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


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, Fearless Product: Roadmaps are a hot and enduring topic  amongst product leaders why because  everyone wants to see how everybody else  perhaps that magical document that helps  their organizations deal with short-term  and long-term planning needs I often  find that there are two problems that  cause confusion in organizations with  new product leaders first it's often  unclear who decided what was going to be  in the roadmap and how those decisions  were made and second there's often not a  distinction made between what will  happen and what may or may not happen so  in today's episode we're going to hear  from five product leaders about how  they've solved the roadmap puzzle in  their organizations.


Lucinda Newcomb, VP Discovery & Personalization, Walmart.com: 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  you know 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 you know we sell toilet paper like  we sell all these things what we sell is  not the actual product that I manage so  for me and I maybe it's different on the  other side but for me I've always looked  at this as my product or the customer  experiences that help you make decisions  and purchase items so with that in mind  that 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 you know lasting  you know 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 is 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  corridor after that I'm at 50%  confidence in the third corridor 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 and 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  we need to think about that one 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 the 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 and 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 but as  so 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 probe  that proposal but it always comes out to  and then tell me which of the things  that are already committed should come  out brick and brick out you can't throw  bricks in there without helping identify  what bricks you think should come out  and 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 and 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 hat let's all  together discuss how are we going to get  it right for the customer at the end of  the day and as long as you're always  focused on the customer is at the end of  the day going to be the most important  thing I'm delighting that customer it  helped squash a lot of the different  conversations in the room and helps lead  people to make better decisions but  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 and 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  like 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  as they here's the roadmap that is what  is the roadmap and you have a monthly  conversation Rimi 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 in  other forums it has to be here is where  everybody gets to come in and have an  equal voice and equal participation  doesn't mean they get an  we'll say cuz 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.


Stefan Radullian, Head of Product Management, Brainloop: The  roadmap that we create does not contain  what may happen we try to be as as  realistic and as a certain as possible  so what I what 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 and 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 that this is a very  complex system and schedule can change  anytime and a roadmap is a snapshot of  that schedule it's the best thing that  we so that 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 and I think so  if if we are committed to do to deliver  that kind of roadmap businesses so in a  mostly the best 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 it's people want  certainty and we try to deliver that  certainty with the roadmap or at least  reduce uncertainty a little bit yeah by  telling them look this is the most  probable plan.


Hope Gurion, Fearless Product: 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 you  - the weapon against its creators?


Stefan Radullian, Head of Product Management, Brainloop: So  there's one there's one little  improvement that was actually  significant for that we did in our  roadmap slides or the way we put it it  was when we 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 I  not very precise on the date but that's  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  uh and 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 and we remove the day  away from that that let us the  flexibility and then the freedom to find  short-term solutions the problems that  we are trying to solve.


Lauren Antonelli, Chief of Staff, Evite: 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 dying and there are five  people like why should they decide even  though it was very influenced by a CEO  and everything else and you know 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  box was contributing like well I don't  know why they made these decisions  what does impact does this have on the  business in five years in ten years  then I started thinking did we even  design the roadmap that it encouraged  that kind of stuff when you start to be  real about capacity you start to really  realize like you were only gonna 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 road  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 you know why  not you know we're lucky enough to have  a product that everyone in the company  uses you know online invitations are for  everyone I mean we throw parties at  evite people are moms and dads people  have kids birthdays they have happy  hours and bridal showers and 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 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 it 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  and also making the roadmap for product  managers is super stressful and no one  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  gonna 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 your app could  happen in your business remember after  the election a couple years ago that you  know the eBay business went a little  weird and we could have never predicted  that but when families weren't talking  to each other and we're getting together  that had a very unexpected results on  our party business you know and I'm glad  that America is coming out of it a  little bit it seems like at least from  the businessman well it's like what if  we all kept going in the way that we you  know and didn't adjust so if you're  going to be agile and 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  well adapt it's like then why are you  going to set something permanent for a  year.


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

Lauren Antonelli, Chief of Staff, Evite: 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  counsel's it's really hard to uplevel  prioritization unless that top level is  on board with it.


Brandon Anderson, VP of Product, SportsEngine:  I don't illustrate like a confidence level  in a document that I send out to folks  right it's like 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 for six months and 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 right so I push product  managers to be the ones that are filling  our queues up from the big strategic  point of view right 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 the  like happens to us but what's inner  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 right  and more reliant on these kind of  face-to-face communication being the  being really the thought leaders in your  space where 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 right so  it's a hard journey but it's worthwhile.


Margaret Jastrebski, Product & Strategy Advisor:  Of course kind of my answer always comes  down to with anything the product that  comes down to it depends  oops you know is a really kind of  indicative I think it's a product role  but when I think about like 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 like I think of roadmap says  this was our level of conviction because  these are the things we want to do and  so I think roadmaps are 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 right  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 is this this this 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 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 and so you know 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 says I think it's really  important to provide all of that  information a lot of what the product  role is is yeah I but the way I describe  it is the what no why  so Deb shows up with the how but product  shows up with the what why and so your  roadmap is is  the way of making that that what and the  why really articulated and really  detailed so people can understand follow  what you're going to do but 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 and so I think them 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  you it gives that person more  information as to okay these are the  must-haves that I see kind of what out  my product person is thinking about and  it gives them more context I 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 roadmap  or the people that you're delivering to  a lot of times it for most of time areas  you can kind of broadly say it's your  organization but really it's the dev  organization you know a lot of times who  are the people that are actually going  to run with this and 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 this between your leadership team  this is CEO sales at a marketing etc so  they can see what you're thinking and  they can see what you're laying out in  terms of what executes and 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 you know kind  of where they sit in terms of commitment  and they can see that okay well you know  Margaret she's a treatment product  person she's thinking about this but  obviously you know it's something that  she's going to need to think about more  or something at farther out um so 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 so the people  that need that but I do think you have  to have kind of all the components.


Hope Gurion, Fearless Product:  Surprise!  you thought you were gonna see five  different roadmap examples so you could  choose the perfect one for your company  right? not so fast. there really is no  perfect roadmap and 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 is the right way to  present to your company what the product  team is working on you need to  understand things like:

·      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 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 are  critical to meet the higher the need for  certainty the more likely that your  roadmap is really going to be focused in  the very very short term

·      I advise new  products leaders to set the ground rules  the 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 organism  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, do you actually need a  roadmap? 



Hope Gurion