Two Tall Guys Talking Sales
Midyear exposes the truth in every sales organization. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey tackle a problem many business owners, sales leaders, and salespeople quietly face at the halfway point of the year: unclear goals, weak commission plans, soft pipeline discipline, and the temptation to reset expectations instead of fixing the sales processes that created the gap. This is a practical conversation about B2B sales management, quota accountability, revenue generation, pipeline prioritization, and the uncomfortable but necessary work required to improve sales success in the second half of the year. Key Topics Discussed * Midyear goal setting when the original plan was missing or unclear — 00:00 Sean explains why some companies reach July without properly documented sales goals or commission plans. The corrective action is not complicated, but it is often avoided: write the plan down, align compensation with company priorities, and make sure salespeople know exactly how they are being measured. * Why sales leaders should not casually reset the goal — 02:14 Kevin argues that adjusting the target downward can create a dangerous management precedent. If the number was the right number, the job is to solve the gap through better sales strategies, qualification, activity, referrals, and pipeline focus—not move the scoreboard. * The rare exception to keeping the original quota — 06:34 Sean adds an important leadership caveat. If the CEO or executive team built the number around a product launch, acquisition, market event, or business assumption that never materialized, that is not a salesperson's problem. That is an executive planning problem, and it should be handled honestly. * Pipeline rationalization and better qualification — 09:57 Kevin walks through the discipline of deciding which deals deserve time and which ones do not. Complex deals, unclear next steps, bad-fit opportunities, and stalled prospects all consume selling capacity. Better qualification improves pipeline velocity by giving salespeople time back to pursue better opportunities. * Time management, delegation, and protecting prospecting time — 13:43 Sean warns against the classic sales rollercoaster: closing current business while starving future pipeline. Whether a company uses SDRs, AEs, business development resources, or full-cycle salespeople, every stage of the sales process needs dedicated time. Revenue management requires knowing where the week actually went. Key Quotes * Sean O'Shaughnessey — 01:14 "You didn't get it done at the first of the year. That doesn't mean you can't do it now." * Kevin Lawson — 03:40 "You never adjust the goal. Your job as a salesperson is to hit the goal or your quota." * Sean O'Shaughnessey — 08:34 "Salespeople can't make their goals for things that are outside of their control." * Kevin Lawson — 10:22 "You've got to figure out which deals are aligned and which ones are not aligned to what you do." * Sean O'Shaughnessey — 14:03 "We were so busy selling that we forgot to sell." Additional Resources * EOS implementers — referenced as part of the broader business coaching and planning conversations happening at midyear. * FocalPoint and ActionCOACH — mentioned as examples of coaching organizations business owners may turn to when trying to catch up or plan ahead. * Microsoft PTAP — referenced by Kevin as "plan to exceed plan," a useful framing for quota planning and sales performance management. * MEDDPICCC, BANT, and SPICED-style qualification methodologies — referenced as examples of structured approaches to qualification, deal inspection, and sales process discipline. * Marketing-generated digital assets — discussed as one practical source of conversation creation when salespeople are behind and need to rebuild pipeline coverage. A Significant Actionable Item from this Podcast Audit your pipeline and calendar before changing the goal. Identify every active opportunity, mark which deals have clear next steps, remove or deprioritize poor-fit opportunities, and block time this week for prospecting, referral requests, outreach to past customers, and networking. Do not rely on optimism. If an opportunity does not match your ideal customer profile, lacks buyer commitment, or requires too much customization to win, it is likely stealing time from better revenue-generating work. Summary This episode is a timely midyear inspection for any B2B salesperson, VP of Sales, business owner, or sales management leader who is trying to protect the second half of the year. Kevin and Sean make a clear argument: missed goals are not solved by pretending the number changed. They are solved by stronger qualifications, clearer commission plans, better time allocation, disciplined sales processes, and more honest pipeline review. If you are behind, ahead, or unsure where you really stand, this conversation will help you decide whether you have a quota problem, a planning problem, a pipeline problem, or a leadership problem—and what to do next.
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