How to Ensure Your Sales Kickoff Is Not A Colossal Waste of Money

It’s that time again! That wonderful time of the year where the sales thermometer resets to zero and your sales team pounds the pavement to deliver 150% over last year’s quota! Gather the troops, get them jazzed up and on the phones so they can quintuple the previous year’s results!

Right? That’s up to you.

As a sales leader, the Sales Kick Off (SKO) is that crucial moment of the year where you have a chance to build camaraderie, motivate your teams, and deliver a vision that is both audacious and inspiring.

Or, your SKO can be a colossal waste of time and money that will leave your sales reps questioning your leadership. I have attended more than my fair share of kickoffs and have experienced the good, the bad, and even a few nights that must have inspired “The Hangover.”

If you are looking to inspire your sales team this year with an unforgettable SKO, consider the following key ideas as you prepare to take the main stage in the shiny new blazer you bought for the occasion. Here goes:

1. Have A Defined Purpose 

It feels like a given: have a clear and defined purpose or goal of your SKO. However, I have seen countless leaders make the same mistakes year after year. Maybe he/she hires their buddy’s consulting firm to do a workshop. Then, one of the senior sales guys throws a rager in their hotel room. Last but not least, your VP of Product showcases a shiny new feature that you can’t actually sell. Sound familiar?

As your tired, hungover sales team files out of the convention center you booked, trudging over loose confetti you paid for and tossing the agendas Marketing worked so hard on in the trash, a feeling of dread sets into your stomach. Did I really just spend hundreds of thousands of dollars on hotels, food, and travel for nothing? Yikes.

Fortunately, you are already equipped with the tools to ensure this doesn’t happen to you or your organization. As a great sales leader (which we know you are; otherwise you wouldn’t have read this far) you strive to ensure your team has excellent anatomy to their sales calls. A key component to every good sales call or meeting is an agreed-upon agenda that is reviewed at the start of the call.

I advise you take the same approach when preparing and executing your SKO.

Meet with your leadership team ahead of time and determine what the primary purpose of your SKO will be. Ensure these goals are crystal clear by utilizing SMART goals (Specific, Measurable, Attainable, Relevant and Time Boxed) to define what they are and what they will accomplish.

After all, as John Barrows wisely puts it, “Goals give you something other than a quota to work towards.”

Some examples of your sales goals might be:

  • Increase the opportunity win rate from 20% to 30% this year.
  • Raise the average deal size from $22k to $27k this year.
  • 2x total revenue this year.

3 Ways to Incorporate Your Goals Throughout your SKO

  1. Use the opening session to introduce the goal and why you set it, then present the outline to your team of how you plan to attain it. Paint a picture for them. You are, after all, in sales!
  2. Have one or two of your top reps talk about what they did in the previous year to help drive toward the overall goal. This can inspire your team and motivate your sales team for a chance to share their successes next year.
  3. Facilitate breakout sessions where teams determine a few short-term things they can improve upon to help reach the goal.

2. Change Up The Format

My very first Sales Kickoff consisted of two back-to-back days in the same room. Everyone sat in the same seats to watch a series of PowerPoint presentations about unrelated topics for hours on end. Sound familiar? Sure, we had the occasional bathroom and snack breaks – I personally used mine to pound Red Bull and pop Excedrin.

Why are we still Power-Pointing people to death? Michael Brennan, CEO of Civilla put it best: I cannot recollect, in 30 years of work, a single PowerPoint presentation I saw or gave that altered the course of anything.”

Of course: there will be times where you have to show people something to get the point across. Consider your first key idea: is the purpose of your SKO to bore your team to death, or are you working towards tangible improvement? If you want your new strategies implemented and goals achieved, you will need employees who are engaged.

One of the most exceptional SKO’s I attended included several breakout sessions with games, each led by a department head, with a specific tie-in to the thematic purpose of the event. Employees were encouraged to sign up for sessions that intrigued them, meaning they chose to be there and were more engaged with the session.

3. Reinforce The Learnings: What Happens at SKO Should (Not) Stay at SKO

No, we aren’t talking about that embarrassing Facebook video of your VP of HR breaking it down on the dance floor. We are talking about getting your team to actually retain the information from your SKO. As a general rule, we humans are pretty awful at retaining information. Our downfall is in our memory. For example, there was a strange phenomenon on the internet not too long ago about how no one could remember if the actor Sinbad starred in a movie called Shazaam. Even Sinbad had a moment where he couldn’t remember if he was in that movie or not. In other words, memory is a pretty crazy thing.

No matter how energetic and engaging your presenters are, people will forget what they said. Even if your strategy is revolutionary and game-changing, your employees might forget how they were supposed to execute it. If you only let people hear things one time, they will forget pretty much all of the information.

If your goal of the SKO or the year requires a different selling method or a change to your sales team, the followup is crucial. As Laura Welch from Polycom pointed out:

“Why would I (as a sales rep) let go of the behaviors and workflows that have worked for me time and time again…When [sales reps] change, [they] at first…will need to learn to walk again.”

Changing methods or goals can result in low numbers and discourage sales reps—if they are not approached carefully or coached successfully. Be ready! When planning your SKO, have a post-show strategy to help reinforce your messaging and ensure your employees retain the message you have invested so much in delivering.

A few effective post-SKO reinforcement strategies include:

  • Group role-play during team meetings
  • Deal interrogation during one-on-ones where you ask questions specific to the SKO goal
  • Spiff small rewards like gift cards or team lunches when milestones are achieved
  • Make progress extra visible using business intelligence dashboards displayed on monitors
  • Daily stand-ups to check-in goals and team commitments


The SKO should be one of the most exciting events in your sales year. As a sales leader, this is your chance to have your own Tony Robbins or Indra Nooyi moment with your entire team. Take the time to outline specific goals. Freshen up your routine. Have a plan to reinforce your teachings throughout the year to make sure you get the most out of your team’s time and energy. Your annual SKO is an event that your team should enjoy, learn from, and tell others about for years to come. Get out there and have a blast!

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