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  3. #601 - How to Build a Sales Team That Manages Itself
30 Minutes to President's Club | No-Nonsense Sales

20 Aug 2026 · 34m · 11 chapters

Episode artwork

#601 - How to Build a Sales Team That Manages Itself | Tara DiCristo-Schmitt

In short

Building a self-managing sales team using three systems: (1) “The Pledge” deal/process questions used in weekly pipeline reviews, (2) “Calendar white space rigor” weekly calendar co-planning to eliminate idle time and add net-new appointments plus partner/referral meetings, and (3) “Days without report” real-time leading-indicator monitoring (e.g., days without discovery/proposal) that triggers manager/director coaching actions and “success plans.”

Key claims

reps learn to ask customers the same pledge questions; calendar filling creates predictability; leading-indicator gaps (proposal/discovery) predict lagging quota issues; leaders should coach instead of being “super reps.”

Notable examples

net new appointments turning 13 into 3 after cancellations; a rep refusing calendar access led to HR escalation, then the rep later hit President’s Club; “small business” triggers 2/5/10 days; longer cycles use 7/14/21.

Guests

Tara DiCristo-Schmitt, CRO at Houzz; formerly VP Small Business at HubSpot, sales leader at Paychex/ADP/Holy Cow/Weave.TD.

Written by AI. May contain mistakes.

Chapters

0:00

Introduction to Calendar Reviews

Learn how opening a rep's calendar can uncover productivity insights.

“And I'll say, hey, do you mind if we open up your calendar?”
2:12

The Pledge: Setting Clear Expectations

Discover the importance of clear expectations in sales processes.

“We start every single episode with your top three actionable takeaways.”
4:35

Calendar White Space Rigor

Learn how to optimize calendar management for sales success.

“So I like to call this predictability in action.”
6:16

The Health Report: Days Without Report

Explore a system for spotting trends and keeping reps accountable.

“And number three is what I like to call the health report, but to describe it to you all, I'll call it the days without report.”
8:11

Implementing Accountability in Sales

Understand how to implement accountability without micromanaging.

“It's a, hey, let's build a success plan.”
12:34

Real-Life Story of Calendar Challenges

Hear a personal story about overcoming resistance to calendar transparency.

“And then what happens that director and some of the manager will be in there as well.”
14:00

Navigating HR Challenges and Coaching Dynamics

Learn how to overcome HR barriers and implement effective coaching strategies.

“So I needed to say, okay, it sounds like you're not ready for this help.”
23:44

The Know Your Business Meeting Explained

Understand the structure and purpose of effective pipeline and performance reviews.

“Oh, yeah, they really want this, this, and this.”
28:00

Leadership Practice: VP Visits and Time Management

Learn how VP visits help identify leadership gaps and improve rep coaching.

“Does a similar exercise happen with directors to managers or with, you know, your VPs with your directors?”
30:28

Identifying and Breaking Bad Sales Habits

Discover the common bad habits of sales leaders and how to overcome them.

“TD, we've talked about a lot of great habits and best practices for sales leaders.”
Show all 11 chapters
31:20

Key Insights and Recap of Sales Practices

Review essential sales practices and insights from the discussion.

“Everybody stick around for a 60-second recap coming up soon.”
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Transcript

Automatic transcript. May contain errors.

0:00Tara DiCristo-Schmitt: And I'll say, hey, do you mind if we open up your calendar? The first question that they will say is like, like you want to see my calendar? And I'll say, yeah, I want to see what's going on because the best way for me to help you get to where you want to go is to see what you're already doing. And by the way, I don't care what's on there. Just let me see what's going on. And when you say, I don't care what's on there, just let me see so I can help you. They open up their calendar. And so you then just start asking. You say, hey, tell me how many demos did you have on there? You know, they'll start to walk you through.

0:23Tara DiCristo-Schmitt: And they'll say, okay, how many net new appointments did you have? And they'll say, oh, 13. and you'll say, okay, so can you walk me through the 13 and tell me the output? And then what you watch happen is that 13 quickly turns into three. And then what happens, that director and the rep start to see, oh my goodness, I went into the week with a really solid plan. But I had so many cancellations that I almost could look you in the eye and say, I really didn't do anything this week to add any new pipeline to the business.

