Sometimes the roadmap leads you on roadtrip detours

12 min readMar 10, 2022

This post is about my still-in-flight adventure changing my current my roadmap tool for another. I provide my train of thought, shed some light on my methods, and I will be the first to admit it’s not perfect. However, I believe you learn by trying and failing, and that it’s helpful to know the reasons why one chooses to do one thing (or chooses not to). I don’t believe in having an ego, and I hope sharing my learnings and experiments here provides some value and insight for you as you embark on your roadmapping adventures.

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I have a recurring task every other week to look at and update the community team roadmap. I look at ongoing initiatives, make sure dates are still right, update statuses, and add notes on line items. I also take a look at upcoming items, making sure we’re still on track for the start dates, when I should move items to the “in progress” section, and giving the line item owner a heads up.

For the last few months, whenever these recurring tasks pop up on my to-do list, I’ve found myself feeling frustrated. The tool that we’re using had some limitations, there were evergreen/ongoing items that were taking up space but we used for capacity planning, the whole roadmap was a bit clunky. What was once an activity that I looked forward to became one I found myself procrastinating on. It was a sign to me that I had to change something.

Unfortunately, Yoshi’s only “meh” about roadtrips.

Capacity planning, headcount request

Our first roadmap was created in November 2021 for the 2022 calendar year. We were a new team of three — VP of Community, Director of Community, and Director of Community Operations (that’s me!). This roadmap had two goals -

Plan out 2022, the programs we’d launch, improvements we’d make, events we were participating in, community initiatives and engagements, etc. The normal “roadmappy” stuff. It would be the first year doing this, since our community launched in September 2021.
Conduct a capacity planning exercise, looking at the hours the three of us were spending on items in the roadmap and our normal “run the business” tasks, including meetings we participated in, and daily tasks we did.

The capacity planning would show that we were overextended in our work and would be included in our business case for headcount request for 2022. It would also show what we could accomplish with additional headcount, or in a second scenario, what we would not be able to do without this additional headcount.

I decided to use Team Gantt for this. We had a detailed roadmapping session (I’ll write a post about how to run a team roadmapping session sometime) and came up with the roadmap. Here is how we set it up:

By Program — We started by looking across all community programs and initiatives we would be running and classifying them in a higher level bucket category.

The roadmap with larger categories by program or initiative.

Line Items — We drilled down a layer deeper for the programs and looked at actual line items for each program, also noting the timeframe which that item is taking place.

Individual line items within a community program or initiative.

Capacity Planning — And then we looked across the team and determined estimated hours that each team member would spend on a given line item. We did this either looking at the total hours end-to-end for the initiative, or per day or per week bandwidth that would be allocated. We also did some future planning by allocating hours to what the new team member would do, pending the headcount approval (in the below image, the Community Manager).

Capacity planning by team member for each line item.

Unexpected road bumps and detours

This roadmap worked well for us to see how much we would each have on our plate for the upcoming year. Looking across the year, you could see when each of us would be busier leading initiatives, and when we had a bit more downtime. It also became very clear that we would need additional headcount in order to accomplish the expansive list of things we wanted to do. However, it didn’t take very long for us to see potholes in the road. (Yes, I am going to keep with these puns — keep your seatbelts fastened, folks!)

Confusing bandwidth readings

For our roadmapping purposes, we weren’t necessarily interested in the traditional capacity planning, in a sense of looking at daily granularity. Rather, we wanted to see, at a higher level, when people would be busy or over the number of allocated working hours. With the view we got, it was difficult to capture our team’s bandwidth in a way that was presentable to our executive team (who we’d present our headcount request to).

Jumbled numbers showing our bandwidth. The only designation that was clear was the red coloring.

If you hover over a specific number, it would show the number of hours for that teammate for that specific day.

You can hover to show the number of hours assigned to that team mate for a specific day.

We could zoom into the roadmap to see the numbers day to day, but looking at the roadmap for the year, this view wasn’t realistically helpful for us.

