#601 - How to Build a Sales Team That Manages Itself | Tara DiCristo-Schmitt
35m 58s
This episode presents a practical, results-driven framework for sales leaders to improve performance through three core practices: the "Pledge" questions to validate buyer intent, "White Space Rigor" to eliminate calendar gaps and ensure consistent prospecting, and "Days Without Report" to create real-time accountability for key activities like demos and proposals. These tools are implemented through weekly, structured reviews where reps and managers collaboratively examine calendars and pipelines. The leader’s role is not to micromanage, but to model behavior and build culture—starting with open, respectful calendar checks and reinforcing consistency through repeated questioning. This approach empowers reps to self-manage, identify gaps, and take ownership of their sales process. The framework is scalable from rep to director levels, with VP visits ensuring leadership accountability. A common mistake highlighted is sales leaders overstepping by handling deals themselves, which undermines rep development. The result is a sustainable, high-performance culture grounded in clarity, consistency, and trust—where reps are equipped to deliver on their own, leading to better pipeline health, increased conversion, and long-term success.
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 don't 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 me,
say, hey, tell me how many demos did you have on there?
You know, they'll start to walk you through.
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.
Good 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 Howe's formerly the VP of Small Business at HubSpot,
formerly a sales leader at Paychecks, ADP, Holy Cow, Weve.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 work 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, what build in this report now.
We talked about pulling up calendars with your reps and live filling them out.
We talked about doing that with your, your frontline manager is also, you were 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.
All right.
One, I have the pledge.
The pledge is a clear expectations that allows reps and managers to know if we're selling
to suspects or prospect.
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 pipeline.
So I designed these questions to make sure that our managers are having the right pipeline
calls or conversations with reps.
Now here's the trick of this.
As 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.
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.
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 have 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?
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, 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.
What 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.
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.
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?
Calendar, white, space, rigor.
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.
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.
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.
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, we'll sit with the rep, open the calendar and
there's the 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?
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 listing.
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.
What's number three?
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.
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.
Hey, I noticed that you've gone X amount of five days with added 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.
It's not a blueprint.
It's not a urine trouble.
It's say, 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.
The right conversation.
Do you have the plan?
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.
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, it's always looking at my calendar and seeing that I'm not doing
a demo every two days.
Wait, five days?
Again, why are they all on my back?
How are you managing the feeling of micromanagement, the feeling of like, oh, you're all up in my business
and not let me do my thing?
It's a great question and it's not 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 22 today.
Exactly.
Exactly what you end up finding.
So the one that you implement, but 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, like, I absolutely know, everybody's busy,
everybody's doing more than they could, they could be doing.
And I mean, you can, 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 CEO,
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 and I say, can you open up your calendar?
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 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.
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.
And so you then just start asking, you say, hey, tell me how many demos did you have on there?
And they'll say, oh, they'll start to walk you through.
And you'll say, okay, so can you walk me through the 13 and tell me the the output of those
meetings?
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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.
You 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.
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And then what happens, that director and the manager will be in there as well and the
reps are to see, oh my goodness, I went into the week with a really solid plan.
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?
What targets can you always go that well though?
You got to have the rod that like 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.
So I'll tell you.
Okay.
So I'll give you, you want a real story?
Yeah.
Well, we love the real stories.
I mean, that was a real story also.
Give me a make one.
Make one.
Right.
Right.
Let me give you a real story where we're 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.
So in the past, so I assumed it would work very well in this 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 when you are, I'm still willing to help you because you're
the 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 not, you know, okay, that's not why I figured that they were going to put
time back on my calendar.
What I got instead was a call from HR.
Well, 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?
I guess, 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'll tell you something
about that same rep.
That same rep was the top rep for six years, the company number one for six years.
The year I happened to step in, that rep was not going to hit presence club.
Not only were they not going to be number one, they were not going to make presence 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, different businesses, ADP, paychecks, 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?
You'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.
So in a 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.
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 and age is we are adding activity, right?
We are adding the right activity to our, 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 a brand maybe a little longer than that, but let's just say somewhere
in that 45 day range, it was seven, 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 opened up my slack to you right now, it was the exact dialogue
I had with our head of sex.
And actually, here's what will make you laugh.
I said to her, have you put this in cloth to see if this can be automated?
Not because I didn't, 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 cloud 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.
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 file the exact same process, so I would have the first note go from the director
to the manager.
I had 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.
Now daily, so everybody can now see it.
So what ends up happening is a rep opens it up, they use them a few 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 so you've created a high performance culture of people managing themselves to the work
they need to do every day.
