trust

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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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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Becoming a Trusted Advisor: Solve Problems, Not Just Sell Products

By Sean O'Shaughnessey

In B2B sales and sales leadership, problem-solving is an art that goes beyond selling a product or service. The secret to becoming a trusted advisor is addressing business problems, not just selling a product. This concept resonates with salespeople, sales managers, and small business CEOs who sell themselves or manage a team of salespeople.

Sales is not just about pushing a product or closing a deal; it’s about forging relationships, understanding businesses and their unique challenges, and offering solutions to these problems. The role of a trusted advisor is not to sell a product and become a trusted advisor, but rather to become a trusted advisor who can sell a product.

The reward for earning trusted advisor status is immeasurable. It is fantastic to receive a call from a client asking for advice on solving problems they have never discussed with you. Imagine having relationships that stand the test of time and outlast competition and challenges.

So, how does one become a trusted advisor and solve problems for clients rather than just selling them a great product? It starts with building a relationship from scratch. When starting with a prospect list or an ideal client profile, the goal is not to find anyone who will respond but to seek opportunities to build meaningful relationships.

The cornerstone of these relationships is reliability.

Are you always punctual?
Do you cancel at the last minute?
Do you forget to return phone calls?

These behaviors erode trust. On the other hand, showing up when needed, providing solutions even when they are not directly related to your product or service, and connecting clients to others who can help them are behaviors that build trust.

Becoming a trusted advisor also involves understanding and curiosity about the client’s business. Do you ask questions about how the prospective company makes and loses money, how it dealt with past challenges like the pandemic, and how it deals with current challenges like rising inflation or supply chain disruption? The aim is to understand the client’s business, challenges, and competitors and offer insights and parallels to other companies.

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The Power of Personal Branding in Enhancing Sales Productivity

By Sean O'Shaughnessey

Navigating the world of sales can sometimes feel like traversing a labyrinth. Salespeople, sales managers, and CEOs alike grapple with the challenge of increasing revenue and enhancing productivity in their sales processes. To be successful, you need more than knowledge of products and services; you need to develop trust and a strong personal brand.

Business-to-business (B2B) sales involves transferring trust from ourselves to our prospects. We trust in our products and company, but convincing prospects to share that trust is the real challenge. This trust should encompass the product, the company, and perhaps most crucially, the salesperson. Remember, B2B sales could be defined as helping prospects decide in our favor within the desired timeframe.

The key to B2B sales is developing a personal brand that inspires trust in salespeople. The salesperson’s ability to convey reliability, expertise, and credibility can significantly influence how fast a prospect invests in a product or service.

Developing a strong personal brand begins with creating a presence that signals control and understanding of the business. This can be achieved by showcasing the benefits of your product or service to your customer’s business. A straightforward way to build your brand is by seeking references from your network, former employers, and customers, and showcasing these on professional platforms like LinkedIn.

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Two Tall Guys Talking Sales – Measuring Marketing Success with Amy Connor of CMO OnLoan – E126

By Sean O'Shaughnessey

Welcome back to another episode of Two Tall Guys Talking Sales with Kevin Lawson and Sean O’Shaughnessey! This week, we’re diving deep into measuring marketing effectiveness with special guest Amy Connor, founder of CMO OnLoan. If you’ve ever struggled to connect marketing strategies to real business results, this episode is for you. Grab your marketing colleague and tune in—understanding what’s working (and what’s not) in your marketing is the key to driving sales growth.

Key Topics Discussed:

The Importance of Measuring Marketing Performance (01:08)
Many companies don’t effectively track their marketing impact. Amy shares how focusing on key metrics—without overwhelming dashboards—can create a direct path to success.
Sales and Marketing Must Be Aligned (02:09)
Customers don’t see marketing and sales as separate—they see one company. Amy explains why integrating both functions is crucial for a seamless customer journey.
Why Vanity Metrics Don’t Matter (02:55)
Impressions, clicks, and leads may look impressive, but if they don’t translate to business results, they don’t matter. Learn how to focus on meaningful data that connects to revenue.
The Billboard Advertising Myth (03:12)
Can a billboard drive B2B sales? Amy and Sean discuss the realities of traditional advertising and why small businesses should think critically about marketing spend.
Aligning Sales Messaging with Marketing Content (05:57)
Sales teams shouldn’t be the only ones communicating key messages. Amy shares why marketing content must reinforce what salespeople say to build trust and shorten sales cycles.
Tactical vs. Strategic Marketing – What’s the Right Balance? (08:29)
Should your marketing focus on brand awareness or immediate sales action? Amy explains the difference and how to measure each effectively.

