The Broken Coaching Loop 🌀
Why Sales Coaching Fails and What to Do About It
✏️ by: Tiller HQ
📅 published: May 25
📈 for: Sales leaders, Head of Sales, Sellers
Sales coaching is an ongoing and constant challenge for sales leaders. Even when it’s outsourced, it still demands oversight, a big budget sign-off, and a leap of faith that it will work.
Then, just as your team starts to build momentum, you hire new reps and you're right back at square one.
The problem isn’t coaching. It’s the process and implementation.
We call this the coaching loop, the cycle that’s meant to turn insights into action and drive performance. But in most organisations, that loop is broken.
Let’s break it down into four stages and explore where things go wrong.
The Broken Coaching Loop 🌀
Why Sales Coaching Fails and What to Do About It
✏️ by: Tiller HQ
📅 published: May 25
📈 for: Sales leaders, Head of Sales, Sellers
Sales coaching is an ongoing and constant challenge for sales leaders. Even when it’s outsourced, it still demands oversight, a big budget sign-off, and a leap of faith that it will work.
Then, just as your team starts to build momentum, you hire new reps and you're right back at square one.
The problem isn’t coaching. It’s the process and implementation.
We call this the coaching loop, the cycle that’s meant to turn insights into action and drive performance. But in most organisations, that loop is broken.
Let’s break it down into four stages and explore where things go wrong.
The Broken Coaching Loop 🌀
Why Sales Coaching Fails and What to Do About It
✏️ by: Tiller HQ
📅 published: May 25
📈 for: Sales leaders, Head of Sales, Sellers
Sales coaching is an ongoing and constant challenge for sales leaders. Even when it’s outsourced, it still demands oversight, a big budget sign-off, and a leap of faith that it will work.
Then, just as your team starts to build momentum, you hire new reps and you're right back at square one.
The problem isn’t coaching. It’s the process and implementation.
We call this the coaching loop, the cycle that’s meant to turn insights into action and drive performance. But in most organisations, that loop is broken.
Let’s break it down into four stages and explore where things go wrong.
The Broken Coaching Loop 🌀
Why Sales Coaching Fails and What to Do About It
✏️ by: Tiller HQ
📅 published: May 25
📈 for: Sales leaders, Head of Sales, Sellers
Sales coaching is an ongoing and constant challenge for sales leaders. Even when it’s outsourced, it still demands oversight, a big budget sign-off, and a leap of faith that it will work.
Then, just as your team starts to build momentum, you hire new reps and you're right back at square one.
The problem isn’t coaching. It’s the process and implementation.
We call this the coaching loop, the cycle that’s meant to turn insights into action and drive performance. But in most organisations, that loop is broken.
Let’s break it down into four stages and explore where things go wrong.
🔍 Step 1: Identify Coaching Moments
What should we coach on?
Sales leaders are constantly swimming in data. Call recordings, pipeline reports, CRM activity, deal reviews but surfacing clear, actionable coaching moments from that noise is tough.
Where It Breaks:
Insights are buried in hours of calls or spread across tools.
Managers rely on gut feel or anecdotal feedback.
AI tools promise auto-insights, but often flag the wrong things or lack context.
Result: Coaching starts too late or focuses on the wrong behaviours.
💯🚀🎯 Tips 💯🚀🎯
Target 80/20 impact: Yes, they could have demoed a feature in a better way but the customer got it, the objection that wasn’t handled well is what needs to change.
Targeted listening: Instead of broad call reviews, use a scorecard for specific parts of that call e.g. MEDDICC: Out of 5 how effective are they at identifying the actual Economic buyer. Out of 5 how natural was it as part of the conversation. Out of 5 did they gather information on what the Economic buyer looks for?
Quarterly focus: Drive real change by targeting a qualification framework or 3 key objections per quarter.
🔍 Step 1: Identify Coaching Moments
What should we coach on?
Sales leaders are constantly swimming in data. Call recordings, pipeline reports, CRM activity, deal reviews but surfacing clear, actionable coaching moments from that noise is tough.
Where It Breaks:
Insights are buried in hours of calls or spread across tools.
Managers rely on gut feel or anecdotal feedback.
AI tools promise auto-insights, but often flag the wrong things or lack context.
Result: Coaching starts too late or focuses on the wrong behaviours.
💯🚀🎯 Tips 💯🚀🎯
Target 80/20 impact: Yes, they could have demoed a feature in a better way but the customer got it, the objection that wasn’t handled well is what needs to change.
Targeted listening: Instead of broad call reviews, use a scorecard for specific parts of that call e.g. MEDDICC: Out of 5 how effective are they at identifying the actual Economic buyer. Out of 5 how natural was it as part of the conversation. Out of 5 did they gather information on what the Economic buyer looks for?
Quarterly focus: Drive real change by targeting a qualification framework or 3 key objections per quarter.
🔍 Step 1: Identify Coaching Moments
What should we coach on?
Sales leaders are constantly swimming in data. Call recordings, pipeline reports, CRM activity, deal reviews but surfacing clear, actionable coaching moments from that noise is tough.
Where It Breaks:
Insights are buried in hours of calls or spread across tools.
