The Complete Guide to Sales Kickoffs

Tips, Trends, and Best Practices

Introduction to Sales Kickoffs

If you’ve landed here, you are likely thinking about a Sales Kickoff Meeting. Whether you’re considering launching your first SKO or if you’ve been hosting your sales team for years and are looking for a fresh perspective, this guide will help elevate your meeting. 

This resource acts as a step-by-step roadmap to creating the perfect sales kickoff and can be used a blueprint that provides structure and fresh perspective to those that may be overwhelmed by the mountain of tasks that go into meeting planning.

To SKO or Not to SKO?

You may not need a hotel ballroom set up with classroom style seating, or a 40 ft stage with rear-screen projection quite yet. However, if you have more than 25 sales reps, keep reading. For those who manage a small team, your first reaction will likely be one of hesitation. Your team may be in the same office, working together day after day. They may be so busy prospecting and selling that taking the time away feels unproductive. 

Regardless of the size of your sales team, nothing could be more important than intentionally coming together at the start of each year to strategize, plan, review, renew, and reenergize your sales engine.

1. Why SKO?

Reason Number 1: It’s a culture thing. 

The message you are sending your sales team when you make the important decision to bring them all together for a sales kickoff meeting is: YOU ARE IMPORTANT. We care about your needs, and we are committed to your success. This is the very first point we make, because culture is arguably the most important, but by far not the only good reason. 

“Culture eats strategy for breakfast.”
– Peter Drucker

The Top 10 Benefits of Hosting a Sales Kickoff:

  • Focusing on the goals for the year
  • Gaining buy-in and ensuring that everyone on the same train, heading in the same direction
  • Offering fresh perspectives on your products/services
  • Hearing directly from your prospects/customers
  • Sharing best practices
  • Recognizing exceptional team members (while creating the sense of competition salespeople thrive under)
  • Developing new skills
  • Building a sense of unity among your sales team & other key players
  • Being face-to-face bonds in an age of chats, video calls, and virtual meetings
  • Renewing and reenergizing your players
So, where do you start? 

2. It's all About the Goals

First things first, you must define your SKO goals & link them to the goals of your greater organization. This can be as easy as asking yourself a very simple question:

What do you need your sales team to do differently or better after the SKO? Is it qualifying? Discovery? Closing? Forecasting?

Fill in the blanks: Our SKO will be a huge succeses if within the next year, our sales organization can:

1. ____________________
2. ____________________
3. ____________________

Launch new products?

Add new customers?

Expand sales in existing accounts?

Implement a discovery process that shortens the sales cycle 20%? Increase close ratios by 15%?

Improve forecasting by 30%?

The next step is identifying the behaviors that need to be reinforced in order to obtain your goals for the year. Keep these goals and behaviors in mind throughout the planning process and when determining content.

3. Define Your Sales Strategy

Author and sales trainer Rick Page said it best in his #1 selling book “Hope is not a Strategy” (a great read if your strategizing a complex sale).

Your sales strategy should serve as a tactical blueprint for how you increase sales, revenue and profits, as well as a guide for helping your reps understand who your ideal customers are and how they can best sell to them. Your strategy should include clear differentiators, measurable goals and forecasted results.

The SKO is your best opportunity to set the course for the year by aligning your sales team with a common purpose, which includes an understanding of your strategy and a clear set of expectations, Research shows that sales strategy clarity accounts for 31% of the difference between higher and lower performing sales teams in terms of revenue, profitability, customer retention and employee engagement.

To ensure strategic clarity, buy-in and involvement, nothing beats a well-designed sales incentive program with a predictable and targeted communication strategy.

What About Sales Process?

There is often confusion around sales strategy and sales process. While strategy is the who, what and why, sales process is the when and how you manage your sales cycle from beginning to end. Following a tried and true sales process sets your reps up for success by ensuring higher quota attainment and helps management more accurately manage the pipeline.

The most successful sales processes are:

  • Buyer-focused
  • Clearly defined, simple, and repeatable
  • Flexible, allowing individual sales reps to capitalize on their strengths
  • Widely adopted
  • Continually evolving as market conditions change

4. The Case for a Theme

Talk of a “meeting theme” will have anyone who has attended an SKO envisioning a race car or a mountain climber. Themes are not an overdone gimmick. There’s a reason cars and mountains come to mind. It’s because themes work! They are mental hooks that tie together the theme, strategy, and actionable goals. What we are looking for here is professional and cohesive look and feel, that not only sets the tone and brings focus to your event, but according to psychologists, actually helps with the retention of information.

