How to Host Sales Kickoffs That Engage and Energize Sales Reps

Remember back in pre-pandemic days when sales teams conducted lavish SKOs in person, perhaps with an option to dial in? Things are a bit different today. Some organizations are returning to in-person sales kickoffs, some are holding exclusively virtual events, and others turning to some form of hybrid event. Either way, the same challenge remains:

How can you deliver an engaging SKO that spurs reps on into the new fiscal year?

Regardless of format, the best SKOs have a strong theme and plan. They resonate with the audience and simultaneously guide alignment to business goals and objectives.

So what is it that makes these SKOs successful?

Types of SKOs

The rise of remote work has forced many sales organizations to rethink the way they run their SKOs. Planned correctly, any type of SKO can be successful.

In-Person SKOs

Traditional SKOs remain appealing for many sales teams. It’s easier to drive engagement in person, especially when hosted at an offsite location. Even for remote teams, in-person SKOs offer the opportunity to build rapport and relationships that may be lacking in day-to-day operations.

Drawbacks of in-person SKOs include extensive logistics, more time out of the field, and increased cost. These events require coordination across the sales team and need to be planned further in advance. However, some organizations decide to go the in person route for its many benefits.

Virtual SKOs

A virtual SKO has a high degree of flexibility and allows an organization to bring geographically dispersed sales teams together efficiently. Still, advance planning is important. Consider the technology and tools you have access to. Can you integrate existing platforms and enablement software? Are all presenters fluent in the technology they’ll be using? A mismanaged virtual event can hurt engagement before it even begins.

During planning, tailor the agenda to address the virtual nature of the event. You’re removing opportunities for in-person mingling, shared meals, and the like, so be sure to offer opportunities for sellers to connect with the rest of their team and get motivated for the year ahead.

Hybrid SKOs

Hybrid SKOs aim to combine the best elements of virtual and in-person events. The exact structure of a hybrid SKO may vary. One organization may add virtual pre- and post-event coaching and learning to an in-person event. Another might design an in-person event with the flexibility to include and engage remote sellers. Others might use the live event for team building and keynote speaker presentations while shifting organizational updates and training to virtual events.

Whatever the design, hybrid SKOs should be built so neither the virtual nor in-person engagements are an afterthought.

How to Plan an SKO

Done well, an SKO motivates sellers and clearly conveys key initiatives and priorities. Communication is key. The rise of virtual and hybrid SKOs complicates this, so make sure you account for this in your communication plan. Have a plan for how specific messages will be shared and in what format to resonate with your sellers.

1. The Golden Rule of SKOs: Know Thy Purpose

For most sales teams, sales kickoffs represent one of the highest-ticket line items in the annual sales budget. To ensure that significant cost translates into a business investment, spend extra time connecting the event’s theme and plan to the objectives you hope to achieve.

You might recognize some of the more common high-level objectives of sales kickoffs:

• Mobilize and motivate sellers before moving into a new phase of business (a new quarter, year, or business orientation)
• Align seller actions to the company’s business goals for the coming year (grow existing accounts, increase new client acquisition, etc.)
• Encourage specific sales behaviors (expand within existing accounts, maintain pipeline health, etc.)
• Teach specific sales skills to improve seller performance
• Celebrate wins among teams and individuals
• Build connection through relationship-building exercises

Though your SKO will likely encompass more than one of these purposes, it’s important to be as clear and specific as possible from the outset.

2. Build the Agenda

The agenda provides structure to your SKO and can drive engagement throughout the entire event. Look for opportunities to engage and motivate your audience.

Consider the following agenda items for your next SKO:

• Year in review: Include information about the previous year’s numbers, industry trends, and team wins. Take time to recognize top-performing sellers and celebrate successes.
• Team building: The structure and nature of a team-building activity may vary depending on whether your SKO is virtual, in-person, or hybrid, but should be aimed at encouraging interaction and collaboration among sellers. One activity that can begin at the SKO and continue afterwards is to pair sellers with an accountability partner. Have sellers write out their priorities for the coming year or quarter and share them with their partner during the event. Following the SKO, sellers check in with their accountability partners on a weekly basis to share their progress. This not only strengthens relationships on the sales team, but also improves the chances of sellers achieving their priorities.
• Networking: Even outside of formal events, provide opportunities for your sellers to interact with each other and other members of your organization.
• Strategic updates: These meetings might be spread out across the duration of the SKO, with each focusing on a different topic. Other departments, such as marketing, may also share their own strategic updates. Topics may include:
  • Strategic goals, including KPIs
  • Organizational developments
  • Changes to the sales process
  • Product/service updates
  • Industry trends
  • Competitive landscape
  • New tools
• Keynote speakers: For SKOs, keynote speakers are most often leaders or professionals who can speak to the state of your industry and provide your team with new perspectives. Speakers can also be motivational, getting sellers hyped to work toward their goals in the upcoming year.
• Sales training: The SKO is a great opportunity to introduce new tools, develop sales skills, and foster selling behaviors that are key to the organization’s strategy. As with everything else that goes into an SKO, tie training into the event’s theme and make the benefits of training clear.

