sales meeting

From Reporting to Coaching: Elevate Your One-on-One Sales Meetings to Drive Performance and Trust

By Sean O'Shaughnessey

A one-on-one sales meeting is not a reporting meeting. It’s not about reviewing what already happened. And it’s definitely not about the manager doing most of the talking. The purpose of a one-on-one pipeline review is to develop the salesperson, surface challenges, and accelerate opportunities. If your one-on-ones are anything less, you’re leaving performance on the table.

Sales leaders often default to micromanagement.

Especially when the rep is new or struggling. But that approach backfires. It creates dependency and stifles problem-solving. The goal is to coach your reps into leading the meeting. That shift changes everything. When reps own the agenda and bring forward deal-level insights, they’re forced to think critically. That’s where growth happens.

If you’re leading a sales team or are a CEO playing the role of sales manager, you need to establish a clear structure. But the rep does the prep. You define the meeting cadence and format. Weekly or bi-weekly, depending on your velocity. You outline the sections: committed deals, stalled deals, and at-risk deals.

But the rep fills in the content. They come to the meeting ready to walk you through each opportunity, with specific updates and clear asks.

Preparation is non-negotiable. For both sides.

The salesperson should have updated their CRM before the meeting. The manager should have reviewed that data in advance. If either party shows up unprepared, the meeting becomes reactive.

A waste of time. And it erodes trust quickly.

Reps notice when you haven’t read the notes. They know when you’re winging it. And if they feel their effort isn’t valued, they’ll stop putting in the effort.

You want to create a culture where preparation is expected and rewarded.

The fastest way to management failure is to ask questions that could have been answered by reading the CRM. Instead, use that time:

To probe deeper.
Ask about the deal strategy.
Challenge assumptions.
Help salespeople spot gaps they missed.

That’s where your experience has real value.

It’s tempting to jump in and solve the problem. Especially when you see the red flags before the rep does. But resist the urge. Let them talk it through. Coach them toward the insight. Your job isn’t to close the deal; it’s to build someone who can. That means teaching them how to identify weak spots, how to pressure test a deal, and how to re-engage a stalled buyer. The real value of one-on-ones is in that development.

Think about how you coach.

Are you diagnosing for them? Or are you helping them diagnose for themselves? When a rep says “this deal is solid, no issues,” that’s a red flag. Every deal has risk. Your job is to help them uncover it. Ask: “What’s the biggest thing that could derail this?” Or “What’s the last thing the buyer said that gave you pause?” These questions surface the truth. And they teach reps to self-assess more effectively.

There’s a fine line between coaching and grading. You want reps to be honest about their pipeline without fear of judgment.

If a deal is weak, that’s not a character flaw. It’s a coaching moment.

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Two Tall Guys Talking Sales – Winning Sales Strategies for Productive, High-Impact Pipeline Reviews – Episode 149

By Sean O'Shaughnessey

Pipeline reviews don’t need to feel like an ambush. In this episode, Kevin Lawson and Sean O’Shaughnessey break down how to turn pipeline meetings into high-value working sessions that improve sales management, strengthen sales processes, and accelerate revenue generation. The conversation focuses on preparation discipline, trust, and transparency, as well as a practical playbook for advancing complex deals through relationship mapping and peer-to-peer executive engagement.

You’ll hear straightforward sales strategies you can implement immediately, whether you lead a large enterprise team or a small, founder-led organization. Expect a sharp focus on business acumen, value selling, and the day-to-day messaging that keeps deals moving. The result is a meeting format that fuels sales success and better revenue management, not another hour of defensive status reporting.

Key Topics Discussed

Make pipeline reviews not suck — Focus the agenda on the few deals that genuinely need help; skip deep dives on healthy opportunities. [~00:00:00]
The salesperson’s prep checklist — Current notes, clear qualification status, and a concrete next step; never open with “I need to get a meeting.” [~00:03:00]
Trust, transparency, and speed — Why open admission of gaps prevents executive “gotchas” and keeps the team collaborative. [~00:04:34–00:05:34]
Taming the “big deal” distraction — How sales leaders manage CEO attention and ensure one opportunity doesn’t hijack the meeting. [~00:07:52–00:08:20]
Relationship mapping for top deals — Title-to-title engagement, executive assignments, and the “11-on-11” football metaphor for flawless execution. [~00:09:00–00:11:55]
Adapting for smaller orgs — Three-on-three analogy, “weaponize” your internal team as peer resources, and coach reps to lead 1:1s. [~00:12:30–00:15:06]

Key Quotes

Sean O’Shaughnessey [~00:01:36]: “Bring up the ones that hurt, the deals where you need help. Wouldn’t it be nice to get helped in a pipeline review instead of just being told to ‘get your ass out there and go work on it’?”
Kevin Lawson [~00:05:00]: “Transparency is our key that will keep us moving forward and fast. Sales pipeline meetings don’t have to be the Spanish Inquisition.”
Sean O’Shaughnessey [~00:11:34]: “Run your top deals like you’re running a football team, every player knows their assignment, and you execute flawlessly.”
Kevin Lawson [~00:14:33]: “For one-to-ones, the salesperson should be leading the meeting, your job is to coach them to bring challenges you can clear.”

