How to communicate major product changes to your users

This week, we talk about two of the main things to consider when communicating upcoming product changes to your users: how tell a story to generate excitement, and how to make sure that your change-averse users don't get angry and leave.

Show Notes

In this episode, Rick helps Tyler think through how to roll out a major product redesign for his 20,000 users. Tyler has a plan, but he’s concerned about losing customers through the transition. His biggest roadblock is figuring out how to roll this out without causing his customers to get angry and leave.

After going back and forth, the following framework emerged for communicating major product changes to existing users:

• Why you are making the product changes in the first place?
• How will you measure success (i.e. the desired outcome)? 
• What are the key messages you need users to understand?
• What proof points (e.g. screenshots, quotes, stats, etc.) can you provide that your key messages are true?
• How can you segment users and prioritize them?
• What mediums should you use to communicate?
• How often and over what time period can you communicate these key messages and proof points to each segment?

Takeaways include: 

• Start with why. Identify why you are doing this. Is it for customer acquisition, customer retention, or something else?
• Recognize that some users will go through change cycles, and help them through it. This starts with clear messaging.
• Don’t surprise your users. Give them plenty of notice and time to get through the change cycle.
• Treat this like a marketing funnel or sales pipeline. It’s a conversion.
• Segment customers by risk and value so you can prioritize outreach. This might be based on revenue, net promoter score (NPS), product usage or a new survey.
• Choose mediums and frequencies that support your annual contract value (ACV). If you are a low-ACV product, you probably can’t afford 1:1 phone calls for every customer. 

The change cycle concept

Source: changecycle.com

What’s the product change?

Tyler: The topic for this week is how to communicate major product changes to your users. This could go any number of directions, but the reason I'm bringing this up is, I've referenced the last few episodes where we're working on this big redesign of Less Annoying CRM. It's both a redesign and two major new features. It’s the biggest update we've had in at least five plus years, if not ever.

Rick: Did you say two new features?

Tyler: Two new features. Yeah, outlook, calendar sync. And we're completely redoing custom fields. Pretty big features, but the thing people will notice most is the redesign. And so I've been kind of thinking, "how do we communicate this to people?" The traditional way to think of this is, "how do you build hype and use it as a marketing event?", which we can talk about. But the theme of the podcast is "how do you build a business to last?" And I think a lot of companies change and eventually it leads to their downfall if they do this wrong. They forget their core audience and all that. They get too excited about the upside. Our audience is not one that loves change. And so most of the communication side that I'm thinking of is not, "how do we market this?", but instead, "how do we reveal this to people in a way that will minimize their likelihood of flipping out and leaving." Basically.

Rick: In other words, a lot of companies might see this as an opportunity to wow users. You don't see that. You see this as a threat to users.

Why you are making the product changes in the first place?

Tyler: I think it's good for them, but if I'm being totally honest, the reason we have to do this, is to keep getting new users. The two new features will be helpful to our existing users. The redesign won't. They already know how it works. It'll look nicer, but that doesn't provide any value to them and they're not going to be excited about the fact that we redesigned.

Rick: Is this true in most cases? When companies do redesigns, is it always usually for new users?

Tyler: Yeah, I think so. I was just kind of thinking of this case, but if your audience is really into design or something like that, maybe they get excited about it. But for the most part, if you think of software as a tool, which CRM software certainly is. I think most B2B software is a tool. Once you know how the tool works, I can't imagine much benefit to saying, "okay, now you have to learn a new way for it to work."

Rick: If it works currently?

Tyler: Yeah. Yeah, true.

Rick: Got it. Yeah. Okay. Man, I guess, if the redesign is valuable to new users, there's got to be some benefit to switching to the new design for old users.

Tyler: Yes. And so a couple things on that. First of all, this is one reason why we're bundling it with two new features. We've done this throughout our history. You know how anytime Facebook changes anything? Everyone on Facebook's like, "oh, I hate it, I'm quitting." And then they forget about it a couple of weeks later. One way we try to minimize that reaction is saying, "there's an actual new feature for you here that you care about." And probably it doesn't have to come with the redesign, but to a user, it seems like they're a package deal.

Rick: Yeah. I'm also realizing that your users are probably highly sensitive to this because this is a CRM product. They use it every minute of every hour of every workday.

