S1 Ep. 2: Does Your Product Roadmap Contain What Will Happen or What May Happen?

Written By Hope Gurion

DOES YOUR PRODUCT ROADMAP CONTAIN WHAT WILL HAPPEN OR WHAT MAY HAPPEN? Are you a new product leader? Are you struggling with how to create and communicate your product roadmap? In this episode get actionable advice on how 5 product leaders approach creating and sharing the product roadmap with their organizations in B2B, B2C, startup, growth and mature companies.

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DOES YOUR PRODUCT ROADMAP CONTAIN WHAT WILL HAPPEN OR WHAT MAY HAPPEN? // Are you a new product leader? Are you struggling with how to create and communicate your product roadmap? In this episode get actionable advice on how 5 product leaders approach creating and sharing the product roadmap with their organizations in B2B, B2C, startup, growth and mature companies.

Hope Gurion: Roadmaps are a hot and enduring topic amongst product leaders. Why? Because everyone wants to see how everybody else creates that magical document that helps their organizations deal with short-term and long-term planning needs. I often find that new product leaders struggle with the distinction in their roadmap communications between what will happen and what may or may not happen.  That’s our focus for this episode.

Hope Gurion: Welcome to the Fearless Product Leadership podcast. This is the show for new product leaders seeking to increase their confidence and competence. In every episode I ask experienced and thoughtful product leaders to share their strategies and tactics that have helped them tackle a tough responsibility of the product leader role. I love helping emerging product leaders shorten their learning curves to expedite their professional success with great products, teams and stakeholder relationships. I’m your host and CEO of Fearless Product, Hope Gurion.

In this episode of Fearless Product Leadership, we will hear from experienced product leaders who have led product at multiple companies answer the question: Does your roadmap contain what will happen or what may happen? Often this is a matter of how far out the roadmap is expected to cover but you’ll learn on today’s episode how confidence levels factor into roadmaps, and even more important how the decision-making related to roadmap priorities is way more important than the document itself.  

Let’s get right into it.  In this episode we hear from

·      Lucinda Newcomb, VP of Personalization at Walmart and former VP of Digital Product at Sephora

·      Stefan Radulian, Head of Product Management at Brainloop, a Diligent company

·      Lauren Antonelli, former head of Product and now Chief of Staff at evite, 

·      Brandon Anderson, VP of Product at Sportsengine

·      Margaret Jastrebski, Product & Strategy Advisor and former SVP Product at Shoprunner

Hope Gurion: First Lucinda Newcomb of Walmart.com shares how confidence decreases in roadmap items further out and that how decisions are made to change what is in the roadmap, is far more important than the document itself.

Lucinda Newcomb: I believe that our role in terms of owning the roadmap is really as a steward, we need to be a good steward of the roadmap. Which is to say, I don't ascribe to the notion that product managers are the CEO of their product; partially because I tend to do product at retail companies where we sell lipstick, or we sell pants, or we sell toilet paper. We sell all these things, what we sell is not the actual product that I manage. So, for me - and maybe it's different on the other side - but for me, I've always looked at this as, my products are the customer experiences that help you make decisions and purchase items. So, with that in mind, we are the steward; so much of what we do, is we need to be good buddies and  it's the buddy system working with our business stakeholders, to help understand what are they trying to accomplish, what business problems are they trying to  solve, so that we can then create a clear, well-balanced roadmap that accomplishes  what we need to. So, when I have always  owned roadmaps in the past, it has very much been - it's not about me going off in a corner and cooking something up nor is it about me just taking last-in-first-out sort of situation of  just taking the orders; it is about, how  do we bring together all of the  different ideas and align together around, “Here are the top ones that we're actually going to invest in and  here's what it's going to take to invest  in them” and drawing our line and then  moving forward with that list.

Now, the trick is, a roadmap always has to be a living breathing document. I'm a huge believer in trying to have a 12 to 18 month roadmap. However, whereas I may have  95% confidence in the current quarter  and I have 80% confidence in the  quarter after that, I'm at 50%  confidence in the third quarter and I'm  at 20% confidence in the fourth quarter; because I guarantee what's in that  fourth quarter is going to end up in the  following year. So, I always look at  it as, first you come up with your  priorities and then you figure out  what's the order in which you're going  to attack them in terms of your roadmap  and that roadmap always needs to be  structured around where do you have the most bang for the buck and the most  business benefit, solving the most urgent needs. Recognizing that what does in q4 is very likely to not make it out, because if there's one thing that is true, you can adapt to the roadmap to reality, you cannot adapt reality to the roadmap. I've tried, it does never work.

