sales training

Sales Management with AI: Chat Interfaces vs. Automation Workflows

By Sean O'Shaughnessey

Sales organizations today face a critical decision: should they rely on interactive chat interfaces like ChatGPT, Claude, or Gemini, or should they focus on automation workflows? The answer isn’t either/or. Each approach has unique strengths, and choosing the right one directly impacts sales processes, productivity, and revenue generation.

The problem many sales teams encounter is “random implementation.” They hear about a new AI tool, adopt it quickly, and use it for the wrong purpose. The result? Chat interfaces get bogged down with repetitive work, and automation gets tasked with jobs that require creativity and nuance. Misuse not only reduces efficiency but also frustrates teams and erodes trust in artificial intelligence altogether.

So how do you know when chat is the right fit? The decision comes down to task complexity and uniqueness. Chat excels in situations that require creativity, flexibility, and human judgment. Four categories consistently stand out:

Creative and strategic tasks: proposals, executive messaging, strategic planning, and competitive positioning.
Complex problem-solving: sales opportunity strategy sessions, unique customer needs, and crisis management.
Learning and development: role-playing objection handling, skill coaching, and competitive intelligence training.
Research and analysis: prospect research, market analysis, and strategic planning.

Real-world examples show why this matters. Sales teams that use chat interfaces to refine proposals or craft custom strategies consistently achieve better win rates. Reps practicing objections with conversational AI ramp faster and perform better. Strategic analysis guided by chat tools generates insights that canned research often misses.

The key takeaway is straightforward: chat interfaces are most effective when tasks require human oversight, creativity, and iterative improvement. These are the high-value, low-frequency tasks where human expertise combined with AI delivers maximum impact. For repetitive, high-volume processes, automation is the right tool.

The future of B2B sales isn’t about choosing between humans and AI. It’s about humans amplified by AI. Let’s build that future together.

If you’d like to explore this topic in more depth, a podcast episode is available that covers all this information and more. You can find the link below and consider subscribing to the podcast AI Tools for Sales Pros on your favorite podcast player.

Mastering Sales Channels: How to Align Your Strategy for Maximum Impact

By Sean O'Shaughnessey

Understanding the dynamics of sales channels can transform how businesses approach their markets. Many sales professionals, whether they are salespeople, managers, or CEOs, often miss a critical distinction: the difference between the product they are selling and the value it provides.

This gap in understanding can lead to suboptimal sales performance, particularly in environments where products are sold through intermediaries, such as distributors, referral partners, or dealer networks. The challenge is not just about knowing your product, but also about understanding how to position it in a way that resonates with every player in the sales chain.

Sales success starts with recognizing who your true customer is. In sales management or channel sales, the end customer is often not the person you interact with directly. Instead, your “customer” might be the intermediary, your distributor, reseller, or even your own sales team. These intermediaries are the ones who ultimately connect your product to its final user. If you don’t understand their challenges, motivations, and context, you risk failing to equip them with the necessary tools to succeed. Are you selling a product’s features, or are you helping them understand how to sell it effectively? This distinction is vital.

When selling through intermediaries, the emphasis should shift from “what the product does” to “how the product can be sold.” Your distributors or referral partners don’t need every technical detail of your product. They need clarity on how it solves problems for their customers, how it fits into their existing offerings, and how they can position it to drive sales.

The goal is not to overwhelm your partners with information but to provide actionable insights that align with their specific needs. If you’re focusing solely on product features, you’re likely missing the mark.

Salespeople and sales managers must also recognize the game they are playing. Are you selling a commodity, a widely available product, or an exclusive offering? Each scenario demands a different strategy.

Commodities often compete on price, necessitating bulk sales or value-added services to differentiate themselves. Widely available products often rely on relationships, service quality, or unique add-ons to differentiate themselves. Exclusive products, on the other hand, can often avoid price wars by emphasizing their uniqueness and superior quality. Knowing which game you’re in allows you to tailor your approach and avoid misaligned strategies.

For small businesses and solopreneurs, the challenge lies in effectively managing referral partners. Referral partnerships are a powerful way to generate leads, but they require careful management and oversight.

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Beyond Quotas: Elevate Your Sales Strategy with Continuous Coaching

By Sean O'Shaughnessey

Salespeople often rely on short-term tactics to hit their numbers. But what if the difference between mediocrity and excellence isn’t in the last-minute push, but in the way we plan, coach, and lead throughout the year? Many sales managers treat coaching as a reactive measure, something they do when performance drops. That’s a missed opportunity.

Proactive coaching isn’t just about fixing issues. It’s about enhancing potential.

The best salespeople in the world, much like top athletes, have coaches. Not because they’re failing, but because they’re trying to be even better. If your top rep is hitting quota, that’s not the finish line. That’s the starting point for the next level of performance.

