The Annual Kickoff
By Russell Bourne
It’s December, and if your fiscal calendar aligns with the actual calendar, with good discipline and a little luck, your annual planning is close to done. Needless to say, those of you on non-calendar fiscal years can apply the content of this article to match the start of yours. If you need a refresher on annual planning, our CEO Kristen Hayer recently published a 6-part blog series on best planning practices for a Customer Success organization:
Segmentation and Journey Mapping
Building the Business Case for Budget
While a solid strategy is the foundation of a successful year, it has to be followed with execution - and step one is your team kickoff. A solid kickoff is especially important if the new year represents a major change from the previous one, but it’s still important in cases where the new year’s plan is similar to the old one. Remember, you may have new team members, the team’s day-to-day may have drifted off course over the year, and a year is a long time - you’re probably overdue to share or reinforce the team’s purpose and plans at a high level.
Before continuing, it’s worth refamiliarizing yourself with best practices for Change Management. The Success League developed a 4-part change management framework, nicely summarized here. We’ll refer to the 4 change pillars throughout this article.
So, what does a good kickoff look like?
Make It An Event
An annual kickoff is a big deal, and you need to be big about it. If you lead a remote team, this is a great opportunity to bring folks together in person - in fact, it may be the only opportunity they have to see each other in one group all year. If your team works together in an office on a daily basis, take them somewhere else if you can; a day rental at a local hotel or other event venue is just fine. Either way, try to start the kickoff with a social event on arrival day. Socialization is a natural icebreaker and will put everyone in a receptive state of mind.
Interrupting their normal routine is great for morale and makes the message memorable later. This brings us to our first change pillar, which is to make your message BIG. Small messages aren’t compelling. Create a vision in which the upcoming year of your CS function’s contribution has an unmistakable positive impact for any combination of the company’s vision, the company’s finances, your customers, and your employees.
The Big Group Meeting
If you’re a CCO or VP-level leader, assuming your Customer Success organization includes multiple functions or at least multiple job roles, start your kickoff with a full-group meeting. The content should apply to everyone in attendance, so think big picture here. Remember your big vision? Now is the time to use it as a catchphrase, or even as the name of the summit.
For example, let’s say your company just landed a new investment round, which comes with more resources and higher expectations. The name and theme of the kickoff could be “Liftoff” and you could incorporate airplane-themed images into your slides. Cheesy? Yes. Memorable and on-message? Also yes. (This author surely has former colleagues who are reading this, and our old company actually used this theme in a kickoff over 10 years ago. See? Memorable.)
Again, the content in this meeting should never dive into detail to the point where it only applies to one of the functional groups in the meeting. You can ensure your big-picture message is accessible by running it by the team leaders ahead of time - this is the second change pillar, recruiting advocates. Ask for their opinions on how to best communicate the message given their team’s past year performance, team morale, team understanding of the bigger strategy, and so on. Holding these sessions with the functional leaders ensures their buy-in, and gives you a chance to train them on the messaging, both key factors in them cascading communications to their front-line folks. Enlist the help of the ones with the most adaptable, sociable personalities to get positive momentum from the start.
Breakout Groups by Function
After your opening keynote, it’s appropriate to hold breakout meetings for each functional group. The team leaders should host the breakout for their group, and they’ll lean on the buy-in and messaging from your leadership planning session. It’s also appropriate to get into deeper, team-specific details in these meetings. For an expansion team, that might mean an introduction to new products or sales motions, or the first communication of the team’s quota for the new year. For a support team, it may mean any changes to the ticketing system or team SLA goals.
Team leaders should expect that whatever material they cover in these meetings will need to be repeated multiple times throughout the team, especially within the first month. With strategic ideas and with change, you cannot overcommunicate - and communication is our third change pillar. Remember to cater to different learning and communication styles. Most people are visual learners, but at some point make sure you provide the content in spoken word and writing. If there are new processes to teach, you can present them as a demo during the breakout meeting, but make sure to follow up with one-on-one, sandbox, or shadowing later.
For revenue teams on any kind of quota, remember that money - both in the form of income and quota - are stressful subjects, often to the point of being taboo. Save conversations regarding individual concerns for 1:1s.
Follow-Through
It’s worth having a brief closing keynote to close your kickoff event. A final social event isn’t a bad idea, either - it gives people a chance to digest what they heard, and for teammates of different functions to talk openly about how they can help each other.
Our fourth and final change pillar is to employ incentives. In practice, that means front-load your new year’s plans with easy wins, and make sure to recognize them in a visible way. Recruit your social and creative team members to come up with contests, prizes, and so on to gamify the early parts of the plan. People will start to believe the annual plan is winnable by seeing the early successes!
Obviously, this article is written with the C-level or VP-level leader in mind. If you’re a Director or Manager-level leader whose senior leadership isn’t planning an annual kickoff, you can scale down the advice in this article to apply to a singular functional team. Since it would be a shorter program, you could possibly make it work remotely, though in-person is still ideal.
If you believe an outside voice would help - or if you want to outsource the public speaking! - The Success League is here to help. Ask us about our Kickoff engagements. Best of luck in the new year.
Russell Bourne - Russell is a Customer Success Leader, Coach, Writer, and Consultant. In a Customer Success career spanning well over a decade, his human-first approaches to leadership and program management have consistently delivered overachievement on expansion sales and revenue goals, alongside much friendship and laughter. Russell serves on the Board of Gain Grow Retain as co-lead for Content Creation. He is passionate about equipping individual contributors and business leaders alike to lean on their Success practices to grow their careers and help their companies thrive. He holds a BA from UCLA, and in his free time plays guitar semi-professionally.