Have a little fun with it. A theme can help you incorporate humor, video clips, skits, jokes, etc. into your content. Don’t underestimate the value of adding a little levity into heavy topics or long sessions. Designed strategically, your theme can become your team mantra for the year, reinforcing your SKO message each and every month.

5. Content is King

Once you have clarified goals and strategy, it’s time to get to work on the agenda. Use your desired behaviors as a compass (gut-check) for all content that is incorporated into your sessions. If the content doesn’t tie back, cut it from the agenda and replace it with something that does. The most common mistake we see at

Sales Kick Off events is presenting content that does not align with the organizational goals and support the sales strategy. Remember, the main goal is to provide information & education that enables reps to execute the plan.

An SKO does take a good deal of time and attention to design and execute. Many sales organizations postpone preparation and end up with a 2 to 3 day focus on product training. While features and benefits are exciting and arguably relevant, the goal here is to offer tactical content that helps reps position products and features.

Don’t waste time on activities that will not change behavior.

What does tactical content look like? Focus on skills like creating a compelling vision, articulating the value proposition, and creating urgency.

Here are breakout session ideas that will change behavior and affect top-line sales:
  • Elevator Pitch Session: alight your team with the perfect 1-2-minute prospect pitch
  • Prospect Presentations: what happens when you are finally sitting face-to-face with your prospect? Review best practices for live presentations.
  • Role Play Sales Calls
  • Lead Generation: from online leads to prospect Road Shows, help reps cultivate new leads (link roadshow pillar)
  • Buyer Behavior: provide your team with the models of how customers make their buying decisions and the best way by which to manage each type of buyer.
  • New Account Penetration Strategy: share advanced techniques to reach new accounts through the use of email (video email is relevant in many cases), direct mail, and powerful referrals.
  • Competitive Marketplace Review & Advantages: highlight differences between competitive products & services and enable reps to make & defend product advantage statements.
  • Advanced Sales Skills: skip the basics and share the newest trends, including things like advanced sales psychology, sales linguistics, sales intuition,
  • Storytelling: teach reps how to use stories to connect with prospects on an emotional level.
  • Whiteboard Workshop: show how to create rapport and gain prospect confidence through whiteboard presentations.
Your reps will be more invested in content they had a hand in shaping. Survey to ask what they’d like to hear more about and gather user-generated content.
  • What do they need in order to be more eective salespeople?
  • What frustrations are common?
  • Where are people seeing room for improvement or issues that
    should be addressed?
  • Is there client feedback that should be taken into
    consideration.
  • Are there resource issues to be addressed? 

Pre-Work

To maximize the effectiveness of your time together, and to create an environment where your sales pros are excited and prepared when they arrive onsite, think about content you can send for review prior to kick off.

  • Clarification on territories, segmentation, compensation, etc.
  • Past performance/sales numbers
  • Communication of new sales goals
  • New Marketing plans
  • Updated Marketing collateral

Anything reps can read on their own will save time onsite and allow you to focus on your key content.

6. Speaking of Speakers

At the risk of sounding like a broken record, your goals should drive the decision of who is delivering your content (of course, your budget will play a role in the decision as well). Companies like Brightspot can help you engage the perfect speakers and presenters (training and keynote) to drive home your message.

Consider these Five Elements when thinking about presenters:

  1. Motivation: This is all about challenging and inspiring your workforce. You can look to personal hero speakers who can drive home a motivational message. Check out Nick Vujicic or David Goggins
  2. Inspiration: Change the way your people think and change them from the inside out with speakers like Brene Brown and Gretchen Rubin.
  3. Provocation: Does your business need a jump-start? Challenge your reps to kick some competitive butt! If you are looking for fire, Walter Bond will give you fire!
  4. Training: Regardless of the topic, this is all about engagement. Sales training workshops can be led by pros like Jill Konrath.
  5. Celebration: You want to make sure your team feels recognized and appreciated for all the work they put in. An energetic Emcee that can double as entertainment at your awards celebration works great here. Check out our friends Jeff Civillico and Joel Zeff. Or consider an Improv Group like Four Day Weekend.
Your Own Speakers

For an SKO (but please, ONLY for an SKO), internal speakers can be selectively utilized. Key leaders in your own organization may be the best people to share company information or messages of a sensitive nature (sometimes radical candor is just the thing needed at an SKO to set the tone for the future). However, proceed with caution! We’ve seen more than a couple of sales leader panels turn into flops, and the funny guy from Marketing is never the amazing Emcee you think he will be.