Sales leaders often default to focusing on the bottom performers. That’s necessary, but incomplete. High performers need guidance, too. Not to be micromanaged, but to be challenged. Ask yourself: What are you doing to help your top performers improve? If the answer is “not much,” you’re leaving growth on the table.

There’s a tactical way to approach this.

Most companies conduct quarterly business reviews with customers. The same structure can be flipped inward and used as a coaching tool. Instead of asking what happened last quarter, ask what could happen next. What would success look like in the next 90 days? What challenges need to be addressed before they become problems?

This isn’t about adding another meeting to everyone’s calendar. It’s about intentional planning. One-to-one conversations that go deeper than pipeline reviews. The goal is to align on strategy, identify gaps in skills or processes, and develop a roadmap for improvement. Done right, it drives accountability and engagement simultaneously.

Salespeople often say they want more training. But training without context falls flat. Coaching provides that context. It’s individualized, relevant, and ongoing. It also sends a message: your development matters. That message builds loyalty. It also improves performance.

If you’re a CEO or founder managing your own sales or leading a small team, this applies even more. You’re not just the closer, you’re the coach. Your team’s performance will reflect your commitment to their growth.

Are you investing time to help them get better?
Or are you too busy chasing deals to build a repeatable system?

Coaching doesn’t have to be complicated.

Begin by evaluating three key areas:

network,
skills,
metrics.

Does your rep have enough network reach to generate leads? Do they have the tactical skills to progress deals? And are you tracking the right metrics to measure performance, not just outcomes? If any of those are unclear, that’s your starting point.

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The Key to Profitable Sales Organizations: Understanding and Adhering to the Sales Process

By Sean O'Shaughnessey

Many salespeople, sales managers, and CEOs face a unique problem. This issue concerns the sales process, particularly when specific steps are skipped. The challenge is common among sales teams across various industries, and there are different perspectives on its causes and solutions.

This issue is concerning since, according to Harvard Business Review, 28% of companies that master at least three stages of their sales process will see an increase in revenue growth. (https://hbr.org/2015/01/companies-with-a-formal-sales-process-generate-more-revenue). That same study states that companies that had trained their sales managers to manage their pipelines saw their revenue grow 9% faster than those that didn’t. But not just any training will do. Sales managers need targeted training to address specific pipeline management challenges.

Sometimes, the sales process might seem tedious, and salespeople may skip steps out of impatience or eagerness to close a deal. However, skipping these steps can lead to further complications down the line. When a sales team is not following the process that has been identified, it can disrupt the team’s rhythm and efficiency. Some might argue that this is a sign that the process needs to change or that more training is required.

This issue extends beyond the sales team. When a company hires a fractional VP of sales, it brings an outside perspective to evaluate its sales process. The fractional VP will often encounter resistance from the existing team, who may feel their industry is unique. While every business has its distinctive elements, the fundamentals of a sales process are universal.

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Why Cold Calling is Dead: The Shift to Relationship-Based Selling

By Sean O'Shaughnessey

Building an effective sales pipeline requires a shift in strategy. Traditional cold calling has become increasingly ineffective, with decision-makers ignoring unsolicited calls and emails.

In the spring of 2021, Bank of America Corp.’s Merrill Lynch Wealth Management unit banned trainee brokers from making cold calls. According to the Wall Street Journal, it is hard to succeed with cold phone calls in an era when no one picks up. Merrill executives said personal referrals lead to a response around 40% of the time, but less than 2% of people who are cold-called even answer the phone.

Sales teams must adopt a more strategic approach, focusing on relationships rather than volume-based outreach. The key is leveraging existing networks to create warm introductions, significantly improving engagement rates and overall success.

Cold outreach has become expensive and inefficient, and the time spent dialing numbers, leaving voicemails, and sending emails that never get opened results in diminishing returns. Many executives no longer answer unknown calls, and email filters automatically sort cold outreach into spam. Even when messages get through, recipients are skeptical, assuming they are generated by automation rather than a genuine human connection. In reality, sales professionals must find a better way to reach their target audience.

Relationship-based selling offers a more effective alternative. Salespeople should focus on leveraging their connections instead of reaching out to strangers. This approach involves identifying key contacts who can provide warm introductions to potential prospects. These “super connectors” are individuals with strong networks and the ability to facilitate meaningful introductions. By tapping into these relationships, sales teams can bypass the skepticism associated with cold outreach and start conversations with credibility.

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Two Tall Guys Talking Sales – From Regular Season to Postseason: Coaching Your Sales Team to Win – E128

By Sean O'Shaughnessey

As a sales leader, are you coaching your team for the long haul, or are you scrambling in the final weeks of the quarter? In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey break down the difference between regular season and postseason play—whether in sports or sales. They explore why last-minute Hail Mary strategies can be damaging, how to manage time, and the importance of effective and consistent coaching. With March Madness and The Masters as the backdrop, this conversation is packed with insights to help you refine your sales approach and ensure your team is always in winning form.

