According to a 2024 report from Salesforce, more than half of sellers say it’s harder to sell now than it was a year ago. In the face of constantly changing headwinds — not to mention dynamic technology, rising expectations, and unrealistic quotas — sometimes all a seller needs is a little advice.

That’s why we invited retired global sales leader and longtime Challenger champion Charles Forsgard to join us for a special “ask me anything” episode of Winning The Challenger Sale. As a leader at companies like Honeywell, GE, and Schneider Electric, Charles Forsgard saw it all. So, he came well-prepared to answer viewer-submitted questions running the gamut from using data to protect your team to preparing yourself for the next level of leadership. A few of his most thought-provoking answers (condensed and edited for length) are below. Check out the on-demand episode, “A Fireside Chat with a Fortune 500 Sales Leader,” for the full interview.

Q: Are great salespeople born or developed?

“If you don’t have some core things in your personality in terms of how you’re wired, no amount of training will turn you into a great salesperson.

If you’ve got those core things then training, and coaching, all those things can make you an incredibly good salesperson, and you can get progressively better and better and better. But there is a reality that there are a lot of people in this profession who, I think, are beating their head against a brick wall because they’re handicapped by the attributes they’re missing.

And so, they must artificially try to do it. And I think you can force your way to succeeding. But I think the problem that you get into if you take that approach is there’s probably something you really are wired to do that, A., you’d be a lot better at, and, B., you’d be a lot happier doing…

… [In those cases, it’s up to managers] to guide them into something else. That doesn’t mean you have to fire them. They might be a great asset for your company. They’re just in the wrong job.”

Q: How do you balance upper management’s interest in deal development without putting too much pressure on your team or overpromising results?

“As a sales leader, it’s your job to do two things.

I used to work with this fantastic CMO, and she called this ‘feeding the beast.’ So, as a sales leader, you serve two audiences. Right? You had to feed that beast up top and give them what they need. And then you had to send the right message to your folks. You had to send the message that leadership wants going out to the salespeople.

But you could always, you know, insulate them from a lot of the constant “boom, boom, boom, boom, boom,” so that they can stay focused on what they need to be focused on. And that’s really the key thing I think you have to do with leaders. ‘Am I getting the right information about the folks up there so they can do their job? And am I allowing the folks down below me to focus on the right things and guiding them to focus on the right things?’

It’s a question of balance of, you know, what I do up there and what I do down here, and how I make sure everybody’s staying focused on the things that that they should be focused on.”

Q: What’s the key to getting senior leadership to use analytics and show their value to the entire organization?

“I think the answer to that question is: if you expect someone else to do something, you better be doing it yourself. So, if you want other people to use analytics, you should be using them and proving through your use of them that it’s a valuable approach.

I’m a big proponent of customer relationship management software [CRM]…because if you’re using it correctly, as a salesperson, it can drive effectiveness through the roof.

And the analytics you get from it help you in so many ways because they tell you what to focus on. So as a sales leader, you should be using those analytics to help enable your salespeople to focus and predict ‘This is what I think is going to happen by the end of the month, the end of the quarter, etcetera.’

If you’re doing that just inherently in how you run your business, and not just doing it for show, and you make it part of your personal operating system, whoever’s above you, whoever’s above them, whoever’s above them, is going to notice. They’re going to say, ‘Wow. That team knows what they’re doing.’

I can sit there and tell senior leadership all day long, oh, you should believe my number, or you guys should really use analytics. Well, I only do that when I’m using them [myself], and the results show.”

Q: In your experience, how is Challenger different from other sales training programs?

“The beauty of Challenger to me is that I know it works because I know it’s based on data. I know it’s based on what has worked best. You can look at anything that the Challenger methodology asks a salesperson to do, and you can point back to the data that said “this is why that’s so.”

If I’m trying to convince a salesperson to enhance the way they’re going out and selling, I’m asking you to change, and change is hard. And I want you to make that investment in yourself to not just sit through the class but go do something different next Monday.

I’m not asking you to do something different because I think it’s a good idea. I’m asking you to do something different because the data says if you do it, you will get a better result.”

Q: How did you introduce the Challenger Sale in the companies you worked in as a sales leader?

We started with an introduction where we worked with Ramsey Jay Jr., who’s just incredible in front of the room. We started off with “The JOLT Effect,” with Ramsey doing a ninety-minute kickoff. Then we did the full-blown sales kickoff that was based entirely around the [in-person] training.

But what made that piece of it that much more powerful, because we were doing it at a sales kickoff, was having a bunch of early adopters who we pulled on the stage to talk about what it meant to them. The great thing about these early adopters was that although they were very successful salespeople already, they were [initially] very skeptical of needing to do anything different. And rightfully so – they’re already successful without doing it.

People are going to listen to another salesperson more than they’re probably going to listen to me about this stuff. But the best part was this one salesperson telling this great story of how he won this deal, and he kind of was stuck on how he’s going to move the deal forward. And he said, well, I’m going to give it a try. And this is a guy who said ‘I don’t like tension.’
But, he realized he had to create that tension. And when he did, boom, the deal came through.

So I think if what you do is reinforce it with data, cases of people that went and did it and it worked for them (not just the statistics in the book or the background from it, but people in your own organization who are succeeding with it and how it’s changing things), that will then build on itself as you go to launch it.

Q: What advice do you give to mid-career sellers interested in transitioning from individual performance to effective sales leadership?

“This will sound trite, but I mean it: be a leader without the title. In a sense, your peers are the ones who are going to promote you. If you’re someone that your peers lean on and go to for advice all the time and you’re always, you’re that coach of your peers, that’s going to get noticed by the people above.

And the reason I say that’s so important is that I can tell you, except for the first time I stepped up, every other promotion, every other step-up job I got in my career, I was tapped on the shoulder. And it’s because I was demonstrating what they wanted to see in what I was doing with my current job.