Tyler: And there's also a history here, which is a lot of our users are older, 40 plus years old and they've been through multiple cycles of CRM companies screwing them over. And so part of this is a lot of them, their natural reaction is, "oh, you're getting ready for an acquisition. You're getting ready to raise prices." They see the writing on the wall anytime anything changes. So I have to kind of reassure them like, "no, no, no. We hadn't redesigned the software in seven years. We need a new design here."

Rick: I think we should dive into why you're doing this. Just because you need to do it for seven years doesn't resonate with me. It probably won't resonate with your users. So why do a redesign? Let's actually exclude the two new features from this conversation.

Tyler: Yeah, I agree.

Rick: Why are you prioritizing a redesign and what does it mean for the company?

Tyler: Okay. Let's break this into two categories. One is just pure first impression. When new people sign up for the product, it looks really old and outdated. Like I said, "I don't think our current users care about that cause they're used to it." But definitely if you go too long without updating your look, I think you lose trust with new users. 'Cause they look at it and they say, "well, why does this look like it's from the previous decade?" I do think there's some marketing element to that. And then there are actual functional problems with our old design. It was designed at a time where people didn't use mobile very often and so it was very hard to make it responsive to a mobile screen. We've added a bunch of features, since this design came about, and it just doesn't work very well with them. There are real practical reasons for it, but that's 50% of it. The other 50% is just, no one trusts us if we look too outdated.

Rick: Okay, so one is the internet is developing more and more of a standard for design and user experience. And if you want to remain trusted, by some segment of your existing users and new users, you need to stay current and meet those standards. The second is we're actually going to make it easier for you to use our software, whether you're an existing user or new user.

Tyler: Mobile is the main driver of that. Right now, we have a separate mobile version from desktop. That gets totally neglected. And the idea is, once this is done, it'll open us up, it won't be completely all the way there. But we're moving in a direction where we just have one app that works on all screens.

Rick: Have you explained that, in the way you just explained it to me, to a user and gotten their reaction?

Tyler: Yeah. I've talked to a handful of users about this. We've written a number of blog posts, also, that really walk through this in detail. I'm trying to over-communicate this.

Rick: I feel like you just gave me maybe a minute, 30 seconds to a minute elevator pitch on this. If you were to tell a user that, what would be their reaction? It seems like they would be like, "thank you for thinking of this."

Tyler: We've talked to a handful of users. We got one very negative reaction and we actually showed them the new design in action.

Rick: Did you explain why first?

Tyler: After the bad one, we started. Yes. I learned my lesson.

Rick: All right and how'd it go after that?

Tyler: Well, let me explain that in case anyone else is going through the same thing. What we did is, we showed it to them and before the person could even see what the changes were, they just immediately were like, "oh no." She was going like, "oh no, it's changing. I hate it. I rely on your software and it's changing." She didn't even see it first.

Rick: You didn't start with why?

Tyler: Well, not in that call, no. If anyone else is ever doing this, start with why, for sure. And that's part of the reason I want to talk about this today, is I need to get this in front of people so many times, I think, before they see it for the first time. So that, A, they understand why and B, even if they are going to disagree with it, I want them to get mad and then get over it before it matters.

How will you measure success?

Rick: Got it. Okay. So that's why you're doing this? What does success look like on the other end of this?

Tyler: Yeah, that's a good question. I mean, the most conservative version is just, "I hope we don't lose our current customers." We're going to lose some, but I hope we don't lose a meaningful number and they're not angry at us and it doesn't hurt churn rate long term or anything like that. Obviously, we're hoping our NPS goes up. We're hoping that growth goes up and stuff like that. But that's secondary to that.

Rick: Isn't the number one reason you're doing this, for new users?

Tyler: Eventually. It doesn't have to happen now for new users. We haven't hit an acute problem with growth or anything. It's just like every company has to at some point I think. So we'll look at NPS and all that and I'm obviously fingers crossed it goes up. But the most immediate thing we'll be measuring is, can users log in the next day and business as usual. I still know how everything works because we tried not to disrupt their workflows or anything like that.

Rick: Yeah. So it sounds like success is customer retention, long term increased promotion by users, NPS. And then third is maintained conversion rates of customer acquisition.

Tyler: Yeah. And hopefully it increases it.

Rick: All right, cool. NPS is in there for a reason and I'm assuming that's more of a marketing metric for you, right? I look at NPS as, "hey, this customer's happy." It's an indicator, not the only indicator, but an indicator that they're going to retain and stay with you. It's also an indicator that they're going to spread the word. Right? And generate you more leads. We talked about conversion rates. NPS is sort of this other thing that says, "hey, maybe you're also focused on generating some leads here."

