Product managers, what's the hardest thing about creating your roadmap?

Sam Roberts Atlassian Team Jun 28, 2018

Hey community, my name is Sam from Atlassian and I'm a designer on the Portfolio for Jira team. Our team has seen that no two roadmaps look the same and come in many different shapes and sizes. Getting stakeholder buy-in, making tough prioritisation decisions, and turning those plans into actions is a huge challenge and it can feel like there's no "right way" to do it. 

We'd love to hear from you. How are you dealing with some of these challenges at the moment? What are the things you've found have made it easier to communicate and collaborate on roadmaps?

We're hoping this discussion will give us insights that we can use to improve our products such as Jira , and Portfolio for Jira. Also, if you're interested in having a more in-depth or private discussion with us about this topic, you can email us at: portfolio-feedback [at] atlassian [dot] com

16 comments

Jack Brickey Community Champion Jul 02, 2018

Sam, are you looking at how we use Atlassian products for documenting roadmaps or more broadly how we deal w/ making roadmap decision and how we document them? I haven't used Portfolio so can't speak to whether it would work for me or not TBH. I have never really leverage Atlassian products for road mapping in the past but have always wanted an integrated solution. I briefly looked at Portfolio while at Summit last year but haven't progressed that idea TBH. I'm happy to share my thoughts if you are looking for input from those not using Atlassian tools for the process.

Sam Roberts Atlassian Team Jul 02, 2018

@Jack Brickey, we're interested to learn more about things like:

  • Like you mentioned, how roadmapping decisions are documented
  • How are you sharing and communicating those roadmaps, what do they look like? Why does/doesn't that work well?
  • Do those roadmaps look the same throughout your company?
  • What's the most frustrating part of your current process? 

Whether Atlassian tools are used or not doesn't mater so much for this. If you use a spreadsheet, or even a whiteboard that's still things we're interested in learning about why that works. Because sometimes, those basic solutions can work well. Thanks.

Jack Brickey Community Champion Jul 05, 2018

Sam, sorry for delay in getting back. Here is some input from my current and past road-mapping activities.

  • I have used all sorts of tools as part of our roadmap exercise but all most all ended up in Powerpoint. This is primarily because of the audience: Sales, executives, PLM, customer all of which often live in the world of presentations. What this means is that any tool needs to be able to present roadmaps in some form of presentation mode.
  • In some companies we would version control our roadmaps and changes would have to be signed-off. While this might be considered old-school, if a roadmap is committed, especially externally, then it will be important.
  • I have used Confluence most recently to plan and communicate roadmaps.
  • We have used Voting on stories in Jira to help focus our roadmap discussions. I am a big believer that vested parties need some means of collecting input on what we should work on next. Having a solution where each vested party can stack rank a list of stories and then produce a tallied result would be helpful. I have used excel in the past for this.
  • One of the biggest challenges w/o a solid tool is that changes are constant and  so old roadmaps that have been sent around become problematic. Paper roadmaps are a bad thing.
  • The ability to show history on roadmaps is important.
  • Communication of "committed" changes need instantaneous communication and that communication often needs to reflect the why as changes understandably drive Sales and others crazy.
  • The most frustrating part is churn. No tool/process is going to eliminate that nor should it. The tool/process needs to address all of the ancillary issues that result from change: illustrate drivers and justification, capture discussions & decisions, communication of changes.
  • Timelines are understandably a big challenge because it is nearly impossible to have a good understanding of when something can be delivered until well after roadmaps are created. Personally, i'm not a big fan of committing any timeline until the development team is fully allocated and even then they should be provided only for the most immediate releases. For this reason I like to employee terms like: Planning - Draft - Target - Committed on a release by release basis.
  • Similar to Agile development the roadmap team needs the ability to feed results back into their process. They need to be able to assess how effective the team is at achieving commitments to improve on past over/under-commmiting scenarios.
Like 1 person likes this

Some things that would be nice in Portfolio.

1) Being able to bring in more than 5000 issues - I know programmes are coming but don't yet know how they work as we're on the cloud version.

2) Flexible hierarchy; both parent linking to issues higher on the hierarchy (eg user story to initiative) and having multiple hierarchies to support different business units

3) Legends on the charts for scope, schedule and themes.  With clear statements about where the source data comes from.