So, do a great job in your current job if you want to get that next job. But part of that is creating a situation where you’re showing those leadership skills they want to see, and leading when you don’t have the title is the hardest form of leadership.

So if you do that, you will get noticed, and it will happen. Now, I’m not saying you don’t have to, you know, still do the things that will drive you forward, but it starts with you don’t have to have the job to be a leader.”

More sales Insights from a Fortune 500 leader

Wish you could hear more insights from Charles? Tune into the full episode of Winning The Challenger Sale to hear more from Charles on dealing with upper management, implementing Challenger, accelerating your sales career, leveraging data, and more.

You’ve heard the old joke about how you get to Carnegie Hall. Strangely, the same directions apply to success in selling: Practice, practice, practice.

No matter how enthusiastic the seller response from a workshop or kickoff, they won’t truly adopt the skills and behaviors that lead to higher performance without reinforcement. And to build a culture that supports skill adoption, you need to not just teach skills but foster an approach that shows your team the benefits of change.

Challengers recognize this as a three-part framework we call the Skill, the Will, and the Hill:

• The Skill Pinpoint the Challenger skills that sellers need most
• The Will Alleviate resistance and drive sellers to take action in modifying their behavior
• The Hill Create an environment that allows for experimentation and learning

For MSC Industrial Supply, a Challenger client, the Hill turned out to be the key that unlocked the Skill and the Will among its sellers.

MSC supports its customers in the manufacturing industry by helping them lower costs, drive productivity, and eliminate waste in their manufacturing operations (MRO).

For years MSC sellers relied on relationships, offering fast delivery of its millions of products. But MSC’s leadership realized that, to stay competitive, they needed to shift their approach from selling parts shipped “just in time” to proactively providing Insights and other items of value.

As they adopted Challenger, they faced skepticism from a deeply tenured salesforce, numbering in the thousands, who weren’t too sure about changing how they approached sales — in some cases, for decades.

By building Challenger into the sales process, including coaching conversations, MSC signaled to its salesforce that these skills were central to their success. They also landed on an important realization: in using Challenger, MSC’s sellers delivered a better experience to their customers.

MSC uses a customer model known as MRO Go as a framework for continuous improvement. This aligned well to Challenger’s approach to account growth, which shows that accounts grow not from stellar service but from providing unique perspectives designed to grow business throughout the lifetime of an account.

As they saw this resonate with customers, sales and enablement leaders at MSC asked themselves: how do we create this same kind of continuous improvement model within our sales team?

And so, the Sales Mastery Program was born.

Externally, MSC’s sellers use the same framework to guide customers to continuous improvement, but often customize their solutions (because no two customers are alike!).

Changing seller behavior requires a similar approach. So as they rolled Challenger out across their teams, they customized development plans for each seller, aligned to four different levels.

As MSC’s sellers and sales managers move through the Sales Mastery Program, they complete capstone activities and assessments to move onto the next level — requiring sellers to reinforce the skills they learn in workshops beyond on-the-job activities.

This approach also opened benefits to managers and coaches. To successfully reinforce Challenger, managers need to understand not just what to coach, but how to coach. By adopting the Sales Mastery Program, MSC’s coaches were able to better understand Challenger concepts themselves, track seller skills development, and zero in on the skills their sellers needed to focus on developing. They also measured their own ability to coach and pinpointed areas of improvement and development for themselves.

Through the development of this program, MSC’s focus resulted in sustained skills adoption across their three selling divisions: Business Development, National Accounts, and Field Sales. It aligned their leadership and improved capacity for sales managers.

Which all sounds great … but what really matters is results.

Over the course of the first two years into the Sales Mastery Program, MSC reported:

• Improved speed and efficiency in its sales cycle
• Increased pipeline velocity
• Increase in sellers contributing to overall growth
• And a significant boost in win rates

And all of this — the very results that sales leaders dream of achieving — comes from their commitment to strengthening coaching and building a program designed to reinforce the unique selling skills and behaviors that set Challengers apart.

Though sales trends may change, sales leaders’ goals remain fundamentally similar: grow pipeline, close deals, increase revenue. Perhaps that’s why sales methodology training remains important to so many organizations, even as the buying-selling landscape continues to change. According to Gong’s 2024 State of Revenue Leadership report, 79% of the highest-paid revenue leaders rolled out a new sales methodology in the previous year. Though we haven’t tracked those leaders down (yet), we can anticipate one challenge based on our long years of experience: reluctant sellers who refuse, for one reason or another, to embrace a new way of selling.

Rolling out a new methodology and ensuring adoption represent two completely different issues, but to meet their goals, sales leaders must bridge the gap. That means getting those recalcitrant sellers on board by overcoming their objections and making it easier for them to embrace change and learn.

Five Challenger Selling Profiles

To get sellers on board, you must know where they are now and where you want them to go. When you imagine a reluctant seller, a very specific personality type likely springs to mind. But what makes a successful seller – and what behaviors do they exhibit?

The original Challenger research, published in “The Challenger Sale,” began with a study from CEB (now Gartner) that revealed the sales experience as the biggest driver of customer loyalty. This unexpected finding led authors Matt Dixon and Brent Adamson to ask what makes a good seller. After asking thousands of sales managers to identify the top 20% of their sales force as measured by performance against goal, they used the results to sort reps into five profiles. Core performers came from every category, but star performers came from one dominant category: the Challenger.
Of all the high performers in the study, nearly 40% were Challengers. Meanwhile, Relationship Builders generated the fewest star performers.

The Problem Solver (14%)

This seller lives to solve customer problems, even after the deal closes. This is more important to them than finding new business, to the detriment of their own performance. The smallest number of reps, about 14%, fall into this category.

