5 Powerful Tips to Host a Sales Kick-Off Everyone Will Attend

If you suspect your sales team isn’t interested in a Globals Got Talent theme, you’re right.  

In this guide, Breadcrumbs speaks to four startup founders on what they’re changing (or have changed) for this year’s sales kick-off meeting.

1. Strategize for the aftermath 

The sales kick-off meeting is a catalyst for long-term business growth. 

Even though it only happens yearly, the insights you’ve gathered from the meeting shouldn’t be something that’s one and done. 

Rather, reinforce these insights all year round.

“Strategize for the aftermath of the sales kick-off meeting to ensure it remains valuable and meaningful,” says David Bitton, the co-founder and CMO of DoorLoop, a rental property management software company that recently raised $10 million in seed funding.

Roy Morejon, the co-founder of Enventys Partners, echoes a similar view:

“Hearing something once, no matter how grandly you state it, doesn’t mean your sales reps have absorbed it. Think about education. There’s a reason we study and revise something that we want to retain and work towards.”

Andrei Kurtuy, the co-founder and CCO at Novorésumé, too, feels the same way. Andrei, who previously worked as a business development rep at Queue-it, shares with Breadcrumbs: 

“Every year, these sales kick-off meetings face the same problem. They’re usually a snapshot of the company’s priorities for that quarter, product introductions, industry efforts, and revised sales procedures. Then you go on, travel home, and your sales reps may or may not remember the event.”

He continues, “Your sales kick-off affords you a once-in-a-lifetime opportunity to transition away from a one-size-fits-all approach to sales enablement and toward a more situational approach. By going beyond one-and-done enablement, you’ll be able to respond quickly to your company’s most pressing and strategic needs.”

Here are three ways to reinforce your sales learnings repeatedly:

(i) Create a dedicated channel for day-to-day sales initiatives

Building a single source of truth where employees can ask questions and gather information foster a knowledge-sharing environment. 

DoorLoop uses Slack as a central hub to discuss its best sales practices and upcoming sales objectives. 

The sales team is often reminded of the shared goals, emphasizing the strategies laid out during the sales kick-off meeting.

(ii) Set up a buddy program

37% of employees said that personal recognition encourages them to produce better work more often. 

Bryan Scudiere, the founder of Clear Path Development, instructs his senior sales reps to compliment junior sales reps for a job well done personally. 

This ensures that they feel noticed and fosters a sense of belonging. 

(iii) Get the leaders active

43% of employees prefer direct individual praise from their managers—all the more reason to actively involve the managers and leaders.

Roy Morejon, co-founder of Enventys Partners, shares, “They should coach all year-round and build relationships with employees to foster their growth and development.” 

He adds, “It’s far better to train continuously rather than in one fell swoop.”

2. Set identity-based goals

Identity-based goals are where the shift in selling happens.

And it’s backed up by experts.

James Clear, the popular author of Atomic Habits, believes that if you want to succeed in your goals, you need to go beyond outcomes and processes. 

He writes in his blog post, “To change your behavior for good, you need to start believing new things about yourself. You need to build identity-based habits.”

Bryan Scudiere took the author’s principle to heart and applied it in his business.

The sales manager, with ten years of experience in industries like B2B, real estate, and direct sales, shares about the Be Do Have principle with Breadcrumbs:

“Most sales leaders and managers coach their team with outcome-based goals. The better ones go into how-based goals. But few will set identity-based goals. And that level of depth is truly where the shift happens.” 

Let’s unpack how this looks.

A typical outcome-based goal might look like this: 

“Finishing the month strong.”

Whereas a how- or process-based goal looks like this: 

“Close 10% more deals and make 25 more phone calls a day." 

While it’s certainly more specific than the outcome-based goal, the problem is that only top performers perform well. For the remaining 80% to hit and exceed their sales target, you need to go deeper. 

This brings us to the following goal: 

Identity. 

Instead of a one-lined statement, ask these questions to get the sales team thinking: 

“How many phone calls does the No.1 sales rep make per day?” 

“What habits do they have when speaking on the phone?” 

“What do they believe about their prospects?” 

