Longer sales cycles and slow pipelines.
That’s my theme for 2025.
How can you rev up your engine and move deals through faster?
Let’s talk about it on today’s episode of Closing Time.
Thanks for tuning in to Closing Time, the show for Go to Market Leaders.
I’m Val Riley, head of marketing for Insightly and Unbounce and LeadsRX.
Today I am joined by Nick Cegelski.
He is a sales coach, author of Cold Calling Sucks
and CEO of 30 Minutes to Presidents Club.
Nick, welcome to the show. Well, thank you for having me.
I really appreciate it.
You’re a multi time offender on closing time.
So you’re in a very select group.
You know, I do my best to offend.
What can I say?
Okay let’s jump right in.
Because Nick I’ve already shared with you this is on my mind.
I think it’s on the mind of
a lot of sellers and sales leaders under normal circumstances,
pipeline velocity is always going to be top of mind for a sales leader.
Right? Time kills deals.
But what’s happening in the market right now
that you’re seeing that’s making it especially important right now?
Well, I think there’s a lot of uncertainty that folks have around, like,
where the economy is going to go.
I think that you have a lot of buyers that know that
they have leverage in deals, and they know if they say, hey, you know what?
We’re going to kick this to next quarter.
A lot of sellers will drop their pants and be like,
we can give you a discount if you close sooner.
We were talking about
like tech sales and particularly. I think there’s a lot of folks that,
like buyers generally know if I wait till the end of the month or if I wait
till the end of the quarter, or if I say, hey, I’m talking to competitor
B over here, they do everything you do and they’re half the cost.
What can you do for me?
It’s really, really tough.
So I think there’s a lot of pricing leverage that buyers have.
I think there’s a lot of uncertainty.
But that doesn’t mean there aren’t ways that you can accelerate
your deals and move them faster, not only through your process,
but move them faster through, relative to your competition.
And I think that’s one underrated thing for a lot of salespeople, where
if you’re in a bake off against 2 or 3 competitors, one differentiator
in the deal is if you let’s say it takes. I used to sell ERP software,
and we would do anywhere between 10 and 20 meetings
over like a six month process with these folks.
If we could get through a material number of those meetings
faster than the competition,
they would get to the point where they’re like,
look, we’re already so deep with Nick’s company.
Like, let’s just do that.
It feels like it’s a good solution
when you get the first mover advantage in the deal when you do those things.
So we’ll talk about some of that.
I know we’re going to go through a bunch of ways
that we can compress and accelerate our deal cycles.
Today in rapid fire format, and I like rapid fire format.
Awesome. Let’s do it.
I didn’t know you had an history in ERP.
So I’ve learned something new about you already.
Oh, it was a lot of fun.
I sold ERP systems to law firms.
And so a lot of talking to like attorneys and CFOs.
I don’t have a legal background.. I don’t have a accounting background.
But I did okay for myself.
I figured it out.
Oh, that contract review process was probably murder, though.
Well, I’ll have to talk about that over a beer one time.
I could talk about that. Well, let’s let’s put a pin.
That’ll be one of the last ones.
I share how you can speed up your contract review process.
Awesome.
Okay, well, I want to start with, tips for cold calling, because I think one tip
you had here to really get that pipeline moving is to get that meeting.
So you’re on a cold call.. They agree to a meeting.
You want to get that meeting booked as soon as possible.
Yeah. So let’s just go.
So let’s structure this as it relates to stuff
that we’re doing from like a prospecting and early stage perspective.
We can do mid-stage tactics to accelerate your deal.
And then we can do late stage.
So early stage, the very first way you’re going to originate
your deal is picking up the phone and cold calling somebody or cold emailing them,
or you’re talking to them on LinkedIn, or you’re talking to them at a conference.
You’re meeting somebody in person.
You’re going to get to a point where someone says, you know what, Nick?
I’ll take a meeting with you.
You want to schedule that meeting as soon as possible instead of saying,
great, well, how does this time next week work for you?
I’m going to say, great, Val, how does 3:00 today work for you?
Or how does this time tomorrow work for you?
Now, if you’re prospecting to people that are in the C-suite,
they’re probably going to have a stacked calendar
and they won’t be able to meet the next day.
But what you do here is you anchor them to meeting sooner rather than later.
So instead of them being like, yeah, let’s meet in two weeks,
when you say, hey, how’s later today or tomorrow work for you,
they’re going to be feeling weird to be like, yeah, actually, let’s meet in July.
So try to anchor the meeting sooner rather than later.