4) Clearer 'hints' at where constraints are moving items on the schedules

5) Percentage of teams/peoples efforts against initiatives - not just the remaining capacity

6) A consistent edit/view screen for issues as Jira has

+ Ability to see a historical view of work completed based on initiative with linked hierarchy and estimates so early high level planning can have some chance of being in the right ball park

Sam Roberts Atlassian Team Jul 05, 2018

Hey @Steven Dodd,

Thanks for joining in on the discussion. For the topics we're trying to learn about most, I'd be interested to dive deeper into #3, #4, #5. The other issues are important too, but might not match the topic theme of this. When it comes to sharing your roadmap at the moment. 

  • What are the top things you're trying to communicate?
  • How do you like to present it (e.g. powerpoint, images, documents, emails, etc)?

Hiya,

The top things I am trying to communicate are:

1) What we are going to deliver looking forward

2) How much it will cost

3) The ability to drill down in to it - epics

4) The other stuff that we also put work into but is not directly delivering the agreed business value

5) How much effort individuals and teams spent on each initiative

6) I am happy to present directly from portfolio and am not too fused about the medium although the senior executives in my current organisation like power points which are highly customised and the information coming from Portfolio is only a subsection of that information.

It all boils down to ensure we can align future and historically delivered business value to agreed budget.

Sam Roberts Atlassian Team Jul 16, 2018

@Steven Dodd those are all great insights. Is this something that happens weekly, quarterly, annually? How often are you doing these kinds of presentations?

Live data is always best - I would rather they could self help if possible.  Less presentations and meetings are always desirable.   The data coming from Jira populates weekly, monthly and quarterly reporting.

Jack Brickey Community Champion Jul 17, 2018

@Steven Dodd, couldn't agree more. The worse thing about roadmaps is that as soon as they go on paper they are out of date.

+1 On this point. Any road map that is disconnected from my data in a tool like Jira is immediately obsolete. It's a real pain to manage and update these manually.

@Sam Roberts I my experience as a Product Manager, the best tool I've used is Product Plan. It always for flexible date ranges (unlike Portfolio which is based on estimates). You can also add things like links to scope docs, comments, resources, and feature grouping.

But at the very minimum, the helpful thing is being able to add a feature as a horizontal block, and then manipulate the length and location of that block horizontally across a defined timeline.

I would also add that it's essential to be able to share the roadmap as a private link without requiring a user login. Not all teams (especially C-Levels) have access to or know how to use the Atlassian products. So any roadmap tool needs to allow a user to share the roadmap to anyone via a link.

Sam Roberts Atlassian Team Jul 08, 2018

@Josh Carter so after you've added a few features as horizontal blocks and moved them around on the timeline, I can imagine there'd be various secondary pieces of information that you'd want to bring along with that.

Lets just say you've got all these bars laid out and they are all grey and in a list, I'm guessing that probably wouldn't be enough for meaningful discussion. What are the other things that you'd like to include, and why would you say those things are must-have? 

The hardest (most time consuming) part about building out a roadmap that will be used to communicate UP (C-Level) is the flexibility of features (epics or projects). While Portfolio does a good job of creating a roadmap based on Epics and Stories, it uses story estimates to determine the timeline, which means it's not flexible.

You're right that a bunch of grey boxes isn't all that helpful. So the ability to change their colors, create a legend, and group them would be great.

One last thing, while not essential, but the ability to attach information to each block would be helpful. It's not essential because most Execs won't take the time to dive deeper into the weeds. Usually they just want a high level.

Another helpful thing might be a list of "What Didn't Make It". Product Plan calls this the Parking Lot. But just to tell the story of resource management and trade offs made.

Sam Roberts Atlassian Team Jul 09, 2018

@Josh Carter when it comes to "change their colours" and "group them", what are the ways you're wanting to do this?

Absolutely agree with the above thread regarding only using estimates for the timeline of the road map - it is a real challenge. It's a nice first look but not the ultimate schedule.

One of our biggest challenges is bringing in several 'solutions', each with thousands of Initiatives, Features, and Epics.  It becomes difficult to properly estimate the hours and that skews the roadmap projections. We have been trying to standardize our estimation since the company uses mixed methodologies of SCRUM and Kanban and both estimate differently. 

