Creative + Strategy

Investing in Your Teams


I haven’t met a leader who would disagree with this. Most say it’s important to invest. How much, is another story.

I take my management team and some friends to Montana for a week and help them disconnect. Why Montana?

Well, let me explain.

Montana is where the Big Horn River is. It’s beautiful.
We fly fish.
Do we know how to fly fish?
No. Most have NEVER fly fished before.
So, why do this again?
Because there are some very important things I want to reinforce and I’m down to do that in creative ways.

First, our company has to be a learning organization.

My job is to drive this deep into the organization. We do this by sharing content in our “share” channels in Slack and we do it here in Montana. In other words, to be a learning organization you have to love learning in general. Not just learning more about your job.

We learn how to fly fish.

In learning something new, you stumble. You fail. Failure is good.
It’s good to be a newbie. The truth is, we’re newbies from here on out.
We’re all newbies and will be until we die thanks to modern technology. What do I mean? Well, all of our tools and technology is in a constant state of updating. Your iPhone will have at least half a dozen apps that need to be updated this week. It’s in flux. Just when you learn a feature, a new one is released, and you have to relearn things. The same is true for algorithms and software. And marriage. But that’s a different story. I want my team to be comfortable being a newbie.

I want them fluent in flux.

One of the ways I’m doing that is by taking them flyfishing for a week.

When you learn something as technical as fly fishing, you have to focus. You have to be open. When you do that with a group of 10–11 other guys, there’s a little more pressure there. That’s a good thing. Learning something new in a beautiful place like Montana is icing on the cake.

The first day of learning to fly fish, I sucked. Like bad. Like really bad. I snagged my fishing line and created a rats nest of a tangle. I felt sorry for my fishing guide. He patiently figured it out for me every time. At one point I was like, “hey man, you can just take me back to the lodge.”

He replied, “not a chance.”

I suspected he’d seen this before. Executives and professionals at the top of their game in one area, now fumbling around as they struggled to learn something new. It’s funny what comes up — what you feel as a business owner — when you suck at something again in front of everyone. A little humble pie. I highly recommend it.

I recommend sucking at some things throughout the year.

I had to wrestle through a bunch of stuff personally that first time and had to stick with it. I also had to just come back to the present and reconnect with the privilege to be alive, to be there with the company I enjoy. That ability is transformative. That’s all I wanted for my team and the other guys on the trip.

This trip is expensive.

It’s all expenses paid except for airfare. So, if you can get there, I take care of the rest. That’s an investment for a small business owner, but I believe in people, and I believe in the long-term gain of having people that are secure enough to fail and grow continually. I also, love these guys and have a ton of fun with them.

Rest and Disconnecting

As a digital agency, we’re always on. Always connected. Always in the technology. It’s important to disconnect. I need to lead in this. I try to do that by creating a space where my management team can do so too. They can see me do it and they can also do it. When you disconnect, naturally you reconnect…to something.

That something is essential.

At first, the body and mind go through a digital withdrawal. You’re so used to checking notifications, emails and social media. There’s no reception at the lodge with the exception of a phone or two. There’s no internet. That’s intentional. You have to disconnect. You know what happens? “Found time.” That’s what happens. You acquire a bunch of time. And with it, you nap, read, eat, talk, laugh, light fires, smoke cigars, enjoy a beverage, fish, nap, hike or nap again. After day 3 or so you breathe a little deeper and slower. You feel the air and see the sunset. Nothing is beautiful unless you bring the right eyes to it. Sometimes, you need a chance to see things differently. To see people differently. As I said, you disconnect between one thing and reconnect to something else. My team works their butts off; I want them to disconnect and reconnect to deeper things.


Practice Vulnerability

Vulnerability used to be a no-no. I wasn’t raised to be vulnerable. I’ve had to unlearn a lot of that over the years. Instead, I believe those who embrace vulnerability grow faster. They have an edge. They have a velocity to their leadership and growth that outpaces their peers. We’re not hugging each other all day and forcing this at all! I’m just saying, being in a boat all day with different people for a week opens you up. You talk. You laugh. You open up. There’s healing in that. I’ve come to respect that so much. I’ve come to suspend my tendency to want to interrupt and change course when things start to feel a little vulnerable, but now, I let go and let it be. One time, a guy opened up about his marriage. Another moment, someone talked about depression. These are strong, brilliant and extremely capable leaders. But they have shadows too. We all do. Vulnerability brings a little light into it all. No judgments. Just good people and whiskey.


Lastly, I want to practice generosity. Growing up, we didn’t have money. I fight a scarcity mindset from time to time because quite frankly, I didn’t have much growing up. Doing this reminds me of abundance. There is abundance all around me. All around us. So I need to live and breathe and believe this. Maybe I lost you here, hang on.

Giving is leadership.

Generosity is the pathway to experience meaning in life. I want to model that too. I hope that with enough of that in the air, people will reciprocate that to those around them as well.

I understand that Montana is a type of trip that is very specific. We do all kinds of experiences at my company by the way, and they cater to our entire team. This trip is just one example of how we’re investing in people and one that is fresh because we’re leaving this week. My point is that these are investments, but the return is worth. Maybe not always reflected in the bottom line, but always in the well being of the people. To me, that counts and is worth it in the short term and the long.

cj alvarado