Decision Making Amid Uncertainty: Ditch Your Product Roadmap Before It’s Too Late 🚮🔮⏳ – Guest Blog Post

Written by Published in Product Management

A map acts as a guide with various routes to get you to your destination, but it doesn’t tell you where to go. That’s for you to decide. The main value of the map is that your awareness of the landscape dramatically increases your options. 📸: delfi de la Rua

During times of uncertainty such as this COVID-19 pandemic, which arrived at overwhelming speed and enormous scale, product leaders face a potentially paralyzing volume of big-bet decisions. Decision making amid uncertainty is not easy. Product leaders cannot afford to wait when events are moving as fast as they are right now.

At CareGuide, our product-led approach has enabled us to be quick to adapt to changes, evolve our product, and advance our business strategies to stay a step ahead of our customers. CareGuide is a portfolio of online marketplaces and our mission is to pair families and individuals with great care providers. Due to the COVID-19 outbreak, we soon learned that many parents are struggling to find a balance between working from home, caring for their children, and educating them. So, we quickly built a new experience for our CanadianNanny and Sitter community to empower nannies and babysitters to offer remote babysitting and tutoring.


CareGuide Product


Right now, dual working families are struggling to keep up with work and homeschooling, and even an hour of time to themselves could be what keeps them sane. Additionally, multiple families could share one sitter during these remote sessions with both children and the sitter from their own homes. This will save families some money, make sitters more money, and will make it more fun for the kids.

Most people wonder how we are always so quick to adapt to changes, evolve our product, and advance our business strategies to stay a step ahead of our customers. Interestingly, most assume that our effectiveness starts with a solid product roadmap.

Well, it doesn’t.

In fact, we don’t even have a roadmap.

That might sound risky at first, but the common objections to adopting a more flexible approach to product development aren’t that hard to refute.

But everyone else is doing it…

According to conventional wisdom, the first thing every CEO or product leader must do is create a product roadmap — a relatively static document that maps out the vision and direction of your product offering over time. It’s a guiding strategic document as well as a plan for executing those strategies.

Before the rise of agile development methods, the product roadmap underwent much less fluctuation during the product’s lifetime. In fact, depending on the organization, a roadmap’s time frame might be locked in for 18 months or longer. In my discussions with CEOs and product leaders on product roadmaps, most conversations revolve around a timeline view of which new features are going to get added when. At the end of these discussions, I frequently find myself asking: how do you know what features you should focus on six months from now? Product roadmaps rarely survive first contact with customers. As the boxer Mike Tyson once said about his opponents’ pre-fight strategies: “Everybody has a plan until they get punched in the mouth.”

Product roadmaps are as outdated as business plans, but at least business plans have already been disrupted by the lean startup methodology — which favours experimentation over elaborate planning, customer feedback over intuition, and iterative design over traditional “big design up front” development. Lean startup concepts , like minimum viable product and pivoting have quickly taken root in the business world. Companies of all kinds are attempting to improve their chances of success by following lean startup’s principles of failing fast and continually learning. And despite “startup” being in its name, some of its biggest payoffs are gained by the large companies that embrace lean startup.

In today’s world of product development, you need to be lean and adaptive if you want to delight your customers. It’s easy to see features as a numbers game: more features leads to more adoption and therefore more revenue. The hard truth is that there is barely any correlation between the total number of features offered and product adoption — successful features are what matter. That means finding the features that really matter to your customers and focus on delivering those. To do that requires flexibility. The last thing you need is to lock yourself into a roadmap. Widespread market needs can develop at any time, so how do you adapt when you’ve got your next 12 months locked in?

But our stakeholders need timelines…

Of course, investors, sales teams, customer success teams, marketing teams, customers and prospects need to know when things are going to happen. But instead of making promises based on when things are going to be pushed in the future, let your stakeholders’ feedback tell you how to prioritize your backlog. Clearly, this is a cultural, systematic, all-encompassing change for some companies. But if your company isn’t embracing uncertainty, a company without a product roadmap will.

But what if we just have a flexible, internal roadmap…

There are many ways to overcommit. You can share future functionality with the public too early. You can promise to deliver something to a customer by a specific date. You can overreact to something competitors are doing. Internal roadmaps can run the same risk.

After decades of watching companies fall prey to overcommitment, Steve Blank eloquently points this out in his Harvard Business Review article:

1. No one besides venture capitalists and the late Soviet Union requires long-term plans to forecast complete unknowns. These plans are generally fiction, and dreaming them up is almost always a waste of time.

2. Product roadmaps and business plans rarely survive first contact with customers.

3. Startups are not smaller versions of large companies. They do not unfold in accordance with master plans. The ones that ultimately succeed embrace failure while adapting, iterating on, and improving their initial ideas as they continually learn from customers.

At every company I either worked at or worked with, I kept seeing “internal” product roadmaps with quarter-by-quarter feature breakdowns — they typically covered the next 1–2 years. And sadly, these product roadmaps go out-of-date almost immediately because knowledge is constantly gained from market analysis and interaction with customers.

The problem with even internal roadmaps is the expectations game. People expect you to deliver what you say you will in 5–6 months, but what if you have a better idea two months in? What if there’s a shift in the market you need to address? What if all your assumptions were wrong?

Any change in the roadmap nullifies the roadmap. Then the map isn’t a map at all.