Tyler: Yes and no. The primary reason I mentioned it is because I view it as a leading indicator rather than a lagging one. Someone churning is the last thing that happens in a long series of them losing faith in us. We don't do pure NPS, we do a one to five scale. But if those rankings, that people give us, start going down, to me, that would be an indicator that there's bad news brewing on the horizon that just hasn't gotten here yet, basically.

Rick: Yup. Okay, cool. Well, I guess I'll just ask you directly then, why are your conversion rates the only focus here? Why isn't expanding the top of the funnel a focus?

Tyler: I guess, first of all, I'm always skeptical that a redesign will do that. I think people get in their heads a lot and say, "oh, I can ..." Well, let me give an example. Throughout the history of the company, we always build new features and we think, "oh, this one feature, that's the one we need. Everything's going to get better after this." And it never happens. All of them added up together over years make a difference. But we have yet to ever launch anything that we can tell really makes a difference on growth. So that's one reason, is just experience with that.

Rick: Got it. So you're looking at this mostly as a conversion rate thing? Not a full blown marketing effort. Okay. I'm going to challenge you here for a second. Do you feel like you're walking away from an opportunity to really increase awareness about Less Annoying CRM through this?

Tyler: I'd love to hear your thoughts on this. I always roll my eyes. I think like a lot of marketing is just bullshit. And when a company gets all excited, "oh, we changed our logo." I don't care. The two new features I could see marketing. What are your thoughts on, does anyone care that we, it's a pretty dramatic redesign, but does anyone care?

Rick: By anyone? What do you mean?

Tyler: Who wasn't already evaluating us? I think it'll affect someone who's evaluating us 'cause they'll say, "oh, this looks modern, it looks updated. This company's probably more legitimate." But someone who wasn't otherwise thinking about us, why would they care that we just launched a redesign?

Rick: Well, this is getting into the kind of gray, I don't wanna call it gray area. It's getting into the space of "you can't really measure it, brand awareness." And I guess one reason all the companies do execute a playbook around a big launch that involves press releases, media, event announcements, really blowing the communication out of the water and hyping it, is because of the brand exposure it provides. And that is of value to the organization.

Tyler: But does it provide brand exposure? If you write a press release, does anyone read it? How do you get this in front of someone where they care?

Rick: With a story. So the question is, well, there isn't a question. You have an interesting story. Every time I tell someone about your business, they go, "that's really cool," right? You have a story and it's a story that resonates with some people and most people, the people that could help you, don't know about your story. You're still small. Right? I assume that you haven't, you're not like at 60% market share, are you?

Tyler: No, I haven't bothered to calculate it, but I assume it's significantly less than 1%

Rick: Okay. So there's a huge market out there for you. If you look at the market in three segments, you've got your customers and former customers, who know you well, right? Or know your past self well if they're a former customer. You've got potential customers who have had some brand interaction, whether it's visiting your website or filling out a lead form or whatever it is, having a brand interaction. Then you've got everyone else who has never even heard of Less Annoying CRM.

Tyler: Right. Which is a much bigger group.

Rick: Yes. We're really talking about communication, helping the people who are really far down in the funnel, with your customer acquisition. Meaning they're playing with the product. And the people who are already using your product. Right? Retaining them. That's such a small percentage of the people who could be interested in your story and you have something that you're doing, that's a big deal. It's a big a deal enough for you to have this podcast, to take time to communicate to your users, and how many users do you have right now?

Tyler: 21,000.

Rick: 21,000 users. You have something here. There's a story here that maybe a lot of people out there would benefit from hearing right now and appreciate being told. And I don't know what that story is per se, but I'd be willing to bet some money that there's a story here.

Tyler: Yeah. I buy the overlying premise of this. Although, all the content marketing I've ever tried to do has hit a bit of a wall with basically, no one spends their time idly reading about CRMs. They're either in the market or they're not, and if they're not, who cares?

Rick: Yeah. That's probably not your story. I don't think that you're a CRM company. I don't think of you that way.

Tyler: Okay.

Rick: I think of you as a different CRM company.

Tyler: Yeah.

Rick: Your story may not be about CRMs. It may be about the approach you're taking to business.

Tyler: What does that have to do with the redesign, though?

