The Janna Bastow Hypothesis: True Product Companies Step Back, Focus, Measure, and Iterate

Janna Bastow is the co-founder and CEO of ProdPad. In this episode of the Product Science Podcast, we talk about how she learned how to really be agile and lean, why she started ProdPad, and how Prodpad makes product decisions.

Subscribe for the full episode on Apple, Google Play, Spotify, Stitcher, and more. Love what you hear? Leave us a review, it means a lot.


Questions We Explore in This Episode

The Janna Bastow Hypothesis: True Product Companies Step Back, Focus, Measure, and Iterate

How did Janna first get into product management? What were her first lessons early on in the job? How did

her company decide that they needed a product manager in the first place? How do you understand when you’re actually doing mini-waterfalls disguised as sprints? How did working with someone doing Agile right help Janna apply that experience going forward?

What traps do smaller companies often find themselves in when they’re constantly building? How do you learn how to break up work more effectively? How did Janna’s experiences as a junior product manager fuel ProdPad? How did they combine development of their tool with what they were already working on at the time in their day jobs? When did they know it was time to quit their day jobs?

What were the first few years like building a SaaS product? How did Janna’s consulting work help inform ProdPad’s development? How long did it take to get started? What helped them make the decision to avoid more traditional VC funding sources? What did they see in their funnel to know they were on the right track, and where was it leaky? What tweaks did they make to fix it?

How did ProdPad structure their free trial extensions to show customers how to get more value from the platform? How did they find a product solution to their investment problem? What kind of analyses did they do and what data did they look at to come to those decisions? How do they think about perceived effort versus expended effort for their target customers?

How is Janna applying her product mindset to marketing? How do you run experiments and iterate on other parts of your business beyond product? What did Holly learn from 10x Marketing Formula by Garrett Moon?

How did ProdPad come to create the now next later roadmap format? How do we reinforce roadmap behaviors that are ultimately unhelpful for software development? What was the top feature request for their roadmap, and how did that inspire them to change their approach? What’s the difference between a product company and an agency? How do you figure out the why behind your deadlines? What common misconceptions are there about now next later?

Quotes From This Episode

When we decided to really focus down, we had to drop everything we were doing and focus on improving this one conversion rate. And it worked and we learned several things. - Janna Bastow Click To Tweet If I'd known what I know now, I'd advise them to train their teams in what agile actually means. That's agile with a little a, because there were some monster projects that were just mini waterfalls disguised as sprints. - Janna Bastow Click To Tweet My co-founder and I said, 'If we had to do a roadmap but we didn't want to have this timeline thing, what would it look like?' - Janna Bastow Click To Tweet Be honest with yourself, be honest with your team, communicate those, do retros on how you work and what kinds of things that you've been doing as a team and what you can do to improve. - Janna Bastow Click To Tweet


Holly Hester-Reilly: Hi, and welcome to the Product Science podcast, where we’re helping startup founders and product leaders build high growth products, teams, and companies through real conversations with people who have tried it and aren’t afraid to share lessons learned from their failures along the way. I’m your host, Holly Hester-Reilly, founder and CEO of H2R Product Science.
Holly: This week on the Product Science podcast, I’m super excited to welcome Janna Bastow. Janna is the founder of ProdPad and has been in products for a long time. So, welcome.
Janna Bastow: Well, thanks so much for having me, Holly.
Holly: I would love to start with a little bit of background, learn how you got started in product and how you got to where you are today. Tell me, how did you first come across this discipline of product management?
Janna: Oh like everyone else, completely by accident. I never meant to get into product management. I dabbled in a mixture of different things, a little bit of design stuff, a little bit of customer support service type stuff, a little bit of sales stuff. I tried to do some business stuff in school. Turns out I was one of those Jack of all trades. And while I was a customer support rep in one of my first early jobs, my boss pegged me as somebody who was good at calling BS when I saw it and made me a junior product manager. At that time, I had no idea what he was talking about, or what that was, but it certainly sounded better than what I was doing at that time, so I accepted the role, and sat down at my desk and Googled, “What is product management?”
Janna: And that started my journey into what it is that I do now.
Holly: That’s awesome. And at that point in time, were there very many other product managers at the company you were at or did you not have many peers there?
Janna: There was really nothing around. This was a company that had been around for 10 years. It had gone public at this point in time. It had a product, but it had no product managers, and so I was plucked out of customer support and made a junior product manager. They plucked somebody more senior out of development and made him senior product manager. Neither one of us had product manager backgrounds, there were no product managers in the company. And this is a 400 person company, and we had no experience, and they just put us in a corner and told us to go do product management.
Janna: Both of us were absolutely baffled, and bemused, and we just started figuring it out from there. We learned it from the internet and from other folks around us from what we read online and tried to figure out what it is that our execs wanted from us. So it was really, truly, trial by fire. We had no idea what we were doing and spent a couple years just trying to figure out what they meant by a roadmap and a PRD and that sort of thing.
Holly: Yeah, that sounds like a really trial by fire kind of situation.
Janna: And I’ll be the first to admit, the first couple of years were… did it all wrong. I was writing huge, long, massive PRDs, I was writing UML. My first spec was 80 pages long, and it was only when I showed it to everyone, I was super proud of it, I thought it was perfect, I thought it outlined everything that we needed. I had every design in there. And I remember the moment that one of my developers said, “Well, yeah, but of course, I didn’t read the spec. No one reads specs.” And I realized that I was never going to write another spec like that again in my life.
