Managing a Remote Salesforce: Things to Consider

By Steven K. Haught, MBA

Has your company started preparing the foundation that will allow their sales teams to work remotely?

The pandemic has raised the question once again as to the viability of sales teams working from their home offices. During the past two months, lots of chatter around the topic has raised concerns about whether companies are really thinking through the issues of a remotely based revenue producing organization.  

Are you and your sales team prepared for the inevitable “virtualization” of the sales process in your company?  This is a major decision, and needs to thought through carefully, or you will be sadly disappointed.

Your business needs to be prepared for the incoming “new normal” and that means, your organization and your sales team needs to start looking at specific standards for performance and in-the-field selling.  Quite possibly, at least for the near term, selling from start to close without ever meeting a prospect or client face-to-face.

Let me start off by saying that I have managed remote sales teams since the late 90s, and as an organization we were very successful.  Our revenue streams were consistent and the sales reps were accountable and professional.  So I know a lot about what I am about to suggest you consider as you prepare for remote selling.

Managing remote salespeople isn’t without its challenges. But done well, managing remote salespeople is incredibly empowering, for the sales leader and the sales team.

The key to success is having the right systems and processes in place. But there’s another piece you’ll need that transcends beyond any process or tools—and that’s trust.

Let’s explore why trust is everything when it comes to managing remote salespeople, and figure out how you can master this area of sales management.

Managing Remote Salespeople with Trust

I’d like to stress this first important point, before any other factors. 

If you’re controlling, if you’re a micromanager, if you have trust issues—managing remote salespeople is going to be VERY difficult for you unless you’re willing to change your mindset.

Believe it or not, not everyone is out to take advantage of you or a situation. Not everyone is trying to pull one over on you. BUT, those types of people DO exist, and many of them inhabit sales organizations. Under a watchful eye, with in-person accountability, they care be some of your top producers.  Controlling, micromanaging sales managers can work with such sales reps in an office setting, and you can remotely.

That’s why—rather than acting like a crazy person AND stressing yourself out—you should focus your energy on putting systems and processes in place that will hold your team accountable. More about the tools to measure performance and accountability later.

But for now, let’s focus on the importance of trust.  It’s important to establish a high level of trust with any person that you hire. For remote salespeople, it starts with having the right hiring and on-boarding processes. Trust starts right from the beginning. And it’s all about tuning into your intuition about people.

But what exactly is trust? The first definition of trust on Merriam-Webster.com is “assured reliance on the character, ability, strength, or truth of someone or something.”

Trust means relying on another person to do the right thing, and do it all the time. You believe that they are a person of integrity, and you are willing to stick your neck out for them because of this.

As a CEO or Sales Manager, trusting your employees is the only way you can function in your responsibilities without going crazy. 

The danger in not learning to trust others in a revenue driven organization, is creating an atmosphere of mistrust that can destroy your company.  Most likely you as a leader, who cannot adapt and trust others, will be terminated.

So… if you don’t trust them, don’t hire them. Listen to your experienced inner-self, your gut, your intuition. Or, if they’re already on your team, get to the bottom of the issue of why you don’t trust the person. Then, decide whether this person should stay on the team or if it’s time to cut ties.

Trust and respect go hand-in-hand, so it’s important to begin with trust. Many people like to say that “trust is earned” and they vet people for years on end. This is not an effective way to manage and can actually cause more harm than good.

So let’s review and I’ll add a few additional key points to the issue of trust, because nothing breakdown an organization quite like the lack of trust.  Hire people you trust; trust the people you hire.  In 2013, a Harvard Business Review report demonstrated that people avoid helping others when they lack trust in their teammates or managers. If you don't think your actions will be rewarded or reciprocated, why make the effort at all?

This problem can be exacerbated in sales teams, which often structure goals around individual accomplishments. And when you have a remote sales team, it takes extra effort to build trusting relationships. Communication is key to building trust. You've heard that before, but it becomes more important with remote teams.

Sales managers should plan their working schedule to overlap a majority of their team members. That way, if any issues or questions arise, you can respond immediately.

When you pay attention to your team's needs — even when they can't physically tap you on the shoulder — you build trust. 

However, you also must avoid micromanagement.  While this can be a challenge in a typical office setting, the negative effects of micromanagement also expand to remote teams. As a manager, your communication isn’t always immediate, and you cannot interpret your team members’ body language or learn their mannerisms. Micromanagement itself can become self-defeating for remote sales teams.

Build trust.  And remember, trust goes both ways—you to them, and your team to you. Most issues will be cleared up quickly if you remember to communicate frequently with the united team and each rep individually.

What if you just can’t seem to trust certain individuals on the team?  Or, maybe you suspect the team is conspiring to get you fired?   Mistrust in your employees can be very damaging, especially to employees that don’t deserve it. If you’re constantly questioning what your employees are doing, you’re opening the door for trouble.

Before you lash out at an employee or question their activity, ask yourself, “What am I trying to accomplish?”

If you feel like they’re underperforming, address it in an appropriate way. Set up a meeting or use your quarterly (QBR) one-on-one meetings to address issues with individuals. 

