coaching and reinforcement

New Webinar: Scaling a Culture of Coaching & Reinforcement

Implementing a sales methodology makes your sellers better. They sharpen their skills, your pipeline fills up, and your win rates grow. Everybody wins, right?

Well. Not so fast. The Ebbinghaus curve finds that learners will forget 87% of what they’ve learned if it’s not reinforced within 30 days. All that wonderful knowledge you just invested in? Poof. Gone.

To maximize your investment, you need to embed coaching and reinforcement into your company’s DNA. And we’ve got a respected sales leader from Connection, a Challenger client and Fortune 1000 company, coming to our next Winning The Challenger Sale webinar to show you exactly how to do that.

On May 16 at 10 a.m. CT, join Dennis Riseman, Connection’s vice president of sales, and Ian Goddard, Challenger’s vice president of advisory, to learn scalable strategies for embedding Challenger into your organization, including:

  • The reasons why change management fails — and how to address it
  • The strategies that Connection uses to build a culture of coaching and reinforcement, creating buy-in with leadership and cross-functional skills adoption
  • The importance of Connection’s Mobilizer Council — what it is and how you can replicate it at your organization.

Bring your questions and be ready to learn from one of the top sales leaders in professional services, at a company that Newsweek twice called one of “America’s Most Trustworthy.” You won’t want to miss this engaging and exciting hour.

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coaching a team

On-Demand Webinar: How to Build a Successful Reframe

Challengers know that strong sales conversations depend on establishing and delivering a powerful Reframe within the Commercial Insight choreography — a compelling idea that teaches your customer something new and changes the way they think about their business.

Is your Reframe working hard enough to disrupt your buyer’s existing beliefs?

In this on-demand webinar, we invited two sales leaders to share a real-life Reframe with our experts for a live feedback review, which was packed with practical guidance on building and executing a successful Reframe that changes your buyer’s perspective… and changes your sellers’ win rates.

Michael Schaumberger, principal executive advisor and global head of insights and messaging, and Charryse. Bigger, enterprise account executive, led this session and walked through:

  • The key elements of the six-step Commercial Insight choreography
  • How to build and consistently deliver a powerful and motivating Reframe
  • Effectively tailoring your Reframe by listening to understand

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coaching a team

On-Demand Webinar: Crush Constructive Tension in Commercial Teaching

Customers want to work with sales reps who offer unique perspectives that help them think differently about their business. Sellers need to understand what drives a customer’s assumptions and how to expose flaws in their current approach.

The way to ensure sellers are equipped to give customers what they want? The fundamental Challenger skill of commercial teaching.

And getting commercial teaching right means getting a lot more comfortable with making your customers uncomfortable.

In this session, Challenger experts demystify the key skills within the Challenger Selling Model, specifically how to leverage constructive tension effectively when leading a customer through a commercial teaching conversation.

Watch the webinar recording on demand to learn:

  • Myths that surround the Challenger methodology — no, being a jerk never sells anything
  • How to coach sellers to ask powerful questions and use silence to uncover buyer assumptions
  • Real-life examples where creating tension resulted in moving a customer toward a signature

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On-Demand Webinar: Creating Buyer Urgency amid Indecision and Uncertainty

The economic landscape continues to change, with less dire predictions than last year. Inflation declined, consumer optimism rose, and despite increased interest rates and tech layoffs, labor growth continues.

Even with these positive signals, B2B buyers remain cautious and hesitate to make purchase decisions.

The problem isn’t an uncertain economy. It’s that buyers fear making a change, or worse, making the wrong decision. With the right strategies, sales leaders can show their teams how to leverage tactics that drive urgency for change.

In this on-demand webinar, Andee Harris, Challenger CEO, and Lauren Graves, head of learning design, lead an invigorating session on how to create change and mitigate buyer risk, in any environment.