Rick: The way you're going about it? Just right now, this topic is of interest to me personally. If I didn't know anything about this and how you're approaching the problem, I would be interested in you sharing that story with me and why you're doing it.

Tyler: Okay. So if I'm hearing you correctly, yeah?

Rick: You have a special approach to business and you're more or less annoying than you are CRM as a business.

Tyler: Okay. I buy that. So what you're saying is like, "maybe it's not, we're launching a redesign. It's here's how you can launch a redesign in a less annoying way or something like that."

Rick: Something like that. Well, I guess I'm getting to is it's coming back to the last podcast we did, when we talked about using employee handbooks for recruiting. And you had this philosophy that when people actually understand it, they go, "Holy cow, you are awesome. I like this job so much better." And it's like that aha moment where people go, "that's what you are!" You know? And you're different and I'm gonna tell people about you. And if that story could resonate with more people, and you have a reason to tell that story that's not annoying, then that would be cool. But you know, I've just said something out loud, that I think I need to take a step back on. Maybe what we're talking about here is annoying and that is your resistance to it. Maybe this entire tactic is something that just isn't who you guys are.

Tyler: Annoying is maybe taking it too far, but whenever I see other companies do this, it feels self-indulgent to be like, "you care so much about the inner workings of this." I really like focusing on the bottom of the funnel, like you mentioned earlier, because it's like, "these people are using it every day and they care about it, but does the rest of the world?" There's another problem here. I shouldn't say problem, but a reason for resistance for me. We're not trying to sell to startups. I'm very jealous of startups selling to startups, because they can tell their story and the people interested in learning from them are their ideal customers. But that's not true for us, for the most part. Our customers don't make software, they never have to launch a redesign, you know?

Rick: That's probably not the right topic then. The redesign may not be the right topic. I would challenge you to say, "is there a story here? Is this an opportunity for me to help more small business owners in a less annoying way" because you're gonna be communicating to a lot of people, right? You're going to be touching at least 22,000 people.

Tyler: 21,000 and then we've got another 6,000 on our newsletter that aren't customers..

Rick: Okay, let's just call it 30,000 people, who through your various channels, you're going to hit multiple times with the message. Why not make it bigger than just about redesign? The redesign is not why you're doing this. There's a bigger why that you actually are holding true to and why not maybe try some things in addition to those communications, to amplify it solely with the goal of figuring out if it might be beneficial to some other people?

Tyler: Okay. Yeah. With you saying that, some ideas are running through my head about, we can always do like, "we're doing this to make mobile better, but we're the only software company you use that actually wants to exist 20 years from now, and this is how we're doing this to earn your trust and yada, yada, yada." That's at least a little more marketing than what I've previously been talking about.

Rick: Are you scared? You're pretty authentic with everyone, right?

Tyler: I hope so.

Rick: So why are you hesitant to be super raw about this?

Tyler: Well, I'm not. We've written already, I think, six blog posts about this. We're being very transparent. We're talking about it.

Rick: I know what it is. I know the question. Why are you worried about this? Why did you bring this discussion in?

Tyler: The reason I brought it up is, I have a plan. Before the end of this, I'd like to go through what I'm thinking. This is the type of thing you can't experiment with very well. You do it and at some point, you pull the trigger and if I made a mistake, 22,000 people are going to be mad at me.

Rick: Got it. So you see this as you have a shotgun and if you miss, your dead?

What’s your current plan?

Tyler: Yeah, my normal approach would be to gradually roll stuff out and test it. But it's hard with this redesign, because at some point, we have to flip the switch for the majority of our users.

Rick: Walk me through your plan.

Tyler: Okay, and once again, this is less about building hype and more about just minimizing downside to this. Right now, we have about seven users using the new version, but the new version isn't really anywhere close to done yet. Which is why we don't have more people, but we just, earlier this week, launched the ability for anyone to opt into it. What I'm waiting for is one more round of improvements to the product. Because right now, pretty big stuff is missing. And then I was gonna email. I have a list of about a 100-150 people who asked to be in the beta test. So I was gonna email them. It sends them to this landing page. It's like, "here's what's changing, here's a video about it, here's a link to all the blog posts about it. Here's a form to opt in," basically. If they want the information, they can get it. Then we were going to wait till one of these new features is done. Outlook calendar sync is probably going to be the first one and basically say, "if you want this, it's only available in the new design. It's still beta tested. It's still not totally ready." A lot of people are gonna want Outlook calendar sync. So that was the point I was going to email the whole customer base and say, "this is beta test. If you want Outlook calendar sync, it's available, but you have to go opt in to the beta." Collect feedback at every step, obviously. And then the next threshold is, once we have onboarding help switched over to the new design, switch all new signups over. It still won't be 100% out of beta, but all new signups will go to the new design and then finally, eventually, we have to force all the stragglers.

