Do’s and Don’ts for your 2019 Sales Kickoff

Jamie Shanks
Jamie Shanks

Having participated in 100’s of tech company Sales Kickoffs (SKO) and witnessing the thousands of dollars to the multi-million dollar events, I thought it would be timely to share my observations, tips, do’s and don’ts in a blog.

Having participated in 100’s of tech company Sales Kickoffs (SKO) and witnessing the thousands of dollars to the multi-million dollar events, I thought it would be timely to share my observations, tips, do’s and don’ts in a blog. To help, I’ve also included an SKO Planning Kit you can download to help guide your team through planning your upcoming SKO. Good luck in planning for 2019.

Not all SKO are built the same! I’ve seen my fair share of extremely well-executed events and have also been to many not so great events. Most events have activities that can be broken down as follows: 


This one is easy, it’s time to celebrate successes and showcase your shining stars who killed it,  the big competitive steals you’ve had, the achievements teams have had, company new etc. 


I’m a big believer that people need to be self-motivated so building motivation in your event should be easy if you have the right people. You probably already picked self-motivated individual so in this category let’s think how we can be inspirational. What would inspire your team to think they are at the right company fighting for market share? 


“What are you going to do to be bold and different?” If you want to retain top sales talent you need to help them feel they are going to be challenged and inspired. They need to feel beyond the paycheck that your company is a great place to be. Talk about the vision of where the product is going, the growth that reps will be going through, show them how you are going to kick your competitors A$$ with sales strategy, sales training and development. 


This is the perfect time to have an information reset, new knowledge shared, new skills developed, communications improved and bringing the sales organization together to make sure everyone is on the same page with the mission and vision for the new sales year. Don’t mess this one up! 

Before planning your Sales Kickoff, you might want to have an understanding of the overall impression sales people have about SKOs.  Check out what people mentioned in a recent survey conducted by Brainshark – State of Sales Kickoff Meetings.

Kit: How To Plan, Execute And Drive Results At Your Sales Kickoff Event

Nearly 74% of the participants are of the opinion that the SKO does not merit an “A” grade, while 29% of the participants gave a rating of “C” grade or below. Social/networking activities were given a rating of “A” by 35% of the participants. However, keynote presentations were not received very well with only 16% giving them an “A” grade.

With the potentially millions of dollars your company will be spending on this year’s SKO, here are a few observations of dos and don’ts I’d like to share with you from the 100’s of kickoffs I’ve been a part of.


  • Everything should be focused around the company’s goals and objectives for that New Year. (IE If profitability then topics and coaching should be around being more profitable). Having a theme name is cool but you need to tie it back to the company’s goals and objectives.
  • Bring clients in to share why and how they bought. Let your sales team really understand what it’s like to be in your customers’ shoes. Have them share their buying journey.
  • Get the skills part of your training early in the event – tired minds don’t absorb. You don’t have to use this time for product training as it’s the easiest for reps to get a hold of that information. Try focusing on skills development early in your SKO and then product training.
  • Decide early what success for the event looks like and measure for that success.
  • Pre-learning and preparation should be a must. It helps to make your time together productive.
  • Make your event fun and gamified. You already know sales reps are competitive so bring them competition and fun.
  • Role Playing for skills-based training will help with retention.
  • Get your top reps to share successes and their go to market strategies used to achieve those successes. Peer-to-peer learning is the most relevant to your audience.
  • The most successful companies we’ve observed have made their SKO a business function with a celebration wrapped around it and not a celebration with a little business wrapped around it.
  • Set clear expectations around attendance and consequences for non-attendance or non-participation.
  • Make Sales Enablement an active part of the holistic SKO process.

Do’s and Don’ts for your 2019 Sales Kickoff


  • Don’t try to do too many activities – focus is the key. Focus on tying everything back to the main company goals and objectives for the year.
  • Don’t focus so much on product training. You have all year and all the support in the world to disseminate that information. Use this time so teach new selling skills like courses in social selling mastery, digital sales, ABSD, storyboarding, video selling, objection handling, effective sales research and so much more that doesn’t involve product knowledge.
  • Don’t forget your reinforcement plan post-event.
  • Don’t forget to use a feedback survey that measures your success. Many companies just want to know what people liked and didn’t like about the event. Make sure to measure against what success looks like otherwise you’ll only be grabbing general sentiment and that’s not a strong ROI for your event?
  • Don’t have leaders and reps in different sessions. This is the perfect time for each to gain new perspectives and learnings from each other. Being on the same page should be a part of your theme.
  • Make sure you don’t create a massive 4-day party at your SKO. What’s the ROI on a massive party? If you were personally paying for this event how would you run it?
  • Don’t accept latecomers who slept in because of a difficult night the night before. Your company may have invested millions so treat it that way.
  • Sales leaders and sales reps, this is primarily a business meeting with celebrations wrapped around it. Treat it that way! We have seen careers ended at SKOs for drugs, prostitution, fights, affairs and basic non-best-business practices. Of course, it’s typically just a minority of attendees but it’s a perfect time to remind people – “DON’T ruin your career it’s not worth it!”

Of course, this blog is not an exhaustive list but a reminder that the season for planning is upon us for many companies. This is why we have also prepared this useful SKO planning kit that you can download to help with your SKO planning season for the ultimate sales transformation. Good luck for the balance of this year and at your SKO next year.

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