The Essential Sales Management Checklist for Small Business Owners

:: 00:00:00

Speaker 1

When I hired my first salesperson as a business owner, I made a huge mistake and it cost me sales. And the worst part is I knew better. I've led national sales for the U.S. Chamber of Commerce. I've run field sales teams. I've run direct mail sales teams. I've turned around eight sales teams in my career. I've helped hundreds of people as a coach, as a consultant, as a fractional operator, go in and scale up their revenue.

:: 00:21:06

Speaker 1

So I know a thing or two about sales management, and I still dropped the ball in this area. If you're a business owner with one, two, maybe three salespeople and you're not getting the performance that you want out of them, chances are you are making the same mistake.

:: 00:37:15

Speaker 1

Hey. What's up? I'm Ray green, former executive turned nomad entrepreneur. In my sales career, I have turned around eight sales teams. I led sales for the national U.S. Chamber of Commerce. So basically everything small and mid-sized business outside of D.C.. And I meant direct mail sales and field sales and call centers. And I've led sales turnarounds as a CEO for investor groups.

:: 00:56:01

Speaker 1

I've coached and consulted hundreds of a B2B businesses and IT businesses and helped them scale up their revenue and their sales team. So you could say, I know a thing or two about sales management, but when I hired my first salesperson as a business owner, it was a completely different ballgame because I was strapped for time. I felt like, you know, person with six arms, like I'm doing everything that I possibly can.

:: 01:15:22

Speaker 1

The reason I was hiring a salesperson was because I couldn't manage that sales process. So when I made that hire, what happened was I onboarded properly and I had a decent playbook, but then I just absolved myself of basically all of the sales management functions that I should have been doing, and frankly, that I knew I should have been doing, because that's been my career.

:: 01:32:24

Speaker 1

I understand how applying your time into different things, into training and development, into meetings, into call reviews and coaching and all the other things I understand, and I have seen firsthand how that can and will drive more performance, more accountability, better execution of your sales process. But it's not like as a business owner, I couldn't keep up with it.

:: 01:50:12

Speaker 1

Right? And so it was easy to skip a lot of the things that I knew I should have been doing. If you are not performing your job as a sales leader, as a sales manager, which you are, if you have any salespeople reporting to you, doesn't matter what your title is of its CEO, of its founder, of its VP of sales, you are a sales manager.

:: 02:07:17

Speaker 1

If you have a salesperson reporting to you, and if you are not doing the essential things, then you can't expect a good performance from good people for any sustainable and reasonable period of time. So I know if I made this mistake as a veteran sales leader and knowing what the fundamentals are and what the essentials are, that a lot of business owners are doing the same thing.

:: 02:28:23

Speaker 1

So I recorded this video to break down what is basically a lean sales management guide. These are the crucial things that if you do these, you will get maximum leverage on the time that you invest with your sales person, with your salespeople. It will lead to more sales performance from your salespeople. It will lead to more clients, and it will lead to more money in your pocket.

:: 02:49:21

Speaker 1

So I'm going to go through what these things are. And if you're in business owner thinking, how the hell am I going to get these things done? Like if you look at my schedule, I get it, I hear you, I'm a business owner to stay to the end and we'll talk about that as well. But you need to know what the minimum requirement is here to be a decent sales manager and get that performance in the first place.

:: 03:07:08

Speaker 1

And then I'll share a couple of ways how you can tackle that, even if you're limited on time. Now, the first thing you've got to do is a minimum requirement to be an effective sales leader is run a sales meeting every single week. And I like doing these on Monday because one of my sales mentors said, like, that's the best time to like basically shake out all the cobwebs, you know, from that from the weekend.

:: 03:22:28

Speaker 1

It helps accelerate the start to the week, like a lot of people come in and kind of like want to get a low ramp and are recovering from, you know, Sunday Night Football or whatever it is. You have a meeting and you get some energy in the room and you go through the numbers and you maybe do something inspirational, share some training, do have some fun, play a game, whatever it is, but just get the place moving.

:: 03:41:28

Speaker 1

You get people focused. You talk about accountability. You talk about the goals. Are you going to do all that? Do it early, and then you set up the rest of the week for your best opportunities. Now, if you're not sure how to run a weekly sales meeting, here's a quick agenda. I like to start with something that is intention.