Managers rely on gut feel or anecdotal feedback.
AI tools promise auto-insights, but often flag the wrong things or lack context.
Result: Coaching starts too late or focuses on the wrong behaviours.
💯🚀🎯 Tips 💯🚀🎯
Target 80/20 impact: Yes, they could have demoed a feature in a better way but the customer got it, the objection that wasn’t handled well is what needs to change.
Targeted listening: Instead of broad call reviews, use a scorecard for specific parts of that call e.g. MEDDICC: Out of 5 how effective are they at identifying the actual Economic buyer. Out of 5 how natural was it as part of the conversation. Out of 5 did they gather information on what the Economic buyer looks for?
Quarterly focus: Drive real change by targeting a qualification framework or 3 key objections per quarter.
📢 Step 2: Share With the Seller
How do we deliver coaching?
Once a coaching point is identified, it has to be communicated in a way that’s timely, relevant, and easy to act on. That often doesn’t happen.
Where It Breaks:
Feedback is shared too long after the moment (if at all).
It’s buried in a Slack thread, a long email, or a call that gets rescheduled.
Sellers forget, ignore, or misunderstand the feedback.
Result: Coaching gets lost in translation or in inboxes.
💯🚀🎯 Tips 💯🚀🎯
Focus on 'What,' Not 'Who': Frame feedback around specific behaviours, not personality e.g., say "Let's explore urgency techniques" instead of "You lack urgency."
Make it Two-Way: Encourage sellers to share their perspective. This fosters collaboration, framing feedback as a shared effort to improve.
Connect to Their 'Why': Link feedback to sellers' goals. They're more likely to embrace changes they see as contributing to their personal success.
📢 Step 2: Share With the Seller
How do we deliver coaching?
Once a coaching point is identified, it has to be communicated in a way that’s timely, relevant, and easy to act on. That often doesn’t happen.
Where It Breaks:
Feedback is shared too long after the moment (if at all).
It’s buried in a Slack thread, a long email, or a call that gets rescheduled.
Sellers forget, ignore, or misunderstand the feedback.
Result: Coaching gets lost in translation or in inboxes.
💯🚀🎯 Tips 💯🚀🎯
Focus on 'What,' Not 'Who': Frame feedback around specific behaviours, not personality e.g., say "Let's explore urgency techniques" instead of "You lack urgency."
Make it Two-Way: Encourage sellers to share their perspective. This fosters collaboration, framing feedback as a shared effort to improve.
Connect to Their 'Why': Link feedback to sellers' goals. They're more likely to embrace changes they see as contributing to their personal success.
📢 Step 2: Share With the Seller
How do we deliver coaching?
Once a coaching point is identified, it has to be communicated in a way that’s timely, relevant, and easy to act on. That often doesn’t happen.
Where It Breaks:
Feedback is shared too long after the moment (if at all).
It’s buried in a Slack thread, a long email, or a call that gets rescheduled.
Sellers forget, ignore, or misunderstand the feedback.
Result: Coaching gets lost in translation or in inboxes.
💯🚀🎯 Tips 💯🚀🎯
Focus on 'What,' Not 'Who': Frame feedback around specific behaviours, not personality e.g., say "Let's explore urgency techniques" instead of "You lack urgency."
Make it Two-Way: Encourage sellers to share their perspective. This fosters collaboration, framing feedback as a shared effort to improve.
Connect to Their 'Why': Link feedback to sellers' goals. They're more likely to embrace changes they see as contributing to their personal success.
🧠 Step 3: Seller Applies the Feedback
Do reps know how to implement the coaching?
Even if the feedback is good, sellers need to practice and apply it. This is where real behaviour change happens but only if there’s support.
Where It Breaks:
Reps don’t know what “good” looks like.
There’s no structured follow-up or accountability.
Managers are too stretched to provide improvement in real time.
Result: Feedback sounds great in theory, but nothing changes in practice.
💯🚀🎯 Tips 💯🚀🎯
Knowing vs Doing Gap: Sellers understand concepts but struggle with live execution. Implement real time support.
Habitual Behaviour: Changing ingrained habits requires effort and reinforcement. Real time changes to pitching in a non distracting way.
Lack of Real-Time Support: Sellers lack in-the-moment guidance to apply new techniques. Get Tiller.
🧠 Step 3: Seller Applies the Feedback
Do reps know how to implement the coaching?
Even if the feedback is good, sellers need to practice and apply it. This is where real behaviour change happens but only if there’s support.
Where It Breaks:
Reps don’t know what “good” looks like.
There’s no structured follow-up or accountability.
Managers are too stretched to provide improvement in real time.
Result: Feedback sounds great in theory, but nothing changes in practice.
💯🚀🎯 Tips 💯🚀🎯
Knowing vs Doing Gap: Sellers understand concepts but struggle with live execution. Implement real time support.
Habitual Behaviour: Changing ingrained habits requires effort and reinforcement. Real time changes to pitching in a non distracting way.
Lack of Real-Time Support: Sellers lack in-the-moment guidance to apply new techniques. Get Tiller.
🧠 Step 3: Seller Applies the Feedback
Do reps know how to implement the coaching?
