Roadmap Shortcomings with Scale Ups? Here’s an Adaptable Product Solution

Stephen Carrey-Chan
8 min readMay 16, 2022
Business Process Incubator’s take on Geoffrey A. Moore’s “Crossing the Chasm”

You’ve read your Marty Cagan books, attended some #ProductCon conferences and even completed some Product Management courses with Product School. Now you’re ready to take these philosophies and frameworks back to your company and put them into practice so you can unlock the true power of empowered product teams. You shop your proposal on moving away from ‘feature teams’ around with your product leaders and closest execs, getting positive buy-in. Your cross-functional pod (PM, Design, Engineering) marches into next quarter’s planning period with an aligned focus to prioritize activating a new growth channel, captured in an outcomes-based product roadmap with plenty of budgeted time to conduct rapid, lean experimentation that’ll inform future direction. And that’s when the first rain drop falls before it pours…

Roadmap tornado warning signs

The General Manager mandates a key business metric in need of immediate attention as the company #1 priority. This new priority demands your team’s full attention to execute properly. There goes month #1… Next, some tech debt disrupts the typical business as usual and results in late night hours to rectify. Bye bye, month #2… It’s month #3, and your team is hopeful to resume the initially planned growth project. Suddenly, another team with a high visibility initiative says it’s blocked by some dependencies on your team and the new executive who joined the company has new, different priorities — which you agree to.

As you wrap up these unplanned pivots at the turn of a new quarter, the Board expresses disappointment in the lack of growth progress and prescribed solutions start trickling top-down to your team’s plate to execute upon next quarter. At this point, the last thing your team feels is ‘empowered’.

Roadmap disruptions product team journey from Stephen Carrey-Chan

“I thought we were the growth pod. Why did we get stuck doing retention work when we have a dedicated retention pod? This seems to happen every quarter, yet our pod is somehow expected to support retention and security priorities while maintaining steady growth progress?” Identity crises and senses of betrayal festering, you revisit your Now-Next-Later roadmap, which was supposed to buy your team the time to make at least some demonstrable progress towards your “Now” priorities. And its problems-based emphasis was supposed to minimize prescribed solutions from stakeholders. How did this happen?

Learning to play in the tornado

The reality is that this is very common for product teams at scale ups that are crossing the chasm to expand their customer base. I personally find the majority of product books and courses failing to effectively train product managers and teams on how to grapple with these complex environments. Your company is at the stage where it must demonstrate hyper growth to prospective and existing investors while somehow also take risks at innovation to stay ahead of competition and ready itself to scale by reducing tech debt that was necessary to achieve product-market fit.

Strikedeck’s diagram on Geoffrey A. Moore’s “Crossing the Chasm”

If you‘re joining a scale up, best to not assume the perfect product environment has been carved out for you to act upon your contemporary product management learnings. That type of environment requires an incredible amount of trust between Product and Leadership, predicated on the product team’s credibility and track record of consistently delivering strong results. So as trust gets cultivated over time, what can you do now to maintain a sense of control in the land of unplanned pivots?

Enter: Value Streams Roadmapping

The official name is definitely a work in progress, but — in the spirit of agile development — I’d like to share what we’re currently dubbing the value stream roadmap and hear your feedback. This new roadmap framework is the latest result from numerous white-boarding sessions and specifically aimed at enabling product teams to effectively operate in an ever-changing, complex business environment.

How the value streams roadmap works

The purpose of the value stream roadmap is to visualize your product roadmap as a portfolio of long-term goals, sequential tactics, and use of resources. We took inspiration from a user process flow to place our cross-functional pods and key stakeholders in the same strategic, war-gaming seat together.

Define your North Stars

Each value stream needs an ambitious, inspiring and impactful North Star to work towards in the long run. It’s not uncommon for Leadership to also have major, cross-departmental strategic initiatives (e.g. introduce the company’s first-ever, in-house fulfillment center) to complement the company-level objectives & key results (OKRs) to focus and align all teams. It’s these major initiatives that help the Board and investors better understand how the company plans to achieve its business goals, and they often make for great North Stars. If you don’t have company initiatives to leverage, your North Stars can be major thematic opportunity areas coming out of your product strategy work. The point is to try to align your board members and investors behind the same long-term North Star achievements that compel your product teams to bring their best to work every day. Truly shared visions will help to keep all parties committed towards the same long-term goals, adapting and evolving individual North Stars as needed.

