How to Re-engage Discouraged Reps, According to HubSpot Sales Team Managers

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Dan Tyre
Dan Tyre



Personal motivation is a powerful foundation of sales success. What role does a manager play in a rep’s personal motivation, especially when you have a new or discouraged rep? Ultimately, it’s a large role.

sales manager supports discouraged sales reps

Sales has one of the highest voluntary turnover rates compared to other industries. By 2018, the average sales rep tenure was 1.5 years — half of what it was in 2010. It is easy for reps to get discouraged when they are faced with constant pressure, demands for consistent higher performance, fierce competition and accelerated timelines.

There are various economic considerations, industry changes, company challenges, division, and team dynamics and all of those factors can either motivate a rep to perform at a high level or negatively impact individual performance.

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From my experience, direct sales management is one of the most challenging roles based on the variety of distinct skills that are required. Tough parts of the job include:

  • Balancing hard and soft skills: In sales organizations, people management requires both soft skills as well as sales skills to be successful. Many professionals focus too much on one or the other, but a balance of both is necessary.
  • Keeping reps focused: A sales manager has to manage salespeople who can be highly competitive and sensitive to outside distraction.
  • Managing employee turnover: A sales manager by definition has to coordinate multiple variables so their team can hit quota, and they must do so consistently. This often involves managing different players who cycle in and out of the team. For context, imagine trying to win an NBA championship with players joining and leaving every few games.
  • Leading a team while working towards aggressive goals: A sales manager has to invest in individual relationships while serving as a coach, internal advocate, culture leader, and communicator, all while helping close deals or they run the risk of getting demoted or fired. That’s a lot to juggle at once.

Now let’s shift our attention to disengaged reps. How can you tell if a rep is discouraged or not engaged? Here are some signs to look out for:

  • They are not focused and get easily distracted.
  • They are physically present but don’t have the same level of engagement, intellectual curiosity or emotion that they typically show.
  • They don’t perform the activities at the same rate as before or the quality of the work isn’t there — this is usually indicated by a change in their sales performance numbers.
  • They tell you they are burned out, or are exhibiting signs of burnout.
  • Their interactions with other team members are strained.
  • You can tell they aren’t on their A-game. Most sales managers work closely enough with their team to observe changes in an employee’s work behavior.

Discouraged reps will almost always impact overall team performance. Most sales teams have five to 12 people, so one non-performing salesperson can impact between 8-22% of your total number. One of the skills that is important as a sales manager is re-engaging discouraged reps.

I asked some of the highest-performing sales managers at HubSpot "How do you re-engage discouraged reps to get them back on track?" Here’s what they said.

Re-Engaging Sales Reps

Learn Why They're Feeling Discouraged

When one of your reps is not at the top of your game, try to understand why. Recognize that as a manager, though you play a role in motivation it is not your sole responsibility. You can help influence it, but the rep is responsible for their behavior and performance.

I approach the situation by asking open-ended questions and providing support. I’ll start off with a general question such as "How are you doing?" and if I don’t get a solid response back, I’ll take a different approach. Depending on the situation, I may say something along the lines of "I’ve noticed things are a bit off lately. If you want to talk about it or need any support, I’m here for you."

If the rep is aware that there is an issue and is willing to open up about it, I’ll work with them to build an approachable plan to get back on track. The last thing a rep wants to do is to commit to any type of performance plan but this is different. These types of plans are low-touch and can be easily reviewed over Slack or a five-minute audio or video check-in.

I like to remind my reps that taking care of themselves is a critical element of sales and make myself available to check in as often as they need. I have called reps at 5:50 AM every business day to get them motivated for the day — though that may not be necessary for you depending on your team structure.

Setting up a support system with other reps to and having them work in co-selling situations can be another helpful tactic for giving and receiving feedback.

Manage Expectations

Mintis Hankerson, HubSpot Sales Manager for SMB NA revisits the rep's responsibilities and expectations to work through periods of discouragement. She says: 

"For me, it always comes back to the ‘why’ for a rep and managing expectations. Some team members need to be reminded why they are doing their job. At the beginning of the year, I had a rep who wanted to take on a larger role in the organization and was ready to commit, but based on a variety of circumstances outside of her control, nothing went as planned for this year and she felt deflated.

I understood why she was discouraged, as we had previously spent a lot of time talking about her ‘why’ and mapping it to meaningful goals. After several one-on-one’s to discuss the situation, she explained she wanted to modify our original plan by taking the year to build her skillset instead of focusing on upward mobility.

My response was, ‘That’s great — I am behind you 100%. If now is not the right time to take on extra things, focus on hitting your quota because that is the main part of the job. When it’s time to go for more, it will still be there.’ This was a big relief for both of us and what was necessary to get her back on track."

Sosuke Ida, Sales Direct at HubSpot Tokyo echo’s that advice, adding:

"My approach is to reconnect the rep with their core motivation by reminding them why they decided to join the HubSpot sales team, and what they are supposed to do today.

When they are in tough situations, they tend to forget their why and tend to focus on the uncontrollable factors. So my approach is to sit down together, and reconfirm why they decided to join our team before digging into the details of the issue."

Advocate for Their Success

Greg Fung, Senior Manager on the HubSpot Solutions Partner Program shared why it is important to advocate for your reps when they’re having a tough time.

"Reps need to know you believe in them and you have their back. I reinforce this with my reps by telling them ‘I believe in you’ and following up with a corresponding change in a process or action.

I’ll typically sit down with a rep and work together to try to diagnose where the problem lies, and then come to agreement on a plan moving forward. This plan usually involves an increase in how much time I can spend with them each week, such as moving from one meeting each week to two meetings, and trying to get more visibility into their deals in the beginning stages."

Greg also encourages his other employees to support discouraged reps.

"Reps who have lost their confidence gain a lot from talking to other reps, so I’ll usually encourage them to talk to their team members who are strong in areas where they have opportunities for improvement."

Focus on Small Wins and Listen to Understand

David Torres, Principle Sales Manager for HubSpot Lat Am adds these two important points:

"First, remember you can’t boil the ocean. Telling an individual to do better isn’t helpful advice. As a manager, you can provide a path to success but my secret is celebrating the small wins.

I don't necessarily care if the rep will hit their number with this one deal. I care more about our plan being executed independent of the outcome. If our plan is executed then I will celebrate that win and the accumulation of the smaller wins creates a path forward.

Second, one of my favorite pieces of advice is ‘listen first, and then you’ll be heard.’ In sales we're taught perception is reality but for whatever reason, we sometimes forget that lesson as a manager.

If you have a rep who is struggling or discouraged, rather than imposing an attitude and assuming you have all the answers, making sure you seek to understand is a great way to gain trust."

Remind Them of the Great Work They’ve Done

Finally, Oliver Baron, Senior Manager Solutions Partner Program, NA, who was recently recognized as one of the top Managers at HubSpot in 2020, offers sound advice for instilling confidence in your reps.

"I make sure they know I have their back. I build their confidence for everything and make them take credit for all of the little things that they do every day. I help my disengaged reps break down the proven track record of what makes reps successful to show them they can get onto that path.

We work together to determine what they need to do to be successful, and they put together a plan outlining how they are going to get back on track. If they take ownership you always get a better result.

No matter what, I demonstrate to them that I am all in, invested in their success, and will meet them halfway with whatever they need."

During challenging and uncertain times, keeping your sales reps encouraged and feeling good about their work is no easy feat, but with the advice outlined above it is possible. For more ways to keep your sales team motivated, check out this post.


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