Key Quotes:

Amy Connor: “Marketing and sales are part of the customer’s journey in a united way. The customer doesn’t see ‘marketing did this and sales did that’—they see the company as a whole.” (01:45)

Sean O’Shaughnessey: “Salespeople start at a disadvantage because buyers inherently don’t trust them. That’s why marketing must reinforce their message to build credibility.” (05:40)

Kevin Lawson: “Up to 70% of the buyer’s journey happens before they talk to sales. If marketing isn’t working ahead of time, you’re already losing.” (07:52)

Additional Resources:

Visit CMO OnLoan for free marketing resources: www.cmo-onloan.com
Connect with Amy Connor on LinkedIn: Amy Connor LinkedIn
Listen to the first episode featuring Amy: Last Week’s Podcast: https://podcasts.apple.com/us/podcast/amy-connor-discusses-salespeople-vs-lead-generation/id1668686029?i=1000693738159

A Significant Actionable Item from this Podcast:

Audit Your Marketing Metrics
Take 30 minutes this week to assess what marketing data your company is tracking. Are you focusing on impressions and clicks or lead conversion and revenue impact? Identify one metric that directly connects marketing activity to business growth and make it your priority.

Why You Should Listen to This Episode

Marketing is more than just branding—it’s a revenue-driving function. In this conversation, Amy Connor unpacks how B2B companies can measure what truly matters, align sales and marketing, and ensure every dollar spent on marketing contributes to the bottom line. If you want your marketing efforts to drive real sales results, don’t miss this insightful discussion. Tune in now!

Two Tall Guys Talking Sales – Sales Slumps & Hot Streaks: How to Build a Predictable Pipeline – E122

By Sean O'Shaughnessey

Sales is a game of ups and downs, but what separates top performers from the rest is their ability to keep the funnel full—even when they’re closing deals. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey dive into the art and science of building a consistent pipeline. They discuss strategic approaches to prospecting, leveraging data tools, and the importance of curiosity in sales conversations. Whether you’re starting fresh in Q1 or looking to level up your approach, this episode is packed with actionable insights to keep your sales engine running smoothly.

Key Topics Discussed

🔹 The Sales Roller Coaster – Why salespeople experience cycles of high revenue followed by dry spells and how to smooth out the dips. (00:01:15)

🔹 The First Step: Re-engage Past Clients – Why checking in with existing customers is the easiest way to generate immediate opportunities. (00:02:23)

🔹 Using Free Data Resources to Prospect – How Data Axle and Apollo.io can help salespeople generate lists of high-potential prospects at no cost. (00:03:00)

🔹 Turning Leads Into Prospects – The difference between having a database of names and actually engaging with real sales opportunities. (00:05:31)

🔹 The Power of Networking and Curiosity – How to leverage your network to gain insights about a company before reaching out to decision-makers. (00:10:39)

🔹 Climbing the Ladder to the Decision-Maker – Why you shouldn’t start at the top and how building relationships within an organization can earn you a trusted introduction. (00:14:37)

Key Quotes

💬 Sean O’Shaughnessey on avoiding the sales roller coaster:
“If I go back to my drain-the-swamp analogy, you gotta put water back in the swamp, you gotta let it rain, gotta make it rain.” (00:02:02)

💬 Kevin Lawson on the importance of planning:
“Too often, salespeople stop after the second or third introduction. Timing is everything—keep going, keep networking, and keep qualifying your ideal client profile.” (00:12:39)

💬 Sean O’Shaughnessey on reaching executives:
“You cannot send an email to the CEO and expect it to be read. You are just a salesperson. If you want to sell to the top, you need a referral—and probably from someone lower in the organization.” (00:14:37)

Additional Resources

📌 Data Axle – A powerful business database often available through public libraries. Check with your local library for free access.

