We’ve all had one of those long, painful conversations with a rep who just doesn’t want to attend training.
Maybe they’re very experienced, and feel like they’ve learned all they need to.
Maybe they’re under quota, feeling the pressure, and don’t think they have time.
Maybe they’ve been overtrained in the past and feel resistant to enablement at this point.
Regardless, it’s our job as sales enablement professionals to find ways to engage our reps in training, without making them feel burnt out, overwhelmed, or irritated.
After nearly 12 years in sales enablement, here are the ten secrets that I’ve learned the hard way. These tips will help get even the most resistant rep to actively engage with the training and resources they need to succeed.
1. Start with trust
Forcing a tool or training won’t work, but reps will listen if they trust you. If your reps are resistant to attending sales training, you need to start by building a better relationship with them.
Take the time to build rapport and understand their perspective. Show them that you’re all in the same boat by only setting up training sessions that will clearly benefit them. Position yourself as a resource, not an enforcer.
2. Be highly selective about training
One of the biggest mistakes in sales enablement is overwhelming reps with too much training — especially at the wrong time.
Plus, you don’t always need to create training. Sometimes, what seems like a training issue is a documentation gap. Sometimes you just need a checklist. Sometimes you just need reps to know where a resource is when they need it.
Also, sometimes you have a change management issue or a product adoption issue, not a training issue. You don’t want to be like the sales enablement team featured in this rant on Reddit: “The trainings will continue until adoption of the expensive thing we bought improves.”
Before rolling out any new training, ask yourselves:
- Is this truly necessary?
- Are we just offering training for training’s sake?
- Is there another, lower-lift way we can get this information to the reps without a training session?
3. Explain the why
Reps are time-crunched. They’re far more likely to engage with training when they understand its purpose. If they see it as just another time-consuming obligation, they will resist. But if they know how it directly benefits them — either by saving them time or improving their results — they’ll be more willing to participate.
When you roll out a new training offering, take the time to explain:
- Why is the training happening? Is it solving a specific problem? Is it addressing a skills gap?
- What’s in it for the reps? Will it save them time? Reduce admin? Increase deal size?
- How does it tie into daily work? Will it help with a frequent pain point? Where will they see the benefits?
4. Keep trainings short, focused and engaging
Every minute a sales rep spends training is a minute they’re not selling. Design your training offerings to maximize your impact with minimal disruption. For instance:
- Keep sessions short — 30 minutes is more than enough for most live trainings.
- If you’re offering self-study resources, consider chunking them down into 5-minute microlearning sessions that reps can find time for more easily.
- Incentivize learning and inspire competition with leaderboards, games, or badges.
- You could even use augmented or virtual reality to make trainings more interactive and engaging.
5. Think carefully about timing
Even the best training will cause resentment if you schedule it at the wrong time. Before setting up a new training session, I’d recommend you:
- Avoid high-stress periods. Don’t schedule training for the last three business days of the month, or the final week of a quarter, when reps are fully focused on making quota.
- Check for competing priorities. Coordinate with other teams to make sure that your trainings won’t happen in the same week as another learning program, leadership meeting, off-site, major product update, compliance training, and so on.
- Provide recorded sessions with self-paced completion options for reps who can’t (or would prefer not to) attend the live session.
6. Personalize training based on skill level
Forcing experienced sales managers into Sales 101 sessions is a recipe for disaster. Here are some tips for personalizing training while still making sure that everyone receives the attention they need:
- Segment your reps by experience level. New hires need foundational training, whereas experienced reps may only need refreshers. At a minimum, offer beginner and advanced tracks to help keep your content relevant.
- Use AI to create individual learning paths for each rep, tailored to their unique skill set, gaps, and role.
- Offer optional training to seasoned reps. Some might not need a given training, but they should still have the opportunity to attend if they see value in it.
- Use data, not self-assessment. Don’t rely on your reps to tell you what training they need. Instead, use performance metrics to determine who should attend which sessions.
