Closing Time

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

Sales kick-off season is upon us. Whether yours is virtual or live and in-person, get ready to be inspired.

Geoff Hendricks of Challenger joins Closing Time to share what he is hearing in the industry as the major SKO themes for 2024 – and the 2023 hangovers we’re still dealing with.

You’ll learn how to future-proof your sales approach beyond SKO by establishing a culture of sales training in your org and see the unique way Geoff gets sales leaders to divulge their secrets on his podcast, My Best Sales Mistake

Watch the video:
Key Moments:
SKO Themes of 2024: Changes to the B2B Buyer Journey

Imagine stepping into an arena filled with energy, ambition, and the collective buzz of sales professionals gearing up to conquer the year ahead. That’s the essence of a Sales Kick-Off (SKO), an electrifying annual event where companies rally their sales troops, aligning them on goals, strategies, and the game plan for achieving sales excellence.

It’s more than just a meeting; it’s a launchpad for motivation, collaboration, and training, designed to ensure every team member is ready and inspired to hit their targets.

Geoff dived into the heart of 2024’s SKO themes, sharing a wealth of insights from both his experience and conversations with sales leaders. The central theme remains pipeline generation—a cornerstone of sales success. Yet, Geoff illuminated a pivotal shift towards not just building, but also rigorously validating sales pipelines. This change arises from a challenge many teams faced: a shaky confidence in their pipelines that severely affected forecast accuracy, leading to stalled deals and fluctuating win rates.

This issue is, in part, a lingering effect from 2023, with sales teams witnessing a drop in win rates due to struggles in accurately predicting the closure of mid to late-stage deals. Addressing these forecasting challenges is crucial for refining sales strategies and ensuring a more dependable sales process.

Moreover, Geoff emphasized the increasingly complex buying environment. Tight budgets and increased scrutiny have made purchasing a daunting task, adding layers of complexity to buyers’ roles. This has not only stressed buyers but also highlighted the importance of empathy and support from sellers’ ends. Recognizing and easing these pressures can pave the way for smoother transactions and stronger relationships.

To navigate these waters, Geoff advocates for sellers to hone skills and strategies that lighten buyers’ loads, focusing on engaging the right prospects and simplifying their decision-making journey. As the sales landscape evolves, embracing these themes will be vital for triumph in 2024 and beyond, marking a year of strategic insights, empathetic selling, and renewed vigor at the heart of every Sales Kick-Off.

No Seller is Perfect: Learning From Top-Performer's Mistakes

Geoff brings a unique perspective to the world of sales, focusing on the power of learning from mistakes. With a background in consulting and stepping into sales for the first time, he noticed a trend on platforms like LinkedIn where seasoned professionals share advice, seemingly having their careers all figured out. However, Geoff highlights that these individuals have years of experience behind them, which is why they seem so adept.

He introduces the concept of prospect theory, particularly loss aversion, to explain how mistakes often leave a more lasting impression than successes. This psychological principle suggests that the pain of losing is psychologically more impactful than the joy of gaining.

Geoff applies this to sales, suggesting that recalling our errors can be more memorable and influential in shaping our future actions.

This approach underpins his method of engaging with sales leaders and professionals, encouraging them to share their career missteps. By doing so, Geoff believes that not only can these stories serve as cautionary tales but also as rich learning opportunities for others, especially those newer to their sales journey.

He emphasizes that understanding the backstory to advice can reveal the imperfections and growth paths of those we look up to, making the journey feel more accessible and human.

The Genesis and Impact of the Challenger Model

Amidst financial constraints brought on by a mortgage and banking crisis in 2008, Geoff’s former company, CEB, noticed a curious trend: a small group of sellers wasn’t just meeting their sales targets; they were smashing them, while others lagged behind at 40% of their goals. This sparked curiosity and led to an investigation into what these high performers were doing differently.

This exploration unearthed two pivotal insights. First, from the buyer’s perspective, the essentials like company brand, product quality, and price were just the starting point. What truly set sellers apart was the sales experience—offering fresh perspectives, insightful guidance, and rallying the buyer’s team towards a decision.

On the flip side, examining the sellers revealed five distinct profiles, with two—’the lone wolf’ and ‘the challenger’—standing out for their exceptional performance. The ‘challenger’, in particular, matched the buyer’s desire for a transformative sales experience.

The essence of the Challenger model is not about a complete overhaul but adopting key strategies from these successful profiles. It’s about making incremental changes to improve sales outcomes, benefiting not just the sellers but their families and companies. This concept has gained significant traction, leading to articles in the Harvard Business Review, bestselling books, and a decade-long journey of helping organizations embrace these effective sales behaviors.

Geoff highlights that the Challenger approach begins with a mindset shift towards prioritizing the customer’s business needs over one’s product or solution. This mindset can be applied throughout the sales process, from initial outreach to closing deals, always with the aim of making the buyer’s journey smoother and addressing their concerns.

One of the core principles of the Challenger methodology is helping buyers navigate potential risks, a topic of much interest in sales discussions. By leveraging their in-depth industry knowledge, sellers can guide buyers away from common pitfalls, thereby earning trust and facilitating a successful sale. This approach not only addresses buyers’ fears of making a poor decision but also positions the seller as a trusted advisor, fundamentally changing the sales dynamic for the better.

Empowering Sales Teams: Cultivating a Culture of Continuous Learning

The journey toward excellence in sales is continuous, with each day presenting a new chapter of learning and growth. This isn’t about the occasional training session or annual seminar anymore. The most forward-thinking companies understand that to stay ahead, learning must be an integral part of their daily operations, not just an item on their annual agenda.

Geoff points out a significant challenge in training: the forgetting curve. This concept reveals that without reinforcement, people can lose up to 87% of what they’ve learned within just 30 days. This statistic underscores the importance of continuous learning and reinforcement to prevent knowledge loss.

To combat this and encourage ongoing learning, Geoff suggests a comprehensive approach focused on organizational capability. He breaks it down into four essential elements:

Message: It’s vital to communicate the value of what’s being offered in a way that resonates with the customer, going beyond just features and benefits.

Managers: Managers play a crucial role in coaching and reinforcing learning. Their early and frequent involvement is key to sustaining momentum.

Skills and Behaviors: Training should cover both the mindset and tactical skills sellers need to succeed.

Alignment with Sales Processes: Tools and processes, such as CRM systems, should support the learning objectives, making it easier for sales teams to apply what they’ve learned naturally.

Geoff’s advice to sales leaders is to prioritize learning as a core aspect of their team’s development. By focusing on these four elements, organizations can create a supportive environment that not only facilitates change but also ensures it sticks, leading to better performance and growth.


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.
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?
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.
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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We will see you next week.

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