3 Leadership Trends That Derail Sales Behavior Change

I’ve seen organizations put significant thought and effort into a sales transformation. They’ve aligned on the strategy, invested in training, introduced new tools and expectations, and communicated why the change matters. Leadership is aligned on the need for change, and there’s real energy around it.

Then everyone goes back to work.

A few months later, some sellers are applying the new approach consistently, but many others have fallen back into old habits, with managers reinforcing the target behaviors to varying degrees. Other priorities have inevitably surfaced, and while leaders may see pockets of progress, the broader change in performance they expected hasn’t come through.

When that happens, it’s tempting to question the initiative itself. Was the training effective? Was the methodology right? Did people buy into the change?

Those are reasonable questions, but in my experience, there’s another place leaders need to look: What happened after everyone went back to work?

That space between the strategy and what people do in the course of a routine day is where behavior change either takes hold or starts to break down.

Our recent research gives us a clearer view of that challenge. RAIN Group’s 2026 sales challenges and priorities research found that 47% of organizations reported growth in qualified pipeline, but only 40% reported increased wins and 37% reported increased quota attainment. At the same time, Alchemist's 2026 leadership research found significant challenges around manager capability, coaching, accountability, and sustaining behavior change.

We brought the two studies together to examine what may be contributing to the gap between strategy and execution. Three leadership trends stood out.

1. Managers Are Expected to Drive Performance Without Being Fully Equipped to Do It

We ask a lot of frontline managers. They’re expected to deliver results, develop people, coach performance, reinforce organizational priorities, manage change, and often continue contributing directly to the work of the team.

Yet many organizations are struggling to prepare them for that role.

In RAIN Group’s research, 80% of respondents said developing sales managers was very or somewhat challenging, while 73% said the same about coaching the sales force effectively. Alchemist’s research found similar challenges with building managers’ coaching capabilities and helping managers coach their direct reports for performance and skills.

I’m particularly passionate about this because I think we sometimes underestimate how different management is from the role that came before it. We promote someone because they’re a strong seller or functional expert and then expect them to step into a job that requires a much broader set of capabilities.

I see management as both a skill and an art form. Managers need to understand people—how to motivate them, develop them, coach them, and hold them accountable. They need leadership acumen and, depending on the role, business and financial acumen as well. We can’t take for granted that someone walks into the role with all of those competencies already developed.

This becomes even more important during a sales transformation. A manager can understand a new methodology or process and still not know how to coach someone else to apply it in a live opportunity. If we change what we expect from sellers without also changing what managers inspect, reinforce, coach, and recognize, there’s a break in the chain.

So when I’m working with leaders on a change initiative, I want us to answer two questions together: What do sellers need to do differently, and what do managers need to do differently to help them get there?

Define the behaviors managers should coach. Give them the skills and tools to do it. Make coaching part of their responsibilities and operating rhythm rather than something they’re expected to fit in when time allows.

2. Unclear Expectations Create Inconsistent Execution

Accountability comes up in nearly every conversation about performance and change. Leaders want more of it, managers are expected to create it, and teams and individuals are expected to demonstrate it.

But before we ask people to be more accountable, we need to ask ourselves how clearly we’ve communicated what that means.

In Alchemist’s research, 63% of leaders reported difficulty maintaining accountability and execution, 71% struggled with cross-functional alignment, and 63% found it difficult to align stakeholders on what effective leadership looks like. Organizations that consistently used a leadership framework were 28% less likely to struggle with accountability and execution.

The implication is that alignment has to get much more specific than agreeing on the outcome.

I’ve seen leaders fall into the trap of thinking that once we’ve set the vision and communicated the goal, our work is largely done. When you’re trying to drive meaningful change, though, there’s another side to leadership: translating that vision into execution. That requires getting tactical about what people will need to do differently to create measurable change.

Think about a sales organization that wants sellers to have more valuable conversations with customers. Everyone can agree with that objective, but what does it mean in practice?

What should a seller do differently in discovery? What should a manager hear in a call or see in an opportunity review that tells them the approach is being applied? What does good execution look like, and how will you know it when you see it?

Those questions move us from a broad expectation to observable behavior. Once we’ve done that, managers have something concrete to coach, people know what they’re working toward, and the organization has a way to determine whether the change is gaining traction.

I’d also caution against trying to change too much at once. It’s easy to create a list of 10 things we want people to do differently. It’s much harder for someone to consciously practice 10 new behaviors until they become habits, and that’s where I’ve seen many transformation efforts fall apart.

3. One-Off Training Doesn’t Produce Sustained Behavior Change

Alchemist’s research found that 72% of leaders consider sustaining behavior change challenging, while 64% struggle to provide targeted behavior reinforcement and practice at scale.

Earlier RAIN Group research also points to the importance of managers in sustaining sales performance. Top-Performing Sellers are 83% more likely to have extremely or very effective managers, and top-performing sales managers are 46% more likely to have received extremely or very effective training.

Sustaining behavior change means helping people continue to apply what they’ve learned once they return to the demands of the job. A difficult customer conversation happens, the quarter is coming to a close, a deal is at risk—under pressure, it’s very easy to return to whatever has felt familiar in the past.

That doesn’t necessarily mean someone rejected the training or doesn’t want to change. They may need more practice and coaching, or there may be something in the work environment making the new behavior harder to apply.

Leaders need to view reinforcement as part of the implementation itself.

With customer teams, for example, we often build in touchpoints at 30, 60, and 90 days after an engagement. We go back to the behaviors we wanted to change and ask: Are we getting traction? Where are we seeing it? Where aren’t we? And, importantly, what’s getting in the way?

In one case, we found that the process itself was working against the behavior. The CRM didn’t require sellers to complete the new behavior, so we built it into the system. Once the process reinforced what we were asking sellers to do, adoption increased immediately.

In another situation, sellers understood the behavior and were committed to it but struggled to apply it when conversations became more complex or difficult. We added more practice around those situations and paired struggling sellers with peer coaches who could provide live feedback after sales calls.

Those follow-ups give leaders a chance to make adjustments while the change is still taking hold. Rather than waiting six or nine months for a lagging business indicator to tell us whether the initiative worked, we can track the behaviors along the way, address blockers, reinforce progress, and share examples of what’s working.

Make Behavior Change Part of How Sales Is Managed

When I look across these three trends, I see three interconnected problems.

Leaders set a strategic priority, but someone has to translate that priority into the way work gets done. Managers have to understand the behaviors that support it and be prepared to coach them. Sellers need opportunities to practice those behaviors in real situations. And leaders need to stay close enough to the change to see where it’s working, where it’s getting stuck, and what needs to be adjusted.

If you’re working through a sales transformation now, I’d look at three areas:

1. Enable: What do our managers need to coach for, and have we prepared them to do it?
2. Align: Have we defined the desired behavior clearly enough that people can apply it and managers can recognize it?
3. Reinforce: What are we doing after training to help that behavior become part of everyday work?

Behavior change rarely happens all at once, and I don’t think leaders should expect it to. What we can do is create the conditions that make the change easier to understand, practice, reinforce, and sustain—and give our managers a much stronger chance of turning strategy into consistent execution.