📌 Apollo.io – A free tool offering up to 10,000 business contacts per month to help with prospecting.

📌 Lighthouse Sales Advisors Coaching – Kevin Lawson offers 1:1 coaching to help sales professionals refine their strategies. Learn more here.

A Significant Actionable Item from this Podcast

Take 30 minutes this week to evaluate your sales pipeline using the “circle exercise.”

Draw a circle and estimate what percentage of your revenue will come from existing clients vs. new clients.
Identify how many new deals you need to hit your quota.
Rank your existing leads based on fit and potential.
Develop a networking plan to move from a name on a list to an engaged prospect.

Doing this exercise will give you clarity on where to focus your efforts and how to strategically fill your pipeline.

Why You Should Listen to This Episode

Struggling with an empty pipeline after closing strong last year? You’re not alone. In this fast-paced, insight-packed episode, Kevin and Sean break down the fundamental strategies that separate high-performing salespeople from those stuck on the revenue roller coaster. Whether you’re looking for free prospecting tools, better ways to approach networking, or a foolproof plan to keep your sales funnel full, this episode delivers practical tactics you can apply immediately.

🎧 Tune in now and take control of your sales pipeline!

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 Art of the Discovery Call: Build Respect and Close More Deals – E120

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey tackle one of the most critical yet underestimated aspects of sales: the discovery call. Are you guilty of “winging it” during these pivotal conversations? Tune in as Kevin and Sean break down the importance of crafting a tailored question bank, share actionable tips to elevate your discovery process, and reveal how asking the right questions can transform your sales game. If you’re looking to close more deals and gain the respect of your prospects, this is the episode for you.

Key Topics Discussed

The Danger of Winging It in Discovery Calls (Approx. 00:00:00)
Kevin and Sean explain why improvising during discovery calls can lead to missed opportunities and how a question bank can save the day.
Building an Effective Question Bank (Approx. 00:01:00)
Learn how to create a dynamic set of questions tailored to different industries and titles, ensuring every prospect feels understood.
The Power of Open-Ended Questions (Approx. 00:05:00)
Discover why “what” and “how” questions are more effective than “why” questions in fostering productive, trust-building conversations.
The ROI of Better Discovery Questions (Approx. 00:07:00)
Explore how better discovery leads to more accurate forecasts, stronger relationships, and increased respect from prospects.
Refining Your Question Bank Over Time (Approx. 00:12:00)
Kevin and Sean emphasize the importance of regularly reviewing and updating your questions to stay relevant and effective.

Key Quotes

Kevin Lawson: “You should never ask a question on a discovery call that you could find the answer to with public information. That’s a waste of your prospect’s time and shows you haven’t earned their business.” (Approx. 00:10:27)
Sean O’Shaughnessey: “Why questions feel like interrogation. Great discovery questions start with what and how—they build trust and uncover real insights.” (Approx. 00:06:25)
Kevin Lawson: “Writing down your questions allows you to tweak, hone, and refine them. It’s the preparation that separates good sellers from great ones.” (Approx. 00:09:05)

A Significant Actionable Item from this Podcast

Start Your Own Question Bank Today
Set aside 30 minutes to brainstorm 10-15 open-ended questions for your next discovery call. Categorize them by industry and prospect title. Use these questions in your next call, then evaluate their effectiveness. Adjust and refine over time to create a winning formula.

Summary

Mastering the discovery call is essential for any successful salesperson, and in this episode, Kevin and Sean provide the ultimate guide to getting it right. From crafting a versatile question bank to leveraging open-ended questions that build trust and uncover insights, this episode is packed with actionable advice to transform your sales process. Don’t miss this opportunity to elevate your skills and close more deals—listen now and discover the art of the perfect discovery call!

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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