Get an unbiased opinion
Ask someone from another department, unrelated to the project, to review the Roadmap. That person should be able to understand the milestones and impacts and what they are designed to achieve.
Address interdependencies and risks
Identify all critical interdependencies and key known risks (such as operational, technical, behavioral, health, safety, security, and environmental), along with quantifiable lead indicators to address them at the milestone level. For interdependencies, ensure that an explicit conversation with all involved parties has taken place and lead indicators are in place at least one and three months prior to delivery.
Address and foster collaboration
If the initiative requires collaboration across business units or functions, talk through how all parties will work together. Identify all key internal and external stakeholders, including the most influential supporters and skeptics. Use the supporters to generate momentum for the project. Engage the skeptics, address the points they raise, and—ideally—involve them in solutions.
Use the DICE tool
Conduct a DICE assessment to confirm the Roadmap is set up for success. DICE is another change management tool, which we discuss on an accompanying website (with associated HBR article).