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Two Tall Guys Talking Sales Podcast: Why Should a Company Assess Its Practices in Sales?

Two Tall Guys Talking Sales Podcast: Why Should a Company Assess Its Practices in Sales?

In this podcast, Kevin and Sean discuss why it is important for companies to assess their sales plans and processes. They explain that having a sales plan is about more than just setting quotas and involves figuring out how to bring value to the customer. It is also important for smaller businesses that are transitioning from founder-led sales organizations to have an assessment to build the right infrastructure. The conversation also touches on how CEOs should still be involved in customer conversations regardless of company size and that competition, complacency, and consistency should all be considered when assessing one’s own organization. Lastly, they invite listeners to reach out with any questions they may have about creating a great sales organization.

You can subscribe to our podcast by searching in your favorite podcast player for “Two Tall Guys Talking Sales,” or you can listen to the embedded version here.

The following is a transcript of the podcast above. It has been sparsely edited to increase its readability, but many of the idioms and poor spoken grammar have been left in place. automatically generated the transcription, and, as capable as that product is, there are times when words are missed or the sentence structure is incorrectly interpreted. We have tried to catch all of these software misses, but we are confident that some still remain. The below text is provided for those that would rather read than listen to a podcast.


Kevin Lawson

Hello, and welcome to Two Guys Talking Sales. I’m Kevin. 


Sean O’Shaughnessey

And I’m Sean. 


Kevin Lawson

We’re glad you’re here. In this podcast, we’ll tackle real sales issues big and small for salespeople selling situations and sales leadership. We’ve collectively built successful careers around the problems and solutions used in B2B selling, from software to services, manufacturing, and distribution. We have sold to and for many of the world’s most recognized brands as well as some you’ve never heard of. For roughly the next 15 minutes, we invite you into our world of experience, where we’ll take one issue and dig into it so you might have a solution for when you encounter a similar situation in your career. Let’s dive in. Sean, what are we talking about tonight? 


Sean O’Shaughnessey

Kevin, we should discuss why a company should assess its sales plan, process, and methodologies. How about that? 


Kevin Lawson

Sounds Good. Maybe we should start by asking, “What are a sales plan, system, and methodology.”


Sean O’Shaughnessey

That makes sense to me. Do you want to start? Go Ahead.


Kevin Lawson

Let’s start from top to bottom. Having a sales plan is more than just a quota. A sales plan is how you’re going to market. It’s a marketing and sales plan. It’s not only who you’re talking to but why are you talking to them. What value are you bringing to the table? 


Sean O’Shaughnessey

It’s figuring out what your roadmap is. Are you going straight there? Are you going around the curves but figuring out in advance what you will do? How are you going to get there? What’s your plan for success? If you’re really good, I think it’s also, “what’s your plan for avoiding failure?”


Kevin Lawson

Let’s put ourselves in a business owner’s or sales leader’s shoes. We’ll walk a mile in their moccasin, so to speak. We think we’ve got a good sales organization already. Why should we assess what we perceive as a good organization? 


Sean O’Shaughnessey

Let me make my case here. I would challenge almost every company that thinks they have a good sales organization if they are small. You can defend it, or you can go against it. My case is if you are a small company selling a product nationally, definitely internationally, let’s say nationally, just the United States. There are very few products you can sell that anybody’s buying that aren’t going to buy at the national level at the 500 million to a billion dollars worth. Suppose you’re trying to sell your product or service nationally. In that case, you are going after a 500 million to a billion dollar or a $10 billion marketplace. If you’re still a small company, a company under $20 million or under $30 million, you have a 0.1% market share. Your organization isn’t operating as well as it possibly could. It needs to operate better to grow fast and go after that market. I don’t know. 

What do you think, Kevin? 


Kevin Lawson

I like that line of thought. I don’t really see the need to go point-counterpoint here because I think the value here is saying, “what have we seen in our careers that would support our answers?” Even if we drop a couple of zeros off our target markets or the market cap, right. Even if I’m a $20 million, $10 million, or even smaller company, the idea that I’m at my peak is a fallacy of best. Nobody’s at our peak. The moment we stop learning, the moment we stop trying, is the moment we start failing. 


Sean O’Shaughnessey

I agree. 


Kevin Lawson

Why have the practice? I firmly believe that if you aim for nothing, you will hit it. Right. You need to assess where you are, where you’re going, and how to get there. Plan your work plan. Work your plan. We’ve probably all had a mentor in our life who said, hey, plan your work. Work your plan. If you don’t have a goal, you’re sure to hit it. 


Sean O’Shaughnessey

I agree. That’s part of why you should assess yourself because you should say, well, how am I doing against best practices? How am I doing against the metrics of somebody really cooking on all cylinders? Right. That’s why you should do an assessment. You should go after markets and best practices that make sense for you and say, gee, what are the leaders doing in my market? What are the best companies doing? And then say, am I fulfilling those? Am I better than they are? Or do I have room for improvement? What are those things that I could improve? 


