We did the sales kickoff like that before. We have always done our sales kickoff this way. From my perspective, the kickoff was a success.

In the demanding environments of a selling organization, it is easy to forge ahead without taking pause to reflect on the past — or reflecting meaningfully. Especially with a large undertaking like a sales kickoff, starting with the building blocks from previous years seems like a smart and efficient move.

Yet there is always room for improvement. By reflecting on data and insights from the past, your leadership team can make better decisions and bigger impacts for the year ahead. And doing so for your sales kickoff program matters. This is your yearly chance to:

  • Bring your teams together to boost morale and deepen culture.
  • Motivate and inspire your salespeople’s best performance.
  • Transfer knowledge, enable with tools and share the go-to-market roadmap to unify all parties for the year ahead.

It can be a challenge to look at something as large as a sales kickoff from the past and try to glean key lessons for future planning. Sure, there might be key anecdotal moments that stand-out as clear successes or complete failures. Yet, it is important to build a proof-based case for how to best plan and conduct your sales kickoff for year-ahead success. Here, I am sharing some approaches for getting started.


Start with the numbers that matter. What was your company’s revenue performance? Did you meet or exceed your initial goal? Were there any outside factors that may have boosted or hindered your sales force? Your revenue performance is a key indicator of whether or not your sales kickoff was successful. Aside from the raw numbers, what other objectives were set for last year’s kickoff attendees? Did you hit or miss those?

Keep a pulse of enablement and skill improvement at follow-up and reinforcement sessions. Sales kickoffs are the start, not the end. Coming out of last year’s kickoff, did salespeople retain what your leadership wanted to? Were they able to showcase their knowledge and skills through reinforcement / coaching efforts and in live conversations with prospects? Or, did nothing really change in their competencies, sales skills, approach or effectiveness? 

Survey past attendees. Even if your current sales kickoff planning team has the direct memory and experience of past sales kickoffs, do not rely on this input alone. Turn to the people who sales kickoffs are built for: your sales force. Ideally, you completed a survey as an immediate follow-up to last year’s kickoff. If not, survey your stakeholders well in advance of your planning, and ask them what went well before — and importantly what did not and could use improvement. By engaging a larger breadth of your organization, you will not only get clearer, more comprehensive insights, you will also signal to them that their opinion matters to you. This way you start building their early buy-in and excitement for the sales kickoff program to come.

If your sales kickoff planning committee is struggling to gather insights from past years, identify how you can better track and measure success for your upcoming sales kickoff in order to have future lessons to guide you.


 A sales kickoff that makes an impact demands substantial time, energy and resources — and the outcome of the event often hinges on planning. Get the expert guidebook for sales kickoff planning best practices and frameworks — and set your organization up to win in the year ahead.