Additional Resources (mentioned in the episode)

Sales Meeting Agenda Templates — Free downloadable agendas for effective pipeline reviews and 1:1s (from Sean and Kevin’s sites).
B2B Sales Lab Community — A peer-led forum to refine sales strategies, strengthen messaging, and accelerate revenue generation. https://b2b-sales-lab.com/

A Significant Actionable Item from this Podcast

Adopt the “Help-First Pipeline Review” and Relationship Map.

Before your next review, split your pipeline into two lists: On-Track and Needs Help. Use meeting time almost exclusively on the “Needs Help” list. For each flagged deal, arrive with: (1) current status and qualification level, (2) the single next step, and (3) a relationship map that pairs your execs and functional leaders title-to-title with the customer’s counterparts (CEO↔CEO, CFO↔CFO, VP Eng↔VP Eng). Assign those internal players specific outreach tasks and deadlines. This simple shift transforms pipeline reviews into working sessions that improve sales management, sharpen sales processes, and advance value-based conversations, fast.

Two quick tips to lock it in:

Never start with “I need to get a meeting.” Instead, say, “I’m trying to reach Larry; here are the three touches I’ve already made and my next move.”
Preempt “big deal” derailments by updating its status in CRM ahead of time and summarizing it briefly; then return to the prepared “Needs Help” list.

Summary

If pipeline reviews feel like public performance reviews, this conversation will reset the culture. Kevin and Sean outline a decisive, repeatable approach that blends business acumen, crisp messaging, and practical value selling to move deals. By prioritizing help over inspection, mapping peer-to-peer relationships, and coaching reps to lead, you’ll turn a dreaded ritual into a lever for sales success and consistent revenue management. Queue it up, your next pipeline meeting can actually be the best hour of your sales week.

Two Tall Guys Talking Sales – Breaking the Silos: Aligning Sales and Marketing for Real Revenue Growth – Episode 147

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey dive deep into one of the most misunderstood dynamics in business: the relationship between sales and marketing. Pulled directly from a thought-provoking question inside the B2B Sales Lab community, this conversation explores how sales teams can contribute meaningfully to marketing efforts and why that collaboration drives better revenue generation. Whether you lead a sales team, run marketing campaigns, or wear both hats in a small business, this episode gives you practical strategies to align your teams, sharpen your messaging, and enhance sales success.

Key Topics Discussed

The Role of Sales in Marketing & Content Development (00:00)
How sales leaders can become strategic contributors to content and campaign direction.
Being the Voice of the Customer Across the Business (00:02)
Why sales must act as a conduit of market intelligence, not just for marketing but across production, delivery, and operations.
Sales Behavior That Builds or Breaks Internal Trust (00:04)
The importance of accountability and humility when offering feedback to other departments.
Making Marketing a Regular Part of Sales Meetings (00:08)
A tactical breakdown of how to engage marketing in the sales rhythm without derailing productivity.
Field Collaboration: Invite Your Internal Teams to Ride Along (00:10)
Why taking engineers or operations managers on customer calls creates stronger cross-functional empathy and better customer experiences.
Marketing Assets: Create Them, Use Them, Give Feedback (00:12)
How to close the feedback loop on content effectiveness and ensure sales uses what marketing builds.

Key Quotes

“Sales is accountable for driving the revenue, but sales is also accountable for working with marketing to get to a market-facing message that addresses current needs.”
— Kevin Lawson (00:00)
“Your job in sales is to be the best-run department in the company. If you’re not, your opinion probably doesn’t matter.”
— Sean O’Shaughnessey (00:08)
“Please, oh please, use the tools your marketing team creates for you. If you don’t, that’s on you.”
— Kevin Lawson (00:12)
“There’s no better way to get internal teams aligned with customers than to take them on sales calls. Let them breathe your air and eat at Burger King between meetings.”
— Sean O’Shaughnessey (00:11)

Additional Resources

B2B Sales Lab Community: A peer group for sales professionals focused on sharpening sales processes, messaging, and revenue management. www.b2b-sales-lab.com

A Significant Actionable Item from this Podcast

Hold a joint sales-marketing meeting each quarter.

Schedule a dedicated 30-minute session within your sales team’s recurring meeting where your marketing counterpart joins to review current messaging, upcoming campaigns, and voice-of-the-customer insights. Let marketing ask questions, present new content, and gather sales feedback. Use this as a structured loop to align both teams on business acumen, sales strategies, and revenue goals.

Why You Should Listen Now

If you’ve ever wondered why your sales messaging isn’t landing or why marketing feels “out of touch,” this episode is for you. Kevin and Sean pull back the curtain on how high-performing sales organizations dissolve silos, share real-time customer feedback, and co-create assets that drive revenue. Whether you’re a VP of Sales, a marketing leader, or a business owner trying to scale effectively, you’ll walk away with ideas you can implement this week to align your teams for better revenue generation and sales success. Tune in now and start building the team your customers deserve.

