🎶 It’s the most wonderful time of the year…🎶
Though that is probably not where you thought this was going, I do truly love this time of year because it’s a time to reflect on the accomplishments you’ve made throughout the year and the milestones you’ve reached. At the same time, you can think about those items that perhaps didn’t get done - the initiatives that kept getting de-prioritized or pushed out, the stretch goals that you’d do “when you have more time”. You know exactly what I mean.
As we work to wind down the year and start the next year’s planning, it’s the perfect time to work on your roadmap. I can go on and on about roadmaps - the different types, how to best execute on your roadmap, maintaining the roadmap, etc. We’ll save that for a different day, or you can also check out my personal blog where I have a few articles on roadmaps and my roadmapping journey.
I’d also love to share a bit of how we did our roadmapping at Talkbase.
The roadmap isn’t something that should be built in a day. There’s some pre-work that needs to be done by each member of the team. Here’s how the pre-work panned out at Talkbase.
- I created a template roadmap (you can see below for examples) and asked each team member to make a copy of it and fill out their own roadmap for the upcoming year. What programs do they run? What initiatives do they want to do? What events are they planning?
- I also looked at our company roadmap and incorporated company or other team initiatives that community would be supporting.
The roadmap should be a true collaboration and equally owned by all people on the team. Having each person go through their own roadmaps and goals for the year helps kickstart the process for thinking about priorities, bandwidth, and what level of support from other teams and direct teammates may be needed.
The Roadmapping Session
I then scheduled a roadmapping session - a multi-hour focus time for the team to come together. I love doing this in-person if possible, and luckily we were able to, as we were at a team offsite. This way, we can put our out-of-office messages up and be fully present with one another. Here’s how the roadmapping session worked:
- I started a master roadmap, which would be the official team roadmap. We all had access to this and had it opened on our laptops (or if you have a projector, you can present it too).
- Each person went around and talked about each line item on their roadmap. As a group, we’d provide insight on how we can support each piece, the timing, and if anyone else had something similar on their roadmaps. As we discussed each person’s items, I’d add them to the master roadmap.
- Once each person had gone around and talked about their individual roadmaps, we took a look at the roadmap as a whole. We looked for areas that may have had a heavier workload than others to see if timing of initiatives could be shifted around. We looked for areas where certain teammates may have more work than others to see if we could re-assign things. And we looked at the company goals to make sure the things we were planning to work on were aligned with the direction and priorities of the company.
At the end of our roadmapping session, we essentially had our completed roadmap. We did some fine-tune cleanup and organization after, and then we were set to start rolling.
To additionally set us up for success in the upcoming year, we then pre-scheduled quarterly roadmap check-in’s, added a few calendar blockers, and ensured notifications are turned on so we are alerted to upcoming items and deadlines. Here are a few things I would suggest for your roadmap maintenance.
- Each team member have a weekly recurring task to check on their roadmap items and update status, dates, add notes, etc. as necessary.
- The first week of every month, add a roadmap check-in during a team meeting. In this meeting, go over the last month’s items and what was completed versus what is carried over to the next month. Also, go over the priorities for the upcoming month and make sure everything is still accurate.
- The beginning of every quarter, do a debrief on the previous quarter and check in on the upcoming quarter.
A Roadmappy Gift for you
To give you a jumpstart on your own roadmapping journey, I’ve created a few basic templates that you are welcome to copy and use for your own teams. Feel free to add and change things up to better suit the needs of your community and your team. Remember that there is no right or wrong tool to use for your roadmap, as long as it’s easy to use, online/shareable with team members, and is able to collect the information you need.
🏆 And here are a few quick tips and tricks to be successful with your roadmapping:
- Don’t make your roadmap in a silo. Work with your team. Get input from stakeholders and leadership. Make the roadmap together with your team.
- Keep it high level. Sometimes it’s hard not to start adding rows for individual tasks related to an initiative. But the roadmap isn’t for project management and tasks.
- Don’t over-complicate it. Think about the important variables you want to track for each initiative, and add columns accordingly. But if your roadmap starts getting clunky and becomes a pain to update because how many fields there are, you may want to consider getting rid of those less important fields.
- Don’t forget to include initiatives where your team may be supporting initiatives and events from other teams (like for example, a company conference, supporting a new product launch, etc.). These things take bandwidth and effort from your team and should be accounted for in the roadmap.
Without further ado, here are a few basic templates to get you started.
Side note: If you need any help with roadmapping or would like to set up a guided roadmapping exercise and workshop with your team, reach out to us at email@example.com.
November 28, 2022
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