How to Run Sales Meetings That Unite and Upskill Your Team

November 19, 2020

“No one wants to sit in a meeting where you are being talked at for 30 minutes, especially via video,” Colin Callahan, the director of sales at Reonomy, said.

He’s not wrong. After months of grappling with Zoom fatigue and stuffed schedules, even a once enjoyable weekly team meeting can quickly become a dreaded chore for sales teams. For leaders hoping to see fewer glazed expressions while they run their meetings, Callahan said there are some things meeting leaders can do to inject extra productivity and fun into their syncs.

“Encouraging the team to problem-solve their own blockers by bouncing ideas off one another creates autonomy in the role, leads to higher engagement and morale, and instills confidence in individuals as they continue to develop their skills,” Callahan said.

Other sales leaders agree. By allowing their teams to share their best practices, wins of the week and bond with their peers, meetings don’t have to feel dry. In fact, they can be used as a valuable tool to boost job satisfaction and ensure each rep’s week runs a little smoother. 

To learn more about how to pull off a productive sales meeting, Built In NYC talked to sales leaders around the city about their best tips for running engaging meetings. 

 

Alvin Artha
Director of Advisor Revenue

What they do: SmartAsset wants people to make better decisions around retirement, mortgages, student loans and more. The company’s tech, which helps put financial tools into the hands of 65 million people monthly, includes calculators, content and a service that matches users up with local financial advisors. 

 

How often do you hold sales meetings with your team and what are the key objectives of those meetings?

We have a specific method for how and when we schedule meetings for the SmartAsset direct sales team. We generally have a kick-off meeting in the first week of the month to review the last month’s performance, recognize our top performers, compare results to KPI goals and celebrate big wins for the firm. We then present the strategy for the current month and outline our training program, which entails about three internal training courses and how improvements in these areas will impact the bottom line. 

The first two weeks of any month are crucial for a fast start for any sales team, which is why we schedule our training sessions at the beginning of the month. We schedule one 30-minute training session per day after lunch when we know our reps are fully locked into the day and ready to absorb information. We then do reinforcement training with smaller groups to ensure that we have everyone’s attention and active participation.

For the remainder of the month, we reinforce these training topics once per week on Wednesdays after lunch. We specifically chose Wednesday because it’s the halfway point in the week, which allows us to course-correct if we’re falling behind our success metrics or to keep pushing forward if we’ve surpassed our weekly goals.
 

In this remote working environment, we understand that salespeople need more camaraderie and socialization to thrive.”


In this remote working environment, we understand that salespeople need more camaraderie and socialization to thrive. Twice a week, on Tuesdays and Thursdays, we end the day with a social virtual huddle that we’ve coined “EOD ALL AE CHAY” (“chat” turned into “chay” so it can rhyme). This way the reps can catch up, talk about their day and unwind. 

 

What specific actions do you take before or during those meetings to ensure they're productive and engaging?

Before a meeting, I always share my presentation to a few of my top performers on the sales team to ensure that the content is sharp, accurate and set up to resonate. I also encourage our top performers to participate in the meeting to share success stories, sales tactics and examples, since the rest of the sales team looks up to them. I rely on their participation to build momentum throughout the meeting and get more engagement from the rest of the team. 

When I present to the sales team, I don’t overload the deck with words. Rather, I summarize my talking points and ask pointed questions to increase engagement among my peers and direct reports. Asking questions and waiting for responses is crucial to getting buy-in, because questions demand responses. 

 

What role do your salespeople play in shaping the conversations and decisions that take place in those meetings?

The trainings that are the most productive and helpful are typically held by our top performers. I don’t shy away from utilizing these key players because they are the ones in the thick of it. They are the ones who are constantly taking phone calls and exceeding sales goals. We make a collaborative sales effort to let our top performers shine and share valuable insight, tips and tricks in these training sessions. 

Meetings are also a place where I can uncover any shortcomings. At SmartAsset, sales reps participate avidly in meetings, so we’re able to see that if one person is unclear about something, there may be others. I do my best to create an atmosphere that nourishes a strong feedback loop between reps and leadership so that reps can feel comfortable opening up in these meetings.

 

Danny Hodge
Head of Sales

What they do: Wix’s user-friendly platform makes it simple for anyone to build and launch a website. So far, the company has helped 182 million users create personal or professional sites. 

 

How often do you hold sales meetings with your team? What are the key objectives of those meetings?

Since we’ve been in quarantine, we’re meeting every morning to start the day. We’ve branded the meeting as our “daily sales education” and cover topics from industry trends to sales psychology to new Wix product reviews. The objective on leadership’s side started simply as an accountability check, but it has really evolved. 

A huge dynamic every team is missing while working from home is an informal channel to disseminate information, which used to take place with conversations between teammates walking to get coffee or pick up lunch, or a casual exchange of sales tactics and ideas over a drink at the end of the day. Those things are gone, but the value of information-sharing is not. The objective of our daily meetings has really been recreating a culture around information-sharing that allows everyone to make their teammates better.
 