Rick: What's your time frame for all of this?

Tyler: Yeah, hopefully. I would guess switching free trials over might be two months from now or something like that. We can kind of delay that last step as long as we want. We can stay in this limbo period. But the most urgency I have is to get new signups going over to the new design.

Rick: Yeah, so this reminds me of something that we experienced at PeopleKeep, where we had a legacy platform and we had built a new platform and we had to communicate the platform switch, which is a much more aggressive than a redesign. Because they had to literally reset everything up. Totally new user interface, new brand, new domain, new pricing. That was a big, big, big, big transition. What we learned from that is, if you are even considering forcing everyone to move over, at some point, you need to pick a date where you think that will happen. It probably needs to be six-ish months away. And you need to communicate that to everyone as soon as possible. It feels like you need to develop a significant communication strategy, to the whole group, as soon as possible with very clear, "hey, you can opt into each of these groups along the way, but you don't have to do anything yet." They go through a change. The whole idea here is, the people who you're scared of are the people who are going to be the stragglers. It's not the people are going to opt in, right?

Tyler: Yeah, absolutely.

Rick: Right? So those are the people that you have to let go through a long change cycle. Right? I don't know how many times it takes to communicate to those people, but the first time they hear it, they're going to be like, "that's annoying, but they're giving me six months notice, this is pretty cool. And I understand why," right? "Maybe I should opt into this thing, but probably not." And the whole idea here is lengthen the change cycle over time, until that deadline. And guess what you can do at the deadline?

Tyler: Delay it.

Rick: You can always delay the deadline.

What mediums are you going to use to communicate this?

Tyler: A constraint I put on myself that hurts me more than it helps probably is, I try not to email the whole list too often. It's been several years since we've emailed all our customers. One thing I didn't mention, we've been emailing our newsletter. People who opt in to more frequent communication. Every two weeks, we email the newsletter and every single newsletter has had another piece of information about this. One was like, "why'd we change our navigation? How's this gonna affect mobile compatibility? How are the settings changing?? We're kind of dripping that out.

Rick: Do your CRM coaches not reach out to accounts and say, "how are you doing?"

Tyler: We have a certain amount of automated stuff, at $10 a month. I mean, it's not.

Rick: How often are you sending a communication to a customer?

Tyler: Well, they're getting some form of communication from us almost every day, because we send a lot of email reminders and stuff like that. But we do the NPS survey once a year.

Rick: What about anytime of semi human, "hey, we're checking in on you" from support or service, to the client?

Tyler: We have tested that before and never found any meaningful evidence that that was benefiting anybody. That was years ago, so we probably should do that again. But right now, we don't do any of that.

Rick: What I'm getting to is, you really don't have a medium for communicating I don't want to say thoughtfully, but more personally and frequently to customers.

Tyler: Not something that feels like a person reaching out to me. For roughly half of our accounts, the owners of the account are on our newsletter. We email them every couple of weeks, but it doesn't have the appearance of a personal outreach. Yeah, I was hoping to only send one big blast to people. We could do two, though. We could get away with that. But what I'm hearing from you is, I was waiting for the Outlook sync to be done, so that there was something to offer them. And what you're saying is, get that out there as quickly as possible, even if there's nothing to offer them yet.

Clarifying your key messages and proof points

Rick: The topic of the podcast is how to communicate major product changes to your users. This is a communication challenge. And to solve a communication challenge, you need to communicate. Right? So when you think about communication, I like to think of it as there's two steps. The first is clarifying your communication. The core, right? There's a core message. There's only a series of maybe one, two or three messages that you want everyone in your customer database to understand. Correct?

Tyler: Yeah.

Rick: Okay. The trick with this is, you've got to figure out how to get those three communications in their head without annoying them.

Tyler: Right.

Rick: Right? At the end of the day, this is a question of how do you send as few communications as possible, or the most appropriate amount of communications, to maximize the number of people who get it.

Tyler: Yeah, and I'm already thinking, using the term communication, one way we can do this is popups, in the CRM.

