For the past two weeks, I've been traveling through Italy and I spent the last week hiking in the Dolomites with a friend. On one of our final days we hired a guide to take us up Piccolo Lagazuoi.
We started at Passo Falzarego and made our way toward the Cengia Martini, a narrow ledge (cengia is Italian for ledge) cutting across the face of the mountain. During World War I, Italian soldiers occupied and fortified this ledge, building shelters, trenches, kitchens, and even a medical post into the side of the mountain. From there, we would eventually make our way through the Galleria Lagazuoi, a system of tunnels dug through the mountain by Italian soldiers, as we continued toward the summit.
Before we started, our guide explained what we should expect. The hike would be physically demanding and we had options to shorten it, but that wasn't what concerned me. My friend and I are both fairly fit and comfortable hiking considerable distance at elevation. What caught my attention was his description of the vertical exposure - the "cengia."
There would be sections where the trail narrowed to about a foot wide with the rock wall on one side and a significant drop on the other. In some places, the only thing to hold onto would be a steel cable drilled into the rock. We wouldn't be clipped into it as you might see on more difficult Via Ferratas. It was simply there to hold with our hands as we moved across the mountain.
I'm generally okay with heights, but I told our guide early that exposed terrain like that might make me nervous. I had never really done anything quite like it before, and as he described what was ahead, my imagination was doing a pretty good job of making it worse. Then we started climbing.
As we made our way up the mountain, our guide was watching us. He could see that we were physically capable of the climb. We were keeping pace, moving comfortably, and handling the terrain well. The closer we got to the more difficult sections, the more confident he seemed that we would be fine.
Eventually we reached one of the exposed sections.
He stayed close. He showed me where to put my hand. He showed me which rock to step on. Which ones to avoid - the "polished rocks" as he called them. And then he encouraged me to keep moving.
At that point, I stopped thinking very much about where I was. I didn't look down. I focused on my hands, my feet, and where I wanted to go next. One handhold, one foothold, and another and another. One step at a time.
Later, our guide asked if we wanted to continue a little farther along the exposed cengia to see the remains of the Italian military positions built into the mountain during World War I. I looked at the path ahead and if it were just me and my friend, I probably would have suggested we don't go forward.
But by that point, our guide had already watched me climb for quite some time. He knew the terrain. He had guided other people through it. He had personally climbed much more difficult terrain. More importantly, he had watched how my friend and I were handling the mountain that day.
He believed I could do it and gave me a look confirming it. I said let's go, and he followed with an enthusiastic, "andiamo!"
After we got back (and we did take the long way down for little more punishment), I started thinking about what the guide actually did for me that day.
He didn't make the mountain less dangerous. He didn't make the trail wider. He didn't remove the exposure or pretend there wasn't a significant drop a few feet away from me. He simply understood the terrain better than I did.
There were moments when he could say, "Put your hand here. Step on this rock, not that one." There were other moments when he didn't need to say much at all, he just marched on ahead. He had seen enough to know I was capable of continuing, even when I wasn't entirely convinced myself.
I've spent much of my career working working with business owners and leadership teams, and I couldn't help but see the similarity.
Most of the people I work with are smart and capable. They've already accomplished difficult things. In many cases, they've built businesses from almost nothing into organizations employing dozens or even hundreds of people.
But eventually, every leader encounters terrain they haven't navigated before.
Sometimes they know exactly what they want to do but are afraid of getting it wrong. Sometimes the business has grown beyond anything they've managed before. Sometimes they need to make a decision that feels significantly larger than the decisions that got them to where they are today.
And sometimes I think we mistake that discomfort for evidence that we're not capable - or it just simply slows us down more than it really should. A good guide can help you understand the terrain and be there to help you get ready for it and support you on your first attempt.
That doesn't mean blindly telling someone, "You've got this." Encouragement without understanding isn't particularly useful. What impressed me about our guide was that his confidence came from experience and observation. He knew the mountain, but he was also paying attention to the people climbing it.
I think the same should be true in business.
There are times when someone genuinely isn't ready for the next step. But there are also times when you can look at a business owner and say: You started here. You built this business to here. Look at everything you've already figured out along the way. You're capable of more than you think you are.
There's another side to being guided, though.
I told our guide what made me uncomfortable before we ever encountered it. I asked questions. I listened when he gave me instructions. And when my own imagination was telling me to be cautious, I had to be willing to trust someone who understood the terrain better than I did. Maybe that's part of what makes someone "guidable." A certain amount of humble confidence. Enough confidence to keep moving, but enough humility to admit when you've never been somewhere before and are looking for support.
The guide couldn't climb the mountain for me. He couldn't eliminate the exposure or make the next step risk-free. All he could do was show me where to put my foot, tell me what he saw, stay close when I needed him, and remind me that I was capable of taking the next step. I still had to take it.
I've been thinking about that ever since we came down from the mountain.
Who helps you distinguish between something you're not ready for and something you're simply afraid to do?