In the end, we relied on the color of the row by team member to assess general business, though we had no idea how much more above the 8 hours a business day threshold each person was. In other words, we had no way to see if someone had 9 hours or 16 hours allocated to their day.

A high level glance at team member bandwidth over time.

Ongoing “run the business” initiatives

It was important for us to capture the everyday “run the business” items that we spend time on in our day-to-day. These things are sometimes not included in roadmaps since they’re just ongoing tasks or things people do, but we wanted to include them in our roadmap because they still took time out of our day to do. A few examples of things we included in this category:

Responding to community support cases
Platform management and maintenance
Meetings (e.g. team meetings, all hands meetings, 1:1’s, interviews, training sessions, meetings with stakeholders, etc.)

There are 40 hours in a typical work week, but when you consider the amount of time spent in meetings, doing administrative tasks, and general day to day items, you find that you have significantly less than 40 hours a week. If you don’t incorporate these items into your capacity planning and then plan to have 40 hours-worth of work on the roadmap, you’re actually signing yourself up for 40+ hours a week.

We tracked these ongoing items as end-to-end line items spanning across the entire year. You can see from the above screenshot the platform management items in yellow; they went from January 1, 2022 to December 31, 2022.

The issue? It made each community program category very clunky. In each category there were several rows that just never got touched or updated. Also, there was no way to denote cyclicality or seasonality into the capacity planning; it was a cumulative number of hours evenly spread over the year. In other words, it was not very accurate.

These line items became stagnant items that we just started glazing over. It lost its value, and so finding a new way to include these ongoing tasks in a meaningful way was another factor in finding a new detour route to take.

Too many detours leads to a sleepy roadmap. And a sleepy Yoshi.

Views, filters, and flexibility

My team comes together once a month to do a roadmap cleanup. We check all of the statuses of everything, update dates, any team assignments, and make sure we’re clear on the priorities for the month and close out items from the previous month. (Note — we do this individually on a regular basis but make it a formal item on the team meeting agenda for the first week of every month).

With our current roadmap, it was pretty painful to go through each item. Expanding each program category, we still had to sort through all of the items for the year, there was lots of horizontal scrolling to go across months, and it wasn’t easy to see which items were actually in progress or who was included in each item without clicking on each line item. It was also impossible to sort by team member to just see what that person was working on.

Our meetings became less productive because we had to navigate through each line item in the roadmap, rather than focusing on the current and upcoming items.

A light at the end of the tunnel

I want to preface this section by mentioning that I think Team Gantt is a great tool. It’s intuitive, has different formats, you can incorporate RACI into your roadmap items, and I love that it automatically updates the hours and effort when you change the duration of a line item. I’d recommend Team Gantt to anyone who is looking for that level of detail in their roadmap. However, it isn’t the best solution for us, and that’s totally okay to recognize.

I started looking through other roadmapping solutions and playing around with free versions of different tools. Knowing where we were and what our maintenance was like with our existing roadmap, I knew I had a few non-negotiables when it came to features and also a few nice-to-have’s that would make life much easier for my teammates and myself.

Team capacity planning (high level): The specific hours aren’t as important for our use case as general effort and time that team members need to spend on their initiatives. We need to see when team members have a lot on their plate and can’t take on anything else, not that they are working 10.2 hours next Wednesday.
Multiple ways to sort and filter: If I want to see only line items that are “In Progress”, or all line items next quarter, and sort by Program, I can arrange my view accordingly.
Groupings: I can group like initiatives together (e.g. all line items in the Online Community program category)
Notes: The ability for team members to add notes on each item.
Labels: The ability for us to add labels and better organize or filter our items.
Views: Ability to see the roadmap in a different view (e.g. I just want to see my items and not someone else’s)
Format — Kanban, Gantt, Grid, and being able to switch between the views
Collaborative — Obviously, all team members need access to the roadmap and should be able to edit it directly.
Slack Integrations — Ability to get notifications in Slack for various updates to the roadmap.

