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Use AI to help plan complex activities like SKO

Man with a microphone speaks on stage to a large crowd in a brightly lit arena.

“Culture eats strategy for breakfast.” – Peter Drucker

This famous quote emphasizes how a company's culture is more important than its strategy. A positive and empowering culture will lead to better strategy execution.  Having great events like Sales Kickoff and Presidents Clubs is essential in creating and nurturing the sales culture you want to build in your organization.

Man with a microphone speaks on stage to a large crowd in a brightly lit arena.

Sales Kickoff Events

Why are events like sales kickoffs so important?  There are a number of reasons that come to mind:

  • Alignment - They bring together all salespeople and leaders to get everyone on the same page regarding goals, strategies, new products, etc. This ensures that the entire organization is aligned.

  • Motivation - Kickoffs are high-energy events full of inspirational speakers, success stories, rewards, and recognition. This gets salespeople fired up and passionate about their role.

  • Connection - Sales teams are often geographically dispersed. Kickoffs allow them to connect face-to-face and build relationships with colleagues. Strengthening social bonds improves collaboration.

  • Education - Kickoffs provide an opportunity to train the salesforce on new products, sales techniques, market trends, competitive intelligence, and more through workshops and seminars.

  • Culture - From the tone of leadership to social interactions, kickoffs reinforce and amplify company culture. Shared experiences and rituals build a sense of organizational identity.

  • Strategy - Breakout sessions allow deep dives into territory, product, and account strategies. Reps return to the field armed with strategic insights.

  • Future-proofing - Companies preview new technologies, partnerships, and offerings at kickoffs to get reps excited about the future and prepare them to speak intelligently about the roadmap.

Planning these events requires a team that understands all these elements and more.  It takes a lot of time and effort across multiple teams across the company to make these events a success. 

If you’ve never done one of these before, or your company is newer, and you are creating your first one, this can seem daunting.  How do you make sure you’re not missing anything?  What questions should you be asking that you haven’t asked?  Hopefully, there is a seasoned sales leader in your organization who can provide input – but if not – let me suggest you turn to AI to help.   Here’s an example where ChatGPT, with the right plug-ins, can make all the difference in the world.

"Coming together is a beginning. Keeping together is progress. Working together is success." - Henry Ford

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Using ChatGPT

Note - You can watch a full video of these examples here: SKO Planning Video

How can we use ChatGPT to help?  You could start with a simple question to ChatGPT (or Claude) like “I need help planning a world-class sales kickoff event.  Can you help me figure out what should be included and how I plan for this?”  What you will get is output that looks something like this:

AI chat giving a step-by-step sales kickoff planning guide covering objectives, date, agenda, and budget.

It’s a good start - but we can do better.

A better question would be something like, “I'm responsible for creating a sales kick-off event for our sales organization next year. We have about 1,000 people that will be attending. We'd like to do all of the traditional things that need to occur in a sales kickoff (launching of new products and pricing, keynotes by senior executives, awards, training, recognition of partners, fun events, dinners). Can you act as a sales kick-off expert and walk me through a series of questions and options to create the optimal event from where we want to have it to what kinds of activities we should do??” 

There are two major advantages to this prompt: 1) It provides critical context for ChatGPT to better frame and answer, and 2) It gives ChatGPT specific instructions as to how you want it to interact with you. You’ll get better output that looks something more like this:

AI chat outlining sales kickoff location selection with venue types, pros and cons, and city selection options.

That’s great - but we can do even better.

ChatGPT 4.0 (the paid version) allows you to use plug-ins.  One that I use frequently is called “Mixerbox WebsearchG” – which allows real-time searching of the web.  This is incredibly useful for pulling current facts and analysis since ChatGPT’s training ended in 2021.  A second one that I think you will find incredibly useful for this and other activities is called “Whimsical Diagrams.”  Whimsical diagrams allows you to create flow charts and mind maps. 

Mind maps are an incredibly powerful tool that lets you visually organize and link together ideas, goals, and tasks.  It can help you see connections and relationships that you might not easily observe.  They leverage visual-spatial thinking to help integrate and structure information to encourage creativity, prioritization, context, and engagement with planning tasks.  They can help create far more organized, integrated, and thoughtful plans.

If you enable those two plug-ins, and then ask a question like this, you get a very different experience.

Chat message asking the AI to create a mind map of activities for a 1,000-person annual sales kickoff.

What you will get – is output that looks something like this:

Colorful mind map branching Annual Sales Kickoff Event into Venue, Training, Awards, Pricing, Keynotes, Dinners, and Sponsors.
Outlined list of sales kickoff mind map branches with sub-items, ending with an agree, modify, or add prompt.

You’ll notice that it’s asking me ABC questions (in this case, agree, modify, add).  These are part of my ‘custom instructions’ that I use in all queries (if you want to learn more, please reach out to me; I’m happy to share).

I chose ‘A’ and got this as a result:

ChatGPT screenshot listing venue options and decision points for an annual sales kickoff event

I’m going to pause sharing all of the screens here in this document – in the demo video, I keep going a bit further, and you can see how it will go down each branch (or you can have it pause and go deeper whenever you want) – and it would walk me through the entire thing.  This is incredibly helpful when planning events or making decisions.

Watch the full demo here —>: SKO Planning Video

Final Thoughts

This is another example of how ChatGPT – with the right prompting – can really enhance a RevOps team's effectiveness and efficiency.  From advanced analytics and trend analysis to detailed planning, there’s a lot that AI can help do right now – and it’s only going to get better.

I hope that you enjoyed this quick demo.  If there are things you would like to see or if you have any other questions on RevOps and AI, please reach out to me at steve@revopz.net

As always, it ends with a photo of Ollie.  He likes to ride along in the car when I drop my son off at school each morning and always wants to see where the action is.  He’s not quite as big as this picture makes him look – but he is a solid 165 pounds. 😉

Man in glasses takes a car selfie beside a large Saint Bernard dog

Best,

Steve

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