The Most Important Leadership Skill You Never Learned

Updated: Feb 11, 2020

If someone had told you when you were interviewing for that leadership role that a large part of your job would now be to have difficult conversations regularly...would you have taken the job?

When you took the job, were you offered training on how to have those difficult conversations effectively?

Probably not, on both counts.

I was 22 when I took my first leadership role. I had absolutely no idea what I was getting into.

I managed a team of about 15, one of which had been working for the company longer than I had been alive.

She wasn’t too keen on the overeager-fresh-out-of-business-school-manager, and certainly didn’t make it easy for me.

Needless to say, I’ve learned a lot in my 20 years of leadership experience. Mostly through failure and learning how to do it better the next time.

The one area I recommend leaders invest in Most, is how they communicate and connect with their people.

Because business moves quickly, conversations never get to a deeper, necessary level. And this leads to a lot of misunderstanding and miscommunication. The result: The need for difficult conversations, or Crunchy Conversations, as I call them.

Chances are pretty good that, right now, there’s at least one crunchy conversation that you are avoiding. (Read the blog post, Overcoming The Top 5 Excuses For Avoiding Difficult Conversations).

The number one key to having a successful crunchy conversation: preparation.

Let’s break down how to prepare for any difficult conversation that you’ll need to have at work:

Gather Information

Take the time to gather the relevant information and review it thoroughly. You may uncover unknown facts that alter the impending meeting.


Reflection is a tool that all great leaders use to help them grow into even better leaders.

Take 10 minutes to ask yourself these questions and write out the answers:

  • What’s your intention for the conversation?

  • What is the desired outcome of the meeting?

  • What are you curious about?

Mental & Emotional Preparation

This is the time to empty out any anger, frustration, sadness and judgement that you might have about the person or the situation.

If you go into a difficult conversation with strong emotions bubbling under the surface, you’ve just doomed yourself to a failed conversation that might cause real damage. Every single failed conversation costs an organization $7,500 and seven work days. Ouch!

A few ways to empty out both mentally and emotionally:

  • Physically exert yourself by dancing, going for a run or brisk walk.

  • Cry, scream, kick a box, hit a pillow -- whatever you need to do to in order to move those emotions through in a healthy way.

  • Write a sh!tty letter to the person or situation. Get everything off your chest in the most unrefined way. Of course, you must destroy the evidence afterwards.


Visualization is a tool that almost every Olympic athlete uses, because it works. Take a few minutes to visualize the entirety of your upcoming conversation. Imagine it going the best way possible. Do this as much as you need until you start to feel confident about the conversation.


Be mindful of when you are scheduling the meeting so you can give enough time for the conversation to happen. You don’t want to schedule it right at the end of the day if they have a hard cutoff to leave for the day. You also want to be aware if it’s their work anniversary or birthday or some other major milestone.

Get Backup

Hey, there’s no shame in having someone help you prepare or even sit in the meeting with you. I often get calls from clients to do just that and it’s always proven to be a successful strategy for them.

So there you have six proven steps to prepare to have a crunchy conversation. Now, all you have to do is go and practice. Let me know how it goes!

If preparing for this Crunchy Conversation makes your palms sweaty and you're ready to run for the hills, reach out for a download your free copy of "Ask, Don't Tell: Better questions that lead to better results" It will give you the confidence you need to have an effective and positive impact.

In Service To Your Greatness,


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