Five “Course Corrections” for Sustained Sales Management Impact

By Shannon Holmes, President, DoubleDigit Sales
Two people standing in front of a white board with post-it notes and drawings on the board.

It wasn’t long ago that the world (or at least us space enthusiasts) held our breath while NASA made a critical course correction that would either make the Mars mission a success, or have the rover miss the red planet completely. Luckily, they nailed it.

Back here on Earth, we sales leaders have “course corrections” of our own to do as a result of the pandemic. Now two years in, our people are fatigued and there are other pressures at play too, like the war on talent and ever-changing buyer behaviors. Here are five bite-sized ideas for engaging and supporting your remote sales team right now. They’re practical and should garner immediate results.

1. Teach through prompting

When one of our salespeople has a challenge with a buyer, our knee-jerk reaction as their manager is to offer a solution. That’s the benefit of our experience – we’ve seen it before and can help. But instead of doing this, apply the “give a person a fish, teach a person to fish” analogy and use questions to help that person devise their own solution. Now you’ve helped them develop a plan of action and you’ve taught them how to work through a problem on their own.

How to do it:
Ask your salesperson questions that help them analyze the situation. Approach it methodically to break it down and work through the challenges.

Best practice:
Start questions with trigger verbs like “compare,” “describe,” “explain,” “outline,” and “share.”

2. Turn feedback into a conversation

Giving feedback is often dwindled down to pointing out errors. But as managers, we can be far more impactful by providing both positive and constructive feedback, and more so, by making “feedback” a conversation.

How to do it:
When coaching, always start with the positive aspects. Ask questions that help your salesperson reflect on the situation and where they were strong. Make sure to share what you observed as well. This builds trust and confidence and avoids making your team member feel embarrassed or vulnerable. It also makes them more receptive to any constructive points you want to discuss. After this, have them identify what they could do better/differently next time and share your thoughts. Keep the focus on building skills.

Best practice:
Always engage your salesperson first (before sharing your thoughts and views). This makes them a part of the conversation vs. you delivering one-way feedback.

3. Use one-on-ones to look at the whole-picture

Most one-on-ones with our salespeople center on opportunities and closing business. This is important, but we’re missing an opportunity when we don’t step back and look at the big picture. When we get busy with day-to-day tasks, it’s easy to lose sight of the person and get laser focused on the tactical aspects. By regularly revisiting the whole picture, as part of your one-on-ones, you’ll help your team member grow and teach them the invaluable skill of effortlessly switching between micro and macro thinking.

How to do it:
In each one-on-one meeting, start by looking at the bigger picture. Look for trends you’ve noticed over the past month and engage your salesperson in a 1-to-10 scale-based question. Before identifying items for an action plan, use your questioning skills to drill down and understand what’s below the number. After a strong strategic conversation, shift the focus to talk about the tactics.

Best practice:
As part of the strategic portion of the conversation, make time to celebrate their wins and growth.

4. Deepen team engagement in meetings

Sometimes, standing meetings can feel monotonous. It’s our job as leaders to create value in them. Admittedly, it’s trickier to do this with virtual team meetings, but, with a little creativity and planning, it’s doable – and well worth the effort. Think: What can you add to your agenda to excite and energize the team, increase sharing, and create more camaraderie?

How to do it:
Try weaving at least one of these into your agenda. You might also rotate through some of these to add variety:

  • Ask team members to lead portions of the meeting.
  • Start the meeting with a fun energizer.
  • Balance the time allotted for team updates and individual sharing.
  • Recognize outstanding performance.
  • Run (or have one of your team members lead) a skill-building activity.

Best practice:
Ask your team for feedback to understand what’s working best for them and what would add more value.

5. Foster team connection

Gone are the days of lunchroom chats with colleagues. While we await their return, we need to create new avenues for connecting with one another – because tight teams make the work environment better and people happier. Encourage your sales team to connect frequently, and not only for business purposes.

How to do it:
Here are some ideas for creating “water-cooler” moments for your virtual team:

  • Encourage a Friday “walking meeting” where two people get outside for a walk and talk.
  • Organize a monthly virtual cocktail. Up the ante by delivering cocktail kits.
  • Run a one-off virtual social to play a team quiz or game (, Drawasaurus, and Kahoot! are good ones).
  • Set up a team challenge to encourage getting away from their desks (like signing up for an app where you can hike a famous trail).
  • If your team is in the same region, have them meet up for a fun outdoor activity like visiting the driving range or playing a round of mini-putt.

Best practice:
Putting a little budget aside for this will allow you to pay for activities and buy/mail prizes.

Value-add change is great, but give yourself time to make it happen. You can start by incorporating one of these practices each month. If you stay consistent, by summertime, you and your team will be a giant leap ahead. It’s not rocket science, but it will create engagement and add value to your sales team during this time.

Today’s post is by Shannon Holmes, president at DoubleDigit Sales, a Top 20 Sales Training Company as recognized by Selling Power. Connect with DoubleDigit Sales on Twitter and LinkedIn.