You’ll learn:

  • How to identify signs early in the sales process that lead to late-stage losses
  • Tactics to help buyers understand the cost of inaction
  • Strategies that guide buyers to invest in change without fearing failure

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On-Demand Webinar: The Art & Science of Improving Forecast Accuracy

Buying and selling is in a chaos spiral — and it’s no wonder that sales leaders struggle to achieve forecasting results that they’d term “predictable.”

Improving forecast accuracy is a science — but it’s also an art. No one is ever going to get it 100% right, but by digging deep with the right buyers, asking powerful questions, and using conversational intelligence to assess what they do, you can build a forecasting system that delivers predictable results on a cadence that works for your organization.

In this lively session, Challenger’s Dan Flood and Ines Tamaddon unpack:

  • how to evaluate the right buyer behaviors,
  • build a thoughtful forecasting culture, and
  • leverage technology to ensure happy ears don’t get in the way of reality.

It’s the reality check every pipeline-and-win-rate-obsessed sales leader (read: every sales leader) needs.

Download this on-demand webinar to find a better way to approach forecasting today.

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Business woman talking to her colleagues during a meeting in a boardroom. Group of happy business people working together in a creative office.

On-Demand Webinar: Uncovering the Best Tactical Insights of 2023

Phew, what a year. Are we right?

But before you activate that OOO and start practicing “Auld Lang Syne,” let’s reflect on the insights that changed how we sold in 2023:

  • How to sell in a sideways economy
  • Understanding today’s B2B buyer
  • The power of teaching, not pitching, in your sales conversations
  • Why you need a healthy, high-performing sales culture
  • …and much more

Now available on demand from the Leading The Challenger Sale webinar series, Challenger’s Maggie Knauff and Ian Goddard will parse the lessons we learned this long year and think about how sales leaders can bring them forward into 2024.

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On-Demand Webinar: A Fight to the Finish

Struggling to bring your stalled opportunities out of limbo and into closed-won status?  

Geoff Hendricks, key account executive at Challenger, joins CEO Andee Harris to discuss how to overcome common obstacles buyers face, the cost of customer inaction, and how a mutual action plan brings both buyer and seller together to complete the buying process. 

Tune in for a practical guide to closing your pipeline, with tactics and strategies that work, even in an uncertain economy. 

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Expert Tips for Planning Your Next Sales Kickoff

In our September webinar, nearly half of the attendees said the started planning their yearly sales kickoff in Q3. Another quarter won’t start until the middle of Q4. Whether it’s a matter of procrastination or prioritization, we hear that sales leaders tend to put off planning their biggest sales gathering of the year, starting well beyond the point they should.

The truth is that to achieve the SKO of your dreams, you can’t afford to wait. If you’re struggling to start, try this step-by-step, repeatable process used by SailPoint’s enablement leaders, Global Revenue Enablement Associate Manager Robin Barde, and Global Revenue Enablement Manager Meredith Linze. For more, watch the full on-demand episode of Leading The Challenger Sale.

What makes a great kickoff?

Maybe your first reaction is “really great swag and a 1:2 person-to-happy-hour ratio.” You might not be wrong, but a truly functional sales kickoff must also achieve several goals. 

  • First, it needs to set the tone for the year. Sellers need inspiration after a tough quarter closing their pipelines, especially following a year of economic uncertainty. Identify how your team needs to feel when they leave the SKO and use it to guide your planning. 
  • Second, think about how you’ll align sellers and revenue teams with the organization's goals and values. Your organization must speak with one voice at your SKO, emphasizing what's important at an organizational level as well as what’s at stake. 
  • Next, recognize that while the SKO energizes sellers, that energy needs to be pointed in the right direction. Sellers should leave the event able to clearly articulate their focus for the year to come. 
  • Finally, yes — it should be fun!

Choose Your Theme

What ideas are you kicking around for your SKO theme? Since you’ll build the rest of your event (ahem—swag! Workshops! Breakout sessions!) around this idea, conversations about the theme should start early and can begin as soon as the end of your previous SKO. Grab a whiteboard, block an hour on your calendar, and make a list of stakeholders whose input you’ll need. 