0:52Good morning, everybody, and welcome to this leadership episode of 30 Minutes to President's Club. Today, I have a 20-time President's Club Achieving Sales Leader. She is currently the CRO over at Houzz, formerly the VP of Small Business at HubSpot, formerly a sales leader at Paychex, ADP, Holy Cow, Weave.TD, the CRO. Mark, why should people listen? I don't know how many episodes I've done on the Leadership Edition. It has to be close to 50. this may be the most tactical you can listen to the first 10 minutes of this and listen to how she does stuff and walk away with three things that you can immediately do tomorrow that will make your sales org better this lady has perfected the art of the little tactic that you can do that you wind into your culture that absolutely makes a difference she was amazing yeah i mean we got into stuff like the days without reports that, Mark, I've never seen you like mid-show pinging your team being like, we're building this report now.

1:58We talked about pulling up calendars with your reps and live filling them out. We talked about doing that with your Frightline managers. Also, you are looking for an extremely practical, applicable episode. This is it. All right, TD, welcome to the show. We start every single episode with your top three actionable takeaways. So let's get your three.

2:18Tara DiCristo-Schmitt: All right. So number one, I have the pledge. The pledge is clear expectations that allows reps and managers to know if we're selling to suspects or prospects. So I like to say that the pledge is the standard to run any sales process. So, so often you have managers that are going through pipeline reviews. We want to make sure we have really strong pipelines. So I designed these questions to make sure that our managers are having the right pipeline calls or conversations with the reps. Now, here's the trick of this. because the managers are asking these questions every single week in their pipeline reviews, the reps, the sales reps are getting very good at asking their customers these questions.

2:55Tara DiCristo-Schmitt: So when a rep is coming in to their pipeline review, they know these answers. They have now engaged with this customer and they now know that they are in a true buying process with the customer. So let me give you an example of what these questions are. So the first question you're going to ask is, what inspired you to connect with me today? That's going to give us the opportunity to know if we of something we can even solve. Then you're going to ask, what are your business objectives over the next year? Now I know that this buyer has something that they're trying to solve for. What challenges do you foresee getting there?

3:25Tara DiCristo-Schmitt: Now I know that they've got some areas where they think they need more than they have today. What alternatives are they considering? That now tells me and the sales rep, me, the manager, and the sales rep, that I've got competition that's out there. They're not just looking at us, and I got to run my sales process accordingly. Then I want to know when are they looking to implement change. This tells me if I'm going to run a long sales process or a very fast sales process. Then I want to know if status quo is an option. Because if status quo is an option, I again know my competition is the status quo versus them looking at another competitor.

3:59Tara DiCristo-Schmitt: Then I want to know what is the consequence of no change. That question right there tells me almost everything I need to know about the customer being a prospect or a suspect. The consequence of no change tells me if they're willing to just keep the business going the way that it's going. And then it's very important that you know that you're at the owner, who the owner is, and what is the decision-making process, and who else will they consult. Those things being asked every single pipeline review will create a very healthy pipeline. Well, I only have one question for the next part, which is, what's number two?

4:35Tara DiCristo-Schmitt: Calendar white space rigor. So I like to call this predictability in action. So think about sales reps today. They want to be busy and they want to be talking to people that can buy from them. And so, so often they reach a place of burnout, but not burnout because they've got so much going on in their calendars. Burnout because they don't have enough going on in their calendars. So I created the white space rigor, which is meeting with your reps on a weekly basis, opening up their calendars together and filling their calendar so there's no white space. There's nothing better than going into the weekend knowing that you have the rest of the week set up and ready to go and that you can plan for and have really great conversations.

5:13Tara DiCristo-Schmitt: So the trick of this is the reps that you have, you want them planning their calendar out two weeks. That gives you time to truly fill the white space. Again, we often think I've got to fill the white space with only people that can buy from you. That's true. But we also want to fill our white space with those that can refer us to businesses that can buy from us. So you will sit with them on a manager will sit with the rep, open the calendar and there's thing you will start with. Okay. What channel partners do you have already booked? What existing customers do you have already booked? What second appointments do you have already booked?

5:45Tara DiCristo-Schmitt: Good. The calendar's looking like it's really full. Now let's go ahead and schedule net new appointments, right? That's the secret. You got to keep adding net new appointments into the calendar. Once I've got all the net new appointments in the calendar, in addition to the other appointments that I just shared, it's then let's create your target counts. Let's create your phone blitzing. Now I'm sending that rep into the week with a plan A, a plan B, and a plan C, making sure that throughout that week, Monday through Friday, there's no white space in their calendar. Wow. Phenomenal. Round us out, TD.

6:16What's number three?

6:17Tara DiCristo-Schmitt: Okay. And number three is what I like to call the health report, but to describe it to you all, I'll call it the days without report. And the days without report is a system that I created that allows you to spot trends in real time. So this one is for managers of managers and managers, and it turns out to be a way that sales reps can actually manage themselves. So what you do is you take a look at your sales process and the leading and lagging indicators that go into your sales process, and you manage days without those critical leading indicators. So for example, it might be discovery for your business.

