One of your toughest sales management moments: sitting across from a rep whose numbers aren't hitting targets. You want them to succeed, but quotas and team performance matter too.
Engagement Message
How do you balance support with accountability when a salesperson's struggling?
The key insight: underperformance conversations require both empathy and clarity. Empathy without clarity enables continued missed targets. Clarity without empathy damages relationships and motivation.
You need both to drive results while maintaining team morale.
Engagement Message
When have you seen sales managers lean too heavily toward one or the other?
Before any conversation, diagnose the root cause. Is this a "skill" issue or a "will" issue? Skills can be developed through training and coaching. Will involves motivation, attitude, or engagement with the role.
Same missed numbers, completely different solutions. Getting this wrong wastes pipeline opportunities.
Engagement Message
How might you tell the difference between skill and will problems in sales?
Skill-based underperformance shows up as: high activity but low conversion, asking for help with objections, frustrated by lost deals, or succeeding with warm leads but struggling with cold outreach.
The solution involves sales training, role-playing, better scripts, or shadowing top performers.
Engagement Message
Can you think of a rep who fits this skill-based pattern?
Will-based underperformance looks different: hitting some metrics but not others, inconsistent prospecting effort, attitude changes around certain activities, or avoiding cold calls altogether.
This requires different conversations about motivation, career fit, expectations, or sometimes territory changes.
Engagement Message
What signals suggest a rep's will rather than skill is the issue?