How you organize the agenda is just as important as what’s in it. Break up informative sessions with opportunities to network or otherwise engage. Repeat key ideas and commit to your theme. Include meals and leisure activities in the agenda, such as happy hours or entertainment.

3. Plan Your Lead-in and Follow-up

Once you have the agenda set, with all the logistics it entails, share it with your team! This gives them the opportunity to plan for the event and get excited. Making all materials available on an event app is an easy way to coordinate communication and send updates to attendees.

Many SKOs also include pre-work, activities participants complete in advance of the event. Attendees will be flooded with information during the event, so it’s critical to set them up for success by introducing new concepts and giving them the chance to become familiar with new ideas and themes. Self-study works well here. Lessons and assignments completed in advance of the event can also cut down on time spent reviewing foundational concepts during the SKO itself. In addition, a review of assignments completed beforehand can give you insight into areas that may require additional attention either during or after the SKO.

Post-SKO follow-up can help reinforce new concepts, solidify habits, and help sellers apply what they’ve learned. Get your managers involved in coaching sellers and providing structured reinforcement. I’ll share more on the importance of post-SKO follow-up later.

Keep Sellers Engaged with These 7 Tactics

Even the most thoroughly planned sales kickoffs fall flat if they fail to resonate with sellers and engage them. Start with the seven strategies below for a more engaging SKO.

1. Minimize Distractions

Motivated sellers will respond to a good challenge. Start by challenging them to step away from their phones and notifications to focus on the training they’ll need to succeed in the coming year.

2. Invest in Environment

Whether in-person or remote, participants will find it difficult to engage with bland, lifeless environments. To the extent possible, choose polished and appealing venues and online interfaces tailored to your company.

3. Choose Hosts, Speakers, and Keynotes with Purpose

Think about the people your sales team will want to hear from. These might be organizational leaders, such as a CEO or VP of Sales, or interesting people from the outside world. When it comes to expert-led sessions and breakout groups, assign these to facilitators with both the charisma and direct experience needed to drive meaningful conversations.

4. Call Out Participants by Name

Across the board, encourage all hosts, speakers, and keynote presenters to engender an interactive dynamic. A great way to engage the audience is to call out participants by name to keep attention and encourage participation. For example, “Jeanine, I know you had a similar experience recently. Care to share a bit about that with the group?”

5. Complete Knowledge Transfer Before the SKO

Few sellers respond well to hours of being talked at or big blocks of “sit and learn” time. Avoid this outcome by taking care of the critical knowledge transfer of new concepts, ideas, and definitions before the in-person training event. This might come in the form of self-directed lessons, microlearning, or other activities that attendees complete in advance of the SKO.

6. Keep Sessions Short and Sweet

Expecting to maintain participant attention in four-hour chunks, without decent breaks, is setting yourself up for failure. That’s especially true for people attending the SKO online. Instead, design short, consumable sessions with one or two clear takeaways while leaving ample time for discussion and practice.

And don’t forget this important tip from Gartner: be willing to say no to sessions when planning the SKO. In the lead-up to a sales kickoff, many business units will see the event as their one yearly opportunity to capture the eyes and ears of the entire sales organization. Unfortunately, not every session will align with your goals for this specific SKO. Saying yes to every submission will dilute the clarity and impact of the SKO.

7. Prioritize High-Impact Activities

Instead of delivering lengthy training lectures, use the SKO to contextualize knowledge for how it applies to the sellers' world, which will give a significant boost to engagement. As to how to provide and practice real-world context, try:

• Peer-to-peer learning and discussion
• Breakout groups for specific topic areas
• Role playing, real-world exercises, and coaching
• Live polls for both in-person and remote attendees
• Quizzes and tests with live results to reinforce learning
• Live event chat for sharing opinions and questions

Maximize the value of time together by bringing knowledge to life using the ideas above.

Keep the Gears Turning After Everyone Goes Home

In physical exercise, there’s a concept called caloric afterburn. In short, your body will continue to expend energy even after the workout is complete, helping to maximize the effect of each workout. The same concept can be applied to the sales kickoff. The question is, how do organizations ensure their SKOs have lasting effect after sellers sign off and return to their work?

First, the outputs must be made very clear during the SKO. Sellers should walk away with a clear and specific understanding of how the information converts to tangible things that are going to create value for customers and the business. For example, if the goal of the SKO is to help sellers shorten sales cycles, sellers should understand why that will matter (to reduce complexity for buyers and improve close rate, for example).

Also, remember that 77% of learning is forgotten within 6 days if not reinforced. After the event, provide reinforcement of key concepts with online lessons, email sequences, and ongoing coaching. Space out repetition, reinforcement, and accountability checks across the coming weeks and months to improve knowledge retention and skills development.

Build It Right and the Motivation Will Come

There’s one last part of the post-SKO process: don’t forget to put your sales kickoff itself through a rigorous process of continuous improvement. That means evaluating and measuring its impact and using that information to learn exactly what’s working and what needs improvement.

In doing so—and by following the best practices above—you’ll design inspiring, honest, and educational sales kickoffs that truly energize sales reps to go win that next sale.