The Performance Blog

Practical insights on sales leadership, strategy, coaching, and performance. Learn how to build stronger sales teams, create repeatable systems, and turn everyday sales activity into sustainable revenue growth.

When Is the Right Time to Train Your Sales Team?

Sep 02, 2026

 

As a sales leader, I've asked myself this question many times:

When is the right time to deliver sales training?

The funny thing is, there always seems to be a reason to delay it.

January sounds perfect. It's a new year, everyone is energized, and it feels like the ideal time to launch new ideas...But if you're anything like me, you spend November and December trying to finish the year as strong as possible. Between forecasting, planning, budgeting, and trying to hit your numbers, who has time to build a training plan for January?

So then we look at February...But February is a short month. If you're in a business that tracks business days closely, taking salespeople out of the field can feel impossible.

Then March arrives…then Q2 planning…suddenly its summer…and then conference season starts … budget season starts, and before you know it, another year has passed. The reality is, I don't think there is a magical month for sales training. In fact, I think one of the biggest mistakes we make is believing that sales training only happens during an annual kickoff or a large in-person event.

Don't get me wrong. I love sales meetings and in-person training events. They are powerful for team building, collaboration, and introducing new concepts. But sometimes as sales leaders, we expect people to absorb months of development in a packed three-day agenda and somehow retain it all when they return to the field.

The real value comes afterward. Through reinforcement, coaching, accountability and repetition

The challenge, however, is that most sales leaders are wearing a dozen different hats. I've been there! You're managing forecasts, coaching deals, hiring, customer escalations, reporting, strategy, and everything else that lands on your desk.

Building monthly sales training from scratch often feels impossible. And even when you want to invest in development, it can be difficult to find something that fits the budget. We don't want to pull the team out of the field every month. Every hour a salesperson spends away from selling feels expensive...But there is also a cost to not training your sales team.

Research attributed to Aberdeen Group found that organizations using post-training reinforcement saw 34% more first-year sales representatives achieve quota than organizations that did not.

And according to CSO Insights research, organizations with sales training programs that exceeded expectations experienced 11.9% annual sales rep turnover, compared with 19.5% for organizations whose training programs needed improvement.

And I won't even start talking about the cost of replacing a salesperson. If you've ever hired a sales rep, onboarded them, invested months getting them productive, and then watched them leave, you know exactly how painful and expensive that can be .Salespeople are some of the most important people in your organization.

Without new revenue, growth stalls. Without growth, everything becomes harder.

So the question becomes:

Can you afford not to train your sales team?

CSO Insights found that organizations with effective sales training programs achieved win rates of 52.6%, compared to 40.5% for organizations whose training programs needed improvement.

That's not a training statistic, that's a revenue statistic.

Now let me talk directly to the individual contributor for a moment. Don't rely on your company to be solely responsible for your development. I've heard salespeople blame their organization for their lack of growth. Don't be that person! Invest in yourself.

  • Read books.
  • Listen to podcasts.
  • Take training.
  • Find mentors.
  • Sharpen your skills.
  • Take ownership of your future.

The best sales professionals I've worked with never waited for permission to improve. They invested in themselves because they understood that their career was ultimately their responsibility.

For sales leaders, I still don't believe there is a perfect month for training. What matters most is creating a culture of ongoing learning, reinforcement, coaching, and accountability.

AI is already changing how sales professionals need to show up. Buyers are more informed than ever...Information is everywhere. The sales professionals who succeed in the future will be the ones who bring insight, value, strategy, and guidance. As leaders, it's our responsibility to help our teams develop those skills.

If you're looking for a cost-effective way to build the foundational skills of a high-performing sales professional, I'd encourage you to take a look at Pivot2Performance.I created it because I know firsthand how difficult it can be to find affordable, practical sales training that leaders can actually implement and reinforce with their teams.

Because there may never be a perfect month for training. But there is never a wrong time to help your team get better.

 

About Pivot 2 Performance 

Pivot 2 Performance was created to help sales professionals and sales leaders build the foundation behind the numbers  from daily activity and weekly rhythm to pipeline discipline, accountability, value, and more.

It's practical, affordable, online training you can work through at your own pace.

Explore  Pivot 2 Performance 



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