Product roadmaps are dangerous, even if they’re only shared internally. They often put you on the wrong path. When you let a product roadmap guide you, you let the past drive the future. The future should drive the future. Roadmaps effectively say “six months ago I knew what six months from now is going to look like.” They say “I’m not going to pay attention to now, I’m going to pay attention to then.”

That’s why we ditched our product roadmap.

Meanwhile, you should always default to full transparency in how you are designing your product and building new features. At CareGuide, every Thursday afternoon, we host a company-wide meeting to share a recap of what happened over the week with the entire company. It can include anything from new features we are currently designing to discussing our product strategies. We never wait till we’re fully done with a project before we share the outcomes with the rest of the company. We demo early, we demo often.

But we need a long-term vision…

You sure do. Having a product roadmap and a long-term vision should be mutually exclusive. Instead of building a product roadmap of what you’re going to build during the next 18–24 months, you should focus on tuning your long-term vision and strategy to predict the future. Look into your competitive landscape, the future of your product, and STEEP (Social, Technological, Economic, Ecological and Political) implications of the future you are envisioning.

Just make sure you always have an inspiring, impeccable vision for your product. When your engineers are inspired, they aren’t thinking about the final end-state of your product. When people feel inspired, they often don’t need external motivation to move forward, the feeling of purpose and meaning is enough to propel them.

Those without a clear vision, mission, or purpose often require lots of external motivation to keep moving forward. Those that operate and live from a place of purpose are inspired every day to give 100%. They may get tired, but they can reach back to their higher purpose to be inspired. This is why the most effective product leaders are the most inspired leaders — and the most inspirational. And you definitely don’t need a roadmap to inspire your team. Sell them your vision.

Almost every company understands that it needs to deal with ever-increasing external threats by continually innovating. To ensure their survival and growth, companies need to adapt to change. Building a business and products means evolving over time, not taking blind leaps. You can’t just jump to the next stage or the next feature, you would need to get back to what you have missed.

How we manage our product development process

At CareGuide, before the beginning of each quarter, we start our discussion by revisiting and reinforcing our company’s overall product strategy as well as our vision for each of our product teams. We, then, ask ourselves where we want our product and business to be in three months, how the end of the quarter should look like, what outcomes we should aim for, and which business problems we want to solve by the end of the quarter. We are initially more concerned with the wider, macro system as a whole. We avoid specific individual components of a systematic operation, focusing on the details of rudimentary micro functions — we are less concerned with individual components within the system and how they operate.

Once we finalize the business problems we need to solve by the end of the quarter, we start working on our OKRs (Objectives and Key Results). OKR is a framework derived from a management technique called Management by Objectives, a term coined by Peter Drucker in his book The Practice of Management. Management by Objectives is a process that requires the identification and accurate description of goals to achieve with deadlines for completion and monitoring. This process requires that those involved agree with what you want to achieve and that all play their roles for the achievement of the objectives. I don’t get into the weeds with OKRs as there are tons of great online resources on this topic. Just remember that setting the right OKRs establishes the tone for the quarter- which can be the difference between a chaotic quarter and a coherent one.

Setting the right OKRs establishes the tone for the quarter — which can be the difference between a chaotic quarter and a coherent one.

So, take your time and run your OKRs by all the other teams at your company. At CareGuide, I hold quarterly product strategy meetings for our leadership team to walk them through our OKRs. This meeting is essentially a board meeting for our product and we clinically examine our product OKRs for the quarter to make sure we are making the right decisions as a team.

A strong set of OKRs enables us to plan our quarter and monthly milestones accordingly. Instead of a product roadmap, we just look out a few weeks at a time and we always work on the next most important thing. What’s the point of a long list when you can’t work on everything at once anyway? Finish what’s important now and then figure out what’s important next-one step at a time. This doesn’t mean you can’t have ideas of where you think your product should go or future features you’d like to implement. This doesn’t mean you shouldn’t have a vision. We have the most visionary founders I’ve ever met in my life. What it means is that you need to pay attention to reality. Reality is where you’ll find the best answers. And you’re never closer to reality than right now. The further you get from now, the less you know. And the less you know, the worse your decisions will be.

Closing Thoughts

All these things sound good in principle, but it’s not easy to do it in practice. Even though it took us some time to get where we are today, this approach has worked like a charm for us at CareGuide — it has enabled us to innovate and deliver on unanticipated, future needs. Try it. It’s liberating and certainly more satisfying than following a plan you know is outdated. And after you try it, share your results with me. Can’t wait to see what you do with it 🙂

This article was originally published on

About the Author:

Amin Bashi is VP Product at CareGuide. CareGuide is a portfolio of online marketplaces and their mission is to pair families and individuals with great care providers. CareGuide’s portfolio consists of, and Prior to CareGuide, Amin was leading the product and design teams at CrowdRiff. CrowdRiff is an AI-powered visual content marketing platform used by the world’s best travel and tourism brands such as Zürich Tourism. Before joining CrowdRiff, Amin led the product innovation team at Financeit powering over 7,800 merchants and $3 billion in payment plan applications. Amin also led “Shopify for Startups” program and worked with Shopify’s business and engineering teams to build a world-class developer ecosystem. He worked with 400+ app partners all around the world to help them build their products and grow their businesses strategically. Amin is currently a Senior Lecturer at Product School, and he’s training the next generation of product leaders in Canada.

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