Kevin Lawson

I would also add that this is a yes and not a yes statement. The yes and statement there is that the value we bring to the market as salespeople is solely perceived by our clients. That’s the measuring stick. In most cases, if not all, our clients or prospective clients are looking for us to bring value to them. Suppose we need to assess how we’re doing it or how we could do it better. In that case, we’re actually decreasing our value market. Every good ending begins with a well-planned beginning. 


Sean O’Shaughnessey

If you do stop improving, if you do stop trying to improve yourself on a daily, weekly, or monthly basis, then you’re going to go start going back. The market doesn’t stop. The market exists, and your competitors are going after that market. If you’re not trying to do better, they will eventually beat you, and we don’t want that to happen. 


Kevin Lawson

Let’s take the other side of that coin. We started by asking, what about the person who thinks they’re doing well already? What about the smaller business, the solopreneur of sorts, or this really small business that’s emerging and they’re a founder-led sales organization. My first point as to why they should have a system or assess their sales organization is because they’re going from selling themselves to sales management kind of at the same time. They need to assess what they are doing and what they want others to do in their organization. It’s about building an organization instead of scaling or growing up in its business. 


Sean O’Shaughnessey

My first thought is, where do you want your company to go? I was talking to a company owner just yesterday, and one of the questions I was asking her was, where do you want to be in five years? Where do you want to be in ten years? What do you envision to be your future? Suppose you envision your future to be that you’re a manager. In that case, other people are doing all the work, and you are making them better as individuals, a team, and an organization. But that’s your job. You’re divisionary in this organization. Why are you waiting to start that process? Why are you doing everything now and then? What do you think will be some magical switch you will flip? Okay, now I get to be a manager. Right. I believe that the process of thinking about “Where do I want to be?” and then making my plan so that I’m actually moving forward. is an important part and goes back to being a sales plan and a marketing plan, and a company plan. 


Kevin Lawson

If it’s okay, I’d like to lean in on that. You said you talked to a business owner about that. We get faced with this a lot when we have these discussions. It’s not in theory like we’ve moved off of theory into actual leadership for businesses. What was the next step in her mind and your mind? 


Sean O’Shaughnessey

Her next step was truly understanding what she wanted to be in five years. Her first answer was, well, I want to sell the company in five years. And I was like, oh, that’s interesting. Great goal. That’s your goal. What are you doing not only in sales to make sure that the company can grow, but now if you want to sell your company, are the other portions, the operations portions of your company, actually working? I think I scared her just because I think she was counting the months between now and five years and realized that she didn’t have a lot of time to get all those things in place. By the end of the conversation, she said maybe seven years, which was an interesting realization. It was just a matter of what have you done to make yourself sellable? 


Sean O’Shaughnessey

I did remind her, though, that anything that she is doing as the owner of the company, if she wants to step out of the company in five years, means that she needs to be able to delegate all of those things as soon as possible because she needs two or three years of run rate with that management in place for that potential buyer to say, that makes sense. It’s all worth that. You leave, that’s all good, and I’m going to keep the rest of your team in place, and I’m going to make it better with more resources. She was a little scared because she didn’t think she had everything lined up and ready to go in just one or two more years. She was going to have to be there. That was what was scaring her buckle in seven years. 


Kevin Lawson

That’s a great point to really hammer on. It takes infrastructure and planning to get to the ‘sell number’ you want to get to. For all the salespeople, regardless of your role or stage in your career, some of the best sales discovery calls don’t end with Kylie. You’re exactly right. That’s exactly what I need. Some of the best sales calls and our best values are when our prospects say, or our customers say, I’ve never thought about it like that, but you’ve got me thinking in a different direction. Right. We’ve added value to that discussion. I had a similar discussion, but not the same. It didn’t come out like that. It didn’t come out with the owner saying, hey, I want to sell the company. It was really the thinking through of what do they want to do? They said, “I don’t want to sell the company, but I don’t want to do all of the business development networking.”

And so similar discussion. It’s funny how parallel our lives are when we’re talking to businesses because there are so many problems that are very similar, right. All you tell people out there listening, note that whatever you’re talking to about your customers or your prospects, somebody else is probably having that same conversation. I digress. Anyway, I talked to my customer, and he said, “I really don’t want to do the business development anymore.” I said, “what does that really mean? Does that mean you want to get off a plane? Does that mean you want to not do as much prospecting or networking?” He said, “no, I don’t want to do the initial discovery and demo anymore. I really want to focus on showing up as the voice of the founder to close the deal. We’ve worked up the deal and scope to where it makes sense for the business.”

We made the business case. I said, “we know that’s a really interesting problem because many people have that issue.” That will relate to why you assess your sales team. 

Why assess the sales organization? Because you want to take it to a place where you’re still determining what that end game looks like. Defining that is the whole reason for the assessment. With that founder, we arrived at an idea of how to build a sales organization around him, being able to do the center plate work that he wants in three years. Development teams, sales enablement teams, and demo teams. To get to the point where the scope was finalized, he could go in and really drive home the value for the company. 