The Lone Wolf (18%)

This seller is self-assured and confident in their instincts. Sales managers know them well because they rarely update their CRM, typically skip trainings, and generally resist any guidance or coaching. They hit their quota, and in return, managers tolerate their behavior. About 18% of sellers fall into this category.

The Hard Worker (21%)

This seller always goes the extra mile. They’re the first to come into the office and the last to leave. The Hard Worker doesn’t give up easily, is self-motivated, and seeks out feedback for personal development. It’s easy to love Hard Workers — and that’s one reason their performance in complex sales is so disappointing. About one-fifth (21%) of sellers fall into this category.

The Relationship Builder (21%)

Customers ask for this seller by name. They build strong advocates in their customer’s organizations, give generously of their time, and get along well with everyone. Another 21% of sellers fall into this category.

The Challenger (27%)

Challengers stand out because they see the world differently. They understand their customer’s business and build growth opportunities around specific commercial insights. The Challenger relishes debate and isn’t afraid to push customers. 27% of sellers fall into this category.

Those results beg the question: are sellers stuck with their natural profile type?

Absolutely not. No matter where sellers fall, they CAN learn to augment their natural selling style with Challenger skills. But they must be willing to learn. If sellers are reluctant to change, they’re either missing the skill, lacking the will, or unwilling to summit the hill (meaning they haven’t bought into the concept yet).

Hear more of this concept from Alex Panou on our most recent Winning The Challenger Sale webinar, “How to Train the (Seemingly) Untrainable).”

Now, let’s dive into three types of reluctant sellers and how to get them on board.

Non-Sellers

This group of potential sellers hail from a host of different backgrounds and emphatically do not “do sales.” Perhaps they absorbed business development duties from a colleague and don’t know how to sell (i.e., they lack the skill). We also see this type of objections from those that transition into sales from different roles. Think of the engineer or analyst whose manager says “you’d be great at sales,” before they roll their eyes. This person lacks the will to sell. Or, maybe this type of potential seller simply isn’t bought into the value of challenging customers; consider the client success manager who focuses on customer satisfaction and fears that challenging customers during an upsell process may sacrifice the relationships they see as paramount.

For this group, we can aid adoption by overcoming objections. Use these approaches:

1. Challenger isn’t just for sales. Challenger, at its heart, means disrupting a customer’s status quo. There are applications beyond sales, including marketing, customer service, or even personal interactions.
2. Customers want to be challenged. Over a decade of research into B2B buying behavior shows that Buyers value sellers who introduce new ideas or approaches to solving business problems far more than they value friendly relationships.
3. Share examples. Engineers like evidence; show them examples of people like them succeeding.
4. Create a safe environment to practice. No one likes to get it wrong — so give them opportunities to fail and learn without risking any business.

The Unwilling

This second group of sellers may voice fears about not having the right to challenge customers, whether out of concern that it will change the dynamics of a longstanding relationship, a lack of confidence in their own materials or research, or something else. This group also includes those who are deeply devoted to their own selling styles and skeptical of the need to adopt something new.

For these sellers, embracing change means overcoming fear. There’s the fear of failing, letting clients down, or changing, perhaps late in a successful career. For these sellers, the pain of staying the same must be greater than the pain of change. It may take more time to convince them that challenging helps.

1. Everyone makes mistakes. Even experienced sellers and highly-successful clients don’t get it right 100% of the time. It’s okay if you don’t either, as long as you keep trying.
2. Buying and selling have changed. Buying has become more complex, with stakeholders, sales cycles, and other factors growing in complexity. If a Lone Wolf wants to be successful, they must change too — what they’ve always done won’t work anymore.
3. Be part of the Insight engine. Explain the importance of Reframing customers and helping them understand why they need to change. That type of exposure will get them even more comfortable not just with challenging, but understanding why change matters.

It may also help to give this group a simple way to test out the Challenger approach. The framework we refer to as “A Gap B” offers a simple, accessible formula to help customers move from their current state to a new way of doing business– essentially, challenging their thinking with an undiscovered problem.

Sellers with cultural concerns

Finally, some sellers may block adoption out of a conviction that Challenger methodology is a bad fit for their culture — or their clients. They worry they’ll upset clients by being too assertive, that relationships are too important for them to openly question customers, or that Challenger selling only works in America.

To help increase adoption among this group, try this approach:

1. Emphasize that Challenger works in every region. As Veronica Coli addressed in “Beyond Borders: Myths About Challenger in International Markets,” Challenger can be adapted to work in any region. In fact, of the organizations who partnered with us to implement Challenger methodology in their sales organizations, over 40% come from outside of the US.
2. The strongest relationships share trust. Building that trust sometimes means honestly delivering bad news or engaging in a debate.
3. Pay close attention to the dial of Constructive Tension. You need some tension to move any conversation forward. Make sure your use of Constructive Tension doesn’t go too far, particularly in certain cultures.
4. Reiterate why you challenge clients. Our research shows time and again that buyers want sellers who can be trusted advisors who help them think about their business problems in a new way, identify and minimize risk, and improve their business.

Challengers aren’t born — they’re made

Your sellers are smart and capable. And if they’re like most people, they don’t love change — which includes adopting a new methodology, especially if it feels unlike them. But Challenger isn’t a fad – it’s built on research that shows the sales experience is the biggest driver of customer loyalty. More than that, it relies on the demonstrated success of a particular type of seller. Sellers may have an inherent selling style, but their future isn’t set in stone if they’re willing to adapt and learn.

To get the most reluctant sellers over the hump, sales leaders must bust the myth that “the customer is always right.” Further, they must adopt a Challenger mindset themselves: driving growth among individual sellers – no matter their age or background – is possible if their coaches and managers are willing to make them uncomfortable. In short, there’s no such thing as an “untrainable” seller – just reluctant people in need of a mindset shift.

Any sales leader deserving of that title knows that they need a sales methodology.