Holly: Oh, that’s awesome. That’s really funny. One of the things that I’d love to find out about is the role or the relationship between the people who are practicing product management and the leadership of a company. And so I’m super curious with the story that you’re telling here. Do you know how these executives… How does a company get to be 400 people large without a product manager, and then all of a sudden realize it’s something they might need?
Janna: In this particular case, it seemed to be a company that I think lucked out in some ways. It found a particular niche building in e-commerce when e-commerce was striking lucky and doing well. And so it picked up on it and grew. It was a sales heavy type company. It was only as it started hitting that market maturity and plateauing as competitors started coming in, and they started having other players coming into the market who were faster, smarter, leaner, and more product savvy that they started realizing that they needed product management to compete.
Janna: To be honest, I’m not sure what was going on in their heads because I didn’t have a seat at that table at the time. But I suspect it was something like that. They started looking around and seeing that there were other companies who were bringing in product management that they realized that they needed this themselves. I think there was an element of cargo culting, as in, they saw other companies doing this and therefore they needed to do it because it was quite literally just a, “Oh, well, they have product people and they do agile, so we’re going going to have product people and do agile.”
Janna: And it was very much the literal do agile, as opposed to actually think agile and be lean. They just went through the motions of it rather than actually change the way that the company thought and actually started changing the way they worked. Which I think a lot of companies went through at that point in time. It’s very painful for a company to properly change the way that they work if what they’d been doing previously was working. They’d built something and companies came and they were making money. It’s really painful to realize that the way that you were working previously just isn’t going to get you from that next big step, or isn’t going to defend against this onslaught of new companies coming at you, nipping at your heels.
Holly: Yes. It sure is. I guess hindsight can be really helpful, right? With hindsight, it were, “Oh yeah, that’s probably what they were thinking.”
Janna: Yeah, exactly. Had I had a seat at the table, in hindsight, if I’d known everything that I know now, I probably would have advised them to train their teams in what agile actually means. They’re not agile with a capital A, but agile with a little a. And to really think about what steps they were taking because there were some monster projects that were put on the table that were just broken down into sprints, but we’re actually just mini waterfalls disguised as sprints. And my job as the product manager was basically just to shoo the sprint through.
Janna: And I didn’t know enough then to stand up against that and say, “No, we’re not being agile, we’re just acting agile. We’re not actually taking the time to iterate and to learn from this stuff.” So it took quite some years to realize that this wasn’t the right way of doing things, and to learn to stand up for the art of measuring and learning and iterating.”
Holly: So, then how did you start to learn that? What came next?
Janna: Lots of failure, lots of trying and failing and learning things as we go. Over time, I started seeing different projects take on lives of their own. About 10 years ago, I moved to the UK and joined a startup based here in the UK and started working with a much smaller, much nimbler, leaner team, and started seeing what it was to be able to iterate and move fast, and what it was to be able to have the direct contact with the customers, and to be able to build something and get it out there, and having permission to be able to change something on the fly and sort of that thing. And that gave me a real taste for what it was to be lean.
Janna: And that I think, almost had an almost addictive quality, I think to have that ability to iterate and to be able to measure something directly, and to change things as we go. I learned a lot in that position. A lot of what I learned, I’ve been able to apply to different roles and in different positions as I was as I move around.
Holly: I like how you said that had an addictive quality. It’s like once you’ve been through that, once you’ve worked that way, the other ways all seem just completely silly. Like, “Why would I not do that?” But if you haven’t tried it, you don’t know what you’re missing.
Janna: Yeah, exactly. I find that even small tend to easily find themselves in that trap of, Melissa Perri calls it, “The build trap,” where you catch yourself in this pattern of building and building and building because getting new things out, again, has this addictive quality because every time you get a new feature out, that new feature gets you that next download or that next sale or that accolade or that press release or whatever it is. And it does become quite easy to fall into that. But it is important to think about taking that step back and looking at… figuring out as to whether that thing that you built is, in fact, the right thing. Did it work? Did you solve the problem?
Janna: And even small teams tend to fall into that pattern of going, “Well we’ve built something. Just because we finished a sprint and it was successful, was it actually truly successful? Did it solve that… ” And so even in small teams, I’ve had to take that step back and say, “Should we be ring fencing a group of us to go explore over here? Should we be breaking this off into two tracks, or should we be taking a step back and taking two sprints out to go measure something? How can we break up this work to get in this discovery sprint or process or hackathon or whatever it is we need to do to make sure that we’re discovering as much as we are delivering?”
Holly: Yeah, absolutely. And just out of curiosity, when you joined the startup and started to work that way, what size and stage was to startup at?
Janna: I think when I joined were about 10 people. I was going from a 400 or 350 person company down to about 10 person. So culture shock, but in a really good way, really healthy way for me.
Holly: Yeah, I hear that. I actually really love the less than 10 people teams. I’ve worked on a couple and it’s… Yeah, it is so different. For me, it was the other way. I think I’m more… When I went from that to over 100, I was like, “What? This is weird.”
