As a kid, I fell out of more than a few trees. Sometimes the branches just couldn’t hold me—all 75 pounds of energy and curiosity. But I kept climbing, anyway. I’d pretend that tree was my rocket ship, launching me right to the edge of space. I got scraped up sometimes—but I also learned something each time. Growth often works that way.
Years later, in a sales leadership meeting, one of my colleagues asked a question that brought all those memories back:
“This is a safe tree, right?”
That phrase stuck with me—and shaped how I think about trust, performance, and leadership in sales.
What Is a “Safe Tree”?
What he really meant was:
Is this a place where we can be open? Where we can talk honestly—without fear of being judged, punished, or dismissed?
The room gave a confident yes.
Ever since, I’ve adopted the “safe tree” as a leadership mindset, especially in one-on-one meetings with reps. People would say, “This stays between us, right?” and my answer became, “Yes—this is a safe tree.”
That doesn’t mean there are no boundaries. There absolutely are. Heavy issues like harassment, ethics, or legal compliance must be addressed when they arise. But in everyday conversations about performance, development, mindset, or stress, a safe tree culture invites honesty—and that, in sales, is priceless.
When People Feel Safe, They Speak Up
Sales reps are under constant performance pressure. Whether it’s numbers, product changes, or call metrics, the stress is real. And when trust and psychological safety are low, people go silent. But when they believe they can speak openly, they get real—and that’s when leaders can actually help.
Stressed people don’t always ask for help directly. Some try to power through. Others disengage. That’s why we, as leaders, need to read the quiet cues and take the first step.
One way to open that door:
“Hey, I just want to check in. I sense there may be more going on than you’re saying, and that’s totally fine—but if you ever need support, coaching, or just another perspective, this is that space.”
It doesn’t need to be heavy. It just needs to be real.
Leading Through Change with Empathy
Let’s say you’re rolling out a new CRM integration or tightening your call cadence strategy. Some reps pick it up fast. Others struggle—quietly.
You might have a rep who resists logging calls or working in the new interface. On the surface, it looks like defiance. Deep down, it might be discomfort, fear of looking incompetent, or past negative experiences with tech.
Telling someone to “get with the program” won’t resolve resistance. But saying:
“Honestly, I’m still learning this tool myself. I’m thinking about a follow-up training for the team—let’s get it scheduled so we all feel more confident working in it.”
That small act of humility opens doors. Plus, it signals that learning curves are normal—and asking for help won’t hurt you.
We don’t want discomfort or embarrassment being mistaken for feedback. Feedback should guide, not intimidate.
When a Sales Rep Struggles
Let’s say you’ve got a solid performer—we’ll call her Amy—who’s trending below target the past two months. She’s showing up, but something’s shifted. No major red flags, just a slight dip and a retreat into silence. She skips team huddles. She rushes through coaching sessions.
You notice. But instead of applying pressure or jumping to numbers, you say:
“Amy, I just want to check in with you for a few minutes. I’ve seen your performance over the long haul—and this feels a little off. If anything is weighing on you or slowing you down, I want you to know that I’m here to support.”
That’s a “safe tree” moment.
Maybe it opens up a bigger conversation. Maybe she says she’s just in a slump, or maybe she admits to feeling stuck on prospecting strategy. But in either case—you maintained performance expectations while showing humanity.
Holding Space Without Lowering Expectations
Creating a psychologically safe team doesn’t mean abandoning accountability. Sales still has goals. Selling still matters. But safe trees allow people to admit struggles before those struggles turn into churn.
It’s about creating balance:
âś… High standards
âś… Honest conversations
âś… Humble leadership
âś… Flexible support
âś… No judgment for being in process
A rep who feels supported and seen is far more likely to stretch—and less likely to burn out or disengage.
The Power of the Safe Tree in Sales Culture
People don’t grow by pretending everything’s fine. They grow when they feel safe enough to speak freely—and confident that doing so won’t hurt them.
As a sales leader, you might not have all the answers. But you can create a culture that climbs together. A culture that stretches without breaking. One where people feel they can reach—because they won’t fall alone.
Start with one branch. Start with one rep.
And keep making it a safe tree worth climbing.
Harry Spaight is a sales leadership coach and author of Selling With Dignity. He equips organizations to develop sales leaders who inspire and empower high-performing teams.