Dear Leaders,
We all recognize the feeling—the dread that makes us want to avoid having the conversation we know is necessary but uncomfortable. Sometimes, the temptation to avoid leads us to delay or skip the conversation altogether, but silence can undermine trust and accountability. As one of my mentors would always say, a leader’s silence is often seen as an endorsement. To make things worse, it’s usually the top performers in our organization who notice this lack of accountability and interpret it as lowered expectations for some. Meanwhile, others keep giving their best, which can create resentment. Over time, these unspoken issues quietly shape culture more than any memo or mission statement.
Early in my leadership journey, I used to schedule tough conversations for Friday afternoons, mainly because it gave us both time and space to process the discussion over the weekend. However, there were moments when waiting until Friday to address issues ended up costing more than I expected. By the time I brought up the problem, many team members had already accepted the behavior as normal, assuming I hadn’t intervened, and I was okay with it — which was far from the truth. As I kept growing as a leader, I learned some useful strategies to have courageous conversations when needed while preserving others’ dignity. Here are the practices I’ve leaned on to face these moments with courage and clarity:
1. Prepare with clarity: define the issue and the desired outcome. Scripting your part of the conversation can help leaders stick to the facts, stay focused on the problem, and avoid getting sidetracked by unrelated issues. If you want to go further, rehearse the conversation with a trusted colleague.
2. Lead with empathy, but don’t shy away from the truth. In the words of Brene’ Brown, “Clear is kind.” I’ve found this to be true in every role I’ve held. Leaders often see kindness as a way to avoid the truth, thinking it will prevent the conversation from becoming emotional. However, when we aren’t honest with those we lead, we do them a disservice and dilute the message. Try pairing the issue with the phrase, “Because I care about you, I need to address…”
3. Follow up to reinforce expectations. After the conversation, briefly summarize your expectations both verbally and in writing. Though this might feel uncomfortable, it provides the recipient with clear guidance on what is expected and how to move forward successfully.
Courageous conversations aren’t easy, but they are valuable. When done effectively, leaders communicate clearly while respecting the dignity of those they serve, protect the culture they aim to build or maintain, and uphold the respect of those who consistently meet the expectations set for all members of the organization. This week, I challenge you to reflect on a conversation you’ve been avoiding and commit to scheduling it. Leaders aren’t born courageous, but when we practice being brave, we can develop our ability to act with courage even in the most challenging situations. Remember to lead with heart, soul, and from the inside out!
Yours in Leadership,
Latoya