3 biggest mistakes I’ve seen after 291 one-on-one sales coaching sessions | Ep 61

Assess Yourself or your sales team vs Top Performers Here for FREE! or  Free Sales Preparation Course to help you outperform the competition in 19 minutes. After delivering 291 one-on-one sales coaching sessions in just six months, Paul M. Caffrey has seen the same three mistakes holding salespeople back again and again. In this episode, Paul breaks down each mistake, why it matters, and the exact steps to fix it — so you can improve your forecasting, increase your close rate, and sell with more confidence. Whether you’re an Account Executive, a Sales Leader, or preparing for your next SKO, these three fixes will help you move deals faster and close more business.   Timestamps 00:00 – Intro: 291 coaching sessions in six months 00:18 – Podcast credits 00:33 – Why you’re losing deals (and it’s not what you think) 01:15 – About Paul M. Caffrey and The Work Before the Work 02:05 – Mistake #1: Skipping Mutual Success Plans 03:20 – How to make Mutual Success Plans a habit 04:02 – Mistake #2: Not Confirming the Agenda 05:05 – How to make agenda confirmation a habit 05:40 – Mistake #3: Avoiding Video Prospecting 06:42 – How to make video prospecting a habit 07:30 – Closing thoughts: Fix one, fix all three

Assess Yourself or your sales team vs Top Performers Here for FREE! or  Free Sales Preparation Course to help you outperform the competition in 19 minutes. All salespeople send emails. Some send videos. But top performers? They send video at six key moments in their sales process—and it’s changing the game. In this episode, Paul breaks down what he learned from Shari Levitin (one of the world’s leading sales trainers) about how elite sellers are using video to build trust, increase open rates, and close more deals—without needing a big following or fancy tech. You’ll learn: Why video builds trust faster than text The 6 best points to send sales videos (with examples) How to structure short, powerful messages that get results If you’re in B2B and want to cut through the noise—this is your playbook.

Connect with Datarails CRO Aviv Canaani on LinkedIn THE PREPARED SELLING COURSE | A free 29-minute course that shows Account Executives how top performers prepare for demos, discovery, and referrals — and win more deals, faster. GET FREE ACCESS The Elite Sales Professional Assessment: Answer 15 Questions to Benchmark your ability to sell vs elite sales professionals. GET YOUR SALES BENCHMARK HERE Summary In this conversation, Aviv Canaani, the CRO of DataRails, shares insights on building a successful go-to-market strategy focused on driving inbound leads, optimizing sales processes, and fostering a high-performing sales team. He emphasizes the importance of metrics, conversion rates, and a structured sales methodology to ensure predictable revenue. Aviv also discusses the significance of team motivation, effective hiring practices, and the role of preparation in achieving sales success. Takeaways Creating a go-to-market machine is essential for driving inbound leads. Metrics like meeting to close one are crucial for evaluating sales performance. A structured sales methodology helps in scaling the sales process effectively. Speed to lead is critical in converting prospects into customers. Trust and collaboration within the sales team enhance overall performance. Promoting from within and recognizing top performers fosters a motivated sales team. Evaluating sales talent through simulations can reveal true capabilities. Forecasting sales requires a mix of historical data and current pipeline insights. Preparation for sales calls is vital for success and should be prioritized. CROs must focus on building a predictable revenue model to satisfy stakeholders.    

