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.

How do I respond?

Today is the day when most people's New Year's Resolutions kick in. Enjoy the holiday on the first. Start on the second.

And inevitably, there will be people who break their resolutions today or tomorrow or next week or next month. Whenever. Doesn't matter. It happens.

Some people say that resolutions are bullshit, and instead create goals for the year or a vision board or roadmap. Some people want to cultivate lifestyle changes. Call it what you want. For this conversation, let's just say that there's something that wants to be accomplished.

I know this goes against positive psychology and doesn't look pretty in fancy type on instagram, but it has served me well in the past:

Fail in advance.

Allow yourself to fail, even if it's only in your mind, so you can take a look at how you respond. That's where the juicy stuff is.

If and when you don't stick to your resolution every single day for 365 days, what do you do the next day? Do you give up? Oh well, nice try, maybe next year lol. Or do you get right back on the wagon? Or do you double down the next day to make up for it?

This comes from one of my favorite leadership lessons.

A leader has already thought about all possible outcomes in advance so that they aren't taken by surprise and can act accordingly. The best leaders are the ones who always seem in control no matter what chaos my arise, and a cheat code for this is to experience all of the feelings and emotions around each possible situation in advance. It's not easy or for the faint-hearted, but is a gamechanger.

There's also another nice bonus to failing in advance.

It gives you permission to not have to be perfect.

The need to be perfect adds a whole lot of pressure. Yes, some people actively seek that pressure and perform better that way, so if that's you, proceed as you were. For the rest of us, we've got enough other things happening in life that adding this desire to be perfect just complicates things further.

So what if you caved and ate a chocolate bar one night or you missed a day of meditation? Life doesn't end there. Know in advance what you'll do after this happens and you can respond accordingly.

Are we getting to the good part?

I had a thought this morning about "getting to the good part." It comes at a time of exciting business things happening, the closing of a major personal open loop, craziness in the White House and geopolitical news, and also a bigger movement happening that's hard to put into words.

There were two things that came up with this thought that felt worth sharing.

1. It feels like we are in between the old and the new. We know we no longer want the old, and yet we're not quite at the new just yet. But we can taste it. We long for it. And it's coming. I've felt this for me personally, some close friends, and society in general in a way. It's exciting. And it's frustrating.
2. On the flip side of that, if we were truly "getting to the good part," that would imply that things aren't good now. And I categorically reject that. Things are not perfect, not even close. There's always opportunity to improve. And even in the middle of turmoil, chaos and uncertainty, this is the most amazing time to be alive.

The conclusion I came to this morning is that it does feel like things are getting better which is exciting, and at the same time, even with whatever nonsense may be going on at the moment, things are pretty damn good.

How do I measure my own personal growth?

I had a magical moment of reflection a few days ago. It was an awareness I am very grateful to have had and just as easily could have missed. And it got me thinking...

As a person who spends my fair share of time focused on my own personal growth and development and working with others to do the same, how come I had to randomly stumble upon this realization?

At an immersive event in June 2018, I wrote down a list of 5 areas that currently felt out of integrity for me. Believing integrity to be one of the most important qualities in a leader and correspondingly having it very high on my list of personal values, these 5 areas did not feel good to me.

And yet, after that weekend, I did not take any action on this new information. Instead, the list got lost in the shuffle and life happened.

Fast forward to last week. I was looking for something in my old notes when I came across this list. It stopped me dead in my tracks.

Without any awareness of this happening, I resolved all 5 areas that were out of integrity. It forced me to stop and consider all of the growth that occurred, often behind the scenes, over the last year. It gave me a warm, fuzzy feeling.

And so, I'm doing a little rapid prototyping on some ideas to help me better track my growth and development over time. This way I can be more intentional about these amazing moments of reflection and ideally have something to share with you all to do the same.