When I first started leading sales training programs, I expected the most impactful moments would come from the frameworks, the methodologies, and the tactics. And yes, those things matter.
- 1. Some of the best salespeople aren’t salespeople.
- 2. Many sales teams show up to training with nerves and skepticism.
- 3. Real learning happens from the inside out—not from lecture slides.
- 4. Everyone dreads role play—until they don’t.
- 5. One-size-fits-all training never works. Ever.
- Build Around The Inevitable
But what has surprised me most over the years is how much the real transformation happens in the subtle, human moments—when a salesperson has a shift in mindset, or when a team finally exhales and starts learning for real.
After leading sales training programs for countless companies, I’ve observed five patterns time and again, across industries, markets, and sales teams of every shape and size.
I’m sharing the five patterns below in the hope that these insights will provide you with key sales training tips to internalize for optimizing your training programs in the future.
1. Some of the best salespeople aren’t salespeople.
That’s not meant to be a slight to those who carry a sales title. In fact, if you’re in a selling role and struggling to hit quota, this pattern should give you hope.
The top-performing “non-salespeople” I’ve seen—consultants, technical founders, service-oriented experts—tend to thrive in sales conversations because they’re not attached to the outcome. They aren’t trying to win a deal. They’re trying to solve a real problem.
They naturally zoom out. They speak the buyer’s language. They focus on the outcome, not the offer. And most importantly, they listen more than they talk.
In one training I led, a client success manager with zero sales experience wowed the rest of the team by offering insightful questions to ask and making helpful observations. He didn’t pitch. He connected the dots between the ideal customer’s struggles and what they truly wanted to achieve.
That’s why so much of my work in sales training is about un-training some of the habits sellers have learned: focusing too much on product features, rushing to pitch, or clinging too tightly to making the sale. Because when you shift the focus to solving problems—and stay curious about the bigger picture—the sale tends to follow naturally.
2. Many sales teams show up to training with nerves and skepticism.
It’s not uncommon for me to walk into a kickoff session and feel the tension in the room (whether it’s a virtual Zoom room or an in-person session). People are guarded. Some look like they’re bracing for impact. Others are clearly wondering, “Why are we here? What did we do wrong?”
And who can blame them? Too often, sales training is positioned as a remedial measure—something to “fix” poor performance. So it makes sense that some sellers come in feeling like they’re about to be put under a microscope.
That’s why one of my behind-the-scenes goals early in a training is to create psychological safety. I want the team to know: this is not about calling you out on poor performance. It’s about equipping you. Supporting you. Helping you succeed on your own terms.
Once that shift happens—once people relax and realize, “Oh, this is for me”—then real learning begins. And the transformation that follows isn’t just professional. It’s often personal.
3. Real learning happens from the inside out—not from lecture slides.
Salespeople don’t need another PowerPoint deck. They need engagement. Application. A-ha moments.
The most effective sessions I’ve led are the ones where the team is actively thinking, not passively consuming. Where they’re analyzing real deals in their pipeline. Rewriting questions. Debating approaches. Testing out different ways of navigating objections.
In one training, a seller realized that by slightly rewording a single discovery question, she opened up a whole new line of insight from her buyer—and uncovered a previously hidden urgency. That didn’t come from a script. It came from her own realization, sparked by real-time feedback.
That’s the magic: when salespeople start seeing connections they hadn’t noticed before. When they move from following a process to owning it.
4. Everyone dreads role play—until they don’t.
Role play is the broccoli of sales training. Everyone knows it’s good for you, but almost no one is excited about it.
At first, people stumble. They freeze. They self-edit. Even seasoned sellers sometimes go blank when they’re put on the spot. But here’s what happens, without fail: once the initial discomfort passes and we debrief afterwards, people begin to see the payoff.
One seller said after a role play session, “This was way more helpful than I expected. I didn’t realize how much I was defaulting to the same question over and over.”
Another said, “Just hearing how someone else handled that part of the conversation opened up a whole new way for me to do it.”
The point of role play isn’t perfection. It’s self-awareness. It’s experimentation. It’s learning how to show up differently, before you get on a real call that counts.
5. One-size-fits-all training never works. Ever.
Every company has a different product, customer, sales cycle, and culture. And every salesperson brings their own strengths, gaps, beliefs, and biases to the table. So why would we assume the same training can work equally for everyone?
Effective training must be customized—both at the company level and the individual level. That’s why I start every engagement with a Sales DNA assessment: it gives us a data-driven view of how each person operates, where they thrive, and where they’re stuck.
In one engagement, we discovered that an entire team was struggling not because of skill gaps, but because of their internal discomfort with discussing money. Once we brought awareness to their preconceptions about money, they became much more effective in their sales calls.
Without that insight, we would have kept throwing tactics at a mindset problem. And nothing would’ve changed.
To assess your salespeople across the competencies scientifically proven to be most critical to long-term success, and to pinpoint the specific growth opportunities to address in training, download a free sample of our Sales DNA Test below.
Download Free Sample Sales DNA Test
Build Around The Inevitable
These five patterns might not show up in every training in exactly the same way. But they’re consistent enough that I now expect them.
More importantly, I build around them. Because sales isn’t just about process—it’s about people. And the more we recognize that, the more effective our training (and selling) will be.