Rick: Let me backup for a second. The framework for this is, first, clarify the three messages. Okay? As part of that, you need to add proof points to each of the messages. This is just like marketing a new product to your users. You would say, "listen, our key messages are we are redesigning this to make it more usable for you and more trustworthy." Message number one. "Here's some proof points of that." One. "We've had some initial testers. Here are some quotes, this is so much better, blah, blah blah." Maybe an industry quote that says, "new internet technology reduces time spent in an app by X percent." Just proving the key message, right? And you do that for each of your messages and then you get super aligned on those. These are what we want everyone to know and we want them to know the three key messages, but here's how we're going to sell them on the key messages. And those are the proof points.

Tyler: Okay.

Rick: They could be screenshots. They could be key feature messaging, whatever it is, but it's not what you want them to remember. It's what you want them to use to prove it. Maybe if you can get a case study from existing customers who are already switched over, you could use that as well. That's step one, getting the messages aligned internally. Then it's about, okay, how often do we need to communicate this to get the message across? If you can call everyone and have a one on one conversation with them for 30 minutes, you'd probably do it with one communication.

Tyler: Right.

Identify your communication frequency and mediums

Rick: Right? Now you've got to figure out, okay, how do we get there? And so one part is frequency of communication and the second is a medium of communication. And generally you want multiple touches, both from a frequency standpoint and from a medium, with the ability to somehow, once someone's gotten a light bulb to turn it off, so you don't annoy them.

Tyler: Right. Okay. I buy all that. That's interesting. Obviously, we'll send at least one email out. I mentioned earlier, like a pop up message. Just one thing. You mentioned calling, which probably the number of employees we have relative to the number of customers, it'd be tough. But maybe we could do that for the stragglers at the very end.

Rick: I would suggest that maybe you have some messaging in your head but you would benefit from writing it down.

Tyler: Oh, yeah. I'm going to go do exactly what you just said, for sure. I get your point there.

Rick: Yeah. I think that that's actually going to be the most valuable thing, because then you're going to realize exactly what, you're going to see, "oh to get this in everyone's head. That's going to require X amount of touches," right? Yeah. Yeah. 'Cause you're going to be able to put yourself in their shoes. Ah, sorry, go ahead.

Tyler: I was just kind of brainstorming. You were talking about different mediums. If there are other other mediums I should be considering?

Rick: Well, you said popups. One thing that we did, when we did the transition, is we actually had a pop up, when they logged in, that said, "hey, this is really important." And we messaged it and eventually it stayed. It had a timer of some kind, I think, that said, "you can close this for the next X days, but eventually you're gonna have to fill this out." And so it was opt out, but with an expiration date on the opt out and it required them to read some stuff and answer some questions. That by going through that workflow, it was pretty well assumed that they had agreed to, "I understand."

Tyler: Yeah.

Rick: And that was used as a way to say, "hey, we think we got the message across."

Tyler: Okay, so you got them to say, I understand, before the switch even happened.

Rick: Yes. Your problem here isn't the switch. It's getting people to understand why you're making the switch.

Tyler: Yeah.

Rick: If people understand why you're making the switch and don't like it, there is nothing you can do. What you're concerned about is the people who don't understand why you're making the switch and quit because they don't understand why.

Tyler: Yeah. There's a type of person that just rage quits at any change at all.

QUOTE: There's a type of person that just rage quits at any change at all.

Rick: What are you gonna do about that guy?

Tyler: Well, when I say rage quit, I think there is something to be done. Which is, there's this two weeks of outrage and then it's over. What I want is for that outage to happen before we switch them.

Rick: Exactly.

Tyler: That's why we've been trying to email them.

Rick: Rage quit, change cycle. Same thing, right? You're trying to get them through. There's a change cycle thing that says, "listen, you go through a change cycle, halfway through the change cycle, there's this huge danger area and that's where people rage and do crazy shit." Right?

Tyler: Yeah.

Rick: And then you want to get them through that, before you actually make them switch. You want to get them over that hump.

Tyler: Right. So then when they switched, and actually the call I referenced that didn't go well. I already saw that a little bit. It was a 45 minute call. During the call, she was really upset. By the end of it, she was already kind of coming down a little and then she emailed me a couple of days later and was like, "is the new design going to still let me do this thing that I can already do?" And I was like, "yeah, none of the features, we're not taking anything away. It all works the same." And she was like, "ah, well, I still don't like it, but, okay.

Rick: 45 minutes, though. Right?