“What do they believe about the product, and how do their prospects respond to it?”

“In what ways can you improve?” 

There’s a strategic elegance to asking these deep questions, isn’t it? Utilizing an AI mock interview can enhance this strategy by allowing sales reps to practice real-time responses to difficult sales questions, helping them internalize the right habits and approaches.

Your sales team takes a step back to think about the actionable habits they need to build to close the sale while shifting their beliefs about the prospects, results, and how they sell.

“Since they’re writing these answers, it’s their words they’re going to believe. They buy into it more,” continues Bryan.

“We don’t rise and fall to the level of our expectations and wants. We rise and fall to the level of what we believe is possible for ourselves.”

3. Think workshop, not meeting

In the end, substance matters, not sizzle.

Don’t fall into the trap of brainstorming over-the-top themes and de-emphasizing what matters.

While it’s undoubtedly crucial for the sales team to unwind and celebrate the past year’s success, let’s not forget the primary goal of these annual events: Unlock revenue acceleration. 

One surefire way to make the most of your sales kick-off meeting workshop? Provide skill-based training to help the sales team win more deals.

A real-world example

 Let’s say you invested in a lead scoring system last year. 

Much to your disappointment, the adoption rate is low. 

Why not conduct a product training program during the sales kick-off?

Break up the sales reps into smaller groups and assign the product’s early adopters as leaders. These leaders should first ask the reps what they struggle with and walk them through how the product serves as a solution.

For example, if reps lament low-quality leads, (re)introduce them to lead scoring. Demonstrate how they can assign each lead a score based on their firmographic data and web activity. The higher a score is, the more likely they’re ready to hear a sales pitch. 
 



Data via Breadcrumbs 

Explain how when leads hit a threshold, the lead scoring tool will send all scoring information to the data source and notify them of the sales opportunity.

That way, sales reps can always ensure they’re focusing on quality leads. 

4. Show how to replicate success

There are multiple reasons salespeople attend sales kick-off meetings. 

And more often than not? It has little to do with the glitzy theme, games, or the CEO droning on about the company’s vision. 

What these salespeople really want is the answer to this question: 

“What does it take to be a successful salesperson, and what can I do to get there quickly?” 

(And yes, this is us plugging our lead scoring tool clearly this time around. Book a demo today to discover how Breadcrumbs help your sales team close more deals quickly!)

Earlier on, we discussed how skills-based training helps reps win more business. Now it’s time to add a dose of inspiration.

Host a panel featuring successful salespeople and their advice to light a fire in your sales team. Here are three potential questions to shape the discussion:

• “If you could turn back time, what would you do differently in your sales career?” 
• “What’s your most successful/favorite sales tactic?” 
• “What’s the No.1 skill that brought you to where you are today?”

Author’s Note: Coincidentally, the answers to these questions help shape the team’s identity-based habits and goals in point #2. So get on it! 

5. Offer the luxury to network 

Sales reps often spend a great deal of time out in the field negotiating with prospects and clients. 

Unlike the marketing and product department, they don’t have the unlimited luxury to interact with the higher-ups in the company—which makes the annual sales kick-off session even more valuable.

In the schedule, see that you include ample time for sales reps to network with the leaders they rarely see. 

Give them the opportunity to ask questions, build meaningful relationships, and show management they’re ready to move up into a leadership role.

“I’m pretty good at socializing with sales and support staff, but not as much with higher-ups and VP level folks. That has definitely hurt my career.”

– a Reddit user who works in sales

Pro Tip: If you’re a sales rep, network with people who (a) work behind the scenes and (b) are responsible for the success of your accounts. 

Reddit user McDray actively builds relationships with programmers and the support team. In the company, McDray is one of the few salespeople who can quickly solve problems and get a tech person to hop on a call in a short time.  

Without these unsung heroes, McDray probably wouldn’t be able to close the deals. Give credit when it’s due—publicly thank them for making these deals happen!

Party themes and self-serving keynotes are overrated in sales kick-off

Whether it’s helping them make meaningful connections with management they rarely see, improving their sales skills, or igniting their drive with success stories, empower your sales force so that you can all win as an entire organization and unlock revenue acceleration.