Employee Engagement

How To Develop and Keep Business Relationships As An Outside Sales Rep


Do you ever get the feeling that we’re too connected? 

When’s the last time that you went to a party, met up with friends at a BBQ, or had a family reunion, and found that someone started talking to you about something you posted online? Oh, hey, how was that ski trip? Wait, how did you… Oh yeah, I had those pictures on my Instagram. 

Don’t worry, we’ve all been there.  But this feeling of hyper-connectivity has two major downsides: for one, it gives us the impression that we’re connected to way more people than we really are—which studies have shown can even lead to depression, as we’re seeing all of these “great” lives that we’re not living. 

But even more than that, it can affect the relationships that we do hold dearly in our lives. Because instead of actually taking the time to connect, we let the passivity of social media do the “connecting” for us. 

This gets even harder when relationships are a part of our business. For virtually every outside sales rep, relationships are the lifeblood of a successful career—the and the better you are, the harder it gets to maintain those relationships. 

Here are Hoopla, we’re all about connecting people, and our goals has always been go increase employee engagement. Engagement is a problem that we’ve seen our clients struggle with more and more over the years, as it seems there are more and more ways to get distracted and tugged in different directions. 

So if you’re an outside sales rep who’s having a hard time feeling connected not only to your clients, but also to your organization—or you’re a manager who’s struggle to keep her employees connected—we’ve got just what the doctor ordered.  Check out our tips below, curated from years or getting to know sales reps who struggle themselves, and pick one or two to try for yourself this week!

“Calendarize Everything”

How many times have you told yourself, “Oh, yeah, I’ll respond to that message later,” only for it to be banished to old-message hell for all eternity? 

Here’s a simple, ten-second task that’s going to save you not only time, but also save you from worry, missed-opportunities, and even lead to a more productive day: put everything in your calendar. 

Missed a call from your spouse and don’t have time to talk now? Pencil it in for lunchtime. Saw an email from an old prospect that looks promising, but you’re about to walk into another meeting? “1:30p – Respond To Prospect”. Don’t forget that several email clients like gmail have a new ‘snooze’ button, that will allow you to reschedule that email from an old prospect. Just click the snooze button and set it to pop right back up when you’ve got the time blocked off in your calendar. It’s like getting the email at the perfect time. 

Suddenly, you’re no longer playing catchup, or having to remember and track down every little part of your day—you’re letting your calendar be the personal assistant of your dreams. And all it takes is that few-second force of habit to form, and soon it’ll feel as easy as pushing a button. 

Using Tech For Good

Okay, so we just spent the first few paragraphs of this post talking about the ills of technology—namely, social media. But let’s brush that negativity aside for a second and reclaim tech for good. 

The trick is simple: make tech work for you, not the other way around.  As Hubspot’s Tim Jernigan so aptly puts it, “Adapting technology for your sales process is like giving your entire team superpowers. The right solution helps your reps finish busy work more quickly, so they can focus on meeting customers and closing more deals.” 

We’ve often talked on here on the blog about how we’re entering a golden age of remote work. It’s easier now than it’s ever been to work out of the office. But if you’re not careful, it can also become super easy to feel disconnected from your employees—and while that not might feel so important to you now, studies show that it often leads to lowered engagement, and a loss of sense of purpose in your work. 

One example of tech that works to keep yourself engaged with remote employees, and can also work for your clients on the road, is the concept of “regular check-ins.” Pretty high-tech, isn’t it? 

The concept is simple, mark down a weekly goal of checking in with both clients and your team a certain number of times per week. That can feel tough when every check in is a phone call or email—but you can also set up Slack chats for various customers or team members, do group-hang video conferencing, or even establish a sales leaderboard that keeps everybody up-to-date on each other’s numbers. 

The good news about tech is that it allows us to be creative about the ways that we keep up with each other. Don’t feel limited by the possibilities in front of you. Find something that really works for you And for all the managers out there who may be a little worried about investing so heavily in a new way of doing things, Jernigan also reminds us: “Increased productivity leads to lower costs.” So at the end of the day, a little upfront investment can lead to huge returns. 

Ask For Help

We’ll leave you with one final point. Just because you’re an individual contributor, that doesn’t mean you’re on an island. Everybody has challenges that they face in their job, and the person who’s going to understand your situation better than most is your manager. They’re whole job is to empower you to be at your best—and managers, that’s a reminder for you, too!

Put on your calendar for today a few minutes to write an email or make a phone call to your manager (or your employees!) to check in. Be honest with how you might be feeling disconnected, or simply ask for advice on how to stay better connected to your clients. 

Undoubtedly, this will do two things: not only will you find some great advice on the other side of that email, but you’ll also open up a whole new channel of communication with someone who understands, cares, and can offer support that goes way beyond your current predicaments.  We’re all in this together, so don’t waste the opportunity to benefit from all the valuable resources your company and your team can offer! Good luck!