So,  when you think about that, once you have that roadmap, it's always about how do  you have frequent check-ins to make sure that the roadmap continues to be  appropriate for the reality that you are finding, because every day things change. So, what I like to do is have a monthly meeting with all of the key stakeholders and talk about, “Here's what we've just launched, here's what's in progress and  here's what's coming in the next quarter” now, are there other things that we  believe have either become more important or less important, that we should push out, not stop in the middle of, try to avoid that, but anything that's  in the next quarter, are there things we should push out to make room for other  higher priority initiatives? What I found is, even when I'm in a situation where I have an apples to oranges to pineapples to zebras, where all the different business stakeholders have different initiatives, having them in the  room together, where we already have built out our business cases; it's very  important you have a business case for, here's what the initiative is and why it  is on the list in the first place. So, that if somebody says, “Hey, I think we should do X, instead of Y” you say, “Okay, what is it that you think we're going to  get out of X and is it more than Y?” and/or is there a strategic kicker? I like to  call them that actually makes it like  even though it's less money it actually is more important  from strategic perspective or it gives us better PR there's some other  intangible or qualitative reason why I  should go higher and make that proposal and then tell me which of the things that are already committed, should come out. Brick-in-brick-out, you can't throw bricks in there without helping identify what bricks you think should come out. 

Then, it becomes a conversation, where everybody in the room has to put on  their broad or company hat, not on their ‘my initiative hat’ and this is the pain  that I personally need to solve, but  getting everybody to think about the  fact that we all need to put on our big  company hat and our big girl pants and  talk about what is it, is this new thing  actually that much more important than  the thing that we're proposing or the  alternatives we have of what we could push out. So, I've found that with  that transparency and with the trust of  the people in the room that it's never about playing favorites or politics, it's always about, let's all together discuss, how are we going to get  it right for the customer at the end of  the day. As long as you're always  focused on the customer, is at the end of  the day going to be the most important thing, of delighting that customer? It helps squash a lot of the different conversations in the room and helps lead people to make better decisions. 

Ultimately, you need to be making a road  map that is well informed by all of your  stakeholders that they get aligned around and then they get bought into you  and then when new things come up, it's a lot easier to have the conversation  around, why would we move something up or move something out, because you have the  transparency and because everybody is part of the conversation. Even if they choose not to come to that meeting, they need to know that that is the meeting where they get to ask for new things or complain about other things. It can't be, I used to call them the  gremlins, the emails that they would send a week after the meeting and be like, “Oh, but could you just, can you just look at this, it's super quick” no. Once, you align and say, “Here is the roadmap” that is what is the roadmap and you have a monthly conversation where you meet. Maybe, in a smaller company, that's more frequent but you have that window where you reopen the discussion, but it is not reopened by somebody's desk, in somebody's email, or in other forums. It has to be, here is where everybody gets to come in and have an equal voice and equal participation. It doesn't mean they get an  we'll say, because ultimately, there has to be  somebody who makes a decision, but it  does mean that everybody gets a chance to be heard and to weigh in on the  conversation and then you can come out with yet again, a roadmap that everybody  is well they may not agree with it, they  need to be aligned, with these are the  right things to do for the company.

Hope Gurion: Next, Stefan Radulian who leads product at Brainloop uses the analogy of a flight schedule to describe his roadmap philosophy and approach to deal with his organizations’ desire for roadmap certainty with the reality that product teams need flexibility.

Stefan Radullian: The roadmap that we create does not contain what may happen. we try to be as realistic and as a certain as possible.  I like to compare it with  a flight schedule, a monitor at the airport; so, we we are doing these calculations and try to find the most realistic, most probable scenario that  can happen in the future, but we know that that the system is complex and there are some things that you just  cannot predict like, for example, weather or machine breakdowns hopefully where when they're still on earth and then how  long it takes to service them and all  these kind of things. This is a very complex system and schedules can change anytime and a roadmap is a snapshot of that schedule, it's the most probable scenario that we we think is realistic today and it can change. So, in a sense, it the roadmap is what may happen, because you can't predict the future, but it's still a plan, it's the old plan.

So, if we are committed to deliver that kind of roadmap businesses; so, in mostly the b2b business, I'm talking about b2b roadmaps here. they will be grateful for that, because they themselves want to have certainty in their plans. So, it's all about certainty here, people just want - it's a psychological thing - people want certainty and we try to deliver that certainty with the roadmap or at least  reduce uncertainty a little bit, by  telling them look this is the most  probable plan.

Hope Gurion: What is the accompanying message/disclaimer/ state of mind that you think has to go with it for it to be a helpful planning tool and not used as a weapon against its creators?

Stefan Radullian: There's one little improvement that was actually significant, that we did in our roadmap slides or the way we put it. It was when we changed from feature description to problem description. So, what we what we commit now is we will  solve that problem by that date and not very precise on the date, but let's  say, in that quarter we are going to address  that particular problem and we will find  a solution we will not tell you how. Previously, we were putting features and  writing it, “We will build that  checkbox into that product and if you do that, you will get that and if you do that, you will get that” and we remove the day away from that that lends us the flexibility and then the freedom to find short-term solutions to the problems that  we are trying to solve. Yeah, so that’s the trick.

