2026 Selling Challenges Research Study
Improving win rate
Written by: Ben Taylor, MBA, Content Marketing Manager, Richardson
Published: March 12, 2026
What's Inside
In our annual Selling Challenges Research Study, we asked over 300 sales and enablement professionals about the biggest challenges they're facing in today's selling environment. This year's results reveal something surprising: for all the AI noise, the biggest challenges in sales are still the human ones.
Aligning stakeholders. Creating urgency. Delivering meaningful insights. These are the human skills that decide whether a seller will confidently guide customers through difficult decisions—or stay stuck in the confidence chasm.
In this report, we explore the industry’s most pressing problems and offer ten shifts leading organizations can make to build confidence and win more in 2026.