Roadmap challenges at startups vs. SMEs vs. enterprise

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Effective product roadmaps are often simple on the surface. The cleaner and clearer your visualization, the cleaner and clearer your organization’s sense of shared purpose.

But no matter how slick your final roadmap might look, the roadmapping process can be anything but straightforward. In fact, we talk about “roadmapping” as a skill because it requires such a tricky combination of research, planning and empathy. (And maybe some psychology and/or hypnosis?) To get really good at roadmapping, product managers can’t just show up to the final meeting. They must learn to navigate a whole smorgasbord of roadmap challenges.

Case in point: a few months back, the following tweet popped up in our mentions.

It is a punchy tagline! But more importantly, this tweet speaks to the exact reason our founders launched Roadmunk: to make it easier for PMs to quickly build well-designed roadmaps.

Roadmap challenges, however, go far beyond “it’s so annoying to build a roadmap in a spreadsheet or slides.” And the pain points can differ if you’re at a startup, SME or enterprise. With this fact in mind, we decided to take a holistic view of some of the roadmapping difficulties product managers encounter at different companies.

product roadmap challenges

Universal pain points

Some roadmap challenges are equally difficult, regardless of the size or maturity of your company or product.

Setting priorities. This is a biggie. What should actually go INTO the roadmap? When you have lots of ideas (and demands) swirling around, it’s difficult to identify which initiatives to tackle and which to sacrifice. Product managers often need to make “big bets”—meaning some smaller projects get the axe. Understanding the benefits and tradeoffs of these decisions is a central challenge not just for roadmapping, but for product management as a whole. Daniel Zacarias wrote an epic guide to product prioritization that outlines several excellent prioritization methods, including the Kano Method, Value vs. Cost and a popular technique from Airbnb’s Director of Product Ian McAllister.

Managing expectations. What product manager hasn’t struggled with this? Sales is hungry for features. Executives are wondering why the next release wasn’t released last week. When you arrive at a roadmap meeting, everyone at the table will be fretting over (and expecting) different things. Is this roadmap going to help me close a deal? How can I build excitement in the market? Am I going to have to go back to the board and say we missed a target? Executives can be especially demanding and/or unrealistic, which is why we wrote an extensive blog on managing execs in the roadmapping process.

Connecting data to the roadmap. Solid roadmaps are strongly rooted in both empirical and qualitative data that supports the direction of the strategy. Empirical data includes engagement stats, business growth metrics, and impact on your market or customers. Qualitative data includes more emotional—but equally essential—feedback from your customers. Data is crucial, but it’s not always easy to a) get your hands on it, and b) represent data explicitly in your roadmap. New PMs are often enthusiastic about talking to customers—then start making assumptions 6 months into their role. Maintaining that energy and curiosity is time-consuming… but critical.

Building roadmaps in legacy tools is a finicky, limiting time-suck.

How to structure your roadmap. Our roadmap should be on a timeline! No, it shouldn’t have no dates! No, it should be finger-painted onto the bathroom wall! We often encounter strain around the structure of the roadmap, especially as pressure from the market comes into conflict with the ethos behind agile. We believe this decision should be rooted in culture. If your company values deadlines, your roadmap should reflect that approach. If plans are more loosey-goosey, your roadmap should be, too. Of course, a PM can affect how that culture evolves. Our handy guide outlines 3 basic ways to create a product roadmap, depending on the stage of your product and your culture.

It’s annoying to actually build and share your roadmap. This goes back to the root of the problem we’re trying to solve here at Roadmunk. (And what that tweet was all about.) Building roadmaps in legacy tools is a finicky, limiting time-suck. Roadmaps should be living documents that foster transparency, but it’s very difficult to maintain that spirit without a collaborative dashboard where you can comment, update and view your plan from different angles. If this is a particular sticking point for your organization, check out our full list of features.

startup roadmap challenges

Startup challenges: dealing with uncertainty

In certain ways, roadmapping at a startup is much simpler than roadmapping at a bigger company. There’s just not as much detail to include. But that lack of certainty and structure introduces other key snags.

