“We always talk about the success of the event or what we want to change, but we don't really talk about the things making our jobs hard as we're planning for SKOs.” - Nikki Schanzer

In this article, Stephanie Middaugh, Director of Enablement at WorkRamp, and Nikki Schanzer, Head of Sales & GTM Enablement at Hopin share their strategies to tackle the dreaded pink elephants of SKO.

Here are our main talking points:

  • The logistics of learner engagement
  • The fine line between over-prepared and underprepared speakers
  • Risk mitigation and contingency planning
  • How to deliver training?

Let’s go ahead and dive in. 👇

The logistics of learner engagement

Learner engagement in a hybrid or virtual environment

An image of 4 books "wearing" a set of over-ear headphones

Learner engagement, from a logistics standpoint, seems to naturally happen when you're in person planning a sales kickoff.

“What's the temperature in the room?” or “what are the chairs like?” are things we get feedback on frequently in surveys we send out.

However, in a hybrid virtual model, what are the logistical things we should be thinking about in that virtual environment?

One of the main elements of a successful in-person SKO event is the energy and the feeling.

How do you recreate this sentiment in a virtual or hybrid event?

Think about what three sentiments you want to get out of the sales kickoff - this should be directed not only to your audience but to your leadership team and the stakeholders involved.

Networking is something to be leveraged. For an SKO, the most important thing is to make sure that people are interacting with one another.

It’s important to figure out how to get our people internally to see each other's faces and talk about whatever it is they want to talk about. Networking naturally happens when you're in-person.

The virtual aspect of a sales kickoff is great because you can get more information across to your audience, but networking connections aren’t happening as naturally.

In a virtual SKO, you have to go that extra mile to figure out how to provide a space or an avenue to allow people to have those connections.

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You also have to bear in mind Zoom fatigue or virtual meeting fatigue.

As a leadership team, give your reps permission to be camera off for at least one session a day (and it can't just be a lunch break!). Some people need permission to disengage a little bit, and that's okay and pretty healthy.

If you're dealing with a multi-day SKO or six-plus hours on a Zoom meeting, you almost have to allow turning your cameras off so they can just listen and absorb the information that's coming at them.

The fine line between over and under-prepared speakers

The over-prepared, underprepared, and rogue

Image of the "see no evil, hear no evil, speak no evil" monkeys

Both of us have experienced these in the past:

  1. Overprepared speakers who are completely flat, and
  2. Underprepared speakers who come on stage and aren’t prepared at all.

There’s also a third category which is the rogue speaker, who comes in off the left-field and off-topic.

Speaker prep is so important. Asking the speakers what they’re comfortable with, giving them the layout sooner, and having prep sessions allows people to understand what works for them and what doesn't.

Even asking direct questions like: “What part of this are you not going to do?” will help you because you want people to tell you sooner rather than later.

I had an experience with an underprepared speaker - I made the mistake of putting too much faith in a leader, and on the day of the event when they came up on stage with just an iPhone saying: “Okay, I've got some got some notes for you guys”, I had a moment of panic.

You have to find the balance, especially with executive leadership, between babysitting without micromanaging them to make sure they talk productively.

Managing upwards can be tricky, and building trust with leadership early is essential. You have to let them know that you’re not here to nag or pester them in any way but are here to make sure we have a great event for the audience.

Keeping your message fun and dynamic

A person shouting into a megaphone

People tend to stick with what they feel they know or what they’re comfortable with because it’s the way they’ve always known it to be done.

We believe and urge people to shake it up and do things differently every year. Surprise and delight people!

For example, every year we had our business operations team go up on stage and they would talk about the new launches and data for sales or go-to-market, which is fine - but it’s not dynamic information.

We decided to make this segment recorded, even though this was a live event, and then we had everyone doing a new segment.

The result was fascinating because these speakers that I would typically prep to go on stage, who would come off as not the most exciting, made their segment fun and creative in a way I didn't even expect.

It covered the same amount of information that someone would spend 30 minutes conveying in no more than eight, and so it forced us to get crisp on what our message was.

We did it in a fun and dynamic way that we knew the audience would like in-person, but that you could translate to a virtual or hybrid environment too.

Knowing which of your topics aren't always the sexiest, and understanding the content and type of speaker you're working with is important. Then you can get creative around it because not everything has to be the same.

Knowing your audience and what they respond to well

Rows of chairs in an auditorium or stadium

The information sales ops needs are crucial, but how it's presented is often very dry, and it can be hard to work with stakeholders because you don't want to come right out and say: “I'm sorry, but that sucks”.

