Beyond the SKO: Future-Proof Your Sales Approach to Win More Deals in 2024

Whether you call it SKO or S-K-O, the season is upon us.
Let’s talk about sales kickoffs in this episode of Closing Time.
I’m Val Riley, head of content and digital marketing at Insightly CRM.
Today, I’m joined by Geoff Hendricks.
He’s an AE at Challenger, a sales coaching business and a double podcast host.
Welcome to the show, Geoff.
Thanks, Val. It’s great to be here today.
Geoff, we were both at sales kick offs recently and I just wanted to see
what types of themes you’re hearing in terms of sales kickoffs in 2024.
Yeah, Val, well as any good sales kickoff is want to do,
I think that pipeline generation is always top of mind.
But I think what was really interesting, not only at our own SKO,
but what I’m hearing out of a lot of sales leaders
is not only a focus on pipeline
creation, but on pipeline validation and the consequences
that they were feeling towards
the end of last year of not having confidence in their pipeline
and how much it was impacting their forecast accuracy.
Yeah, I did hear a lot about that.
Just it kind of shows up in stalled deals.
Is that typically where you see it?
I think so.
You know, it’s definitely one of the challenges that we see across the space.
A lot of folks were really, really accustomed to having a predictable win
rate and being able to know more or less where things were at and,
you know, sort of the law of averages figure out what was likely to close.
And I think what a lot of sales leaders experienced last year
were those sales are those win rates declining.
And a lot of to your point was because a lot of those mid
to late stage deals that sellers were forecasting
started to fall out
a little bit more and sellers were not being able to predict
accurately which of those were likely to close and which weren’t.
So it sounds like maybe some hangovers
from 2023 are, you know, sales velocity.
Anything else that you’ve seen in terms of things
that we might be bringing in from 2023 that we’d rather not?
You know, I think if there’s one thing that I think everybody can agree
upon, it’s that the buying environment is more challenging.
And I have a lot of empathy for buyers out there
because buying is almost a full time job and they also have
their own full time jobs.
And so what’s interesting is, you know, as budgets were certainly tightened
last year as there was additional scrutiny and spend, a lot of the weight
fell on the buyer shoulders to try to figure out if they could drive consensus
and I think that was, you know, if
we think of sellers from our perspective, the stalled deals were frustrating.
But from our buyer’s perspective, it was also frustrating because a
lot of folks were encountering situations that they weren’t accustomed to.
They weren’t able to get their
organization to say
yes, because folks frankly, didn’t want to make a mistake.
And that’s how tight budgets are today.
That even resonates with me as a buyer in the MarTech space.
You know, for instance, you know, being asked to be challenged
by the finance department or, you know, being asked
for more favorable payment terms, you know,
it is challenging as a buyer sometimes because you want to move forward.
You feel like this is a positive step for your organization,
but you are being questioned by, you know, your leadership
or your finance team saying, how can we make this more palatable?
You know, do we really need this?
All those questions, it really does put that buyer in a tough situation.
And, you know, as sellers,. I think that it’s our job to think about
what are some of the things that we can do
that can take some of the weight off of our buyer’s shoulders.
And, you know, if I think about how we transition
into next year, that’s where I think a lot of the focus is in order
to make sure that we’re engaging with one the right buyers
and that we’re also making their jobs as easy as possible.
Yeah, that’s a great skill for a seller to develop.
So speaking of skills that sellers may develop.
On your podcast, I think you take a really fun angle in terms
of talking to sellers and you ask them as sales leaders and sellers in general
what their biggest mistakes or misses are in their career.
Tell me about that approach, because I think it’s super interesting.
Yeah, I think, you know,
so what’s really interesting is. I did an entire career in consulting,
and this is actually the first time. I picked up a bag, so to speak.
So this is my first sales job.
And, you know, you go on LinkedIn and you see all these people giving
usually great advice,
not all of it’s great, but let’s let’s filter for our favorites.
And you just think, wow, these folks have it all figured out.
But you also realize they’re ten, 15, 20 plus years into their career.
And there’s a reason they have it figured out.
And what I love about this is it also brings in a classic
like psychological concept that I love, which is called prospect theory,
and that is around loss aversion.
But I translate this to like, think about, you know,
when you made a mistake, was that more memorable
or was when you got it right the first time more memorable?
And personally, for me, it’s all about,. I think, back and I think those mistakes
really stand out.
And they’re impetus, they’re reason for changing our behavior.
And I love to uncover
what some of those were so that folks, you know, as they’re 15, 20 years in,
can tell us how they arrived at the place they are today.
And so that’s the whole thing behind it, because I just I feel like, folks, one
need to understand like what’s behind a lot of the advice that people give
and that these people aren’t perfect and two that, you know,
even if we make mistakes along the way, those of us who are a little bit earlier
in our in our sales careers,
we have the opportunity to learn from them and to get better.
That’s so true.
I’ll share an experience as a software company.
One time we were in an RFP process
and one of the questions was tell us about an implementation that failed.
And I thought that and I’ve done a lot of RFP in my life,
but that question really forced us to like, stop
and be introspective and give a candid answer.
And I really do think that that buying committee
probably learned a lot about all their potential vendors
just from that question, just from asking about a failure.
I love that question.
It’s kind of like an interview question.
And you really it makes you stop and think about it and hopefully
give a below the surface level answer.
Yeah.
So let’s switch gears a little bit and talk about Challenger,
because really Challenger is about looking at high performing sellers
and there are some out there for sure and what they’re doing well.
So can you give me some background about how Challenger got started?
Yeah, absolutely.
So it’s funny, there are some pretty good parallels to today.
If you think about the last recession we had.
Capital, budgets were even more tight because we were going through
the mortgage crisis and the banking crisis and all that.
