Why You Need to Take Planning Your Roadmap Seriously (and How to Do It Efficiently)

December 30, 2020
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A key challenge for small businesses is to come up with a practical roadmap and maintain focus. When you’re just starting, it’s easy to get excited about business ideas and try a few different things without needing an actual roadmap, but how do you keep moving the needle, enabling fast decisions, stay profitable or grow the company when there’s always too much to do without having enough time to do choose what to do?

When I started my tech career, I gained instant access to how technology companies in silicon valley planned their roadmaps. I was fascinated by how much effort went into planning and making every part of the puzzle align with the company’s big mission. As I grew my tech career and sought new challenges, I became a product manager at Uber Headquarters in San Francisco during the company’s high-growth stage. In that role, I led the product efforts that solved core user problems and owned product roadmaps for features that were used by millions of users across the world.

I didn’t know this critical role at a billion-dollar company would be the best learning experience for my journey as an entrepreneur. Since leaving Uber, I have utilized all of that experience to launch my own products and turning them into big successes.

Roadmap planning has now become one of my favorite day-to-day conversations with other entrepreneurs, especially early-stage or early-growth companies. I know how easy it is to make roadmap planning way too complicated and potentially squeeze the fun of having a business or your company’s potential for significant results. No one wants that.

Here’s why you need to take planning your roadmap seriously and how to do it efficiently.

Tip #1: Gain Roadmap Clarity

To me, roadmap clarity is about having a well-thought-out vision, strategy, articulation of key metrics, and how you’re going to move them. Roadmap clarity also makes it very easy to say “no” to stuff, which is as important as saying “yes” to things. As entrepreneurs, we might feel like we can do anything, but we certainly can’t do everything, at least not all at the same time.

Tip #2: Consider Quarterly Roadmap Planning vs. Yearly Planning

I know yearly planning gets a lot of attention, especially during the last quarter of the year or in January, but I highly recommend prioritizing quarterly planning, especially for early-stage companies or small businesses with less than five people. 

A three-month period is not too long, unlike yearly planning, where it’s easy to lose focus and for the priorities become irrelevant over time. 3-months is also not too short. The milestones you can achieve in 3-months are meaningful. Quarterly planning also enables failing fast and making pivots easier when things don’t go well.

Tip #3: Start With Your Vision

One of your most important jobs as an entrepreneur is to have a hard-to-copy vision that translates into your roadmap. Take a break from all the typical tasks that take up your time and focus on nothing other than your big vision for at least an hour. 

Your vision should both energize you and scare you. It shouldn’t be about “how” you’re going to get there but more about “why” you want to get there. 

Tip #4: Declare Your Numbers

When you (and your team) feel clear about your vision, move on to declaring your numbers! Whether it’s your revenue or gross profit or the number of users or another metric you care about, link your big vision to a big, bold metric as your ideal goal. Then celebrate it with your team. The act of declaring a big bold number itself is something worth celebrating.

Tip #5: Get Serious About Your Strategy and Metrics

After you get clear on your vision and communicate it with everyone on the team, you need to define your strategy, tactics, and metrics for each one of your primary initiatives. 

I suggest creating a “one-pager” that fits in a one-page google doc, one slide, or a piece of paper. The one-pager is the foundation for each of your quarterly goals and should always be linked to specific metrics to measure success. 

If you or people on your team are not clear on the strategy and metrics for any of these initiatives, that would be a leadership fail you’ll need to pay attention to and fix before proceeding any further with your roadmap planning.

Tip #6: Reflect on the Past and Decide on Your Non-Negotiables

No planning will be complete without reflecting on what worked/didn’t work in the past quarter, six months, or year and setting new intentions.

This reflection needs to be brutally honest to be effective. 

So much of what has already happened inside your business (the good, the bad, and the ugly) influences how you’ll operate in the future. So get honest, ask questions, and adjust your roadmap accordingly.

Tip #7: Break the Planning into Three Different Phases

Effective planning should start with the “What,” then discuss the “How,” and end with putting things on the calendar.

I find companies get too obsessed with “how to build something” and “how to market what we built” instead of focusing on the “what should we build?”. The “what” question needs to happen before figuring out the “how”.

The “what” question should feel challenging and uncomfortable. It should make you (and your team if you’re not a solo entrepreneur) question the decisions you’ve made in the past. Your “what” can be driven by your bigger why, your mission, and/or your gut feeling but it should also be measured and validated by market research and quantitative metrics. 