6:52Tara DiCristo-Schmitt: It might be proposal for someone else's business. You look at the sales cycle. So for an example is if your sales cycle is eight days long, if a rep has gone two days without a proposal, then the director would ping the manager with an email or Slack and say, hey, I've noticed Johnny has gone two days without a proposal. Are you concerned? That instantly triggers the manager to take action, to take a look at Johnny's calendar, make sure he doesn't have white space, review his pipeline, and help Johnny get a proposal on the calendar. If a rep has gone five days without a proposal, the director then sends a note to the manager and the rep.

7:35Tara DiCristo-Schmitt: Hey, I noticed that you've gone X amount of five days without a proposal, Johnny. How can I help? So now you've just added accountability to the manager and to the sales rep that they've got to do something quickly because it's been five days. Now you get to 10 days and the rep has not created a proposal, the director sends a note to Johnny and the manager and says, looks like you've gone 10 days without a proposal. Let's get on the calendar and build your success plan. The rep shows up, the director's there, the manager's there, all three are on board and building a success plan to get this rep back on track.

8:11Tara DiCristo-Schmitt: It's not a blueprint. It's not a you're in trouble. It's a, hey, let's build a success plan. Something came off the tracks and we got to get it back in. Let's look at your calendar. Do you have enough going on there? If you do have enough going on there? Let's look at the conversations that you're having. Are you having the right conversation? Do you have the play? Are you asking the pledge questions and all of your questions? Where is the deal falling off? Is it in the deal conversation or is it in the actual building of your calendar? I think this days without is like so simple of a thing that if you're listening right now and you're a sales leader and you don't go implement this in the next week or two, you are crazy.

8:47I mean, but I do see one thing that would make me nervous about doing it, TD, which is I send this out to a rep and they're like, somebody's looking at my calendar and seeing I'm not doing a demo every two days. Wait, five days again? Like, what's, why are they all on my back? Like, how are you managing the feeling of micromanagement, the feeling of like, oh, you're all up in my business and not letting me do my thing?

9:12Tara DiCristo-Schmitt: It's a great question. And it's And asking anyone to open up their calendar is a little revealing, especially in today's days, right? You never know what you're going to see on the calendar. Walking the dog from 11 to 2 today. Exactly what you end up finding. So the way that you implement this, if it's not, if you haven't opened the doors to your culture, if you're taking over another culture, you've got a new role. The first way that you do that is you introduce it to the director. and you ask the director if they even know what's going on in everybody's calendar. And the first question answer you get is yes.

9:50Tara DiCristo-Schmitt: Like, I absolutely know everybody's busy. Everybody's doing more than they could be doing. And can we test that? Do you have a rep that's asked for help lately? And they'll say, they'll give me the name of the rep. And then what I'll do is I'll actually model the behavior for them. Whether I'm the director, I'm the VP, or I'm the CRO, I will model the behavior. So I'll ask them to come in and I'll say, hey, do you mind if we open up your calendar? And I'll tell the director, give them a heads up that we're going to take a look at the calendar. And so they'll come in. I'll say, can you open up your calendar?

10:17Tara DiCristo-Schmitt: And so the first question that they will say is like, like you want to see my calendar? And I'll say, yeah, I want to help. I want to see what's going on because the best way for me to help you get to where you want to go is to see what you're already doing. And by the way, I don't care what's on there. Just let me see what's going on. And when you say, I don't care what's on there, just let me see so I can help you. They open up their calendar. then what you do is you say, all right, how many appointments did you have this week? Because they're never color coordinated. You really have no idea what's on there.

10:44Tara DiCristo-Schmitt: And so you then just start asking, you say, Hey, tell me how many, uh, demos did you have on there? And they'll say, Oh, one, two, you know, they'll start to walk you through and they're saying, okay, how many net new appointments did you have? And they'll say, Oh, 13. And you'll say, okay, so can you walk me through the 13 and tell me the, the output of those meetings? And then what you watch happen is that 13 quickly turns into three. Today's show is brought to you by Proposify, the proposal management software designed to make every deal a closed deal. When you send a proposal to a prospect, include a video of yourself walking through the proposal because it's going to be shared with stakeholders beyond just your champion.