Break down a value stream into thematic wins

Working backwards from the North Star, take your best first stab at breaking down a value stream into thematic wins to represent significant chunks of work to place business bets. A thematic win — like establishing some major prerequisite foundation for a new business model — should be unlock significant added value for the business and is the highest level of thinking about sequential wins. This aspect isn’t much different from typical product initiatives roadmaps.

Sequential milestones and “moments that matter”

Within your earliest thematic wins, identify the subsequent milestones and moments that matter that help to bring that win closer to realization. Milestones should reflect the discovery work and release chunks from the involved product teams. We start to see the diversion from typical product roadmaps with the addition of ‘moments that matter’. Moments that matter can be major anticipated decision (go/no go?) and learning checkpoints (did it work as intended?), and showing the different paths a product team can take in response to stakeholder decision-making or learning outcomes of that checkpoint.

Next, explicitly call out the dedicated cross-functional pods assigned to that value stream and its subsequent theme. Ideally, these pods are in it for the long-run with this value stream to build up subject matter expertise and strategic chops. However, in a scale up stage where priorities can change frequently, product leadership can’t predict the perfect allocation of resources to meet unplanned business needs, so PMs should be prepared to adapt to priority changes and shift value streams as needed.

As the business encounters unplanned changes, Product Leadership can refer to the value streams roadmap to focus discussions around bets and trade-offs. If something unexpectedly bubbles up as a critical priority and demands remediation ASAP, teams can visually capture the reallocation of resources across value streams. By showing the removal of team resources from one value stream to another, this reinforces the business’s understanding that everything comes at a cost, that investing more teams into Value Stream B will slow down progress with Value Stream A.

Leadership decides to re-prioritize Value Stream #2 over #1.

A portfolio of risks and rewards

The additional visualizations of ‘moments that matter’ and team budgeting is an important shift for key reasons.

  1. This encourages product teams to think ahead for their possible futures within a value stream, helping them to better identify risks and unknowns and seek mitigation tactics. The possibility of shifting value streams also requires that PMs and teams stay flexible and mentally prepared for change in order to achieve the best company outcomes.
  2. Gantt roadmaps often have a standalone initiative for a defined period of time (ie. iOS app), which conditions maintainers and audiences of an expected state of “Done” and stay output-focused. Value streams reinforce a mindset of ongoing, continuous work required to be successful in a focused area, helping to reduce the focus on delivering a functional feature and more on the outcomes-based journey.
  3. This establishes an upfront stakeholder awareness and acknowledgement of potential subsequent product work that will be dependent on outcomes that teams can’t predict now, ultimately realizing the longer-term commitment of pursuing a specific value stream.
  4. Moments that matter elevates key learning goals as first-class entities in the product roadmap, coupled with their subsequent iteration work based on insights and learnings. Typical product roadmaps must find ways to differentiate learning goals from aspirational deliverables to manage clear stakeholder expectations with product releases.
  5. The North Star of a value stream is a mission pitch to the executing product teams that supersedes the short-term payoffs of individual milestones that may be less interesting or exciting as standalone. If your team is tasked with some regulatory compliance milestones and compliance is just not your passion, the value stream reminds you of the bigger picture (ie. realize the new business model) and celebrates these milestones as meaningful incremental wins towards the end game.
  6. This framework speaks the CEO and CFO’s investing language. The value streams represent a portfolio of funds, taking on risk by putting capital (product resources) to work to achieve higher returns. Considering pivots to unplanned priorities becomes a conversation around risk and reward and whether to deploy additional capital out of one fund into another.
Original diagram from Stephen Carrey-Chan

Putting the roadmap into action

While in its nascent, proof-of-concept stages, this framework has been resonating with product teams, stakeholders and execs. Without a scalable, dynamic solution that adapts to pod-level changes in real time, this roadmap requires ongoing maintenance across the teams to accurately reflect the product portfolio of risks and rewards and inform trade-off decision-making.

Value streams can easily span multiple teams due to the ambition of thematic wins. To help streamline work, I recommend determining an assigned, dedicated leader for each thematic win— the “R” in the RACI model to determine the sequential initiative milestones and KPIs within that theme and act as the ultimate decision-maker. Without that single-threaded leader, you increase the risk of ambiguity and siloed information.

If you’re struggling with the perpetual storm of unplanned priority pivots in the high-velocity scale up world, I very much welcome you to try out this planning framework throughout your next planning period. Like a Beta group of customers testing an evolving product, please let me know how it goes and any feedback you have on how to improve this roadmapping framework for scale ups and any organization facing unpredictable change. Best of luck!

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Stephen Carrey-Chan

Director of Product, Growth @ The New York Times Wirecutter || +12 years in product management experience