Even if the feedback is good, sellers need to practice and apply it. This is where real behaviour change happens but only if there’s support.
Where It Breaks:
Reps don’t know what “good” looks like.
There’s no structured follow-up or accountability.
Managers are too stretched to provide improvement in real time.
Result: Feedback sounds great in theory, but nothing changes in practice.
💯🚀🎯 Tips 💯🚀🎯
Knowing vs Doing Gap: Sellers understand concepts but struggle with live execution. Implement real time support.
Habitual Behaviour: Changing ingrained habits requires effort and reinforcement. Real time changes to pitching in a non distracting way.
Lack of Real-Time Support: Sellers lack in-the-moment guidance to apply new techniques. Get Tiller.
📈 Step 4: Understand Impact
Did the coaching work?
You can’t improve what you don’t measure. But most teams don’t have a clear view of whether coaching is moving the needle.
Where It Breaks:
No way to track if feedback was implemented.
No link between coaching activity and sales outcomes.
Improvement is anecdotal, not data-driven.
Result: Leaders don’t know if coaching is worth the time or money — and often give up on it.
💯🚀🎯 Tips 💯🚀🎯
Focus on Impactful KPIs: Create a scorecard for the qualification part of the call and track the increase in execution. The other metrics will follow.
Get Specific Feedback from seller: Ask how coaching changed their sales approach and what their remaining challenges are.
Review and Optimise: Find ONE part of the coaching process to optimise in the next month.
📈 Step 4: Understand Impact
Did the coaching work?
You can’t improve what you don’t measure. But most teams don’t have a clear view of whether coaching is moving the needle.
Where It Breaks:
No way to track if feedback was implemented.
No link between coaching activity and sales outcomes.
Improvement is anecdotal, not data-driven.
Result: Leaders don’t know if coaching is worth the time or money — and often give up on it.
💯🚀🎯 Tips 💯🚀🎯
Focus on Impactful KPIs: Create a scorecard for the qualification part of the call and track the increase in execution. The other metrics will follow.
Get Specific Feedback from seller: Ask how coaching changed their sales approach and what their remaining challenges are.
Review and Optimise: Find ONE part of the coaching process to optimise in the next month.
📈 Step 4: Understand Impact
Did the coaching work?
You can’t improve what you don’t measure. But most teams don’t have a clear view of whether coaching is moving the needle.
Where It Breaks:
No way to track if feedback was implemented.
No link between coaching activity and sales outcomes.
Improvement is anecdotal, not data-driven.
Result: Leaders don’t know if coaching is worth the time or money — and often give up on it.
💯🚀🎯 Tips 💯🚀🎯
Focus on Impactful KPIs: Create a scorecard for the qualification part of the call and track the increase in execution. The other metrics will follow.
Get Specific Feedback from seller: Ask how coaching changed their sales approach and what their remaining challenges are.
Review and Optimise: Find ONE part of the coaching process to optimise in the next month.
🚀 Fixing the coaching loop
What steps can I take after reading this to fix this?
Identify: Drive real change by targeting qualification framework improvement
Giving Feedback: Connect to Their 'Why’, link feedback to sellers' goals in a 1-1 this week.
Consistent Application: Find a way to overcome the challenge of getting sellers to apply coaching in real-time.
Focus on Impactful KPIs: Create a scorecard for the qualification part of the call and track the increase in execution.
💯🚀🎯 Tips 💯🚀🎯
Take manageable steps : Focus on 1 thing.
Cost of not fixing: Understanding the financial impact of your problems helps bring them in to focus.
Talk to Tiller: We have seen the same problems over and over again. We would be keen to share how we turn coaching into a repeatable, scalable process.
🚀 Fixing the coaching loop
What steps can I take after reading this to fix this?
Identify: Drive real change by targeting qualification framework improvement
Giving Feedback: Connect to Their 'Why’, link feedback to sellers' goals in a 1-1 this week.
Consistent Application: Find a way to overcome the challenge of getting sellers to apply coaching in real-time.
Focus on Impactful KPIs: Create a scorecard for the qualification part of the call and track the increase in execution.
💯🚀🎯 Tips 💯🚀🎯
Take manageable steps : Focus on 1 thing.
Cost of not fixing: Understanding the financial impact of your problems helps bring them in to focus.
Talk to Tiller: We have seen the same problems over and over again. We would be keen to share how we turn coaching into a repeatable, scalable process.
🚀 Fixing the coaching loop
What steps can I take after reading this to fix this?
Identify: Drive real change by targeting qualification framework improvement
Giving Feedback: Connect to Their 'Why’, link feedback to sellers' goals in a 1-1 this week.
Consistent Application: Find a way to overcome the challenge of getting sellers to apply coaching in real-time.
Focus on Impactful KPIs: Create a scorecard for the qualification part of the call and track the increase in execution.
💯🚀🎯 Tips 💯🚀🎯
Take manageable steps : Focus on 1 thing.
Cost of not fixing: Understanding the financial impact of your problems helps bring them in to focus.
Talk to Tiller: We have seen the same problems over and over again. We would be keen to share how we turn coaching into a repeatable, scalable process.