Janna: Yeah. Absolutely. We are going through that in the opposite direction here at ProdPad. We’ve just grown from 10 to 20 people, and looking at and keeping an eye out for the warning signs of what kind of things might be slowing us down, at what point in time do we need to look at… Is there anything that… Are there any warning signs of us going, “Hmm, should we be stopping to carve off extra time to spend in discovery? Or, are there any signs of us not spending enough time going back and thinking about the iteration and the measurement side as opposed to just the build side?” Because it’s a lot easier when you’re 10 people and you’ve got that easy communication, 10 people and the simple nodes of communication.
Janna: Once you’ve doubled that, obviously we’re aware of what kind of changes that might make, let alone when companies go to 100 people. So, very aware of how things might change as we grow.
Holly: Yeah. So you’re in a really interesting stage. I want to hear about that but take us back a little bit more to just founding it. What made you go and found ProdPad and what does that for that stage look like?
Janna: The founding of it, I think, goes back to the day that I got my job as a junior product manager. As in I went back to my desk and looked up what is a product manager, and I had no idea what I was doing. But, I did start finding information about the fact that, “Well, I needed to do roadmaps and I needed to write specs and I needed to talk to my customers. And so I started looking up resources to do so, and they didn’t really seem to be anything there. I was looking up like what kind of tools I was using, and everything else.
Janna: And along the way, I found that I was having to lean heavily on spreadsheets and whiteboards and PowerPoints, and things like that. And I always kept an eye out for tools to use this stuff, but I never really found anything. So over the course of the years that I was there; junior, and then once I moved to the UK, I took with me the PowerPoints and the spreadsheets and the tools that I’d hacked together. I’ve been making wire frames and bits and pieces that I’ve been carrying with me. And I had this idea, this nugget of an idea of something that I might build for myself, but I wasn’t a developer myself, or certainly wasn’t able to build something by myself until I met my co-founder, Simon, who was a product manager like myself, but had backend development skills.
Janna: First, I just showed him the idea of what I was trying to do because I wanted feedback from a fellow product manager about this idea of a tool set. He gave me some feedback on it, and then said that it would be easy to build because he could build the back end. And I pointed out that I could build the front end. And this is back in 2010 when back then you could build the front end out of jQuery and bootstrap and call it a day, so pretty easy. He built the back end out of Symphony PHP backend. We started hacking away. It was a hack project that we did on weekends and evenings. Didn’t quit our day job because we were both working leading product at a couple of different startups based in London.
Janna: And it was just this a tool that helped us do our day jobs. So it was a tool that helped us build our roadmaps to share with our teams and helped us write our specs, certainly leaner specs and simpler specs than the old PRDs that I used to write, something that our developers would actually read. It was something that helped us collect our feedback from our customers and tied in with whatever it is that we were building and putting onto our roadmaps, and then combined it all together so that our teams actually knew what it is that we actually did and understood where their ideas were actually going.
Janna: So it started off as just a tool to help us do our own jobs. We didn’t actually quit our day jobs 2012 when we started showing it to other product managers around us and they started wanting to get in on this thing. But at that point in time, it didn’t have a website. There’s no way to buy it. There’s no invite system, there was no onboarding system. So we quit our jobs, spent six months turning it into something that you can buy as a SaaS tool. Launched it in 2013. And we launched it with the idea that we didn’t want to go for that whole thing of getting funding and raising money and creating this big venture-funded business.
Janna: We just wanted to build something that added value to customers and could be customer-funded and build a business that way. So we focused on that, and got our first paying customer within the month. And that first paying customer is actually still with us today. Still, a product manager who uses it today, which is fabulous. And today, we have more than 1,000 customers around the world who use it to build their roadmaps and write their specs and collect the feedback from their customers. We’re still completely customer funded, bootstrap business. And 20 people in the business as of… Actually, we just grew to 20 people as of last week.
Holly: That’s phenomenal. Congratulations. That’s a really big milestone.
Janna: Oh, thanks so much.
Holly: That’s great. I love hearing about… I actually really like the term customer-funded as opposed to bootstrapped.
Janna: Some people use that bad word I hate called lifestyle business, and I’m like, “Well, it’s a business at the end of the day. We get our money by providing something of value to customers. It just so happens that we’ve spread the load amongst our 1,000 customers.”
Holly: Yes, absolutely. I agree. The first time I heard the word lifestyle business as a derogative term, I was like, “What?” Yeah. But that’s really phenomenal. I’d love to hear a little bit about the pace and the journey along there because I know, especially one of the benefits of not getting on the… not buying a ticket on the rocket ship that may or may not make it out of the atmosphere is-
Janna: [crosstalk] and energy.
Holly: Yeah. I only joined those rocket ships once they’d already been proven to sail. And then I was like, “Okay, I’ll have a seat here.”
Janna: I’ve been on that rocket ship, and they haven’t sailed. And you know what, it’s often a… There’s so many different factors that play into that thing. It’s heartbreaking. It’s really, really difficult. That was one of the forces that came into it. I’ve been in companies that hired amazing people and had great aspirations and had everything in place and just didn’t make it for whatever reason, and it was just heartbreaking to see things come and go that way. I didn’t want to be part of something like that, I didn’t want to build something like that.
Holly: When you go when you go this way instead, the pace can be quite different and you have so much control, but also so much responsibility. I’m curious how that has gone for you and what that journey has looked like, particularly say after the point where you launched it as a SaaS. What were the first couple of years like?