Sometimes, they build the SKO around it. Maybe they roll it out mid-year. Either way, they follow a typical path: they outline what they need in terms of process and common language, book the workshop and thrill to the excitement they see reflected in their GTM teams and sales reps.

All that time and effort from the sales leadership and the enablement team builds enthusiasm and interest, and yet… when we asked sales leaders about how reinforcement fits into their training programs, over two-thirds said they don’t follow up with formal programs.

What these leaders don’t realize is that without reinforcement and coaching, even the most enthusiastic sellers struggle to adopt a methodology and engage in true behavioral change that impacts their ability to win and grow.

It’s an area where many companies falter and one where the stakes are high: According to Ebbinghaus’s “Forgetting Curve” theory, organizations that don’t provide reinforcement risk sellers losing around 87% of that new knowledge within just 30 days.

The good news is that we’ve seen coaching and reinforcement programs add incredible value to Challenger training investments. As our client Connection demonstrated during the webinar session “Scaling a Culture of Coaching and Reinforcement,” you can embed reinforcement into training right in your corporate DNA — and this starts before you even roll out a new sales methodology.

Launching with buy-in from leadership

As Dennis Riseman, VP of sales at Connection, shared on our recent webinar, embedding a methodology into your sales culture requires visible leadership buy-in from the get-go.

“We wanted to make sure that we didn’t treat this as a training event,” Dennis said. “We really didn’t want was for our sellers to come to this event, get trained, walk out saying ‘This is great!’ and then go back to doing what they’ve always done.”

Instead, they kicked off training with a simple, powerful story from a member of the executive team.

“He talked about how one of our top sales reps had a conversation with one of his most dedicated customers,” Dennis explained. “They’ve been working with us for 20 years. And the customer said, ‘Hey, one of your competitors called me up and offered me a really strong insight about our business. It was something I wasn’t even thinking about. So I gave him the business because he earned it.’”

That loss pushed the executive to seek out Challenger because he needed an Insight-led methodology. Sharing that experience helped Connection’s sellers understand what was at stake.

Plan a cross-functional rollout

Start planning your rollout by considering which sales functions need training the most. While it’s tempting to focus on high performers (who are easier to work with) or low performers (who might want or need the most assistance), many organizations find the biggest impact from coaching core performers.

Challenger calls this concept moving the middle because core performers make up the largest proportion of most sales teams and represent the most potential impact for your training investment. Positive results from this group can create more organic internal interest in training.

As Dennis shared, “One of our strong sales reps sat in an early session and realized: ‘Hey, I’m what’s known as a Relationship Builder!’ He had this realization that he really struggled with Constructive Tension. So he committed to it. His manager committed to coaching him, and he did a lot of work with his peers to improve in this area.”

Eventually, that seller moved up to the highest level of sellers at Connection — and shared that his training and, crucially, follow-up with his manager helped him feel confident bringing Insight to his clients.

A true cross-functional rollout also needs to include frontline and mid-level managers, as well as technology and marketing specialists. With training under their belts, this team can offer support to sellers as they get used to a new methodology and ensure that it’s embedded throughout the organization and customer interactions.

Leverage peer consulting groups

After drumming up enthusiasm and launching a sales training program, sellers need a comfortable place to practice their new skills. At the request of team members, Connection added peer consulting groups to its Challenger selling curriculum.

These small, cross-functional groups came from across the company and included generalists and specialists who could review what they were learning and solve problems together. This format removed an element of pressure that may have kept sellers from raising questions with superiors or sales leaders during their training sessions.

“We saw our win rates go up, we saw more engagement from our people when it came to Challenger, and even outside of Challenger…that collaboration went up another level altogether,” Dennis said.

Hear more about Connection’s approach to peer consulting in this short clip from our webinar.

Maximize your training investment with reinforcement

Organizations looking to maximize their investments in a new training methodology can’t afford to overlook the importance of reinforcement. By pausing to gain (and broadcast) executive buy-in, creating a cross-functional rollout plan, and embedding reinforcement in your LMS, organizations can ensure that their investment in a methodology isn’t just a one-off initiative but the beginning of a true cultural change.

This is just the beginning! To see the complete six-step plan Connection used to gain 13:1 ROI on their Challenger training investment, watch the on-demand replay of our Winning The Challenger Sale webinar, “Scaling a Culture of Coaching and Reinforcement.”

Since we began tracking B2B buying behavior more than ten years ago, the market, technology, and buying cycles all ballooned in complexity. Yes, your dad is right: everything used to be a lot less complicated. Anecdotally, we hear that sellers face significantly increased pressure to perform even as sales cycles elongate and new procurement processes take hold. Our ongoing research into customer behavior illuminated this in detail.

We also noticed that a painstaking customer buying process and a more difficult economic environment increasingly resulted in what we call “purchasing gridlock.” One major problem — the growing size of the B2B buying group — helps explain why your once-healthy pipeline highway now looks like a parking lot. Your sellers need to understand what customers want, and why sharpening their skills can clear the congestion.

Tracking growth in the average B2B buying group

In 2019, Challenger surveyed a large sample of B2B buyers and asked them to reflect on recent large purchases that included an interaction with a seller. The study aimed to see what, if anything, changed regarding buying behavior and drivers of loyalty since the original research.

While the research uncovered that many of the drivers of loyalty remained the same, it also revealed major developments in the size of buying groups. Specifically, the typical B2B buying group roughly doubled. When we track changes over time, we see it increase incrementally every few years from 5.4 in 2009 to 6.8 to 10.2 to just under a dozen in 2019.

Challenger also found in 2019 that up to 38% of customer purchase attempts end in “no decision.” In other words, nearly 4 out of 10 would-be buyers in the study started a purchase process only to quit before deciding to change anything. In “The JOLT Effect,” authors Matt Dixon and Ted McKenna found medium-high levels of indecision present in nearly 90% of complex deals and that no decision loss accounts for 40-60% of all lost deals.

