3 Challenges & Benefits of Team Selling

Think of Dennis Rodman - arguably one of the greatest rebounders in NBA history. Yet he never thrived as "the star." Put him on a team with Michael Jordan and Scottie Pippen though? Five NBA championships. Rodman knew his role, mastered it, and made the entire Chicago Bulls organization better by focusing on what he did best while letting others shine in their areas of expertise.

The sales landscape today is a lot like those championship Bulls teams. Gone are the days of the lone wolf closer - the Michael Jordan who could supposedly do it all. Today's complex deals and sophisticated buyers demand a Rodman-like recognition that different players bring different strengths. That's where team selling comes in - but like Phil Jackson orchestrating those Bulls championships, implementing a team selling strategy requires careful planning and the right players in the right roles. Let me share how team selling works and why it's becoming a secret weapon for driving better results in your sales cycle.

If you prefer to listen to our conversation about this topic on the go, feel free to check out sALES with ASLAN podcast episode 67:

The Benefits of Team Selling

When we don’t “team sell,” it hurts our ability to win. Period. 

When we don't leverage team selling, it's like fielding a basketball team of five point guards. Sure, they can all dribble and pass, but who's getting the rebounds? Who's protecting the rim? When we've closed significant deals, it's because we had our full cross functional sales team on the court - each player knowing their role and executing it perfectly.

Think about your current sales process. Just like Rodman wasn't trying to outshoot Jordan, no single sales rep should feel pressured to excel at every aspect of complex deals. Some are natural at prospecting and qualifying leads - your "floor generals" who can see opportunities developing. Others are your "closers" who shine in the final stages of the sales cycle. The key is building a sales team that combines these diverse skill sets to create stronger relationships with target accounts.

One sales rep may crush the prospecting process, always cultivating a robust sales pipeline. Another sales rep may thrive in Discovery, uncovering stated needs and revealing problems. 

The idea with team selling is to increase your chances at closing the sale or advancing the opportunity by collaborating within sales teams and other departments of your organization. 

When you show up as a team in front of customers, even in a virtual sales environment, it says something about you and your company. It tells your customer that they are important, that you are willing to put in the work to earn their business and their trust. 

When Do We Use Team Selling?

Think of it like substitutions in a basketball game - knowing when to leverage team selling can be the difference between a stalled sales cycle and a championship-caliber close. Just as a coach wouldn't send in their 3-point specialist during a crucial defensive possession, your team selling strategy needs to match the right players to the right situations.

When Should You Deploy Your Full Sales Team?

• For complex deals requiring multiple perspectives (like the '96 Bulls needed both Jordan's scoring AND Rodman's rebounds)
• When your sales pipeline contains high-stakes target accounts
• During intricate sales cycles where technical expertise is crucial
• To reinvigorate stalled opportunities with fresh sales approaches
• When prospecting and qualifying leads require diverse skill sets

Let's break down some game-winning plays:

The Technical Timeout Play

Your account executive has built strong customer relationships but needs your sales engineer's technical expertise for the product demo. Like a point guard working with a power forward, each brings different skills that create a smoother sales process.

The Executive Fast Break

When selling to key stakeholders at the C-level, bringing in your own executive leadership isn't just about status - it's about providing better insight and demonstrating your company's expertise. This collaborative approach often leads to closing deals more effectively.

The Full-Court Press

For operationally complex sales cycles, involving other team members from different departments creates a comprehensive strategy that addresses every aspect of customer success. Think of it like a full-court press - everyone has their zone to cover, but they're all working toward the same goal.

The Legal Defense

Sometimes you need your legal team on the court to handle complex contract negotiations - they're like your defensive specialists, protecting everyone's interests while keeping the deal moving forward.

The real power of team selling comes from treating each stage of your sales process like a carefully planned game strategy. Your cross functional sales team becomes more effective because each player knows exactly when to step in and how to handle complex deals. Just as a championship team needs both starters and specialists, successful team selling helps sales reps leverage the right tools and expertise at the right time.

This team selling approach doesn't just lead to more deals - it creates a stronger overall customer experience because you're bringing your full roster of expertise to every opportunity. And just like great teams improve through practice, your sales performance grows stronger as team members learn from each other's techniques and approaches.

The Challenges of Team Selling

Probably a good time to ask: if this works so well, why aren’t we doing it? I’ve got some insights into that.

Playing Hero Ball Doesn't Win Championships

Remember Allen Iverson? Incredible talent, but never won a championship trying to do it all himself. I've met many sales reps who approach their sales process the same way - hesitant to implement team selling because they want to run the entire sales cycle solo. Like a player who won't pass the ball, they think closing deals alone means more glory (and commission).

But here's the reality check: your sales pipeline isn't about individual stats. Just as the Golden State Warriors revolutionized basketball with their "strength in numbers" approach, modern sales strategy requires leveraging team selling to handle complex deals effectively.

Ask yourself: "Am I really using my cross functional sales team to maximize our competitive advantage?" Remember, customer success comes from putting the right players in the right positions. Be Other-Centered® - sometimes that means letting your sales engineer take the technical lead while you focus on the customer relationship.

#2 – Coordinating Your Dream Team

Picture the 1992 Dream Team - all that talent could have been chaos without a clear strategy. The same goes for your team selling approach. When multiple team members engage with target accounts, you need a game plan to create a smoother sales process.

Here's how to coordinate your sales team effectively:

• Hold regular meetings to align your comprehensive strategy
• Create clear account maps defining each player's role
• Establish who handles different aspects of the sales cycle
• Develop protocols for customer engagement at each stage
• Set up a clear reward system that encourages collaboration

Think of yourself as the point guard of your team selling efforts. Your job is to:

• Direct traffic during customer interactions
• Know when to bring in other departments for maximum impact
• Maintain clear communication across your tech stack
• Ensure every team member understands their role in qualifying leads and moving opportunities forward

#3 – Fear of Being Outshone

Here's where we return to Dennis Rodman's wisdom. He knew that letting Jordan take the spotlight while he dominated the rebounds created better results for everyone. Some sales reps fear that bringing in other team members with strong sales performance records might make them look bad.

But successful team selling works like a championship roster:

• Different players bring diverse expertise to the sales process
• Various skill sets combine to handle complex deals
• Multiple perspectives provide better insight into pain points
• Cross-departmental collaboration builds stronger relationships with key stakeholders

Remember: the best sales leaders, like the best team captains, don't fear being surrounded by talent - they embrace it. When you leverage team selling effectively, everyone in your sales organization wins bigger deals and creates better customer experiences.

"With the right preparation and diversity of skills coming into any deal, there's no reason to fear the team selling approach. It's about making the whole team better." – Scott Cassidy, former VP of Marketing at ASLAN

You are the (Team Selling) Champions, My Friends

Just as the greatest sports dynasties weren't built on individual talent alone, today's most successful sales organizations understand that the "lone wolf" era is over. When you implement team selling effectively, you create a sales process that's greater than the sum of its parts. Your sales reps become more confident, your customer experience improves, and your sales cycle becomes more efficient.

Like a championship team, each player knows their role - from prospecting and qualifying leads to providing technical expertise and closing deals. The competitive advantage doesn't come from having the best individual performer; it comes from having a cross functional sales team that knows how to work together towards a common goal. So take a page from the greatest teams in sports history: embrace collaboration, leverage diverse expertise, and watch as your team selling approach transforms good opportunities into great victories. The trophy for customer success goes to those who know how to play as a team.

If you want to take this idea further, go watch Brené Brown’s TED Talk on The Power of Vulnerability.  It’s extremely powerful and very relevant to this topic.