
Two Tall Guys Talking Sales · 2026-06-30 · 20 min
Key moments - from our scoring
Substance score
37 / 100
Five dimensions, 20 points each
Kevin Lawson and Sean O'Shaughnessy directly challenge the impulse to reset quotas mid-year when a sales organization falls behind plan. Instead of lowering targets, they systematically examine pipeline quality, deal prioritization, prospecting discipline, and time allocation - the real levers that determine second-half performance. They acknowledge one narrow exception: when the executive team built revenue assumptions into the plan (a new product launch, acquisition, or strategic initiative) that failed to materialize through no fault of the sales team. In that case, resetting is appropriate to reflect unavailable opportunity. For sales leaders and individual contributors facing shortfalls, the episode walks through practical diagnostics: rationalize your pipeline to remove misaligned deals, qualify out deals lacking clear next steps, reconnect with past prospects who chose competitors, protect prospecting time by auditing your calendar, and delegate non-selling tasks that consume energy. Whether ahead or behind quota, the conversation applies - those performing well must continue filling the funnel to avoid pipeline collapse next year.
No, the quota should remain fixed unless executive leadership failed to deliver a strategic assumption built into the original plan (like a product launch or acquisition). Resetting the goal downward creates a cascading problem - miss the lower target and you've lost leverage. Instead, audit pipeline quality, qualification discipline, and prospecting time allocation to find where execution broke down.
Reset the quota only if the executive team built revenue assumptions into the plan that never materialized - such as a new product ready for sale, a company acquisition, or a strategic initiative - and this failure was outside the sales team's control. In that case, remove the unavailable revenue from the salespeople's targets to reflect what they can actually pursue.
Rationalize the pipeline by removing deals that are misaligned with your core offering, deals without clear next steps, and deals where prospects have made other choices. Reconnect with past prospects six months out to see if their other solutions failed. This qualification discipline frees time to focus sales effort on winnable, high-fit opportunities.
Time allocation varies by organization and available resources (BDRs, SDRs), but every salesperson must protect prospecting time by auditing their calendar. Color-code activities to track how much time goes to prospecting, customer work, and retention. If you claim you have no time to prospect, map your activities over a month to identify low-value time (coffee breaks, unnecessary status updates) that can be redirected to pipeline development.
Continue prospecting and filling your pipeline aggressively. High performers often exhaust their pipeline by staying busy closing deals and forget to develop new opportunities, creating a roller-coaster effect in future quarters. Allocate consistent time across all stages of your sales process, from prospecting through retention, to sustain growth beyond the current year.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode delivers a few useful operational points - particularly the CEO planning failure exception as the only legitimate grounds for quota reset - but the runtime is diluted by sports analogies, repetition, and generic advice about prospecting and calendar color-coding. Insight-per-minute rate is low for a 20-minute episode.
if you thought something was going to happen and you put it into your plan that you were going to buy a new company or a product was going to come out onto the market and you were going to be able to sell that product this year and that product didn't materialize for reasons, not because of the sales team. That means you made a mistake in your plan at the CEO level.
plan for 120% of the goal. Because if you miss 5, 10, 15%, you still plan to exceed goal
The core thesis - don't lower quotas mid-year - is conventional wisdom, and the supporting content recycles familiar sales-coaching tropes. The CEO-accountability-vs-sales-execution distinction is the one genuinely non-obvious framing, but it is not developed into a rigorous framework.
the net didn't get bigger, the net didn't get smaller. He didn't get to put two goalies inside the net. None of that stuff happened. You just didn't get the ball on the net.
Microsoft says PTEP, uh, plan to exceed plan
Both hosts are working sales consultants with active client rosters, giving them legitimate practitioner credibility. However, they are SMB-focused coaches rather than executives who have personally scaled large sales organizations, and they host their own show, which slightly inflates their platform relative to their demonstrated seniority.
Some of my clients, and this is not a best practice, it's just reality of where they're at, did not set goals. At the beginning of the year.
