see.” Her response, essentially, was that she was already looking for her next role, eager to move on from her current one.

 

We discussed how one of the most effective ways to prove oneself is to excel in the current role, to push beyond expectations, and demonstrate the capacity for more. Something in that conversation resonated with her, and she did a complete 180. Over the following months, she meticulously corrected her mistakes, actively helped other staff members, and proved her capability to not only perform her role but also exceed it. She quickly emerged as a leader, positively influencing the team culture, and as a result of her hard work, launched a successful leadership career that continues to thrive today!

 

As a natural procrastinator, whenever I find myself avoiding a conversation out of fear of upsetting someone or damaging our relationship, I revisit these two scenarios. I am determined never to repeat the first experience and am constantly reminded of the immensely rewarding outcome of the second.

 

The conversation you’re avoiding might not be as monumental as these examples. It might be with someone not looking to advance, but whose daily performance or interactions are impacting those around them. What are the implications if you continue to avoid that conversation? What message does that send to others? How might it affect the culture you’ve meticulously built? There is no downside to having a positive, solution-oriented conversation aimed at helping someone grow.

 

Ultimately, choosing to lean into difficult conversations is not just about addressing performance issues; it’s about your responsibility as a leader to foster growth, build trust, and cultivate a culture of transparency. It’s about unlocking potential, even when the path to get there is challenging. These conversations are, in fact, an act of care. They are how we truly help our people and our organizations thrive.