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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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!

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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Building a High-Performing Sales Team: The Benefits of Recognizing Effort and Results in Sales Meetings

By Sean O'Shaughnessey

Sales drives the engine of any B2B business. Enhancing sales strategies and management capabilities is crucial to success for salespeople, sales managers, and CEOs of small companies. One aspect of this involves rewarding effort and results during sales meetings. This practice motivates the sales team and encourages them to strive for better performance.

Salespeople are naturally competitive and driven, but they also appreciate recognition. While a paycheck is important, it’s also essential for salespeople to feel valued and appreciated for their efforts. This recognition can come in various forms, from verbal praise to tangible rewards. It’s important to remember that recognition should not be limited to monetary rewards. The simple act of acknowledging someone’s hard work and contributions can be incredibly motivating.

A sales meeting is an opportune moment to recognize and reward your sales team’s efforts. It’s not just about discussing targets and strategies; it’s also a chance to celebrate successes, however big or small. These meetings can be used as a platform to highlight the best practices and strategies employed by the team members, fostering a culture of learning and improvement.

Every salesperson has a unique approach and strategy. If nothing else, they experiment with different ways to share the benefits of their product or ask a particular discovery question. By sharing these individual successes or failures during meetings, sales teams can learn from each other, thus promoting a collaborative and supportive environment. The sales leader may prompt these discussions, but the actual learning comes from the experiences and strategies the salespeople share.

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Driving Sales Success through Collaborative Learning and Knowledge Sharing

By Sean O'Shaughnessey

Aiming to increase revenue and boost productivity in sales processes, sales managers and company CEOs are constantly searching for effective strategies to streamline their operations and ensure optimal results. One such strategy involves conducting sales meetings for educational purposes. These meetings focus on enhancing knowledge and skills, and this is where the real game begins.

Imagine a sales meeting where, instead of a mundane round-up of weekly activities, there’s an engaging discussion about a new book that can potentially revolutionize the sales process. Picture a team of four or five salespeople, including you, each reading two chapters of a book overnight. The next day, everyone shares the high-level takeaways from their assigned chapters. This practice allows the team to consume an entire book’s content in a day and empowers each member to become an authority on the subject matter because they’re teaching others. The exercise is educational, promotes team collaboration, and enhances communication skills.

This approach can be extended beyond books to other areas, such as market research. For instance, if a company is looking to enter a new vertical, different aspects of the industry, like market influencers, challenges, and political, economic, and legal factors, can be assigned to team members for research. Each member returns their findings to the team, comprehensively understanding the new market. This practice is not merely busy work; it’s sales-driving work that benefits the entire team and accelerates learning about the new market.

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Maximizing Sales Team Productivity: The Importance of Effective Sales Meetings

By Sean O'Shaughnessey

Numerous factors can contribute to a sales team’s success or failure. Two key aspects that are often overlooked yet hold immense importance are the structure and content of sales meetings. These gatherings are not just about reporting numbers or discussing targets. They are platforms for learning, sharing, and strategizing that can significantly boost a sales team’s performance.

One of the fundamental principles of a productive sales meeting is having a clear plan. This doesn’t mean having a rigid agenda without room for spontaneity. On the contrary, it’s about having a framework that guides the discussion and ensures that the meeting stays focused on the key topics at hand.

A common mistake many sales leaders make is covering too many topics in a single meeting. In an attempt to address every issue, they often skim the surface of each topic without delving deep into any. The result is a meeting lacking depth and tangible insights or solutions. Limiting the number of key topics to one or two per meeting is advisable to avoid this. This allows for a more in-depth discussion and a better understanding of the issues at hand.

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Maximizing Productivity in Sales Meetings: Key Principles and Best Practices

By Sean O'Shaughnessey

Sales meetings are the lifeblood of any sales-driven organization, providing an essential forum for communication, collaboration, and strategy development. Yet, despite their significance, many salespeople, managers, and CEOs struggle to conduct productive and efficient meetings. This issue often stems from a lack of understanding of key meeting principles and best practices, particularly in the areas of time management, content planning, and participant engagement.

The adage “time is money” holds especially true in sales. Every minute counts, and wasted time equates to lost opportunities. This is why punctuality is of the utmost importance. A meeting that starts late or runs over time is disrespectful to participants and detrimental to the team’s overall productivity.

To avoid this pitfall, sales leaders should ensure they always arrive early to meetings and start them on time, without exception. This requires careful planning and preparation, as well as a commitment to respecting the time and schedules of others. The same principle applies to the end of the meeting. Sales leaders should always strive to conclude meetings on time, which requires careful meeting agenda management and a willingness to keep discussions focused and on track.

Content planning is another crucial aspect of effective meeting management. Just as a ship needs a compass to navigate the seas, a meeting needs an agenda to guide its proceedings. A well-crafted agenda provides a clear structure for the meeting and helps to keep discussions focused and productive. It also sets clear expectations for participants and helps to ensure that all relevant topics are covered.

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