Key Topics Discussed

The Sales Tournament Mentality (00:02:00) – What sales teams can learn from March Madness and The Masters, and why only one team wins while the rest lose.
Building a Winning Sales Team (00:03:30) – How business owners can prepare their sales teams to perform under pressure by ensuring the right people are in the right seats.
The Role of Sales Coaching (00:05:00) – Why sales leaders must incorporate skills development into every sales meeting instead of just reviewing the pipeline.
The Pitfalls of End-of-Quarter Desperation (00:07:50) – How last-minute discounting and rushed deals create long-term problems and train customers to buy at a discount.
Mastering Time Management in Sales (00:10:00) – How prioritization and disciplined execution throughout the quarter prevent last-minute chaos and boost consistent performance.

Key Quotes

Kevin Lawson (00:07:53): “If you’re behind in sales right now, don’t throw Hail Marys. Don’t discount. You’re teaching your prospects to wait until the end of the quarter for a better deal—and that’s a losing game.”
Sean O’Shaughnessey (00:13:00): “You have one thing in sales you can never get back: time. If you wasted today, it’s gone forever. You can’t go back and fix it.”
Kevin Lawson (00:09:00): “Salespeople with commission breath stink. If your only focus is closing the deal before Friday, your prospects will smell it a mile away—and that’s not how you build relationships.”

A Significant Actionable Item from this Podcast

Develop a Five-Week Sales Training Plan – Sales leaders should map out the next five sales meetings, dedicating at least five minutes to skills development in each session. Focus on topics such as pipeline progression, prospect qualification, and closing techniques. Training should not be an afterthought—it should be a fundamental part of your sales strategy.

Why You Should Listen to This Episode

Whether you’re a sales leader or a frontline salesperson, this episode is your playbook for maintaining momentum all year long. Avoid the common traps of end-of-quarter desperation, build a disciplined approach to sales training, and master the art of time management. Just like in sports, sales success isn’t about last-minute heroics—it’s about consistent execution.

Tune in now and take your sales game to the next level!

Two Tall Guys Talking Sales Podcast – Sales Strategy Deep Dive: How to Align Offers with Client Expectations – E102

By Sean O'Shaughnessey

Join hosts Kevin Lawson and Sean O’Shaughnessey in a dynamic episode of “Two Tall Guys Talking Sales,” where they dive deep into the essential elements of crafting an effective sales strategy. Whether you’re a sales newbie or a seasoned pro, this episode promises insights into refining your approach to acquiring new clients and boosting your sales performance.

Key Topics Discussed:

Ideal Client Profiles (Approx. 00:01:00): Discover the power of tailoring your approach to fit the perfect client profile and why it’s the cornerstone of any successful sales strategy.
Messaging in Sales (Approx. 00:03:27): Learn the art of crafting messages that resonate with your target audience, ensuring your communication aligns perfectly with their expectations and needs.
Designing Compelling Offers (Approx. 00:06:31): Explore how to frame your products or services in a way that emphasizes their value and addresses the aspirational needs of your clients.
Strategic Alignment (Approx. 00:12:11): Understand the synergy between client profiles, messaging, and offers and how aligning these elements can lead to sales success.
Sales Process Optimization (Approx. 00:10:59): Gain insights into organizing your sales strategies to ensure they are effective, repeatable, and scalable.

Key Quotes:

Kevin: “If you’re a dentist and all you get is people with foot pain, you’re sending out the wrong message about your practice.” (Approx. 00:03:52)
Sean: “The goal for really selling and eliminating your competition and really setting yourself up for success is to teach them to aspire to something greater.” (Approx. 00:09:04)

Additional Resources:

“Strategic Selling” by Miller Heiman – A seminal book on sales strategies, mentioned for its impactful concepts that have shaped modern sales approaches. – https://a.co/d/iPykhyA
RAIN Group Sales Training – Recommended for those looking to further their understanding of sales aspirations and strategic customer alignment.

A Significant Actionable Item from this Podcast:

Reflect on Your Client Profiles: Take a moment to revisit and refine your ideal client profiles. This exercise will help ensure that your sales messaging and offers are perfectly tailored to meet your target audience’s specific needs and aspirations, significantly increasing your chances of closing more deals.

Summary:

In this episode, Kevin and Sean break down the intricate dance of aligning client profiles, messaging, and offers to craft a sales strategy that meets and exceeds expectations. Their conversation is filled with actionable advice backed by real-world examples and seasoned insights, making it a must-listen for anyone looking to enhance their sales effectiveness. Tune in to refine your approach and learn how to construct sales pitches that are heard and truly resonate.