7. Consider an “open mic”
Not all training needs to be structured. One of the most effective training formats I’ve used is an “open mic session” — an optional Q&A session hosted by enablement, where reps can ask questions about specific topics.
When I first started these sessions, I was nervous that nobody would show up, or that there would just be awkward silence. In fact, I’ve found that “open mics” tend to be highly engaging — reps almost always have questions, they just need the right forum to ask them.
Pro tip: Don’t record the sessions. The goal is to create a safe space where reps feel they can ask for help without any judgment.
8. Provide one-to-ones for seasoned reps
Your most experienced reps can also be the most resistant to training. They may feel they already know what works for them, and standard training sessions can feel redundant, or even worse, patronizing.
If time and budget allow, one-to-one enablement conversations can be a more effective option:
- You can build trust. If the rep feels heard and understood, they’re more likely to believe that any training you suggest to them will be genuinely useful.
- You can shift their perspective. If you spend the time to show the rep exactly why a new tool or process will help them, they’ll become more open to change.
- You might create an internal advocate. If a seasoned rep sees the value in what you’re offering, they may well influence the rest of the sales team to get on board too.
I once worked with an experienced sales lead who was extremely reluctant to make the time to attend training or learn new tools. I made sure that I sat down with him regularly to understand where he was coming from, what was important to him, and how I could position enablement as a useful resource.
Over time, we got to the point where he would come to me and say, “OK, I heard that there’s a new tool now. Do I need to use it? Because if you tell me to use it, then I’m going to use it.” He knew that if I brought something to his attention it was going to be genuinely helpful and save him time.
Of course, one-to-ones aren’t scalable for every rep — but they can be a high-impact strategy for engaging sales veterans who might otherwise resist enablement efforts.
9. Offer a mix of training modalities
Not all reps learn the same way, so you need to offer different training formats. For instance, consider:
- Live sessions – great for reps who learn best through discussion and peer collaboration
- Recorded sessions – perfect for reps who prefer to complete trainings in their own time
- Short self-paced modules – bite-sized content may work best for busy reps
- Open mics – good for letting reps ask questions in a non-judgmental atmosphere
- One-to-one coaching – may be a better fit for seasoned reps
- Sales simulations – for giving reps a safe space to practice on demand
By offering a blended enablement program, you can cater to different preferences while still making sure that your training fits into a rep’s workflow, rather than disrupting it.
10. Show them the money
Data can be the best way to show reps that your enablement efforts are worth their time. The key is to measure the right metrics — business outcomes, not just completion rates. I’d recommend that any enablement team should be tracking:
- Time to first deal for new hires: If your onboarding program works, you should see reps closing their first deal faster. Compare pre- and post-training data to show improvements.
- Deal size and/or win rate: Show reps that enablement helps close more or bigger deals.
- Sales cycle length: Shorter sales cycles are a sign of improved efficiency.
- Adoption of tools or processes: If you’re training reps in a new methodology or tool, track how many reps then use it and whether or not it impacts their performance.
Without measurement, training risks being seen as a box-checking exercise — when it should be seen as a driver of meaningful improvements in sales results.
Create more engaging enablement programs with the right platform
Overcoming rep resistance and avoiding training fatigue comes down to careful planning, sensitivity to the demands on your reps’ time, and a relationship built on trust. By being selective about your training content and personalizing your enablement program to meet rep’s individual needs, you can win over even the most resistant rep.
Bigtincan can help you get the job done. We use it ourselves! Our Readiness toolkit lets you:
- Provide personalized coaching at scale with AI-based sales simulations
- Use conversation intelligence to help reps adjust their tone and improve emotional impact
- Make more engaging learning content with gamification, interactive quizzes, AI voiceovers, video assignments, and more
- Empower reps to set their own pace with short self-service training modules
- Monitor rep progress with Readiness Scorecards, spot skill gaps and address problems head-on
- Map AI-driven learning paths to engage reps more effectively and improve learner success rates
