Why do I seek out difficult conversations?

This might sound counter intuitive at first, but I have found that a measuring stick for the greatness of a leader can be marked by the number of difficult conversations that they've had.

A first tendency could be to think that the best leaders aren't having very many difficult conversations at all. They are incredible visionaries who avoid all obstacles and conflicts. They are fully pre-emptive in everything that they do. All sunshine and rainbows.

We know that is not true.

Being a great leader is measured in how we perform in the good times and the bad and everything in between. And one of the most important things a leader can do is to always be willing to have the difficult conversations. Say what needs to be said with no fear or hesitancy of the challenging aspects of these conversations.

It's not easy, especially in the beginning, to always be the one who is saying the things that need to be said, and yet it is so critically important to the impact and success of a leader. It takes courage. It takes a certain level of detachment from how the leader may be perceived in the short term. And it takes a willingness to ruffle some feathers to help ensure the highest possible outcomes.

The best leaders I know are actively seeking out the difficult conversations. These conversations are wide ranging:

• With a team member who may be upset about something
• With a client who is angry with how they've been treated
• With a prospect who is going to go with a competitor
• With an investor who has some critical feedback on growth
• With a family member who is doing something hurtful
• With a significant other when there is some form disagreement

The list goes on and on. The way to the best results and biggest impact is through these difficult conversations. Once we have opened up a safe space for people to say what isn't being said, we can embrace it head on. Otherwise, these things may linger in the background leading to assured destruction: either through catastrophic damage or a slow drip of degradation of quality or engagement that corrupts everything it touches.

When we open up space for these conversations, it has the opportunity to move the relationship forward in leaps and bounds. It also has the possibility to end a relationship that is no longer aligned. And while that might not feel so good at first, it is way better to be open and honest and say what needs to be said rather than pretending everything is fine.

As leaders, we want to know these things so that we can take action. Armed with the knowledge of the unspoken, we can properly steer the ship. Otherwise, we are guessing, second-guessing and making assumptions.

In my personal experience, these difficult conversations do not get easier. They are always difficult, hence the name. What does happen though is we get more skillful in our approach, in our delivery, in reaching our desired outcomes. And the only way to build that skill is through getting in more reps.

The best leaders are the ones who have had the most difficult conversations and are well versed in cutting through the bullshit and speaking the unspoken.

Please don't artificially manufacture difficult conversations if there's nothing there. There will be plenty of opportunties to practice this as step into our role as leaders. Just be ready to face them head on when they arise.