12 Underrated Sales Coaching Tips & Tricks You Need to Know

August 28, 2024

This one’s for all the sales leaders and managers!
As someone working at Sybill.ai, I've seen my fair share of sales coaching strategies. While our AI-powered sales coach & assistant is a game-changer, we know the human touch in coaching is irreplaceable.
In the fast-paced world of sales, everyone’s looking for that silver bullet—a strategy or a tool that will guarantee success or some relief from all the mountain of admin tasks. But let’s face it, the well-known tips are often overused, and what works for one person might not work for another. So, if you’re looking to up your coaching game, here are 12 underrated sales coaching tips and tricks that might just give you that edge you’ve been searching for.

Oh, and don’t worry—we’ll keep it fun along the way.

1. Master the Art of Listening, Then Listen Some More

For sales reps to be good listeners, just nodding and smiling while your client speaks will not cut it. It’s about understanding the nuances, reading between the lines, and responding to what’s not being said. As a sales manager, you should encourage your reps to ask open-ended questions and then shut up. The silence might feel awkward at first, but it's golden because in the answer lies an opportunity for your rep to fit the product.

2. Embrace the Power of the Pause

Speaking of silence, the pause is an incredibly powerful tool in sales. Teach your reps that a well-placed pause can create anticipation, make their point more compelling, and even give the client space to open up more. It’s like the dramatic ‘smell the fart technique’ that Joey explains and acts in great detail.

Pro tip: If your rep is prone to filling every silence with nervous rambling, suggest they count to three silently after the client finishes speaking before responding or practice the Joey technique.

3. The "Reverse Mentoring" Approach

We often think of coaching as a top-down process, but what if I told you that flipping the script is the real deal? Enter reverse mentoring.

How it works:

  • Pair experienced sales reps with newcomers.
  • Have the newcomers make the pitch and teach the veterans about emerging trends, technologies, or fresh perspectives & the experienced folks could ask potential questions or act out scenarios that have taught them a thing or two about selling the product.
  • Good opportunity for both parties to learn and grow.

This approach not only keeps your seasoned pros on their toes but also empowers your newbies. Everybody wins!

4. Role-Play, but with a Twist

Role-playing is a staple of sales training, but let’s spice things up a bit. Instead of the usual buyer-seller scenario, have your reps role-play as if they were explaining the product to a 5-year-old. This is my favorite question whenever I want to understand something without the jargon & fancy English. “Explain it to me like I’m a 5-year-old” forces reps to simplify their pitch, making it more relatable and less jargon-heavy. Plus, imagining a sweet 5 year old with a candy in their mouth asking, “But but, what’s a CRM?” adds a touch of humor that can lighten the mood.

5. Encourage ‘Failure Fridays’

This one might sound counterintuitive, but hear me out. Failure is the best teacher—if you let it be. Start a “Failure Friday” tradition where your team shares stories & anecdotes from a deal they failed to close and why they think it happened. This normalizes failure, and it also turns it into a learning opportunity.
Remember, as Thomas Edison said, "I have not failed. I've just found 10,000 ways that won't work." Let's help our reps find their light bulb moment!
Bonus: the most epic fail of the month gets a prize. 

6. The "Kaizen" Approach

Borrowed from Japanese business philosophy, the Kaizen approach focuses on continuous, incremental improvement.

How to implement:

  1. Set small, achievable daily goals for each rep
  2. Celebrate minor victories regularly
  3. Encourage reps to suggest tiny tweaks to processes

It's like building a LEGO masterpiece – one brick at a time. Before you know it, you've got a sales team that's as solid as that masterpiece.

7. Break the Routine with Surprise Coaching Sessions

Routine can be the enemy of creativity. Instead of scheduling all coaching sessions, try springing a surprise coaching session, every now and then. Catch your reps off guard (in a good way) with a spontaneous session. The unpredictability keeps them on their toes and mimics real-life scenarios where they need to think on their feet. It breaks the monotony & the process of mugging a pitch. This could be the way to find insights & different perspectives on your product.

8. Incorporate Storytelling into Every Pitch

Humans are wired to respond to stories. Case studies are proven to be one of the most effective conversion methods in B2B marketing because they dive into details of how a product solved a problem, all while having a beautiful story intricately woven with facts & numbers. They make information more memorable and engaging. Encourage your reps to imbibe storytelling into their pitches—whether it’s a success story of how a client used your product or a personal anecdote that relates to the customer’s situation. Stories build rapport and make your pitch more compelling.

9. Leverage AI-Powered Feedback

Thanks to technology, ML and AI have elevated the work-life balance we aspire for. While AI in sales is still underexplored, I think it is safe to say the industry is picking up & delivering at an unfathomable pace. And no, I'm not just saying this because I work at Sybill (okay, maybe a little).