Together, this makes for an alarming development for sellers.

How economic realities contribute to B2B buying gridlock

The global economy slowly but steadily improved after the 2008 global financial crisis, which meant booming headcounts and investments. Then, in the early days of 2020, we saw major investments in technology as companies accelerated their digital transformations and accommodated remote work.

As companies looked to stabilize through the will-it-recede-or-won’t-it pandemic years of 2020-2024, they implemented stronger controls through functions such as procurement. Many buyers saw their budgets tightened or eliminated altogether. Then, as teams redistributed resources to meet demands, the question of “who owns what” led to an even squishier sales process.

Now, the typical B2B purchase process might involve a dozen people from several different departments and time zones. Selling a solution touching stakeholders across expanding go-to-market teams, for example, might involve gaining buy-in from VPs in three departments, individual stakeholders from operations to sales to marketing, and a chief revenue officer – as well as legal, procurement, and implementation teams.

Our virtual reality

Our research shows that buyer behavior and how sellers respond changed significantly after the pandemic. All that investment in emerging technology transformed our working conditions, making it easier than ever to invite new stakeholders to the (virtual) table. And while aligning calendars might seem easier with Outlook and GoogleCal, this pattern presents its own challenges for buyers and sellers when it comes to wrangling consensus from the buying group.

Customers may face the expectation of including more internal “experts” in every sale, which means building more consensus. Unless managers and sellers are trained to handle these large, complex, multi-stakeholder deals, they may be unprepared to push the deal forward. Remote work also complicates the landscape; when sellers can’t walk into an office, it can feel impossible to identify the real size and shape of the B2B buying group. The net effect is a shift toward many-to-many sales where sellers must coordinate many internal stakeholders to address the needs of many customers.

How gridlock contributes to no-decision losses

Challenger sellers know that identifying buyer types is a key part of an effective B2B sale. But in this environment, sellers struggle to tell Talkers and Mobilizers apart. They may also fail to address the concerns of Blockers effectively. With so much of the purchase process taking place behind closed doors, sellers can find themselves listening with “happy ears” and projecting a sale to close – only to find that it stalls in the final mile because someone in the buying group developed cold feet.

With so many voices and needs at play, gaining consensus is harder than ever before. In “The JOLT Effect,” Dixon and McKenna defined three roots of indecision. Buyers struggle to agree with each other, and in fact, each may bring a different concern (or a mix of them) to the deal – resulting in multiplying, compounding, ongoing indecision.

• Choice overload happens when prospects fail to prioritize their needs – or the needs of competing stakeholders. As buying groups multiply, those needs may compete so intensely that they simply cancel each other out, leading to a no-decision loss.
• Information overload occurs when sellers blindly send resources to their buyers instead of curating them to address their specific concerns. For sellers, the key moment lies in recognizing the tipping point between helpful answers and information overload. With large, opaque buying groups, this may be particularly difficult.
• Expectations overload stems from a lack of trust, either in the outcomes the seller presents as possible or in their company’s ability to achieve them. If internal politics, difficult procurement processes, or past failed implementations are on their minds, members of a B2B buying group may balk.

In reality, the signs of looming indecision often present themselves in a sale cycle from the very first call. To effectively overcome indecision, sellers must recognize and respond to those cues throughout the sales process, and that comes down to building seller skills.

Developing seller skills solves gridlocked buying

It’s up to sales leaders to educate their sellers with the tools and skills they need to successfully engage and close deals with large buying groups. Again, we can turn to our 2019 buyer survey, which reveals that the increasing size of B2B buying groups isn’t just a headache for sellers, but for customers, too. Customers need support to help them navigate these challenges, and the wisest sales organizations are equipping sellers and their managers with new skills aimed at this new sales challenge.

While some sellers may struggle to wrangle a large buying group, truly skilled sellers approach the purchase process with a commercial insight specifically designed to position them as trusted advisors. They come armed with the experience and skills necessary to guide buyers through the purchase process – including helping them make decisions using an updated playbook, addressing different stakeholders’ needs, and building support across the organization. Building and enforcing these skills in frontline sellers and sales leaders enables organizations to clear the congestion in their pipelines and avoid new gridlock before it begins.

Sales forecast accuracy is something everyone wants, and, it seems, no one can truly get.

Forrester rated the forecast accuracy of organizations whose sales projections fell within a 5% margin of error as excellent and those who performed within 10% as good.

But that level of accurate sales predictions proves elusive for most sales leaders. In its 2024 Sales Forecasting Benchmark Report, Xactly found that just 20% of sales organizations achieved forecasts within 5% of projections. 43% reported sales forecasts that missed goal by 10% or more.

Additionally, fewer than 43% of sellers reported achieving quota attainment in Q2 2024, according to RepVue’s Cloud Sales Index — a decrease of 8% over the last two years. While RepVue’s data only covers SaaS companies, their research aligns to something we’ve heard repeatedly from clients across industries and verticals: sales and customer success leaders struggle deeply with sales forecasting. In a poll Challenger conducted in January 2024, less than 20% of sales leaders rated their sales forecast accuracy as “predictable.”

This lack of predictable sales projections is more than just spreadsheet jockeying. Inaccurate sales forecasts result in missed sales goals, which lead to missed revenue, snowballing into layoffs or budget cuts, resulting in less investment in current customers and less customer acquisition.

That inaccurate sales forecast snowball expands into an avalanche that no sales leader can afford to find themselves in, ultimately driving lost confidence from leadership and, even worse, lost customers and lost acquisition.

But sales forecast accuracy is as much science as art — and to improve sales forecast accuracy, sales leaders need to understand common mistakes in sales forecasting and follow Challenger’s best practices for accurate sales forecasting.

What is forecast accuracy?

