Most sales managers think they’re coaching when they’re actually just telling reps what to do. That’s a problem when it comes to sales performance. Reps who rate their coaching as excellent are 50% more likely to hit quota, but only 19% of reps say their coaching reaches that level. The gap between where coaching is and where it needs to be represents millions in lost revenue. This playbook gives you seven essential conversations that transform how you develop your team.

TLDR:

Reps with excellent coaching are 50% more likely to hit quota, but only 19% rate their coaching as excellent. The gap? Most managers tell instead of ask. Telling creates short-term fixes. Asking creates ownership and lasting behavior change. These seven coaching conversations give sales managers a framework to diagnose problems, develop skills, drive accountability, and build a team that solves their own challenges.

Why Most Sales Coaching Falls Flat

Here’s a hard truth: 30% of sales reps rate their coaching as poor. Another 29% say coaching lacks practical, actionable advice. That’s more than half your team feeling let down by the development they receive.

According to Gallup research on manager effectiveness, 70% of the variance in team engagement stems directly from the manager. Your coaching isn’t just a nice-to-have. It’s the single biggest lever you have to improve performance.

So why does most coaching miss the mark?

The answer is simple: managers confuse auditing results with building skills. They review pipeline numbers. They ask about deal status. They tell reps what they should have done differently. That’s not coaching. That’s supervision with extra steps.

Only 15% of sales managers spend 25% or more of their time on actual coaching. Most spend less than 30 minutes per week per rep. And here’s the kicker: only about 10% of sales leaders have ever received formal training on how to coach.

No wonder the results are underwhelming.

The Coaching vs. Training Distinction

Before we get into the seven conversations, let’s clear up a common confusion.

Training teaches “how to.” It’s about skills, systems, processes, and product knowledge. Training is telling.

Coaching develops thinking and problem-solving. It helps people learn, apply, and grow. Coaching is asking.

According to Forbes research on sales performance, 90% of training learning is lost within a week without coaching reinforcement. Training alone improves productivity by about 22%. But when you combine training with coaching, that number jumps to 86%.

The 70-20-10 rule explains why: 70% of learning happens on the job through experience and coaching. Only 10% comes from formal training.

Use training when the gap is knowledge-based. Your rep doesn’t know how to use the CRM or articulate your value proposition? Train them.

Use coaching when the gap is application-based. Your rep knows what to do but isn’t doing it? Coach them.

The 7 Essential Coaching Conversations

Great coaching isn’t random. It’s intentional. Here are seven conversations every sales manager should master, each designed for a specific purpose.

1. The Goal-Setting Conversation

Use this at the beginning of a quarter, after promotions, or when performance needs a reset. The purpose is establishing clear, measurable objectives that the rep owns.

Questions to ask: “What do you want to achieve this quarter?” “How will you know when you’ve succeeded?” “What would be the best possible outcome for you?”

Listen for specificity. Vague goals produce vague results.

2. The Discovery Conversation

Use this during one-on-ones, performance reviews, or when issues first emerge. The purpose is understanding current reality without judgment.

Questions to ask: “What’s happening right now?” “What have you tried so far?” “What’s working well? What obstacles are you facing?”

Listen for patterns. Where does the rep get stuck repeatedly?

3. The Skill-Gap Conversation

Use this after call reviews, missed opportunities, or when facing new challenges. The purpose is identifying specific development needs.

Questions to ask: “What went well on that call?” “Where do you think things turned?” “What could you do differently next time?”

Listen for self-awareness. Can they diagnose their own performance?

4. The Accountability Conversation

Use this after missed targets, when excuses emerge, or during commitment follow-ups. The purpose is creating ownership and driving action.

Questions to ask: “If all that is true, what are you going to do about it?” “What’s the first step you could take?” “When will you do it?” “On a scale of 1-10, how committed are you?”

Listen for commitment language. “I’ll try” is different from “I will.”

5. The Opportunity Review Conversation

Use this during pipeline reviews, weekly check-ins, or when deals get stuck. The purpose is coaching through active deals strategically.

Questions to ask: “What stage of the buying process is this customer in?” “What are their largest business problems?” “Who else needs to be involved in this decision?” “What differentiates us in their eyes?”

Listen for depth. Surface-level answers signal surface-level selling.

6. The Motivation Conversation

Use this when reps seem stuck, after repeated failures, or when you notice complacency. The purpose is addressing limiting beliefs and reigniting drive.

Questions to ask: “What’s stopping you from achieving your goal?” “If things don’t change, how will that impact you?” “What would it feel like to solve this once and for all?”

Listen for limiting beliefs. Fear of rejection, need to be liked, and self-doubt kill more deals than competitors do.

7. The Development Conversation

Use this quarterly, during annual reviews, or when reps seek advancement. The purpose is long-term growth and engagement.

Questions to ask: “What are your personal and career goals?” “What skills do you most want to develop?” “How can I support your growth?”