11:19You want to make it easy for those other people to digest and you want to be able to control the narrative with your presentation. And bonus, Proposify data shows that when buyers watch the video, it increases your chances of winning by over 3x. So do not let your proposals become a disappointing plot twist. Get our proposal success guide free in the show notes. Today's show is brought to you by Ambition, the coaching and performance platform helping sales leaders turn metrics into action. Did you know that sales orgs where the majority of reps are coached weekly are twice as likely to see high quota attainment than those who don't?

11:48And that is from Ambition's new state of sales coaching report that also found teams using a system like Ambition coach almost 60 % more frequently than those who don't have one. Now we built a toolkit with our friends in Ambition on how to actually use data to coach your team. Get it for free in the show notes. Today's show is brought to you by Pipedrive's easy to use and customizable CRM with built-in meeting intelligence. My favorite discovery question is the multiple choice question, which sounds like typically when I'm talking with folks like you, they're focused on A, B, or C, which is it for you?

12:16Now, A, B, and C have to be problems that you can solve because that's how you steer the conversation in the direction of places you can help them. Now, Pipedrive's built-in meeting intelligence helps you focus on your follow-up question, not on scrambling to take live notes. And we built a full discovery toolkit with them free in the 30 MPC closers hub. There's a link in the show notes.

12:34Tara DiCristo-Schmitt: And then what happens that director and some of the manager will be in there as well. And the reps start to see, oh my goodness, I went into the week with a really solid plan, but I had so many cancellations that I almost could look you in the eye and say, I really didn't do anything this week to add any new pipeline to the business. And that's when the rep and the manager and the director have the aha moment. And they say, well, what do I do now? And then you start walking them through who else can refer to you? Who can you meet with that can refer to you? What customers can you have pre-planned?

13:09Tara DiCristo-Schmitt: What targets can you - Can't always go that well, though. You got to have the rep that gets mad. I mean, they can't all be like, oh, TD, thank you so much for blessing me with your introspection and inspection. Fair, fair, fair, fair. So I'll tell you. Okay, so I'll give you, you want a real story? Yeah, we love the real stories. I mean, that was a real story also. Give me a real story. Make one up. Tell me. Right, right, right. Let me give you a real story where it went very, very wrong. So I won't say the company, but I walked into the company as this new role. That model I just explained to you had worked very well.

13:48Tara DiCristo-Schmitt: So in the past. So I assumed it would work very well in this new culture. But what I learned is in this new culture, what happened, one, is the sales rep refused to open their calendar. So I needed to say, okay, it sounds like you're not ready for this help. We're going to end this call. I'm still willing to help you because your productivity hasn't been where you want it to be. Is that fair? Yes. Okay. And when you're ready, you can put time back on my calendar and I'll be ready for you. Well, that was, you know, okay, that's not when I figured that they were going to put time back on my calendar.

14:23Tara DiCristo-Schmitt: What I got instead was a call from HR. All I got from HR was to tell me that I'm not allowed to look in people's calendar. And so I respectfully said to HR, then it's impossible for me to help the managers do the job that they need to do to coach and develop their people. Let me explain to you what this is. And I explained it to HR. And HR was like, what? Yes, of course you have to be doing this. right? Because when you're in a, especially in a remote environment. And so a week later, that same rep put their time on my calendar. And I have to tell you something about that same rep. That same rep was the top rep for six years, the company, number one for six years.

15:01Tara DiCristo-Schmitt: The year I happened to step in, that rep was not going to hit President's Club. Not only were they not going to be number one, they were not going to make President's Club. By the end of that year, that rep made President's Club. I mean, on her way out, updating her resume, made President's Club. And what I know about her this year is she is number one in the segment. I want to help listeners benchmark based on what you've used in the past, because you've sold at a number of different businesses, ADP, Paychex, HubSpot, House. And I'm curious about for this report, for each of those businesses, what was the leading indicator that you used for each?

15:42You've mentioned like proposal, demo, days without disco. And then what was the number of days attached to each? And it might be helpful to get a sense of like sales cycle or complexity because I know it's different across each business. So I'm wondering if you can give some examples of what this looked like in past leadership roles so folks can very easily go benchmark against how you did it. Yeah.

16:04Tara DiCristo-Schmitt: So in small, very small business, it was two, five and 10 days because the sales cycle was eight days. So you wanted to see things happen. And I'll tell you, I actually started with a lagging indicator, which was the sale. So I initially started and that is, and I still use the sale today. So we'll look at, we'll look at the sale and then we'll quickly go to the number one leading indicator. And so that is either going to be depending on your business, your proposal or your discovery. And so like today, because we want to increase sales, I'm not looking at sales as much. I have the team looking at discovery.