One salesperson said, uh, I look at the spreadsheet that the controller sends me before he cuts my check, and I go, that must be my comp plan.
The episode is almost entirely abstract advice and hypothetical scenarios. The only named company reference is a passing Microsoft PTEP mention, and qualification methodologies (MEDDIC, BANT) are namedropped without illustration. No revenue figures, conversion rates, client outcomes, or concrete timelines are offered.
Microsoft says PTEP, uh, plan to exceed plan
whether it's med pick, Bant Spice, Y Y Ah Y There's tons of qualification methodologies out there
The co-host format produces mostly sequential agreement rather than genuine interrogation; the one substantive pushback - Sean carving out the CEO planning-failure exception to Kevin's hard 'never reset' rule - is the episode's best moment of craft, but it is not pressed further or stress-tested with examples.
I, uh, completely agree with everything you said with one small. I don't believe you should reset your goal...Except for when you acknowledge as a leader of the company that you didn't know what you were doing.
I really like this, and I think I want to go deeper on this because I think the biggest value this community can get from us is, you know, how would we solve that problem?
Computed from the transcript - who did the talking, and the words that came up most.
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.
Transcribed and scored by The B2B Podcast Index.
Speaker A: Mid year is when sales goals stop being theoretical and start exposing the strength or weakness of the sales organization. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean o' Shaughnessy challenge the temptation to reset quotas simply because the team is behind. Instead, they focus on the harder questions. Is the pipeline real? Are the right deals getting attention? And is prospecting being protected? Before the second half slips away, listen in for a practical conversation on quota discipline, pipeline prioritization, and the sales management decisions that determine whether the year can still be won.
Speaker B: What's going on in the world of setting goals for all of the second half of 2026? We're right here at the straight up and down point of the middle of the year.
Speaker C: Some of my clients, and this is not a best practice, it's just reality of where they're at, did not set goals. At the beginning of the year. They weren't my client at the beginning of the year, they. They did not set goals appropriately for everybody. And at the beginning of the year, in one case, they didn't do commission plans. But once again, another, not a best practice. So this has been a bit of a rush for me because I'm like going, okay, you didn't do it then. So the salespeople, uh, all kind of think that they know what their goals are in those companies. However, they're not quite sure. One salesperson said, uh, I look at the spreadsheet that the controller sends me before he cuts my check, and I go, that must be my comp plan. So I know how to work my comp plan and, you know, do what's important to my company because of how he's paying me. And I go, that's good for you. You figured out part of the process. But let's put that down on paper so you don't have to do that analysis to make sure that we all agree that that's the right one. Very few people in life are perfect. You didn't get it done at the first of the year. You didn't get it done because you didn't know it was important. But that doesn't mean you can't do it now, right? And maybe July 1st is going to be a little bit of a stretch if you haven't done it at all. But you can get it done by July 10, right? So let's go ahead and catch up. Let's go ahead and do the right things. Or like Kevin says, the Kevin is something that actually I say all the time and I give him credit for is let's do the easy things well. And uh, one of the easiest things to do is just write down how are we going to pay you? I mean, it seems like a really honest and good thing to do. So what do you think, Kevin?