Janna: All right. Some words of wisdom in hindsight. I remember people telling me that it takes seven to 10 years to get anywhere with a business before it turns into anything that you can really write home about. I should’ve taken that and gone and understood how much effort would go into it. Because the first two years, honestly, it was actually just building it on the side and not quitting my day job. I was working for a funded company with a salary.
Janna: I couldn’t quit my day job because I needed that salary and I was working in London, and I was just learning the ropes and needed it to basically pay the bills. Once we quit our day jobs to go focus on it, I was still doing… I paid the bills by doing consulting and mentoring and training. I was lucky enough that I could do that in the product management sphere. I was doing product management training and mentoring and consulting, which had the benefit of me being able to learn about how product management works in a huge variety of different companies, and therefore how ProdPad could work as well.
Janna: So it actually exposed me to different customer groups and different… how product management works all over the place, which informed how ProdPad itself was built. So it was actually a nice virtuous circle in terms of user feedback and how we built the company, and I paid the bills at the same time. But, it did slow down the pace of growth in the company because I had to spend a lot of my time working and paying the bills rather than actually building the company itself. I also had to admit that I wasn’t the best developer in the world. I was building based on what I could copy and paste from Stack Overflow and what I could do in jQuery, which was never a skill that I was particularly good at, but just good enough at.
Janna: We had our first couple of hundred customers based on something that I built in my bedroom and that my co-founder built in his bedroom. So the prototype stood up longer on its own than it probably should have. It was a long time. It wasn’t until 2014, 2015 that we were able to start hiring anybody to help us out with it and turn it into anything. And there was a really, really rough patch in 2015 when we started hiring people, and we started seeing our cost base creep up.
Janna: As a matter of fact, it started passing our revenue base and it got scary. It got quite squeaky bum. And we started looking at options of, “Well, do we get the company funded even though it may not be the best option or not exactly what we wanted to? What kind of things do we do?” We had to really start thinking about options for the company. And the best option we had was actually to double down on what we’re good at, which was focusing down on improving the product itself. One of the problems that we had early on was that, we built the product, we had a decent number of people coming in from blogs that we’d written, like how to do a roadmap, how to write specs that your team will read, your developers will read, how to write personas.
Janna: We had an okay funnel of customers coming in, and this is our content strategy, but it was just, basically, myself and my co-founder writing. We had a decent number of people starting trials from that. We had an okay number of people who if they started trials, they would try it out and they’d use the product and they’d sign up. And once people signed up, we had a decent number of those people sticking around. So we had an okay funnel there. And we did this whole thing of, because we’re product managers, we did the whole thing of, build it and they will come. We didn’t have much in the way of marketing. We didn’t hire our first marketer full time in-house until end of 2018.
Janna: At this point in time, in 2015, we didn’t really have marketing per se, but what we did have was a leaky funnel in our onboarding rate. What we realized is that we had a lot of people starting trials, but not a lot of them actually quite getting it. Like our onboarding flow sucked because ProdPad was somewhat of a complicated tool. It didn’t really explain itself well once you started the trial. We knew that if we were able to tell people about the tool, do a demo to them or walk them through it, they’d get it. But if they didn’t get that, then oftentimes, they wouldn’t get the roadmap, which wasn’t… The roadmap isn’t a Timeline Roadmap, it’s a Lean Roadmap. So it’s the now, next, later format. Some of the ways that we do stuff isn’t necessarily well explained or at the time wasn’t well explained on the website.
Janna: So we had a pretty high drop-off right from the trial sign up. And so we decided to really, really focus down, we had to drop everything we were doing, all development work, all work that we’re doing and focus on improving this one conversion rate. And at the expense of all of our work, we cut down all of our cost base, everything and focused on this one conversion rate. And it worked, we managed to do a few things. One of them was, we actually focused on changing the trial length. So we used to have a 30-day trial, but we looked at the numbers and we did an analysis. We looked at; what kind of activities people would do in their trial? And we realized that we could tell with 85% certainty by day nine who was likely to buy or not.
Janna: And so, if we’ve realized who was going to buy by day nine, why did they have an extra 21 days to make up their mind or not? Why don’t we just ask them for their credit card on day nine or some other day? Why 30 days. 30 days was just an arbitrary thing. So we actually chopped the trial time in half. And actually, at that point in time, our trial conversion rate went up because the new cohort had less time, and because they had less time, they actually felt more pressured to use more of the features. And by using more of the features, they actually got more of the value. Because if somebody uses the features, they’re like, “Oh, now I, I’ve used the features, I now know how to use the features and therefore, I see more value, and I’m more willing to give you my credit card.”
Janna: So you could see how that… If you use the product, you’re more likely to get the product and therefore, you’re more likely to pay for it. But the moment we cut down the trial time, the number one support request became a request for more trial time, as in, “I’ve never run out of time, could I have more please.” And so, we’re constantly extending trials. What we did, we actually cut down the trial time again, but we set up a little trigger within the app that allows you to extend the trial yourself based on key actions that you do within the app.
Janna: So now, when you join ProdPad, you actually get seven days, but if you do key actions like fill in your company name, you get two days free. Tell us the name of your product, you get a couple of days. Add your first idea, get a day free. Set up a JIRA Integration, get four days free. Invite a colleague, get a few days free. Add your billing information, get some extra days free. So you actually earn extra trial time based on how you’re actually using the app itself. And so what this is actually doing, each time we do these actions, you get a little demo of how to do it and that sort of thing.