"Don't be afraid to give out your knowledge, to share your knowledge freely." Perry van Beek (Connect on LinkedIn) Want to prepare your sales team to become top performers in 2025? Event Organisers: Paul M. Caffrey | Sales Keynote Speaker:  Check Paul's availability to speak at your event. Founder Sellers: Prepared Selling OS for AI Founders: Learn how to build your first sales team here.  Ambitious Account Executives: Coaching with Paul FULL: Join Waitlist  Get the Book: "The Work before the Work, The Hidden Habits Elite Sales Professionals Use to Outperform the Competition" here or listen free on Spotify premium Connect with Paul M. Caffrey on LinkedIn. Episode Overview:In this episode, Paul M. Caffrey sits down with Perry Van Beek – best-selling author of LinkedIn Sales Navigator for Dummies, with 30 years of sales expertise and over 150 LinkedIn recommendations. Perry dives into his top tips for prospecting, sales, and using LinkedIn Sales Navigator to transform your approach. Learn how helping people, going the extra mile, and setting healthy boundaries can turn prospects into long-term clients. Key Discussion Points: Prospecting Through Value:Perry explains how shifting from sending generic pitches to offering free advice on LinkedIn helped him secure his first clients. His approach is simple – share your knowledge freely and help potential customers before asking for business. Sales Strategy – The Extra Mile:Discover why Perry believes that going that extra mile not only deepens client relationships but often eliminates the need for traditional prospecting. As he puts it, “You will never ever have to prospect again” when you consistently add value. Promotion & Boundaries:Learn the importance of saying “no” and setting boundaries. Perry shares how learning to prioritize and even decline certain tasks can be key to avoiding burnout and even earning a promotion. Recommended Reading for Sales Success:Perry cites the inspiration behind his journey – including Screw It, Let's Do It by Richard Branson and The One Thing by Greg McKeown – as essential reads for anyone looking to elevate their sales game. Optimizing Your LinkedIn Presence:From refining your LinkedIn profile to clearly defining your ideal client profile, Perry underscores why a customer-centric approach is critical for leveraging Sales Navigator effectively. Connecting with Perry:Find Perry on LinkedIn (linkedin.com/in/perryvanbeek) and take advantage of his free 10-minute consultation call to fine-tune your Sales Navigator strategy. Episode Chapters & Timestamps: 00:00 – Introduction & Perry’s Sales JourneyMeet Perry Van Beek and learn about his extensive sales background. 02:40 – Going the Extra MilePerry reveals how contributing to the buying journey can transform your prospecting efforts. 04:33 – The Power of Saying “No”Discover why setting boundaries is crucial for success and sustainable growth. 06:38 – Must-Read Sales BooksPerry discusses the inspirational books that influenced his career. 09:22 – Crafting a Customer-Centric LinkedIn ProfileTips on making your profile resonate with potential clients. 09:31 – Mastering Sales NavigatorPractical strategies to leverage this essential tool for better sales outcomes. 13:04 – How to Connect & Get StartedLearn how to book a free consultation with Perry and access his wealth of free resources. Call-to-Action: Connect with Perry: Visit his LinkedIn profile at linkedin.com/in/perryvanbeek. Book a Free Consultation: Check the top link in the show notes to schedule your 10-minute call and kickstart your Sales Navigator strategy. Subscribe & Share: Don’t miss out on more actionable sales tips—subscribe and share this episode with your network.

"Sell to people who want your product, not who need your product." Pointer Founder Ricky Pearl Prepare yourself & your sales team to become top sales performers in 2025. Event Organisers: Paul M. Caffrey | Sales Keynote Speaker:  Check Paul's availability to speak at your event. Ambitious Account Executives: Coaching with Paul: Apply Here Founder Sellers: Prepared Selling OS for AI Founders: Learn how to build your first sales team here.  Get the Book: "The Work before the Work, The Hidden Habits Elite Sales Professionals Use to Outperform the Competition" here or listen free on Spotify premium Connect with Paul M. Caffrey on LinkedIn. Connect with Ricky Pearl on LinkedIn or check out his company POINTER here.   Summary In this conversation, Ricky Pearl shares his top sales tips and insights. The main themes include prospecting, selling to people who want your product, getting promoted, recommended books, and preparation. Ricky emphasizes the importance of consistency in prospecting and having conversations with potential buyers. He also highlights the value of selling to people who genuinely want your product, rather than those who simply need it. To get promoted, Ricky advises focusing on professional development and understanding your manager's job. He recommends books that promote introspection and understanding human nature. In terms of preparation, Ricky suggests knowing what the prospect expects you to know without over-preparing. Takeaways Consistency is key in prospecting and having conversations with potential buyers. Sell to people who genuinely want your product, not just those who need it. Focus on professional development and understand your manager's job to get promoted. Recommended books for sales include those that promote introspection and understanding human nature. Preparation should involve knowing what the prospect expects you to know without over-preparing.