Let’s start by defining sales forecasts and sales forecast accuracy, which measures how close a sales organization comes to predicting its sales performance in both the long and short term.

Creating an accurate sales forecast can include:

• The amount of sales pipeline your organization expects
• How much of that pipeline converts to opportunity
• The size of a potential deal and the timeline in which your sellers expect to close those deals
• Total closed-won business and expected sales revenue

What are the most common mistakes in sales forecasting?

Teams struggle to improve forecast accuracy for a host of reasons, old and new.

First, sellers face rising levels of customer indecision. Research into more than 2.5 million sales calls, conducted in 2020 and published in “The JOLT Effect,” found that 90% of those calls contained markers of customer indecision. What do we mean by indecision? While it often shows up as the dreaded cold feet at the end of a deal cycle, customer indecision in fact rears its head early in a sale, often in ways that lengthen cycles and make it harder to forecast a close. In fact, win rates are negatively correlated to levels of indecision.

Second, buying groups skyrocketed in the past few years, bringing infighting and conflicting approaches to buying along with them. Our research showed that the average number of stakeholders in a B2B buying team grew to an average of between six and 11, with more complex sales involving more stakeholders. A 2023 study from 6Sense found an average of nine members on B2B buying teams.

Next, there’s buyer behavior. Sellers fight over the scraps of an increasingly narrowing slice of customer mindshare. According to Gartner research, buyers only spend 17% of their buying time meeting with vendors. That’s all vendors, including a company’s competitors — and they like it that way. Seventy-five percent of buyers told Gartner that they wanted a completely rep-free experience.

How do you recognize the signs of inaccurate sales projections?

There are a few specific, evergreen challenges that sales leaders need to recognize and understand will negatively impact sales projections, resulting in inaccurate sales forecasts:

• Inaccurate data in the CRM
• Assuming a verbal “yes” means a signed contract and closed-won business
• An inconsistent sales process
• Sales managers who take differing approaches to sales forecasting
• The dreaded happy ears
• Unpredictable macroeconomic issues

Yet these common mistakes in sales forecasting are more symptoms than the underlying issue. And sales leaders who want to move themselves toward improved sales forecasting need to address the root causes — and they need to address them in the right way.

Sales forecast pitfalls to avoid

When sales leaders face a problem as widespread, and with as terrifying consquences, as inaccurate sales projections, they often pursue tactical, short-term fixes.

But just as American poet Taylor Swift once noted, “Band-aids don’t fix bullet holes,” short-term fixes that fail to address the root causes of inaccurate sales forecasts won’t stop the ongoing challenges that sales leaders face.

Mistake no. 1: Draining leadership time on seller activities

When sales forecasts vary widely from expectation, sales leaders will focus on results at a deal level, implement a complicated qualification framework like MEDDPICC or BANT, or perhaps add more fields to the CRM — and then spend their time following up to discover sellers never filled out that unnecessary data or used that new qualification framework. All of that time-consuming work should sit with sellers, and it brings sales leaders nowhere near producing more accurate sales forecasts.

Mistake no. 2: Overindexing on discounting

Cutting pricing will erode profit margins and devalue products. Ultimately, those discounts likely just save a deal that never should have been included in a sales forecast. They can also challenge retention and negatively impact the customer experience.

Mistake no. 3: Adding too much cushion to sales projections

No one likes to have their time wasted or feel misled. When sales leaders add too much cushion to sales projections, they open themselves up to outsized scrutiny from their board or senior leadership and set false expectations for their teams. This makes it more difficult for leadership to trust the data a sales leader brings to them. It demoralizes sellers and sales managers, too, who feel like they’re always chasing a number that truly does not exist.

To bring an organization to that magic number — less than 10% variance from a sales forecast — sales leaders must focus on addressing the underlying reasons that cause sales prediction mistakes.

That means turning focus earlier in the sales process, understanding the buyer types who help and hinder a sale, and using artificial intelligence to validate the data behind your sales forecasts.

Best practices that lead to accurate sales forecasting

Just as there’s no such thing as a 100% accurate sales forecast, there’s no single forecasting tool or one-step solution that can solve this issue.

Sales leaders instead need to enhance sales prediction accuracy by digging into how sellers and managers analyze their deals, including who they sell to, how they judge progress and track markers of indecision, and the tools they use to score it all.

Train sellers to identify Mobilizers

Challenger sellers learn to take a hard look at the members of their buying group and ask whether they’re Mobilizers or Talkers. This step is crucial for improving the accuracy of your forecasts, because while Mobilizers can move deals forward, Talkers are all mouth and no movement.

A Talker readily shares information but focuses only on themselves. You’ll know them by their use of “I” statements, willingness to answer every call and email, and tendency to go along with every suggestion. You might also recognize them when your deals start to fall apart because Talkers lack the internal capital to drive decisions forward.

Mobilizers, in contrast, exhibit healthy skepticism. They are far more thorough – which can mean more intense work upfront for sellers – because they know the value of building consensus in a buying group. While they might seem more difficult to deal with, this is exactly the behavior that lets us know that Mobilizers can be relied upon to drive decisions forward.

Sellers and managers motivated to improve forecast accuracy need to focus on what the buyer does, not what they say. Truly indicative factors – those that you can hang a forecast on with certainty – will show up as customer actions, not customer words. These actions can often be difficult to observe because they may take place behind the scenes. That’s where the Powerful Question comes in.

To achieve sales forecast accuracy, close the gap between what customers say and what they do

It’s impossible to predict whether a deal will close without sufficient information.

Often, when those difficult-to-observe behaviors are at play, sellers need to know more about what’s going on behind the scenes. To pull out those answers and accurately predict when a deal will close, your sellers must learn to ask Powerful Questions.

This means going beyond the status quo questions to dig deeper, ask for more specificity, and even ensure customers (who may be new to a complex sales process) have considered all potential Blockers to a sale. This is the key to closing the gap between what customers say and what customers actually do, which addresses the root of inaccurate sales forecasting.

