How to Run a One-on-One Sales Meeting That Actually Improves Sales Performance
Kevin Lawson and Sean O'Shaughnessy discuss how to transform one-on-one sales meetings from mere pipeline inspections into productive coaching and resource allocation sessions. They provide a structured agenda framework that emphasizes preparation, obstacle identification, and demanding accountability from sales leaders to improve performance and revenue.
Summary
The episode challenges the common practice of treating one-on-one sales meetings as simple pipeline reviews. Kevin and Sean argue that these meetings should be strategic sessions where salespeople take ownership and surface obstacles blocking deals, while sales leaders provide coaching and resources needed for success.
For salespeople, the key is preparation and framing the meeting as their own. They recommend spending time beforehand to know deal details and identify areas where help is needed. The speakers introduce a structured agenda format that begins with a 'scoreboard' section: salespeople should clearly state which deals they expect to close in the period (by dollar amount) and identify specific concerns or blockers on each deal.
Following the scoreboard, the agenda should cover 'to-do items'—a recap of commitments from the previous meeting, allowing salespeople to track what support they requested and whether it was delivered. This ensures half-finished projects don't accumulate and keeps both parties accountable.
Critically, the speakers emphasize that pipeline discussion should not dominate the entire conversation. Instead, the meeting should function like a board meeting where the salesperson is the CEO of their territory, and the sales manager is the chairman of the board. This mental model shifts the dynamic from reporting activity to strategically requesting resources and coaching.
Sean illustrates this with a personal story about challenging a new VP of Sales who gave only generic praise instead of constructive feedback. By demanding real coaching and feedback on areas for improvement, Sean forced his manager to actually lead. The speakers stress that salespeople should ask for skills-building sessions, recorded call reviews, and specific suggestions for improvement—and should insist on getting them.
The episode concludes by emphasizing that salespeople typically have only 30-40% of their time in front of customers, making the remaining 70% of time—including weekly meetings—critical to optimize. A well-structured one-on-one meeting repeated 50+ times per year can meaningfully impact effectiveness and results.
About this episode
<p dir="ltr">A one-on-one sales meeting should not be a passive status report where the salesperson waits for the manager to ask questions. Done correctly, it becomes one of the most valuable tools for improving sales performance, removing obstacles, strengthening skills, and accelerating revenue generation. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey explain how salespeople can take greater ownership of these conversations—even when their sales manager has not created an effective structure. From forecasting the deals you expect to close to asking for resources, coaching, and candid feedback, Sean and Kevin lay out a practical framework for turning recurring one-on-ones into working sessions that support better sales processes, stronger sales management, and ultimately greater sales success.</p> <h2 dir="ltr">Key Topics Discussed</h2> <p dir="ltr">Take Ownership of Your One-on-One Sales Meeting — 01:18<br /> The salesperson should arrive prepared rather than treating the meeting as something the manager owns. Know the details of your opportunities, understand where you need help, and be ready to direct attention toward the issues that could materially affect your results. Kevin describes the meeting as an enablement resource: your job is to own the deal, while your sales leader can help mobilize marketing, technical, consulting, or other internal resources needed to win it.</p> <p dir="ltr">Start With the Scoreboard: Dollars, Deals, and Obstacles — 03:23<br /> Sean recommends beginning with a clear statement of what you expect to close during the relevant sales period—whether that is the week, month, quarter, or another cadence appropriate to the business. Then identify the concerns surrounding those opportunities. Where is the deal blocked? What support is missing? What could prevent the projected revenue from becoming real revenue? This moves the discussion beyond vague pipeline updates and toward concrete decisions that can improve Pipeline Velocity and deal execution.</p> <p dir="ltr">Use the Meeting to Close the Loop on Commitments — 06:32<br /> Kevin breaks the meeting into a scoreboard followed by the outstanding to-do items from prior conversations. That accountability runs in both directions. Salespeople should report on what they committed to doing, but they should also appropriately "lead up" by asking managers about resources, introductions, or assistance that was previously promised. Doing this prevents half-completed initiatives from accumulating and ensures the AE or salesperson receives the Sales Enablement support needed to move Complex Deals forward.</p> <p dir="ltr">Your Pipeline Is Not the Entire Meeting — 08:28<br /> Pipeline matters, but Kevin warns against allowing pipeline inspection to consume the entire conversation. A productive one-on-one should also address problems, resources, execution, and development. A sales management system that does nothing more than repeatedly ask, "When is this deal closing?" leaves enormous value on the table. The meeting should help the salesperson improve the business, not merely describe it.</p> <p dir="ltr">Run Your Territory Like a Business—and Ask to Be Coached — 09:11<br /> Sean suggests thinking of yourself as the CEO of your territory, with your sales leader serving as the chair of your board. You are responsible for the performance of that business, but you should also expect the leadership team to provide resources and guidance. That includes skills development. Ask your manager to review recorded calls, presentations, and customer conversations and provide specific coaching about what could have been done better.</p> <p dir="ltr">Demand Useful Feedback, Not Empty Praise — 11:01<br /> Sean tells the story of challenging a newly promoted VP of Sales who accompanied him on customer calls but initially offered nothing beyond praise. Sean had already identified five things he could have done better and pushed his manager to provide equally substantive feedback. The lesson is not to imitate Sean's rather dramatic airport maneuver; rather, experienced salespeople still need coaching, and leaders have an obligation to help them improve.