And you know, like that's the secret to it all.
When I know who I am and I know what I need to do to do, I go do it.
Yeah, what's 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 are 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.
And that's, I think that's that's that simple stuff that like as a leader helps you now.
You have this, you have days without, I'm stealing that 100%.
Then you have this other, 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.
But when you said 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 buyer
or are you checking on the answers?
Like tell me the logistics of how you coach that
in the deal review.
- Yeah, so the pledge comes into the know your business,
deal review, pipeline review, right?
I always say, do you know your business?
Like that's kind of the idea.
Like you want, when you're 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?
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 what 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, OK, 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 run off.
Right?
So 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, once I, if they do have the answer
to the business objective, I say, OK, 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'll listen 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?
Mm-hmm.
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.
Because I know I've sat in the rep seat
where I get asked the question.
And I'm like, OK, 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?
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 Full and Rich,
which compiles 20 plus premium data vendors in one place
to dramatically improve your call-connect rate.
When you're cold calling, you have
to make sure you're not showing up as spam-likely
on your prospect's end.
And one way to do this is to stop calling bad numbers
over and over again.
Mark your disconnected or fax lines or wrong numbers
so you know not to dial them again.
Or even better, make sure your data provider only
gives you verified numbers to start with.
We partnered with Full and Rich on a guide of nine ways
to improve your call-connect rate.
Get it for free in the show notes.
Today's show was brought to you by Pipedrives 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, Pipedrives 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 30MPC Closers hub.
There's a link in the show notes.
Today's show is brought to you by 11X.
You're all in one digital GTM team handling, creating,
qualifying, and converting pipeline across every channel.
Can you tell the difference between a positive answer?
Oh yeah, they really want this, this, and this.
And you're like, no, that's not true.
'Cause sometimes I don't think most reps go in
thinking, I'm gonna 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 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.
You know what I mean?
A lie says valentine.
They're not there to deceive you most of them.
- No, I would say they're never there to do that.
What would be, do you know 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 with that?
- Right.
And they'll be like, I don't know,
I gotta go back and ask.
And I'm like, all right, well, let's go back and ask.
'Cause then I'll say, why is it important
that we know the challenges that they think they're gonna face?
And then you'll hear me.
And I'll say, all right, so let's figure them out.
And then I'll often say, you wanna call now?
Let's call 'em together.
- Ooh, ooh.
- Grace, 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 don't want you or they don't know how.
And so you gotta give them the confidence
and the confidence 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 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.
And like, you're doing that, you're modeling that.
But like, I don't know if you're explicitly telling people
that, but 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 really what I'm hearing from you
is it is coaching, but what I'm hearing
is this 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 gonna show you,
I'm gonna show you, I'm gonna show you.
And then that breeds people to know what to do
and how to do it, right?
And then you can move this stuff out of their way.
- I wanna 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 like their pipeline coverage against their quota?
Are you asking them to give you a sense
of like new pipeline that's been generated?
Are you asking them to give you a sense of like,
hey, based on my territory,
here is how much coverage I have against the territory
versus accounts I haven't touched at all.
What actually goes into this Know Your Business Meeting?
'Cause it sounds like it's bigger
than just a traditional pipe review if I'm not mistaken.
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 that, 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 hey, let's grab, let's take a look at it
at your business and I pick one
and you go through the Know Your Business.
Because you don't want to lose that coaching opportunity
that comes out of the Know Your Business.
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 what deals came out
because you decided that these deals were not,
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.
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 your VPs with your directors?
I'm curious about the leadership white space
selling 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.
Like for example, I'm going to do CRO visits in June.
And so it starts from the top down
and part of it is saying, let me 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 the open up, 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.
They're spending it everywhere else.
Directors are spending time, not customer facing,
not rep facing, not coaching managers and inspecting.
So I design the director, called the director and VP visits
so that they can get in and inspect what they inspect.
So build the calendar out.
What 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 week?
And so yes, it's more monthly with the director
and the manager calendars.
Sometimes even quarterly depending on where they are
and the org, but the rep one is weekly.
Are there certain things that you are suggesting
that managers or directors caught from their calendar
to make room for other things?
Internally, right, other parts of the business
will have several calls to get to an end game.
And the sales leaders will, I will find
that they'll be sitting in those multiple calls.
And I'll say, OK, there's four calls this week
on the same top.
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 not, which one 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?
I 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 things that are just really cool.
I don't think I have anything else.
Cool.
All right.
Well, then we got to move through 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
some more than it helps.
So I think them being super reps.
They want to be the super here.
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 what's ever happening with their deals.
