RoadmapPing 101

Purpose: What is it? Why do you need one – or are asked for one?

There’s always more to do! And yet there's always a trade-off to everything: when you do X, you’re not doing Y – and quite possibly also not doing A, B, and C.

As you may already know, because of the Project Management triangle, you can’t do it all: "quality of work is constrained by the project's budget, deadlines and scope"; you can have two out of the three, but not all three.

A roadmap, when done well, will align the company – and all of its teams – on what the top priorities for everyone are for the next quarter/year, and (more importantly) what’s not a top priority and will not be worked on for the next quarter/year. It identifies and communicates a company’s priorities and how they will be used as opportunities for growing the company.

This is much easier said than done – and many take (many) months to get there. Here’s the process that I’ve found works for me.

Design: What it Looks Like?

What it physically looks like, may depend on the company. It can be as simple as a:

• List of projects/priorities/”epics” that hit business objectives in a Google Sheet, with one list per quarter,

• A Gantt chart of priorities and dates of deliverables associated with them (in JIRA, Notion, etc.), or

• A table (in your favorite software) tracking priorities, business impact, team driving initiative, collaborators, etc.

Typically, objectives are ones that the company presents, and is held accountable for, to the board.

Please find out from your executive:

• What time frame should the roadmap cover? That is, what cadence should the company and teams use, to align on priorities? (I’ll be using quarters here.)

• What are the board-level goals and KPIs for the year and quarter (to align projects to moving the needle on those)?

• Are there any other objectives or company goals/targets we should also consider?

• What format and content would they prefer for their roadmap? Depending on the company, the roadmap may also include “stories” of how to get there, how the project is moving or if it’s blocked, who the driver is, etc.

How to Get Started?

Goal: Suppose a company wants to hit a certain revenue target (or a board metric, KPI, or One Metric That Matters (OMTM)) for the quarter.

Approach 1 to Getting to Roadmap

• As an executive, identify the top 1-3 initiatives for the company as a whole to get us there. These are the top goals that really need to get done, above everything else.

• Ideally, these go on the company-wide roadmap for the quarter. All of the teams/departments within the company then prioritize and collaborate on these 1-3 initiatives for the quarter – to hit the revenue goal, and deprioritize everything else.

I say “ideally”, because having collaborated with 25+ companies over the past few years, only a handful have a cross-company product roadmap. In an opinion piece for dot.la, I share advice for how to get there.

Here’s what usually happens at most companies:

Approach 2 to Getting to Roadmap

1. First, in parallel:

• A. Top-down: Find out what are the company goals or objectives that it's targeting for the next quarter. Is there a revenue target (or a One Metric That Matters (OMTM)) we’re trying to hit?

  • • As an executive, you will also suggest (about) 1-3 initiatives for how the company as a whole will aim to hit the objectives – and how will that be measured.

      1. • Ideally, these go on the company-wide roadmap for the quarter. All of the teams/departments within the company then prioritize and collaborate on these 1-3 initiatives for the quarter – to hit the revenue goal, and deprioritize everything else. I say “ideally”, because having collaborated with 25+ companies over the past few years, only a handful have a cross-company product roadmap.

    • If you’re not an executive, try to find this out as well.

• B. Bottom-up: Ask the team to identify, evaluate and suggest short- and long-term initiatives:

  • • (Short-term) What data products/requests to get done in the next quarter, including any ongoing/recurring products/requests, that drive business impact?

      1. • e.g. Weekly revenue reporting and deep-dives to understand drivers of trends

    • (Short-term) What KTLO (keep the lights on) needs to get done, that will have an adverse effect on the business if we don’t do it?

      1. • e.g. Hiring for role X, or

         • e.g. Refactoring query Y to improve real time dashboard response time from 4 hours to 20-minutes, enabling same-day decision-making and interventions

    • (Long Term) What (strategic) ideas for high impact data products/KTLO should we consider including for next quarter? These may include, anything that can help us:

      1. • Get to a future milestone, 1+ years from now;

         • Collaborate better with stakeholders across the company;

         • Scale, including with improvements to infrastructure/processes/software.

  • C. While you’re doing that, all of the other Departments/teams in the company are doing the same thing.

2a. Create a summary of recommendations for how your team will support the company in hitting its quarterly goals, balancing short- and long-term initiatives.

2b.. Ask your team to evaluate their current capacity for new work, outside of ongoing/recurring data products/requests

3. Then the fun part begins: reconciliation and alignment across the teams and departments! (More on this in the next section.)

Iterative Process

In the process of creating the roadmap, you’ll end up prioritizing and negotiating with other teams/departments on product, feature, and/or other requests, via data-driven prioritization:

• How data product X (for example) contributes to the top company business goals,

• What (if any) data is available to create the data product,

• What the deadlines and deliverables are,

• What the team’s capacity is, to hit the (scoped down) deliverable,

• What the interconnectedness of the data product is, to other projects.

This will involve (many, many) meetings with executives and key stakeholders across the company, to align on objectives and priorities across the teams. In the end, each team’s roadmap will complement each other’s, and aligns on company objectives for the quarter.

With a cross-company roadmap in place, everyone will be on the same page about priorities, and it will help to push back on requests that don’t directly tie-into them. If the roadmap tracks progress as well, it will also help you see how each project is moving/blocked and how close the company is/isn't to reaching the goals of each initiative.

Be prepared that it may take longer than you think!

Parting Advice

• This process to (especially the first) cross-company alignment on a roadmap may take (many) months.

• Keep adding to the backlog, as ideas come up, so that the roadmap is always up-to-date – and then you shouldn’t need to do step 1B in the second approach to roadmapping again

Good luck!

You may also like

• Column: Your Business Has Lots of Ideas on What To Work On. Here’s How To Decide on What’s Next

• How to Deliver Business Impact with Data

References

• Cartoon: https://www.cartoonstock.com/cartoon?searchID=CS443435