Outbound Day 1 VIP – Getting Sellers to Follow Up

Recapping Outbound 2024
Over the next few weeks, I’ll share insights and key takeaways from my time at Outbound 2024 in San Antonio. Day 1, the VIP day, kicked off with thought-provoking discussions among sellers and sales leaders. One standout topic was a recurring challenge in sales:

“How do we get our sellers to follow up?”

Why Sellers Don’t Follow Up

We identified two primary reasons sellers often fail to follow up:

  1. Shiny Object Syndrome
    Sales reps get distracted by the whirlwind of their day, constantly chasing the next opportunity instead of focusing on follow-through.
  2. Fear of Conflict
    Without setting next steps during initial meetings, reps worry that asking for them later might feel uncomfortable or unprofessional.

Strategies to Make Follow-Up Easier

We explored practical ways to encourage follow-up and make it a natural part of the sales process:

  • Send thank-you notes: A simple thank-you card or email post-meeting builds goodwill and keeps the conversation going.
  • Reframe the mindset around sales: Selling isn’t a “dirty word.” Success comes when reps embrace their role and understand that follow-ups drive progress.
  • Flex selling styles to match buyers: Adaptability is key. Encourage reps to align their approach with the buyer’s preferences.
  • Collaborate across teams: Inside sales, outside sales, and customer service teams should work together seamlessly to manage relationships and ensure follow-ups don’t fall through the cracks.
  • Leverage tools like CRMs and AI: These tools streamline follow-up processes, helping reps stay organized and on task.

Segmenting Deals for Better Follow-Up

Not all deals are created equal. We discussed creating targeted follow-up lists:

  • Hot List: Urgent deals requiring immediate action.
  • Medium List: Promising opportunities needing consistent follow-up.
  • Slow List: Long-term prospects that need nurturing.
  • Dead List: Deals unlikely to close, requiring minimal effort.

Encourage reps to end each day with a recap:

  • Document everyone they spoke with.
  • Write two sentences summarizing follow-up steps.
  • Schedule next steps before leaving the call or meeting—always confirm dates and times.

Building a Follow-Up Culture

As sales leaders, it’s our responsibility to coach and equip teams with the right tools and templates. Key practices include:

  • Pipeline reviews: Reps can’t forecast deals without clearly defined next steps.
  • Clarity and consistency: Set expectations and communicate the “why” behind any process changes.
  • Lead by example: Show up, walk the talk, and model the behaviours you expect.

The Role of Accountability

Accountability isn’t micromanagement; it’s a leadership cornerstone. To implement change successfully:

  • Highlight wins: Demonstrate how discipline and process drive results.
  • Tap into competitiveness: Most sales teams thrive on competition—use it to foster accountability.
  • Drive behavioural change: No change occurs without a shift in habits. Leaders must lead by example and invest in proactive coaching.

A Leader’s Responsibility

If a rep fails, leaves, or is terminated, it’s on us as leaders. Without investing in coaching, we cannot claim “clean hands.” Leadership means owning the process, the team, and the outcomes.

This barely scratches the surface of what we discussed during VIP Day at Outbound 2024. Sales is a deep, complex world, and I’m always happy to dive deeper into these topics—just let me know what you’d like to hear more about.

Cheers,
Kyle Jager

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