"Become a millionaire using my simple tracking template" Sjoerd Bak | GET YOUR FREE TRACKER HERE ____ Prepare yourself & your sales team to become top sales performers in 2025. Event Organisers: Paul M. Caffrey | Sales Keynote Speaker:  Check Paul's availability to speak at your event. Sales Leaders: Sales Preparation Masterclasses: Book LIVE! Virtual Sales Team Masterclass Here.  Ambitious Account Executives: Custom Sales Coaching: Book a 1:1 Strategy session here.  Founder Sellers: Prepared Selling OS for AI Founders: Learn how to build your first sales team here.  Get the Book: "The Work before the Work, The Hidden Habits Elite Sales Professionals Use to Outperform the Competition" here or listen free on Spotify premium Connect with Paul M. Caffrey on LinkedIn.  ____ Connect with Sjoerd BAMILLIONAIRE.COM on LinkedIn Summary In this episode of the podcast, Paul M. Caffrey interviews Sjoerd Bak, founder of Become a Millionaire, discussing the importance of financial independence and effective money management. Sjoerd shares his journey from spending all his earnings to becoming a qualified financial advisor, emphasizing the significance of understanding pensions, investment strategies, and the risks associated with employee stock purchase plans and cryptocurrencies. He also highlights the importance of teaching financial literacy to children, ensuring they are equipped with the knowledge to manage their finances effectively in the future. Takeaways Money management is crucial for financial independence. Tracking expenses is the first step to financial awareness. Pensions are often overlooked but are vital for wealth building. Maximizing pension contributions can lead to significant tax benefits. Investing should be prioritized over lifestyle spending. Diversification is key to managing investment risk. Cryptocurrency can be a gamble; approach with caution. Teaching children about money early can set them up for success. Understanding the fees associated with investments is essential. Salespeople often have great benefits that should be leveraged.    

"The best salespeople are the ones that know why they do it. If you know what you're earning all that money for, then it becomes easier to stick with the prospecting." Sjoerd Bak - Connect on LinkedIn HERE ____ Prepare yourself & your sales team to become top sales performers in 2025. Event Organisers: Paul M. Caffrey | Sales Keynote Speaker:  Check Paul's availability to speak at your event. Sales Leaders: Sales Preparation Masterclasses: Book LIVE! Virtual Sales Team Masterclass Here.  Ambitious Account Executives: Custom Sales Coaching: Book a 1:1 Strategy session here.  Founder Sellers: Prepared Selling OS for AI Founders: Learn how to build your first sales team here.  Get the Book: "The Work before the Work, The Hidden Habits Elite Sales Professionals Use to Outperform the Competition" here or listen free on Spotify premium Connect with Paul M. Caffrey on LinkedIn.  ____ Connect with Sjoerd BAMILLIONAIRE.COM on LinkedIn Summary In this engaging conversation, Sjoerd Bak shares his insights on sales, emphasizing the importance of consistency, understanding customer pain points, and continuous personal development. He encourages treating one's job as a college for ongoing learning and stresses the significance of preparation for successful interactions. Sjoerd also recommends impactful books that can enhance sales skills and personal growth. Takeaways Be consistent in your prospecting efforts to achieve success. Sales is about understanding and addressing customer pain points. Treat your job as a college for continuous learning. Reading books is essential for personal and professional development. Understanding the purpose of your earnings can motivate you in sales. Preparation is key for every interaction in sales. If an interaction doesn't require preparation, reconsider its importance. Top performers are always learning and improving their skills. The best salespeople are those who know why they do what they do. Investing in your education can lead to amazing career advancements.    

