Ever had that sinking feeling when you realize one of your reps isn’t hitting quota? You know the name: maybe Maya or James. They were once a star performer, or a promising new hire — and suddenly the numbers aren’t there. As a sales leader, you’re anxious. The team is depending on results, but a harsh reprimand could shatter morale. The last thing you want is a discouraged rep walking out the door (or worse, staying stuck in a rut).
“When leaders obsess over the small things, the big things quietly begin to fall apart.”
Coaching an underperformer is a delicate balance of high standards and genuine care. The key is to be tough on the problem, not the person. Dig deeper than excuses, and treat the situation as a shared puzzle — not a flaw in their character.
I remember talking with “Maya” (not her real name). She used to close big deals, but recently had been avoiding calls and missing pipeline targets. Instead of firing off a stern email, her manager pulled up a chair beside her one Monday morning and simply asked, “I noticed your numbers dipped last month — how are you feeling about everything?”
That one empathetic question broke the ice. Maya confessed she felt overwhelmed by a recent software change and doubted her product knowledge. Together, they created a small but powerful plan — training refreshers plus a few warm, low-stress accounts — to rebuild her confidence.
This curiosity-first approach transforms coaching from intimidating to supportive. As one sales coach explains, “By showing empathy and curiosity, you signal that you are there to support their growth rather than simply criticize their performance.” In other words: start by listening. Create a safe space for honesty. Ask open-ended questions like:
“What’s feeling hard right now?”
“What do you think is holding you back?”
Managers who invest time in thoughtful questions build trust — and trust gives you the real story behind the numbers.
Dig Deeper: It’s Mindset, Process, or Fit — Not Laziness
After building trust, diagnose the real issue. Underperformance is rarely laziness. It usually stems from:
A shaky mindset
A broken process
A role mismatch
Missing skills or training
As one analysis notes, performance crises are often symptoms of “outdated processes, misaligned priorities, or gaps in onboarding.”
“Underperformance is rarely laziness — it’s a signal: check the mindset, fix the process, or re-seat the fit.”
For example: A rep who hates cold calling will always lag if half their week is spent dialing. A senior rep struggling with new CRM tools may waste hours on admin instead of selling.
These aren’t motivation issues — they’re fit and process issues.
To uncover root causes, try the Five Whys technique:
“Why aren’t you hitting call quotas?”
“Why does the script feel uncomfortable?”
“Why does handling objections create anxiety?”
Eventually, the real barrier emerges — maybe fear of rejection or lack of clarity. Now you can coach the real problem, not the surface symptom.
Also look for misalignment. Many “underperformers” simply sit in the wrong seat. A relationship-builder forced into aggressive outreach will struggle. A strategic thinker forced into high-volume calling will burn out fast.
Sometimes the right solution isn’t more pressure — it’s better alignment.
Build Trust with Accountability, Not Micromanagement
Once you’ve diagnosed the issue, set clear expectations together. There’s a world of difference between accountability and micromanagement.
Accountability: “I trust you. Let’s agree on goals and track progress.”
Micromanagement: “I don’t trust you, so I’m watching every move.”
“Accountability empowers — micromanagement restricts. Choose the one that grows your team.”
Leaders should always aim for the first.
Instead of saying: “Your numbers are down 30% — fix it.” Try: “Here’s the goal. Let’s map out what you need to hit it — and how I can support you.”
Set weekly 1:1s focused on solving problems, not delivering lectures. Ask:
“What worked this week?”
“What’s blocking you?”
“Where do you need help?”
And when they make progress — even small progress — celebrate it. A single booked demo, a single clean objection handle, a single confident call… it all matters.
Take a “trust but verify” approach: “You own the 20 calls daily. I’ll check in Friday to review your progress — I know you’ve got this.”
This balance builds confidence while keeping standards high.
Fuel Confidence with Strengths and Small Wins
Underperformers often carry emotional bruises. They’ve heard “no” too many times. The coaching goal is to rebuild belief.
Start with strengths, not weaknesses.
Are they a great storyteller?
Strong in demos?
Great with warm leads?
“Big confidence is the sum of many little successes.”
Let them shine where they’re naturally strong, then gradually expand into weaker areas.
Set tiny, achievable goals — “quick wins” — and celebrate them loudly. Even one successful call can shift their mindset from “I can’t” to “Maybe I can.”
Make progress visible. Track wins in your CRM or on a shared board.
And always praise effort, not just results. Reinforce good behaviors when you spot them. Use practice tools like role-play to build skill in a safe space.
Confidence doesn’t return overnight — but it builds faster with consistent wins.
When Coaching Isn’t Enough
Sometimes, despite consistent coaching, effort, and clear expectations, the rep still doesn’t improve. At this point, it’s time for a direct but compassionate conversation about fit.
Say something like: “You’ve worked hard, and I appreciate the effort. But we’re still not hitting the bar. Let’s talk about next steps.”
Explore options:
A different role
A different focus area
A structured PIP
Or, if needed, a respectful transition
“Sometimes coaching can’t fix the fit — and recognizing that is a sign of true leadership.”
This conversation should feel fair, honest, and human. A struggling rep deserves clarity — not confusion, shame, or surprises.
Sometimes the kindest thing you can do is help them move into a place where they can truly thrive.
Takeaways: Coach with Compassion and Clarity
Start with empathy and honest listening.
Diagnose the real issue — mindset, process, or fit.
Set clear expectations, but avoid micromanagement.
Celebrate small wins to rebuild confidence.
Know when to shift roles or make a tough call.
“Compassion guides the conversation; clarity guides the results.”
Coaching a struggling rep is never easy, but your job isn’t just to manage numbers — it’s to develop people. When you combine compassion with high standards, underperformance becomes an opportunity for transformation.
And sometimes the biggest surprise is this: The rep you thought was falling behind may become your biggest comeback story — simply because someone believed in them.
