training – Page 2

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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Stop Guessing, Start Growing: How Strategic Sales Assessments Drive Real Revenue

By Sean O'Shaughnessey

You’ll eventually hit a wall if you’re running a sales organization—or wearing multiple hats as founder, CEO, and sales manager. That wall is often invisible until growth stalls, key deals slip through the cracks, or your top salesperson burns out. So, what’s the next move? It’s not more hustle. It’s assessment.

A sales assessment isn’t about checking boxes. It’s about understanding where you are, how you operate, and what’s holding you back. Too many small business leaders assume they’re doing fine because revenue is growing or the team is hitting their quotas. But are you growing at the rate your market allows? Are your sales activities aligned with your long-term goals? Are you building a repeatable system, or are you just getting lucky?

Let’s get tactical. A sales plan isn’t just a revenue target. It’s your go-to-market strategy. It defines your audience, your message, and your motion. It answers why you’re talking to those prospects and what value you’re bringing to them. Without a plan, you’re reacting instead of executing. You’re chasing leads instead of building a pipeline.

If you’re a small company—perhaps under $30 million in revenue—and selling into a national market, chances are your market potential is hundreds of millions, maybe billions. That means your market share is a rounding error, which means there’s room to grow. The question is: Are you operating in a way that allows you to capture that growth?

Even if you’re running lean, you should benchmark your performance against top-tier organizations. Not because you’re competing with them directly, but because they set the standard. What are they doing that you’re not? Where are they more efficient? How do they structure their teams? You’re leaving money on the table if you’re not asking those questions.

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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 – Engage, Listen, Succeed: Unlocking Client Conversations That Close Deals – E121

By Sean O'Shaughnessey

In this insightful episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey dive deep into the art of active listening and its transformative potential in sales. Building on the discussion from last week’s episode about discovery questions, Kevin and Sean provide actionable strategies to improve your listening skills, enhance your client interactions, and ultimately close more deals. Whether you’re a seasoned sales professional or new to the field, this episode is packed with valuable lessons you can apply immediately.

Key Topics Discussed

The Role of Active Listening in Sales Success
Kevin and Sean discuss how active listening differentiates successful salespeople from the rest and why it’s critical for uncovering client pain points.
The Power of Note-Taking
Kevin shares his transition from paper to digital note-taking and how capturing accurate information leads to better follow-ups and stronger client relationships.
Body Language and Visual Cues in Client Meetings
Sean emphasizes the importance of leaning forward, maintaining eye contact, and using other non-verbal cues to demonstrate engagement during conversations.
Learning from Reporters: Listening Like a Pro
Sean compares salespeople to seasoned reporters and outlines how active listening and asking thoughtful follow-up questions can set the stage for impactful discussions.
Upskilling Through Active Listening
Kevin highlights how organizations can improve their pipeline and closing rates by investing in training that focuses on active listening and effective questioning techniques.

Key Quotes

Sean O’Shaughnessey:
“Don’t ever book a meeting without educating the client or making them a better business. That’s the only reason you’re allowed in their office.” (Approx. 8:00)
Kevin Lawson:
“Active listening is your skeleton key to unlock doors that were previously closed. It’s the gateway to uncovering real pain points and creating meaningful solutions.” (Approx. 13:15)
Sean O’Shaughnessey:
“Leaning forward in your chair isn’t just about posture; it’s a powerful signal to your client that you’re fully engaged and ready to understand their needs.” (Approx. 10:00)

Additional Resources

Sean and Kevin refer to the previous episode on discovery questions as a foundation for this discussion. If you haven’t listened to it, consider downloading it for additional context.

A Significant Actionable Item from this Podcast

Apply Active Listening in Your Next Sales Call
In your next client interaction, focus on active listening by using these three steps:

Lean forward and maintain engaged body language.
Paraphrase the client’s statements to ensure understanding.
Take detailed notes and review them to tailor your follow-up responses.

These small adjustments can significantly affect the quality of your client conversations and help you close more deals.

Summary

Active listening isn’t just a soft skill; it’s a sales superpower. In this episode of Two Tall Guys Talking Sales, Kevin and Sean unravel the nuances of listening to clients, capturing their pain points, and building trust through meaningful interactions. With tips ranging from non-verbal cues to the tactical use of note-taking, this conversation equips you with tools to elevate your sales game. Whether you’re preparing for a discovery call, a QBR, or a cold call, this episode is a must-listen for actionable insights. Tune in and transform the way you engage with your clients.

Happy listening—and selling!

