Making your 2025 sales kick-off a knockout success

The challenge

Sales Kick-Off (SKO) events are a familiar part of the professional landscape to most people who have carried quota and are an annual source of acute anxiety to sales leaders. These events typically cost a lot of money, require a ton of preparation, and create plenty of internal friction – and the return on all this investment of time, energy and money is hard to calculate.

Despite all these drawbacks, Sales Kick-Offs remain an essential part of the sales calendar, a punctuation mark to close out the last sales year and start the new. And for 2025, there’s the added pressure of helping salespeople redefine their value add in an increasingly digital world.

Key objectives

Ask salespeople what they like about Sales Kick-Offs, and they’ll tell you it’s the networking and opportunity to hear directly from senior leadership. Ask them what they don’t like, and they’ll roll their eyes and talk about death by PowerPoint.

This isn’t because salespeople have especially short attention spans. It’s because Sales Kick-Offs often lack clear objectives. We often see a three-way battle for agenda priority between:

1. Celebration
2. Education
3. Motivation

This is difficult to resolve because:

In other words:

The primary objective of the SKO is to improve motivation and confidence, not competence or knowledge.

Salespeople should leave the event filled with energy, feeling that they are doing an important job for a worthwhile organisation that fully supports them.

Motivate first, celebrate second, and educate a distant third.

Planning for success

So… you’ve taken a deep breath and decided to invest the time and money needed for the 2025 SKO. You’ve found a (shockingly expensive) hotel near a major airport, and you’ve worked out which dates will work.

The key challenge is now to build excitement and engagement with your team. With that in mind, you should:

• Send out preliminary questionnaires to the sales team to get them engaged and help define what should be on the agenda.
• Select a set-up that’s right for the event scale – making sure that you can manage breakouts and live feedback questionnaires/polling.
• Structure the agenda on the day so that no slot is longer than 30 minutes, 20 minutes probably better.
• Avoid stuffing too much into the agenda: if in doubt, leave it out.
• Include your customers – their input helps ground the event in reality.
• Budget for some follow-up training that reinforces the key messages. Remember that you are not trying to deliver education during the event.

Your SKO will be complex to deliver – and will require plenty of rehearsal to get right. It’s essential that you have a clearly identified programme manager with a well-defined plan. Don’t be tempted to give this as a “development opportunity” to one of your sales leaders: they have to deliver their year-end numbers and will not have the bandwidth.

Theme & agenda structure

Many organisations like to pick a slogan to act as a theme for the event. It’s tricky to find something that isn’t so bland that it’s cheesy but still has broad relevance to the audience (especially if the team is geographically dispersed). Try not to theme the event around a reality TV show that half the salespeople have never heard of. If in doubt, use the company slogan/strapline as a theme.

Probably more important than picking a theme is agreeing on what the tone of the event should be. While it’s admirable to try to build excitement and motivation with an upbeat kick-off, this tends to grate and have the opposite effect if coming off the back of a challenging final quarter for many people on the team. Be careful of over-egging how well “the business” did last year, if many individuals did not hit quota or struggled. Similarly, if people grafted and just about crossed the line above target, not conveying enough gratitude and instead emphasising “the improvements we’ll all need to make this year to ensure we stay ahead” kills all motivation. 

With all that said, what might a successful SKO Agenda look like? This obviously depends on the scale of your business and the critical challenges you face. Here’s a template agenda for a one-and-a-half-day SKO that may be a useful starting point.

Day 1

Travel to venue

11:30 Arrival & Registration

12:00 Lunch

13:00 Welcome & Introduction.

This should include a summary of inputs received from the sales team as well as laying out the agenda for the event.

13:15 Review of the Year.

Obviously, a focus on the results and big successes (which implicitly gives all the sales team up-to-date case studies) but also updates on important changes both internal and external.

13:35 The Value We Bring Our Customers.

Where you have external research, use it to highlight the areas where your proposition is both valued and differentiated. Alternatively, you could use a Q&A format with a major customer or a panel of customers.

14:05 Communicating Value Exercise.

5-minute video of a virtual customer call, followed by 10-minute break-out sessions in groups and a moderated feedback session. Have teams read out “What Went Well” and “Even Better If”. This can also be a useful tool to remind people of your standard sales methodology if one exists.

14:30 Coffee Break & Networking.

15:00 Inspirational Speaker.

A great topic for 2025 could be staying relevant in a digital world: how do salespeople continue to add value? Check to be sure that the speaker is cross-culturally relevant – and comprehensible – if you have a multi-national team. Sporting celebrities/ex-military personnel are high risk.

15:30 Live Poll.

For example, this could ask everyone to identify the single biggest skill they’re going to develop in 2025, with the main screen showing a real-time word cloud as the results are submitted.

15:45 3 Great Wins.