Prioritize: 

  • Feedback from your planning team
  • Insights from leadership
  • Insights from your previous SKO’s attendees 

Once you've aligned on an overall theme, consider a tagline. SailPoint’s 2023 SKO, “Sail Forward,” featured the tagline “Faster. Tougher. Together.” Executive speakers and keynote presenters drew this thread through their presentations and even included it in company meetings throughout the year.

Define Your Goals

With a solid theme in place, it’s time to outline your SKO goals. If the theme drives the overall feel of and messaging around your event, then goals help dictate the content. 

Remember that different teams might have different goals. Your enablement team and sales leaders might want to emphasize certain tactical skills or revisit your recent sales training program. Leadership might want to lay out their strategic vision for the year. Encouraging all your stakeholders to articulate their vision can help you settle on the right goals for your event. Each SKO session should map back to those strategic goals. Your follow-ups — training, sales meetings, even your company’s all-hands — in the year ahead should do the same.

It’s all about giving reps what they need to walk away from the SKO feeling confident and excited about meeting their objectives. 

Drive Interactivity

You know that your kickoff will be exciting, that your theme will serve as a rallying cry, and that your speakers will reinforce your goals. But how can you keep your sellers engaged, especially with a full schedule and so many things pulling at their attention? 

Our guests recommended tapping into interactivity, particularly through gamification. That might be as simple as asking them to participate in a photo competition. For our SailPoint guests, selecting an adorable mascot with layers of meaning helped give sellers a focal point. The SailPoint team also used an app to get real-time feedback from sellers. Those tuning in remotely could connect with a live broadcast feed between sessions.  

Plan to incorporate activities that unlock your sellers’ competitive instincts. Adding fun competitions and building opportunities for engagement will keep their attention and increase stickiness, too. 

Plan for Reinforcement

On that note, our SailPoint guests’ final suggestion was this: the SKO is just the beginning of a year-long enablement journey. If you don’t follow up with reinforcement, you risk sellers losing nearly three-quarters of everything they learned within days

To make sure your SKO efforts aren’t wasted, you’ll want to create a reinforcement plan that pulls your theme and goals through to next December. This might look like: 

  • Equipping frontline managers with a “meeting in a box” to help them revisit SKO learnings with their direct reports
  • Planning to add any materials to your learning management or sales enablement platform after the event
  • Creating a feedback loop for participants to submit questions and identify areas where further training is needed 

Effective SKO Planning Starts Now

We hope these steps from expert SKO planners jumpstart your planning journey. No matter where you are in the process, the time to start is now. For more inspiration, including SailPoint’s speaker preparation process and a template you can use to prep your speakers, watch the on-demand webinar “Practical Tips for an Unforgettable SKO.” 

Want to watch the next Leading the Challenger Sale webinar live? Sign up for the series here.


On-Demand Webinar: A Challenger’s Guide to Account Growth

Q4 is here and your account managers’ focus has turned to making quota by end of year.  

Your product delivers.   

Your service couldn’t be better. 

Yet your existing account growth is flat.  

Watch A Challenger’s Guide to Account Growth to find out why your accounts aren’t growing — and what you can do to shift the conventional wisdom at your organization and unlock serious growth potential before year-end. 

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On-Demand Webinar: Practical Tips for an Unforgettable SKO

Your sales kickoff (SKO) is THE opportunity to energize your sales team for the year ahead.  

A well-executed SKO propels your team forward with purpose and clarity — and maybe even a little fun. On this webinar Kate Feldt, senior director of global key accounts at Challenger, welcomes Robin Barde and Meredith Linze, the dream team behind SailPoint’s legendary SKOs. They discuss the nuts and bolts of planning to create the right balance of education and celebration, along with practical tips for speaker selection and prep, gamification, and creating effective networking.  

Watch the recording for everything you need to know to build an SKO that ignites your sellers and gets everyone ready to crush their goals.

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