Resisting the urge to over-complicate things. Startup CEOs tend to be ambitious and operationally driven. They want to feel like they’re a big, multi-million dollar organization right off the bat—and with a roadmap to match. But including oodles of detail in your early days can actually be counter-productive: it focuses too much on “operations” and “plans” at a time when the focus should be your product. Also, it doesn’t leave the door open for enough adaptability. We recommend keeping your roadmap super-simple—it might just be a simple list of features—for as long as possible.


Accepting change (and guesswork). Not only should a startup roadmap be simple, it should be 100% subject to change. At this stage, roadmaps are often a “best guess” of where the market is going and how your product will fit into the landscape. Again, it can be difficult to know when to pivot off your plans. Having a strict roadmap can actually be dangerous for early companies, because it can psychologically commit you to the wrong direction. Big challenge for startup founders and PMs: not getting too married to what’s on the roadmap.

small and medium size enteprise roadmap challenges

SME challenges

As your company becomes more complex, so does your roadmap. And so do the challenges associated with roadmapping.

Simplifying complex strategies. For startups, a key challenge is not over-complicating things. But as departments expand and your company begins to tackle bigger initiatives, the roadmap needs to accommodate this new complexity. It’s at this stage that we generally recommend moving your roadmap onto some form of timeline. Finding a way to effectively visualize and communicate all the moving parts can be a head-spinning exercise. Our blog below outlines some startup-specific tactics.

The challenge for the roadmap champion is to deeply understand the mindset, progress and problems the product team is facing.

Understanding of your product team. At this stage, there’s probably more than one PM in the picture. The person who owns the roadmap might not be the same PM who’s writing stories or communicating regularly with the devs. So the challenge for the roadmap champion is to deeply understand the mindset, progress and problems the product team is facing. Are they resource-strapped? Are they having trouble communicating? Are they in trouble with the competition? Are projects delayed? The challenge: really understanding the internal struggles of the product team and being able to present and communicate that information in a meaningful way.

Knowing the voice of the customer better than anyone else. As we mentioned above, motivation to talk to customers often peters out. As a company grows and becomes more complex, product managers can get more removed from the central problem and the voice of the customer. Thing is, other departments don’t lose sight of the customer. Sales can easily derail the roadmap because they’re in is in constant communication with users, while marketing is tapped into the pulse of the community surrounding your market. If you show up to a roadmap meeting alienated from your customer and their interests, it will show. It should be a daily and conscious task to understand that landscape—or your roadmap will flop.

enterprise roadmap challenges

Enterprise challenges

Pretty much every SME roadmap challenge also applies to enterprise. But when a company reaches enterprise status, they also have some new wrenches to deflect.

Responding to market trends. Enterprise is big. Enterprise is slow. Enterprise can be committed to what’s working now—even if it’s not going to be working for much longer. In the enterprise sphere, product managers must be several steps ahead of the market. It takes a while to turn a big ship, and PMs should anticipate the extra lead time they’re going to need. And while every PM should be a world-class communicator, enterprise PMs need to be extra savvy when it comes to building stakeholder trust. Otherwise no one will listen—and your roadmap will soon be stuck in the past.

Would you rather be disrupted by yourself or someone else?

Disrupting yourself. Once you’re at enterprise level, you’ve pretty much “made it.” But you’re also vulnerable to the “next big thing.” Which begs the question: would you rather be disrupted by yourself or someone else? To avoid the latter fate, your roadmap can’t just add feature after feature onto your existing schtick. It’s crucial to think like Amazon and self-disrupt. At enterprise level, a product manager’s biggest challenge is to come up with innovative ways to evolve its own product—then convince everyone else to get on board. Instead of keeping the wheels in motion, your roadmap needs to lead you on an entirely new path.

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