Two Tall Guys Talking Sales Podcast – Beyond the Basics: Elevating Sales Training with Effective Coaching – E101

By Sean O'Shaughnessey

In this riveting episode of “Two Tall Guys Talking Sales,” hosts Kevin Lawson and Sean O’Shaughnessey explore the often overlooked nuances of effective sales training and coaching. Listen in as they share their seasoned insights on transforming routine sales training into a dynamic tool for substantial growth and success in sales.

Key Topics Discussed:

The Misconception of Sales Training Returns [00:00:20] Sean questions salespeople’s low expectations regarding training, sparking a discussion on the intrinsic value of continuous professional development.
The Role of Sales Leaders in Training [00:01:00] Kevin emphasizes the critical role of sales leaders in setting the right expectations and fostering an environment conducive to growth, drawing parallels with professional sports training regimes.
Training vs. Coaching [00:07:05] The conversation pivots to the essential distinction between sales training and coaching, highlighting how each plays a unique role in a salesperson’s career.
Integration of Training into Routine [00:06:22] Kevin discusses the challenges of integrating training into the normal workflow of sales teams and the importance of practice and repetition.
The Power of Reinforcement [00:04:05] Sean underscores the necessity of reinforcing training through regular coaching, using the analogy of professional athletes to illustrate his point.

Key Quotes:

Kevin: “We practice every day for the championship game. We don’t play the championship game every day. It’s about getting that 1 percent edge.” [00:01:14]
Sean: “You forget 80 percent of what you heard after two weeks. It’s the coaching after the fact that reinforces the entire attitude and the daily behavior of what you learned in the class.” [00:03:40]

Additional Resources:

MEDDPICCC Sales Methodology – Mentioned multiple times throughout the podcast, this methodology is crucial for understanding customer dynamics and improving sales strategies. You can learn more about MEDDPICCC at https://youtu.be/RBcGmyeBp1I?si=No_0Ob1V4Wch6erI

Summary:

Join Kevin and Sean as they dissect the common pitfalls of sales training and explore effective strategies to make learning stick. They share invaluable advice on how sales leaders can profoundly influence their teams’ performance through intentional coaching and robust training frameworks. This episode is a must-listen for sales professionals eager to elevate their game and harness the full potential of their training experiences.

A Significant Actionable Item from this Podcast:

Reflect on your current approach to sales training and coaching. Are you actively ensuring that your team learns new concepts and applies them consistently? Consider adopting a more structured follow-up coaching plan to reinforce new skills and knowledge, enhancing the overall effectiveness of training sessions.

To understand if your company is doing a great job in sales, take this quick and easy 10-question assessment:
https://salesxceleration.com/sales-agility-assessment/?locationid=26671639

Building a Successful Sales Team: A Guide for CEOs and Managers

By Sean O'Shaughnessey

You can overcome obstacles and significantly improve your sales performance with the right mindset, strategies, and tools. For salespeople, sales managers, and CEOs of small companies, the journey to sales excellence is paved with lessons and insights that can be invaluable in improving management capabilities and driving revenue growth.

The sales process is a critical aspect of any business. It’s the engine that drives revenue and growth and the platform on which customer relationships are built. However, businesses often encounter a unique problem in their sales process. The problem isn’t necessarily about the product or service being sold, the market, or the competition. Rather, it’s about the people involved in the process—the salespeople.

Being a salesperson is a challenging profession. It requires a unique set of skills, a deep understanding of the product or service being sold, and a certain level of resilience to face the inevitable rejections that come with the job. But more than that, it requires a mindset that embraces growth, learning, and continuous improvement.

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Two Tall Guys Talking Sales Podcast – Selling the Hole, Not the Drill: Understanding the Real Value Behind Your Sales – E91

By Sean O'Shaughnessey

Welcome to another insightful episode of “Two Tall Guys Talking Sales,” where our hosts Kevin Lawson and Sean O’Shaughnessey dive deep into the complexities and strategies of sales. In this episode, they explore the nuanced dynamics of selling through distribution and understanding the real needs of your customers. Whether you’re a seasoned sales veteran or just starting in your career, this episode offers a wealth of knowledge on refining your sales approach to maximize effectiveness and customer satisfaction.

Key Topics Discussed:

Selling Through Distribution: Sean shares his early career mistakes and the pivotal lessons of focusing beyond just the product features.
Understanding Your Customer’s Needs: Strategies to grasp what the end-user truly requires from a product, rather than just its specifications.
The Importance of Simplicity in Sales: Kevin emphasizes how simplifying your sales message can vastly improve understanding and efficiency in sales processes.
Sales Training and Knowledge Transfer: Both hosts discuss how proper training and knowledge sharing with channel partners and sales teams can lead to better sales outcomes.
The Role of Value in Sales: How to communicate the unique value of a product or service to stand out in a competitive market.
Referral Partnerships and Networks: Sean elaborates on the significance of nurturing relationships with referral partners to enhance lead generation for smaller businesses.

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