It’s not foolproof.. It’s not always going to work.
But generally when I’m booking next steps, my goal is to book them
as soon as possible.
This helps
not only with compressing the deal cycle, because the meeting literally
happens sooner.
It also helps with creating momentum
in the deal, which I think is an underrated thing for a lot of folks.
So that’s as it relates to prospecting and booking the meeting.
If you’d like,. I can talk about the next one,
which is what you do before you have a first meeting with somebody.
Yeah. Let’s. Let’s jump right to that.
Because, you know,. I think people sometimes
get caught up in that research phase, right?
They’re they’re so excited.
And they want to prep for that meeting, so well.
You suggest sending over like, your
a point of view sort of document ahead of time.
So what’s it feels like that just puts the whole deal on fast forward.
What’s the particular benefit there?
Yeah.
So what I recommend doing is no hidden work.
And what I mean by that is most salespeople know
they should do some semblance of prep before their first discovery call
with the customer.
And what happens for a lot of folks is they put it
on a piece of paper like this one, or they put it in a Google doc somewhere.
They might even put it in their Insightly CRM
so they can look at that right before the meeting.
But that prospect doesn’t get the benefit of seeing all of that prep that you did.
What I usually will do is when I send my pre-meeting agenda to my customer
a couple days before,. I’ll include 3 or 4 sentences of
if I was selling to law firms, it would be something like, great, and by the way,
one thing that I think we’ll probably spend some time talking about is
I know you all just opened this new office in Tacoma, and you’ve got an insurance
defense practice group that it looks like it’s growing.
I know there’s a lot of complexity with like Washington state tax
and insurance defense building for your insurance clients.
We can help with some of that stuff, but that might be one area.
We talk about.
That was maybe a little more long
winded than what. I would actually write in the email.
But the gist of this is you want to show that you’ve learned some stuff about them,
and you’ve got a suspicion of some of the areas that you might talk about.
What happens when you do this is you’ll get on the call with the customer,
and instead of them having to start at square one
and spend the first eight minutes being like,
just so you know, we just launched a new insurance defense practice group,
and we have a new office that we opened, and they’re taking you through the basics.
They’re like, hey,. I looked at what you sent.
Those things were right.
Here’s some more context or here’s what you missed, or here’s what you got wrong.
It’s actually not bad to be wrong because people like correcting you.
And when you show that you did your best, folks will give you those
like they’ll be like, great, this person is at least trying to meet me
somewhere as opposed to they don’t know what they’re getting.
When they meet a new seller like you.
They might be they might think you’re somebody who has zero context whatsoever.
So I like sharing
that point of view to accelerate that first discovery conversation.
It would make me feel as a buyer that someone, that this person
did their homework, invested in the,
in the time that we’re going to spend together.
So I really do like that tip.
Val, you probably by a lot of different things.
I mean, you’re leading the entire marketing organization
at a fairly large company.
How would it feel for you if somebody was half right,
half wrong in sharing that point of view?
Would that make the deal blow up in your mind?
Or would you say, hey, this person like they showed, they learned some stuff
and they did their best.. I’m going to correct them.
What sort of.
Maybe that was a leading question,
Well, it’s instant respect for the because I respect the hustle.
Right.
And so it’s just instant respect for the hustle even if it’s wrong
or 75% wrong.
It’s like hey this person at least you know did their best.
So so yeah I’m sold on that.
Yeah, I love it.
Cool. Well, you validated me a little bit.
All right. Good, good.
So I have another step here.
Another tip, about increasing pipeline velocity.
You sort of alluded to this, but, same day next steps,
which I love because I do feel like we reached the end of the call
and it’s like, okay, well, you’re going to talk to Bob and so-and-so
is going to check on this, and we’re going to get
and then all of a sudden, like, we’re two weeks out, right?
yeah.
So I’m going to bundle number three and number four together,
which is when we’re talking about setting next steps
so similar to the prospecting one which is the goal
is to try to get the next step as soon as possible.
Even if you can’t get it the next day,
you want to anchor them to meeting sooner rather than later.
I want to book the meeting as soon as possible.
Makes sense.
The other thing that you want to bundle in with this one.
So number four, is if I know
there are other stakeholders in the deal who are going to need to be involved
in whatever that next step is,. I’m going to name drop those people.
So what that requires me to do when I’m prepping for the meeting is
I might need to look up who is on your team.
