Planning Sales Kickoffs

We are live. Thanks everybody for joining to talk about sales kickoffs. I’m here with Roz Greenfield today, who’s done closing in on or maybe surpassing a 100 of these. Roz, do you mind sharing your quick background on what you’ve done in enablement and with SKOs in particular?

Yeah, absolutely. Thank you for having me. Excited to have this conversation. Happy Friday, everybody. Yeah, so I started out as a salesperson, as an SDR back in the day, when a phone book was what they gave you to call from. So I just aged myself, but that’s the truth. Moved into B& AE, sales management. And that was when I realized it was really like the enablement part of it that really got me going. And I started working in enablement.

My life led me to an acquisition into Oracle, which was a great opportunity for me to really be able to test a lot of things in a very large organization with nice budgets. And then eventually left there after a few years and started the enablement function at Optimizely. And a few years ago, seven or eight years ago now, founded Level 213, we’re a boutique enablement firm.

And sales kickoff or go- to- market kickoff or revenue kickoff, whatever you call it these days, we can talk about why that name has evolved, has been, for me, one of the most exciting projects that fall on enablement’s plate each year. I think it’s really an opportunity for the enablement team to shine whether you’re a team of one or a team of 100, it’s really an opportunity to you to show the organization what you’re made of. And it’s kind of like your massive Superbowl.

And I’m not a sports person, believe it or not, but that’s the best analogy I’m coming up with right this second. And yeah, like Kate said, I think I calculated 108 STOs at this point, some bigger, some smaller, and obviously we were all forced a couple of years ago to figure out how to do remote and in- person and hybrid. And so, and it’s one of my most exciting things. It’s a tremendous amount of work to do it right, but if you get it right, you can make a tremendous impact on the organization. So excited to talk about that for the next hour.

Awesome. So I guess what is kickoff or as you alluded, maybe it’s not called that anymore.

Yeah, and it’s kind of the name’s kind of evolved. So originally it was a kickoff or sales kickoff or SKO would be, or SCO would be what we refer to it. Now, a lot of people are calling it revenue kickoff, go- to- market kickoff. And so a sales kickoff is, or the kickoff event is the, typically at the very start of the new fiscal year, where you bring the revenue generating teams together, which is, it was always a sales team, but now people realize like, oh, we should also have the customer success team there or the account management team there.

And oh, marketing makes sense to be there. So it’s kind of evolved to your revenue generating teams or your go- to- market teams, which is why the name evolved. But it’s really an opportunity to start the year off right, to do a look back and a look forward and to put an injection of energy into the organization after you’re coming out of Q4, whether it has been a good year or a bad year, Q4 is going to be hard. It’s been challenging to be a revenue generating employee the past few years. That’s just the fact.

And so this is really your opportunity to kind of get the injection back into the teams. And it’s typically an event that’s done in person. Although I mentioned a few minutes ago, we’ve obviously have been forced for a few years back during the pandemic to do them remotely. Now companies are doing some remote, some in- person, some hybrids, but it’s really just kind of bringing everybody together to kind of get the year off right and to set the agenda for the year.

One of the things that I like to remind people of is that the word kick off is an incredibly important word in there. It’s not a once and done event or shouldn’t be a once and done event. It should start your year. And then hopefully is part of the agenda of what the enablement team or the go- to- market team will be working through throughout the year. But it is kind of like the main event show to start that year off.

Awesome. So let’s get into why. I mean, this is a huge investment in time and money. Why do you do it?

Yeah, and it’s typically the biggest investment that a company will make on their internal team. Very often you’ll have a similar style event for your customers, but this is for your internal team. And the investment is not just in, obviously the cost of the event itself, but if you think about taking every revenue generating employee and putting them in a room for a week, whether it’s a virtual room or a live room or a few days or whatever it is, they’re not revenue generating in that particular day, in that particular time.

So it’s obviously a tremendous amount of investment of time and of your resources, of your selling teams for a number of days. So why do it, right? So A is to really start the year off right. It’s a really great opportunity to look back. What worked? What didn’t work? What did we learn?

And then to look forward.

What are we doing? What are we doing now? It’s a really good time to reset balance. Typically, a lot of things in the organization has changed. What are the priorities for the year? And then what are the priorities for this organization that’s here, whether it’s a sales team or the entire go- to- market team? It’s a really good opportunity to.

do some sort of a training or advance a specific agenda and also to celebrate and have fun for the sake of fun, right?

Your team just worked so hard to close at Q4 or to close at the year.

They’ve gone through the rollercoaster ride and sales is a rollercoaster. Revenue generation is a rollercoaster. It’s high risk, high reward.

And giving them that infusion of energy becomes a tremendous opportunity.

If you’re a remote workforce, which is very typical these days, and even if you’re not, but you have offices all over, it’s an opportunity to bring people together and have them be able to interact with each other in a way that they might not normally interact. Also, if you’re bringing multiple roles together, it’s an amazing opportunity for roles of people to interact together in a way that might not normally happen.

Even if you’re in the same office every single day together, you tend to sit with your group of people.

So those are some of the really great benefits of why you make this investment in time and money and effort to kick off the year in this way.

Awesome. We talked about it being an investment. We had a question, what’s a good budget? Is it per head? I guess any guidelines you can give.

Yeah, that’s a really good question. And I’ve seen it. I see it anywhere between the numbers are going up because the cost of doing things are going up.

The cost of travel, the cost of hotel.

But I would say, and obviously the more people that are coming, the more negotiation power you have.

And I’ll talk about that in a second.

But I would say I see anywhere on the low end to a thousand a head to on the high end to five thousand a head. And that’s a very big range.

But I would say the average is about two thousand to twenty five hundred per person.

And that includes travel, accommodations, food and events. I do think that the more people you have coming, the more negotiation you have with the event location. And one of the things that I’ve learned is that they will come down on the price of a room because they know that you’re going to be using the AV or you’re going to be buying food from them. And that’s where they’re really making their money. So. So do you use that? Leverage that. And if you’re going to be doing all your meals there, leverage that.