On top of that, the executive management likes 'old school' presentations as indicated above, but again challenging when the road map is an enterprise event and not just a small sunset of projects. 

A roadmap is only as good as its prioritization

Prioritization is only as good as the ratio of benefit vs. cost

Ratio is only as good as estimation accuracy

Accuracy is only as good as known factors

Known factors are sometimes limited

Therefore: gathering, sorting, and evaluating information prior to roadmapping is most critical. The difficult part has to do with time constraints. Documenting everything isn't viable, and not everyone uses the same tech stack in a large organization. Therefore, balancing time vs. research vs. Communication is the most difficult aspect.

Finding better methods/tools to quickly and accurately identify, evaluate, contextualize and share known factors is critical.

Sam Roberts Atlassian Team Aug 03, 2018

Well said @Brian Pohuski, a roadmap is only as good as its prioritisation. I think If you're solving the wrong problem for your customers, it doesn't matter how good you are at executing it. Its definitely very messy to make those trade-off decisions. Is there anything in particular you've found effective?

Not putting anything important along the creases ..

@Sam Roberts Roadmaps are always tricky as they mean different things to different people. 

Clearly, talking to people helps to build and shape the roadmap, but as others here are showing, Exec teams prefer PowerPoint. 

I’ve recently used an interactive Visio diagram linked to SharePoint pages and this has had very good feedback from end users. They have the high level detail in the visual, but more detail on the linked pages. This was done because the previous PPT route just wasn’t engaging enough and people just saw a Gantt chart and we’re turned off. 

As has been noted, this is all extra effort as the majority of our work is planned and executed in JIRA as we use it for Development and IT Operations who also run sprints. 

One absolute critical element for me is accessibility. Roadmaps are great visual tools, but very rarely can they be navigated by a screen reader in any logical manner. 

Thats why we took the Visio / SharePoint route. Although visual there is a clear text / keyboard navigation for blind users. 

Sam Roberts Atlassian Team Aug 03, 2018

Great to hear about some success there, @Richard Billam! How has linking to an interactive version been received by stakeholders who are used to the more traditional formats? Are they comfortable in the tool?

As you can imagine the click through rate is pretty low. The Exec team have the high level view they’re used to and are comfortable the detail is there if they needed it. 

However, those that are accessing it love it. They have they detail they need without having to come and ask for it. We find making this information more accessible helps significantly with engagement and understanding. 

+1 for catering for accessibility! Did not know visio and sharepoint can do that. Are you able to share a little more on how that works? 

Being able to rank a story above an EPIC in Portfolio - I require to be able to show this within Portfolio, and the story will not always be assigned within an EPIC.

Sam Roberts Atlassian Team Aug 03, 2018

Hi @Sanjay Athwal, lets get in touch with the problem you're having. Could you create an issue at 

Server - https://jira.atlassian.com/projects/JPOSERVER

Cloud - https://jira.atlassian.com/projects/JPOCLOUD

So that others can vote and comment on this request. Try to leave as much detail as the scenario or problem you're facing, so we can understand it better.

Thanks,

Sam

The hardest thing about creating a Roadmap is bringing digital data to the analogue space of “Big room planning” as this form of planning is a social event. Most team and leadership are to tied to a digital tool overhaving shared space to frame and iterate on ideas. To visibly recognize the dependencies and out of sync ideas on a Roadmap.

Finally when all is said and done making the Roadmap relevant and having it linked to the work as it is being done. This allows reality to creep back in.

Completely second Tarang!

Roadmap strategy sessions are the big picture in an event / easy to digest format. At the same time being able to access the underpinning information quickly.

Technical dependencies, opportunity cost and all the other data needs to be available on demand. Our session toggle between Themes in the sense of a bunch of mostly independent epics and the actual epics, the latter usually come up when cost and dependencies are an issue.

~Mark

Pooja I'm New Here Aug 16, 2018

Hello, 

Most of the issues written here resonate with me. 