Speaker B: Sean and I are both members of other round table think iron sharpening iron organizations. So I was, you know, looking for sales insights there. So leaders are readers. So I was reading other content so I could be more informed about other things going on in other industries and geographies and whole nine yards. And what I'm seeing is a common thread and this is one that every salesperson and business owner should dogpile on. You should really lean into this. Here we are mid year. There's a lot of people that are now searching for coaching. Think EOs, implementers, you know, business coaches, focal point, one of the other brands, action coach, as well as revenue turnarounds, I. E. Performance marketing companies, people thinking about what are we going to do to catch up for the rest of the year? Or what are we going to do to systematically plan for 2027? Sean and I are famous for saying, hey, if you've got a long sales cycle, 2026 might already be cemented for you. If you don't have enough prospects and pipeline coverage, you could be looking at a 2027 issue and just survival until then. But that doesn't exempt you from thinking and doing and planning and acting. So I'm seeing and having a lot of conversations about people who are behind goals. Uh, either my price, they're my prospects now, or they're ahead of goals. Hey, how are we going to deploy this future ar? Is it going to be for reinvestment in the business growth, the whole nine yards? One of the most interesting conversations I've had recently, Shauna, and I really like this is somebody came to me and said, hey, we're way behind. Should we or should we not reset goals mid year? And I think that's a relevant discussion because some people are with their you're below or ahead of goal. The discussion is the same. If the goal was 10 million, should it be 12 or should it be 10, 5? Or should it be? If you're trending towards 8, should you keep 10 or should you trend towards 8? And my pad answer for all of these is you never adjust the goal. The reason you never reset the goal is because your job as a salesperson is to hit the goal or your quota. And if you don't have the trend line to get there, it's a problem. You have to Solve. So I was talking to this executive and uh, he says well, should I go reset my goals? And I said no, you should actually plan for an increase. And I said, because if your goal gets reset down, what if you miss that one too? You have six months left. Regardless of the climate of your sales environment. I don't care what industry you're in, if you're in construction sales, if you're in technology sales, if you're in professional services sales, you have a leads problem. If you're behind, you have a leads prioritization problem if you're ahead. So you've got to staff or adjust or strategize subordinate projects. Cancel projects to get to the goal. Now this is where salespeople and financial controllers, uh, and CFOs get, get into each other's ears because somebody might say we need to trend down. Staffing, spend, headcount, travel, you name it. Sales leaders say, oh hey salespeople, it's really time to, to double down on your efforts. This is a great time of year to talk about qualification. How do you get out of bad deals faster because you need that time back to go find better deals. Are you networking? Are you calling past customers or what are you doing? So the goal setting this time of year is a really current poignant conversation for everybody to have. And if you ask me in public as we're walking down the street into a networking event, I'm going to say don't reset the goal. If anything, I'm going to steal one of Sean's lines. Here is plan for 120% of the goal. Because if you miss 5, 10, 15%, you still plan to exceed goal. Microsoft says PTEP, uh, plan to exceed plan. There's other organizations like that. When you're doing your qualification methodology, whether it's med pick, Bant Spice, Y Y Ah Y There's tons of qualification methodologies out there. Make sure you're doing the easy stuff. Well, I love this conversation. Sean, if you're a seller out there and you're behind, I want to encourage you to go to your marketing department. Make sure you're deploying digital assets that return conversations. So you've got one leg of your stool built asking for referrals. What's going well, who else do you know? Who else should I know that's in your network? Where are you networking that you're getting good value out of? All of these conversations are ones you can have now but before the end of the week that will return value to your business for the rest of this year.
Speaker C: I, uh, completely agree with everything you said with one small. I don't believe you should reset your goal. I don't believe you should bring it back down. I don't believe any of that stuff should be the case. Except for when you acknowledge as a leader of the company that you didn't know what you were doing. If you thought that something was going to happen in your industry, in your company, in your customer base that was going to make revenue go faster, better, quicker, bigger, and you built that into your plan and then that thing did not materialize. And it should be an additive thing, but if you thought that something was going to happen and you put it into your plan that you were going to buy a new company or a product was going to come out onto the market and you were going to be able to sell that product this year and that product didn't materialize for reasons, not because of the sales team. That means you made a mistake in your plan at the CEO level. So, so the CEO is allowed to say, I screwed up now. Uh, it's not a happy thing when the CEO says that it's not a good thing. However, you are now penalizing the rest of your company because you thought something was going to happen at the CEO level, at the executive level, and it didn't happen. You didn't do your part by bringing that to the company and bringing that to the organization to sup. So in those situations, and only those situations, I am okay with saying, okay, let's be realistic. That product is not ready to sell in this period and we thought it was. So let's take that out of the plan for the salespeople and let's adjust it accordingly. Not that the salespeople were missing their goals, but the salespeople can't make their goals for things that are outside of their control. So I'm okay with a pullback for that reason. And that reason only when you played football, they didn't say, well, we'll give you a point when you get to the 20 yard line, uh, you get zero points when you get to the 20 yard line. If you only go for the 20 to the 20 back and forth, back and forth, you don't get any points. Right now the World cup is going on. It's been a lot of fun to watch the games in the same time zone that I sleep in. And so. But you only score points in soccer or European football. You only score points for putting the ball in the net. You don't get a score point for anything else. So, no. And the net didn't get bigger, the net didn't get smaller. He didn't get to put two goalies inside the net. None of that stuff happened. You just didn't get the ball on the net. So therefore, no, that's the game you're in. Therefore, you don't move the goal, you don't move how we score the game. You don't move how we score your quota, we don't move how we score your commission.