Hope Gurion: Next, Lauren Antonelli of Evite describes how they evolved away from having roadmaps in favor of strategic priorities which enables Evite’s product teams to focus on learning, instead of breaking roadmap promises.

Lauren Antonelli: I get why roadmaps are necessary, I totally understand. Where we started was, product building roadmaps and then it felt like - in a word you know a hundred people or so - it felt like well product is making all the decisions where the business is going. There are five  people, like why should they decide? Even though, it was very influenced by a CEO  and everything else and we were  working on what I think was the right  things, but in the end I just realized  like that idea of product being a black-boxed, was contributing - like well I don't  know why they made these decisions.  What impact does this have on the business in five years, in ten years?  Then, I started thinking did we even design the roadmap that encouraged that kind of stuff?

When you start to be real about capacity, you start to really realize that you were only going to get so much done in a year, I think that's where  you get the benefit of having really honest conversations about what you should be working on and what should  make it into that roadmap. The evolution of the product roadmap at  Evite, has ended up in a much different  place and part of that is by really defining what the business needs, from where it is now, to where it needs to go, the strategic avenues to get there and  it's sort of like placing bets. We really  have nailed it down to the projects that will drive those priorities and we did that as a communal company; why  not? We're lucky enough to have a product that everyone in the company uses. Online invitations are for everyone, we throw parties at  Evite, people are moms and dads, people have kids birthdays, they have happy hours and bridal showers; why not get the most benefit of people understanding  how to make getting together easier, from the people who actually experience it  all the time.

So, of course product understands the customers experience inside and out and all of the dependencies in the product. Our product is 20 years old, but it still doesn't mean that great ideas can't come from everywhere. So, instead of  treating the product team sort of as this holier-than-thou, who knows  everything and is the only ones who can  make the decision; bringing everybody  else into the fold in an organized  fashion, as contributors, not drivers and  approvers, has really stepped changed the way that we even think about a roadmap. Also, making the roadmap for product managers is super stressful and no one I know like loves doing it, so it  always just feels like a promise that you can't keep and who wants to work against that every day? So, if we make smaller promises, that everyone's on board with, well have a better chance of keeping them, and learning from them faster and then adjusting our strategy.

To say that you know everything that's going to happen in a year for your business, doesn't even make sense. If you really step back and think about it, so many outside factors change what could happen in your business. I remember, after  the election a couple years ago, that you  know the Evite business went a little  weird and we could have never predicted  that, but when families weren't talking  to each other and were getting together that had very unexpected results on  our party business. I'm glad that America is coming out of it a little bit, it seems like, at least from the business end. It's like, what if we all kept going in the way that we were and didn't adjust?

So, if you're  going to be agile in product management, and you're saying, “Well we're going to  learn in the way that we work all the  time” and say, “Well we want to listen to customers all the time and we’ll adapt” it's like, then why are you  going to set something permanent for a year?

Hope Gurion: Do you think you could have that philosophy without your CEOs buy in?

Lauren Antonelli: No, no, I don't. I'm not sure how that would work. At least, when I talk to people at much bigger companies, people from the councils, it's really hard to up-level prioritization unless that top level is on board with it.

Hope Gurion: Now, Brandon Anderson of Sports Engine shares why his roadmap is never more than six months out and that ultimately with autonomous product teams, roadmaps become unnecessary. 

Brandon Anderson: Don't illustrate like a confidence level in a document that I send out to folks. By the time we've gone through the iterations of putting together a six-month road - we started with a year roadmap, then I got it down to nine months, still not confident enough, got it down to six months. So, we just kind of basically say what's in the roadmap is subject to change. We're very much on a journey to fully autonomous teams, so I push product managers to be the ones that are filling our queues up from the big strategic point of view. You're of course,  going to get top-down stuff, changes in business; we acquire a lot of companies  in our area and so that happens to us, but what's in our control, we're really trying to push and we're trying to get the teams to be autonomous.  So, I'm actually over time trying to become less reliant on roadmaps, and more reliant on these kinds of face-to-face communications. Being the thought leaders in your space, where nobody really challenges what you're doing next. You're in such a good space with your product knowledge, that takes senior people, that takes years of experience on the teams and they have to be able to hit some big meaningful things. So, it's a hard journey, but it's worthwhile. 

Hope Gurion: Margaret Jastrebski shares how short-term roadmap items should have high levels of conviction, but further out you’re providing context to help the rest of the organization know what you’re thinking the future may hold.