16:41Tara DiCristo-Schmitt: How many net new discoveries do we have over the course of two days? Does each rep have over the course of two days? And that's the initial trigger. And that trigger will say, hey, so-and-so went two days without. And that's because right now our stage in age is we are adding activity. We are adding the right activity to our motion. A year from now, I will strictly look at sales. And I'll say, you've gone two days without. And then we'll back into their calendar. In a longer sales cycle, anywhere from, let's say, 30 to 90 days would be the longest sales cycle I've had. Probably around maybe a little longer than that.

17:16Tara DiCristo-Schmitt: But let's just say somewhere in that 45-day range. It was 7, 14, and 21. And that metric was what we would call the business proposal. I hear my AI nerds yelling right now, td i'm going to just set up an agent it's going to look at everybody's calendar it's going to fire off an email and say hey why haven't you had a proposal in two days what's your reaction to the ai nerds it's really funny because if i i opened up my slack to you right now it was the exact dialogue i had with our uh head of sales and and actually here's what'll make you laugh i said to her, have you put this in Claude to see if this can be automated?

17:59Tara DiCristo-Schmitt: Not because I wanted to take away the coaching action, because I didn't want her to have to spend the administrative time on it that you had to spend on it prior to having something like Claude and AI to be able to do it for you. So she's actually going to that exercise today for us to see what will the output be. The most important thing is that it triggers the manager to take coaching action. More importantly, it triggers the rep to coach themselves. So would you send the email to the rep or only to the manager so the manager has to have a conversation with the rep? I would follow the exact same process.

18:34Tara DiCristo-Schmitt: So I would have the first note go from the director to the manager. I have the second one go from the director to the manager and the rep. And then I'd have the meeting set up automatically. Once the behavior becomes part of your culture, but you start sharing the report to the entire segment. So it comes out daily. So everybody can now see it. So what ends up happening is a rep opens it up. They see them at two days and then they go to the manager and the director first. And they're like, I know it says that I'm two days without, but here's what I have coming in. And, and so you've created a high performance culture of people managing themselves to the work they need to do every day.

19:09Tara DiCristo-Schmitt: And you know, like that's the secret to it all. Like when I know who I am and I know what I need to do, I go do it. I read a book and one of my first VPs told me people only don't do things for three reasons. They don't know what to do. They don't know how to do it or something's in their way. And they're like, your job is to make sure that they know what to do, make sure they know how to do it and get shit out of their way. I think it's that simple stuff that as a leader helps you. Now, you have days without. I'm stealing that 100%. Then you have this white space management thing. where you, again, ask to look at somebody's calendar, feeling days, and now you have this deal review thing where you have the questions and I'm starting to see some themes.

19:54But when you said you, you, you lay out like five or six specific questions. So as a manager, I'm sitting down to do my deal review. Do I ask the rep those exact questions, just like they would ask them of a, of a buyer? Or are you checking on the answers? Like, tell me the logistics of how you coach that in the deal review?

20:12Tara DiCristo-Schmitt: Yeah. So the pledge comes into the know your business deal review, pipeline review, right? We say, do you know your business? That's kind of the idea. Like you want, as you were training the managers, it's, do your reps know their business? And you'd be surprised how many reps don't know their business. And so these questions help the manager and the reps make sure everybody knows the business. And so if I was, if I was sitting in a review with them and they came in, I'd say, all right, I actually would say, pull up your pipeline and I would randomly pick deals. so I wouldn't have them serve me up deals because I want to know if they know their business, right?

20:42Tara DiCristo-Schmitt: I'm trying to create something that they can bring with them, a skill that they could take with them later. It's not just for my pipeline. So I pick randomly. So they don't know which deal I'm going to pick. And I'll say, all right, so tell me, why do they connect with you? What inspired them to connect with you? So that's the same question that they're asking the buyer. What inspired you to connect with me today? Then I'm asking, okay, so tell me what business objective are they trying to solve? And typically in the beginning, I'll get an answer like, oh, they need ABC feature. And I'll say, nope, I want to know the business objective that they're trying to reach out.

21:15Tara DiCristo-Schmitt: Right? So, you know, and then I say, well, it doesn't sound like you know that. So let's go back and find that out. And then you can bring this deal back to me. So I'll stop them in the very beginning if they don't know. From there, if they do have the answer to the business objective, I say, okay, great. So tell me what they shared with you based on the challenges they had getting there. And then they'll give me some answers. And I listened for this. Did they make it up or did the buyer actually say it? And I'll say, did the buyer say that or did you assume that? What does it sound like for a salesperson to make up the answer to the question versus it's clear that it came from the buyer?