But I would say about twenty five hundred is probably the number that I’m seeing this year in particular.

And I’ve seen a fluctuate over the years went up after Covid.

And now I think it’s starting to come down a little bit.

But I think that that’s probably safe.

Nice.

So what should the agenda look like? And we can talk about in- person and remote events somewhat separately.

Yeah. Yeah. So I like, you know, I kind of think of it, it’s going to take a week, right, of the revenue generations teams, you know, being kind of like off the clock, if you will, or off the floor.

I’ll call it off the floor because they’re on the clock.

But so when I say a week, it’s probably Monday would be the travel day.

Right.

If people are coming from outside of the of the area and if the people that aren’t traveling, it’s their day to kind of get stuff done before they’re going to be off the floor for a few days. And then I like I like a Tuesday afternoon, full day, Wednesday, Thursday event. And then Friday becomes the the travel day again for a remote. I would say that would be a little bit different because you can’t it doesn’t equate equally like an eight hour day in a conference room and an hour a day on on a Zoom is a very, very different day.

And there’s just so much that the brain could handle. You also very often have to take into account different time zones.

And you’re also not in control of what’s happening in each person’s individual home versus if you’re in the room with them.

And so for that, I would say break up to smaller sessions throughout the throughout the week.

You don’t have travel.

Right.

So you don’t have to worry about that. But I would do maybe a four hour.

You could do the same amount of content, but four hour blocks middle of the day. So it accommodates most time zones. It becomes challenging if you also have APAC in there. But you might see you might end up doing doing two events because there’s no time zone that will accommodate, you know, India and Europe.

It just doesn’t work. So break that up. But you’re ending up taking the week as well.

But you’re you’re making shorter days of kind of buckets. Keep in mind break times and especially if it’s remote. But, you know, what is what are what are people going to is going to be breakfast time in, you know, in California and dinnertime in London. Let’s account for that and let’s acknowledge that. But I would say you’re basically looking at a week in general overall and kind of breaking it up that way, as I have found to be the winners for both the in- person or the remote.

Nice.

And we’ll get into more of the into where the agenda specifics. But before we do, how far in advance do you need to start planning this? Yeah.

So to me, I mean, I said this to me. This is like the opportunity for enablement to shine. And if anyone’s going to shine, they’re going to put in the effort.

I think of Q4 is where the enablement team is working on kickoff.

And the thing to keep in mind here is whether you’re a team of one or a team of a million, you’re not doing this alone.

It’s not just the enablement team making this effort.

You need other people in the organization, the subject matter experts, the revenue leadership to be involved. Now, you have to keep in mind, too, that Q4 is their busiest season for the revenue generation leaders or your revenue generating teams. So if you and towards the end of Q4, they’re gone and they should be right. They are pushing the close of the year and that’s their job and that’s why they were hired and that’s why they’re here.

But you need them, right? So if you start early in the quarter, when it’s not as cutthroat for them, and tell them this, like, I know we’re talking about something three months out, but you’re gonna want kickoff the first week, very often they want it like January 6th or February 8th, whenever your fiscal is, well, then I need you now in October and November to let’s set the agenda, let’s work on what you’re gonna be talking about, let’s get you ready, so that I don’t have to bother you in December, right?

Or at the very end of your Q4, and then we’re then being able to work through logistics and make sure we’re fine tuning and the decks are right and doing all the things that enablement does. And I also am a very firm believer that enablement should really leave the revenue generation teams alone, if you will, during Q4, so we’re behind the scenes getting ready for Q1, so we could come out with a bang.

So I like to start, depending on how your quarter lays out, month one of Q4 is when we’re starting to really talk about it, having our, getting any of the input from an alignment with the other stakeholders, and then we could go out and obviously it intensifies as you get later, but your cooperation with some of the very key stakeholders is gonna start dwindling too, so manage that, right?

And so I think if you can make that your biggest initiative for Q4, you’ll see success, and you’ll be able to come out with a bang and everything looks perfect and ready to go the beginning of the first or second week of your Q1. And so we had a couple of questions around who should be invited. So is that just revenue- facing roles who go to the kickoff, like sales, marketing? Does marketing go? Does customer success go?

Yeah, that’s a really great question, and I think it depends on what is the objective of this event, and that’s why we talked about it.

It’s kind of evolved from the sales kickoff, which traditionally back in the day was only the sales team and some speakers from other teams, but I am a firm believer in having, especially if you’re doing a go- to- market kickoff or a revenue kickoff, many organizations say are inviting marketing, sales, obviously, and sales can include SDRs, BDRs, obviously AEs, sales engineers, consultants, whatever we call them, SEs, and then customer success, yeah, if you’re looking at the customer journey and the go- to- market journey, customer success should be there too.

That said, if you’re going to have them there, again, they’re your revenue generation employees, it has to be worth it for them. So really, and we’ll talk a little bit about the agenda, really challenge yourself to make sure that it’s worth it for them to be there, right? Why should, what are they getting out of being here? Why am I taking them away from their day job? One role, for example, that’s really challenging to get there is the support team, right? Because you still have the SLAs to your customers.

So are we having the support team there for the whole thing, or are we bringing them in for some, or are we doing something separate for them? What do they need to? But very often I see the entire go- to- market organization there. And then outside of the go- to- market organization, who would benefit from being there? It’s always good to have people, not necessarily everybody, people from product might make sense to be there, or they might come in for- Yeah, what’s the next question? They might come in as a subject matter expert.

So for example, if you’re kicking off, very often you’re kicking off a new initiative, and the new initiative might be around the new product launch, right? Yeah, have the people from product there. What I have found over the years is that anyone that comes who’s outside of the revenue organization, and if they’re not your learning audience, you don’t have to necessarily think about, what are they getting out of it?