Remember, you’re not your employees’ parent! It’s not your responsibility to track every second of your employees’ time. All this does is take you away from your own responsibilities. So give a little grace here. Trust your employees.

As long as your team is closing deals, give your team the opportunity to work freely.  Plus, research shows that employees who have autonomy over their schedules work harder and longer hours.

Ways to Establish Trust

Lead by Example.  Expecting perfection from someone else while not practicing what you preach is a recipe for disaster.

Leading by example means doing the right thing even when no one is looking. Are your activities and behavior aligned with the organization and your goals?  Do you do what you say you’re going to do? Do you mean what you say? Is acting from and with integrity something you pride yourself on? Do you keep your promises?

On the flip-side, do you say one thing and do another? Are you unwilling to do the things you demand and expect of others? Do you often have unrealistic expectations?

Being a leader means leading by example. It means being the first one to do the right thing.  You’re on point… you are first on the field of battle and the last off.

If you want to build trust with the people on your sales team, lead from the front. Focus on your own behaviors and actions first. Your team will see and will emulate the great leader they are following!

Communicate Openly.  Having open and honest communication with your sales team is vital to trust. Communication is the gateway to knowledge. So keep frequent and open communication in mind, always.

As you manage your remote sales team, you’ll want to make sure you have processes in place to make communicating easy.  Video conferencing is the way to go to achieve faces and smiles and coffee cups in full view!

A weekly sales meeting is a must, again use video conferencing technologies to get a level of visual intimacy. It’s an opportunity for everyone to sync up, talk about their issues, discuss the pending large value deals and keep momentum rolling.

Between meetings, ensure that you have processes in place to make the team feel connected. You might consider having coaching calls with your team members or assigning smaller teams with one team member as the coach or team lead.

There are so many ways to communicate today. The key here is making sure you don’t drop the ball. Stay connected to your team and encourage your team to stay connected to each other for support.

Be Open to Feedback.  Trust goes both ways. As you lead by example and create streams of communication with your team, don’t forget to ask for feedback.

Being open to feedback will make you better as a leader.  The very best leaders exhibit honest vulnerability and accept criticism, justified or not, without retaliation.

Think about it this way: you can keep doing the same old thing and wonder why it’s not working. Or, you can encourage your sales team to share feedback with you (about anything) and get to the bottom of an issue. Which will get you to your goals? I’m confident the feedback route will get you there. Burying your head in the sand or creating an aura of being an unapproachable intimidating leader are not effectives way to lead or manage.

Lastly, As a remote sales manager, asking for frequent feedback is to your benefit. It’s better to get ahead of a potential issue as opposed to dealing with a problem after the fact. Encourage individuals on your sales team to come to you directly for feedback related to you, senior management, or company concerns.

For other feedback about things like sales methods and processes that involve the team, you might consider adding a section in the forums area of your Sales PlayBook called “Feedback,” and using it as a place for the team to share feedback. But be cautious. You don’t want this to become the “complaint committee” forum. Be clear about your intentions with the team. Let them know that the “Feedback” forum is for problem-solving issues that involve the team. (If you don’t have a Sales PlayBook, you should develop one)

Encourage Collaboration. Encouraging collaboration will help build trust between you and your team members and between the individuals on your team.

Share successful closed deals to get your team engaged in collaborating.  Share the things done in successes, pass on good ideas, etc., to keep the team collaborating. During the weekly sales meeting, ask each salesperson to share their best success story to keep the enthusiasm up and everyone on the team engaged.

You might also consider creating units within your team. This helps immensely with collaboration and will help you avoid the “island” mentality that can develop with remote sales teams. You can assign tasks, unit sales goals and projects related to team communication, such as a presentation to pitch certain types of clients/buyers.  Assign one of the three reps as the unit coach.  Make it a rotating function that way no one has to volunteer! The responsibility of the coach is to keep the unit on task and goal target. The coach ensures that phone calls happen and that initiatives are addressed.

If members of your sales team are meeting via phone or video chat on a weekly basis to help each other, they’ll drive each other. And you’ll watch the power of collaboration produce revenue!

Get to Know Each Other.  Nothing builds trust better than actually knowing a person. But you can’t get to know a person if you don’t spend time together.

Collaboration isn’t the same as getting to know someone personally. And getting to know someone on a personal level when they’re working remotely can be challenging. But it’s not impossible.

Consider adding a section in your Sales PlayBook about the sales reps family and personal interests. Information that is personal in nature—like outdoor activities, sports, cooking, recipes, etc., can be a great way to connect a deeper level with your sales team.

Add a section, (optional participation of course), that allows each sales rep to talk about their personal passion.  Lots of “golf scores” and handicaps will get reported!   This gives team members an opportunity to share something near and dear, which helps others build a bond.

If the budget allows for an annual in-person retreat for the sales team, do it. Having the retreat open to your team member’s spouses/partners can also be hugely beneficial. This way, team members are more than just fellow salespeople: they’re friends and family.

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