『How to Run a One-on-One Sales Meeting That Actually Improves Sales Performance』のカバーアート

How to Run a One-on-One Sales Meeting That Actually Improves Sales Performance

How to Run a One-on-One Sales Meeting That Actually Improves Sales Performance

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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. Key Topics Discussed Take Ownership of Your One-on-One Sales Meeting — 01:18 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. Start With the Scoreboard: Dollars, Deals, and Obstacles — 03:23 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. Use the Meeting to Close the Loop on Commitments — 06:32 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. Your Pipeline Is Not the Entire Meeting — 08:28 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. Run Your Territory Like a Business—and Ask to Be Coached — 09:11 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. Demand Useful Feedback, Not Empty Praise — 11:01 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. Key Quotes Sean O'Shaughnessey — 01:18 "You should have the philosophy of this is your meeting." 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. Kevin Lawson — 02:47 "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." The manager can provide resources, coaching, and organizational support, but ownership of the opportunity remains with the salesperson. Kevin Lawson — 08:52 "Pipeline is not the only content for a pipeline meeting." 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. Sean O'Shaughnessey — 13:09 "You need your leadership to help you get better, and you need to ...
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