So, Val, if you were my customer and I always have a meet
having a meeting with you, and the next step was
we were going to go through a couple different campaign ideas for how
we might promote the new copilot elements in Insightly,
I wouldn’t just say,
all right, Val, well,
why don’t we go through those campaign ideas tomorrow afternoon?
I would, and I wouldn’t say, well, we should probably involve some folks
on your team who are on your team.. Do you want to involve?
I would say, hey, I think Courtney on your team handles a lot of, like, the
marketing operations and back end stuff and some of like the content production.
But my guess is it probably makes sense to get her involved.
Do the two of you have some time tomorrow afternoon?
And when I namedrop Courtney, it just like it does something to your brain,
you’re like, oh, this person gets it.
They know my org, they prepped and it’s easier for you just to say yes.
Then if I say, can you think through who’s on your team
and who you’d want to involve them?
So I make it easier for you.
I reduce like the friction and the cognitive load on you,
figuring out who you have to involve.
So I love name dropping the human beings that I’m going to involve
in the next step, or I think should be involved.
I love that tip.
Kind of continuing on there.
If there is, you mentioned if there might be some additional,
work to be done with some stakeholders.
You might, in between first and second meeting, actually
reach out to each person and maybe do, like, a short mini discovery.
That sounds like a lot of work.
yeah it does.
But it actually,
again, we’re doing the work to compress and consolidate our sales cycle.
That work is going to happen eventually.
So let’s carry that example on.
So Val, you’re my customer. I just had a great meeting with you.
We now have a meeting for let’s say it’s a Tuesday.
We have a meeting for Friday, and it’s you and Courtney.
What I’m going to do before that meeting, while I’ve already talked with you,
I’m going to pick up the phone.. I’m going to call.
I’m going to call Courtney.
I’m going to say, hey, I’m prepping the custom demo for this Friday.
I already had a conversation with Val, and she cares about A,
B, and C, but I really want to make sure that this thing is tailored to you.
Also in this, it’s on the stuff that you care the most about.
I’m going to call her and I’m going to say that if she doesn’t answer, I’m
going to leave a voicemail, and I’m going to say that,
and I’m going to email that in between now and that meeting on Thursday or Friday,
whenever I said it was my goal is to get on with her.
She might just respond with a couple bullet points,
but I almost want to do some pre discovery with Courtney.
And what often happens is,. I had to do this a lot when I was selling
to law firms where you’d have some fairly,
litigious or challenging to win over attorneys
and they would just get in the room, we’d get eight attorneys in the room,
and they would argue for 45 minutes of the hour long demo about,
do we even need something like this?
I’m like, oh, this is so frustrating.
And so what I learned to do is. I would call each of them in advance, win
each person over one by one by one.
And then when you get people in the room because you’ve addressed
their specific concerns and needs on the one on one call,
which is more respectful of the time of the other people
because they don’t have to sit there
and listen to a conversation that’s tailored to Dave and not Jane.
You get in the meeting and everyone’s already won over,
or at least you have a much sharper sense of what the collective group cares about.
You can’t do that if you don’t have that previous recall in between meetings.
I love that.
I mean, honestly, Nick,
that one feels like it would just put that deal on hyperspeed.
Because, you know, you’ve address concerns, you’ve gotten
consensus in between calls, which is brilliant.
Like you’re actually using that space in between calls.
I think a lot of sellers are afraid to pick up the phone and call their buyer,
and you have to frame everything from the perspective of why it is in
the buyer’s best interest to participate in whatever you’re trying to do.
So if I’m calling Courtney and I’m like, hey,
we have a demo on Friday,. I just want to call to check in.
She’s like, the heck are you checking in about?
I have to frame it from the perspective of,
I want to make sure this is valuable to you.
So any time I’m asking my customer to take action, to do work,
to engage with me, I have to frame it in terms of why it’s in their best interest.
Right.
It really shows up, Nick, as a respect for my time, as, somebody who’s
attending that meeting and someone who’s a stakeholder in the project.
So I really like that one.
We’ve got one last one. Number six.
And I love this one because, honestly, sometimes I’m just running from call
to call to call with internal meetings and vendors, and I oftentimes
don’t have time to read my notes just before a call starts.
And it it sometimes, admittedly,. I’ll be 2 or 3 or even five minutes
into a call before I’m remembering the context of of why we’re meeting.
So you’re suggesting that the vendor open a call
with what I heard last time and then do a short recap.
Yeah.
I kick off every group meeting, especially if there’s new stakeholders
with a slide with, like, 2 to 4 bullets of the biggest things
that I heard they cared about in the beginning of the deal.
And I spend three minutes,
if that recapping one, two, three, four.
