Kirsten Moorefield, Cloverleaf

Building an Adaptive (But Focused) Roadmap

This article was contributed by Kirsten Moorefield, co-founder and COO at Cloverleaf. Cloverleaf helps build great teams and improve employee engagement using existing employee data and assessments to provide insight into increased team engagement.

In 2017, my cofounder Darrin and I launched Cloverleaf with an (embarrassing) MVP. Ouch, it was awful.

But it validated the market opportunity.

In October 2018, we launched our commercial product. 2 years later, we’re proud to be serving some of the world’s largest brands as we quickly approach half a million users. Until now, we’ve had a team of 3 engineers, design done by interns, and our product management done by ⅓ of my time… These lean resources have forced us to be in lock-step with the market, building the 20% that brings 80% of the value. And it’s worked. So well, in fact, that we’re multiplying the size of our team.

Despite this growth, however, this lean approach will remain core to how we operate. We have to find a way to bring our adaptability from our early days into the more sophisticated, focused product company we’re becoming.

Here are some tactics that have helped us manage a product roadmap that is quick enough to respond to the market, yet steady enough to build a focused, consistent, successful product.

Consistent Mission & Vision

It sounds cliche, yet it is such a challenge: be clear on your company mission and product vision, and come back to it over and over and over. AND OVER. This ensures that each new feature fits the direction. It has also given us something to point our people towards, to remind them of our focus.

Clear KPIs

Or OKRs, OGSMs… whatever core 1-3 metrics the company is focused on, apply those rigorously to your product roadmap. At Cloverleaf we always have 3 KPIs, ranked in importance, and I then tag everything on our roadmap with the KPI it helps us accomplish. If it doesn’t fit a KPI, it doesn’t fit the roadmap. (Confession, we are not perfect at this one.)

Product Board Meeting

Eisha Armstrong from Vecteris shared this game changing advice with me: once a month, get the key product decision makers in the room to have a board meeting all about product. For us, this is Darrin, the CEO, who represents the market opportunities; myself, who owns the product; and Matt, our CTO, who can talk some technical sense into us crazy visionaries.

We look at metrics, discuss (expected and unexpected) opportunities, and end with reprioritizing our roadmap. Sometimes, there are no changes to the roadmap. But usually there are some tweaks.

About once a quarter, we double the time of the Product Board Meeting to do a “Roadmap Special Edition!” It goes something like this:

  1. I set a time timer for 3 minutes. We each write down, from memory, the most important features for us to focus on. From memory is important; it helps weed out what is no longer impactful.
  2. I then pull up our existing roadmap (because, yes, short term memory isn’t perfect). We add any new features from step 1. We make sure we’re all clear on what each of the features are.
  3. We each write each feature on a post-it (or a digital version for these remote days).
  4. I set the time timer for another 5 minutes. We place each feature on an impact vs. effort matrix independently, in silence. (We clarify impact as impact on our KPIs. Don’t get distracted by fun or personal passion impact that won’t strategically grow your company.)
  5. We then discuss any major discrepancies. But often, we find we’re already aligned on the big ones.
  6. We rearrange our now/soon/later roadmap (see below). Anything low impact is either put “later” or totally removed. High impact/low effort is often put in the “now” column (but not always). Sometimes a high impact/high effort wins, based on the market opportunity.

The Now / Soon / Later Roadmap Framework

This is a commonly used framework, shared with me by Lydia Henshaw.

It’s simple. You organize your features into 3 columns: Now (what you’re immediately building), Soon (what you’ll do next), and Later. For us, these 3 columns are usually about 1 year of work.

Developers have a bad rap for “never committing to deadlines.” We do commit to deadlines, just short term ones. We only set deadlines on projects that we commit to completing within 2 months. (if you have projects larger than 2 months, break them into chunks.) After two months there are no deadlines, just estimates of “soon” or “later.”

Spoiler: we rarely get to “later.” Later is the stuff we see on the horizon that may hit with a market opportunity. If that opportunity (think revenue, signed contracts) doesn’t land, we don’t move the feature from “later” to “soon.” There are some features we know we will get to, but it could take us a few years to have the resources to do it right. In our opinion, that’s okay. For now, it stays in “later.”

This roadmap framework is freeing. I don’t spend time agonizing over monthly, even quarterly priorities, and I have a clear vision to follow and share with the team.

The now / soon / later roadmap framework is freeing. I don’t spend time agonizing over monthly, even quarterly priorities, and I have a clear vision to follow and share with the team.

It also means that, when that big contract finally hits, we’re not whiplashing our company. We’re staying solidly on track, just moving something from “later” to “now.” For example, we’ve always known we’ll need to localize and translate into different languages. We get the request monthly, if not weekly (which is how it made it onto the roadmap to begin with). We’ve just been waiting to do so until someone pays us for it (hence why it’s been in the “later” column: it’s high effort and unknown impact until someone puts skin in the game). Now, a client is paying us for it so it shifted quickly to the “now” column, which reorganized everything else in the “now” and obviously pushed back “soon” and “later” priorities.

So what happens to all those other features? That’s what a monthly Product Board Meeting is for, my friends.

This is what we do to balance an adaptable, responsive roadmap (which 2020 has pushed to the limits), while still staying focused and consistent, and keeping the team aligned to a vision. With a clear mission, consistent KPIs, monthly board meetings, and a flexible roadmap framework, we’re able to recognize and jump on opportunities without giving the team whiplash. But one of the best things about product management is that it’s really a big creative opportunity. There’s no one right way. Take from this what works, and leave what doesn’t. Just be sure to find what works for you to make the best possible product decisions.