:: 03:55:28

Speaker 1

Or when it comes to getting some engagement or getting some energy. And it depends on what kind of tone I want to send, right? If we are crushing the numbers and we're doing really well, and my biggest concern is God, I don't want to think like we're we're too far ahead and start slowing down. Then why I may do is like, grab a video on YouTube and search for something like, you know, the the well, they're racing like in the Olympics.

:: 04:17:25

Speaker 1

And one person kind of slows down and somebody blows past them or something like that. Like I'm going to find something that's themed around what I want, okay? If the team isn't performing, I have a way behind on numbers. I may come in and inject a very different kind of energy. If you've got core values, you can get something started around an activity or a game or something around like don't make it super cheesy, but get some engagement and be intentional about the type of vibe and the type of energy that you're going to want to inject into the team, and whether that's going to be a, hey, we've got to go get it, whether

:: 04:46:21

Speaker 1

it's going to be a little bit of a cheerleader, whether it's going to be, you know, basically a call to action like, hey, this is like an oh shit moment. We, we got to get back on pace. So I'm going to start with something like that that's engaging. Then I'm going to look at the sales dashboard okay. I'm going to look at all right how are we doing on performance.

:: 05:02:01

Speaker 1

Who's kicking ass who's not. If you're if you're kicking ass, what's what's working for you? What's what's not working for you? If you're behind, like, what are your blockers? What are the obstacles? What are the challenges that you're facing right now and hitting your goal? I'm also going to probably look at something around activity, like when I look at sales, I see like there's activity that's inputs into the system and then there's results.

:: 05:22:20

Speaker 1

That's the output. You can talk about the output all you want, but if you don't talk about the inputs then it makes it very difficult to actually affect the output. So I may work backwards and say, okay, if it's, you know, if it's calls that you've got to go on or whatever the other activity metrics are like, if there are doors, you're supposed to hit calls, you're supposed to make emails, you're supposed to sound like, what are those things?

:: 05:40:16

Speaker 1

Because those things are fully within your control. And then you can end the meeting with commitments. Right? And you can actually look at the activity logs because again, those are fully controllable. Like I can't always control the conversion rate on a sale, but I can't always control how much I'm going to put in the system, how much work I'm going to do, how much activity I'm going to get started.

:: 05:56:26

Speaker 1

So you really just want something that is going to set the tone the way that you want to set the tone that you're going to go through and look at the numbers, look through where you are on performance. What are the results that you have so far? Are we hitting the key activity metrics, and are there some commitments that we can make walking out of here.

:: 06:12:25

Speaker 1

So that next week when we show up, we can look at that and say, okay, are we doing those things? And then are those things getting us that output? So that's a sales meeting that you've got to run every single week, even if you've got one sales person, you go through this activity. If you have one sales person, probably do it in 30 minutes.

:: 06:27:02

Speaker 1

If you have three or 4 or 5 salespeople, it's going to take you probably an hour. But you want to make sure to hit this every single week. Now, the next thing you want to make sure you're doing every single month is you want to make sure that you're reviewing or going on at least three sales calls. If you're running like a consultative sales process, like I work with a lot of IT companies and, you know, you've got, you know, SDR calls and you've got, you know, qualifying calls, discovery calls, proposal meetings.

:: 06:50:03

Speaker 1

Make sure to mix it up, try to observe a minimum of three every single month. But you know, look look at some that are proposal. Look at some of their discovery. Look at some that are qualifying. If you've got a sales dashboard, you can probably look at what's the area that's underperforming right now. And do we want to focus on that right now.

:: 07:04:18

Speaker 1

Do we want to troubleshoot that specific area. The other important thing that you're doing as a business owner is you're getting research and development from your sales calls. You're going to hear about what competitors are coming up and why are they coming up. What are the price objections sounding like? What are the other objections that are coming up?

:: 07:20:25

Speaker 1

Like one of the prospects saying, what are the questions that they have? Where are they showing skepticism like all of that is on you to objectively look from the outside and go, okay, like we can actually make some adjustments here. You're looking for is your your salesperson following the process. And if they're following a process, how well are they executing it?