Sean O’Shaughnessey

You and I have both worked for some fairly large companies. Even in our history, working for some Fortune 500-type companies, it was common for a major customer to want to speak to executive staff, right? Maybe not the CEO, but probably the president, perhaps the CFO, whatever, and have a conversation about the future of their company because how is that aligned with the future of the customer’s goals? It’s okay for a founder to say, look, I don’t want to do all of the day-to-day sales activity, but that doesn’t mean that the founder should ever feel like he will be divorced entirely from sales and never see a customer again. Because even in some of some 500 million dollar companies that you and I have both been part of, in my case, I was actually part of a $14 billion company. That CEO met with customers. 

That’s not an unusual thing. It’s not about closing the deal. It’s not about even building the case to close the deal. In that case, it was about, “This is where we’re going as a company. How does that align with you, Mr. Customer? Do you want to go in that direction as well? And let’s talk about the future together.” And those were the conversations. I don’t care if you’re a $2 million or $2 billion company. That’s the reality of life that CEOs will always be front and center in the conversations with those key customers. The key customers are different in size and scope. 


Kevin Lawson

I’ve got a favorite phrase. When it comes to the size of companies, and you can appreciate this, at the end of the day, you can either add or drop zeros. It’s still dollars and products and value. If they don’t see the value at $10,000, they won’t see the value of $10 million.


Sean O’Shaughnessey



Kevin Lawson

Add a couple of zeros, and it’s still about the value you bring to market. 


Sean O’Shaughnessey

Exactly. In fact, you know what? The customer still has to get an ROI on that investment. That investment they make in your product has to be better than the investment they’re going to get from the local banker or any other investment they’re going to make in their company. Right. Every company is looking at what’s my internal rate of return. They may not use those words, but they’re still looking at this investment; this thing I’m buying is more valuable than the other thing I could be buying with those same dollars. 


Kevin Lawson

Well, hey, we’re coming up right on 15 minutes here. That’s what we promised. We’re going to over-promise and not under-deliver. We will over-promise and over-deliver because that’s what we do in sales. Quick hits here as we’re wrapping up here. What is the biggest takeaway just from this conversation for you tonight? 


Sean O’Shaughnessey

For me, you need to benchmark yourself against those premier companies you’re competing with. You may not even be competing with them, but premier companies in your orbit that are right in your surroundings. That’s what a sales assessment is all about. 

What about you, Kevin? What do you think? 


Kevin Lawson

I completely agree with that. For anybody out there listening, I hope you wrote that down. That’s a really great takeaway. Know who’s in your orbit. It’s a great phrase for me. It’s why I have a system. It’s so that you will know where you are in your journey. You need to be able to look ahead and behind the trees and know that you have moved off the starting blocks toward the goal.

If I had to summarize, it would be the three Cs: 

  • competition, 
  • complacency, and 
  • consistency. 
  • Competition is what’s coming at you. 
  • Complacency is what’s up here. It’s in our gray matter. 
  • Our consistencies are what our clients see. That’s what they want and what we’re trying to avoid. It’s that complacency in our sales lives. 


Sean O’Shaughnessey

That’s a great point. Let’s talk about our series that we will be doing to make sure people have some idea of what’s going on. 

We will do these every week for about 15 minutes per session. Maybe more, maybe less. We won’t hold a stopwatch against us, but every Tuesday is our goal. We want to do it right at the end of the day. So 4:30 PM. Look for it on your LinkedIn feed about that time. You’ll be able to watch it after the fact, obviously, as well. We’re going to start with many questions we would ask if we were assessing your company. A bunch of questions that we have built into your system that we’re going to ask. We will talk about the value of those questions, but we really want your questions. What questions do you have with Mr. Listener and Mrs. Listener? What questions do you have about sales in your company, about how to create a great sales organization? Drop them in the comments. Reach out to Kevin on LinkedIn. He’s always on LinkedIn. Reach out to me on LinkedIn. I’m always here as well. We’re connected to this podcast or this video. Just ask us some questions, and we’ll bring them up. In a future episode, we might tag you and say, hey, this was Joe that said this. This was Steve that said that. We would like to hear from you about what is important to you and what questions we can answer. 

Anything from you, Kevin. 


Kevin Lawson

Happy selling! Sales is a journey. It’s okay to make a mistake, but it’s not okay to not do anything. 


Sean O’Shaughnessey

I agree with that 100%. I agree with that. 

I will end with my favorite quote from a sales trainer. It’s from Zig Ziglar. He was famous for saying, “stop selling and start helping.” We’ll talk about that in a few future episodes. I think we’ll do a whole episode on that very topic, but that’s one of my favorite quotes. 


Kevin Lawson

Hey, Sean, remember to tell them what’s coming up next. Our next question on how to determine a company’s sales objectives. 


Sean O’Shaughnessey

Next Tuesday at about 4:30 PM. We’ll have it scheduled out there. We’ll catch the comments; send us a note, and we’ll catch those as well.

Thank you very much for your time. We look forward to talking to you and hearing what Kevin and I say about that topic. And once again, drop a comment. 

Thank you very much for your time. 

Thanks, Kevin. 


Kevin Lawson

Thanks, Sean. 

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