If they’re a part of your learning audience, and what I mean by that is like, if they’re part of your, if you’re making them sit there for the entire thing as the one benefiting from it, it has to benefit them. But if let’s say you’re inviting someone from product because they’re a product expert, you don’t have to worry that they’re gonna come out with the objective.

But what I have found is that they start having a much greater appreciation for what happens on the selling and customer side of the house, which they don’t normally get, which makes them better product people. So often you might invite them and say, hey, listen, we’re putting on the sales kickoff, we’re covering how we do discovery with our customers. We actually think it might be beneficial for the product team to hear that. And the product leader might then send people there. So that’s where I think they really start to understand what’s happening.

The product doesn’t just sell themselves. What is the customer really asking for? Things like that. And it kind of gives them a better, they were able to do their job better, right? And they might not be there for the entire thing. You might invite them for special, for certain parts of the agenda, or they might not travel, but they might like zoom into it, right? But having that understanding, and I’ve only found that they just have a much better understanding of the go- to- market organization in general and able to do their jobs better.

There.

This is a fair question.

Are people still calling it an S K O? Am I a little bit behind? What’s the mix of names that you’re seeing right now?

Revenue kickoff is probably the revenue kickoff. Go to market kickoff, just kickoff. Some people do a company kickoff, by the way, and so we’re talking specifically about revenue and go to market, and you might ask the question why? Why for the revenue teams and not other teams? Revenue teams have a much more- challenging job in the sense of the roller coaster of it right- and so, and Q4 tends to be much more strenuous for the revenue generating teams, whereas other teams it’s just kind of stay steady throughout the year.

And I’m not here to say that other people, other teams don’t have. You know, if you can have a product launch, your product team’s going to feel it before the product launch, but it’s not the same- high risk, high reward- and there’s much more skills needed- is a lot more that you have to go over with. With the revenue customer facing teams- I we can even call them so I see- customer kickoff a lot now, right, anyone who is interacting with the customer.

But yeah, at ESCO or SKO has kind of been going that way- and revenue kickoff, customer kickoff or just kickoff- awesome, okay.

So let’s get back into what are some best practices for content. And again, I have SKO in here. We can replace it.

People know it as SKO, but yeah- if you’re inviting other teams, do not call it SKO, because right, right away they tell- and when I say other teams, you’re inviting other teams to be the learning audience- then then don’t call it SKO, because right away you’re telling them it’s not really for you.

But you’re here where, if you call it, you know, go to market kickoff or revenue kickoff- but if you’re only doing a sales team- and one of the events that I’m working on right now, it’s just the sales team and we’re calling it SKO because that’s what it is right-. So what? Okay, what? What should be in your, in your SKO? Yeah, so obviously really important I kind of think of when I look at SKO, there’s kind of buckets of things that we’re trying to do right, where we might have something that we we really have like doing.

We’re launching this new initiative and we really want to make sure that we’re training. That’s a training element of the team, whether it’s a skill training or product training or process training. That’s the training element. We also want to have the look back and look forward and set kind of set the tone for the year and kick off the year. There should be some celebration. Right, people have worked really hard and celebrating wins at a kickoff doesn’t always have to be the biggest deal.

Of course, celebrate that, but what are some of the wins that that might not always get recognized, that you could recognize here? So, for example, one of my clients last year we had rolled out for them a new way to do their demos and we used kickoff to recognize reps that really embrace that right and to come up and talk about that. That’s celebrating wins and showing people. Oh, okay, if I, you know, implemented that as well, I will, I will do well.

Team building, really, really important, especially if you’re remote normally and you don’t have an opportunity to build together. And, by the way, if you do a remote event, you could do a team building as well. And and then fun for the sake of fun. Right, you could do fun in your event, in the learning part of it, but also if you could, fun for the sake of fun. So what I try to do is I, if I understand the objectives and I have those different buckets.

I look at the agenda and I and then I kind of bucket them in those different buckets and see: are we hitting all these buckets and have we got in the a good balance? Balance is important word and some things are going to be more important than others, of course, but I also know that because I talked to the stakeholders about it. But what is the most important thing?

After, for example, after covid, when people were were stuck at home for many, many years, we had some customers that said we’re just having fun, like there’s nothing else but fun, because we haven’t done this fun together in a long time. That was the most important thing of the event. Usually that’s 30% of the event. Then it was 80% of the right. So really, look at your different buckets and and and make sure that you’re hitting all those things.

The one thing that I will say that the mistake that I think people make is they try to do too much of the focus part. You’re not going to roll out 14 initiatives because we have 14 initiatives. You have zero like priorities, right, but you’ll pick one or two and focus on that for that part of it and then balance out the fun. But also remember it’s a kick off so you can say we’re going to also be introducing this year this next initiative, but this is the foundation for it. But I really try to have that balance of the different, the different topics.

And then I’ll say it again because I think it’s so important, if you’re inviting other teams outside of sales, it has to be worth our time. So make sure that that in there it’s, it’s worth our time being there.

And so you mentioned 30% fun, usually. What are the rough allocations of the other buckets?

When I say fun, 30% fun, you can have fun the entire time.

But I mean, it’s like going out and like drinking, or going to the laser tag, or whatever the heck you’re going to do.

Right, so what was the question? I mean, somebody asked about balance of collaborative sessions, information sessions. I guess these don’t have to be your buckets. But across your buckets, what percentage- ish would you allocate?

Yeah, and that’s a good question. And I would encourage you to ask yourself, what is the ultimate goal? Like, why are we doing this? And that bucket should be the bucket that’s the fullest.

So if we say, the reason why we’re doing this is because we want that by the end of this week, everybody comes out, and they’re really able to demo the new product without any questions.

Well, then that’s going to be the biggest focus.

And that might be where I put 60% to 70% of the energy.

Or if they say, like post- COVID, I just want my team to have fun and let loose, well, then that becomes that, right?

