An Interview With Dionne Mischler: How to Host the Ultimate Sales Kick Off

Dionne Mischler, CEO & Founder, Inside Sales by Design

When it comes to invaluable sales training resources, there’s nothing that quite compares to the Sales Kick Off (SKO). As Founder and CEO of the sales consultancy Inside Sales by Design, Dionne Michler has attended and hosted her fair share of SKOs and knows exactly what to look for.

“A good SKO has a theme and a universal direction,” Dionne said. “It has planned content, planned downtime, and planned follow-up.”

What it doesn’t have? “An open bar!” Dionne jokes. “But honestly, this isn’t a vacation and it isn’t a party. Sales leaders are trying to foster a community with reps and should be smart about the type of environment they’re creating.”

In our first conversation with Dionne, we talked about transitioning SDR teams from outbound to inbound-focused roles. Here, we’re back talking about all things SKO-related and how sales leaders can make sure the momentum lasts throughout the year.

What does an effective SKO look like?

I can definitely tell you what an ineffective one looks like and it’s days and days of speakers from all over a company speaking directly to sales reps in classroom-style seating about off-topic agenda items. I’m sure the content is amazing, but is it consumable?

What we see work really well is a staggered, fresh approach to content and education. Have someone from your senior leadership team come in and give a keynote talk to establish the mission and theme of the SKO as a whole. Then, everyone else who speaks should address the universal theme.

At the end of the day, the purpose of a sales kick off is to invigorate and re-energize a sales team. You want to give your reps a reason to fall in love with the product and the company all over again. It’s important to not lose sight of this goal in the middle of planning.

How can you balance the exciting areas with more tactical, operational topics?

I’ve always found that if people know why you’re talking about a particular subject, they’ll listen better. An SKO can’t be a hodgepodge of different topics. So, if you spend time talking about fun, exciting wins and then go into what might not have gone as well, it’s important to make the takeaways very clear to your reps. Also, give them a follow-up resource that creates a conversation about the more tactical topics afterward so reps know how to actually use these new skills in the real world.

How can you ensure that follow-up content and resources are actually used after a SKO?

The first thing I always recommend is to build an app! Sales reps spend so much time on their phones already so it’s just taking advantage of this channel. There can also be some company-mandated takeaways if you want to go that route. For example, everyone should leave the SKO knowing exactly what their goals are and what leadership wanted them to learn. There shouldn’t be any confusion, so you might want to share a note-taking outline beforehand to give some guidelines around what your reps need to focus on during the kick off.

What other departments should be involved in a SKO? How can sales leaders foster a company-wide ‘team’ mentality at this type of event?

My motto definitely is the more the merrier! As long as your speakers are on theme, you can bring in everyone from product to customer success to marketing to speak to your reps. I recommend helping other departments come up with the messaging so we can tie everything together around the theme. At the end of the day, your reps are the ones spreading your message, so every second of their education should count.

As far as cross-departmental team mentality goes, it all comes down to orchestration. If you have a sales-focused leadership team, they’re probably going to focus on all sales all the time. But if your leader is more interested in team wins, they’ll want to highlight everyone who helped win an account along with the sales rep, from the field marketing rep to the service team members involved, and so on.

How do you balance talking about new business with reducing churn and driving upsells?

While new logos are always exciting, you need to find a way to make the existing account side just as exciting to talk about with your team. Keeping customers and retaining relationships is just as if not more important than bringing in new business. Sales leaders should continue to encourage relationship building and time investments with customers alongside the new business wins.

Do you believe in giving reps homework before a SKO?

Honestly, it all depends on your organization. I’m a huge fan of preparation – luck and fortune favor the prepared. If you’re going to assign homework, just make sure it’s relevant, has a purpose, and adheres to the overall theme. I will say that homework is a great way to make sure people’s heads are in the game and they aren’t just showing up to be there. They’re showing up because they’re ready to learn.

What are some practical ways to keep the SKO momentum going throughout an entire year?

Go for a combination of formal and informal touchpoints. Sales leaders can tie-in key takeaways with annual or quarterly reviews while managers can strike up informal conversations over lunch or during a weekly chat. It’s all about making professional development a necessity on your team throughout the entire year, not just for a few days at a SKO.