5 Data-Driven Topics Sales Leaders Need to Include In Their 2018 Sales Kickoff

By: Teresa Weirich

February 5, 2018

Each January, sales organizations across the globe gather together to share best practices, learn together, and tell war stories of the big deal that was finally inked at midnight on New Years Eve, or the one that got away. Sales kickoffs can be extremely valuable not only to sales professionals, but to sales leaders, executives, and other leaders across the business. There’s certainly something to be said about looking back and learning from sales processes that went according to plan while making adjustments based on learnings from the deals that weren’t as fortunate.

As we near the end of 2017, NOW is the time that sales leaders need to stop and reflect on another year gone by. It’s time to carefully plan a sales kickoff agenda that will not only be helpful to sales professionals through just the week of February, but for the entire 365 days of the year. While there’s no magic formula for success, there is a common theme that should be present in every single topic: Data. Reviewing performance metrics, addressing qualification issues, and identifying just where deals go to die in the sales process are relevant topics that should be included in the kickoff. So before planning a role play exercise based on personal preference for call handling, try adding these 5 data-driven topics:

1. 2017 Key Sales Data

Meaningful sales data can be difficult to come by. Sure, Sales Ops likely has spreadsheets upon spreadsheets of individual rep performance, the percentage of reps that attained quota, and maybe even a breakdown of the number of deals that progressed or went dark at each stage. However, sales data is often calculated manually or can only be compiled by filtering complex reports or through a limited visibility Salesforce.com dashboard—and still, the numbers lack context. When given visibility into meaningful sales data, team members can learn just as much from the metrics as Sales Ops can. Sales leaders that take a transparent approach and walk through easy-to-interpret reports during the sales kickoff will help team members identify correlations, but also feel empowered to make recommendations for how to iterate on the process either individually or as a team.

Rather than kickoff the all-important sales meeting with a repetitive presentation about the importance of attaining quota, instead share meaningful data accessible from an agile sales platform:

  • What factors were present in both wins and losses
  • The top objections that were seen most often and at which stage
  • What happened when the right decision makers weren’t involved
  • Best and worst performing discovery questions
  • How long was the sales process when a compelling event wasn’t identified

2. Company Messaging and Persona Review

Sales leaders that can identify just where in the sales process team members get hung up on messaging can be invaluable for helping them improve their conversations. The challenge is, most sales leaders coach their team members during 1:1 meetings, but lose sight of exactly how the sales professional handled the question, response, or messaging point during the prospect conversation. Even worse, coaching often has to rely on personal preference rather than data points that accurately show at which point the sales professional forgot to ask a key question, went off-script, or didn’t articulate the messaging correctly.

The annual sales kickoff is a great time to revisit company messaging, value propositions, and personas, and also share coinciding metrics with the entire team for their valuable input. Afterall, they’re the ones having the prospect conversations day in and day out! Since the key messages evolve over time, consider using an agile sales platform during the sales process so that the sales team always has access to the messaging when they need it most: while they’re in conversation with a prospect.

3. Qualification and Pipeline Progression

MarketingSherpa found that 57% of B2B organizations identify “converting qualified leads into paying customers” as a top funnel priority. With the urgency of closing deals in mind, the qualification process can ultimately suffer if sales leaders don’t enforce proper qualification and how a lack of doing so negatively affects every part of the sales process thereafter. Upon reviewing call details and looking at the pipeline, sales leaders will many times find deals that should have been disqualified during the first conversation progress to the mid stages of the sales cycle before the deal ultimately meets its fate: a painful “no” or worse, a prospect that goes dark without explanation.

The good news is that these pipeline problems can be addressed by examining data that surrounds the qualification process: the questions asked, the answers received, and the action items taken. Using the sales kickoff as a time to review the qualification process and take a look at the pipeline progression—all enforced by data that indicates what’s working and what’s not—is an excellent use of time that will help sales professionals identify practical ways that they can improve.

4. Win/Loss Analysis

Deals are won and lost for a variety of reasons. With the help of data, sales leaders can point to when and where a deal went wrong and, similarly, they can pinpoint factors that were involved in deals that closed. It’s common for sales organizations to role-play different scenarios or even do a “show and tell” of wins and losses. However, it’s far more uncommon for sales leaders to show visuals of which factors were involved for each win and each loss so the sales team can learn not just from one sales professional recounting a deal, but from the data itself. At the 2018 kickoff, let the data speak for itself and tell the story of wins and losses across the board—not just the highlights. By reviewing trends and identifying ways the sales team can improve together, every single quota contributor (and the company’s bottom line) will benefit.

5. Objection Handling

Last but certainly not least, the topic of objections is something we’ve covered before due to its importance—they’re present in every single deal, virtually without exception. The problem most teams face is that objections aren’t handled early enough in the sales process. Many sales professionals will ignore buyer signals, hoping that the objections will disappear if they don’t confront them. However, the exact opposite is true. The earlier an objection is confronted by the sales professional, the better chance he has to overcome it at that moment or prepare to address it in the future.

The sales kickoff is a prime opportunity to not just practice objection handling, which tends to be a fall back exercise for sales leaders, but share with the entire team the root of the objection issues:

  • What are the objections that the sales professional should be prepared to answer?
  • When and how should objections be addressed by the sales professional?
  • What responses or actions should the sales professional take?
  • What factors constitute when a prospect should be disqualified

When sales leaders are armed not just with the top objections asked by prospects, but with metrics that indicate objection handling effectiveness, they’re able to do more than lead a role play session—they can change the future of the sales process.

Let 2018 be the year of the agile sales team—a team that continually learns, evolves, and grows together. And it can all start by making data the foundation of the next year’s sales kickoff.


  • Teresa Weirich's Headshot
    Teresa Weirich

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