</p> <h2 dir="ltr">Key Quotes</h2> <p dir="ltr">Sean O'Shaughnessey — 01:18</p> <p dir="ltr">"You should have the philosophy of this is your meeting."</p> <p dir="ltr">Salespeople who take responsibility for the preparation, agenda, and desired outcomes of their one-on-one put themselves in a far stronger position to get the resources and coaching they need.</p> <p dir="ltr">Kevin Lawson — 02:47</p> <p dir="ltr">"Your name's on the deal, and so it's up to you to figure out how you're going to win the deal and reach your quota."</p> <p dir="ltr">The manager can provide resources, coaching, and organizational support, but ownership of the opportunity remains with the salesperson.</p> <p dir="ltr">Kevin Lawson — 08:52</p> <p dir="ltr">"Pipeline is not the only content for a pipeline meeting."</p> <p dir="ltr">Forecasting matters, but simply reviewing opportunity stages and expected close dates does little to develop the salesperson or remove the problems preventing deals from advancing.</p> <p dir="ltr">Sean O'Shaughnessey — 13:09</p> <p dir="ltr">"You need your leadership to help you get better, and you need to demand it if they're not doing it."</p> <p dir="ltr">Strong salespeople do not outgrow coaching. They become more intentional about seeking useful feedback rather than accepting generic reassurance.</p> <h2 dir="ltr">Additional Resources</h2> <p dir="ltr">B2B Sales Lab — Sean and Kevin invite listeners who want to go deeper into structuring effective one-on-one sales meetings to join the B2B Sales Lab and bring their specific challenges to office hours. The discussion can be tailored to the organization's particular sales process, sales cycle, and management environment. b2b-sales-lab.com</p> <h2 dir="ltr">A Significant Actionable Item from this Podcast</h2> <p dir="ltr">Before your next one-on-one, create a simple, standardized agenda that begins with three things: the deals and revenue you expect to close, the specific risks or obstacles that threaten those deals, and the help you need from your sales leader. Then add outstanding commitments from the previous meeting and at least one skill you want your manager to help you improve.</p> <p dir="ltr">Do not wait for your VP of Sales, manager, or company to design the perfect process for you. Take ownership of the meeting yourself. Over the course of 50 or more meetings each year, improving the quality of these conversations can lead to meaningful gains in sales productivity, better resource allocation, stronger sales strategies, and more predictable revenue.</p> <h2 dir="ltr">Summary</h2> <p dir="ltr">Most salespeople spend far too little of their week actually speaking with customers, which makes poorly structured internal meetings particularly expensive. In this episode, Kevin and Sean challenge both salespeople and sales leaders to stop treating the one-on-one as just another routine pipeline inspection and to start using it as a serious business management session. You will learn how to arrive with a clear scoreboard, surface the barriers threatening important opportunities, hold both sides accountable for commitments, secure the resources necessary to move deals forward, and make coaching an expected part of the conversation. If you want better sales management, sharper execution, stronger business acumen, and one-on-one meetings that actually contribute to B2B sales success, this episode gives you a framework you can put to work before your next meeting.</p> <p><strong id="docs-internal-guid-95a898eb-7fff-0cab-64d4-4be5ef66080e"><br /> <br /></strong></p> <p class="p1"><strong>B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory.</strong> It's a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com</p> <p class="p2"> </p> <p class="p1">You can reach out to Sean at New Sales Expert, LLC - <a href="mailto:[email protected]"><span class="s1">[email protected]</span></a> - <a href="https://www.linkedin.com/in/soshaughnessey/"><span class="s1">https://www.linkedin.com/in/soshaughnessey/</span></a></p> <p class="p2"> </p> <p class="p1">You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - <a href="mailto:[email protected]"><span class="s1">[email protected]</span></a> - <a href="https://www.linkedin.com/in/kwlawson/"><span class="s1">https://www.linkedin.com/in/kwlawson/</span></a></p> <p class="p2"> </p> <p class="p1">You can book time on Kevin's calendar at <a href="https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin"> <span class="s1">https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin</span></a></p> <p class="p2"> </p> <p class="p1">You can book time on Sean's calendar at http://newsales.expert/sean-oshaughnessey-calendar/</p>
Key Insights
- The speakers argue that one-on-one sales meetings have become reduced to pipeline inspections when they should serve multiple purposes including obstacle identification, resource allocation, and coaching—making them fundamentally underutilized.
- Kevin and Sean claim that most salespeople fail to come prepared to these meetings, and that peer salespeople typically do not identify specific deal obstacles or actively request help, creating a competitive advantage for those who do.
- The speakers assert that pipeline discussion dominates meetings at the expense of other critical topics, and that sales leaders—particularly those newly promoted from sales—tend to over-focus on pipeline at the expense of coaching and enablement.
- Sean argues through personal example that salespeople must actively demand coaching and feedback from their managers, and that generic praise without constructive criticism indicates a manager is not effectively leading, requiring the salesperson to force accountability.
- The speakers contend that by framing their territory as a business they run with their sales manager as board chairman rather than supervisor, salespeople shift the meeting dynamic from passive reporting to strategic resource requests and collaborative problem-solving.
Topics
Transcript
Most one-on-one sales meetings become little more than pipeline inspections, but they should be far more valuable than that. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessy explain how salespeople can take ownership of the meeting, surface the obstacles slowing down deals, and get the coaching and resources they actually need from their sales leader. You'll hear why preparation matters, why your pipeline should not dominate the entire conversation, and how a better meeting structure can improve both performance and revenue. If you want your next one-on-one to help you sell more, rather than simply report what happened, keep listening. Back to Two Tall Guys Talking Sales. I'm going to speak to the sales…
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