If you’ve ever rolled out a sales training program that didn’t quite stick, you’re not alone. I talk to sales leaders all the time who’ve invested time, money, and energy into training—only to find their teams slipping back into old habits a month later.
It’s not that the training was weak. It’s that changing behavior is hard. You’re balancing revenue goals, time pressure, and competition while trying to build your sellers’ skills and keep them motivated and aligned.
Here are 10 of the biggest sales training challenges I hear from sales leaders today—and some practical ways to overcome them.
1. Getting Sales Training to Stick
The challenge: After a great training session or workshop, sellers are fired up—for about a week. Then they slip back into old habits.
Why it happens: New skills fade quickly without ongoing sales coaching and reinforcement.
How to fix it: Treat training as a process, not an event. Build in regular reinforcement, manager coaching, and real-world practice to strengthen new skills.
2. Aligning Sales Training with the Sales Process
The challenge: Training concepts don’t match the organization’s sales process or methodology.
Why it happens: Training is not aligned with business strategy and is often delivered in isolation.
How to fix it: Connect every training initiative directly to broader company objectives. Make sure your sales process, CRM stages, and training language are consistent. Reinforce terminology and behaviors in team meetings, pipeline reviews, and performance evaluations.
3. Customizing for Different Experience Levels
The challenge: One-size-fits-all training rarely fits everyone, but you need sellers to share a common language and consistent sales process.
Why it happens: It’s easier to roll out a single program than to tailor it to different roles or skill levels.
How to fix it: Use sales assessments to identify strengths and skills gaps, then design training that addresses those development needs. Reframe training for experienced sellers as an opportunity to retire outdated approaches and break bad habits.
4. Measuring Impact and ROI
The challenge: It’s hard to prove training is paying off.
Why it happens: Many programs focus on participation metrics (“who attended”) instead of performance metrics (“what changed”).
How to fix it: Define success upfront to link training to business outcomes such as improved win rates, shorter deal cycles, or higher average deal sizes. Track and measure sales skills, training adoption, and performance indicators of training success at every key milestone.
5. Getting Manager Buy-In and Participation
The challenge: Sales managers are too busy to reinforce new skills.
Why it happens: Training often overlooks managers or doesn’t equip them to coach effectively.
How to fix it: Train sales managers first. Give them the skills to develop their teams effectively and coach new behaviors. Hold them accountable for reinforcement as part of their leadership role, not as an add-on.
6. Adapting to Remote and Hybrid Sales Teams
The challenge: Remote or hybrid teams make training less interactive and harder to observe in action.
Why it happens: Facilitators lack the ability to deliver engaging and effective virtual programs.
How to fix it: Make sure your sales facilitators can create an engaging experience and mix formats—live virtual workshops, peer breakout rooms, microlearning, and role-plays.
7. Balancing Sales Skill Training with Product Training
The challenge: Sellers know the product but struggle with the core sales competencies of consultative selling: building trust, discovery, positioning, and selling with value.
Why it happens: Product knowledge is easy to teach and measure, while soft skills take more time and practice.
How to fix it: Balance the three types of sales training: sales process, sales skills, and product knowledge. Pair product training with customer-centric scenarios. Teach sellers to connect features to business outcomes and to ask probing questions to uncover customer needs.
8. Keeping Training Fresh and Continuous
The challenge: Sales environments change faster than most training programs.
Why it happens: Training is often treated as a one-time rollout, not as an on-going process.
How to fix it: Establish a consistent, well-timed training cadence of product, sales skills, and process with refreshers, digital reinforcement, and skill challenges. Keep content updated with market changes and competitive shifts.
9. Creating a Coaching Culture
The challenge: Teams see training as a checkbox, not as part of how they work.
Why it happens: Leaders don’t model continuous learning, and coaching isn’t built into daily routines.
How to fix it: Make sales coaching visible and valued. Combine live coaching and digital reinforcement to ensure sellers understand and implement newly learned skills. Use new AI sales tools to personalize feedback and allow managers to coach more effectively.
10. Managing Time Pressure
The challenge: “We don’t have time for training.”
Why it happens: Quota pressure often pushes development to the back burner.
How to fix it: Integrate training into the work itself. Use real deals as learning examples, embed short lessons into sales meetings, and connect skill improvement to faster deal cycles and higher win rates.
The Long-Term Value of Sales Training
The best sales training doesn’t just transfer knowledge, it transforms behavior. For that to happen, sales leaders need to view training as an ongoing, integrated part of sales operations. When managers reinforce it, metrics track it, and sellers see its value in their daily work, training becomes what it’s meant to be: a competitive advantage.
Find out how sales training from The Brooks Group can help improve your team’s selling skills and training ROI.
