sales management

Navigating the Sales Maze: Overcoming Missed Steps in Your Sales Process

By Sean O'Shaughnessey

The challenges for a salesperson or a sales manager are numerous. One such challenge that often arises during the sales process is the realization that a crucial step has been skipped. This situation is not uncommon and is faced by many salespeople. However, it’s not a moment for reprimanding or pulling out an accountability chart. Instead, it’s a moment of realization and an opportunity to rectify the error to avoid ending up in the ‘no decision lane.’

I have written about the importance of skipping stages of the sales process elsewhere on this site, most recently in “The Key to Profitable Sales Organizations: Understanding and Adhering to the Sales Process,” where I remind you that, according to the Harvard Business Review, 28% of companies that master at least three stages of their sales process will see an increase in revenue growth.

When you recognize you’ve missed a step in your sales process, it resembles backing up a train. You’ve got a lot of cars put together, but one is out on its own. Addressing this situation requires a specific style and approach. As a sales leader, your focus should be on the next step in the process. Have you covered this step from a question in the sales meeting? It’s important to ask questions like, “What is next? What is missing? What is now?”

As a salesperson, if you realize you’ve missed a step, address it head-on. This approach allows you to rectify your error and builds trust with your prospect by demonstrating transparency and accountability.

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Validation Events: The Unsung Hero of Sales Process Discipline

By Sean O'Shaughnessey

In the complex world of B2B selling, trust is built in stages. The challenge in all sales campaigns is ensuring the prospect trusts they are making the best decision for their business.

Do they trust that the salesperson is giving them all of the information?
Do they trust that the company will support them after the sale?
Do they trust that the product will perform as they expect it to perform?

As I have explained in my book, Eliminate Your Competition, as well as the blog for that book and in this blog, the prospect needs to trust all three elements the salesperson is selling:

They need to trust the product.
They need to trust the company behind the product.
They need to trust the salesperson.

Prospects listen to your sales message, review your materials, and hear your claims, but none of that guarantees belief or trust. Trust is validated when your claims are validated. That’s why validation events are crucial to any rigorous sales process.

In The Qualified Sales Leader, John McMahon stresses the importance of customer-driven validation. He cautions sales leaders against relying on internal optimism or anecdotal “good signals” from prospects. Instead, McMahon emphasizes observable proof—real buyer behavior that confirms alignment, commitment, and value. Validation events are when the customer takes action to validate that what you’ve promised is accurate and valuable.

An excellent sample sale process flow looks like this:

Discover
Scoping
Economic Buyer Meeting
Validation Event
Business Case and Final Proposal
Negotiate and Close

As you can see, the Validation Event is the last step before creating the final business case, which will be bundled with your final proposal.

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Level Up Your Sales Prospecting with Advanced Research Techniques

By Sean O'Shaughnessey

A shoutout to Chris Spanier and Episode #85 of the Practical, Actionable Marketing Podcast

Sales prospecting has always been a grind. What if you could cut your research time in half and dramatically improve your outreach results?

In Episode #85 of the Practical, Actionable Marketing podcast, host Chris Spanier delivers a masterclass on how to do just that. Titled “Advanced Prospecting Research Tools,” the episode is packed with time-saving techniques and tools that help sales professionals build sharper prospect profiles faster.

As someone with over four decades in sales and sales management, I believe this kind of tactical insight makes a difference. If you haven’t already, listen to the episode. Then, come back here for a quick breakdown of what Chris covered—plus a few of my thoughts.

Why Prospect Research Matters More Than Ever

In a market saturated with sales messages, relevance is your only competitive advantage. The days of blasting generic emails to massive lists are over. Today, the winners are the ones who personalize their outreach with precision—and that begins with better research.

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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 – Mastering Time Management: Essential Strategies for Sales Managers – E123

By Sean O'Shaughnessey

Time is the most valuable resource for any professional, but for sales managers, it is the linchpin of success. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey dive into the critical strategies for effective time management as a sales leader. Whether you’re a new sales manager, an aspiring leader, or a business owner overseeing a sales team, this discussion is packed with insights to help you optimize your calendar, empower your team, and drive performance without falling into the trap of micromanagement.

Key Topics Discussed

The Shift from Salesperson to Sales Manager (00:03:00)
Understanding the common pitfalls new sales managers face when transitioning from an individual contributor to a leadership role.
The Role of a Sales Manager: Player vs. Coach (00:04:00)
Why sales managers must avoid the “player-coach” mindset and instead focus on leading, mentoring, and enabling their team’s success.
Structuring Your Calendar for Maximum Impact (00:05:45)
How to design your weekly schedule to balance coaching, strategy, internal meetings, and team availability while avoiding distractions.
The Power of Shared Calendars and CRMs (00:07:00)
Best practices for leveraging shared calendars and CRM tools to improve communication, transparency, and sales efficiency.
Why Sales Managers Should Be Like Basketball Coaches (00:13:30)
The importance of stepping back and allowing sales reps to take the lead in deals—coaching them rather than closing for them.