The salespeople are the drivers of our daily meeting.”


What specific actions do you take before or during those meetings to ensure they're productive and engaging?

One of our sales managers is responsible for the programming of these meetings. Each day has a different theme and within that, we either assign a member of our team to present something or ask a member from a different part of our organization to join. 

For instance, every Tuesday, an account manager joins us and shares a win about one of the clients we passed over to them. On Fridays, we are joined by a product marketing manager to review the roadmap and new features our product team is releasing.

 

What role do your salespeople play in shaping the conversations and decisions that take place in these meetings?

In many ways, the salespeople are the drivers of our daily meeting. When a salesperson is assigned a day to present something and is given a theme to help with inspiration, they are free to run in any direction they find relevant. It's often illuminating for leadership to see what topics the reps select as relevant: it's unfiltered feedback on where the team might be struggling or might see new opportunities that we should be acting on. 

A sales manager can only listen to so many call recordings and join so many demos. When we have salespeople taking the time to decide what they want to share with their teammates, it allows us to keep an accurate pulse on what's going on across the floor. 

Once or twice a month, we ask the team to run a meeting without leadership on the line to have a “players-only meeting” where they can discuss anything they would like to bring to our attention. In general, the involvement of the salespeople gives them real ownership of how the sales organization is run.

 

Matt Elders
SVP, New Business North America

What they do: ContentSquare is a SaaS company helping brands increase engagement across digital channels through its user analytics platform. 

 

How often do you hold sales meetings with your team? What are the key objectives of those meetings?

There are a few types of meetings I hold with my team.

During weekly team meetings, the objective is focused on communication to ensure everyone on the team continuously feels connected to our mission, which increases motivation to achieve more. One large aspect of this meeting is to educate everyone on how the team and business is performing and share best practices. Also, recognitions are given to team members to encourage and celebrate each other.
 

I constantly encourage my team to think outside the box.”


Monthly team meetings with departments outside of sales are where we bring our collaborative culture into the mix by inviting every function with a direct impact to the sales team for a monthly meeting that focuses on key business updates, accomplishments and challenges. The purpose here is to break down silos between departments and focus on being one team that aims for the same goal. 

 

What specific actions do you take before or during these meetings to ensure they're productive and engaging?

The objectives mentioned in the previous question help the meetings stay on track. In addition to those, I introduce more philosophical ideas on how we can potentially do better as a team by addressing themes we are seeing in the organization. 

I constantly encourage my team to think outside the box. I refer to a book called “Mindset: The New Psychology of Success” by Carol Dweck, where she speaks to the criticality of having a growth mindset versus a fixed mindset. I want my team to focus on a growth mindset for us to strive for the best. 

 

What role do your salespeople play in shaping the conversations and decisions that take place in those meetings?

My team is very involved in shaping the content and conversations during these meetings. I depend on my team leaders to guide some topics, as they are closest to what is happening in the field. Those include topics like wins, challenges, approaches and more. 

 

Colin Callahan
Director of Sales

What they do: Reonomy aims to provide the commercial real estate industry with better insights on properties, which can lead to more opportunities for individuals and companies alike. Using data, machine learning and industry partnerships, Reonomy is looking to enhance property intelligence. 

 

How often do you hold sales meetings with your team? What are the key objectives of those meetings?

Given the current work-from-home environment, the entire sales organization at Reonomy meets on a weekly cadence. In addition, we meet twice per week with each regional account executive team and once per week with the sales development representatives team. The overall objectives of these meetings are to provide internal updates, understand roadblocks the team is facing and establish an open dialogue where our team members can discuss best practices and ask questions. 

We try our best to keep things fun over video calls, especially as we continue to hire new members of the team. Our favorite way to start a meeting is by asking ice-breaker questions like, “If you could meet any historical figure, who would it be and why?” This keeps things interesting, the conversation is light and we learn more about one another. Additionally, we love to highlight a “win of the week” in our meetings, so everyone feels recognized for their hard work and accomplishments.

 

What specific actions do you take before or during those meetings to ensure they're productive and engaging?

Prior to the weekly meetings, we choose a different theme of focus, based on current challenges the team is facing, which ensures that the conversations are relevant and actionable. We send the chosen theme to the group in advance so they’re prepared for a thoughtful discussion. My goal during the meeting is to act as a guide to ensure the group stays focused by asking open-ended questions, allowing the team to brainstorm and create their own solutions. 
 

Encouraging the team to problem-solve their own blockers by bouncing ideas off one another creates autonomy in the role.”


As our team continues to grow, especially with multiple open roles for our SDR team, we want to ensure we’re fostering a community that promotes engaging conversations, solutions for challenges the team or individuals are facing and as much interaction as possible as we continue to work remotely.