So it’s really asking yourself. And the executives or the stakeholders, what is the balance?

That said, I think that the interactive part of it, I don’t like talk- at- you sessions. There are going to be a few talk- at- you sessions. You need that, right? You’ll have the CEO come in and talk about what conversations they’ve been having with the board or whatever. That’s probably going to be a talk- at- you session, although you could do it as a fireside chat to make it more important.

But I don’t think you should have people in a room all day, and you’re just talking at them.

As interactive as you can make the actual learning sessions or even the customer sessions, I really, really challenge you to do that.

And that could be fun, too, by the way. But there’s always the element of fun.

So if we were to say talk- at- you sessions, interactive sessions, and sessions where there is no learning agenda at all, what would be the breakdown of those?

I knew nothing else, and I’m just going by standard. I would say probably talk- at- you sessions, 10%, just because you have to have some of them, 10% to 15%.

If I could avoid it, I would avoid it completely if I could.

The interactive sessions of the content stuff, I would probably say 60%, 50% to 60%.

And then kind of fun for the sake of fun could be the remainder of that.

That’s really helpful. This was an interesting one. Oops, sorry, we just did that one. I really thought this question was interesting. What agenda ideas if it’s been a tough year, if you didn’t hit your goal, or there were layoffs, or for whatever reason, it was a rough year?

Yeah, that’s a great question, because it’s been the reality. And sales is always tough, and it’s been tough. And know that your sales teams or your revenue generation teams worked really, really hard. I think revenue generating people, sales people, we’re not stupid. We know it’s been hard. Acknowledge that. Let’s talk about that. Use it to start a new page, a new chapter.

But also, how are we going to work with the reality of what is going into the future? Like, are we changing our position in the market? What have we done?

And to acknowledge that this is tough, but also to make it workable going forward. And spend time on that. Maybe if you could look back and find an area, maybe there was a skill. Skills are different today. And I keep talking about COVID, but it was such a momentous time in tech in particular. So for many years, for tech, we were taking orders.

We’re not taking orders anymore.

So if it’s been tough, maybe they forgot how to do a certain skill. Focus on that skill and tell them that. We know it’s been tough. And we know that now, if you perfect your discovery skills and your objection handling skills, you’ll be better.

So that’s what we’re doing today, or that’s what we’re doing this week.

And then celebrate wins that might not appear. The win doesn’t have to just be we hit our quota. It could be we got our biggest client, or we had a big save. Someone was going to leave us, and they didn’t. Or some things that happen, there’s always wins. Find those wins. Recognize the wins. And recognize people that might not always get recognized.

Because when someone’s in a slump in sales, and I don’t care if you’re selling pre- sale or post- sale, you’re selling, if you’re customer- facing, you’re selling, the fastest way to get them out of the slump is to inject confidence back into them. So use that as an opportunity to show them, you’re actually really good at this, and let’s celebrate that and move it on. And make it fun for them to know that you’re with them, but maybe they could learn it in a fun way. But don’t lie to them. Don’t tell them everything’s been great.

No, they know it’s not true, and they’re going to shut off.

Any examples of collaborative learning segments that you really love?

Yeah, so collaborative learning session.

We say collaborative learning sessions where you think they could learn together.

Not talking about you.

Yeah, yeah. I mean, this is what makes kickoff fun for me and where I like to really do it. I think where I really get excited, and I always challenge myself to make it as fun as possible. So one of them, I’m thinking about one of the most successful kickoffs that we ever did. The initiative was account management. And we wanted the collaboration across all the different roles in the customer journey. So what we did is we set it up as if they were all CEOs of their own startup.

And they got to choose their startup name. They got to choose their startup mission. And then each person in the group was given a role in the startup.

And we called it like off of like a Y Combinator kind of a breakup. We used the name of the company, but slash Combinator, right? Yeah, yeah.

And it became a competition.

By the way, revenue people love competitions or competitive people.

And so what they were doing was they were going to have to do all the steps of the account management to then make their pitch to the, to the, you know, the, this Y Combinator like board group. And then that one of the companies was going to win a, you know, the, the funding or whatever.

They created websites. It was, it was four day and they got so into it.

It was, it was unbelievable.

They learned a tremendous amount.

It was incredibly engaging.

And, and, and, and we watched to see how it impacted how they interacted after they left kickoff, right?

Because now they had a really good understanding of like, Oh, I really need to do the research on the company. I really need to present it right. I really need to work on my presentation skills.

And I would say in that kickoff, we might’ve had 15%, 10% of talk at you.

We invited people that they really want to impress like someone from their board was there. So, and it became really, really fun.

I know budgets are a good question.

What I learned in that example as well as like we had a prize money, but they didn’t care about the prize money, not, they cared about the bragging rights that they got and the little metal that we gave them at the end that we spend on Amazon 10 cents or 20 cents each. Um, it was incredibly interactive, great learning experience. And the biggest feedback that we got was that they, that the different roles had a much better understanding of what the other roles did, which changed the way they engaged with each other throughout.

Like for example, I remember someone from marketing coming over to me and saying, I now get why, what I, what comes through the demand gen really matters to the SDR and the AE. Yeah. That was worth your wait.

Right.

Fantastic. Uh, so there are a couple of questions. I, I don’t have one of these queued up on the slides and that was my bad is how do we, how do we make sure that things are reinforced after the SKO is over?

Yeah, really, really good question and really, really important and something that I think a lot of people drop. And I think that the enablement team or whoever’s reading this effort should really figure that into the plan. Um, first of all, record all your sessions live or, or virtual record everything, and then break them up into, I call them micro learnings afterwards, um, and use that as refreshers throughout the year. First of all, get it into your onboarding, right?

Cause people that haven’t been, who weren’t physically part of the company yet and haven’t been there, they should know if it was a key initiative for the year that it should be included in their, in their learning path. But one of the things that I really think about is in enablement, the analogy that I like to use a lot is like you have a balloon, you popped it up and kickoff is a really big pop up, right?

