When Roadmaps Go Rogue

Some tips for how to re-plan in challenging circumstances in large-scale organisations

Many companies interviewing Product Managers will employ some kind of scenario-based task. In recent years, I recall an example called ‘Fast Cars’.

The task is there to test the candidate: it’s a scenario where you have been brought into a project that is wildly over budget, well past the milestones they would look to hit and with a heap of issues raised by dependent teams.

The question is: what would you do?

It’s deliberately open-ended to show how the candidate approaches challenging situations, how they creatively solve problems and how they prioritise. The idea is that no-one would sit by and watch this happen without making some key changes, often in the form of a new roadmap or a planning exercise.

I found myself in a similar situation while working as part of an enterprise organisation on a project that was seen as a pilot programme for a much larger digital strategy and, while assumptions can be made in a hypothetical interview scenario, in real life there are some basics you have to get right. Especially on projects with a lot of visibility, and a lot of notoriety.

As you may expect, we found ourselves in a position where we were facing down the barrel of an almighty re-planning exercise. Here are some of the key things learned from the experience.

Challenges

Re-planning exercises are challenging for a number of reasons. Mostly from a time and effort standpoint, where it can be as deep as ripping up an entire roadmap and re-evaluating everything.

It often means going against ways of working or an approach to the project that is set in stone. Re-plans rarely come immediately after a shake-up, so you may face the challenge of changing something that many people are comfortable with.

It can also be challenging to bring everyone together in unity. On large-scale projects there are often a vast number of people included in the RACI diagram and so it becomes a political decision. Then there’s the communication to all these people, and often people disagreeing with how involved they should be (hint: either everyone is an R on the RACI diagram, or they don’t care whatsoever).

Tips to Overcome

The first major difference between a hypothetical interview question and a real-life example is that you’re not sitting by yourself in a panic in real life. You should have a large supportive team around you... sitting in a panic.

Involve the Team

The first and most straightforward thing to highlight is that a re-plan can’t be done by one person. It takes the involvement of product, tech leaders, delivery specialists, business decision makers and domain experts.

Communicate to Your Target Audience

The best way to communicate a re-planning exercise is to align the outcomes with your audience’s goals. If your audience is only interested in the bottom line, then pitching it through a lens of cost-saving will help give some sugar to the pill. If time is your biggest challenge, then structuring it around that. In our case we made manageable milestones to hit, which helped radiate confidence rather than reduce it.

Once the conversation is focused around the target metric (financial, time planning, resources etc), a next logical step is likely to be re-evaluating your MVP targets. In complex environments with many dependent teams and business stakeholders that need results, consistently grooming the backlog is crucial, especially when there may be scope to shift features or tickets to a post-MVP state. In large-scale and long running projects, it can’t be one plan that is then blindly followed, especially with so many moving parts.

Larger organisations with multiple dependency departments and teams often need a lot of communication around big changes. This is to ensure that everyone is singing from the same hymn sheet when it comes to backing the decision. Tight communication strategies are essential to ensure everyone has been informed, as the last thing you need is a hand being raised to say they have an earlier dependency than anticipated, and you have to restructure to accommodate.

Centralise Decision-Making

While managing this in real life, we found that a centralised PMO team helped to structure communications clearly. Not everyone will have access to personnel or resources to achieve this, but even just a point of contact who is there to direct communication is crucial. When ideas aren’t fully formed and are taken away by people with good intentions but poor reasoning, it can lead to more confusion. There should be a reference point for everyone in the surrounding area.

Communication, alignment and being level-headed about how to reach your goals are the key takeaways we learned. It’s important to remember that any new plan, especially late in a project lifecycle to help you get to your goal, is unlikely to be popular with everyone. The main things you can do are keep the goals of the project in mind, keep the communication channels open and keep the message aligned.