Two Tall Guys Talking Sales – The Motivation Formula: Achieving Big Wins in Sales – E116

By Sean O'Shaughnessey

In this compelling episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey dive deep into the heart of sales motivation and goal setting. They share relatable stories, actionable insights, and practical strategies for salespeople and sales leaders. Using a vivid sports analogy, Sean sets the tone for an episode packed with strategies to stay driven—even when the path isn’t clear. Whether you’re grappling with setting goals or maximizing your commission potential, this episode is a goldmine for actionable advice and personal growth.

Key Topics Discussed

The Athlete Analogy: Personal Motivation Meets Team Success (0:00)
Sean parallels a high school sprinter’s rigorous training and the dedication needed to succeed in sales.
The Importance of Personal “Why” in Sales Motivation (6:00)
Kevin and Sean explore how individual motivations—whether financial goals, family obligations, or personal growth—shape sales performance.
Breaking Down Your Sales Math to Achieve Success (10:00)
Kevin explains how to reverse-engineer your earnings goal, calculate deal requirements, and align your activities with desired outcomes.
Creating Personal Rewards for Milestone Achievements (9:00)
Sean shares a story about a salesperson’s unique approach to celebrating significant deals and how small rewards can drive consistent motivation.
The Art of Setting Goals When None Are Provided (3:30)
Kevin and Sean discuss practical steps for creating your own sales targets when your organization hasn’t assigned any.

Key Quotes

Sean O’Shaughnessey (2:00):
“What motivates you as a salesperson to do incredibly well? What are you doing to achieve your goals, and because you achieve your goals, maybe you’re inspiring someone else on your team to do the same.”
Kevin Lawson (4:29):
“If you’re not given a goal, do the math that gets you to success. It starts with understanding your economic driver and building a plan from there.”
Sean O’Shaughnessey (9:20):
“Choose something unique to reward yourself when something good happens. It’s a motivator for the day and can become the beginning of your career motivation.”

A Significant Actionable Item from this Podcast
Reverse-engineer your sales goals for 2024. Start by defining your desired income, break it down into weekly targets, and calculate how many deals you need to close. Then, analyze your closing rates to determine how many leads and opportunities you need to generate. Finally, track your progress weekly and adjust your strategy to stay on course.

Summary Paragraph
This episode of Two Tall Guys Talking Sales delivers powerful insights into staying motivated and setting actionable sales goals. Sean and Kevin expertly weave relatable analogies with proven strategies to help you master the art of self-motivation and goal achievement. Whether you’re working towards a personal milestone or aiming to inspire your team, this episode provides the tools to elevate your performance. Tune in and take control of your sales journey today!

Unlocking Sales Success: The Power of KPIs in Sales Processes

By Sean O'Shaughnessey

Are your sales KPIs helping your team succeed? Many sales leaders focus solely on closed deals. This narrow view misses crucial elements of sustainable sales growth.

The journey matters more than the destination. Sales excellence follows a similar path. Your team’s daily actions and behaviors create the foundation for lasting success.

Effective sales measurement requires a comprehensive view of your team’s activities. Top performers consistently execute vital behaviors that drive results. They prospect strategically, nurture relationships, and expand their presence within existing accounts. These leading indicators paint a clearer picture of future performance than lagging metrics alone.

Your KPI framework must evolve beyond historical analysis. Forward-looking metrics help you spot opportunities and challenges before they impact revenue. What’s happening in your pipeline right now? How are your teams finding new prospects? Which accounts show growth potential?

Experience levels significantly impact appropriate performance measures. New salespeople face different challenges than seasoned veterans. A rookie might need help with fundamental sales behaviors while learning your company’s approach. They need clear operational guidance and structured metrics that reinforce proper execution.

Veteran salespeople bring established skills and proven track records. Their KPIs should emphasize continuous improvement and cultural alignment. How are they advancing their capabilities? What value do they add to the broader sales organization?

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From Micro-Manager to Leader: Fostering Growth in Your Sales Team

By Sean O'Shaughnessey

Are you unknowingly sabotaging your sales team’s success? The answer might surprise you. The actual cost of micromanagement extends far beyond immediate productivity concerns.

Trust forms the bedrock of every high-performing sales organization. Yet many sales leaders unconsciously undermine this foundation through micromanagement. You’ve seen the signs – constant check-ins, questioning every decision, and hovering over your team’s shoulders. The culture you’ve worked so hard to build is slowly eroding.

Your best salespeople are leaving. Team morale is plummeting.

Let’s be clear about what constitutes micromanagement in sales. It’s not about being involved or interested in your team’s work. The real issue emerges when you start dictating every move and creating an atmosphere of constant surveillance.

Consider the cost of replacing top sales talent in today’s market. Beyond the substantial financial investment, you’re losing institutional knowledge and client relationships. Your organization can’t afford this drain on resources, and the impact reverberates throughout your entire sales ecosystem.

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