And I think that is funded that is a fundamental flaw in a lot of sales
cultures that I have inherited over over the years.
Sales leaders should be coaching and coaching and repeating 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.
Out of market is time for your two by two recap.
What 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 in 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.
What 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 over week over week of like, these are the things that add
prospecting, prospecting, do your call 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 your reps, micromanage themselves.
And there's nothing better than a rep that manages them themselves.
Yes.
So my two were the first one is, let's call them.
So you're on your high-preview.
TD calls it, uh, uh, know your business meeting.
Uh, 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 that they don't know what to do.
They don't know how to do it or some things in the way.
This literally here on the review, you got time.
So 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, we're 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 a 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.
So downstream, the rep knows every deal I'm in, I'd better have the answers to these questions
because I know my manager is going to ask me this.
This 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 customer is 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 higher.
If you want to work for a world class sales leader, send her a note on LinkedIn.
We'll put her LinkedIn in the show notes this episode and let her know that you heard about her on 30NPC.
Thanks for listening.
We'll see you next week on the show.
Today's show is brought to you by Fullenrich, which compiles 20 plus premium data vendors
in one place to dramatically improve your call, connect rate.
One way to do this is to stop calling bad numbers over and over again.
We partnered with Fullenrich on a guide of nine ways to improve your call, connect rate, and get it for free in the show notes.
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Podcast Summary
Key Points:
The "Pledge" framework uses standardized questions to help reps and managers identify true buying signals by asking about motivations, business objectives, challenges, alternatives, and decision-making processes.
"White Space Rigor" involves weekly calendar reviews with reps to eliminate idle time by scheduling net new appointments and strategic referrals, ensuring consistent, productive activity across the week.
"Days Without Report" creates real-time accountability by monitoring gaps in key activities like demos or proposals—triggering managers to intervene at 2, 5, and 10-day intervals to restore momentum.
Leaders must model calendar transparency and build trust before asking reps to open their calendars, starting with a respectful, collaborative approach to avoid perceptions of micromanagement.
The sales process is reinforced through consistent, repeatable questions during pipeline and deal reviews, enabling reps to internalize best practices and self-manage their pipeline.
Leadership accountability extends to directors and VPs through "VP Visits," where leaders inspect calendars and time allocation to ensure coaching over task delegation.
A core flaw in sales leadership is over-involvement—sales leaders often take on rep responsibilities, undermining autonomy and long-term rep capability.
The combination of structured questioning, calendar rigor, and consistent coaching builds a self-sustaining, high-performance culture where reps manage themselves effectively.
Summary:
This episode presents a practical, results-driven framework for sales leaders to improve performance through three core practices: the "Pledge" questions to validate buyer intent, "White Space Rigor" to eliminate calendar gaps and ensure consistent prospecting, and "Days Without Report" to create real-time accountability for key activities like demos and proposals. These tools are implemented through weekly, structured reviews where reps and managers collaboratively examine calendars and pipelines. The leader’s role is not to micromanage, but to model behavior and build culture—starting with open, respectful calendar checks and reinforcing consistency through repeated questioning.
This approach empowers reps to self-manage, identify gaps, and take ownership of their sales process. The framework is scalable from rep to director levels, with VP visits ensuring leadership accountability. A common mistake highlighted is sales leaders overstepping by handling deals themselves, which undermines rep development.
The result is a sustainable, high-performance culture grounded in clarity, consistency, and trust—where reps are equipped to deliver on their own, leading to better pipeline health, increased conversion, and long-term success.
FAQs
The Pledge is a set of standard questions used to assess if a customer is a true prospect or suspect. It helps reps and managers identify real buying intent by asking about business objectives, challenges, alternatives, and decision-making processes.
The 'Days Without Report' system tracks how long a sales rep goes without key activities like demos or proposals. If a rep misses a threshold (e.g., 2, 5, or 10 days), it triggers a manager to check in and help the rep regain momentum.
White Space Rigor involves weekly calendar reviews with reps to fill their schedules with meaningful meetings. This ensures consistent activity, prevents burnout, and creates a structured plan for each week.
Managers conduct random pipeline reviews using the Pledge questions to assess whether reps truly understand their customers’ needs. This helps detect assumptions, improve discovery, and build consistent sales conversations.
Opening a rep’s calendar helps leaders see actual activity, identify gaps, and understand where planning or execution has failed. It creates accountability and leads to actionable insights for improvement.
Leaders (directors, VPs) conduct calendar reviews to assess how time is being spent, ensure coaching is happening, and identify inefficiencies. These 'VP visits' help build a culture of transparency and accountability.
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