I decided to dive deeper into Airtable. Truth be told, I’ve been looking for an excuse to learn Airtable for a long time now, but haven’t had the need to because it was never part of my company’s used platforms. I’m behind on the Airtable scene, a latecomer, if you will, but I’ve only heard great things about it and had it in my personal goals to start learning how to use it.

Within maybe an hour, I had fully transitioned all of the items from the old roadmap to my new one, and then some.

The new roadmap

This view is the full roadmap, every item.

I added several columns with various labels which allows for various sorting and filtering capabilities.

Status — Shows the status of an initiative (i.e. not started, in progress, ongoing, complete, blocked, etc.)
Category — These are the original high-level program categories.
OKR — To tie each line item back to the OKR that they help achieve. Not all line items may pertain to an OKR, but this label allows us to easily see what we are doing to accomplish our goals.
Labels — These labels are a bit more generic in case we want to do any filtering or assessing where our priorities are. (e.g. internal, support, engagement, recognition, operations, ideation, swag, etc.)
Quarter(s) — What quarter(s) these line items take place. Realistically, many items continue from one quarter to another, and this column allows you to easily see that.

Also in this table, I added start and end date, the team members who are involved in each initiative, a notes column, and an effort column.

Diving in on the Effort column a bit more, this is the new version of capacity planning. Rather than focusing on the granular hour, or number of minutes, you spend on an item, we focus on a general 1–10 rating. An item with a 1-rating is minimal time spent on it, oftentimes referring to the “run the business” items, just a little here, and a little there. Items with higher ratings closer to 10 are more intensive in time and effort for the teammate. More on that in a bit.

Other Views

Airtable allows you to create various views using the same base table. With these views, you can create different versions of the roadmap to view what is most relevant at the moment.

Active Items — Filtered by “Status” and only showing items that are Coming Up, In Progress, or Ongoing. This view can be used as a quick glance into what each person is currently working on.

Grouped by OKR: See how we are tracking on items by our OKRs.

This Quarter: See only items that are relevant by the current quarter. This does include ongoing initiatives.

Grouped by Team Member: See what each person has on their plate on the roadmap.

Grouped by Category Similarly to the original roadmap format, each line item is grouped by its program category.

Team Bandwidth

Though these views help us see items and stay better organized, a bit part of our original roadmap intent was for resource and bandwidth planning. Remember above, I added the column for Effort with a 1–10 rating on how much effort and time the line item would take for that team member.

I then created a new tab called Team, and using some formula fields, created a table that shows team member, the number of active items they have, and their current cumulative effort score.

I’ll be the first to admit, this is not a perfect science. You’ll notice row 3 here has an effort score of 43. Is that a lot? Should there be a maximum effort score? These are things I think we would need to play around and work with — learn what those thresholds are and how to properly rate items on the roadmap. However, it does provide a snapshot of the team’s workload.

Where will the road take us next?

As I mentioned at the beginning of this post, I wrote this before actually implementing or launching this roadmap. But, I’m excited about what I see, and know it’s already a drastic improvement from what we had before. There are a few outstanding items for me to think about and/or do from here:

Effort score for different team members on the same line item. There are a lot of initiatives where multiple people are working on it, and very rarely are people working on the initiative to the same capacity. For example, the project lead will usually work more hours on the project than someone playing a supporting role. I’m thinking about the best way to incorporate that calculation for different team members.
Effort score standardization. Figuring out a way to set a defined scale for the effort ranking, both for the individual line items and also for the cumulative score.
Walkthrough of the roadmap with the team. Showing my teammates the new roadmap, the reason why I think switching from Team Gantt would be the best interest for us.
Buy the premium version. Airtable’s free model allows for most of the formats, but using the Gantt Chart or Timeline format would help provide different views that could be useful for sharing with stakeholder teams and others across the organization.

Stay tuned for more updates — I’ll be sure to let y’all know how it goes!