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4 Sales Kickoff Challenges to Overcome in 2022

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The sales kickoff event (SKO) is a time to celebrate, reflect, learn, and perhaps most importantly, gain a much-needed morale boost heading into a new year of selling. Whether planning for a virtual or hybrid SKO, enablement practitioners should consider what may get thrown at them and adapt swiftly.

The sales kickoff event is often met with excitement and anticipation across sales teams. There is tremendous value in creating a centralized and cohesive space to discuss new sales strategies, methodologies, forecasting, training, and goals for the entire revenue engine.

Throughout the planning process, enablement teams should consider the challenges of throwing a successful SKO to mitigate them. Enablement teams can brainstorm even more creative and effective solutions to execute a successful and engaging event for all participants by preparing for these challenges.

Here are four challenges enablement teams may face when planning a successful SKO and best practices to overcome them.

1. Mitigating Technical Difficulties

One of the most significant benefits of technology is the seamless integration in coordinating content, resources, presentations, virtual meetings, chat forums, and the like. At the same time, one of its more frustrating aspects is the multitude of solutions, and potential issues coordination can present in delivering a smooth experience for participants.

As enablement teams consider either a fully remote, in-person, or hybrid SKO event, it’s worth the time and investment to ensure that all systems are a go the moment the SKO begins.

Ensuring that all the technical specifications are squared away will help create that cohesive and smooth experience attendees will come ready to expect. Enablement teams should anticipate spending a reasonable amount of time with leadership and teams such as IT and operations to align on the tools needed for a stellar virtual experience.

This includes exploring how to deliver high-quality audio and video, coordinate breakout sessions, moderate a chat or discussion forums, schedule breaks, access training content or resources, and more. Ensuring that all the technical specifications are squared away will help create that cohesive and smooth experience attendees will come ready to expect.

“Even though organizations may have been using video conferencing tools to connect everyone virtually over the last year and a half, that won’t always meet the audio and visual needs of virtual participants when there are more than a few people in a room together,” said John Chinello, senior director of global sales enablement at Fastly. “For example, teams might need a way to connect a speaker’s microphone to the audio input for the virtual meeting, as well as high-quality cameras to show the speaker and bring the experience of the crowd to the virtual participants.”

Many organizations work within several systems to manage events (like video conferencing, mailing lists, or landing pages). Streamlining all integrations to unify the experience can improve ease of access for participants and reduce the risk of costly errors from juggling distributed sources. Similarly, it will be essential to build in time to practice run-throughs with speakers, test all equipment, and fix technical bugs before potentially hundreds or thousands of participants log on to their sessions.

2. Keeping Participants Engaged

Salespeople eagerly await SKO to connect and learn best practices or insights from one another. Ask a sales rep what their favorite thing about SKO is, and they may very likely respond with “the people.” One of the challenges for enablement practitioners is curating an agenda that builds in time for that connection while understanding the desired outcomes for an engaged participant. To help overcome this, consider making sufficient time for attendees to get to know one another and leverage breaks as a way to connect on a more meaningful level.

“We had a lot of 15-minute sessions on skill, on personal development, and we did a lot of Q&A but limited the time,” said Michelle Dotson, head of sales enablement at Zoom. “That allowed for a couple of things, it allows your attendees to have some breaks throughout their agenda, and it also allows them to know that this topic is not going to drag on.”

Engagement can be even more of a challenge in a virtual setting. To stave off distraction, incorporate a mix of formats for both learning and presenting. Instead of hours of a video call, consider including a discussion forum after a session, a live Q&A, icebreaker games, or brainstorming sessions.

If hosting a virtual SKO, take advantage of the remote environment and have attendees customize their agenda that fits their needs and own schedule. This can help encourage participants to be engaged in the topics they select based on their curiosity and goals, crafting an event that feels especially personalized to them.

3. Staying on Message

It may be tempting to spend a majority of time celebrating all of the tremendous wins the sales teams achieved over the past year, and for a good reason. Spending the time to give much-deserved praise and a chance for peers to recognize one another is a phenomenal way to boost morale. But it’s also crucial to acknowledge that SKO is looking ahead toward the future and what’s to come for sales teams.

Enablement practitioners can work closely with stakeholders to determine a central theme for SKO. Each session can tie back to a unifying message that provides reps with clarity and a sense of purpose heading into the event.

“For us, it was really important to cut down anything fluffy and extra, anything that was really taking away from the point,” said Dotson. “What people really want to know is what do you want me to learn? And what do you want me to do after I leave this session?”

In the planning process, taking the time to establish measurable and actionable goals can help establish the reason why the sales kickoff is happening in the first place. By directly aligning with the needs of the business, enablement practitioners can work hand-in-hand with sales leaders to understand where there may be gaps in understanding the state of the field and determine what strategies and methodologies may need to be explored. Creating value for sales teams is the main takeaway, and it’s up to enablement practitioners to help define what that value looks like.

4. Retaining Key Learnings and Insights

Sales teams may be excited and ready to tackle the new goals once SKO is complete – but to keep that momentum going, enablement practitioners can look for ways to continue to engage and celebrate the connection reps often feel from the guidance they’ve just gathered.

“We continue our SKO theme throughout the year,” said Callie Apt, senior of sales enablement at Domo. “We don’t want to limit it just to the event. We have post-event virtual backgrounds and templates and slide presentations that everybody can use.”

This could also mean generating more on-demand content mined from the sessions at SKO to be used in ongoing training, engaging with subject matter experts to facilitate future Q&A sessions, requesting feedback from participants on what went well and what could be improved, and following up with action plans on how that feedback will be implemented. By understanding the needs and expectations of the attendees, enablement practitioners can leverage these learnings to help influence future programs throughout the fiscal year.

It can seem like a daunting task to try and best a prior year’s SKO and create an impactful experience time and time again. However, with some thoughtful consideration, enablement practitioners can expect to not only pull off a successful SKO for all participants but also avoid the challenges that often plague SKO planning. With these best practices in mind, every practitioner can feel confident in generating momentum and hosting a sales kickoff that will be unforgettable.



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