Have three salespeople present how they won important deals: 1 slide, 10 minutes each. Make sure that this is not just the biggest client/biggest deal, include deals that lots of salespeople can replicate. Check that they articulate the value from the customers’ perspective. Get them to explain how they tracked the deal through the funnel, multi-threaded, brought all the organisation’s capabilities to bear, overcame setbacks etc.

16:15 The Plan for 2025.

Share a clear and credible plan for the year ahead that is neither too complicated nor too simplistic: very high-level plans lacking in detail tend not to land with any impact or give any real guidance, while lots of detail and complexity immediately puts people off. Communicate what’s being prioritised, why and with what resources, as well as what is being deprioritised, mitigated for, or otherwise downplayed. Be realistic about sales velocity and competitive positioning. Do not use trite drivel like “let’s sell what’s on the truck”.

16:45 Live Poll Feedback on the Day & Wrap-Up.

Summarise the key themes, set the stage for Day 2. And of course, finish on a high note: make sure the poll questions are focused on the positives.

17:00 Networking & Drinks.

Depending on team dynamics and tenure, you may want to run an icebreaking activity to get people to meet colleagues outside their immediate team. This could be a classic like “two truths and a lie” or something that encourages them to find common ground e.g., pairs tasked up with finding the two most interesting things they have in common.

18:30 Team Dinner & Live Quiz.

Set the seating plan so that people are in their work teams with senior execs spread evenly throughout. Run a humorous quiz with silly prizes once people are sat down with a drink. “Name that baby” with everyone’s photos as a toddler is a hoot. Don’t make them wait too long before food – particularly if they’ve flown in in the morning. Free drinks on an empty stomach is a dangerous combination.

19:30 Awards.

This is classical recognition of high performers. Important that this focuses on activity as well as results – and on teamwork as well as individual performance. It needs to be heartfelt but crisply managed. Avoid giving “the same old faces” multiple awards, people quickly get cynical. Make a specific effort to recognise new team members who’ve got up the ramp quickly: talk about their lead indicators.

Day 2

08:45 Welcome & Introduction.

Re-cap Day 1, lay out the agenda for the day, try to get some energy back in the room.

09:00 New Product Demos x 3.

Live demos or at least videos of them, followed by Q&A with Product Managers on customer use cases, Features/Advantages/Benefits. Be realistic about launch timing, don’t set the wrong expectations for the sales team (and by proxy for customers). No slides allowed!

09:45 Coffee Break.

10:00 3 x Clinics.

Break out the attendees into three groups to run through three parallel clinic sessions, each of 50 minutes. Every attendee should attend all three clinics.

• Clinic A Commission Scheme.

Presentation of the FY2025 scheme with several worked examples, Q&A. Key point is to ensure that every salesperson knows what will make them money and how.

• Clinic B Sales Enablement.

Walk through of all the tools that the salespeople can use to make them more effective. This could include the Sales Playbook & Sales Guide, pitch decks, talk tracks, recorded examples of product demonstrations, e-mail templates, proposal templates etc.

• Clinic C CRM/Sales Tech Stack.

This should focus on how to use the system most efficiently, shortcuts to key fields, copy/paste pro tips, how to read dashboards etc.

13:00 Informal Lunch & Networking.

13:45 Sales Leadership Panel.

Have the sales leaders up on stage with a moderator, answering the questions that have been collected before and during the event.

14:15 My Biggest Deal in 2025.

Exercise – break-out groups with sales and supporting functions, brainstorming, senior leadership in each break-out, moderated feedback session.

15:00 Coffee Break.

15:15 Unveiling the 2025 Incentive Trip.

This is a natural sequel to the Biggest Deal exercise and is designed to build excitement.

15:30 Closing Remarks.

A final motivational boost from a senior leader, combining recognition and appreciation with a reminder of the organisation’s mission and purpose. Ideally the CEO in person. A limp-recorded video is probably worse than nothing; just don’t.

15:45 Close.

The pay-off

The world of sales remains challenging. The majority of sales reps continue to miss their targets (ca. 70%). Organisational churn is continuous; most CROs have less than 3 years in the role. Markets are disrupted by external events, economic uncertainty and technology shifts.

And don’t kid yourself that the SKO will compensate for poor sales leadership throughout the year. Creating a culture where you’ve put your people first for the past year means that half the job is done for you. If you have supported their personal development and well-being, they will be feeling positive overall about their relationship with you and the company. If not, you’ll have nothing in the “emotional bank account” and the event will be an uphill struggle from the start.

But the good news is that a well-thought-through Sales Kick-Off can still deliver a great motivational boost. You just need to make sure that it’s engaging, punchy – and well-planned.

If you’d like to know more about planning and executing your Sales Kick-Off event, let’s talk growth.