But then it’s going to start falling back down and how do I pop it back up again?

And that’s where you kind of break it into like little micro, um, uh, learnings, whether it’s the videos or whether it’s followups on in your knowledge management or whatever it is, but then release it throughout the year as a, Hey, reminder, like this was something that we, that we covered.

Um, so if I use my example from that account, that Y Combinator thing that we did, the biggest learnings, we would send it out every few months just to remind them that, that, that they’re actually, um, that if they do this thing actually would help them to move this, this account forward.

Um, and then also end the kickoff, and I think this is really important and kickoff by saying this was the kickoff and this is how we’re going to continue to support these initiatives throughout the year, tell them that. And then the next quarter, when you do your quarterly business review or whatever it is, go back to a kickoff. We did this and now we’re moving that. So show them that journey. Don’t just come in and do it once and walk out.

It’s not a once and done. It shouldn’t be a once and done.

It should be the year I might shift throughout the year, but it should be throughout the year.

Um, and, and, and reinforce it.

And also, uh, lastly, I’ll say, make sure your frontline leaders are enabled to keep advancing it and reinforcing it throughout the year because enablement is the, is the, uh, uh, few to many, whereas the frontline leader is the one to few, right? And so they, if they’re, but if they’re not enabled to support the initiatives, then it’s going to go to die. What about, uh, other events that you have throughout the year, mid- year kickoffs or quarterly business reviews? How does this stuff get echoed through those? Yeah.

So really, and I thought about this and I, just a second ago, right? So mid- year kickoff tends to be an injection second half of the year. It’s usually a little bit more, not as big of a production as SKL. Sometimes people will do it as regional events and have the, the, the event team travel rather than the, uh, the other team travel obviously for costs or maybe it’s remote or it’s only one day, but it’s a way to either pivot if you needed to pivot, right?

Because a lot of times halfway through the year, we’re like, well, is it going the way we thought it was going to go or just kind of re- inject a little bit into to get the second half of the year done.

Um, and, um, that were usually a one or two day event. Um, and quarterly business reviews are, are on a quarterly, uh, um, uh, cycle. They, they, they’re, they’re shorter. There are sometimes aligned with the QBRs at the, that the revenue leadership is doing anyway, but you’re coming in and you’re having a part of the, let’s say, uh, a, um, a learning function of it.

And it’s, it’s making sure that you’re continuing that agenda throughout.

Um, and sometimes it’s, there’s, they’ll, they’ll do their quarterly reviews of their accounts, but also have like a second day of just kind of like enablement led day or enablement partnership day.

And I assume quarterly business reviews much more likely to be virtual?

Yeah, depending on the company, if you’re an in- house company these days and everybody’s in there, you might bring them into the conference room. But yeah, quarterly business reviews probably will be remote. And mid- year might be remote, might be in person, or very often the event team or the enable team will travel to the conference.

Oh, that makes sense.

And do like a road show. So that instead of having everybody come from like Europe to the U. S., we go to Europe and two people are traveling instead of 50 people are traveling or whatever.

Of course, yeah. Really good question. How can enablement show ROI from an SEO? Yeah, really good question.

So what is the initiative, right? What are we trying? And some things are gonna be harder, like you can’t necessarily show ROI of what the fund did, although we know that people need to celebrate and have fun a little bit. But from the main initiative of the event, whatever that was, whatever the focus part of it was, and just like any other enablement thing that you do, what are the indicators that are gonna show that it’s moving the needle? So for example, if you’re rolling out a new product, well, how much is this product showing up in pipeline?

How much is it, how quickly or how fast is the specific product line moving through the funnel? How much revenue has this product generated for the team? Now, you can say there were other factors that contributed, sure. But if it’s been a day and a half trying to demo it or pitch it, well, you could then say, well, it’s having its benefits.

So whatever that initiative is, in the example that I gave with the Y Combinator, what we were tracking to see was collaborative effort and account planning for their top tier accounts and each rep, whatever segment they were in had their top tier accounts. And how many of those top tier accounts are now, is there, where’s their business expanding? And that was the ROI that we were able to show because that’s what we were tracking because that was the objective of the event.

So acknowledge that, make sure that you know what that is, make sure that your leaders, your other leaders, stakeholders know what that is. And then you can point to it and show that it was worth the effort.

Nice.

So switching back into some of the sources of SKO content, you mentioned some good ideas. This is actually pulling from the chapter in your book, but do you want to talk through these and other sources of content that you find are really effective?

Yeah, absolutely. I’m sorry if there’s a car blinking out of my window. I’m sorry if that’s overwhelming. Yeah, so I think, again, customer perspective, having people talk, customers hear, the go- to- market teams hear from the customers is incredibly valuable. It’s usually one of the highest rated events of the day. I really like, and again, you could do it in creative ways. I like asking questions that you probably wouldn’t ask for like a case study.

So for example, what was it like, and it has to be the right customer, but what was it like to go through the sales process with us?

What did you like?

What did you not like? Why did you choose us and not the competitor? Who else were you talking to? What did we say that made you stay with us? To really help the revenue generating team understand some of the things that they wouldn’t necessarily really be able to ask, that’s one thing.

Another way that you can do it and make it really interactive is I like to, you could do like a fireside chat and have a panel or have a bunch of people talking, but then also maybe break up the group and allow the group to then have direct questions with this customer, ask them questions and get to know them on a personal level. One year when I was at Optimize Lee, we wanted the fund for sake of fun because we want them to start seeing them as humans and we put them all on a golf course together.

Go out and be on the golf course and the conversations that they did on their own automatically was really interesting, right? And the information that they got because they became human to each other and then naturally they started talking about it. Have maybe the customer that is your persona maybe come be the person that you talked to, not necessarily just the person that you sold to. So really, really important.

