Make It Personal: Why Sales Transformation Requires More Than Just Training

Sales training should lead to transformation, but most of the time, it doesn’t. We spend billions equipping reps with new techniques, but when it’s time to use them, the behavior never changes. Why?

Because training focuses on the room, not what happens after.

The real challenge isn’t getting people to learn. It’s getting them to change. And that only happens when it’s personal. Not inspirational. Not entertaining. Personal.

Let’s define what “personal” really means and explore how to build a system where reps are supported, not just trained.

Tom dives into this very concept in the video below:

Why Most Sales Training Doesn’t Stick

Training sessions are usually a one-and-done experience: a few high-energy hours, breakout exercises, maybe some applause. But what happens when everyone returns to their territories?

Reality.

Teams are swamped with deal pressure, internal fire drills, and ingrained habits that feel safer than any new idea. By the end of the week, the glow of the session is gone, and the old behavior is back.

The problem isn’t the content. It’s the context. Sales and account teams don’t live in a lab. They live in complexity. And in that complexity, training without reinforcement is forgettable.

To make training stick, reps need:

• A personal reason to change: If the new skill doesn’t make their job easier, safer, or more successful, it won’t stick.
• A structure for daily application: Change isn’t an event. It’s a process. If it doesn’t show up in Monday’s 1:1 or Wednesday’s deal review, it’s not real.
• A system that meets them where they are: Different reps have different gaps. Mass instruction without individual coaching misses the mark.

Training should be the beginning of a behavior shift, not the peak of it.

What It Actually Looks Like to Make Change Personal

Personal change means one-to-one. One leader working with one individual on one real deal. Not in a training room. In the moments that matter: before the call, during the deal review, and when they’re actually figuring out how to use the skill.

Here’s what makes it stick: each team member has to connect the new skill to something that matters to them. Usually that's purpose-driven: knowing they're helping the customer solve a real problem, not just moving a deal forward.

When that happens, the new behavior stops being a task and starts being natural.

Now let's get tactical.

Imagine you’ve just trained your team on a new discovery model. It’s clear, practical, and rooted in solid methodology. But theory doesn’t drive results. Execution does.

So here’s how to personalize that path to adoption:

• Before the call: A manager meets with a rep to strategize. “Where in the conversation do you think the customer usually holds back?” “What could you ask differently this time?”
• During the deal review: The manager and rep replay the call. They evaluate one moment, not the whole conversation, where the rep could have dug deeper.
• In a team meeting: Another rep shares how a question from the model unlocked a customer’s real concern. That win becomes fuel for others.
• Across time: The same skill gets revisited. The same language gets reinforced. And most importantly, the rep starts to own the behavior, not just remember it.

This isn’t abstract. It’s visible, daily, and tied to real outcomes.

Personal doesn’t mean coddling. It means making development feel relevant. It means building a system where change is the norm, not the exception.

When that happens, training doesn’t fade. It sticks. And more importantly, it spreads.

Coaching Is the Core, Not the Follow-Up

Training creates awareness. Coaching creates accountability. 

Reps may nod along in a session, but real adoption happens in follow-up:

• Pipeline reviews where managers ask how they'll use the new skill.
• Call planning conversations before the meeting happens.
• Post-meeting debriefs where the rep reflects on what worked.

Coaching is where new behaviors are tested, corrected, and internalized. It’s where the rep gets help navigating the emotional and tactical challenges of doing something new.

But coaching only works when it’s consistent and calibrated. Without a shared standard, coaching becomes subjective. One manager coaches to best practices. Another coaches to personal preference. Reps get mixed signals, and momentum stalls.

Great coaching isn’t a checklist. It’s targeted, deal-specific work:

• Target the skill: Is the rep struggling with discovery? Qualification? Positioning? Get specific about the gap.
• Connect to a real deal: What opportunity this week can serve as the practice ground? Real stakes matter.
• Run the play together: Collaborate on language, approach, timing. Don’t just tell them what to do.
• Review the outcome: What worked? What didn’t? Why? Turn the experience into learning.

This isn’t activity management. It’s capability development, one rep at a time.

Build Practice Into the Daily Workflow

Reps need a place to fail safely before they're in front of a buyer. That means creating opportunities to practice new skills in a low-stakes environment where they can try, fail, adjust, and try again.

When practice is integrated into the daily workflow instead of saved for a quarterly training, reps build muscle memory. They get comfortable with the discomfort of doing something new. And when it's time to perform, the new behavior feels natural.

Progressive practice matters too. You don't throw a rep into a full discovery call on day one. Start simple and build:

• Core messaging and positioning
• Objection handling (one objection at a time)
• Full conversational fluency and discovery
• Complex multi-threaded opportunities

Mastery happens in stages, not all at once.

How to Build a Coaching Culture

A coaching culture starts when managers see themselves as enablers of change, not enforcers of metrics. That shift doesn't happen by accident. It requires intentional design.

• Reframe the manager's role: Coaching isn't extra. It is the job. That means protecting coaching time from getting eaten by reporting, firefighting, and back-to-back meetings. If your managers spend 80% of their time in administrative work and 20% developing people, you've built a system that resists change by design.
• Make coaching visible: Embed coaching sessions into team rhythms and reviews. Track coaching conversations the same way you track pipeline activity. When coaching is measured and discussed, it gets done. When it's implied but not tracked, it gets skipped.
• Equip managers with the right tools: Too many managers coach from gut instinct or personal style. That creates inconsistency. Give them tools that help them diagnose skill gaps, deliver feedback that sticks, and calibrate coaching to best practices.
• Remove the friction: If your CRM, your meeting cadence, and your reporting structure make coaching hard, it won't happen. Build coaching into the systems your managers already use. Make it the path of least resistance, not an aspirational add-on.

When coaching becomes a shared expectation across the organization, change scales. When it's treated as optional, it dies.

If Leadership Isn't Aligned, the Middle Won't Hold

If frontline managers are coaching one way and execs are pushing another, reps will follow the louder signal. Usually, that's the one tied to metrics and compensation.

Real alignment looks like:

• Leadership speaks the same language: The concepts in the training show up in town halls, pipeline calls, and strategy decks. Not just in the sales org, but across the company.
• Reinforcement is cross-functional: Ops, enablement, and sales leaders reinforce the same behaviors. When the VP of Sales says one thing and the VP of Operations says another, reps notice.
• Sustainment is funded and prioritized: Coaching time is protected. Certification processes are maintained. Win stories reinforce the shift. This isn't treated as a nice-to-have; it's a core function.

Misalignment kills momentum. If an account team sees leadership dismissing the very behavior their manager is coaching, it signals one thing: this isn't real. This is the flavor of the month. And they stop investing in the change because they know it won't last.

Alignment means the top and bottom of the org are rowing in the same direction. It means reps feel safe to invest in the change because they see everyone else investing too.

To Make Change Personal, Leaders Have to Go First

The core idea behind real transformation? It has to be personal. One rep at a time. One behavior at a time. And that shift only happens when leaders take ownership, not just of strategy, but of culture.

That’s what Catalyst is built to do.

Catalyst equips your senior leaders to champion the same change you’re asking reps and managers to make. It bridges the gap between training and transformation by aligning leadership behavior with frontline execution.

If you’re serious about building a system where training sticks and change scales, start at the top.

Let’s talk about how Catalyst can help.