Janna: So people are learning how to use the app as they’re going, they’re getting that demo, they’re learning how to use each of the pieces of the app. And they’re unlocking pieces of the app, and they’re also getting the additional trial time that they wanted. And this itself actually bumped our conversion rate up hugely and bumped our numbers up and got us out of that slump that we had in 2015. So instead of solving it by throwing money at it and throwing investors at it, we solved it by throwing more of a UX and product mind at it.
Holly: That’s fantastic. I love how specific you were about many of the things in there. And I also want to mention that that’s actually, I think the year when I came across ProdPad, was 2015, probably through your self-marketing. I think I read an article of yours about roadmaps and I was doing an assessment for Shutterstock on what we could do, how we could come up with a better plan for roadmaps because we’d been only using decks. And so, I did analysis and tried to convince them to use ProdPad.
Janna: Oh, fabulous.
Holly: Yeah. This is part of why I reached out to you because I was like, “Oh no, I’ve known for years that ProdPad knows how good product managers work.
Janna: Oh, fabulous. It’s been working. Excellent.
Holly: But I’d love to hear a bit more about, and I recall, I think I read an article at some point that you called it like, The Magically Extending Trial or something like that. But tell us a little more… I love how as you were talking through, how you created that onboarding and trial experience to get people to do the actions that you knew would teach them more about the tool and lead to better success. You mentioned that there’s different amounts of days free that you get for different things that you do. Tell us a little more about how you came to those numbers and what kind of analysis you did to make those product decisions?
Janna: You’ve got to start somewhere. So the first numbers we came up with were a mixture of gut feel and looking at some of the numbers that we were looking at. What we realized was that there were certain key actions that resulted in success, things like people who had more than one colleague in the tool, as in, had invited another colleague, were more likely to pay for ProdPad, which makes sense. ProdPad is a collaboration tool, and if you collaborate with others, then you’re more likely to buy it. So things like inviting a colleague are more valuable to us in the end. And therefore, you should get more time for that.
Janna: So that one earns you more time than say, something simpler like adding an idea. It’s also more perceived effort. There’s more, I don’t know, mental effort or I guess, it’s almost like political expenditure to invite a colleague, even though it doesn’t take more effort to type in a colleague’s email address. So we’re like, “Okay, well, here’s three days for typing in your colleague’s email address versus one day for typing in an idea that you might have pinned a Post-it note on your wall right now. So that was one of them.
Janna: Some of them are things that take a little bit more effort. Things like setting up a JIRA Integration, we know that it takes a little bit more effort to do so, and therefore, the payoff in doing so, you get a little bit more. That’s why you get more days for doing that versus some of the stuff that’s easier to do. We also know that setting up an integration is a stickier, its an indication of a stickier customer, so we give more time for that. A customer who has JIRA integrated with ProdPad is considerably more likely to stick around and use that. Again, that makes sense, and therefore, we give more for that.
Janna: Other ones are things that make sense for us. One of the ones that is a little bit the dark horse, is the fact that if you have collected everything, so you’ve added your product, you’ve got your first idea in there, you’ve got your colleagues invited, you’ve added an integration, you’ve got your first persona, you’ve done all the things, at the bottom of the list, it says, “Add your billing information.” So you’ve got 28 days, you know you can add an extra four days by adding your billing information early. Instead of having your thing expire now, you can actually extend your trial by an extra few days by adding your billing information today.
Janna: That one actually benefits us, and you, because you get an extra few days and we actually have people go through and collect all the days. And that way, they have that peace of mind that the trial is not going to run out. And have the peace of mind that your credit card is in there. We now know, or we’ve got pretty good reassurance that you’re going to be a paying customer. And we’re all happy. We’ve got a new future client on our hands. So we looked at it that way, but then we also set it up so that it was configurable. So we could test these things and check and figure out which ones actually did result.
Janna: So of the people who did X, Y, and Z, did they actually become paying customers? Did they actually result in that sort of thing? We also set it up so that we could add new things to it, and so we can adjust them and tweak them and move them around. The number of days that you can actually collect is arbitrary. Today it might be 35, down the line, it might become 45 because we add new things to it. We actually don’t really care how many days you trial, we just want to know that at the end of it, your happy customer and that you have had enough time to understand the app and you’re happy with it and you’re good to go with it and your team is on board and you’re successful with it.
Janna: We don’t ask for the money before you’re comfortable with it. That’s key to us. And so the trial is really just a way of making sure that you are feeling like you’re getting something in return for putting the effort to learn about it and to test it out and to get your team on board, and that sort of thing.
Holly: Got it
Janna: Yeah. It’s a sort of akin to… Dropbox gives you a storage space, and Slack gives you credits. But we don’t have a credit system or storage space limitations, so we give trial time.
Holly: Yeah. That’s great. Now that you’re running a company, as a product minded founder, tell us a little bit about, have there been things that have been surprising about running the company? Not necessarily, maybe it’s within the product area or maybe it’s outside of it. What does that experience and transition been like?