Wins and losses and look back is so incredibly important and maybe not just the biggest win that everybody’s always talking about, but some of the ones that were probably the most challenging that we overcame. People are always afraid to put the losses up. I think you get the most out of it. I have a very interactive, like a speed dating style event that I do for wins and losses, which has each person have an opportunity to pick their biggest win and their biggest loss.

And then they share it with a bunch of people in like a speed dating kind of a event.

That’s a cool way to make it interactive.

Exactly. And it’s fun and everybody gets to share a win and everybody gets to share a loss, right? And often, and in the win, what went wrong too, right? And in the loss, what went well? Because there’s always something, right? If it’s worth talking about. And if you’re gonna do just highlight a win, one win and one loss or a few. Now that I’m saying about, sometimes what I’ve done is you have the win and then the customer come to the customer panel.

So they, so, and the customer is not necessarily in the room for the win part of it, where you can kind of break down the deal, but then you come here from the customer. So you kind of continue the story, which could be really interesting. Don’t have the customer in the room for things that we don’t want the customer to know, but bring them in afterwards. Not know, but hear.

Year.

And then I had another thought and it’s out of my head: so if you’re only doing one like, if you’re only highlighting one prick a rap, that that it’s okay that they could talk about their loss, that they’re it’s not that they’ve had a pretty good year or a decent enough year that they feel confident to be able to get up and and be honest about what happened. And then when do you use outside speakers? Good, yeah, that’s a good question, and there are pros and cons to outside speakers, like anything else.

When I would use an outside speaker is a to validate some things that we’ve been saying internally, because sometimes if you hear it from an outsider, it like an outside sales coach or like who are the types of it could be an outside sales coach. You could be an outside expert in the field, like, for example, AI is the biggest thing right now. Maybe come, have some, come in who’s you know talks about.

If, let’s say, your company’s big shift is to a specific type of you know AI initiative, well then, have someone come and talk about the benefits of that, or that’s just an example, but it could validate some. Or it could be a sales coach- right, it could validate who some of the things that you’ve been saying internally.

The other thing too, that the other reason I really like using outside speaker is if, let’s say, we take a three day event, by day three, everybody’s tired, most people are hungover, bringing someone from the outside, they can inject energy back into it because they haven’t been at this event for three days. But tell them that, like I’ll always say, like we’re bringing you in your day three. We had a big party last night. We let people go lose. The team is a little hung. You know teams are gonna have a headache.

Come in and know that and they can, you know, inject that energy back in. Sometimes you might be someone from your board or it might be somebody that that that that people really emulate and it could really add a lot of, it could really inject a lot. It’s also very, very often very expensive and it might not be worth it and I, if you know, if budgets constraints are there, don’t don’t bother with it.

But so way that, way, way the pros and cons, but that’s kind of how I like to use it, mainly for for the energy, because even like I am very big believer that that, that the that event team should, should not be hung over during the event, because I can tell you power stories of why we messed up our event when we were. But you’re still tired. Right, it’s day three, you’re still tired, and so having someone come in from the outside who’s not can really add a lot of energy, if it’s the right thing, to the event. So this, this dovetails your.

How do you save money? Maybe the outside speaker, something you cut? What are other things you can cut if you’ve got real budget constraints, yeah? So again, look at what’s what’s the what’s the most important thing for the event and spend your money there and then see where you can cut. So, for example, I often will go cheap on the meals but spend more on others, like the hotel should be nicer, but we’re going to go with the cheapest option of the food is going to be fed. I was gonna be hungry.

It might not be, but it’s not going to be the highest cost meal. The only time I’ll spend a lot on the meal is the day after the big party the next morning, because they need it. So you know that morning you’ll have a fancier breakfast, but go with the. Go with the fancy food and you know what when you get, when you get the feedback at the end of the event, they’re going to tell you the food wasn’t good, but you knew that right. Again, I’m not saying get crappy food, but I’m saying don’t. They don’t. The catering company is going to give you options.

Go with the lower end because, again, that’s not what the point of the event is, unless it is right. I was just talking to one of the events that I’m working on and the most important thing was there they have a lot of female travelers. They want their team to feel safe. The hotel that we’re in is incredibly important. We are spending more on the hotel and we will spend less on outside the events that we do. Right, because we know that that’s the most important thing, right.

So, again, understand where you’re, where you’re, what the priorities are, and then adjust accordingly. Also, one of the tips that you might want to use is: look within the organization. Is there a DJ in the organization that I don’t have to pay was willing to do it? And in the organization doesn’t just mean a go to market organization. Are they sitting? Do you have somebody who’s really great at creating films? And they create some things for you that you can use as engaging films throughout the event.

And when I was an optimizer, we had this guy who was- he was in the engineering team but he was also a filmmaker- we had to make a bunch of different videos through us and it was kind of like we did this like continuous story throughout the event. It was part of the head of the event and we spent nothing on it. Right, he did it because he wanted to do. It was fun for him. It made tremendous and added tremendous energy for the event out of a lot of fun and we didn’t have to spend any money on it.

So ask the organization, invite them to to, to, to to use their talents. One year we had a guy who was a great comedian. We had him be the entertainment at the party, right, we didn’t have to pay him, right? So look at that. Do you need swag? Can I go with cheaper swag? Do they really want the swag, right? Can we, if we’re giving a prize, does it have to be a cash prize, or could be a bragging right prize?

Or how do you, what’s going to give, get the goal of the event but not cost us a tremendous amount of money and the stuff that’s the most important, for example, the people being safe in a hotel. Yeah, spend a little bit more.

There.

So I don’t know. I hope that answered the question.

But, yeah, another interesting idea. Have you ever seen a partner sponsor? How does that work?

Yes, love that idea. Get them to so, so and it’s. It’s a win- win- win- win- win- win right. So have the partners sponsor the event and maybe they’ll sponsor the alcohol at the event, because that’s a very big cost at an event, depending on on the culture, but it could be so.