21:55Because I know I've sat in the rep seat where I get asked the question and I'm like, okay, let me kind of BS my way through this. What are the things you are listening for to tell that the rep is BSing you?

22:05Tara DiCristo-Schmitt: Yeah, I'm listening for, oh, things are going to be too expensive. They don't have the money to do it. They already looked at us for that. It's things that you make assumptions on because you didn't ask the question. Today's show is brought to you by Proposify, the proposal management software designed to make every deal a closed deal. When you send a proposal to a prospect, include a video of yourself walking through the proposal because it's going to be shared with stakeholders beyond just your champion. You want to make it easy for those other people to digest, and you want to be able to control the narrative with your presentation.

22:35And bonus, Proposify data shows that when buyers watch the video, it increases your chances of winning by over 3x. So do not let your proposals become a disappointing plot twist. Get our proposal success guide free in the show notes. Today's show is brought to you by Ambition, the coaching and performance platform helping sales leaders turn metrics into action. Did you know that sales orgs where the majority of reps are coached weekly are twice as likely to see high quota attainment? than those who don't. And that is from Ambition's new state of sales coaching report that also found teams using a system like Ambition coach almost 60 % more frequently than those who don't have one.

23:05Now, we built a toolkit with our friends in Ambition on how to actually use data to coach your team. Get it for free in the show notes. Today's show is brought to you by Pipedrive's easy-to-use and customizable CRM with built-in meeting intelligence. My favorite discovery question is the multiple-choice question, which sounds like, typically, when I'm talking with folks like you, they're focused on A, B, or C. Which is it for you? Now, A, B, and C have to be problems that you can solve because that's how you steer the conversation in the direction of places you can help them. Now, Pipedrive's built-in meeting intelligence helps you focus on your follow-up question, not on scrambling to take live notes.

23:37And we built a full discovery toolkit with them free in the 30MPC closers hub. There's a link in the show notes. Can you tell the difference between like a positive answer? Oh, yeah, they really want this, this, and this. And you're like, no, that's not true. you know, cause sometimes he's, I don't think of rep. I don't think most reps go in thinking I'm going to deceive TD today. When she asked me these questions, I think they go in thinking I should know this. And I had the conversation and, and I think this is what she wants to hear and all that mixes together into an answer. That's not really true, but not really a lie.

24:09You know what I mean? A lion says valentine. They're not there to deceive you. Most of them.

24:15Tara DiCristo-Schmitt: No, I would say they're never there to, to do that. Um, what would be, Do they do that? Now you're making me think. I mean, yes, yes. And what does it sound like? It sounds exactly what you just described. A bunch of things all put together. And typically what I'll do is I'll smile. I'll ask the same question. Did they work for that? And they'll be like, I don't know. I got to go back and ask. And I'm like, all right, well, let's go back and ask. Then I'll say, why is it important that we know the challenges that they think they're going to face? And then they'll tell me. And I'll say, all right, so let's figure them out.

24:45Tara DiCristo-Schmitt: And then I'll often say, you want to call now? Let's call them together. Ooh. We'll pick up the phone together or the manager will pick up the phone together. And the rep can hear that. It's not so scary to ask that question. Like you said, they either don't know, they don't want to, or they don't know how. And so you gotta, you gotta give them the confidence and the confidence to, to go do it. Where'd you start your sales career? ADP. ADP. I can tell. There's a few companies where you can tell that people have this, um, fearlessness to just go get the right answer because they know the right answer is what helps them do their job and helps their buyer.

25:19And like, you're doing that, you're modeling that, but like, I don't know if you're explicitly telling people that, but I, you know, we talked earlier and you're talking about, you're creating this kind of corporate culture of our coaching culture, a culture of coaching. And, and really what I'm hearing from you is, is it is coaching, but what I'm hearing is it's more about consistency and modeling. It's more about, we can do this over and over and over. And when you don't know it, I'm going to show you, I'm going to show you. I'm going to show you. And then that breeds people to know what to do and how to do it, right?

25:50And then you can move this stuff out of their way. I want to ask about the format of this. You call it the Know Your Business meeting. And it sounds like part of this is a more traditional pipeline review. Your reps have so many deals in pipe that you have to randomly inspect. It sounds like you can't go through every single one. But I'm wondering if there are other things that go into that meeting. Are you asking the rep to give you a sense of their pipeline coverage against their quota? Are you asking them to give you a sense of new pipeline that's been generated? Are you asking them to give you a sense of, hey, based on my territory, here is how much coverage I have against the territory versus accounts I haven't touched at all?

