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Your Calendar Is Your Commission Check

First-of-the-month accountability check reveals a brutal reality: a salesperson with nothing on the scoreboard, no pipeline, no meetings, and no real plan beyond "follow up with four people" and "pack boxes for Thursday's event." This episode is a wake-up call for anyone in sales responsible for generating their own pipeline. Learn why treating your time like a precious resource isn't optional—it's survival. Discover the two critical mindsets that separate top performers from struggling reps: (1) strategic calendar planning with "The Perfect Week" framework, and (2) complete ownership mentality that refuses to accept passive excuses like "this week's basically shot." If you're carrying a "shit happens to me" mentality instead of "I make shit happen," this unfiltered conversation will either light a fire under you or make you realize sales isn't for you.

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Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

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Transcript

If you're in sales and you're responsible for generating your own pipeline—so you allocate your time, you're hunting, you're doing some LinkedIn, you're doing networking events, you're doing some BNI, or you're hitting the streets, or you're making some phone calls, and you have some autonomy over how you're going to allocate that time, and you're responsible for the results that time produces, right? So you're responsible for generating pipeline and you're responsible for converting it once you get it in—then this message is for you.

The core thing that I really want to emphasize here is the importance of your time and the mindset that you have around how you allocate it will make or break you. In sales, you have the ability to dramatically influence your own income by how you choose to allocate that most important resource that you have, which is your time. But it requires having the right mindset and the right level and the drive necessary to take ownership of it, to make some tough decisions, to allocate it properly to get the results that you want, to get the outcomes that you—and frankly, the person that you work for—wants.

This stems from the conversation that I just had with a group of sales people selling MSP services. It's now the first of the month. The first of the month, we're saying, "Okay, what's... it's an accountability check. What's the game plan?" We actually have a quarterly business plan that we reflect on, and we use the first of the month to kind of [ask], "Alright, where are we at? If we're on track, excellent. How do we keep the flywheel moving? If we're off track, what do we need to do to close the gap?"

And we're going through this, and I get to one of my sales people. He's new, so he's been ramping up for the past several months, been in training and doing some classroom stuff. And that's fine, like up to a certain point. But it's go-time now, right? It's now been several months and it's time to put some wins on the board.

And he not only doesn't have any sales—which isn't a huge deal at this point given the sales cycle—but he also doesn't have any deals in the pipeline. Doesn't have any actual bookings. Doesn't have any meetings on the calendar right now. Doesn't have any real, legitimate, active leads that he's pursuing. So basically, nothing's happening.

And when I look at this, if I'm that salesperson, I'm going, "Hey, it's fucking time to go." Right? Like, I've got nothing on the board. I've got nothing in the pipeline. I've got one goal, which is to get sales, and I've got one way to influence that right now, which is volume. Which is input. Which is activity. And that is the phone calls I make, the LinkedIn connections I make, the networking events I go to, the doors I knock on, whatever it is. I get to allocate that time and I've got one target in mind, so I'm going to sit down and get really fucking serious about how I'm allocating that time. And I'm going to push as hard as humanly possible, as hard as necessary, to get the results that I want. Because I take ownership of it, and I'm driven, and I don't like to fail, and I like to make money.

So, we get to this particular person and he says, "Well, you know, I've got a few leads from a previous event that I'm going to follow up on. And I've got a networking event on Thursday that's an all-day thing, and then another one on Friday and it's an all-day thing."

And this is Monday morning. And I said, "Okay. So Thursday/Friday are off the table. You got all-day networking. So you're following up with how many people?"

"So, well, I've got four that were supposed to book from the last network[ing event]."

"Okay, so you're gonna follow up with four people?"

"It's like... it's Monday morning. We have the rest of Monday. We've got Tuesday. We've got Wednesday. And all we have on the books is, like, follow up with four people?"

"Well, you know, I'm gonna try to get out and talk to a few prospects and create some partnerships..."

"Okay... and that's going to be... that's all? Like, we've got, let's call it eight hours Wednesday, eight hours Tuesday... let's call it four hours or whatever [on Monday]. Like, that's where we're going to get done?"