:: 07:36:13

Speaker 1

Right. Like are they actually following the steps. And then qualitatively, are they executing according to a playbook or something like that happen when I sit down to do a coaching session where I like them to do is have the opportunity to observe the call before I show up. Right? So if it's in person, they know that that's okay.

:: 07:50:03

Speaker 1

I went on that call. We're going to talk about that one. If I'm listening to it asynchronously or it's on recorded calls, I want to share in advance because the first question that I'm going to ask us, hey, how do you think it went? Right? Like, how do you think that the call went? Is there anything that you would do differently, right, if you got that opportunity to do it again?

:: 08:05:17

Speaker 1

Because a lot of times they coach themselves, they hear it and they go, oh man, should I do that? Or I kicked ass there. So you want to ask them, like what? How did you think it went? Anything that you would improve, anything that you think you did particularly well, like when you listen to it.

:: 08:19:07

Speaker 1

Like what? What strengths do you hear? And I want to get that feedback. It tells me a lot about how they perceive their performance up to this point. And then what I want to do is I want to share a few observations about the call. Right. Like, and that can be, a little bit of both, you know, green hat and a little bit of red hat.

:: 08:34:04

Speaker 1

I want to share 3 to 5 observations. I want to mix it up if I can. I'm also like a very direct person now. Like if there's not a ton of good, I'm sure you can find something, but you don't have to sugarcoat shit if it's not a good call. You guys should have that conversation, right? Or if it was a phenomenal calling.

:: 08:46:10

Speaker 1

Don't really need to make shit up. So, share the observations. Really critical piece here, though, is only asked for one change walking out of this session, right? So if you share 3 or 5 observations, don't ask them to change five things like these are this things that I hear. So, you know, keep doing these things. And here's one thing that I would like you to improve on.

:: 09:05:08

Speaker 1

Now the other thing is on these coaching sessions, if you're doing them virtually really cool, you can just use like an AI summary tool that says, hey, here's the summary of what happened, and here are the action items from here. If you're not doing them virtually and you don't have that opportunity, then I still recommend getting a summary and getting the action items and documenting it.

:: 09:22:00

Speaker 1

Not and not documenting necessarily from an HR standpoint, a little Prime minister, but documenting it from a hold yourself accountable. One of the biggest challenges I actually see when people try to do sales management functions is they're not accountable and they're not executing the right way, like they they say, hey, you should go do these things. And then they never go back to see if they did those things right.

:: 09:40:15

Speaker 1

So don't fall into that trap like you lead with the accountability by example. So, you know, grab my summary tool. Reinforce what that is documented. Clarify you know what the what you guys agreed on and what's going to be improved. Now similarly, you've got to do at least one role play session a month minimum. Practice makes permanent, right?

:: 10:00:13

Speaker 1

Like somebody said this to me recently, it really stuck. And I said, you know what? That's that is great. Like the the way that you practice is the way that you're going to install the behaviors. Okay. I've always said you don't want to practice on purpose, not on prospects. Choose whichever one you want. But at the end of the day, there's value in practice and the call reviews are always in hindsight, right?

:: 10:18:21

Speaker 1

Like so you can do those types of things. But the role play allows you to coach through different scenarios and in a somewhat more controlled environment, because you can be a realistic prospect with the the objections and force that process. Now, the thing about role plays is if you are the prospect of you're playing the prospect you really want to be as realistic as possible.

:: 10:38:21

Speaker 1

So think through what the scenarios are like. I've actually been using GPT right and saying, hey, what are some scenarios that I could use? Like how can I, you know, what questions can I have? What obstacles can I have, what, objections can I have. And actually using that and some of the role play so you can do something like that, but just want to make it realistic because you don't want if you go in and you're just going to act like a lay down, they don't you're not really practicing anything.

:: 11:00:11

Speaker 1

It's it's a complete waste of both of your time. So make it realistic. Make it practical. Now, easy way to do this is you just share your scenario. Like as a prospect. So like what kind of company are you? What's what are your primary objections. Like what are the key things that your salesperson would want to know or need to know or typically know?

