How to Adopt a Collaborative Culture in Your Sales Team

By: Teresa Weirich

March 14, 2018

In the traditional sense, sales has been viewed as an individual sport. Sure, sales leaders host all-hands meetings, weekly sales huddles, and beginning-of-year sales kickoffs that are typically centered on a group learning environment. However, after each meeting wraps, individual contributors are on their own again: making prospecting calls, creating proposals, and handling objections to improve upon their personal KPIs.

While this type of lone ranger mentality has proven successful for many companies and individual quota bearing sales professionals in the old world of selling, today’s complex, enterprise-focused technology scene requires a very different approach—one of significant teamwork. A collaborative sales culture comes with many benefits, but perhaps the greatest is that nothing has to be sacrificed. Sharing key learnings, working through complex sales processes, practicing objection handling, and breaking barriers across other departments only serves to help everyone and hurt no one (or anyone’s quota, for that matter).

While many enterprise-focused sales organizations are well on their way to a building up a collaborative culture, some are still hesitant to fully adopt this new, adaptive way of agile selling that can only thrive when the entire team is completely bought in. Below, we’ll explore 4 practical ways that your sales organization can start to adopt a collaborative culture:

1. Share Learnings With Sales Supporters Across the Organization

Enterprise sales is anything but a one-man show. Ask any relationship-oriented enterprise sales professional how they won a deal and they’ll list off a number of individuals that each played a critical role in the process: solutions consultants or engineers, sales development reps, field marketing managers, product leaders, implementation consultants and many others.

Jonathan Sherman, one of our People > Process series participants, shared that as an enterprise-focused sales professional, he infrequently takes a meeting on his own. Whether he’s hosting a discovery conversation or an onsite solution presentation, he has team members rallying along with him. He explains it as a “multi-faceted approach to delivering value to large, complex organizations” and it’s this whole-team effort that lands squarely on his shoulders. Jonathan must coordinate and ensure that each individual is engaged, knows their role, understands the customer’s needs, and is an active participant in delivering according to plan.

Sales professionals should take a page out of Jonathan’s book and not only direct cross-department supporters during meetings, but debrief, ask for their feedback, and share learnings to make them feel as though they’re truly on the team (which they are!). This not only helps the supporters improve their performance for future tasks, but also helps the sales professional learn from others that perhaps have deeper subject matter expertise.

2. Adopt a Mentor/Mentee Program Within the Team

Sales organizations—regardless of how many large or small they may be—are made up of professionals with varying degrees of experience. Some may have an older-style approach to selling, others may be incredibly tech savvy, and still others may have no practical experience whatsoever, but have a high degree of integrity and an aptitude for learning.

One of the biggest untruths in building up sales teams is that only a few sales professionals can truly shine at any given time. For instance, if the team already has several ‘A’ players, then others innately are ‘B’ or ‘C’ level contributors. Unfortunately, this mentality can keep more junior sales professionals from rising up and similarly, can cause mediocre sales professionals to believe they’ve hit their plateau.

Adopting a mentor/mentee program across the sales organization by matching up more seasoned sales professionals with others that have experience in different industries or more diverse backgrounds can prove beneficial to everyone. A program such as this can also help to break down barriers that often exist among those in enterprise, field, and corporate sales. For example, one corporate sales professional may have deep experience selling to Director-level purchasers, where as enterprise sales professionals may typically sell to the C-Suite. By teaming up via a mentor/mentee program and approaching deals from unique perspectives, both individuals can benefit, and simultaneously, open doors to further sharing opportunities.

3. Host “Sales Labs” to Experiment With Different Approaches

For an agile sales methodology to truly pay dividends for an organization, continuous testing and optimization is key. However, rolling out new sales scripts, adopting different discovery processes, and re-phrasing value messaging shouldn’t be done ad hoc and certainly shouldn’t be adopted by the entire team without prior rigorous testing.

Chris Dailey, Director of Operations at ValiMail, recently shared with us his team’s unique “Sales Lab” approach, which puts into place a structure for learning from every interaction a sales professional has with their audience. The culture at ValiMail is to review every interaction to better learn about the prospect’s needs and evaluate the effectiveness of their response to those needs. By utilizing this agile approach, Chris and his team can make slight adjustments to qualification questions after analyzing conversations with his team, or he can completely re-engineer a sales touchpoint if the data indicates that the process isn’t working.

By adopting a similar approach to what Chris has implemented at ValiMail, sales leaders can ensure that every team member gains equal visibility into experiments and potential messaging before collaborating on the best path forward.

4. Adopt a Storytelling Mentality Across the Team

KPIs are fundamental to successful sales teams—so important, in fact, that we’ve written dedicated articles to this topic. Yet, as important as numbers are, selling is a human element that shouldn’t remove characters or personalities. Rather than center sales huddles and all-hands meetings around data alone (which sales professionals will inevitably forget hours later), incorporate and encourage moments of truthful storytelling.

As many sales leaders have learned from experience, storytelling is a fundamental art when it comes to establishing credibility, captivating audiences, and ultimately winning trust. Savvy enterprise sales professionals are able to hone in on their prospect’s interests and share stories and case studies that are directly relevant not only to the sales process, but to the stakeholders personally. This truly is an art, and there’s no better place to practice than with the rest of the internal sales organization. To build collaboration among the team, sales leaders should encourage sales professionals to share stories of victory, loss, understanding, and mistakes that they encounter outside of company walls. These stories will not only help sales professionals recall anecdotes better, but they’ll also help to humanize every individual contributor—regardless of their perceived hierarchy or status.

By encouraging storytelling within safe, judgment-free walls, sales professionals will also feel more comfortable selling with a story to prospective and current customers, empowering them to create more productive, career-long relationships.

  • Teresa Weirich's Headshot
    Teresa Weirich

Ready to Learn More?

For more information on best practices of great sales leaders, check out the Costello resources below. If you’d like to see Costello in action, request a personalized demo of our real-time sales playbook software.

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