He said, "Well, I gotta be back to the office tomorrow for a call in the afternoon."

"The whole day is shot?"

"So, well... almost. Like, I'm in a big city and getting there requires this, so I might be able to get to a couple of people in the morning."

I said, "Okay."

He said, "But, you know, we gotta prep boxes and stuff for the event on Thursday."

And I said, "Dude, hold on. Let me get this straight. We've got nothing. Nothing on the scoreboard. No opportunities. No leads. No... nothing. That's how you make your money. That's how you keep your job. And right now, basically, we're going to follow up with four people, maybe talk to a couple of people tomorrow, pack some boxes, do a phone call in the afternoon..."

I said, "Dude, can I shoot you straight? This isn't going to change. Like, this is not going to change because we aren't going to get results if this is the input. I'm telling you, sales is nothing but a big fucking math problem. It's a whole bunch of inputs and a whole bunch of outputs. And the right amount and the right kind of inputs drive the right outputs. And I'm hearing almost none on the front end. And more importantly, I'm not hearing any fire. Any drive. Anything that says: 'Dude, I gotta fucking get after this. I've gotta take ownership. I'm hungry and I'm responsible for eating what I kill and I've got nothing right now.'"

I'm just like staring at a barren desert of nothing. And what I'm thinking is... well, I'm going to do a couple of things.

Listen, if it's me—and this is fractional management so they don't report to me directly—I said: "Listen, if this is me, I go to my boss tomorrow and I say, 'Hey listen, I would love to pack boxes. And I'm a team player and I'm all for it—this is not about me not wanting to be collaborative, I will do this all day long—but please, for the love of God, can I take the boxes home at night and do stuff like that? Can I... I've got to get out into the field. I've got to hit 20 businesses tomorrow. I've got to make X number of calls. I've got to create a list of events that I'm going to be going to.' Like, I've got shit to do. And whatever the call is in the afternoon... unless it's a sales call, that doesn't merit losing hours and hours and hours of productivity."

And what this comes down to is... Part of it is not respecting your time as a sales person. You gotta look at yourself as like a business owner and an entrepreneur whose time is insanely valuable. And you gotta look at how you're allocating it. And if you're fucking around with boxes, or you're wasting hours and hours and hours—half a day—on drive time, then (1) you're just not respecting your time.

But (2), beyond respecting your time, it's also having the mindset around complete ownership and responsibility for achieving the damn result. Right? Like there is a hunger that I have, a competitiveness, a refusal to fail, a drive, a desire to win and make money. And I can tell you right now, if I'm in those shoes, I'm having that conversation with that business owner or that manager. I'm going to get up at the ass-crack of dawn if I need to, to go do what I need to do. I'm not going to look at somebody and be like, "Well, you know, this week's basically shot."

Dude, that is a passive mentality.

So if you're in sales:

One: Get really serious and strategic about your calendar. Plot it out. Sunday night. Write down, fill in blanks: What is happening Monday, Tuesday, Wednesday, Thursday, Friday? Put it in time blocks. Allocate that time. And then ask yourself: Is that the sufficient volume that's necessary to make shit happen? So (1) get really serious and strategic about it. Be proactive about it. And plan it out—I call it "The Perfect Week"—mapping it out. And again, putting it actually in the calendar.

And (2): Get really honest with yourself around: Are you willing to invest the energy that is necessary to achieve the results that you want? Because this is partly about time allocation, but the conversation was also partly about mindset. And I can just tell you, outside looking in—I've done this for a really long time—is that if you carry that level of a passive "shit happens to me" instead of "me making shit happen" mindset, it's going to be a rough road. And on top of that, if you don't take your time really seriously, it's going to be a rough road. You combine those two things and it's usually a bad story.

So, I'm sharing this in case it's helpful for you, or just as a reminder: Go out, get after it, take ownership, be driven, do what's necessary to move the fucking needle, push the flywheel—it's hard, especially when you're starting out, especially when you're new, it's fucking hard to get going—but that's okay, that's why we get paid a lot of money. And then guard that time as if your life depended on it, because to some extent, it kind of does.

Hope it helps. Adios.

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