Ways to integrate AI:

  • Use AI-powered tools to analyze call recordings for coaching insights like tone, pace, storytelling, etc
  • Leverage predictive analytics to identify areas for improvement
  • Pick up & learn about potential clients’ non-verbal or emotional cues that could be missed while you are speaking or busy taking notes.

Remember, AI is here to augment, not replace. Think of it as your coaching sidekick, like Robin to your Batman. 

10. Coach to Personality Types, Not Just Skills

In sales coaching, you can’t take the approach of “One size fits all”. Every salesperson is different, with unique strengths and weaknesses. Tailor your coaching to fit their personality types. For example, an introverted rep might excel in written communication, while an extroverted one might thrive in face-to-face meetings. By understanding and leveraging their natural inclinations, you can coach them more effectively.

11. The "Gamification" Revolution

“All work and no play makes Jack a dull boy”. But what if you make work play? Gamifying your sales coaching can boost engagement and motivation.

Ideas to try:

  • Create a points system for different sales activities
  • Set up leaderboards for friendly competition
  • Offer rewards for reaching certain milestones - I’ve never heard a single person complain about extra money being credited to their accounts.

Just be prepared for the occasional "But I called dibs on that lead!" debates. What’s healthy competition without being at each other’s throats? It's all part of the game!

12. Celebrate the Small Wins

In the high-pressure world of sales, it’s easy to focus only on the big deals and forget the small victories. But those small wins—like getting a callback or successfully moving from one stage in the deal to another —are what build momentum. Make it a habit to celebrate these small wins during team meetings. Acknowledging these efforts boosts morale and encourages consistency.

Conclusion

There you have it, folks – 12 underrated sales coaching tips and tricks that can revolutionize your team's performance.
Sales coaching is as much an art as it is a science. While traditional methods are tried and true, incorporating these underrated tips and tricks can breathe new life into your coaching sessions. Remember, sales is about human connection, and the more personalized and empathetic your approach, the more successful your team will be.

And managers, don’t forget to have fun with it—because if you’re not enjoying the process, neither are your reps.

Ready to supercharge your sales coaching with AI-powered insights? Discover how Sybill.ai can help you fine-tune your approach and drive better results.

Get started with Sybill

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Table of Contents

Get started with Sybill

Accelerate your sales with your personal assistant

Get Started Free

This one’s for all the sales leaders and managers!
As someone working at Sybill.ai, I've seen my fair share of sales coaching strategies. While our AI-powered sales coach & assistant is a game-changer, we know the human touch in coaching is irreplaceable.
In the fast-paced world of sales, everyone’s looking for that silver bullet—a strategy or a tool that will guarantee success or some relief from all the mountain of admin tasks. But let’s face it, the well-known tips are often overused, and what works for one person might not work for another. So, if you’re looking to up your coaching game, here are 12 underrated sales coaching tips and tricks that might just give you that edge you’ve been searching for.

Oh, and don’t worry—we’ll keep it fun along the way.

1. Master the Art of Listening, Then Listen Some More

For sales reps to be good listeners, just nodding and smiling while your client speaks will not cut it. It’s about understanding the nuances, reading between the lines, and responding to what’s not being said. As a sales manager, you should encourage your reps to ask open-ended questions and then shut up. The silence might feel awkward at first, but it's golden because in the answer lies an opportunity for your rep to fit the product.

2. Embrace the Power of the Pause

Speaking of silence, the pause is an incredibly powerful tool in sales. Teach your reps that a well-placed pause can create anticipation, make their point more compelling, and even give the client space to open up more. It’s like the dramatic ‘smell the fart technique’ that Joey explains and acts in great detail.

Pro tip: If your rep is prone to filling every silence with nervous rambling, suggest they count to three silently after the client finishes speaking before responding or practice the Joey technique.

3. The "Reverse Mentoring" Approach

We often think of coaching as a top-down process, but what if I told you that flipping the script is the real deal? Enter reverse mentoring.

How it works:

  • Pair experienced sales reps with newcomers.
  • Have the newcomers make the pitch and teach the veterans about emerging trends, technologies, or fresh perspectives & the experienced folks could ask potential questions or act out scenarios that have taught them a thing or two about selling the product.
  • Good opportunity for both parties to learn and grow.

This approach not only keeps your seasoned pros on their toes but also empowers your newbies. Everybody wins!