Powerful Questions for sellers that lead to stronger sales projections

• “Will [exec sponsor] approve this initiative?” becomes “Does [exec sponsor] have a clear understanding of the ROI of this investment?
• “Who else needs to be involved?” becomes “Typically our clients need CFO approval for a purchase of this size. Is your CFO aware of this investment?”
• “Can we commit to a signing date of XX in order to hit XX milestone?” becomes “In order to begin on time, we need to finalize the agreement by XX date. Are your procurement and legal contacts aware of that deadline, and are they committed to meeting it?”

For the same reasons, sales leaders should be asking powerful questions of their sellers. This level of accountability helps sellers get realistic about deal forecasting.

Powerful Questions for sales managers that lead to stronger sales projections

• “Do you have executive sign off?” becomes “Do all executive stakeholders know they are in an active buying process? How did they respond to this investment?”
• “Do you have the right stakeholders involved?” becomes “Who is weighing in on this buying decision? Who have you spoken to? Who is still in the background?”
• “Has the client committed to a signing date?” becomes “How well do you feel your contact understands the approval and purchasing process? What is your confidence level that they’ve aligned all key stakeholders around signature by the committed date?”

Help sellers spot and address customer indecision

Crucially, research from “The JOLT Effect” shows that top-performing reps can judge the level of indecision in a deal early enough to proactively address concerns, push out its forecasted close, or disqualify the opportunity altogether. Sellers skilled in this approach more deals with a high likelihood of closing on time into their pipelines. They don’t experience last-minute cold feet at the same rate because they spot and address customer indecision long before it can derail their deals. Imagine how an organization-wide understanding of customer indecision could affect future sales forecasts.

Understand how buyer verifiers influence sales projections

Buyer verifers are signals that buyers give that indicate whether they want to move forward in a deal cycle. This is why it is incredibly important that sellers accurate gauge what buyers plan to do — not simply report what they say. It is what a buyer does that moves them forward in the sales process. When sellers observe and accurately capture the signals that buyers give, this allows sales leaders to produce more accurate sales forecasting.

Tools for improving sales forecast precision

For accuracy and repeatability, sales leaders need a systemic approach to better forecasting. That means equipping managers to ask the right questions. They should know not just to inspect seller performance, but what to look for, using Powerful Questions to probe for an unvarnished view. They should know how to coach sellers to identify Mobilizers and limit the influence of Talkers and Blockers, and above all, how to use these signals to accurately forecast when their own sales will close — or to know when to walk away.

Because forecasting is a team sport, improved forecast accuracy requires organization-wide change. Sales leaders must analyze sales forecasting culture to ensure the entire team approaches it thoughtfully and not as fire drills. How often the organization produces sales forecasts should be intentional and widely-known; many sales organizations forecast on a weekly, monthly, or quarterly basis and in many cases, they produce sales projections across all three time periods. Forecast accuracy should be an objective up and down the org chart, from frontline sellers to the CRO.

Most organizations need to operationalize improving forecast accuracy in one, or a blend, of three ways.

1. Manually Small organizations on a tight budget might decide to bootstrap their forecast accuracy. In this case, organizations will spend more time training their reps to notice signals of indecision, vetting their contacts for signs they’re a Mobilizer, and drilling on Powerful Questions. They may choose to use “report cards” and other deal inspection processes to develop their forecasts. Even a manual approach can improve forecast accuracy when it’s delivered with rigor and dedication.
2. In a CRM Building deal inspection into your existing CRM streamlines the forecast accuracy process for sellers and removes an element of human error from your analysis. For instance, RevOps teams might tag buyer profiles such as Mobilizers, Talkers, and Blockers in Salesforce. Sellers can use additional buyer verifiers throughout the life of the deal, building a reliable and accurate timeline with less room for error, producing sales projections that are far more accurate
3. Using AI Conversational intelligence tools use artificial intelligence to observe, record, and flag buyer behavior without bias. Tools such as Gong ingest data from conversations over the life of a deal to verify progress against sales forecasts more accurately. They eliminate the human error and “happy ears” that sneak into any well-meaning deal inspection. At Challenger, we’ve seen markedly higher win rates over traditional deal inspection after implementing AI buyer verifiers in our own sales process, both in our CRM and using conversational intelligence.

To improve forecast accuracy, go back to the beginning

Improving forecast accuracy is not about when an organization forecasts, but how sales leaders forecast for their business:

• Sellers must understand who they’re selling to, the forces stacked against them, and how to ruthlessly prioritize the deals they need to close, then accurately report them so the forecast contains accurate sales projections.
• Managers must know how to ask the right questions and coach their sellers toward the right targets and coach sellers on how to uncover buyer verifiers.
• Organizations must commit to a standardized, repeatable process using manual or AI-equipped tools.

It isn’t glamorous, but the results for improved sales forecast accuracy are clear. Organizations that equip their sellers and managers with the skills to verify and vet deals reap the benefits of more accurate sales forecasts.

In today’s economic climate, sales leaders face a unique set of challenges, and the landscape continues to change rapidly. With market conditions constantly shifting, it can be difficult  for revenue teams to know what to prioritize to keep your organization thriving and your team on track. However, with the right tools and strategies, sales leaders can learn to use the uncertain economic times as an opportunity to take stock of their current processes and improving operations to increase output.

1. Engage Your Highest Sales Performers

 

Never is the Pareto Principle – that 80% of the incremental output comes from 20% of the team – more acute than in times of crisis. In previous downturns we’ve observed that the gap between top and core performance widened as sales become more difficult to achieve. To this end, engaging top performers can mean the difference between an organization floundering or succeeding in the face of major headwinds. Sales leaders must make their best sellers feel rewarded, appreciated, and amply prepared to continue doing their best, every day. And, lest we forget, top performers always have somewhere else to go if you don’t treat them well. During the Great Recession, while millions of people were being laid off, there were still a few million people each year who quit their jobs and went elsewhere to work despite the dire economic climate. These are disproportionately people with highly valued skills, such as “rainmaking” salespeople.