Tyler: Yeah.

Segmenting Users

Rick: You can't afford 45 minutes for 22,000 users, so at the end of the day, what we're talking about here is how do we simplify the messaging, so that we know exactly what needs to be communicated. And then how do we measure whether or not that has been communicated, to get them through that change cycle before you transition?

Tyler: Yeah. Yeah. That's interesting. Getting them to like opt in, not opt in, but agree to it before the change has happened.

Rick: Not even agree to it. But say, "I understand why this is happening and I'm on board." Or "I understand this is happening. I have concerns." Or "this really sucks." Segmentation is key here. You have 20,000 users. Some number of them are going to be like, "this is great. No questions asked." Some are going to be like her, which are, "this scares me and if you can address my concerns, I'm not gonna have a problem with it." And the others are going to be like, "I don't trust you. This is a big threat. I might quit." The ones you are worried about, the second two buckets, you have to identify who those people are, so you can spend more time on them.

Tyler: Yeah. Okay. Interesting. Great. I've got a lot to think about here. Thanks for the help.

Rick: Was this helpful?

Tyler: Yeah, no, it definitely was. I have a specific plan that I had coming into this, which is not vague. Now, I have vague reasons, ways to improve it and I'm going to need to take this and, and brainstorm and think through it. But I definitely understand. The plan I had, I think, would have been okay. But I think there's definitely a lot of room for improvement there.

Rick: I guess, the reason that you came into this, you're a little bit scared of messing this up? Do you feel less scared about that now, having talked about it?

Tyler: I think so. Yeah. I mean, when I'm scared of something, my normal attitude is just explain it to death. Which is partially what you're saying here. So the amount of content we have written already and I'm starting on a different blog post about this today. I feel really good about the fact that we have so much content about this. I think the thing that this reassured me about is a better way to get that. I was focusing too much on getting the content to people who aren't going to get upset about it anyway. Well, how about I just summarize my take away?

Takeaways

Rick: Tell us your takeaways.

Tyler: So the first thing, before we got into why I brought this up, was probably there's a story to tell here. Most companies don't think about this at all, really. They just do it and it's sometimes a disaster. There's a story to tell that could be turned into some kind of opportunity to get people excited about it. 

Tyler: Separately from that, I think my initial intuition of communicate, communicate, communicate was good, but what you brought up is, it's important to actually have a strategy for it the same way you would with a marketing pipeline. 

Tyler: And there's going to be a change cycle. There's going to be a process of someone going from, "I've never heard of this before," all the way through, "I'm using the new product and enjoying it." And the same way you have to manage a funnel in marketing, you have to have, here's the point I'm going to hit at each stage of this change cycle. Here are these proof points I'm going to use to validate that and make it credible to the person. I'm going to walk them through the cycle and then specifically, I'm going to segment out the ones who, one way or another, I'm going to try to get them to raise their hand and say, "I'm going to be one of the problem people," and then I'm going to even communicate more heavily, maybe set up calls, do whatever we need to do to get them onboard.

Rick: Yeah, and I totally agree with everything you've said. One thing I'd add is the way that you can approach this from a marketing standpoint and sales standpoint, because that's what it is. This is definitely a conversion, right? It's a pipeline and you've got to figure out how to convert. It's going to be very dependent on your average revenue per user and your sales and marketing motion. You can't afford to have 45 minute calls with every user. Now, if you were a $10,000 per year, $20,000 per year product, maybe you could have a customer success manager schedule a call for 15, 20, 30 minutes and walk everyone through this. You've got to actually figure out how to do this with a thoughtful multi touch process versus a hand-holding.

Tyler: Although, having said that, we do have, I don't know, five customers that are over a thousand dollars a month. We should call all of them, for sure.

Rick: Yeah. Now you're getting into prioritization, right? Who should you prioritize, in terms of reach out and the limited resources that you do have, who should you spend it with?

Rick: One is the people at risk. Two is high revenue accounts.

Tyler: Awesome. Great. This is really helpful. Thank you.

Rick: You bet man. Well, great. So everyone, thank you for listening. You can join the conversation on this topic and review past topics by visiting www.startuptolast.com.We'd love to hear your thoughts and ideas. Tell us what you think and we'll see you next week.

What is Startup to Last?

Two founders talk about how to build software businesses that are meant to last. Each episode includes a deep dive into a different topic related to starting, growing, and sustaining a healthy business.