Margaret Jastrebski: Of course, kind of my answer always comes down to, with anything the product, it comes down to ‘it depends’.  It is really kind of indicative I think, of the product role.  But, when I think about, what would I include in a roadmap and what what wouldn't I include, it's really, really important to share your level of conviction. I think of roadmap as, “This is our level of conviction, these are the things we want to do” and  so I think roadmaps, they're wide and  they're deep and they kind of represent what you think is going to happen  immediately you know 30, 60, 90, days. I  love that framework, 30, 60, 90; what do you  think is going to happen in the next 30,  days 60 days, 90 days? You could even do three months, six months, a year, but you get the format, you get the structure. If  the near-term stuff is the thing that I  have the things that I have immense amount of conviction on, this is the  stuff we know we can do, this is a stuff we know we need to do, this is the stuff  we know is really going to move the  business. The stuff that's farther out, is  the stuff that we're researching; the stuff that we're going to go to  market, we're going to go talk to users,  we're going to go talk to the clients,  the partnership, etcetera, and figure out, “Okay this is we have a strong  sense of, we think we want to do, but how  do we frame it out, how do we think about  it?” and then the stuff way far out, is the  stuff that I'm like, “Hmm, this is kind of  generally the dirt direction we're  trying to go, but there's a lot of  information that has to be figured out  between now and then” So, I  think about it as it's more of, here's  the conviction, and then here's kind of  the broader context in which your  conviction sits.

I think it's really  important to provide all of that  information, a lot of what the product  role is, the way I describe  it is the what, and the why;  so, Deb shows up with the how, but product shows up with the what and the why. So, your roadmap is the way of making that what and the why really articulated and really detailed so people can understand and follow what you're going to do. I think it  also grounds itself into the broader context of what you're trying to  accomplish for the organization, for the  business, what are the business outcomes for some metrics that you want to drive, what's the user experience you want to  drive. I think the ‘may happen’ component of that is really critical to include because it gives the person that's absorbing that roadmap, that's consuming that roadmap, a little bit more information around the edges. It gives that person more  information as to, “Okay, these are the must-haves that I see kind of what else my product person is thinking about” and  it gives them more context, to think a  little bit more broader about the problem they're trying to solve.

So, when I think about people that are using roadmaps, that are the users of roadmaps,  or the people that you're delivering to,  a lot of times it’s, or most of time you can kind of broadly say it's your organization, but really it's the dev  organization; a lot of times it’s who  are the people that are actually going  to run with this. Again, I think it's really important to give them the why, the context. A lot of times it's your senior leadership, so is it the senior leadership team, is it the CEO, head of sales, head of marketing etc.? So, they can see what you're thinking, and they can see what you're laying out in terms of what to execute. Then, finally,  I think it's really important to include that just because it heads off a lot of  questions, I find that as the product person you're the receptacle of  everybody's ideas and so if you can  actually articulate, “This is what we're  doing and this is what we may do” people  oftentimes see their ideas kind  of where they sit, in terms of commitment and they can see that “Okay well, Margaret, she's my product person, she's thinking about this, but  obviously it's something that she's going to need to think about more  or something that’s farther out. I'm a big fan, big proponent, of having a broader context view of a roadmap and not trying to slim it down to only have that very narrow view. I think you have to have the narrow view for the people that need that, but I do think you have to have kind of all the components,   

Hope Gurion: Surprise! You thought you were going to see five different roadmap examples, so you could choose the perfect one for your company, right? Not so fast. If we’ve learned one thing as product leaders, it’s that there is no one size fits all roadmap. In fact, it's really unlikely there's going to be a single document to answer every single question. 

Context is everything as you heard from these products leaders you need to ask certain questions of yourself before you can figure out what the right way is to present to your company what the product team is working on.

You need to understand who needs to know what to make which decisions that way you can tailor the right level of information to the people and think about exactly the right timeframe that makes sense, given the needs of your audience. 

You may be operating in an environment where there is a high need for certainty, perhaps because people haven't felt that there’s been a lot of follow-through or delivery around that the product team or because there's certain very, very critical short-term goals that must be met.

The higher the need for certainty the more likely that your roadmap is really going to be focused in the very very short term in the what WILL happen zone.

 I advise new product leaders to set the ground rules for engagement with their  leadership team and with their  organization so they can decide whether  it is a document that needs to be  produced or whether it is a conversation  that needs to be had with certain parts  of the organization  and to decide very consciously what is  the right level of fidelity to balance  the things that are highly certain in  the short term and nearly impossible to  predict in the long term.

I hope that the advice of these products leaders has been helpful to you as you think through what your roadmap should contain, and more importantly may be instead of a roadmap, we can align on outcome goals for our company and customers?

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You can find me, Hope Gurion, on Linkedin and Twitter or subscribe to “Fearless Product Leadership” on your favorite podcast platform to be notified of new episodes.  You will find transcripts, videos versions of each episode as well as more information on my Fearless Product coaching and consulting services by visiting my website, Fearless-Product.com.

Hope Gurion
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