Straight from the Experts: 6 Simple Tips for Training Your Newly Remote Sales Team

Before we talk about enabling your remote sales team like it’s nobody else’s business, we’ve got two things to tell you:

  1. We’re launching a sales coaching playbook in April, and we’re certifiably jazzed about it! The quotes and insights from this post are just a sneak preview of what you can expect to see in the playbook. Get excited.
  2. If you’re reading this and thinking to yourself, “Man, I’d love some new coaching ideas,” or “I could go for a new sales coaching framework right about now,” then we’d love to make sure you’re one of the first people to get the playbook. Shoot me an email at olivia@lessonly.com, and I’ll put you on the early access list for the playbook. It’ll hit your inbox before we officially launch it to the world!

Alright, let’s get back to our regularly scheduled programming. This blog post shares 6 hacks, tips, and tricks for training and enabling your remote sales team. We leaned on 6 of our favorite sales coaches for their expertise, so kick back, relax, and get ready to learn how to be an exceptional coach in this season of remote work!

1. Don’t be afraid to pivot.

This seems like a massive understatement given what’s happened in our world over the past couple weeks, but adaptability is truly vital. Work and life are constantly changing for sales leaders, and the best enablement leaders realize that a change of plans doesn’t need to be derailing; It’s just an opportunity to try something new, and suddenly enabling a fully remote team definitely counts as something new.

“I want my learners and sellers to be comfortable with the idea of being uncomfortable because we only grow when we’re out of our comfort zones.”

Meganne Brezina | Sr. Manager, Sales Enablement | Emarsys

2. Make “clarity” your middle name.

Honestly, maybe even make it your first. Have you heard of Albert Mehrabian’s 7-38-55 Rule? His research found that 7% of communication is verbal and 93% of it is non-verbal, with 38% of communication coming from tone of voice and 55% coming from body language. Communication and clarity matter in person, but even more so in remote enablement because we rely almost exclusively on the 7%.

“As a remote team, we were looking to implement more role playing and coaching. Our sales team is 80% remote (sometimes 100%), so it was really difficult to accomplish those two things well. Luckily, we invested in Lessonly last month to help with this moving forward.”

Jon Velasco | Sales Operations & Enablement Manager | Passageways

“Always repeat what you’re hearing back to whoever you’re talking to. Get clarification and confirmation of what you learn because what you hear may not be what people are saying.”

Roderick Jefferson | CEO | Roderick Jefferson & Associates, LLC 

3. Have grace with each other.

Your team may suddenly be juggling full-time sales, parenting, and homeschooling—and it’s tough to wear three hats at the same time. The best sales coaches are hyper-understanding of the needs of others in this season.

Here at Lessonly, our CEO, Max, recently sent out a note to remind our team to care for themselves and choose grace over judgement or “powering through the pain” in this season. If you’re interested in the note or want to use it as a template, it’s all yours. 

4. Keep those feedback loops open.

You’re not in the same room as your team right now, but that doesn’t mean your reps’ personal and professional progress needs to come to a screeching halt. In fact, we’d argue that a time where fewer people are taking meetings is the perfect opportunity for reps to focus on refining their craft and improving their skills.

“I always start my coaching process by watching and observing. I see how reps interact in an environment. I ask questions. And then I provide coaching when we’re 1:1 with each other.”

Mike Simmons | Founder | Catalyst Sale

“What reps need is a constant feedback loop and, as enablement professionals, we provide the structure for that feedback.”

Meganne Brezina | Sr. Manager, Sales Enablement | Emarsys

5. Encourage your team to leverage customer stories.

Are your customers using whatever it is you’re selling to their advantage? Talk about it. Right now, people are looking for legitimate help and different kinds of business solutions. If you know of people who are using your product or service to make their lives easier, better, more productive, etc., showcase that value to your prospects. Stories sell.

“As you know, we as individuals make all of our decisions using the feeling and emotional parts of our brains, and we really only use logic to back them up. And as it turns out, logic is highly polarizing, meaning if we come to the table with a preconceived opinion and we’re faced with logic, we’ll use that logic either to reinforce our previously held position, even if that logic is meant to dissuade us from that. So, telling stories is vital in being able to pull people in and to be able to drive change.”

Todd Caponi | Author of The Transparency Sale

“The most important tool in a rep’s toolbelt is not software, but a catalog of customer success stories that they can share with other prospects, customers, and teammates. Showing someone that you understand where they are trying to go and that others have already arrived there with you is the best tool any sales professional can possess.”

Steve Bullington | Sr. Manager Solution Engineering Talent Development | Salesforce

6. Stay focused on the numbers, but don’t obsess over them.

It’s likely your quarter looks different than what you originally expected. And there’s no need to worry because your reps are feeling the exact same way. Like we said in point #1, don’t be afraid to pivot, re-adjust forecasts, and keep on making lemonade out of lemons. It’s important to maintain some sense of normalcy and urgency around deal cycles and the natural flow of work right now, so go ahead and let those forecasts and expectations change, but then reset new goals to chase.

“There are four categories of sales metrics that can help you diagnose where you really need the help. Number one is the number of opportunities you’re working on, which helps you diagnose your ability to effectively get in the door and prospect. Two is your deal sizes, which help you diagnose your value and how you’re positioning it. Three are your win rates, which have a lot to do with your positioning and whether or not you’re working the right deals. And lastly, four is cycle lengths. What are we doing to help buyers predict what their experience is going to be?”

Todd Caponi | Author of The Transparency Sale

Tone Setters Like You

In this season, leaders like you truly are the tone setters for what work will look like right now, in the middle of an uncertain and simply weird time, but also in the future. Remote sales enablement is no small feat, but neither are you. We hope these 6 tips leave you feeling more empowered and equipped to enable your remote sales team.


Ready to do Better (remote) Work together? We’re ready, too.

Want to learn more about how we’re helping remote teams align and thrive? Visit our remote work resource hub for everything from coloring books to more posts like these—or set up a conversation with one of our teammates!

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