A story about asking better questions, told from a nine hour hike in Banff.
I used to ask one question before every walk. “What’s the weather?”
I thought I was gathering information. I was looking for an excuse. Too chilly. Too windy. Rainy. Don’t feel like it.
The Visit
On a recent visit to a relative, an 80 year old mentioned how much she wished she had made a visit to her high school best friend. They had not seen each other in two decades.
As a coach, I want people to see possibilities. So I told her, “Why not? You can go.”
She was excited. That excitement motivated her to work out daily, to wear her back brace, to prepare. She even agreed to a wheelchair to navigate airports. And we made the journey.
Then I saw the place where her friend lives. It looked sad. Windows closed. Gray walls. Not a single plant. No activities like chair yoga. No uplifting music. A TV showing food none of the residents could eat. No sense of community. Only very few chatted.
I wondered why it is this way. Someone needs to make it a better place.
Her friend was happy to see her. She said she even agreed to change clothes for the occasion, which she rarely does.
I saw a striking difference between these two 80 year olds. One wants to travel, walks when possible, lives in her own home, and cooks for herself. The other can walk and chooses the wheelchair because it is more comfortable. She stays in hospital garb because it is more comfy. Somewhere along the way, she made that decision, or let others make it for her.
That’s when it hit me. Comfort was what separated these two women.
The trip got the wheels turning in my relative’s head. She committed to working out, to being fit, to choosing a different lifestyle so she can continue on her own.
And comfort was the reason I asked about the weather. The question was there to answer my wish of not going anywhere.
Asking Better Questions: A Different Ask
After what I saw, I decided to make a greater change.
At first, I asked, “Can I hike a mountain?” The answer was, “Of course not.”
I had to ask differently, and be mindful. I changed it to “How can I hike a mountain?” And I picked one: Banff, to the teahouse and beyond, all the way to Victoria Glacier. A nine hour hike, regardless of the weather. Rain, icy path, stones, pebbles, elevation.
That question compelled me to prepare. To join a gym. To get a coach. To work out daily for four months. To pack with intention.
Of course, I want comfort. I love to travel, and my favorite city was always Manhattan, for the food, the crowd, the shops. We can add comfort to what we are doing. I packed veggie wraps, hot tea, and extra socks.
The Belt

The day before the trip, I thought I would swing by REI and grab a pair of hiking poles. How hard can that be? I found a wall of poles that ranged from $60 to over $200. They’re just sticks, not even cool to carry! I was sure I didn’t need them, until I discovered I did.
Then the backpack. I was going to use an old one, but thought against it. I picked a plastic one, in case someday I hike with my photography gear. If it sat in there under a torrential rain, it would stay dry. For this trip, the gear stayed home. I didn’t want to burden myself. It is my first hike! I want it humane!
I was trying to be practical instead of being informed.
Finally, I asked the employee what he thought of my bag. What I was really looking for was validation. Something like, “Yes, this is a great one.”
His answer: “It is good for about four hours.”
“How does the bag know?” I asked.
He paused for a while, trying to keep a straight face. Then he said, “Your back. It would be hard on your back. The belt relieves that.”
I got one with the belt.
A few hours into the hike, I put the belt on. Suddenly the weight on my back dissipated, and it felt as if I were only wearing a belt. I picked up my speed and felt liberated.

I asked for validation. I got information. The ask matters.
I made it.

This week I returned from that intense hike, like nothing I have ever done before, because I asked the same question differently, with an intention.
I returned inspired, because I saw things that would never have been possible from the warmth of my couch.
There were people along the trails from around the world. We exchange a greeting. Occasionally we ask which trail they loved. People are friendly, and they come from all walks of life and all ages. Nothing matters except how far the final destination is. We joke about whether Starbucks is around the corner. “Ooo, they just sold out,” one said. Another said, “Yeah, it is about 200 meters, so keep going.”
You know you are never alone.
The Art of the Ask Starts With Asking Better Questions
I don’t keep a bucket list. I have a reverse bucket list: what is it that I must do next? Be fit. Walk. We use it or lose it.
Next, I am preparing to hike Mount Fuji.
We need to be mindful of the outcome we want, because in the way we ask, we have already made a decision.
We ask, “Is it time for lunch?” “Is it time to rest?” because we are ready for those.
Is it time to walk? To challenge our minds? To push beyond our limits?
I still ask about the weather. I used to ask to decide whether to walk. Now I ask to decide what to wear.
Asking better questions: three places to start
- Change “Can I?” to “How can I?” The first invites a no. The second starts a plan.
- Before you ask, name the answer you are hoping to hear. If you already have one in mind, you are looking for agreement.
- Ask the person who knows what they would choose, then listen to the reason.
Why asking better questions works
Asking better questions changes what happens next. A question that expects a no ends the conversation. A question that starts with how sends you looking for a way.
Asking better questions also changes who you hear from. The store employee had the answer the whole time. It took one honest question to get it.
Leaders can use this with their teams. Asking better questions in a meeting sounds like this: How can we make this work? What would you choose? What am I missing?
About those poles: I wrote a poem. Read No Poles for Me.

Leila Kubesch is a keynote speaker, speaking coach, and author. Her keynote, The Art of the Ask, shows leaders and teams how to make the ask with confidence. To bring Leila to your event, write to Leila@LeilaKubesch.com.