At the same time, you also have to convey to these leaders that they need to try something different and spice it up a little bit to keep people's attention.

With our phones and so much information coming at us all the time, today's learners have a short attention span so you’ve got to keep them on their feet and do different things.

Breaking the mold and being willing to work with a leader who's stuck in their ways and then suggesting little things here or there can make a big difference.

Risk mitigation and contingency planning

Risk mitigation and contingency planning happen naturally when we're in person. Virtually, aside from: “ Oh no! Our technology isn't working!”, what other day-of-the-event logistics should we make sure we plan for?

A direct line of communication behind the scenes

Three old-school wired phones

My biggest mistake, which I made a few years ago, was not having a way to speak to the presenters’ live.

At the time, we didn't have Slack, and the whole time I was trying to get someone on-stage's attention from across the room because they thought they had 10 minutes left but they had 35.

From then on, I realized a direct line of communication behind the scenes at all times was essential.

If you're doing something virtually, it's going to be in the platform or Slack more than likely, and educating people on what it's for is key.

It can be even harder to get people’s attention in a virtual world because they will close the Slack window or won't pay attention to a Zoom chat and they won't know where to look if you need to get their attention. Make sure that you educate them on where to be looking.

The other thing is, if something goes wrong, you need to at least have a line of communication and a backup plan or two as filler.

For example, if this person goes down or if their technology isn’t working, what's the video we can toss up, or do we have music videos we can play as a backup for those uncontrollable moments?

Don't try to cram in time!

A clock covered partially by a sheet

I feel like it’s in my nature when I'm on a virtual call to try and fill time but you don't have to.

If a speaker speaks too fast and there’s time to fill, turn off your cameras, go to the bathroom, get some water, play with your cats or your dogs, or take a couple of minutes to go outside.

Those contingency plans are crucial to making sure that everything stays. We’ll know it went sideways but ideally, your audience will think this was all part of the plan. You want them to feel like it's a seamless experience.

We can sense the audience needs a break too.

If the chat starts to die down when you're doing a virtual SKO, then maybe you’re hitting a wall and it’s time for a coffee break.

Building those breaks into your contingency planning is also a great way to secure a higher engagement for the rest of the event by avoiding screen fatigue.

How to deliver training?

Is SKO the place to train?

Several cardboard cutouts of question marks

I'm an enabler, I want to train people as much as possible - in the right way and when it's impactful - but also I don’t think SKO is the space we need to cram that in.

Maybe we’re at a sales kickoff to promote what's coming and that would make sense. Now you have the info, the next phase is learning and we're going to invest in you so here the SKO would be more tied to messaging.

We did a deal simulation with 300 people, with every role within a sales cycle represented.

I think it was good to get people to work in groups they wouldn't normally work in and understand what other people do in their roles but when I step back from that, the outcome was the same which was the connection.

Is SKO the place to train? I don’t know the right answer. If it's relevant to the theme of sales kickoff and to what we're all trying to accomplish during that time, then training makes sense.

When it's feeling extra, or if the sentiment is that we want people to connect, that doesn't have to happen in training.

The moral of the story here is: can we all take a critical eye on when this should happen to maximize learning? Is that at a sales kickoff or is it after? Do you sprinkle bits and pieces before, during, or after?

Rolling out methodology at SKO

Hands holding up post-it notes with: "to do, doing, done" written on them.

Sales methodology is a huge thing to roll out.

As enablement teams, we’re never able to critically show people the data that backs up why we've made the decisions we have, and our process for rolling this out.

There can be a fun way to do that but a lot of times we're rolling out methodologies because either the field or managers are telling us they need it.

If I'm in the audience at the sales kickoff, I want to know why we're doing the things we're doing throughout the rest of the year.

Taking an approach of: “You all told us this” or “We're seeing this in data with how we're selling, and here are the gaps we have - that's why we're doing this and introducing it at sales kickoff” could be a great way to get people excited about learning.

Essentially, it’s about them solving these gaps for the team to sell more and bring in more revenue.

Rethink how you’re presenting your information

Two piles of white A4 paper on a wooden table

Rethink or look with a critical eye at how you are presenting that information.

  • Can you do it in a panel?
  • Can you do it with a customer story?
  • Can you do it with someone like an AE who's great at a process instead of training everybody else?

If you want training to be a part of your SKO, which is completely valid, think about different ways to do it instead of just somebody at the front with a slide deck presentation lecturing to your audience.

Think about smaller groups, workshopping, whiteboarding, and the whole nine yards! Get them hands-on with some of that information. You can do a lot of this stuff virtually as well with a lot of great technology on the market now.

Thanks for reading!