Key Quotes

🗣 Sean O’Shaughnessey (00:02:55):
“When you are a sales manager, your job is to make others better. You shouldn’t be stealing deals from your sales reps—you should be empowering them to succeed.”

🗣 Kevin Lawson (00:04:00):
“A player is different from being a coach. Players take direction, coaches give direction. If you’re leading a team, you need to be coaching, not competing.”

🗣 Sean O’Shaughnessey (00:14:00):
“Watch a basketball game and look at the coach. How many times do they step onto the court to take a free throw for their players? Never. That’s how sales management should work too.”

Additional Resources

📘 The One Minute Manager by Ken Blanchard & Spencer Johnson – A classic guide to leadership and effective management.
📅 Book Time with Sean – Need help refining your sales management strategy? Schedule a consultation.

A Significant Actionable Item from this Podcast

Audit Your Calendar and Block Time for Success
Sales managers must structure their schedules intentionally. Take 30 minutes to review your calendar for the upcoming week:
✅ Block out time for coaching your team.
✅ Set aside dedicated slots for strategy and internal meetings.
✅ Ensure your calendar is updated and visible for your team.
✅ Reserve time for proactive sales engagement, like voice-of-the-customer calls.

Making these adjustments will free you from constant firefighting and allow you to lead effectively.

Why You Should Listen to This Episode

If you’re a sales manager—or aspiring to be one—this episode is a must-listen. Kevin and Sean deliver practical, real-world strategies to help you break free from micromanagement, structure your time effectively, and lead your team to success. Stop getting caught up in the weeds and start managing like a pro. Listen now and take control of your sales leadership journey!

🎧 Hit play and start optimizing your sales management strategy today! 🚀

Understanding Your Customers: The Role of Buyer Personas and Quarterly Business Reviews

By Sean O'Shaughnessey

Want to know the real secret behind successful sales? It’s not just about knowing what your customers need. The true power lies in understanding who they are at their core.

Have you ever wondered why some sales professionals consistently outperform their peers? The answer often comes down to their mastery of buyer personas and detailed profiles that capture the essence of your ideal customers.

Think of buyer personas as your secret weapon in the sales battlefield. These aren’t just random customer profiles thrown together in a rushed afternoon meeting. They represent carefully crafted composites of your most valuable clients, built from real-world data and insights. Your company might need several of these personas, each targeting different market segments with laser precision.

Creating effective buyer personas demands more than just surface-level observation. Start with a thorough analysis of your business landscape. Examine your strengths and weaknesses. Map out the opportunities that excite you and the threats that keep you up at night. This foundation helps you understand exactly where you fit in your customers’ world.

What makes your top customers tick? The answer lies in meaningful conversations with your best clients. These discussions should dig deep into both quantitative and qualitative factors. Demographics tell part of the story – age, position, education, family status. But the real gold comes from understanding their motivations. Why did they choose you? What problems do you solve that keep them coming back?

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Selling Trust: The New Era of Salesmanship in the Digital Age

By Sean O'Shaughnessey

Have you ever wondered why some salespeople consistently outperform their peers? The answer might surprise you – it’s not about pushing products anymore. Let me share a story that perfectly illustrates this point.

Picture yourself at a car dealership with a problematic engine. The service manager listens briefly and suggests trying premium fuel first instead of pushing for expensive repairs. This unexpected advice reveals the essence of modern sales: building trust over making quick profits.

The digital revolution has transformed how we sell. Your prospects now have instant access to product information, specifications, and reviews. They’ve often completed 70% of their buying journey before contacting you. So, what’s your role in this new landscape?

You must evolve from an information provider to a value creator. Think about it – when did a customer last ask you for basic product details? They don’t need that anymore. They need someone who can help them navigate complex decisions and create innovative solutions.

Consider enterprise software sales. Your customers aren’t just buying features and functions. They’re investing in solutions to their business challenges. Can you help them visualize how your product transforms their operations? Do you understand their workflow well enough to spot opportunities they might have missed?

Trust becomes your most powerful differentiator in this environment. But how do you build it? Through actions, not words. When you genuinely prioritize customer success over immediate sales, people notice. They remember when you steered them away from unnecessary purchases or suggested more cost-effective solutions.

The modern sales process demands a deeper understanding of your customer’s business context. You’re not just matching products to needs – you’re helping define those needs. What problems keep your prospects awake at night? Which industry trends threaten their market position? How can your solution help them stay competitive?

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Two Tall Guys Talking Sales – Sales Intelligence 101: Using AI and Networking to Target Ideal Customers – E112

By Sean O'Shaughnessey

Welcome to another compelling episode of Two Tall Guys Talking Sales with hosts Kevin Lawson and Sean O’Shaughnessey! Kevin and Sean dive deep into a central challenge for sales teams: identifying ideal customers and building a robust prospect list. In this episode, they uncover practical strategies, share indispensable tools, and illustrate how a strong grasp of your customer can turn prospects into loyal clients. Whether you’re part of a lean sales team or managing large territories, this episode is loaded with insights to help you grow.

