Why Don’t More Leaders Ask for Help?

Despite their track records, many leaders still associate asking for help with vulnerability or failure. Leo sees it firsthand.

He often opens sessions by asking people how asking for help makes them feel. Using a live word cloud tool, he gathers answers from across the room.

“Look at the words they selected: awkward, troublesome, uncertain, anxious, stupid, humbled, weak… overwhelmingly, the feelings that people have about asking for help are not great.”

“You may not feel this way, but many of your employees—and even some on your senior leadership team—do.”

Peer Influence Starts Early

Leo illustrated how early these dynamics take root with a personal story about his daughter, Taylor, at age four.

At a Halloween event, a woman dressed as a witch entered the classroom, causing panic. Kids were crying and running—until Taylor stepped forward and said:

“It’s okay. She’s not real. There’s no need to be afraid.”

“The first kid who starts to cry triggers the second, triggers the third, and it spreads like wildfire,” Leo explained. “We look to one another in those moments of fear and uncertainty. We always have. And we continue to do it today as adults.”

It’s a powerful parallel to what happens inside companies during moments of change.

“They engage in sensemaking exercises in the same way those kids did in Taylor’s classroom… when these sensemaking exercises take place, you want those ambassadors in those conversations.”

From Peer Influence to Peer Advantage

The people we surround ourselves with have tremendous influence over our behaviour. That’s peer influence. But when we’re intentional, selective, and structured in how we engage those people? That’s when we experience something else:

“Peer advantage is what’s realized when we’re more selective, strategic, and structured about the people who surround us.”

“It’s what you do when you hire the people in your company… it is certainly what you do when you select a peer group to be part of, and that they select you.”

What Great Teams Do Differently

Whether you’re running a business, a large corporate team, or a not-for-profit, help-seeking isn’t optional. It’s essential.

“The greatest teams see asking for help as such an incredibly powerful part of their culture and who they are.”

Leo points to two examples of high-performance, help-seeking cultures:

• The UConn Women’s Basketball Team:

“Everything from strength training to shooting to playing defence… the communication level and how they trust one another, and how they lean into the roles that they need to play to be successful on that team, becomes really important.”

• MullenLowe (Global Advertising Agency):

“Sometimes things can get very passionate, very combative… but they’re not fighting against one another—they’re fighting for the best idea.”

The Help Triad: A Better Team Model

In traditional hierarchies, help flows top-down. But Leo proposes a flatter, more dynamic structure—what he calls the Help Triad:

“Leader is a part of the team, not a part from it…we are all in this together, and that we are all about asking each other for help, and that’s how we’re going to be the most effective.”

It’s not about the title. It’s about shared ownership and trust.

One Game That Brings It All Together

Leo shared an exercise he runs in leadership sessions called Toss Me Some Feedback. A blindfolded teammate tries to land beanbags in a cornhole target. In the first round, they get no input. The next, yes/no questions. The final round is open collaboration.

“When we have a collective goal and when we’re all bought into wanting to achieve that goal and we trust one another… we need to rely on each other to make that happen.”

“When people offer help, ask for help, or give and take feedback, it’s done from that place of caring… in service of our craft and our customers.”

How to Ask for Help Without Feeling Small

Sometimes the hardest part is just saying the words. But a subtle shift in framing can make a major difference.

“You can say, ‘I need help,’ which emphasizes you, your need… or you might express it a different way: ‘I want your help.’”

“It’s not just about you anymore. It’s about the other person. It’s about expressing it as an invitation.”

Final Word: Who You Surround Yourself With Matters

Leo ended the session with a quote from poet Sekou Andrews:

“Surround yourself with communities in which you feel small, because they look at you like a giant.”
— Sekou Andrews, as quoted in What Anyone Can Do by Leo Bottary

“As they’re meeting you and learning about the gifts that you offer, they’re thinking: ‘Wow. Glad you’re joining us.”