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The Enablement Leader’s Guide to a Successful Virtual SKO

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Posted in:  Sales, Sales Enablement, Sales Enablement Strategy

Sales kickoffs, or SKOs, typically require a massive investment – and not just in event overhead.

Every minute that reps spend at your SKO is time that could have otherwise been spent driving revenue – creating enormous pressure to justify the cost. Companies attempt to cram all formal learning for the year into a packed agenda; when the event is over, it’s business as usual with nary a follow up in sight.

This approach is antithetical to the way people learn. As a result, SKO content is usually forgotten soon after the event.

So how can enablement leaders drive real impact through their SKO? By applying the Path to Mastery to their kickoff approach. Let’s take a closer look at what this means.

What Does a Great SKO Look Like?

The goal of every SKO is to ignite some sort of behavioural change, whether it’s selling a new product, adopting a new tool, or simply evolving their sales skills. In order to successfully drive change, your SKO must embody the key principles of how people learn.

Thus, to understand what goes into a great SKO, you must first understand how people learn. Effective learning boils down to practice over time.  Think about studying for an exam: knowledge gained by cramming is forgotten faster than knowledge gained over an extended period of time. The latter approach is formally known as “spaced learning” and can help people remember up to 80% of content after two months.

For an SKO, 80% knowledge retention two months after the event is an excellent outcome: it implies that reps are understanding, retaining, and applying the new behaviours you set out to teach them. How can you ensure your SKO delivers the same benefits? With the Path to Mastery.

Applying the Path to Mastery to Your SKO

The Path to Mastery is a repeatable framework businesses can use to codify and scale winning behaviours across their sales organisation. It consists of four steps:

  • Providing resources and context
  • Providing training and structured practice
  • Driving and coaching application with customers
  • Analysing impact and accelerating the Path to Mastery 


Through these steps, businesses can deliver training and coaching that adheres to the learning best practices we just discussed.

You can apply the Path to Mastery to your SKO by spreading out when knowledge is consumed and applied via pre-work before the event and ongoing training after. Bookending your SKO with training and coaching ensures that knowledge delivered during the event is retained – and eventually, applied to customer conversations.

Best Practices for Virtual SKOs

Now let’s take a tactical look at what it means to apply the Path to Mastery to your virtual SKO by breaking down the key activities that should take place before, during, and after the event.

Before SKO: Build Foundational Knowledge with Pre-Work

Core to the Path to Mastery is learning foundational concepts via repeated engagement with training materials. With regards to your SKO, this means exposing reps to new concepts and content prior to the event itself via prework.

Though it may not sound exciting, pre-assigned coursework pays dividends. First, it relieves pressure on the SKO agenda, ensuring your event doesn’t turn into a multi-day lecture. Additionally, pre-work allows materials to be delivered in bite-sized pieces. This gives reps a chance to learn at their own pace, on their own time.

Well-designed pre-work should build in spacing, repetition, and short application exercises in a variety of media formats. Enablement teams should lean into their enablement platforms to deliver this content and track engagement.

During SKO: Build Momentum

Your SKO itself should be an energising event – one that builds momentum behind the learning taking place.

Focus your sessions on helping reps under the why behind changes you’re asking them to undertake. Your messaging should reinforce that these new behaviours are a major initiative for the company and showcase the success of early adopters. This can be achieved through motivational speakers, breakout-room roleplaying, competitive team challenges, and other interactive activities.

While this phase isn’t an explicit part of the Path to Mastery it is important nonetheless – and the best use of a large group’s time.

After SKO: Drive Real-World Application

Once your SKO has wrapped, continue down the Path to Mastery by focusing on driving real-world application with continued practice and coaching.

At this point, your reps will have consumed new information but may not have put it into practice. Practical application is, however, how most of us learn: we take in information, but then need to contextualise it and be able to play it back in a way that means something to us personally.

For example, say new industry-specific messaging is rolled out at your SKO. To ensure sellers have mastered the learnings, you can request they submit a video recording of the content, played back in their own words to their managers within a month of the kickoff.  This moves the sellers into an active learning mode and also makes them revisit the material, both of which are critical to retaining it over the long term.

All this, however, is just practice.  None of this counts if the sellers don’t actually use the new messaging with a customer.  The best companies track which sellers have applied the new material in the real world within, for example, a 60-day period.  If you don’t see the adoption you want, it poses an interesting set of questions:

  • Do sellers believe the content will resonate with their customers?
  • Are they feeling confident enough to try the new messaging?
  • Are sellers getting the coaching they need from their managers to successfully land the new messaging?
  • Are managers reinforcing the importance of the new messaging, and creating accountability for their teams?


Managers, of course, are a key link in this chain.  Getting their commitment to this process up-front will ensure that you have buy-in on the thing you are trying to roll out.  If managers don’t think it’s worth their time to coach and reinforce, it probably isn’t worth the teams’ time at SKO, either.

Done right, this process is all about building muscle memory.  Regular repetitions, over time, build something powerful.

A Successful SKO from the Start

By applying the Path to Mastery to your SKO, you can ensure that the event drives meaningful change for your sales team.

Ready to supercharge your SKO? Dive deeper into training and coaching best practices with my Definitive Guide to Sales Training. And stay tuned for the next chapters of the Definitive Guide to Sales Training and Coaching, which will explore how people learn and how you can build effective training based on those principles.

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