A Guide to Building a Healthy Sales Culture (Including Team Building Activities!)

All of the comradery and none of the cutthroats.

If I asked you to describe a typical sales culture, what would you picture? Fast-talking men in suits boozing and schmoozing with clients over drinks? Traveling vendors with briefcases upselling their wares? I, for one, would think of that scene in the first episode of Succession, where a bunch of grown-up frat stars drop f-bomb after f-bomb as they hype up the deal they're trying to close.

And I'm not the only one whose mind goes there; a 2006 academic study found that media descriptions of the sales occupation were "overwhelmingly unflattering and negative."

Sales can have a reputation for being a cutthroat, manipulative, greedy, and dishonest boys' clubs with high turnover and lots of stress. Those media portrayals were often based on real-life experiences, were they not?

But sales doesn't have to be like that. Building a healthy sales culture that encourages collaboration while still rewarding performance can help you create a sustainable sales team that lets its members and your business thrive. And a healthy sales culture is one more likely to make women and underrepresented minorities feel comfortable and flourish, bringing much-needed diversity of perspectives and market understanding to your business (and the results to show for it—companies with 45% or more women in their sales teams have higher-than-average profits).

This article will highlight common mistakes found in sales teams and provide advice from seasoned sales managers to help you build a better sales culture.

Common mistake: "You're on your own" mentality where each salesperson is responsible for figuring out best practices.

Why it happens: "Sales is hard and requires more than just product knowledge to be successful. Many companies treat sales as a natural ability and not something you can learn," says John Hill, founder of CRM customization company Adapted Growth and host of the Sales Throwdown podcast.

What you can do about it: Focus on training and mentoring and make those responsibilities an explicit part of your management meetings as well as how you grade and compensate your most senior and successful people.

And in your training sessions, consider a wide range of useful skills beyond the core components of prospecting and closing. "I train only 25% of their time in sales tactics and 75% of their time in self-development, compassion, and empathy," says Abbie Mirata, founder of non-profit Kyndly. "The more a salesperson feels confident and valued and not afraid to make mistakes, the better they will eventually become. They will also build stronger customer relationships and close more deals when they have real care and compassion for what a customer needs."

Chris Mason, senior vice president of sales distribution for HealthMarkets, suggests creating a sales culture of abundance versus scarcity: "One team member having great success doesn't detract from others' opportunity; conversely, it shows what is possible for others, that systems work [and that] products are relevant in the market." Make sales success post-mortems an agenda item on every team meeting, where the salesperson who closed the deal walks the team through what they did, what worked and what didn't, and how others can find similar success.

Common mistake: Measuring results on an individual basis versus a team basis, which leads to risk with top performers and resentment from less-than-stellar performers.

Why it happens: Salespeople are often compensated on whether or not they hit certain targets, so some managers will only measure results on a person-by-person basis, leaving behind the overall synthesis of the team's direction.

What you can do about it: Create team targets and widely publicize them. "Many years ago I worked for one company that would regularly shoot itself in the foot by setting an individual target [where] as soon as you hit it, you [could] go home," says Kim Adele, a leadership coach and former C-suite executive. "I amended it to be a team target. [It was] a small change, but the team spirit it built was amazing and we went on to have double-digit growth and a really engaged team," she says.

As vice president of accounts at youth sports advertising firm LeagueSide, Jason Smith notes the importance of making sure you are capturing and systemizing your top performers' success tactics and publicizing them to the rest of the team. "A lack of managerial leadership to replicate [success] often has led to resentment and jealousy," he says. At team meetings, give updates on overall success and on collective improvement to processes to make everyone feel like they're in it together.

Common mistake: Isolating the sales team from each other and/or from the rest of the company, leaving them feeling less attached to their team and the company's overall mission.

Why it happens: "[People] think about salespeople as lone wolves," says Yuval Shalev, co-founder of enterprise sales platform Hunterz. Because salespeople often work away from the office and may not have many full-team touch-points, fostering connection can be hard.

What to do about it: Invest in team-building within your sales team and between your sales team and the rest of the company can help reduce turnover and motivate employees, says Shalev.

For team-building with your sales group, try these ideas:

  • Take group personality tests and discuss the results. Try the Myers-Briggs, True Colors, DiSC, or other test options and break up into groups by results, discussing preferences about communication strategies, weaknesses at work, and how to collaborate effectively between different types of people.
  • Plan (or outsource) a scavenger hunt. If you have the time and the creativity, develop a daylong activity that requires teams to work together to solve puzzles, take pictures, and get to a certain site together (where they'll find food and drinks to celebrate with). If you'd rather have a pro take care of the logistics, look for a scavenger hunt company or book a slot at an escape room.
  • Volunteer as a team. Remember and reinforce that you're all in this together by pooling your time and skills to help out in your community. Look for a Habitat for Humanity build opportunity, sign up for a shift cooking and serving dinner at a soup kitchen, or volunteer to clean up a park in your neighborhood. If you're an all-remote team, give everyone some time off to complete projects together on volunteer skills-sharing site Catchafire and have a debrief session to talk about what they worked on.

For team-building within your sales team and the rest of your company, try one of these:

  • Celebrate wins together. Smith shares his team's tradition: "A Slack message [goes] out to the entire company announcing the deal, followed by the team member who closed the deal banging on a big gong in the office. It makes the whole team (not just the sales team) feel involved and pushes everyone to work harder. It's led to great feedback and a feeling of inclusion from the whole team."
  • Encourage collaboration and connection with inter-departmental competitions. Mirata suggests instituting Random Acts of Kindness weeks, where employees seek to recognize or support their coworkers by cleaning up common areas, sharing unprompted compliments or kudos, or treating someone to coffee or lunch.
  • Plan a company-wide field day. Invite everyone to a park, break them into 3-4 big teams with lots of mixing between departments, and put them through all the activities of your elementary school days of yore: balancing an egg on a spoon, three-legged races, blind obstacle courses where one person gives directions to someone wearing a blindfold, and as many pie-eating competitions as their stomachs can take.

Building A Healthy Sales Culture Takes Leadership

Overall, remember that a sales team manager's biggest responsibility is to lead their team to success. That means listening well, adjusting plans and processes to fit your team's needs, hiring and compensating your team fairly, and knowing when to hold your team accountable and when to celebrate. It's a tough job, but if it interests you—and you don't already have that responsibility set—check out the 500+ open Sales Manager jobs on PowerToFly.


Want to learn more about how PowerToFly can help you build a diverse and inclusive culture? Contact us here.

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A Night of Networking with Peloton’s Women Tech Leaders

If you are a New York based tech professional and you'd like to attend this event, please email your name and LinkedIn URL to

Whether you are a software engineer, fitness enthusiast or both, you won't want to miss PowerToFly's evening of product demos and networking with the women tech leaders and allies at Peloton.

Founded in 2012, Peloton brought top talent together in its Silicon Alley headquarters to create a new concept in fitness. In their words, "We loved cycling but had a hard time finding a workout that consistently fit our schedules, and our at-home workouts never felt quite up to par. So, we set out to create a world-class indoor cycling studio experience on your time, and in the comfort of your own home."

This event is your chance to hear directly from the women tech leaders and allies who make their revolutionary products like the Peloton Bike, Peloton Tread and Peloton App possible. We'll be devoting a large portion of the event to taking your questions and I know the Peloton team wants to hear from you!

The unique evening will take place on Wednesday, February 12th from 6pm to 8:30pm at 125 W 25th Street.


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