  • Sharing of a roadmap across teams
  • Changes in Prioritisation 
  • Moving modules across the roadmap should also show highlight impact on resource utilisation 
  • Simple presentation feature 

Hi,

Main whys for making roadmap:

High level product planning

- to ensure compliance towards strategy and product market fit

- to enlighten and support stakeholders (board, sales, customer success, stakeholders) 

- to keep team aligned and reflective on the direction after the next sprint

 

Main pains with roadmaps (apart from regular change):

Visualisation requires (Google) slide format to:

- show a (Horisontal) timeline view

- show 5-10 items including small text + image over 12 months time line

- flexibility to move stuff around and optimise for different stakeholders

- show on screen

 

Issues about slides: 

- Disconnected, so not possible to map epics into high level roadmap items. 

- Disconnected, so not possible to see completion rate of roadmap items 

 

/Anders

Speaking for our company we use a simple Excel file to handle our roadmpap.

After discussing the topics with the stakeholders and prioritizing we create epics and tasks within Jira.

We don't use Portfolio at the moment and never tested it, so I don't know if this could help us in integrating our roadmap better with Jira.

 

We also use Mindmaps (especially before we create an Excel) to group bigger topics and subtasks to discuss in our product management team.

@Jason Walther, is there a particular Mindmapping tool you leverage? Or is that analog as well?

@Douglas Wesney, we use Mindmanager, it's available for Windows and Mac. Some also use Freemind as a OpenSource Tool. 

Hi, not sure if your question @Sam Roberts relates in any way to the Roadmap (beta) view that I discovered today after creating a new Agile project in Jira Cloud but I was really positively surprised to see FINALLY a working roadmap view by Atlassian!

Even in it's current simplicity it would already offer significant benefits to my organization in which I've always answered repeatedly to the question "Does Jira show roadmaps" the same way: you can use some 3rd party things but they seem pretty expensive and many does not even work in Cloud.

On the other hand a big disappointment for me was when I found out that the Board view (with statuses) only shows Stories and it seems that I cannot influence the filter to show Epic's only - it would be so nice to follow the scheduling and prioritization from Roadmap and then the statuses from Board. It seemed to nicely sync the statuses that I created on Board also to Epic's on Roadmap - which was not so logical, since I believe that in many cases your Epic's would have different lifecycle than your stories.

My need would be to show / follow Epic's with management and perhaps then create only few stories for project managers.

Would you have anything to share about this feature's future plans?

I have an IT project management background and have worked primarily in Microsoft shops.  I joined a new company this summer that uses Jira and Confluence and have been coming up to speed on those tools (kudos to the great documentation on this site).  Jira is great for issue management and Agile development, but is limited in project management for larger efforts.  The company added Portfolio, as it’s needed to provide the type of hierarchical reporting the executive team would like to see.

For one-year and five-year roadmaps, I used Visio and PowerPoint at my last company and have used PowerPoint here for some presentations.  Swim Lanes keep track of the categorization by business area with key deliverables mapped in on the timeline.  Confluence offers good options for communicating Roadmaps, as the author can import various visuals.

Being able to keep track of changes with versioning or a good history is essential, as this company works with government mandated changes that take priority over planned efforts.  Even if we try to plan for regulation changes, there are always unexpected changes that crop up.  We must communicate them and keep track of the original roadmap planned to actual deliverables.

Hi,

In my company we use Portfolio to create roadmaps on two distinct axes:

- Project Roadmaps

- Team Roadmaps

Where Projects and Teams are n-n relationship. One team can work on several projects and one project can be done by several teams.

Then we use extensively Cross-Project Releases because a Release can span out on multiple Projects.

We have a hard time using Portfolio because, as it seems, we need to put everything in one big plan which makes it a nightmare to manage Cross-Releases as we have hundred of Releases to chose from and there's no easy way to select them.

We would rather use a Program with multiple Plans in them. But we are facing the following problems:

- Cross-Project Release cannot be used at Program level on another Plan from which they were created. 

- Shared Teams velocity can only be set within a Plan and not aggregated at Program level if we wanted to make a Plan per Project.

Any insight on how we could handle this?

Sam Roberts Atlassian Team Oct 11, 2018

Hi stephane.hoareau@sicpa.com,

Thanks for asking about Portfolio! However, it would probably be best to create a new community question about this. That way it will be more searchable for others in the future. 

This community discussion is more about challenges of creating roadmaps in general. 

Sorry if this is a bit annoying but I just want to make sure this doesn't get lost.

Thanks,

Sam

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