And then if there’s a new stakeholder in the room,
I use that as a reason to open up the floor for conversation.
So I’ll recap the things that I heard last time, and then I’ll say something
to the effect of,
so these are the notes that I have and talking with Val and Courtney.
But Michael, I haven’t really had an opportunity to connect with you.
I’m curious, is is this how you also see the world?
And what this does is
you talked about respecting the hustle earlier? Val,
if I show as a salesperson that one when you talk, I listen.
When Val and Courtney shared stuff with me, I listened,
I wrote it down,. I put it on a professional looking slide,
and I spent three minutes of this meeting catching everybody up to speed.
It’s really,
really hard for someone to be like, well, I’m not going to tell you my answer.
Like they’re going to be like, okay, like this.
This person’s doing their best.
Yeah. Nick, I’m happy to tell you.
Here’s where I agree with what Val and Courtney shared.
Here’s some other context for you.
It’s a great way to open people up, because folks will reciprocate
the level of effort that they see from you.
You might be a sales person who’s preparing really,
really hard for your conversations, but if they can’t see that
and the slide is a really, really great way to do that, it’s not real to them.
So that is one of my favorite ways to like open up the room and accelerate.
The first part of that meeting, because then you get everybody on the same page.
You accelerate the discovery where Michael, in this scenario doesn’t
have to catch me up to speed on the basics because he can see what I already know.
It’s on the slide now I’m getting level three, 4 or 5 stuff
instead of level 1 to 3 stuff, because I show that I already knew that.
You’re also at the same time really building consensus,
making the people on the call feel like, hey, we’re all a team.
We’re all trying to accomplish the same goal.
Nick’s part of our group.
You know, he’s trying to help us as well.
So I just really like that aspect of just consensus building. Yes.
So, Nick, those were six great tips.
I do, I love them all.
I do feel like what you’re doing is creating urgency as the seller,
and then you’re inviting the, buying committee to kind of match that urgency.
And that’s the tip to really moving deals through the pipeline.
Did I summarize that pretty well?
I think you directionally got it right.
I think one other piece of context that I would add is
there’s a quote that I really like, which is the fastest way to get
the right answer to something is to post the wrong answer on the internet.
You go on Reddit and you post the wrong answer to something.
You will get corrected very, very quickly.
There’s a similar phenomenon in your sales process
where if I suggest Courtney on the next meeting,
if you’re like, no, no, no, no, no, it’s not Courtney, it’s Michael.
Well, great.
I still got what I wanted, which is the person that we want
on the next meeting.
But if I just say who should we involve?
It’s harder for you and you might say, hey, let’s just keep this one up.
If I suggest meeting tomorrow, it’s a lot easier for you to just correct
me and react with the time that does work for you versus if I say, well,
when do you want to meet? You might say, yeah, let’s, let’s meet in two months.
We’ll shoot.
If I suggested tomorrow, you still might say, nope.
I don’t have bandwidth for the next two months, but at least I gave it a shot.
So oftentimes
folks will follow your suggestion because it’s a path of lowest friction.
And so my recommendation is find ways to suggest moving faster
and let them tell, you no.
You’re doing this in a respectful way.. This isn’t a pushy way.
You’re just suggesting hey, Val, if you want to solve this problem.
If you want to make the problem
that my product makes go away, like, let’s get this thing done.
And if you have a different timeline, you can tell me that
I’m not trying to box you in a corner or be a pushy jerk.
I am trying to say, hey, if this getting getting this problem
solved now really matters, I’m here.
Let’s do this thing.. I want to match your level of urgency.
I love it.
All right, Nick, thanks so much for joining us today on Closing Time.
I want to remind the folks out there you authored the Ultimate Guide
to Managing your Pipeline.
Co-authored that with, the Insightly team.
And so we’re going to put a link to that in the show notes so people can grab
that if they want to catch any more of your insights.
It’s insightly.com/30MPC.
We’ll put that link in the show notes.
Where can folks find you if they want to follow you, Nick?
Well, I would recommend maybe if you like what you heard today.
One. Go get that guide.
Because we have a lot of stuff in there around accelerating pipeline,
not only as a rep, but some ways you can do it as a leader with your team.
So I would check that thing out first and then I’m on LinkedIn.
So if you send me a LinkedIn connection request,
as long as you don’t send me a really canned spam message,
maybe give a shout out to the Insightly team
and let me know that you heard me here,. I’ll accept your connection request.
Awesome.
And thanks to all of you for tuning in today.
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