26:31What actually goes into this know your business meeting? Because it sounds like it's bigger than just a traditional pipe review, if I'm not mistaken.

26:38Tara DiCristo-Schmitt: It is. So it starts, we call it the RPA. so if you guys are familiar with Mike Weinberg but it's the RPA and we start with results so what are your results you come in and usually the purpose of that is the high five right I want reps feeling good when they're going into these one on one meetings to talk about their business but the RPA is for the manager it's not for the rep it's what results did you get this week if the rep got the results they needed believe it or not it's a high five and a hey let's grab let's take a look at your business and I pick one and you go through the know your business because you want it to you don't want to lose that coaching opportunity that comes out of the know your business.

27:11Tara DiCristo-Schmitt: But you don't need to go through all the deals in their pipeline and activity. Now, if the rep comes in and they don't have the results, then you go into the pipeline. You immediately move into the pipeline and you say, let's look at all of these deals. What deals do you have that have a next step on them? What deals did you move out of your pipeline this week that closed and which deals came out because you decided that these deals were not, you know, they were closed, lost. You get that information and then you go into the activity. And so that's where you then open the calendar. So it all kind of blends together.

27:41Tara DiCristo-Schmitt: You then can open their calendars with them and say, let's look at your activity and where can we build in activity so that next week when you come in, you have the results. One more thing I want to ask you. I actually want to go back to the filling the white space piece because it sounds like you are encouraging your managers to do that with your reps. Does a similar exercise happen with directors to managers or with, you know, your VPs with your directors? I'm curious about the leadership white space going and if that happens. Yeah. So we call them VP visits. I have a name for everything. We call them VP visits or director visits.

28:19Tara DiCristo-Schmitt: Like for example, I'm going to do CRO visits in June. And so what I'll do, So it starts from the top down. And part of it is saying, let's see what's going on. So where are you spending your time? Open your calendar. Because everyone is always so busy. Everyone is always reaching a point, not always, lately, reaching a point of burnout. And so when someone's reaching a point of burnout, even if they're succeeding, I want to see what's going on. And so they'll open it up and I'll say, where are you spending your time? And what I find often is that managers are not spending their time listening and coaching reps.

28:53Tara DiCristo-Schmitt: They're spending it everywhere else. Directors are spending time not customer facing, not rep facing, not coaching managers and inspecting. So I designed the direct call to director and VP visits so that they can get in and inspect what they inspect. So build the calendar out. Which team meetings are you observing? What seat rides are you doing where you're going to get in with the rep and they're going to get to know you and that's going to help you build the culture? What executive outreach calls are you doing every every week? And so, yes, it's more monthly with the director and the manager calendars, sometimes even quarterly, depending on where they are in the org.

29:30Tara DiCristo-Schmitt: But the rep one is weekly. Are there certain things that you are suggesting that managers or directors cut from their calendar to make room for other things? Internally, other parts of the business will have several calls to get to an end game. And the sales leaders, I will find that they'll be sitting in those multiple calls. and I'll say, okay, there's four calls this week on the same topic. Which one can you completely delegate? Which one to me, right? So you don't have to be in it. And which ones do you, which ones do you need to be in? Is there one you need to be in? And then do you need to be in this every week or do you need to show up once a month for a readout?

30:06I think you and I are cut from the same cloth. I think there's a lot of stuff that you talk about that is very, very important and sacred to me and how things are done. You're definitely the interview I've done so far that's been the closest to how I operate. But you're doing a couple of things that are just really cool. Thank you. I don't think I have anything else. Cool. All right, cool. We got to move to our final question. TD, we've talked about a lot of great habits and best practices for sales leaders. Now I got to flip it on its head and ask you about a worst practice. So my last question is, what is one bad habit that you see a lot of sales leaders exhibiting that you think they need to break because it hurts them more than it helps?

30:46So I think them being super reps, they want to be the superhero.

30:52Tara DiCristo-Schmitt: They put the cape on, they jump in, they sell the deals. They do everything that the rep needs. They sell the deal, they run the tickets, they troubleshoot whatever's happening with their deals. And I think that is a fundamental flaw in a lot of sales cultures that I have inherited over the years. Sales leaders should be coaching and coaching and repeating and coaching and making sure that reps are getting better and can do the job on their own. Amazing. TD, thank you for joining us. This was a phenomenal episode. Everybody stick around for a 60-second recap coming up soon. All right, Mark, it is time for your two-by-two recap.