:: 11:18:16

Speaker 1

At that stage in the process? So like, if you're going if you're going to be doing like a roll plan or a, you know, qualifying call or on a discovery call or on a proposal call, probably going to be different levels of information. So think that through it like just get it kind of specific about what those things are and really intentional at least then have the salesperson execute the process like that section of of what you want.

:: 11:37:24

Speaker 1

Similar to the call coaching. Ask them how they thought it went. Like a lot of times role play makes people nervous a lot of times. And so you go, okay, like, all right, let's do it again. Right. But they'll tell you, like, you know, I kind of screwed this up. Okay, let's do it again. Right? Like, let's let's run back through it.

:: 11:52:28

Speaker 1

All right. Let's try it again then. Same thing. Share 3 or 5 observations. Like what did you see as you're going through like any, any notes that you took things like that. And then ask them to focus on one high leverage improvement. Just one. Make it easy. Like one. What's the one thing that you saw that you're like, I know I want to tell them five things, but I we got to start here.

:: 12:11:03

Speaker 1

Like, let's stack these things on top of each other. So, you know, just find the most important one, make that the focus and then start there the next time. The next thing you've got to do every single month is a full pipeline review, whether you're working with a closure or, you know, somebody that's full cycle, that's out there doing prospecting and closing deals, you need to sit down at least once a month, like in a lot of cases where I've done fractional work, I've done it every single week when I want to, like, really understand what's going on in the pipeline and start to speed things up and accelerate the sales process.

:: 12:41:14

Speaker 1

But minimum once a month you want a spot check, you want to know, all right, what's what's the real pipeline health. What are all these deals? What you know, like walk me through them. And what are the next steps on this? Are we talking to the right stakeholders? Like what deals are actually stalled or stuck that we're not talking about?

:: 12:57:12

Speaker 1

Can we get creative with how we address those things, actually have a full pipeline review video that like actual training, like the entire agenda, everything that you need to run that. But the short story of this is basically you're going to review every deal in the pipeline, like, am I'm going, I'm going to audit every single deal on the pipeline.

:: 13:14:11

Speaker 1

Like unless you are working such high volume that you can't go through each deal, then I'm going to go through each deal. And if I have that much volume, it might be time to get another salesperson because the likelihood of them being able to actually give all the attention that they need to those deals, depending on your sales cycle on everything may be very low.

:: 13:31:12

Speaker 1

So that may be symptomatic of something. But I want to know what are all the deals in the pipeline then I want to confirm are we working with the right person. Right. Like who's who's the stakeholder? Who's the decision maker, who's the next step with okay. And that's going to that brings me the next thing. What is the actionable next step.

:: 13:48:12

Speaker 1

And I'm going to tell the person from your part like the because the waiting is not a next step. Right. So if you're waiting for a contract, waiting for a callback, waiting for anything, then my next follow up is okay. So at what point are you going to do something like is waiting is not an action step. So if I have not heard by Wednesday, what are you going to do?

:: 14:09:23

Speaker 1

Where are you going to stop by? Are you going to make a phone call or are you going to shoot him an email? Like what's what's going to go on? You know, so I want to know what is the specific next step. And I want to also look for things that really feel stalled. Right. Like I want to troubleshoot some of these deals if they feel stuck, if they're not making progress or something just doesn't smell right.

:: 14:26:21

Speaker 1

I want to double click on it. Like let's let's look at that. Like what? Okay. So the next step is at this date with this person. What have you done up to this point. Like what else has gone. And you're kind of like trying to sniff out which deals are actually stalled because that's a really good opportunity to say, all right, let's let's get creative.

:: 14:41:08

Speaker 1

Send them a pizza. I mean, like, you know, like do you could get creative to get the attention of your prospects in your pipeline, but you can't help them problem solve if you don't know that there's a problem right. And you don't know there's a problem if you haven't gone through your actual pipeline. So sit down and go through that.

:: 14:54:11

Speaker 1

Then you want to get what those next steps are and document them like, okay, well these are the next steps. And accept these I got it. Cool. That's the action list. That's going to be your focus this week. This month when we meet next month I'm going to start with this list. I'm going to say all right cool.