That being said, you can engage:

  • Department heads from other functional areas (assuming their topic relates directly to sales and sales goals)
  • Recent customers to walk through the process and why they chose your solution
  • Long term customers that can talk about why they stay and how to increase retention or create a customer panel and make it the “everything you’ve ever wanted to ask a customer but were too afraid (questions can be submitted anonymously via an App)
  • Industry Analysts or experts that are well-known known thought-leaders amongst peers

7. Location, Location, Location

Your initial SKO decisions will include where and when you will bring your team together. Here are the top 10 things to keep in mind when considering your destination and venue:

  1. How much space do you need? Sleeping and meeting room space requirements will be the #1 driver of venue selection. Keep COVID-19 social distancing in mind. You might need more room now than you would have in the past.
  2. Is your meeting mandatory for all attendees, or do you need to consider a destination with mass appeal that will draw attendance?
  3. Do you want a meeting hotel or Resort property? One is all business with fast wifi and a business center, the other offers opportunities to spread out and maybe a little pool time to recharge.
  4. Mercedes or Volkswagen? New or Used? Some companies will host their SKO at high-end properties with new, modern amenities (W Hotels, Ritz Carlton). Others want clean sleeping rooms and good lighting in the meeting space (Hyatt, Marriott). Decide what is important to you.
  5. Budget will also drive destination decisions – 1st tier cities like NYC will requite a lot more budget than tier 5 cities like Omaha.
  6. Is there free time or meals on own that require a walkable destination? NYC has a score of 88 out of 100 for walkability, while Omaha has 41 out of 100.
  7. Where are your attendees located? Consider meeting in the middle or alternating coasts in the US. Air lift and accessibility will be important factors with a significant budget impact.
  8. Will you meet in-person 100% or will you need a hybrid element?
  9. Is Eco-friendly important?
Third-party suppliers like Brightspot are an excellent resource for sourcing your events. We travel the world and know what properties are in excellent condition and which could use a little TLC! Best of all, sourcing is 100% complimentary!

Length of Meeting

Attention spans are short, and meetings can run longer than sometimes necessary. In our experience, 2 days seems to be the right amount of time to keep people engaged and have them out of the field. Some organizations can keep it to 1 full day and others will need a 3rd day. This will depend on the number of speakers you have, the amount of training you incorporate, etc.

Bottom Line: Cover critical content and leave room for networking. Face-to-face time with colleagues and executives usually ranks at the top of most SKO post-meeting surveys.

8. Focus on Wellness

Sales is tough. One of the most important aspects of a sales meeting is the care and feeding of the team’s mental health & wellness. This rejuvenation doesn’t necessarily come from a rah-rah let’s go get em’ speech. Rather, sometimes it’s the reassurance of knowing that they are not alone in their struggles and a certain amount of commiseration among colleagues is healthy. Encourage healthy discussions and sharing to drive this point home.

Wellness Suggestions:
  • Gratitude Wall: Get delegates to write their ‘gratitudes’ on post-its and post them directly onto a gratitude wall display.
  • Group Walk: Host a group walk (or 5k if you are ambitious) to encourage exercise in the early morning before meeting.
  • Stretch / Breath Breaks: Have the hotel gym manager or yoga instructor lead a group stretch and/or breathe at break
  • Meditation Room: A small, quiet room where attendees can escape to decompress and renew.
  • Yoga/exercise group classes: get attendees moving in a group setting
  • Food as medicine: offer healthy choices that decrease sugar crashes and increase attention spans.
  • Take the meeting outdoors: fresh air and sensory stimuli can reawaken a group, resulting in fresh ideas, inspiration, and relaxation.
  • Incorporate a curriculum that teaches lifestyle changes: attendees will go home with a new understanding of achieving work-life balance.
  • Highlight leisure activities: Make local maps available at your registration desk that outline the closest hiking/jogging trails, parks, and other active ventures
Competition in Wellness?

Sales is all about competition and bringing a bit of that healthy competition is the key to not only get your team excited, but to keep them engaged and entertained throughout the entire event.

Consider:
  • Leaderboards based on session or daily quizzes
  • Social media post contests
  • Gamification via the event App

9. Make Time for Networking

It’s very tempting to jam-pack your SKO with sessions and speakers, but equally important is creating some intentional space for mixing and mingling. These are salespeople, it’s in their DNA. This is especially important for larger, spread-out teams that don’t get the opportunity to bond and learn from each other on a regular basis.

Collaboration is the key to coming up with creative solutions, so leave room for those unplanned encounters to occur. And remember, networking can be harder for some. Consider ways of facilitating these experiences that make it easy and add value.

