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16 Tech Leaders Share Their Favorite Project Roadmapping Tips

Forbes Technology Council
Updated Apr 21, 2022, 08:15am EDT

Project management is an essential task tech leaders have to master. But it entails more than just planning the path from point A to point B. To effectively guide their teams through a complex product development process, leaders must clearly articulate the vision, define and prioritize the steps needed, determine and communicate roles, and ensure the project stays on track—all while being ready to pivot as needed and keep up with all their other work. It can be a daunting prospect, indeed.

Fortunately, the members of Forbes Technology Council have lots of experience in project roadmapping. Below, 16 of them share strategies that can help a tech leader develop a project roadmap that will lead their team successfully through the milestones to reach their desired destination.  

1. Begin With A High-Level View

Begin by creating a project scope with a big-picture vision that’s in alignment with business goals and a high-level project schedule. Then identify deliverables and milestones. Finally, take into account risk factors such as resources and budget to adjust and finalize the timeline. - Zheng Fan, University of Miami Herbert Business School

2. Identify Current Gaps

For project managers who want to get buy-in on their project, it is very important to identify and link the gaps from the current state to the future state roadmap and articulate those gaps effectively to stakeholders. Communicating both the cost of fixing the gaps in the current and future state and the cost of doing nothing in the current state will lead to quick project approvals from stakeholders and help you move on. - Buyan Thyagarajan, Eigen X


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3. Define The Objective And The Necessary Outcomes

A practical way to do the roadmapping is to start from the top and define an overarching objective. Then, define the most important outcomes—the outcomes which, if met, will guarantee that the top objective has also been achieved. Go further and start breaking down the actions that need to be taken to reach the important outcomes you’ve defined. Finally, continue the process until basic actions emerge that don’t have any dependencies. - Archil Cheishvili, GenesisAI

4. Think From The Customer’s Perspective

We follow a counterintuitive approach to roadmapping project initiatives: Thinking like a customer is the name of the game. In my view, new methods equal new value. Through design thinking and prime value chain analysis, the customer’s perspective guides the operating model transformation, which is required for building better functions. - Ranghan Venkatraman, Rezilyens LLC

5. Prioritize Key Differentiators

You need to identify several factors, beginning with your differentiators. You must identify what your competitors already have that you don’t, a new feature to attract your first customer, experimental features for a new customer and proven features in the market space. Priority and risk can be assessed to chalk out a road map based on the engineering team’s capabilities and your customer’s needs. The highest priority should always be given to key differentiators. - Bhagvan Kommadi, ValueMomentum

6. Set Up A Weighted Matrix

Utilizing a weighted matrix approach to prioritization lets the most important projects overall rise to the top. It allows space for all needs to be met and ensures that the most important work for the business as a whole rises to the top of the list. I recommend using only four to six prioritization scores and ensuring everyone agrees on how they are weighted for the business. - Kathy Keating, Ad Hoc

7. Classify Roadmap Items

Often, one big missing piece of the puzzle is communicating the level of effort needed for building a feature and establishing guardrails around the time one can invest into building a feature. The business or project manager should classify their roadmap items as “experimental,” “lighter usage” or “heavier usage.” A feature could be built differently depending on whether it’s “experimental,” for a single client or for many clients. - Sudheer Bandaru, Shortlist Professionals Services Private Limited

8. Take A Two-Level Approach

Roadmaps are not Gantt charts. You need at least two levels of roadmaps: a strategic view and a work view. The strategic roadmap is external if you sell a product and internal to the business if you don’t. The work view shows what is planned and what is completed. Also, be sure you have a consistent definition of “completed” so leaders can rely on it when making data-driven trade-off decisions. - Laureen Knudsen, Broadcom

9. Don’t Forget Resource And Capacity Planning

Resource and capacity planning is often overlooked. Most organizations have a few “go-to” people for projects and strategic initiatives, and those same people are often also the firefighters when other operational issues occur. It’s important to be able to identify and compensate for future constraints on their time, including leaving unallocated time for them to deal with unforeseen issues not related to the project. - Jerich Beason, Epiq

10. Avoid Setting A Project Deadline

Resist the urge to set an arbitrary deadline. Most projects will have better outcomes if you focus on making consistent progress rather than racing towards a finish line that most often has little to do with customer value. - Punit Shah, EZ Texting

11. Make The Process More Manageable Through Sprints

One of the most important roadmapping techniques to master is sprint planning. This project management roadmapping method breaks projects into two-week increments, creating more manageable and measurable product timelines. In doing so, organizations benefit from cross-functional team collaboration and clear-cut executables, accelerating a product development timeline by leaps and bounds. - Marc Fischer, Dogtown Media LLC

12. Utilize Wardley Maps

One effective roadmapping technique that has a real strategic impact is the Wardley Map. It isn’t just a placement of key components or a sequence; it also looks at how tech components move across a business strategy and how value chains evolve over time around those tech components. It isn’t the only roadmapping method, but it’s one of the most revealing, especially if you are using a product-led growth framework. - John Cho, Peraton

13. Lay Out An Agile Wall

The Agile Wall is one of the most effective and practical approaches technology leaders can take to drive execution, clarity and alignment across stakeholders. During the execution stage, this entails visually laying out expected outcomes, progress and potential pitfalls, which enables teams to uncover opportunities and build minimum viable products through a successful, structured development cycle. - Sayandeb Banerjee, TheMathCompany

14. Employ Time Tracking

Most project managers hate this—I used to—but time tracking is crucial for any successful project management practice. If you get into a healthy and fluid rhythm of tracking your hours, it helps dial in your focus. You can quickly tell whether you are spending the majority of your time on major rocks or just smaller pebbles. Always translate these hours into visual metrics as well! - Jordan Arvin, Renovia

15. Maintain Flexibility

Flexibility is crucial. Understand the roadmap while still maintaining the flexibility to accept that most things will take longer than you expected and there will always be complications. The objective isn’t the specific features but aligning the team toward tackling the most important or time-sensitive goals. - Noah Mitsuhashi, Portfolio Insider

16. Continuously Reassess And Reprioritize

Your roadmap is not carved in stone! Start with a clear and ambitious product vision. Identify the features needed to deliver that vision. Group similar features together into epics. Break each feature into tasks related to user stories, and estimate the complexity of each story. Prioritize your features and map them into sprints and releases. - Nick Herbert, Fujitsu

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