Listen for ambition. Engaged reps think about the future. Disengaged reps just think about Friday.

Questions to Ask vs. Advice to Give

Here’s what separates good coaches from great ones: the discipline to ask instead of tell.

When you tell a rep what to do, they might follow your advice. But they haven’t developed their own thinking. They haven’t built the muscle to solve the next problem on their own.

When you ask questions, something different happens. The rep has to think. They have to analyze. They discover their own solutions. And people are far more motivated to act on solutions they created themselves.

According to Harvard Business Review research on sales coaching, good coaching helps clarify whether the issue is motivation or ability. That distinction changes everything about how you respond.

Four questions that work in almost any coaching situation: “What’s on your mind?” “And what else?” “What do you want?” “If all that is true, what are you going to do about it?”

Notice what these questions have in common. They’re open-ended. They put the thinking on the rep. They create ownership.

When is advice appropriate? When there’s a genuine knowledge gap. When compliance is non-negotiable. When time pressure makes coaching impractical. But even then, ask first. You might be surprised what your reps already know.

How Often Should You Coach?

Research from Objective Management Group tells a clear story. Salespeople coached weekly show 9% higher performance than those never coached. Reps coached multiple times per week show 17% higher performance. And those coached daily show a 34% gain in responsibility and 19% gain in motivation.

The pattern is obvious: more coaching equals better results.

Industry best practice puts coaching at 25-40% of a sales manager’s time. Yet most managers spend nowhere near that. Almost half spend less than 30 minutes per week coaching their entire team.

Start by blocking time. Schedule coaching sessions like you schedule pipeline reviews. Make them non-negotiable.

Prioritize your middle performers. They represent your greatest opportunity for improvement. Top performers need less frequent coaching. Bottom performers may need a different intervention entirely. But that middle 60% responds dramatically to consistent coaching attention.

If you want to accelerate leadership development on your team, coaching frequency is where it starts.

Real-World Example: From Telling to Asking

We worked with a sales manager who came up through the ranks as a top performer. He knew the product inside and out. He knew every objection and how to handle it. And when his reps struggled, he told them exactly what to do.

The problem? His team stayed dependent on him. They didn’t develop their own problem-solving skills. Engagement was flat. Turnover was higher than it should have been.

We helped him shift from telling to asking. Instead of providing answers, he started asking questions. “What do you think is happening here?” “What options do you see?” “What would you do if I weren’t available?”

The change wasn’t instant. His reps had to adjust to thinking for themselves. But within six months, quota attainment improved by 15%. More importantly, his team started solving problems without running to him first.

The same knowledge he’d been giving away for free became more valuable when his reps discovered it themselves.

FAQ: What Sales Managers Need to Know

Q: How much time should I spend coaching? A: Industry best practice is 25-40% of your time. Start with 30-60 minutes per rep weekly. Research shows weekly coaching improves performance by 9%; multiple times weekly improves it by 17%.

Q: What’s the difference between coaching and training? A: Training teaches skills and knowledge through telling. Coaching develops thinking and problem-solving through asking. Training alone improves productivity 22%; coaching plus training improves it 86%.

Q: How do I know if my coaching is effective? A: Track quota attainment, win rates, and deal velocity. Ask reps directly about coaching quality. If reps leave sessions uncertain about next steps, your coaching needs work.

Q: What if a rep keeps making the same mistake? A: Repeated issues without improvement usually signal a limiting belief, not a skill gap. Shift from tactical coaching to mindset coaching. Ask what’s really stopping them.

Q: What if I was never trained to coach? A: You’re not alone. Only about 10% of sales leaders have received formal coaching training. Start with asking more and telling less. Consider formal development through programs like ASLI’s sales management coaching.

Q: How do I coach remote teams effectively? A: Use video for coaching sessions. Review call recordings together for real-time feedback. Maintain consistent cadence regardless of location. Technology enables coaching but doesn’t replace conversation quality.

Key Takeaways

• Reps with excellent coaching are 50% more likely to hit quota, but only 19% rate their coaching as excellent.
• 70% of team engagement variance comes from the manager. Coaching is your highest-leverage activity.
• Coaching plus training improves productivity by 86%; training alone only 22%.
• Weekly coaching improves performance 9%; multiple times weekly improves it 17%.
• Asking questions creates ownership and long-term behavior change; telling creates short-term fixes.
• Use the seven essential coaching conversations to diagnose, develop, and drive accountability.

Great sales coaching isn’t about having all the answers. It’s about asking the right questions at the right time. The seven coaching conversations in this playbook will transform how you develop your team, if you actually use them. Start with one conversation this week. Ask more, tell less. Watch what happens when your reps start solving their own problems. If you’re ready to take your coaching skills to the next level, schedule a consultation with ASLI and discover how our sales management coaching program helps managers become the coaches their teams deserve.