Janna: Oh, what’s been surprising? Lots of things, I guess. I think one thing that’s been very surprising is how it’s not all about product. It’s been a huge learning for me about how much is required in terms of marketing and actually telling people and telling them again. We did the classic product thing of, build it and assume that they will come, where what we build, we built it, and most of them, we did have a lot of customers come. But then we’d realize that good is sometimes the enemy of great, where we had good enough marketing but not a great marketing.
Janna: We’ve never really dabbled in paid advertising, or really dabbled in too much in the way of social media or much beyond our own blog. We’ve done some guest blogs, we’ve done bits and pieces like this, things like this, I occasionally do, podcasts and talks and bits and pieces like that. But to be honest, I think there’s so much more that we could be doing out there and I think it’s a new learning area for us. But, what’s really interesting is that, I’m taking it with a product mind. I’m looking at it going, “Listen, marketing, just something that can be measured and learned from and iterated upon as we go. And therefore, what can we do to almost approach it like a product manager, approach it like a scientist and figure out how we tackle it from there.”
Holly: Yeah, absolutely. And you can. That first rocket ship that I decided to take a seat on was in marketing, so I learned… We had teams inside Mediamath that analyzed and ran experiments on all the different levers that you could pull and figured out what impacts, changes in each of them made on the bottom line for the marketing.
Janna: Excellent.
Holly: Yes. And I will also share as a fellow business owner who had to ramp up on the marketing side for my own business. One of the books that’s really resonated with me because it speaks to the agile lists mindset, is this book called 10x Marketing Formula by Garrett Moon. He’s the founder of CoSchedule.
Janna: Oh, that’s right. I know that one.
Holly: Yeah. I really liked that one. I thought that one really spoke well to this, you’re going to test and iterate and you’re going to find out what customers want and all of that, but you’re just applying a marketing plan instead of a software development plan to do what you’re doing with it.
Janna: Okay. I really love that. Thanks for the recommendation. I’ll pick that one up. I feel like there’s a whole area that I need to absorb and learn from. And so, I feel like I’ve got to take all these recommendations on and figure out what I don’t know.
Holly: Yeah. Well, I think it would make sense to spend a little time on the stuff that you do know. So one of the things that I love about ProdPad is, is the way that the roadmap is not based on dates. And so I’d love if you could tell a little more, you must have had a lot of experiences both yourself and then with your consulting work about, how have different companies reacted to that and what are your go to responses for people who are hesitant?
Janna: Yeah. Absolutely. Perhaps it’ll help to tell you about how we came to that format, because a dirty little secret, the first version that was built in ProdPad was actually a timeline roadmap. And this is before it was actually called ProdPad. This was back when it was a tool to help me do my own job because my old bosses, my old execs, they wanted me to provide them with a timeline roadmap, just like every other product manager that I knew back at the time. And you know what, every time I showed them this Gantt chart of a roadmap, they patted me on the head and told me I was doing a good job and reinforced it.
Janna: And I would diligently go back to my teams and try to get them to build the features that I’d outlined, and I’d feel terrible when something would slip and I wouldn’t be able to do it. And each month, I’d end up inevitably taking a few items on that roadmap and everything forward from that list and shuffling it forward by a few pixels or a few columns or whatever, in order to make space for that, whatever was offered outwards. And I thought it was just me, I thought it was just me who was just a terrible project manager and a terrible product manager by association, and not able to come up with the right estimations and not able to quite build out the right features and build out the right stuff in the right time.
Janna: And everyone else was able to do so because every other product manager seemed to have this fixed roadmap, and they would just be happily building along it. But it wasn’t until-
Holly: No.
Janna: Okay, right? It wasn’t until we built ProdPad that I started exposing it to other product managers around me, and they started using these roadmaps and their execs gave them praise for showing them this nice shiny new jQuery enabled drag and drop Gantt chart timeline roadmap. And the feature requests started coming in. And the top feature request was the ability to select multiple items in this timeline roadmap and move them all across by like a month, all at the same time. And had I just listened blindly to the customer feedback, I would’ve just had like a multi-select drag and drop tool and just like be like, “Yeah, sure. Move everything across. June didn’t work out so we’re going to do that July, puzzle. Let’s go. Q2 is the new Q3, sure.”
Janna: But I asked the five why’s and dug down to like, why fundamentally are we all missing our deadlines? And that’s when I realized that these deadlines are completely arbitrarily made up dates that we’re giving people and the dates don’t actually matter. And so Simon and myself, my co-founder of ProdPad and myself, sat down at a coffee shop in London and ripped up the timeline roadmap and said, “If we had to do a roadmap but we didn’t want to have this timeline thing, what would it look like?” And Simon sketched out three columns, and he put current, near term, future.
Janna: And we sketched out these three boxes and said, “Well, what if we just throw what we had and just put it together like this?” And I pointed out that it’d be a heck of a lot easier to rebuild this in jQuery and we wouldn’t have to worry about X, Y, and Z, no dragging and dropping, all that junk that I’d just done. And it was a little bit gutted of having to throw out all this work that I’d done, I was in love with the interface that I’d built and I kind of got it that I was throwing out a bunch of work, but at the same time, I realized that it would probably save peoples heartache.
Janna: And I figured the worst thing that would happen is people would say, “Nope, I don’t want it.” And so what we did, we put it out there and started showing it to people. And what was really interesting is that the feedback that started coming back was a lot of triumphs. There was a lot of people who loved it. And what was really interesting is that we kept… because we actually questioned as to whether we could still call it a roadmap. We really doubted ourselves going, “Well, it’s obviously not a roadmap anymore. We can’t call it that because it doesn’t have the roads anymore. It doesn’t look like a roadmap. So are we allowed to call it that?”
