Sales Kickoff Checklist

September 12, 2019

Read our sales kickoff planning eBook but can’t remember all the steps? Use this kick-off meeting checklist as a resource to make sure you’ve crossed all the t’s and dotted all the i’s for your most impactful sales kickoff yet.

Select a date and time for the event.

Since it’s called a sales kickoff, the earlier in your fiscal year you hold your annual sales kickoff, the better. The content you plan to cover should lend itself to the length of time you need for the event and can focus on sales reps and sales managers. One day is generally too short, while a full, five-day agenda can be too much, as retention and engagement will begin to drop off. Find the sweet spot somewhere in between during your decision-making process.

Select the location for the event.

Keeping your goals in mind, brainstorm locations that will both engage your sales force to participate and allow them to enjoy themselves. If you choose to hold your sales kickoff in the same city as your office, mix it up a little and find a place outside of your own building; a change in scenery will boost energy levels and be a catalyst for new, fresh ideas.

Determine what content is needed.

Both session and client-facing content should make up the bulk of your sales kickoff. A kickoff agenda that guides the training sessions allows attendees to follow along during the kickoff and refer back to in the future, while members of the marketing and customer success teams can introduce new client-facing sales collateral, giving context as to how and when to use various decks, one-pagers, graphics, etc. during a successful sales meeting.

Determine an event theme.

Create a theme surrounding the goals of your sales kickoff that your team will rally around and can carry throughout the remainder of the year, such as sales enablement. This theme will set the tone for the agenda and content of all sessions. Plan specific activities and provide fun swag items that tie in with the theme.

Decide and confirm speakers.

Choose speakers who a) make sense given the subject matter, b) have the authority to speak on certain topics, and c) demand respect and attention from sales reps. Include internal sales leaders as well as individuals outside of your sales organization.

Select an event overseer.

Sales people love the opportunity to talk, and getting many together in one room can lead to lengthy discussions. While these are sometimes be productive, other times they detract from the purpose of the session and waste time, which is why it’s beneficial to elect an emcee who monitors time and makes sure things stay on track for the attendees. Choose someone outside of the sales team who won’t need to actively participate in strategy sessions.

Arrange for travel and accommodations if applicable.

You may choose to hold your sales kickoff in a different city or state than your headquarters, and even if you stay close you may have remote employees that do not work in the local office. If some or all need to travel a far distance for the sales kickoff, book flights and hotel rooms as needed, ensuring everyone gets to the right location with sufficient time to get to the sales meeting location.

Rent/arrange for all equipment, technology and other tools needed.

Plan for the presentation and session materials in advance; everything from computers, projectors and the proper connectors, to notebooks and pens for reps to take notes with. Have this all set up in the room beforehand so you don’t waste time setting up during the sales kickoff.

Arrange for meals and refreshments at the venue.

Supply your attendees with breakfast and lunch for full-day meetings, along with plenty of drinks and snacks to get them through the day or days of strategy sessions.

Create a schedule for sessions.

Once you have confirmed all the sessions, craft a schedule putting them in an order that makes sense. Try to mix things up and not put two “sit-and-listen” training presentations consecutively, and add in 15- to 30-minute breaks every couple of hours, and if possible find time for individual sales coaching opportunities.

Plan social activities.

After a full day of learning from a sales trainer and leaders, sales professionals can be physically and mentally exhausted. Give them the opportunity to let off some steam and enjoy themselves with group activities. Team dinners, an escape room, sports game or other entertainment is a great way for attendees and leaders to have fun, bond with one another and feel relaxed when they return for the next day’s sessions.

Distribute invitations, agenda and supporting content to all sales kickoff participants.

Providing important content ahead of time gives meeting attendees the opportunity to read through learning materials beforehand to prepare questions, and can also serve as a resource to reinforce training post-sales kickoff.

Plan post-sales kickoff sales training and materials.

Speaking of reinforcement, you will need to offer sales training and certifications following the sales kickoff to boost retention and build upon what was learned. Make training through videos and other bite-sized, mobile learning materials convenient and readily available for sales reps to view on the go and on their own time.