Key Topics Discussed

Building Your Prospect List (approx. 2:00): Kevin introduces the concept of creating an ideal prospect list and breaks down the importance of strategic targeting beyond mere proximity or broad industry fit.
Activating and Leveraging Networks (approx. 3:00): Both hosts discuss the value of networking to uncover warm referrals, emphasizing the need to build a customized, one-to-one outreach strategy.
Effective Tools for Targeting Customers (approx. 4:45): Sean and Kevin highlight essential tools like LinkedIn Sales Navigator, KnowledgeNet, and AI-powered tools like Perplexity to streamline the process of finding and qualifying leads.
Understanding the Customer’s Goals and Structure (approx. 7:20): Sean shares a story about understanding internal company dynamics and how knowing a prospect’s structure and goals helps in creating value-oriented solutions.
Actionable Research Insights (approx. 10:15): The duo dives into practical research techniques to understand client organizations and stakeholders, stressing that informed sellers are empowered sellers.

Key Quotes

Kevin: “To build a good prospect list, it doesn’t have to mean endless hours on Google or hundreds of cold calls. With the right tools, you can have a list ready before lunch.” (approx. 5:55)
Sean: “Your job isn’t just to sell a product; it’s to solve a problem. When you start with that goal, the sale becomes almost inevitable.” (approx. 14:40)
Kevin: “Whether you’re a team of one or a team of five, using the tools at hand to maximize your reach and impact makes you competitive.” (approx. 13:00)

Additional Resources

A Significant Actionable Item from this Podcast

Leverage AI-powered tools to gain deeper insights into target companies and individuals before engaging in outreach. By using resources like Perplexity to understand a client’s structure, goals, and decision-making processes, salespeople can craft highly personalized solutions that add immediate value.

In the episode, Sean challenged people to use Perplexity to research his fellow co-host, Kevin Lawson. Here is that Perplexity search: https://www.perplexity.ai/search/can-you-help-me-with-informati-Hdjvd9OgQTWFXrODrlhHnQ

In this episode, Kevin and Sean clarify that sales is about more than products—it’s about partnerships. Discover how to empower yourself with the right tools, refine your approach to prospecting, and bring authentic value to each client. Tune in to Two Tall Guys Talking Sales for actionable strategies to transform how you engage, connect, and close.

From Chaos to Order: Improve Your Sales Productivity with Effective Pipeline Management

By Sean O'Shaughnessey

Sales is a complex and intricate world, a jigsaw puzzle where each piece must fit perfectly to create a successful picture. This is especially true when it comes to managing sales, whether you’re a salesperson, a sales manager hoping to enhance your leadership skills, or a CEO in the trenches of a small company. Understanding the challenges and nuances of the sales process is crucial to increasing revenue and productivity.

Imagine you’re in a room full of sports equipment scattered everywhere, from basketball shoes to cheerleading pom-poms. It’s a total mess, and you can barely see the floor. This is a perfect metaphor for what a disorganized sales pipeline can look like. It’s messy chaotic, and there’s always something that doesn’t quite smell right.

The sales pipeline is vital for tracking and managing sales prospects from the initial contact to the deal’s closing. It visually represents where potential customers are in the sales process. However, if not properly managed, the pipeline can become a mess.

A common issue is when a deal gets pushed from one month to the next. The sales rep simply changes the closing date, making it seem like procrastination has become a part of the process. This can be due to various reasons, such as a lack of commitment from the customer, the sales rep not understanding the customer’s needs, or simply a lack of follow-up. To avoid this, it’s essential to go back to basics. Understand where the customer is in their evaluation and buying process. Are they genuinely interested in buying or just exploring the idea? It’s perfectly fine for a customer to be in the exploratory stage, but that doesn’t mean they’re ready to buy. These customers should be considered early-stage prospects and not be rushed into buying.

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The Right Person in the Right Seat: Unleashing Company Growth through Strategic Sales Leadership

By Sean O'Shaughnessey

A recurring issue for small companies has emerged; the company’s owner or CEO often leads the sales department. This might be because they believe no one else can sell their product or service better than they can. However, this mindset might be hampering the company’s growth potential.

If you’re a company owner or CEO who leads sales, it’s crucial to consider the risk of this approach. When the person leading the company also heads sales, the business is constrained by the amount of time that leader has. If your salespeople consistently wait for your input or response, you might face a growth opportunity and a challenge simultaneously.

The solution lies in de-risking your organization’s growth potential by getting a sales leader in the sales leadership seat separate from you. This concept resonates with the theory of constraints, a principle often applied in the manufacturing industry but equally applicable in sales. The theory of constraints focuses on identifying the factors that limit your success.

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