:: 15:07:23

Speaker 1

This is what you said you do. Did we do it. Did we do it. Did we do it. Do we do it right? Like so. There's accountability. So once a month minimum pipeline review that you run with that agenda. And then the next thing is one, one on one meeting with them outside of these frameworks, outside of this structure per month, this is just the human side of management.

:: 15:26:12

Speaker 1

This is this is the leadership side of it. You want to connect with your sales person as a person. You want to connect with them as a human being. And you want to, you know, create the environment where you've got two way communication, where you've got candid communication, where you know, there's some trusted rapport built up between the two of you so you can have productive conversations even if they're tough.

:: 15:46:29

Speaker 1

This doesn't have to be in a stuffy office. This doesn't have to be a rigid criteria. You can, you know, go out for, have a have a beer. You can take them to lunch if you want some space with your salesperson every single month to essentially check in and open the door to candid feedback, both directions. Right. Like it's that's your opportunity to share, you know, feedback and you know that you have like, I can't tell you how many business owners or sales leaders that I talk to when I'm coaching them.

:: 16:14:21

Speaker 1

And they're like, well, you know, Johnny sucks and he's not doing this. Have you guys talked about that? No. Okay. Now we should talk about that because there's a decent chance that if I go talk to Johnny, he's going to say, you know, dipshit manager is not doing x y, z. Right. So there's like that means communication is not happening.

:: 16:31:15

Speaker 1

And that's just dysfunction within an organization. And it's up to you to change that as part of the culture. One of their goals. Right. Like what what what are they striving towards and how are they doing in achieving them? And how do they feel like they're doing and achieving them? Because it's not always the same thing. So I want to know, like, hey, what are your professional goals?

:: 16:48:00

Speaker 1

What are your income goals? Like, do I know what is motivating and driving the person that's responsible for generating our revenue? Like that's a really important thing to know. So do they have some career aspirations? Do they want to go to school or do they just want to hit a specific income number? Then I kind of want to know, how do they feel about the progress that they're making towards those goals?

:: 17:05:28

Speaker 1

Okay. Like so do you feel like you're on track? Do you feel like you're off track? Is there anything that we can do to help facilitate that? Are there any specific blockers that are in the way to achieving that specific goal? Are there any specific like projects or opportunities like here within the business that you'd like to to pursue and just doesn't have to come up every single month?

:: 17:24:17

Speaker 1

Like, what's the ultimate career goal? Like what's what's the big step, right. Like where are they going to try to jump the S-curve? Where are they going to try to go like okay, the next thing, the next thing where they want to be five years from now, right. Magowan. Like do you do you know these things. And if you don't like this is the opportunity to find it.

:: 17:38:09

Speaker 1

Yes. Do you know their goals. You know kind of how they're progressing towards them or not. But this is where getting on the same page means you also need to communicate what your expectations are, what what you think the top focus should be, what you believe the goals are, how you feel about progress or lack thereof in achieving the goals.

:: 17:57:03

Speaker 1

And is there a misalignment? Is it possible that one person feels like, hey, we're making good progress towards the goal and the other person says no, like we're way off, right? Like this is the time where you actually put those goals and the progress and the expectations and get on the same page. And again, if you have not communicated what your expectations are of somebody, then that's on you.

:: 18:18:28

Speaker 1

And this is the opportunity to ensure that you're singing off the same hymn sheet. Right? Like that. You're you're not speaking different languages and that you're both seeing things the same way. And those are the essentials, the Lean Sales management guide, right. Like you've got your weekly sales meetings. There's four of those. You've got a few sales call reviews.

:: 18:36:06

Speaker 1

You've got a role play each month, you've got a pipeline each month, and you've got a one on one each month. Now sounds like a lot. And if you're a business owner, you're thinking, where am I going to get this time? But here's the thing. If you actually break this down and look at it on your calendar, you're talking roughly ten hours a month, 30 to 60 minutes for your weekly sales meetings and an hour each for a few sales call reviews.