But then you have to give them some some air time so you might have them do some sort of a session, but also maybe do like a happy hour with them, or or invite them to your fun event and get the reps to have to interact with them and to you to to interact so they get something out of it. It develops that relationship with the partner and then the partner actually gives you, you know, funds, funds for the event, or or cuts, cuts some of the funds and love it. It could be a vendor, right, who might want to do it too.

Yes, getting creative like that is a great idea and used it, have used it really successfully in that Y Combinator example that I gave you. We actually, for one part of the journey, they had to use the partners and then the partners came in and they sponsored, and then we had a big party with the partners afterwards and, and they took care of this, that that night’s dinner, so that made a tremendous impact as well. And then for SwagTube, I could they give you the swag right and, and, or we even sponsor the swag. Let’s say nice, cool.

So we haven’t yet gotten into some of the logistics- less sexy questions, but interesting questions, important. So, in if you’re doing an in- person SKO, RKO, what are some of the things you have to plan logistics- wise?

Yeah, so I think one of my biggest learnings is: you’re going to have the number of people that are in the room triple. That amount of devices are going to be trying to connect to your Wi- Fi- right, because everybody has a phone, a laptop and that, right, and you’re going to probably also want your so A. You want to be able to make sure that there’s enough Wi- Fi to to accommodate that. And then your own presentations, probably one on your own. Like I like hardwiring those presentations so that that your day runs, runs seamlessly.

Think about how people are, how is the day going to flow, and what do I need as far as microphones, like, do I need some handheld and some lapel ones, and how am I going to break that up throughout the day so that that the day really rolls seamlessly? One of my- this really happened. So if you’re using like a cloud software- let’s say Google, you know, Dex, download them before the event, because we were doing one event, it was the first day of kickoff and we had everything in Google Slides and Google went down.

That was it and we had nothing backed up. Back up everything day of. You can use your, your, the, the cloud one, but have a backup on day of of anything that that needs to be presented: activity guides, facilitated guides, any of those things. So make backups, test that that that microphones work, that sound works, that anything, anything that you’re playing to music you’re you’re going to try to play. Make sure that that works.

I like going, if you’re doing an in- person, doing a tech rehearsal the day before, making sure that every presenter knows their soft, the software is working on their, their, their computer. I actually like one computer for the entire event and have and make sure you have all the software that you need on that event to run anything that’s going to happen throughout the event.

And I’m trying to think of something I think take take into account that there might be bad weather and how that might impact the, the AV and all that kind of stuff, and this is all somebody on the enablement team’s job like this is. This is all very good question, so maybe not right. I I like to bring someone from IT there right, or somebody from the, from the hotel or from the event space, and and again, that could be costly.

So can I have somebody from from from IT there and, especially if you’re doing remote, have have someone on the line that can deal with the technical issues that are going to come up, so that you can focus on the event, even if- and I know that there are some people that have, you know, teams of one and some people that have teams of 100,… are going to help you. So your job at enablement is to make sure that this is going to be taken care of. But no, it doesn’t have to be. I’m not a tech expert, but I know that I have a tech tech expert in the room.

And that could be someone internally that I’m not paying, or it could be somebody from, you know, the event space that I am paying. If you’re doing a remote event, I would not do a remote kickoff with that one.

I’ll call a producer on the line who’s behind the scenes and can deal with the person that can’t hear you or whatever it is, because you have an event to run.

So not necessarily, but be there for the tech rehearsal because you’re the one that knows what it should sound like and know how it’s going to flow and so on. And the last thing I’ll say from logistics too is make sure your catering team knows to line up when to have the food available. Make sure you have water and coffee throughout the day.

These are things that could really make or break your event.

One time we didn’t have the time lined up the right way. We gave a break. They were still setting up. We ended up, it messed up our entire day because by the time the food was ready, we wanted to start again and people hadn’t had anything to eat. So make sure that that’s also been aligned.

And if you’re doing remote, make sure that you’re taking into account the times that people are going to need to eat based on where they are in the world.

Anything else on a virtual event that you have to think about for logistics virtually?

Yeah, so you can’t use one computer, right? You’re not in control of that. So does everybody have the, know who’s presenting what and when, right?

Make sure you rehearse that or you talk through that.

Can they hear, is that microphone clear? Where are they, right? Are they sitting in a hotel room with crappy wifi or to test that and ask them that. Don’t assume you’ll know.

The other thing that I’m going to say from logistics, and this is whether you’re in person or not, it’s something that I’ve learned post COVID. It’s typically right after the holidays, flu and COVID are rampant. Be prepared for one of your main presenters to wake up sick. And what am I doing as my backup?

Who’s going to step in for them?

Cause it’s just going to happen or it has happened over the last few years.

So have a backup. I like to record rehearsals so that in case somebody wakes up the morning of and says, I have 103, I can’t show up. I can plus record, or I have an understudy.

I have somebody who’s after the rehearsals, who’s ready to go. Know that it’s just a reality and it’s gotten, obviously since COVID got introduced and it’s not just the flu that we’re dealing with or winter cold, have a backup for that.

Awesome. And then, yeah, and like I said earlier for remote, break up the day. Don’t, give a break. You might, you probably might even give more breaks. Like I like to give a shorter break on top of every hour for a remote event. Cause you’re not in control of the room.

So you can’t read the room. You can’t read to see like, oh, I need to give everybody a break.

And you also don’t know what’s going on in their world.

Right?

What’s happening in their environment that they’re in. Is that kid crying? Is he coming home from school?

Right?

So make sure that you’re accounting for that and what time it is for them. You know, how tired are they? Have they eaten? Do they need a break?

Awesome. So we’ll move back into all of the questions that are pre- submitted and coming in. Please feel free to keep adding these into the chat. We had a question about role- playing. Do you often see role- playing? And if so, how do you execute it well?

Yeah. I mean, role- players, it could be a great, a great opportunity to role- play.