 

What role do your salespeople play in shaping the conversations and decisions that take place in those meetings?

Salespeople are essential in shaping the conversations and decisions. No one wants to sit in a meeting where you are being talked at for 30 minutes, especially via video. Encouraging the team to problem-solve their own blockers by bouncing ideas off one another creates autonomy in the role, leads to higher engagement and morale, and instills confidence in individuals as they continue to develop their skills.

 

Evan Rutchik
Chief Revenue Officer

What they do: Ogury is an advertising engine aiming to create better ways to reach users on mobile devices. Powered by consumers’ choice data, the engine provides targeted ads that are relevant to what users are interested in. 

 

How often do you hold sales meetings with your team? What are the key objectives of those meetings?

In these unprecedented times, I believe it’s important to stay connected and over-communicate to maintain high morale on my teams. Therefore, I’ve implemented multiple cross-region and cross-functional calls, which have resonated very well with my team. 

I aim to accomplish a few things for these meetings. I use them to motivate, roll out new processes, set goals and review where the business currently stands in the quarter to meet our goals. Additionally, I recognize top performers and their teams as well as provide updates on any new products and/or objectives that we are setting. 

Also, we try to have a little fun. 
 

It’s important to stay connected and over-communicate to maintain high morale on my teams.”


What specific actions do you take before or during those meetings to ensure they're productive and engaging?

Typically before these meetings, I write out everything that I plan to present and create an agenda to make sure that I share all of the major points and updates that are necessary to keep our teams productive. 

Additionally, I ask that if anyone on the team has any questions, they share those with me ahead of time so I can address those questions on the call anonymously. I like to keep an open-door policy for my team and I want to make sure that everyone feels comfortable enough to share their thoughts and feedback.

 

What role do your salespeople play in shaping the conversations and decisions that take place in these meetings?

Our sellers play a significant role in shaping the conversations that take place for our strategies. They are the ones who see what’s happening in their markets and gather the best insights from our clients to help influence the course of our strategies and goals. 

They also play a huge role in positively motivating the rest of the team. Bill Belichick, the legendary coach of the New England Patriots, my favorite team, said it best: “On a team, it’s not the strength of the individual players, but it is the strength of the unit and how they all function together.”

Philip Gude
VP Sales & Customer Success, Americas

What they do: AB Tasty is a platform built to help companies like Wal-Mart, Sephora and Disney optimize their customer experience. As the name suggests, the platform offers tools like A/B testing, along with audience management, progressive deployment and more. 

 

How often do you hold sales meetings with your team? What are the key objectives of those meetings?

When it comes to team meetings — as opposed to one-on-one or function-specific meetings —  I prefer to ensure that they are adding value to the team and provide an opportunity for everyone to benefit, learn, grow and develop. We are very fortunate at AB Tasty to have an incredibly collaborative team. This collaboration continues outside of our team meetings, which reduces the need for additional meetings. 

Typically, the key objectives of our meetings include a number of topics which surface in my one-on-one meetings and indicate a trend and a need to dive deeper. For example, these trends could be roadblocks in moving flagship prospects forward, challenges around a sales demo account, and creative ways of overcoming those issues.
 

I typically learn about areas of interest or pain-points in my one-on-one meetings.”


I like to give my team members the opportunity to share their takes on team meetings and run them in the way they think would be most useful from their point of view, so that we can continue to get fresh approaches as a team. To do this, once every two months — sometimes more frequently — I have someone from the team lead the meeting themselves and encourage them to try new approaches and segments to keep things fresh.

 

What specific actions do you take before or during those meetings to ensure they're productive and engaging?

In addition to choosing team members to run and lead the team meetings on a regular basis, I also invite guest speakers to share about their specialty. In the past, when my teams were larger, I would do simple two-question surveys to find out what was helpful and useful — as well as what was not helpful or useful — to sales people in a team meeting setting. We also covered what they would like to see incorporated into team meetings.

 

What role do your salespeople play in shaping the conversations and decisions that take place in those meetings?

Salespeople have to play an active part in shaping these conversations for them to be useful. I typically learn about areas of interest or pain-points in my one-on-one meetings with each salesperson and from those, I get ideas about what could result in an engaging team discussion.  

As far as decisions that take place in the meetings, I always ask everyone to share their opinion about a direction we are moving in, as a team or as a company. Everyone is encouraged to share views, which we have no issues getting as we have a very open and collaborative team. Then, I answer any concerns to explain the why behind any decision. 

This is absolutely key and essential, as most people will be more likely to align with a direction when they know the reasons for it. A practical example of this was a study involving people asking to cut in line. When no reason was given as to why they needed to cut was given — even if the person was incredibly polite and nice about it — a vast majority of people in line did not let them. 

We discuss these decisions together as a team to make sure that everyone is on board and we can move forward on implementing it.

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