4. Role-Play, but with a Twist

Role-playing is a staple of sales training, but let’s spice things up a bit. Instead of the usual buyer-seller scenario, have your reps role-play as if they were explaining the product to a 5-year-old. This is my favorite question whenever I want to understand something without the jargon & fancy English. “Explain it to me like I’m a 5-year-old” forces reps to simplify their pitch, making it more relatable and less jargon-heavy. Plus, imagining a sweet 5 year old with a candy in their mouth asking, “But but, what’s a CRM?” adds a touch of humor that can lighten the mood.

5. Encourage ‘Failure Fridays’

This one might sound counterintuitive, but hear me out. Failure is the best teacher—if you let it be. Start a “Failure Friday” tradition where your team shares stories & anecdotes from a deal they failed to close and why they think it happened. This normalizes failure, and it also turns it into a learning opportunity.
Remember, as Thomas Edison said, "I have not failed. I've just found 10,000 ways that won't work." Let's help our reps find their light bulb moment!
Bonus: the most epic fail of the month gets a prize. 

6. The "Kaizen" Approach

Borrowed from Japanese business philosophy, the Kaizen approach focuses on continuous, incremental improvement.

How to implement:

  1. Set small, achievable daily goals for each rep
  2. Celebrate minor victories regularly
  3. Encourage reps to suggest tiny tweaks to processes

It's like building a LEGO masterpiece – one brick at a time. Before you know it, you've got a sales team that's as solid as that masterpiece.

7. Break the Routine with Surprise Coaching Sessions

Routine can be the enemy of creativity. Instead of scheduling all coaching sessions, try springing a surprise coaching session, every now and then. Catch your reps off guard (in a good way) with a spontaneous session. The unpredictability keeps them on their toes and mimics real-life scenarios where they need to think on their feet. It breaks the monotony & the process of mugging a pitch. This could be the way to find insights & different perspectives on your product.

8. Incorporate Storytelling into Every Pitch

Humans are wired to respond to stories. Case studies are proven to be one of the most effective conversion methods in B2B marketing because they dive into details of how a product solved a problem, all while having a beautiful story intricately woven with facts & numbers. They make information more memorable and engaging. Encourage your reps to imbibe storytelling into their pitches—whether it’s a success story of how a client used your product or a personal anecdote that relates to the customer’s situation. Stories build rapport and make your pitch more compelling.

9. Leverage AI-Powered Feedback

Thanks to technology, ML and AI have elevated the work-life balance we aspire for. While AI in sales is still underexplored, I think it is safe to say the industry is picking up & delivering at an unfathomable pace. And no, I'm not just saying this because I work at Sybill (okay, maybe a little).

Ways to integrate AI:

  • Use AI-powered tools to analyze call recordings for coaching insights like tone, pace, storytelling, etc
  • Leverage predictive analytics to identify areas for improvement
  • Pick up & learn about potential clients’ non-verbal or emotional cues that could be missed while you are speaking or busy taking notes.

Remember, AI is here to augment, not replace. Think of it as your coaching sidekick, like Robin to your Batman. 

10. Coach to Personality Types, Not Just Skills

In sales coaching, you can’t take the approach of “One size fits all”. Every salesperson is different, with unique strengths and weaknesses. Tailor your coaching to fit their personality types. For example, an introverted rep might excel in written communication, while an extroverted one might thrive in face-to-face meetings. By understanding and leveraging their natural inclinations, you can coach them more effectively.

11. The "Gamification" Revolution

“All work and no play makes Jack a dull boy”. But what if you make work play? Gamifying your sales coaching can boost engagement and motivation.

Ideas to try:

  • Create a points system for different sales activities
  • Set up leaderboards for friendly competition
  • Offer rewards for reaching certain milestones - I’ve never heard a single person complain about extra money being credited to their accounts.

Just be prepared for the occasional "But I called dibs on that lead!" debates. What’s healthy competition without being at each other’s throats? It's all part of the game!

12. Celebrate the Small Wins

In the high-pressure world of sales, it’s easy to focus only on the big deals and forget the small victories. But those small wins—like getting a callback or successfully moving from one stage in the deal to another —are what build momentum. Make it a habit to celebrate these small wins during team meetings. Acknowledging these efforts boosts morale and encourages consistency.

Conclusion

There you have it, folks – 12 underrated sales coaching tips and tricks that can revolutionize your team's performance.
Sales coaching is as much an art as it is a science. While traditional methods are tried and true, incorporating these underrated tips and tricks can breathe new life into your coaching sessions. Remember, sales is about human connection, and the more personalized and empathetic your approach, the more successful your team will be.

And managers, don’t forget to have fun with it—because if you’re not enjoying the process, neither are your reps.

Ready to supercharge your sales coaching with AI-powered insights? Discover how Sybill.ai can help you fine-tune your approach and drive better results.

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