"Make as much money as quick as possible." Will Barron - Connect on LinkedIn HERE ____ Prepare yourself & your sales team to become top sales performers in 2025. Event Organisers: Paul M. Caffrey | Sales Keynote Speaker:  Check Paul's availability to speak at your event. Sales Leaders: Sales Preparation Masterclasses: Book LIVE! Virtual Sales Team Masterclass Here.  Ambitious Account Executives: Custom Sales Coaching: Book a 1:1 Strategy session here.  Founder Sellers: Prepared Selling OS for AI Founders: Learn how to build your first sales team here.  Get the Book: "The Work before the Work, The Hidden Habits Elite Sales Professionals Use to Outperform the Competition" here or listen free on Spotify premium Connect with Paul M. Caffrey on LinkedIn.  ____ Connect with Will Salesman.com website here on LinkedIn Summary This conversation explores the journey towards financial success, emphasizing the importance of strategic planning, mindset, and learning from successful entrepreneurs. It discusses various strategies for quick wealth accumulation and the challenges of navigating career transitions. Takeaways The goal is to make as much money as quickly as possible. Career transitions require careful planning and strategy. Mindset plays a crucial role in building wealth. Learning from successful entrepreneurs can provide valuable insights. Wealth accumulation is a journey that requires patience. Quick wealth strategies can be effective if executed properly. Understanding the competitive nature of financial success is essential. Adapting to change is key in career transitions. Financial success often involves taking calculated risks. The importance of networking and building relationships in business.    

"Listening is more important than talking." A.J. Mahar - Connect on LinkedIn HERE ____ Prepare yourself & your sales team to become top sales performers in 2025. Event Organisers: Paul M. Caffrey | Sales Keynote Speaker:  Check Paul's availability to speak at your event. Sales Leaders: Sales Preparation Masterclasses: Book LIVE! Virtual Sales Team Masterclass Here.  Ambitious Account Executives: Custom Sales Coaching: Book a 1:1 Strategy session here.  Founder Sellers: Prepared Selling OS for AI Founders: Learn how to build your first sales team here.  Get the Book: "The Work before the Work, The Hidden Habits Elite Sales Professionals Use to Outperform the Competition" here or listen free on Spotify premium Connect with Paul M. Caffrey on LinkedIn.  ____ Connect with A.J.  Sellfire website here on LinkedIn Summary This conversation delves into the importance of objection elimination in sales, exploring various strategies for effective communication, building trust, and overcoming common objections. The role of empathy in sales is emphasized, highlighting how understanding clients' needs can lead to better outcomes. The discussion concludes with key takeaways that encapsulate the essence of successful sales techniques. Takeaways Objection elimination is one of the biggest things that I like to focus on. Effective communication can change the game in sales. Building trust is essential in sales relationships. Empathy plays a crucial role in overcoming objections. Understanding your client's needs is key to success. Listening is more important than talking in sales. Every objection is an opportunity to learn and improve. Sales is about relationships, not just transactions. The best salespeople are great listeners and communicators. Trust takes time to build but can be lost quickly.    

"Check your assumptions and test." Gary Fox. The Entrepreneur Experiment Podcast here ____ Prepare yourself & your sales team to become top sales performers in 2025. Event Organisers: Paul M. Caffrey | Sales Keynote Speaker:  Check Paul's availability to speak at your event. Sales Leaders: Sales Preparation Masterclasses: Book LIVE! Virtual Sales Team Masterclass Here.  Ambitious Account Executives: Custom Sales Coaching: Book a 1:1 Strategy session here.  Founder Sellers: Prepared Selling OS for AI Founders: Learn how to build your first sales team here.  Get the Book: "The Work before the Work, The Hidden Habits Elite Sales Professionals Use to Outperform the Competition" here or listen free on Spotify premium Connect with Paul M. Caffrey on LinkedIn.  ____ Connect with Gary Fox gary fox website here The Entrepreneur Experiment Podcast here Gary Fox on LinkedIn Summary In this conversation, the speaker emphasizes the critical role of checking assumptions in prospecting, sharing effective strategies for building relationships with prospects, leveraging technology, and measuring success. The discussion highlights the importance of adaptability and continuous learning in the sales process. Takeaways Check your assumptions and test before starting. Effective prospecting is about building relationships. Leverage technology to streamline your process. Measure your success to improve your strategy. Always be open to learning and adapting. Networking is key in sales. Follow up is crucial in prospecting. Understand your target audience deeply. Use data to inform your decisions. Stay persistent and resilient in your efforts.