When you become clear on your what, proceed to spend enough time on the “how” and practical milestones with deadlines. Don’t call your planning “done” until you’ve taken care of all these three steps.

How long should an efficient roadmap planning take?

Depending on the size of your company, you may need to spend a few hours to multiple days planning your roadmap. The length also depends on how many business or product goals you’re setting and whether you plan your quarter or a more extended time. Keep your planning as short and practical as you can but make sure you walk away knowing exactly what your priorities are for the next couple of months. And remember, if you have too many priorities, you can’t call all of them priorities. 

If you have a large team, you might find yourself struggling with who to involve and not involve in your roadmap planning. But too many people in the room can prevent you from having fast-paced discussions. Avoid including every single person in every single meeting just for the sake of team transparency. There are better ways to practice transparency than involving everyone in everything. Be selective about planning meetings and try to break the planning into multiple conversations with fewer people involved.

What about solo entrepreneurs?

Planning as a solopreneur can feel lonely, but it doesn’t have to. I’ve been personally there, and I relate to the resistance you might feel about dedicating time to proper planning when you’re doing it alone. It might feel like a waste of time to go through detailed planning without a team, but it’s really the opposite. When you’re just starting, you literally can’t afford to waste time and energy on stuff that doesn’t move the needle, and having a crystal clear roadmap will help you prevent that.

To make your roadmap planning feel less lonely, plan with someone who knows your business well, or someone who knows you well. Whether it’s your virtual assistant ( if you have one), a trusted colleague or even your significant other or best friend, present your roadmap to them and ask for feedback. 

Keep in mind that if you plan with someone who’s not experienced enough, you might have to be a little skeptical about their suggestions. This, however, doesn’t make their feedback invalid. They might actually surprise you with their unique ideas or the amount of excitement you can get out of simply presenting your ideas to someone who cares about your company’s success or you as an entrepreneur.  

What does success looks like?

A good roadmap planning should feel like a drama movie with a happy ending. There should be ups and downs, disagreements, confronting conversations, and debates with eventual resolution. 

Your job is to stay focused on your critical goals through all of it. 

As a leader, you need a mix of innovative ideas (example: an idea for doubling your revenue with only 20% increase of resources), optimism (for what you and your team are capable of achieving with the right mindset and focus), and healthy skepticism (to question every single priority).

Encourage everyone involved to prepare for the planning and stay highly engaged. You don’t need to go over every single detail; focus on the things that matter.  

Find your perfect balance, and don’t be scared of taking some risk to enjoy a higher reward potential. One way to do so is to dedicate 10% of your team’s time (or your own time as a solopreneur) to a “big bold bet” every quarter.
On the flip side, ineffective roadmap planning doesn’t give clarity on the “what” and “how”, doesn’t focus enough on metrics and data, and involves too many people with not enough contribution. 

Don’t spend your time creating fancy slides or showing off your organization skills. Be organized enough to function but not too organized to make your planning about how nice everything looks.

Your job as a leader is to constantly think about “what will customers think” rather than “what my family/peers/mentors/competitors think”. Whether you run a 7-figures consulting company, sell digital courses, own a local bakery, or are a venture-backed tech startup, obsess over the needs of who’s using what you’re creating and who’s paying for what you’re creating over everything else. Sometimes these two are the same, and sometimes they’re not — but what you need to keep reminding yourself of is that the opinion of those who’s not a part of your businesses should be the least of your focus. 

Encourage everyone who’s a part of your planning to participate aggressively during pre-planning, the actual planning, and post-planning conversations. There shouldn’t be any room for passive attending because that’s a lose-lose situation for everyone.

 About the Autor: Aria Massoudifar is a serial entrepreneur and product manager in tech mostly known for her role as a former product manager at Uber. Aria’s portfolio of her businesses and projects are: Her work as an online educator, course creator, and mentor is followed by thousands of people globally. She uses her platform to empower her 100k+ community all around the world. She is the founder of a newly launched health and wellness app Vito to help busy millennials take charge of their health. She is the owner of a popular mid-century vacation rental and photoshoot house in the heart of Joshua Tree. Aria is a multi-hyphenate and passionate entrepreneur who refuses to limit her pursuits and inspires others to celebrate and pursue all of their passions too! Connect with Aria on Instagram @ariamsfar.

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