Uncomfortable leadership

Soldiers saluting the American flag

The skill I’m currently working on improving is the skill of leadership.

It could go by other names, but in general what I mean is:

Setting standards and limitations and sticking to them—at the risk of making myself or others uncomfortable.

This includes:

• Calling someone out for being late to a call.
• Telling someone I’m disappointed in them for not following through with a commitment.
• Being offered money and saying ‘no’ to a prospective client I don’t see as the right fit.
• Voicing frustrations to close friends, colleagues, or even acquaintances.
• Telling a friend I can’t or don’t want to hang out, without giving a long-winded explanation.

Putting some of these into practice has made my heart pound and my face hot with nerves.

It’s scary to risk tension with another human being. But so long as it comes from a place of love and respect, and not superiority, it’s absolutely necessary.

But again, this is a skill.

It’s an art and a science.

I’ve heard people try to be a leader when they were really just being condescending and belittling. That’s not effective.

What is effective is telling someone with your words or your actions:

I love and support you completely. Here’s what you can expect from me. And here’s what I am expecting of you.

Last month, I gave a client a challenge to create a step-by-step system for the business he wanted to start. Two sessions in a row, he didn’t do it.

As promised, I told him I was disappointed. Not because I am the big bad boss who gave him homework…but because he was neglecting actions to better his life and do what he really wanted. I said, “This is for you man, not for me. When this happens, it makes me feel like you’re not taking what we’re doing here seriously.”

That was that and we moved on. A week later, when we next saw each other, he looked over at me at some point and said, “Thank you for laying in to me and calling me out. It’s exactly what I needed to hear.”

I can’t promise every situation will be received so well. Again, this is an art and it will take practice setting your own standards and maintaining them.

People will get defensive. Some will fight back.

But so long as you are coming from a place that’s looking out for everyone’s best interests, trust that you’re not being an asshole.

You’re being a leader.

A person’s success in life can be measured by the number of uncomfortable conversations he or she is willing to have.

Tim Ferriss