:: 18:58:04

Speaker 1

It's really not that much time, and it's one of the highest leverage things that you can allocate your time to because these are the things that have a high probability of driving more revenue and giving you a better understanding of your own sales process, of your own audience, and what is happening in your own business and almost anything else that I can imagine and I can tell you, like, as a sales leader, I can tell you without a shred of doubt.

:: 19:20:27

Speaker 1

I promise you, if you do these things, your sales will increase the process is going to improve dramatically from what you're learning, because you've got a good feedback loop, and the execution of that process is going to improve. Because interesting thing that happens with with sales people, sales teams in general, is that once there's a little bit of accountability, like once you start reviewing a couple sales calls, it raises the quality of all the sales calls because the likelihood of, oh shit, if that one gets pulled or if he shows up to the sales call or something like that.

:: 19:50:09

Speaker 1

So just the idea that somebody is paying attention automatically improves the execution of the sales process, creates more accountability. You also have an opportunity to find bad habits before they've really cemented themselves into your process. If you're checking on these things regularly, what you'll see is people will drift, right? Like people don't usually just like throw the process out overnight.

:: 20:11:02

Speaker 1

What happens is they drift and so you can catch those bad habits before they become permanent installations in your process. And again, just the feedback loop that you're going to have is going to make you a better leader and a better business person. Now, if you are a business owner and you're saying, how the hell am I going to find time to do this?

:: 20:25:29

Speaker 1

A couple ideas, because I get it. I really do. Like I've been in your seat, and I have also made the mistake of saying, I can't do that, but if you don't do that, it's going to cost you more time somewhere else because you're either not going to have the sales, you're not going to have the process, you're not going to have the Intel, you're not going to have everything else, all the benefits that come with this.

:: 20:43:14

Speaker 1

So it's costing you somewhere else. So one thing that you can do is go to your calendar right now and open it up and carve out the time for next month. Right now. Right. Like whatever, whatever the next month is going to be fined four blocks to put a sales meeting in and put a date down. Invite your salesperson or salespeople to plug in your one on one.

:: 21:04:11

Speaker 1

Then plug in your pipeline review like go through and actually put these things on your calendar and then stick to them, right. Like actually protect that time and execute this process. By the way, I'd also give your salesperson or salespeople a quick heads up like, hey, we're going to start doing this. This is something that I really should have been doing.

:: 21:20:12

Speaker 1

And this is for as much for your benefit as it is for me. Here are some of the benefits you'll see out of it. Like all that's like, don't don't catch them by surprise. Like they don't want you down. It's gotten eight meetings. It's lined up on my calendar. So send a quick note but go in in time.

:: 21:33:00

Speaker 1

Box up, get ahead of it and be really proactive about it. Secondly, you can hire a good sales manager, and good sales manager should be able to pay for themselves. A lot of businesses that I work with are kind of like in an interesting spot because of their size and revenue. Like they're not quite ready to to make the leap to a full time sales manager, either because of budget constraints or because the, the like.

:: 21:53:03

Speaker 1

There's only one salesperson, but they're beyond the capability of being able to execute even the essentials that we're talking about here on their own. The alternative is you can hire a fractional sales leader who can step in and execute these things and probably add, you know, a second, a third layer, because these are the essentials. This is not everything that a sales leader or sales manager can do to drive more revenue in your business.

:: 22:13:09

Speaker 1

So get in there and just do it. Just time. Block it and stick to it. Hire a sales manager, a good one. Or go look for a fractional sales leader that can learn your business and execute these functions on your behalf without the full load of a sales manager salary. Those are a few options to consider, but the one to not consider is I'm just going to not do it, because I can tell you, not only will it if I could performance, but if you have a really good salesperson, there's a decent chance you may not keep them because they want to be engaged somehow.

:: 22:41:03

Speaker 1

They want to be challenged some way. And that's the nature of the beast with with really good salespeople. And if you're a B2B company and you're doing five, $10 million in sales and really want to scale up your sales team, look us up, check out the links in the description, possibly something that we could help you with.

:: 22:55:19

Speaker 1

Maybe not, but either way, like you should be able to take this guide, this framework, and get the essentials executed. Get the essentials installed into your business. And if you have any specific questions, drop them in the comments. I'll do my best to answer. Audience.