A couple of ideas:
  • Create your agenda with themed tracks. It is a way to connect attendees with people, products, and topics they are personally interested in, making it easier for them to connect with new people.
  • Schedule strategic meet-ups that bring like-minded individuals together when sessions are finished for the day.
  • Shake up group meals by either assigning tables with unlikely matchups, assigning a table lead to facilitate conversation, or introduce table topic cards related to the SKO content to give the group an icebreaker.
Incorporate new formats for intriguing breakouts:
  • Campfire Sessions: start with a speaker or speakers at the front of the room presenting an idea to a group of people. After 15 minutes, the focus shifts from the presenter to the audience, allowing attendees to drive their own learning and share experiences with others, which also assists with networking
  • Birds of a Feather: groups of people with a common interest or area of expertise informally working together. It’s often done over lunch or during the morning coffee break. BOF groups can be created, or participants can create their own via an App
  • The Solution Room: 90-120 minutes and designed to provide peer-supported advice on individuals’ most pressing problems. Each participant shares a challenge they are facing. Participants divide into groups of 6-8 and take turns sharing and brainstorming solutions
  • Lightning Talks: 12 speakers with 10-15 mins each. The brief requires speakers to make their point clearly and rid the presentation of non-critical information, keeping the attention of the audience
  • Silent Disco Talks: multiple speakers at once within the same room, while delegates can choose who they want to listen to. Participants wear wireless headphones and can switch between channels/speakers
  • Fishbowls: have 3-6 people speaking at any one time, with speakers seated in the center of the room while the rest of the participants (maximum of 50 people) sit around the outside and observe without interrupting
  • Soapbox: To allow attendee’s ideas to be heard, individuals can submit proposals to participate and will be given a short time on stage to present an issue that is important to them. Challenging views are encouraged
  • Storytelling: Storytelling sessions invite speakers to tell stories that reflect the authentic experience of an individual, a team, or a community but be told like a traditional story. Stories should be about 15 minutes long
  • Braindates: help delegates learn from one another through one-on-one or small group sessions (otherwise known as “dates”). Participants make offers and requests for knowledge on topics of interest and are then matched together
  • Genius Bar: create a casual environment where reps can engage with product and sales experts in a 1:1 discussion

10. After the Event

You’re putting in a lot of time, effort, and resources to create an inspiring event. A post-event survey is a must to gauge the overall ROO (return on objective), provide data about everything from the speakers to the foods and location, and give you action items for your next SKO.

Sales pro tip on reinforcing your message post-event:
  • Use your team meetings as a platform for sharing wins, losses, and stories that relate back to the learnings from your SKO sessions. Be sure each rep comes prepared to share something. These small reminders cement the information and drive behaviors.
  • Train the Trainer: Have your reps train new salespeople on the SKO learnings from a deck prepared utilizing SKO material. Studies show that when we teach what we’ve learned, we have a much better chance of retaining that knowledge.
Important things to consider for a post-event survey:

Timing: Ideally, your survey should be ready to send out before our meeting begins. The fresher the memory, the more enthusiastic the feedback will be. Include the link in a “thank you for attending” email the day the meeting concludes, or add the link to the home screen of your app

Include open-ended questions: Opinions tell a better story than numbers. Ask questions that start with how/what/why and invite your reps to explain their thoughts rather than tick a box or answer yes/no.

No one wants negative comments regarding an event they poured their heart and soul into planning. But know that 10 out of 10 times, when you ask opinions, you will get a few you won’t like. Don’t get defeated; remember that ALL feedback is valuable, and utilize the comments you can adapt to and grow for next year!

Unfortunately, research suggests that a large portion of the information attendees take in during a meeting will be quickly forgotten if not reinforced.

BONUS TIP: Hire an SKO Pro

Like your expertise in your industry, an SKO pro spends their days completely immersed in every aspect of the corporate event planning industry. They know the model inside and out and are well-versed in handling every need. Their mission is simple: make your job easier and to make you look great.

End-to-End Event Management of hotels, transportation, events, activities, participant support, and communications by CMPs (Certified Meeting Professionals) who do this all year long; they are faster, save you money, and reduce risks.

Websites & Communications to motivate participants to achieve more by creatively communicating with print, web, email, and apps and automating the winner’s registration.

Budget Management to make every penny count and keep your accounting department happy with full financial reconciliations.

Bottom Line:

A sales kickoff is a unique event that requires every tool in the meeting planner’s kit. It’s more than reserving a block of hotel rooms and meeting space. Experienced planners have seen great kickoffs — and not-so-great kickoffs. They’ve seen similar projects in similar industries for similar situations. “Best practice” is an overused phrase today, but corporate event planners truly offer best practice expertise.

Chances are you need fresh ideas, and as industry thought leaders, we are actively involved in meeting planner organizations, research groups, and trade shows to stay abreast of the latest research, trends, and new ideas to make your sales kickoff the best it can be! Drop us a line if you’re in need of fresh ideas – they’re always free!