 

Good treatment starts with resetting to realistic expectations. If your business is struggling, you will want to consider signaling adjustments to quota expectations and commission plans as soon as you can. Uncertainty of expectations, together with shrinking pipelines, lower conversion rates and longer sales cycles may send high performers a signal that their current gig has run its course and they should start looking for the next.

 

Do not lapse in providing more regular coaching to show you are invested in the deals your team is working and the skills and strategies they will need to close them. Even top performing sellers will encounter customer issues and selling situations in the coming weeks they have never encountered previously. You can’t expect them to navigate these new situations without real-time support. Virtual training and coaching are necessary modes of engagement now, and if you’re not already, you need to be prepared to offer these solutions ASAP.

 

2. Rethink Your Account Plans

 

This social and economic crisis is affecting every business differently. In some industries (travel, retail, etc.) activity is at a standstill. But other industries (CPG, Healthcare) can’t keep up with demand. Your sellers and your marketers need to understand and tailor messages/solutions account by account. Presenting the wrong message or the wrong solution in this emotionally charged environment could damage credibility and make repairing that relationship nearly impossible.

 

Sellers must take time to listen closely to their accounts as part of restructuring the plan. What, of a host of potential problems, are they prioritizing? How are they taking delivery of what they buy? How are they operating and serving customers? What is their market or customer base experiencing? You’ll be significantly better positioned to succeed if you understand clearly where opportunities are possible and where they are not.

 

3. Review Territory Coverage/Segmentation

 

This step may require a longer-term implementation, but it’s worth planning for now. After evaluating your account plans, you may find it necessary to pursue new markets and new customers to generate as much revenue as possible. Consider the following questions: Have you focused enough attention and limited distractions in the territories containing your key accounts? Do you have your best hunters focused as heavily as possible on generating new business in the customer segments that offer the greatest promise in the current market environment? Have you positioned relevant product expertise appropriately in territories with the best cross sell / upsell potential?

 

One more important thing to consider: Sparking the attention of new customers and moving them through a complex decision cycle in this economy will be a challenge. You’ll need skilled sellers who approach customers with powerful insight and build a compelling case for action. These individuals may not be the same “volume hunter” profile that worked in a market with high demand and customers flush with cash.

 

4. Align Your Insights to the Current Situation

 

Now, more than ever, your ability to offer meaningful, actionable commercial insight to your customers will be central to your success. But it’s likely your commercial insight needs a refresh. Just a few months ago, in a healthy economy, the most common challenge with commercial insight was finding a hidden problem significant enough to motivate customers to act. Now, the same customers are overwhelmed by problems affecting the core of their business. The challenge will be prioritizing the right one. Once you do, make sure you’ve done your homework to tailor it properly, deliver the facts with empathy and make sure the path to business improvement, using your differentiated solution, is crystal clear.

 

The good news is that tough times favor commercial insight. We know from years of researching decision-making that buyers are uniquely open to new ideas during crisis and will seize on new perspectives offered. But marketing and sales must act fast. Customers open to new ideas are also open to considering new sources for those ideas, including your competitors. Your ability to bring commercial insight that leads to customer improvement is the only way to truly protect these relationships.

 

Also, consider the full path for these fresh commercial insights. Have you mapped them into the buying journey, providing the necessary content to your customer Mobilizers to support building consensus and taking the opportunity to close? Has marketing incorporated them into the digital content ecosystem (website, email, social, webinar, etc.)? As both selling and buying become more virtual, the need for powerful digital content to spark attention, introduce insight and confront to motivate action is greater than ever.

 

5. Remove Sales Process Friction

 

Nearly all B2B sales organizations now find themselves needing to manage complex deals exclusively in a virtual environment. The same is true of the buying process executed by your prospective customers. This new operating environment, together with rapid policy changes on both sides, will introduce a lot of friction into the mix. An ounce of understanding/flexibility/ patience goes a long way to creating momentum and maintaining positive relationships with prospects.

 

More specifically, it is our belief that buying behaviors will likely not revert to the status quo ante. As companies find new ways to conduct business, purchase behaviors are bound to shift. In this environment, it may be necessary to temporarily relax your expectations of how business “should” be done. As you think of your current sales process, we think it is reasonable that the following pieces will need to adapt:

 

1. Demand creation activities will need to become digital native accelerating a trend that has been observable for a while. One hypothesis is that sellers will not fully regain access unless they double-down on insight delivery as opposed to being focused on solutions delivery. It is reasonable to assume that channel structures will change.
2. In times of stress, buying decisions always move up in seniority. In this environment, it becomes ever more important to identify the right mobilizer with the motive, and budget, to be able to rally behind a purchase.
3. Negotiation practices will likely change. Buyers may respond to increased risk by looking for more rigorous contracts. On the seller side, speed to respond will of utmost importance given that buyers may change their minds.
4. There will be a period where both sellers and buyers will have questions about each other’s financial viability. Sales will need to work closely with finance to address these issues.
5. As delivery and fulfillment requirements change, companies will look to protect their supply chains. Companies whose businesses have accelerated, will likely be looking to diversify supply and will want increased transparency.

 

 

To stay competitive, you need to be prepared. Being prepared is taking the right steps before you are forced to do so.

 

Sales and marketing teams now face the extremely difficult task of re-examining almost every assumption they made at the beginning of the year. In a matter of just a month, contexts have changed dramatically, and competitive positioning and business health mean something very different than they did in February. Maintaining business continuity in such a volatile environment is going to mean asking hard questions and taking decisive