Speaker B: I really like this, and I think I want to go deeper on this because I think the biggest value this community can get from us is, you know, how would we solve that problem? So I'm going to start out and say, let's do the simple things well. You've already said it once. Thank you. Slow is smooth and smooth is fast. This is why, uh, that's another way of saying, do the simple things well. So we are also going to take an intellectually honest approach to our pipeline. So if you're a seller out there and you're behind or you're a seller out there and you have a ton of business we have to go through and prioritize. It's the only time this doesn't apply is when you have zero deals in your pipeline. We'll get to that later. But when you've got deals in your pipeline, you got to figure out which ones are aligned and which ones are not aligned to what you do. So if somebody says, hey, Sean and Kevin, would you like to take on a marketing engagement? Could we m. Maybe a little bit, but not very well. That's not our core center plate kind of work. But if we have something like that in our pipeline or you have something similar in your pipeline, now's the time to go and look at that and say, I'm going to have to spend too much time, effort, calories on this project. That means I'm gonna have to build something from scratch because I probably don't have it just sitting, waiting to deploy. I, um, have to do a lot of things to execute on that type of scope of work or to sell that product. This is where we have that rationalization to say, I'm not gonna focus on that. Yes, there are dollars attached to it. They could even be big dollars. Just like we have to decide as small business owners or sellers inside of large organizations what is it that we do, what deals in my pipeline align the best, because that's what my team or product or solution is designed to perform and solve problems. That way we can be more competitive and not have to stand on our ear to get to the right deal. So rationalize. Rationalize your pipeline and then figure out which deals don't have next steps. What steps are not clear, and it's okay if Sean's a prospect. It's okay if I don't know the next step for me to call and say, hey, Sean, we talked a few times and we started developing scope, but we really don't have a clear next step. And then you prescribe a next step. Typically, the next step would be an A, B, C, D. And then we would do E, F, and G. Like, you start to prescribe the next steps in the sales process. And if your prospect says, that's not really what I want to do next, that's also a deal that's not qualified. You don't get to continue to add time to that deal. So qualify your deals. If you've got deals in the past six months that have gone away. Sometimes people make a decision, that decision goes poorly, and they don't really want to, you know, fall on the sword and call you back, say, hey, that other provider that I selected because of price instead of you, it didn't work out so well. They might not do anything, or they might go look for other people to provide the solution that you can provide. You can call back and say, hey, Mr. Business Prospect, it's been six months, and I know you didn't select me, but did that project go okay? Is there still an opportunity for us to have a discussion? I don't want to keep doors closed that could be open. It's purely sales behavior. It's reaching out and touching people who are in your ideal client profile and of the Persona that can make a decision, and then you advance the deals. Now, there's also the other piece of the puzzle, which is what Sean and I do a lot of, which is networking. If you are. I'm using my air quotes here. So busy that you don't have time to network. You have time to network. You have to figure out what is not important on your schedule. So color code the appointments on your calendar, make it visually insightful to say, what's prospecting, what's customer work, what's customer retention work? If you're behind, you certainly can't have deals go away or customers go away. You can't have churn or attrition. So I. All these things are just some things you could do tactically to advance your pipeline.