It could be a great opportunity to role- play with different roles. If you have different roles in the room, so they can really get the, the understanding of some of the different roles. The way you kind of do it really well is have really good scenarios that they can work through and give a good enough backstory.

And I like the story to continue, if you will.

Right?

So if we’re taking them through the customer journey, they’re staying with, this is the company. We pick a company, we pick a case study, and you may have a different company or a different case study or scenario for different segments, for example, or different product lines, but like have them come through the journey.

Role- play type of a competition could be really fun.

Right?

If you have, let’s say a pitch competition and they’re role- playing with leaders or role- playing with people that, and here’s where I like to also bring in people from, like let the people from product play the customer.

Right? Know enough about the product that should know enough about the buyer. And now they’re also seeing the other side of the equation, but make sure that you’re also giving enough context to the person role- playing. Give them a backstory. And one of the things that I like to talk about the role- play is, don’t be the nicest customer in the world and don’t be the worst customer in the world. Because the reality is, we think that they’re one or the other.

They’re not, they’re somewhere in the middle. So kind of give them guidelines of how to do that and give them a rubric. But yeah, it could be a really great opportunity to get some role- play.

You might even, I don’t know, create, take an AI agent and have them be the, and have people go to different stations and interact with different stations.

If you could bring in some sort of an agent like that.

We actually even sometimes will bring in people from the event staff to play the other side.

Give them enough information. So yeah, that could be a really great time, great use of time and energy.

Cool, we touched on this briefly, but I’d love to dive in a little bit deeper for those little teams. So if you’ve got one enablement person, maybe less than 10 sellers, what do those smaller kickoffs look like?

Yeah, so they’re probably going to be shorter, they may be a day, right, or a day and a half. It might be remote, right?

If you are one person doesn’t mean that you can’t leverage other resources within the organization to support you, right? Because you’re not going to do this alone anyway. Is there someone in product marketing? Is there someone in product? Is there somebody who loves putting on events and that’s what they do and they can take care of kind of logistics? Can I partner with the office manager to do some of the logistics around where we’re going to do it and how we’re going to do it? But it’s probably going to be a shorter, a smaller event.

The buckets stay the same probably and the percentages in the bucket stay the same, but you might not be doing as much. And also don’t forget the tribal knowledge within the team itself. When working with a team, they don’t even have an enablement team, so we’re running the event for them. And so we put together a sales kickoff committee of members of the go- to- market team who are serving as our partners.

They’re helping us to find locations because they know the area, they’re giving a sense of what’s really needed for the team during this event, and they’re having fun doing it. We have to balance the fact that it’s Q4 and their job is also to close business, but they’re part of the SKO team and we gave them a leadership role in it, and so it’s expanding our team. But it all goes back to what are we trying to accomplish? Why are we investing in this time and how much time do we need to be able to do that right?

And yeah, maybe it’s a day or day and a half event and that could be incredibly impactful for a team of 10. And are you a team of 10 that usually sits together or a team of 10 that’s all over the world? Again, that’s going to be another consideration to think about. But leverage your partners. I think of enablement as a bridge, and we’re a bridge to the go- to- market team, but we’re a bridge from product, we’re a bridge from operations, we’re a bridge from PMM, so use that bridge and you are the connector to facilitate this event.

This question is about annual planning for the company, which probably has already happened by the time you have the SKO, but how do they go together?

It should have happened, and the SKO should be based on the top initiatives that were planned for the OKRs, and it might kick off what other teams know to be their OKRs now for the rest of the year.

So if you have two or three main initiatives, kickoff will probably hit on those main initiatives as what you’re focusing on in the agenda, and it’s where the go- to- market team start understanding, okay, so this is our map for this year based on that.

And you might start the event where chief ex- officer comes in and says, these are OKRs, and we’re now going to spend the next day, really, because of these OKRs, we’re going to spend the next two days or whatever digging into this path down through the OKR. And then after that, where it continues, the reps could all go make their own OKRs, because they now have an understanding of the direction of the company for the year. Cool.

And then potentially a last question, is AI going to change SKOs or enablement more broadly? I guess, how do you see AI changing the way that enablement enables revenue teams?

So the answer is yes. AI is changing everything, but I think it’s going to enhance. I’m very excited about it.

There are things that I’m concerned about as well.

But how do I leverage AI to multiply us, right?

And how do we leverage AI to continue to up- level the skills of the reps? I’ve been spending a lot of time thinking about AI in general, and thinking of it as a spotter rather than, it’s like if I’m weightlifting, I’m still lifting the weight, but maybe it’s a spotter that actually helps me.

But how can I get, how can I bring that into maybe the fun of the event, right? Like I said earlier, could you have an AI agent that plays the customer?

Can I program it with all the things that I want the customer to say and do and know, and then have them kind of do the role play and give the exchange?

And how can I use it in the fun of the event?

I’m a big believer, if you could, if you have the budget for it or whatever, to have an app for the event and really create that excitement throughout, and how’s AI going to kind of play into that a little bit? So AI is going to change everything, and I’m here for it, for the good parts, and I’m going to try to figure out how we’re going to work out. I could probably do a whole hour on that for SKO, for enablement.

But yes, I mean, AI is here, and there’s going to be pros and cons like anything else.

Awesome.

Well, thank you, everyone, for joining. This recording will be available. We’ll send it out to all of the registrants after the event. And if you want to contact Roz, either for SKO- related questions or facilitation or broader enablement support, we’ll include her contact information as well.

I want to make a quick plug. We have a book on enablement that’s hitting the… you can purchase it on Monday.

Nice.

It’s called Accelerating Revenue.

It’s a guide to enablement. So if you are interested in that, check it out.

You can look on our website. We’ll have the link to it next week, but we’re all excited about that.

Yes, we’ll link to it in the takeaways as well. Perfect.

All right.

Thank you, Roz. Have a great weekend. Thanks, everybody.