How to Run Sales Trainings Your Reps Will Actually Enjoy


Have you ever presented something to help level up your team and just saw blank stares looking back? Or saw nothing but people looking down at their phones?

How about when you ask…”are there any questions?” and all you hear is crickets?

In-person training is hard enough, but now that we’re doing everything virtually, we have to deal with team members working on their second screen or giggling while messaging their team members through slack.

Unfortunately, this is the reality of most sales training, and every sales leader and enablement manager is looking for ways to change that.

Luckily, your sales training doesn’t have to put your team to sleep.

Step 1: Tell Your Team the Why

Ask yourself, why is your team in the room today?

Why should they take 30 or 60 minutes out of their day to listen to this enablement?

Why is it important to their job, their quota, the company, or themselves?

It’s important to set the stage and tell your team the WHY behind what they are learning before you teach them anything.

There are many ways to do this, but here are a few examples:

Send out a teaser email with the why, but don’t share what they are actually going to be learning.

The earlier you get buy-in from your reps, the more engaged they’ll be on the day of. No one wants to lose a day of work and potential profits, so make it clear how this training will help them in the long run.

“What we are going to learn in Tuesday’s training will provide you with the secret sauce for how you can get promoted from BDR to AE in the fastest time possible.

Looking forward to seeing you all then!”

Start your training or enablement with a story.

Stories are always a great way to create engagement. It’s why so many memorable speeches and Ted Talks start with a story. Plus, it gives you a great way to share the why in a real-world scenario.

“When I was an individual contributor, I was the second-best rep on the team for years. But when I learned this, I quickly became #1, and no one could beat me on the dashboard no matter how hard they tried.”

Start with real facts and figures (bonus points if they are from your team).

Statistics can be a great way to quickly show the value the training can have on your rep’s real-world performance and earnings.

“I did an analysis of all our team’s data and learned that the individuals that have at least 12 touch-points on their leads had an 80% higher conversion rate than those who didn’t.

Do you know how many touch-points you have on average on your leads?”

Start with a quiz.

An interactive platform like Kahoot or even a more simple google form can be a great way to get some feedback and interaction before your training. This can also give you a baseline of people’s understanding and get them excited about the topic.

“Before we get started today with our social selling training, I want to start with a Kahoot interactive live quiz filled with facts about social media and the power of social selling.”

Step 2: Less Is More

If you have a training or enablement in mind, consider how much is digestible in one sitting.

Your reps will get the most value from your training if you only have 1-2 main takeaways or new strategies that they can try right after they walk away from the session.

If you review your content and see more than two, consider breaking it up into multiple sessions over a couple of weeks. This will give your team a chance to digest what they learned, try something new, and add to it the following week.

The less is more rule also applies to the visuals of your presentation. Limit the number of slides you have and the content on those slides.

The most effective sessions are often 10 slides or less and contain images and bullet points rather than full sentences.

Step 3: Eliminate Distractions

The number one reason sales trainings are so difficult is because of the many distractions around us.

This is perhaps the easiest (and more important) change that needs to be made to ensure an effective sales training. In our virtual world, this means cameras on, and make it clear that your expectation is that they are not multitasking.

When we go back into the office, whenever that may be, it means laptops closed, and cell phones away until the session is done.

This may not always be possible when customer fires are coming our salespeople’s way, but it’s important to set expectations early and enforce them as needed to keep people from being distracted by devices.

Step 4: Make it Interactive

If you make your trainings a two-way conversation rather than one-way, your team doesn’t have a choice but to pay attention.

There are many different ways to make a sales training interactive, but here’s a handful of examples:

Ask questions throughout

Consider having mini-quizzes, 1-3 questions every few slides, or call on people throughout your presentation.

Ask open-ended questions such as, “Jim, what point resonates with you the most on the previous slide and why?”

By asking questions frequently and randomly, your team will feel on the edge of their seat that they may get called on and will need to have an answer. This indirectly increases your team’s attentiveness and overall engagement.

Add exercises for breakout groups

Try adding some exercises or practice work for your team to work on in breakout groups.

For instance, if you’re running an enablement for BDR’s on a new product, consider breaking them out into groups of 2-4, and get them to write 1-2 outbound emails and a cold call script about the challenges the new product can solve.

Practice new techniques together

When teaching new sales techniques and tactics, like an upfront contract or a new cold-calling script, consider doing a short training (5-15 minutes) followed by a group practice session.

For example, when teaching the upfront contract, consider doing a 10-minute training on the technique, and then 20 minutes where each person on your team practices in front of the others.

Instead of providing feedback yourself, get your team to provide feedback to each other.

Step 5: Ensure it Sticks

You’ve just run a 30 minutes training…now what?

Often sales leaders or sales enablement managers run a training and just expect their team to apply it immediately going forward. Unfortunately, the reality is that people don’t like change. Running a successful sales training is just the first step. Getting your team to implement the training is the next challenge.

Provide homework or a follow-up training after the fact to ensure your team applies what they learned.

Here are a few ways to ensure it sticks:

Provide homework

Consider giving out practical exercises after the training that your team members have to submit later that week or the following one.

By providing homework, you ensure your team members are practicing what they learned immediately while it’s still fresh in their minds.

For example, if you were teaching best practices on writing LinkedIn InMails, consider having each team member send 10 InMails and submit their best one to you to review.

Pair up your team members for practice

Consider pairing up your team members to practice their new skills. By pairing up your team members, they will feel accountable to practice and show their teammates their skills.

For example, for a Sandler upfront contract, you could pair up your team members and get them to review 3 calls from their partner where they tried the upfront contract. You could also ask them to provide written feedback for each call reviewed.

Do a follow-up training and roundtable a week later

Another great way to get your team to practice is to host a roundtable and breakout session a week later.

Let everyone know after the training that they should bring their wins, failures, and learnings to a roundtable discussion next week. By doing this, you will celebrate the team wins together and promote learning from each other’s failures.

To take this one step further, add an interactive element to the roundtable where your team practices what they learned the week before with each other.

For example, if your team was learning and practicing how to run an effective pricing call, ask your team members to each share one learning from practicing it that week.

After everyone gets a chance to share, consider asking some volunteers to share their calls with you, both wins and failures, and listen to them as an entire team.

Get your team to provide feedback as a group.

My Challenge

When you think back to your last training — whether you ran it or it was run by someone else — was your team engaged?

Did they apply what they learned?

Did you see the change you were hoping for?

If the answer isn’t yes to all of the above, I urge you to try something new.

Here’s my challenge to you. Determine what your next training is, and try incorporating elements from each of the above sections — Tell your team the why, less is more, eliminate distractions, make it interactive, and ensure it sticks.

If you notice a change, please share what you did with our community so we can all become better educators and enablers to our future sales leaders.


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