Speaker C: John, if you are 110% of quota and you are Just kicking it, like deals are just happening and happening and happening, then one of the mistakes you can make is not prospecting, not filling up that funnel, because by nature of you're just kicking it and deals are happening and you're closing deals, you are exhausting your pipeline. And we've seen this happen before. Every sales rep probably has seen this, but definitely Kevin and I have seen this where, you know, we were so busy selling that we forgot to sell. And the reality is that causes the roller coaster effect and whatever. Every salesperson has to spend some time developing their pipeline. Now, that might be different depending on the size of your organization, how many resources you have available to you. You might might have BDRs or SDRs available to you to fill some of that pipeline up, in which case you start with discovery and not for, you know, prospecting. That's fine if that's how your organization is set up. But you have to allocate enough time at every step of the process. And if you think about that, there's various steps in those sales process going from I just met the person to the person now is my best customer. That that continuum of ideas and activities and actions, they each take a certain amount of time. And as a good time management tool, you should be thinking, how much time did I spend on each one of those phases this week? Not today, because today may be a closing day, or today may be a prospecting day, or anything in between, but this week, definitely this month, I encourage salespeople to say, I don't have enough time to do X, to say, well, let's map it out over the course of a month. Can you find the time over the course of the month? And yes, that may mean that we're going to spend a little bit less time drinking coffee with the buddies in the break room, but you need to look at every block of time that you have available to you to say, can I actually do it now? You also need to make sure that you are appropriately giving other people things to do. There's nothing worse than a salesperson walking into the office and then immediately running around to all the project managers and saying, give me a status update on how we're doing on that deal. Is that your job? If it is, okay.
Speaker B: But I don't think that it really
Speaker C: is, because do you get paid? Does your commission go up when the projects get finished? Then you have to be involved in that process. But you should not be involved in every step of every thing in the process. You cannot do it all and expect to grow so you need to be able to delegate. You need to be able to think about your delegation skills. So these are some of the conversations I have with salespeople about when they say I can't prospect, I can't network, I can't do these things. Well, where are we spending time? What are you doing on a regular basis? And then just dig into it, start tracking it down. What can I squeeze out? How can I constantly be busy? You need to cut those out, diminish those as much as possible so that you can get on with a, uh, productive day and do the things that are important. And then you'll have time to prospect, and then you'll have time to do a good job of discovery and then you'll have time to do a good job of scoping because you're always going to, you're always going to have time to figure out how to close because you're going to prioritize it above all of the other stuff. We just have to kind of move the prioritization of the stuff that's not a fun prospecting to higher than spending an extra cup of coffee, shooting the whatever with the buddies in the office.
Speaker A: What a Especially for any sales leader staring at the second half of the year and wondering whether the number, the pipeline or the operating discipline is the real problem. I learned a lot from Kevin and Sean's discussion about the rare exception to keeping the original quota in place when the executive team built the plan around an assumption that never became real. That is an important distinction because salespeople should be held accountable for selling, but they should not be punished for a product launch, acquisition or strategic initiative that leadership failed to deliver. The technique is simple but not easy. Poor sales execution is not the same as poor executive planning. So deal with them separately, then make the adjustment only when the missing revenue was never actually available for the sales team to pursue. Your significant actionable item from the this episode is to audit your pipeline and calendar before you even think about changing the goal. Look at every deal, every next step, every bad fit opportunity, and every hour on your schedule because lost time and weak qualification quietly kill the second half of the year. Do that today, before the rush of customer calls, internal meetings and daily distractions can be convinces you that vague optimism is a plan. If you need help with sales, sales management, or simply growing your company, reach out to Sean or Kevin using the contact information in the show notes. You can also join the B2B sales lab, a uh, community of salespeople and sales leaders who help each other answer real sales questions, find better resources and make quota with more discipline. We will be back with you next Tuesday, Tuesday afternoon at 4:30 Eastern. And until then, happy selling.
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