The Execution-Driven SKO: Lessons from our Conversation with Tim Caito

The Execution-Driven SKO: Lessons from our Conversation with Tim Caito

Categories: Company Alignment  |  Sales Kickoff  |  Sales Training Initiative

This week, we hosted a webinar with Force Management Senior Partner Tim Caito. Tim is our resident expert on sales negotiation and has years of experience planning and leading sales kickoffs. He joined us to share his do's and don'ts when it comes to planning a sales kickoff that drives measurable results on company strategic goals and revenue objectives.

Keep reading to learn our takeaways from Tim Caito on the top three actions that will produce SKO results. If you find these valuable, check out the full webinar recording available on-demand. It was an engaging tactical conversation with some intriguing and relevant live audience questions.

1. Create an Execution Theme

When we think of SKOs, we often think of an event that inspires and motivates the team for the year. However, as Tim shares in our conversation, this is one of the most common pitfalls of sales kickoffs. That type of event fades quickly, and can even leave some participants cynical at being presented with goals, yet no roadmap to accomplish them.

The best SKOs have a theme of execution, rather than inspiration. They're tactical and focus on the Why and the How, not just the What. "You've got to think like an economic buyer," Tim says, "that sets strategic priorities and invests accordingly. Time, resources, focus." That economic buyer approach can help you ber discerning about what makes it into the sales kickoff agenda. Don't let your event get bogged down by everyone who wants to make an announcement or rally their team. When you adopt an execution focus, you consider every agenda item and initiative with a new context: Does this advance our strategic goals for the year? If the answer is no, maybe reconsider including it.

Hear more of Tim's insights on creating a SKO that enables execution starting at 25:07 in our on-demand recording.

2. Guide the Customer-Facing Team

In recent years, many companies have moved toward including a wider group in the sales kickoff. An event that for many was once just the sales team and sales leaders now typically includes Customer Success, Marketing, Product and adjacent teams. This represents an industry-wide shift toward enabling the entire go-to-market team, but that shift doesn't always translate to SKO programming.

Tim warns against too much customization to individual teams. While it is crucial to communicate an understanding of how SKO initiatives impact the day-to-day of each function, too much individualization and team breakout time can result in misalignment. "We frequently see organizations that bring all the different folks to their kickoff meeting, but then they send them down different paths," Tim says. "If you're locked in on what you're trying to accomplish strategically going forward after the SKO, you've got to have part of the SKO be focused on creating that aligned motion that we'll be executing on out in the marketplace."

Hear more of Tim's insights on using the SKO to generate alignment across the go-to-market motion starting at 16:03 in our on-demand recording.

3. Equip Front-Line Managers to Coach

Tim calls it an old adage: "If you want it to happen in the field, it only happens based on how much the front-line managers reinforce, support and guide to it."

We talk about this across much of our SKO content. Equipping managers to lead during and after the SKO is a critical step to ensuring your strategic initiatives actually make it into execution at the point of sale. Most leaders understand this to some extent. Where they may fall short, Tim shares, is in getting managers involved early, communicating the Why and the How, and following through.

Tim's advice on the importance of bringing managers in to your SKO initiatives early: "Get to them pre-SKO. Let them know, we're gonna show a new strategic direction. We're gonna set expectations on what we need your teams to do, and I want you to be crystal clear on what we expect out of you to be able to drive that."

When managers fail to adopt or take the lead on new initiatives, it's typically because they don't see the value, don't see it as actionable, or don't believe that it will be followed through on. Give a clear expectation of what managers can expect from you during and after the SKO - 30, 60, and 90 days on. Communicate what will be expected of them, and invest in their ability to execute on those items. Managers need skills training on not only your SKO initiatives, but on their ability to coach.

Hear more of Tim's insights on equipping managers to drive initiatives forward post-SKO starting at 41:00 in our on-demand recording.

How to Drive Measurable ROI from Your SKO

One of the main questions we received leading up to and during our webinar with Tim Caito was: How do I measure the impact of my SKO? Whether you're an enablement professional looking to deliver on company goals, or a revenue leader with your eye on larger revenue objectives and valuation, proving the ROI of your investment in a sales kickoff can be a challenge. The fact is that the ability to measure your impact lies largely in the planning that happens before the event. Tim's insights in our SKO webinar revolve around proving the value of your SKO activities, and he gives even more action items in the full on-demand recording. Check it out.

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