Janna: And we decided to call it a roadmap. And what we realized that had actually happened is that we’ve almost taken the name roadmap and re-done it. We’ve taken that name roadmap and changed what a roadmap means. It’s as if we’ve given product managers permission to not do old school roadmaps, to change the way they’ve done stuff. Because you know what, when execs now say, “Can you do a roadmap?” They can look up roadmap and they have two different options. They have an old school roadmap or they have a now, next later roadmap. They have different ways of doing it, they don’t have to have a timeline now.
Janna: And so, whenever I talk to people who are trying to get away from the old school version of roadmaps, I always ask them to figure out like, why are you being asked for this timeline roadmap? Who is it that’s asking? Is it a customer who’s asking for it? Have you made somebody a promise and you’ve got like some contractual date that you’ve agreed on something? Is your company an agency? Is this your business model to do so? If so, then you’re not a product company or an agency. And there’s no shame in being an agency, but remember, agencies don’t change the world. Agencies just make some money. And that’s the business model.
Janna: That’s okay, but you’re not a product company, so just come to terms with that. Are you doing this because you’re in a slow-moving regulated world and you literally cannot, there’s laws that are preventing you from being able to work outside of these regulations and these terms? If so, are there things that you can do to carve off, can you carve off just a percentage of your workforce to break out a startup lab or a hackathon or 20% time or 2% time or something to become slightly more lean? Are they arbitrary deadlines?
Janna: Are they things that your boss is imposing on you just to have the sense of control? Or are they actual strategically important externally driven deadlines that are important because they’re the law or because they are market driven deadlines like Christmas is coming and your eCommerce? We always figure out, why you have these deadlines, why you have these constraints, and drive back from there and question the reasoning at the source.
Holly: Yeah. Fantastic. That is actually where I hit the problem in trying to get Shutterstock to adopt ProdPad. Because at that point in time, I was a group product manager, so there were VPs above me and PMs below me and other people at the group and director kind of level. And so I didn’t have… I tried to make the case that we should go to this dateless roadmap, and there were some people there who were like, “That sounds interesting.” And then there were other people who were just like, “I do not possibly see how I can go to our leadership and tell them that this is a roadmap.”
Holly: At the time, I decided that that wasn’t the battle I was going to fight at that time. And I was like, “Okay, well, just let this go.
Janna: One common misconception is that Now Next Later roadmap doesn’t have any dates. Sometimes you have to wean your company off the time, the date roadmap. The problem with a timeline roadmap is that, it chart with time along the top and therefore, everything underneath it has a date on it. Like just by the format, everything has a date. Whereas the Now Next Later format doesn’t have dates on anything unless you explicitly put a date on it. Sometimes, things have due dates on them. I remember last year, every company in the EU, actually almost every company in the world had a GDPR card on their roadmap somewhere. It had a due date.
Janna: I’m sorry, we all had that card and it all had due dates, even us with the timelineless roadmaps, like a dateless roadmap. Just because… It sat in the now column, it was something keeping us busy, and it had a date on it. And that’s okay. You’re allowed to have a date in there, as long as you’re explicitly saying like, “This is something that’s due and here’s the things that we’re working on that are below it and above it and everything else.” And it’s just there to communicate like, “Here’s the things that are priority, that are taking priority, and here’s the things that are important.”
Janna: But it doesn’t necessarily mean that you have to have it represented in this line that stretches out with this end date on it. And everything else represented with magical end dates that you’ve made up around that as well, because you don’t know those magical end dates. Just because you are forced to come up with a date, you’re forced to stay to date for one thing, it doesn’t mean you should magically make up a date for literally everything else around it. Which is the problem with a timeline roadmap.
Holly: Yeah, absolutely.
Janna: So sometimes it’s easier to wean people off the format, and if you can get from having 100% dates to just 50% dates, you’re doing better. If you can get that down to 10%, even better.
Holly: Yes. I like that you talk about weaning them off of it. I’ll say that that’s also what we do with most of our clients now. And what I landed on for the things that were in my circle there was that within the PowerPoint Decks, I would create roadmaps that were more of a Now Next Later, but would tell you the date for the things that I knew, which is close enough. I know when we’re doing this, it’s fine, and then the others would just be like, “Hey, I’m in the future.” So we really did go that weaning direction. But just, I think faced some challenges with getting people to say for an entire group that they would all be willing to use this, you know.
Holly: And another thing that you mentioned in there is, I love the GDPR example. Everybody will have gone through that really. And then the same thing with Christmas and these other dates that, those things that do come up. And it’s good to hear how you recommend people, show that for people who are concerned. I think the other thing that I’ve come across a lot that I’m curious to hear if you have a perspective on what you tell people is sort of that control. The control minded pushback.
Holly: The one where it’s like, “Well, there’s no good external reason for this. Christmas is not an important date to us.” It’s just that the people at the top of this company don’t feel comfortable trusting their teams to deliver fast and furious according to their own objectives rather than with the timeline that they’ve produced and told everyone they would follow. What do you tell people in that situation, what do they do?
