How To Help Your Salespeople On The Road

This is the great paradox of working in sales: it’s one of the most sociable jobs in the world and also, occasionally, one of the loneliest.

Sales reps often demonstrate outstanding interpersonal skills when they initially meet with a client, deliver a formal pitch and close deals, for example. They also tend to be just as strong with relationship-building over the phone, email or social media.

The potential lonely parts come in between — when they’re driving to and from client sites, boarding a plane for a long-distance meeting or simply when they’re heads-down figuring out which opportunity to pursue next.

Sales managers (or business owners in smaller companies) don’t just need to make reps feel a little less lonely. They need to ensure they can be as successful as possible across all aspects of their job.

This used to be a lot more difficult in the past, when most of the tasks performed by reps and their managers involved manual processes.

Sometimes connecting over a phone call didn’t offer the ideal way to convey important information. Sometimes reps couldn’t answer their bosses’ questions or review a document until they got back to their desks. A lot of decision-making could be protracted, causing frustration not only among reps and managers but their customers, too.

While technology offers a way to ease many of those processes and decision-making moments today, anyone managing a sales team should take the time to think through their reps’ day-to-day lives and where they could best support them.

This is even truer today, when many reps aren’t travelling by plane or driving long distances but are just as “on the road” in the sense that they’re working remotely from home and trying to make the best use of their time. This is what you need to do:

1. Establish a consistent (but flexible) check-in

Sales reps need to be vigilant about their schedule, especially when they have to connect with clients who are mid-way through a purchase process. That said, a standing meeting with you (their manager) should always be somewhere on their calendar.

There are all kinds of time management apps and scheduling tools to help with this kind of thing, but the most important part may come down to a policy that you and the rep agree upon.

Start by choosing a time when you and the rep will be in the best position to move forward with as many opportunities as possible. That could be early in the week, later or in the middle. Figure this out by understanding what kind of data you’ll both need to bring to that check-in meeting. Start and end it on time, so the rep will have confidence that their check-in or touch point with you won’t be interfering with their other priorities.

Of course, things will happen that occasionally force one or both of you to reschedule the check-in. Rather than randomly choosing a new time, have a Plan B and Plan C time that would most likely be available on a week-to-week basis. That way you won’t go half a month or more without a virtual meeting.

2. Direct them to the most actionable data

You’ve probably made the case for using a CRM by explaining to your reps the power of collectively sharing data about customers. There’s no better way to reinforce that message by helping them make sense of the data to increase their win rate while they’re on the road.

The dialogue between a rep and their manager works best when both of you are ready to sit down with the insights you’ve drawn from a CRM. It could be details about a particular account where you’re trying to close a deal, or more overarching trends and patterns you could use to improve their performance as a whole.

A good CRM will make this easier by surfacing actionable ideas based on analytics it performs automatically. If your CRM has artificial intelligence capabilities, even better: you’ll be able to spend more time coaching based on what you know about the future, rather than rehashing what happened in the past.

3. Clarify communication preferences

You’ll still need to connect with sales reps outside of a weekly check-in or touch point, of course. Questions or urgent issues around a customer are bound to come up at other times of the week. Reps can get frustrated, however, when they’re forced to respond in ways that don’t feel natural or enjoyable.

Talk about this with reps early on — long before you put them on the road or have them work from home. Some of them may like to hear another voice and will be responsive to a phone call. Others will be glued to their email. Depending on how in-depth you need to get on an issue, a text message or internal social messaging app might be the best tool for the job.

Agree on this area and you’ll avoid wondering why reps aren’t responding right away. You’ll also be more available when they’re the ones reaching out to you.

4. Humanize work however you can

When you’re not getting a lot of face-time with a rep, it’s easy to focus only on their results and the minutiae of business. If they were sitting in a nearby cubicle, however, you’d probably treat them differently.

You’d likely walk by on a Monday and ask them about their weekend, for example. You might reference a recent hockey game, a hot topic playing out in the media or a blockbuster movie that’s opening soon. Even the most competitive reps will do this with each other; you should too.

Reps might be your direct reports, but they’re also your peers, because they’re other human beings. Make sure your outreach isn’t limited to client stuff.

Organize virtual meetups with the team via videoconference. Ask an intriguing question of the week on your intranet to learn more about everyone’s personalities. And of course, find ways to virtually celebrate wins, even if it’s a GIF showing a bell ringing when a deal gets closed.

Whether they’re on the road or working from home, chances are reps will eventually have a reason to come back to the office. Make sure that when they return, they feel welcomed, supported and appreciated as the essential team members they are.