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Leading Sales Teams During Challenging Times

As we start another week and approaching a new month, Sales Leaders in B2B have challenges today that are making it even more challenging to achieve growth quotas. Therefore, let's explore some best practices to help you and your sales professionals achieve in these trying times.

Celebrate Small Wins

As we’re adjusting to a new normal, your standard of what’s worth shouting about is bound to change. So while you might have patted yourself on the back for beating YOY sales, now, you might feel the same level of pride by converting just one lead into a sale.

Being in a remote team is about being able to find an internal motivation that comes from the recognition of small wins, rather than a larger, looming pressure. When managing a remote team, encourage reps to give themselves shout-outs, and celebrate together no matter how big or small a win may be.

Clear and Relevant Communication

Switching from verbal conversation to text-based communication can be tricky. The solution is to keep your speech as simple as possible.

Vet emails to make sure they’re sharp, short, and to the point. If you asked a question, did you use a question mark? Did you exaggerate or play something down? You’ll need to become a much more straight-down-the-middle type of communicator to make sure your remote communications don’t get clouded.

Leaders, you may need to provide some training on what good communication looks like. It could be as simple as a Zoom meeting, where you show your reps an email or InMail that works vs. one that doesn’t, and why.

Adopting & Integrating Technology

How many times have you been told to download Slack or Zoom? Probably one too many.

The truth is, it doesn’t really make a difference which instant messaging system you download; it’s how you use it that matters. Technology is supposed to replicate everyday activities, so you have all of the same benefits out of office that you’d have if you were working side by side.

Ten-minute motivational talks. Target-focused meetings. Private conversations to talk about tough prospects. These are all reasons why you should make an effort to chat with coworkers in Slack — or any other system — as you would in the office.

Make it a point to ask quick questions, be interested in individuals, and stay connected.

Your Preparation to Achieve

Successful remote sales professionals don’t just have their head in the game, they have the game plan and plays planned.

To build momentum throughout the day, you’ll want to write down and isolate your daily activities. Whether that’s talking with the team, reviewing your prospect list, or brainstorming new ideas to add to your pipeline, you should have a dedicated slot for it.

This approach helps you create a sense of structure to your day that will allow you to work in a productive break between each activity.

Managers, if you see your team’s performance slipping, ask them how they structure their days and schedule. Consider doing an activity & calendar review as part of your daily or weekly coaching.

Fuel & Energy

Working remotely is a lifestyle change that can cause people to become sedentary for most of the day if they’re not careful.

Being inactive isn’t good for you, and it’s also no good for your sales role. People can spot a flat sales pitch within minutes by listening to your tone, pitch and pace. While pushing through a bunch of follow-ups is impressive, it’s better to take a quick timeout every hour to walk around the room, lift your gaze, do some stretches, and adjust your working position. Your body and sales record will thank you for it.

When managing your team, be aware that reps may not feel the same freedom to get up from their computer when they’re working remote. They may struggle with finding balance, since their home life and work life are blended. Talking these issues out can help them know you “see” the work they’re doing.


Just as we celebrate small successes, we set small goals. Or rather, we get to celebrate small successes as a result of small goal-setting. In remote sales, there’s no public leaderboard to keep you accountable or a sales manager breathing down your neck.

The get-up-and-go attitude will need to be generated by your drive to succeed rather than a fear of failure (and looking stupid in front of your coworkers).

In this spirit, small goals shouldn’t be scary; they should be stretchy — just enough to challenge you, but not enough to break you.

Time Management & Scheduling

Using time blocking now and then isn’t as effective as using it every day.

Our star sales members create rigid schedules with plenty of repetition in their routine. This helps them to psychologically block tasks and get into the right mind frame for the task ahead.

Your schedule will depend on your preferences. For example, if you work best in the early afternoon after some fuel, set important “brain consuming” tasks (like creating proposals) after lunch, when you’ll be at your most efficient. Set more menial tasks (like quick follow-up emails) for periods where you won’t find it so easy to get into the flow of things.

Action = Achievements

Our behavior is much more advanced than that of a dog, yet training ourselves to do the right thing isn’t all that different from training a dog to respond to a command. Classical conditioning — pairing an action or sound with an event — works on humans as well as dogs.

It will be much easier to develop positive habits and continue to tick off tasks by implementing classical conditioning. You can do this in the form of a virtual tick list or a well-deserved five-minute break each time you complete a piece of work.

Whatever it is, make sure you do it in sync with the achievement to begin to create a mental association. Over time, you’ll learn that finishing a task feels good and allows you to confirm your achievements in some form of visual or physical manner.

Managers, consider creating a “Ring the Bell” Slack channel where team members can upload a meme when they make a sale or hit a goal.

Creating New Lead Channels & Practices

If you continue to rely on networking to bring worthwhile prospects your way (especially at a time where you can’t network in-person), you’ll start to see your sales funnel dry out. It’s important to develop other ways of attracting interest, so you can find leads from all over the world.

Make sure you train your team in the best ways to interact with prospects in a crisis situation. This could make or break their ability to hit their numbers.

Create the Green Go Trigger

The hardest part of the week is the same for a remote worker as it is for any office worker — Monday morning. To be as effective as possible, you need to make sure you’re mentally in the game as soon as the workday starts.

That means you’ll need to create your own “on” switch that isn’t your boss’s briefing, your colleagues quizzing you about the weekend, or the constant pressure to make it to the office on time.

Listening to audio clips of coworkers and simulating the office environment is the best and easiest way to shake off that Sunday feeling.

Recognition of the Team & Accomplishments

Recognizing our small wins is one thing. Recognizing others’ is perhaps even more important.

Remote sales managers should make sharing sessions a key part of their weekly agenda and actively seek good work to shout about. This strategy helps your sales team coach each other on the best selling techniques — and create a sense of belonging within your team.

If you aren’t a senior in sales, you don’t have to shy away from this tip. Sending a quick Slack message to congratulate someone on closing a deal or nominating your coworkers in private is a great way to strengthen your remote relationships.


Leaderboards, high-fives, and boardroom meetings may now be a distant memory for you and your team. Without a sense of in-person support and healthy competition, how will you fair? Fortunately, it’s not as hard as it may seem.

To survive in remote sales, you’ll need to:

  • Become self-sufficient by figuring out how to find internal motivation.

  • Get more organized and use time to your advantage.

  • Be kinder to yourself and celebrate the small things.

  • Make small talk even when you don’t have an opportune moment.

  • Find out your reason why, so you can visualize and materialize it.

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