For both new and experienced sales managers, investing time in the training and development of your team is always time well spent. I can’t emphasize that enough. If the thought of coming up with sales training ideas sounds daunting for new managers, don’t worry—it’s a topic that still baffles some of the longest-tenured managers in our industry. Trying to decide between potential topics, best practices, and soft skills can be overwhelming without a plan in place to guide your team, and the creation of that plan falls on you as the leader.

In my experience with the sales team at Lessonly, the first step to take is actually backwards. (Hear me out!) Taking a step back to assess your team helps you as a sales manager affect incremental and positive changes that truly help your team, and the company as a whole.

1. Take a step back and get the lay of the land

First things first, open up your calendar and schedule a little “you” time. A couple hours should do the trick, but you want to make sure that you have plenty of time to thoughtfully look at your entire sales process, and how your team works within that process. Put yourself in the shoes of a customer who travels through the entire funnel and try to spot any inefficiencies that could be easily tackled, such as:

  • Outbound prospecting messaging

  • Response time to marketing-driven leads

  • Uncovering need on first calls

Make a list of these easy wins and set them aside for later. Resist the urge to immediately fix your (self-identified) lowest hanging fruit. Keep working on the list and prioritize by expected impact. What you’re doing is identifying levers that you can tweak to refine your sales process, but these don’t become obvious until you’ve had time to sit down and really think your entire sales process.

2. Get in the trenches and make sure you’re on the right track

Once you’ve decided which direction your sales training should go, verify that you’re on the right track. This means getting into the nitty gritty with your reps on a daily basis. This can be accomplished by a host of methods, a few of which include:

  • Shadowing reps as they go through meetings, demos, and other daily activities.

  • Team discussions with members of your sales organization for their input on how they would tackle a certain challenge.

  • Recordings of calls with prospects in different parts of the sales cycle.

Getting in the trenches with your team is incredibly important. It’ll help uncover the the good—and bad—of how they do work every day. When seeing behaviors that work, you can turn them into best practices. When you find things you don’t like, great! You’ve just identified an opportunity for sales coaching to drive improvement. Finding a mix of both good and bad should solidify your assumptions AND help you focus on skill improvements needed at both the team and individual level.

3. Build a training playbook

Finally, it’s time to take the information you learned from your team and turn it into helpful sales enablement. I highly suggest finding sales enablement software that allows you to put this sales training content online. This will benefit the managers, as well as the reps. Let me explain:

Benefits for managers

  • Tracking growth—we, as sales leaders, are driven by numbers! But company and skill knowledge, which is arguably the most important factor of success, is the not usually metric-driven. Using team learning software gives us the ability to track our reps’ growth and needs. From grading reps on video pitches, to reviewing quiz responses and examining what’s being searched for - it’s all data-driven information that leads to honing a focus on  one-on-one development.

  • Quick updating of information—For example, if we have a new competitor that we need to be prepared to discuss, we can quickly and easily build a Lesson about the new company and share it with the team.

  • Repeatability—As much as this all helps your rep productivity, our productivity as managers is important as well! By building a training playbook, sales managers don’t have to teach the same thing every time you bring someone new onto your team. Specific, one-off questions can be quantified in lessons that are easily shared with new reps so your time can be better spent leading.

Benefits for reps

  • Easy access to information—Our team uses Salesforce all day long, and Lessonly is available right within their dashboard. This means, as an example, that our team can pull up a Lesson on the process by which we make contract edits within their account, right next to the opportunity they’re working.

  • Central hub of knowledge—An online sales enablement tool makes it incredibly easy for reps to find information that they need to brush up on. The search function, that takes them to the exact piece of information they need, has been invaluable for their productivity during the day.

Your team wants to be great, and you want to deliver on your target quarter after quarter. It's hard to make the time to step back, develop a plan, and curate the contentI get that. But, I want to encourage you that it's worth it. Taking the time to pause and assess your team’s capabilities and needs goes a long way toward creating your personal training plan playbook. When it’s done right, it provides value that affects not just one or two members of your sales team, but the entire sales department. That’s the type of organizational change that translates into exponential sales growth.


Matt Lubbers is a Sales Director at Lessonly, the leading team learning software. Based out of Indianapolis, Indiana, he spends most of his time - outside of Lessonly - with the love of his life Claire, and a recent addition to their family, their son Teddy.