Janna: Really interesting. Marty Cagan did a really good talk about this recently at MTP Engage. The video’s out as well. That might be interesting to share, but he talks about trust being a huge factor in empowering your teams. One of the things that I see that comes up time and time again, is how teams are being forced to make these promises on exactly what it is that they’re going to be doing and then stick to those promises in order to provide this level of reinsurance to some of execs somewhere, as to what it is that’s going to be delivered.
Janna: And what that actually leads to is people adding all this buffer, because if you’re not quite sure as to what is you’re going to do, you’re going to add some buffer so that you cover your own butt, so that if your two day project actually ends up taking four days, then at least you said five days. And therefore, work expands to fill the time that’s taken. So if it takes four days, you’re cool. So all of a sudden, two days ends up taking five days and things end up slowing down, work ends up slowing down to fill the space. So you end up working as a team slower and slower and slower, and you end up becoming…
Janna: This is how you end up with teams who are huge but get way less done than micro teams. But also what happens is that, if you have this arbitrary deadline, like let’s say, you’re told to get a feature out by two weeks time, but at the end of two weeks, something’s gone a little bit wrong as things do in software development because things do. At the end of two weeks, something isn’t quite right, and the developers have the choice of making it right, but it’ll take an extra week. Or they could get it out to the product manager and to the customers and to the execs, it looks right, but you know what, they could’ve done a better job with some unit testing or with the coding or it probably could’ve been done better, the documentation could’ve been done better.
Janna: There’s always something that could have been done better. So that stuff gets left and maybe they planned on going back and fixing it in V2, but V2 is the biggest lie ever told. No one has ever given permission to go back and fix it in the second version. And so if they launch it that first week and they never get the chance to go back and fix it. And this is where tech debt comes in, because if you’re told to launch something and you never get that permission to go back and make it as high quality as it could be, this is the type of tech debt that causes companies to grind to a halt two years later when their tech debt has just piled up and no one wants to train on it.
Janna: They don’t have the documentation, no one is able to understand why it was built a particular way. It’s littered with to do’s and unfinished comments, there’s no unit testing or whatever else. And they wonder as to why they’ve got startups who were able to outperform them, who are moving fast and eating their market for breakfast. And so this is how big slow moving companies are getting absolutely eaten alive by faster moving startups.
Holly: Yes. As soon as you started that, I was like, “Tech debt. Tech debt.”
Janna: I tell my developers to build their products. We don’t do deadlines here unless absolutely necessary, like GDPR or there’s an event coming up. And even then, we try to make sure that we’ve got everything at possible in place to make sure that we’re not building up tech debt or organizational debt or any debt really. Because the way that I look at it, I tell the developers to, “Build it in a way that you would be proud enough and happy enough to launch this and explain it to a developer in two years’ time. Imagine you yourself are going to be training your junior developer in two years time and you have to explain why you built it this way using your own documentation, your own comments and the code and everything else.”
Janna: “You want this thing to be standing up and you want to be able to be proud of this work. Because you’re going to be supporting this code in two years time and you’re going to be training new people on it. So don’t just finish it to make it look good to your product person and to the customer, make it look good to the people who are going to be building on top of this. Don’t just build this in a quick way, build it to be good. I don’t care if it’s going to take an extra three days, make it good. I know it looks like you’re doing nothing, it doesn’t look any different to us, I’m not going to question you. Just make it better, do what you need to. And hopefully, in two years time, we’re not doing a refactor.”
Janna: That’s the type of thing that we’re at, we’re hoping to, it’s going to make a difference.
Holly: That’s great. And that kind of thing also attracts better talent, so you’ll get better coders if they know that this is a place where they have the space to do it right.
Janna: Yup. Exactly.
Holly: And then that feeds into each other and it’s all interconnected. Awesome. Well, I think we’re about out of time. This has been fantastic and I’m sure I could talk about these things for a much longer with you. What would be your final words that you’d want to share with maybe a product minded founder or product leader who’s in the thick of it these days?
Janna: Really good question. Any product minded founder who’s in the thick of it, I always recommend to think about any of the processes that they’re going through as a product in itself, as something that can be measured and iterated upon itself. So always think about the processes that you’re doing, take a step back and think about what kind of things you can do to measure those and improve upon those. Be honest with yourself, be honest with your team, communicate those, do retros on how you work and what kinds of things that you’ve been doing as a team and what you can do to improve on those. And you’ll constantly see those improvements take place within your team as you grow.
Holly: Great. I love it. How can people find you if they’d like to follow you or ProdPad?
Janna: Come find me, I am Janna Bastow on LinkedIn. Come connect with me there. I am simplybastow on Twitter, so come follow me and say hi, my DMs are open. And come try out ProdPad. It’s a free trial. You can try as long as you want, and that is
Holly: Wonderful. Well, thank you so much for your time. It’s been a pleasure.
Janna: Well, thanks so much for having me, Holly. This was a great conversation.
Holly: The Product Science Podcast is brought to you by H2R Product Science. We teach startup founders and product leaders how to use the product science methods to discover the strongest product opportunities and lay the foundations for high growth products, teams, and businesses. Learn more at
Holly: Enjoying this episode, don’t forget to subscribe so you don’t miss next week’s episode. I also encourage you to visit us at to sign up for more information and resources from me and our guests. If you love the show, a rating or a review would be greatly appreciated. Thank you.