31:29What are you two? Listen, I hate to just like recap, but it's really simple. Days without. That report is so interesting. What is a super important leading metric that if it doesn't get back on track is going to lead to lagging metric problems like quota attainment? So let's find one of those. Let's see how many we should be doing over a certain period. And the minute that we start to get away from that, let's make sure that the managers, directors, and reps know there's something going on. And then the second one is, again, this white space thing. I've opened up rep calendar before. I'm not a big calendar checker.

32:03What I've never done is say, hey, let's get your white space and look at it. And what can we feel it with that will be super productive? And I think that just modeling that and showing somebody how to do that and being consistent week over week of like, these are the things that add, prospecting, prospecting, do your cold calling, do this. And reps will start to automatically start to do those things in the white space on their own. And you get to this place where TD talks about Now, your reps micromanage themselves, and there's nothing better than a rep that manages themselves. Yes. So my two were, the first one is, let's call them.

32:38So you're on your type review. TD calls it the know your business meeting. And she talks about if the rep doesn't have the answer to something, to one of those questions that she talked about in the beginning, you might decide, rep and leader, we probably need to go back to the customer and get the answer to this question. And what TD will do on these calls is like, she'll be like, let's just call them right now. And that shows the rep. Mark, you talked about the, they don't know what to do. They don't know how to do it or something's in the way. This literally, you're on the review. You got time.

33:07So nothing's in the way. And you can show them how to model the behavior of picking up the phone and calling the customer and saying, hey, I was thinking about our last meeting. One thing that came up for me was, and you can ask the question right there. And then the last piece, this was just the theme of consistency. Mark, you called it out. it was like every pipe review, every time we're talking about a deal, it is the same questions we are asking again and again and again. Every manager, every leader knows when we're talking about a deal, we're talking about these questions. And so downstream, the rep knows every deal I'm in, I better have the answers to these questions because I know my manager is going to ask me this.

33:42This is something that helped me a ton when I was a new rep. We didn't have any major formal sales training at my company, but literally every deal, my manager, she asked me the same questions again and again and again. And I kind of got sick of not having the answers. So I just see my customers, those questions and shocker, that is what TD is doing when she builds that into the pipe review culture. So the way that folks can help us out, Mark TD mentioned that they're always looking to hire. If you want to work for a world-class sales leader, send her a on LinkedIn. We'll put her LinkedIn in the show notes this episode and let her know that you heard about her on 30 MPC.

34:17Thanks for listening. We'll see you next week on the show. Today's show is brought to you by Proposify, the proposal management software designed to make every deal a closed deal. When you send a proposal to a prospect, include a video of yourself walking through the proposal because it's going to be shared with stakeholders beyond just your champion. You want to make it easy for those other people to digest and you want to be able to control the narrative with your presentation. And bonus, Proposify data shows that when buyers watch the video, it increases your chances of winning by over 3x. So do not let your proposals become a disappointing plot twist.

34:46Get our proposal success guide free in the show notes. Today's show is brought to you by Ambition, the coaching and performance platform helping sales leaders turn metrics into action. Did you know that sales orgs where the majority of reps are coached weekly are twice as likely to see high quota attainment than those who don't? And that is from Ambition's new state of sales coaching report that also found teams using a system like Ambition coach almost 60 % more frequently than those who don't have one. Now we built a toolkit with our friends in Ambition on how to actually use data to coach your team.

35:12Get it for free in the show notes. Today's show is brought to you by Pipedrive's easy to use and customizable CRM with built-in meeting intelligence. My favorite discovery question is the multiple choice question, which sounds like typically when I'm talking with folks like you, they're focused on A, B, or C, which is it for you? Now, A, B, and C have to be problems that you can solve because that's how you steer the conversation in the direction of places you can help them. Now, Pipedrive's built-in meeting intelligence helps you focus on your follow-up question, not on scrambling to take live notes.

35:40And we built a full discovery toolkit with them free in the 30MPC closers hub. There's a link in the show notes.

From the publisher

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Tara DiCristo-Schmitt breaks down the tactical sales leadership systems she uses to build predictable pipeline, coach reps, and create a culture of accountability. Learn how to inspect rep calendars, run better pipeline reviews, and catch performance problems before they hit quota.

📅 Eliminate calendar white space: Review reps’ calendars weekly and build two weeks ahead with net-new meetings, referrals, target accounts, and prospecting blocks so cancellations don't kill pipeline.

📊 Track “Days Without” key activities: Identify the leading indicator that drives revenue, then track how many days reps go without it to trigger coaching before performance slips.

🔍 Make pipeline reviews teach discovery: Ask the same qualification questions every week so reps learn exactly what they need to uncover from buyers and stop filling gaps with assumptions.

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