And the company that we used to be with was called CEB,
and they had a membership and the membership
said, Hey, I’d love for you guys to study because we have this
small group of sellers that are not only hitting goal, but they’re exceeding it.
When the rest of our team is sitting at 40% of goal.
Like, what is it that they’re doing differently?
And so that was sort of the beginning of this whole Challenger thing.
It was like, let’s go out and study what these sellers were doing differently.
And I think there were two real key things that we discovered there.
Number one, we interviewed buyers and said, What do you care about?
What is it that makes you pick one supplier over another?
And essentially they said, like, look, company, brand, products,
service, value, price, all that.
That’s table stakes.
What really matters is the sales experience that the seller delivers
that they can show up with a perspective, provide me
some insight and help me corral all the people on my team to make a decision.
So that was the buyer’s perspective.
And then from studying the seller’s perspective, essentially what we learned
is that there are, you know, five profiles of how people tend to engage customers,
and four of those do very well in terms of being average sellers.
But one of, actually two of those profiles stand out in terms
of being disproportionate high performers, the lone wolf
who are really not sure what they do, but they keep hitting the numbers.
We keep them around.
And the challenger, which essentially delivered
that sales experience that the buyer was looking for.
And so essentially what we said is like, great,
if they’re these people with repeatable skills and behaviors,
let’s figure out a way to help the other profiles adopt some of them.
They don’t have to change everything, but if they can just adopt a piece of it
and figure it out,
they’re going to do better and they’re going to do better
for themselves and their families and their companies.
And so that’s essentially where the original concept came from.
And it led to Harvard Business
Review articles, bestselling books.
And essentially the company has spent the past decade
learning how to help organizations adopt those skills and behaviors.
I mean, it’s a universal need for sure.
Does the methodology look at certain parts of the funnel
or certain stages of the sale, or is it just all up and down across the board?
Yeah, that’s a great question.
I think first it starts with a mindset shift
and it’s really thinking about how I’m going to put myself
and my customers shoes, how I’m going to be
thinking about their business and the things that matter to them, rather
than focusing on my products, my solutions, or potentially
the ROI that I can be delivering to folks.
So first it is thinking about thinking in a little bit of a different way.
But if you think about it, you can apply that mindset shift anywhere
across the sales process, whether you’re
doing top of funnel activities, you know,
cold outreach, engaging with folks, preparing for a discovery meeting.
They’re all activities I can do that
put myself in that buyer’s shoes and makes me think about their world.
And on the back end, if you think about kind of that mid-stage
or closing process, I’m thinking about how can I ensure that we hit the dates
and the key things that matter to my customer and work back from there
and what things can I take off their plate to make, you know, contracting easier,
to make procurement easier and essentially be the professional seller
that makes my buyer’s life better and easier?
Yeah, that’s super insightful.
We’ve been talking on a few episodes on Closing Time
about how sellers can de-risk the buying process for buyers.
You know, showing empathy to the sellers concerns about,
you know, not wanting to
pick a poor product or have a failed implementation
or a failed project associated with them for, you know, a long time.
Is that part of the Challenger methodology?
Absolutely.
And so it’s really interesting, Val, is, you know,
essentially one of the key pieces that that can really earn you trust
is to be able to coach a buyer around the potential pitfalls.
If we think about it, you know,
they’re buying your product or service probably once every, what,
three years, give or take more or less, maybe, maybe even less.
And you live and spend every single day in that space.
And so what are some of the common mistakes that you see
that they would appreciate being coached around to avoid?
And so that’s definitely a key piece to the skills and behaviors
that we’ve seen really help sellers shine in the in the eyes of buyers.
I know that topic
has come up in probably several sales kickoffs.
So it’s nice to hear that it’s addressed in the methodology.
So you know, you’re in the training business.
I have worked in the training business in the past and it is challenging
to get people to realize that training just doesn’t happen once a year
or at the seminar that learning, real learning, happens year round all the time.
What are some strategies that you might give to enablement teams
or sales leaders to keep them in the mindset
that learning has to be a year round occurrence?
Yeah, I love your point there because it’s so true and it’s backed up by science.
Essentially.
There’s something called
the forgetting curve, which is no matter how good a training is,
if it’s not reinforced, we lose a chunk of it.
And the stat is you lose 87% within 30 days.
So that’s a lot of learning loss if it’s not properly reinforced.
And, you know, I we just are coming out of our SKO and,
you know, the feeling, the energy, it’s amazing, but it tends to dissipate.
So what I would suggest if somebody is thinking about
how do I create any sort of shift, you know, whether it’s sales methodology
or any really change management perspective, is to look at it
from an organizational capability perspective.
And so in the case of, say, like a sales methodology, you’ve got
four key things that you need to kind of have rowing in the same direction.
You have your message.
So being able to provide folks an example of what a message is.
Those are not your features and benefits.
That is the things that matter to the customer.
Two, your managers are so important.
They are keys to coaching and reinforcing this stuff.
Getting them involved early
and often is essential so that they can keep this alive.
Number three, you got to teach your sellers
the skills and behaviors that you want, mindset and tactical.
And then number four, and this is where you guys come in,
you know, it’s making sure that your sales process, your CRM like Insightly
are aligned to what you’re asking your sellers to do, your hiring process,
all the different aspects of that, you know, are aligned
to what you’re asking them to do on a daily basis
so that it’s natural for these types of changes to start to stick.
So, yep, sales leaders, if you’re out there, you know, take
that heed and make sure you are, you know, keeping learning
at the forefront so that you continually develop your team.
Geoff,. That’s all the time we have for today.
Thank you so much for joining us.
Oh, thanks for having me.. It was a pleasure.
And thanks to all of you for tuning in to Closing Time.
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