What are the best practices for introducing roadmapping as a product management practice in a transforming organization that is new to product practices and mindset, and how can you ensure that different teams stay consistent with the formats or frameworks used, while still allowing for flexibility and innovation?

I think that the answer to this is: it depends. The specifics of how you go about introducing roadmapping, promote a product-based mindset, and establishing a consistent strategy for educating teams on product practices is going to depend on your organization, your industry, your leadership, and your customers. There are a lot of different strategies and frameworks out there that you can decide to adopt for your organization. However, I do think that there are some things that could be called "best practices" to help with deciding exactly what your product-led organization is going to look like. It is going to require a lot of thought, work, and transparent communication, but it is definitely doable. Here are some things that I think would help.

1. Understand the current state:

   1. Conduct an assessment of the current project-based approach and existing practices.

      • Why was the org operating the way they were before?

      • What was the main motivation for deciding on which project the teams were going to work on?

      • Who had the most input into those decisions?

   2. Identify pain points, gaps, and areas for improvement in the current processes.

      • Are there things that were working well or that only need a little tweak to improve? It isn't always necessary to completely throw out everything that is currently happening.

2. Establish the Why:

   1. Why is it important for your company, specifically, to move towards a product-led roadmap process?

      • Answering this question is going to be key to getting people on-board with the mindset. Saying that you are moving to a product-led roadmap without establishing why it is necessary for the future success of the company will only look like you are trying to build your empire within the organization. Without the why, it will be incredibly difficult to bring people along with you in the journey of transforming your org.

3. Define a product vision and strategy:

   1. Clearly articulate the organization's product vision and strategy to align teams towards common goals.

   2. Communicate the importance of transitioning from a project-based mindset to a product-led approach.

4. Educate teams on product mindset:

   1. Conduct training sessions to educate teams about the fundamentals of product management.

      1. Define what PMs are responsible for and why. If you are taking responsibility and authority away from other roles and giving it to PMs as a part of this transformation, make sure they understand the reasons for it and why it will help the company as a whole.

   2. Emphasize the shift from project-based thinking to a continuous product lifecycle mindset and why it is necessary for the company's success.

5. Establish a common product language:

   1. Develop and disseminate a glossary of product management terms and definitions to ensure a shared understanding across teams.

      • GitLab's product handbook is an excellent example of this. Teams can't have consistency if there is no single source of truth of how things are done. There can still be flexibility within some of the specifics, but the broad terms and definitions need to be agreed on by all the teams.

   2. Use consistent terminology in communication to minimize confusion.

6. Create a standardized roadmap framework:

   1. Design a roadmap framework that aligns with the organization's product strategy.

   2. Clearly define key components such as themes, initiatives, milestones, and dependencies.

7. Customize roadmap templates for individual teams:

   1. Tailor roadmap templates for different teams or product lines while maintaining a standardized structure.

   2. Allow teams the flexibility to include specific details relevant to their products.

8. Implement roadmap review and alignment sessions:

   1. Conduct regular roadmap review sessions to ensure alignment with the overall product strategy.

   2. Provide a platform for teams to share their roadmaps, discuss dependencies, and identify potential conflicts.

9. Foster cross-functional collaboration:

   1. Encourage collaboration between product managers, designers, engineers, and other relevant stakeholders.

      • Emphasize transparent and inclusive communication. Everyone has good ideas. Everyone has bad ideas (even PMs!). No one is perfect and everyone should be comfortable admitting when they have made a mistake. Establishing a shared set of values (like GitLab's values) can ensure that everyone has a shared framework for understanding how communication should happen.

   2. Facilitate cross-functional workshops to build a shared understanding of product priorities and challenges.

10. Integrate feedback loops:

    1. Establish mechanisms for continuous feedback on roadmaps and product priorities.

       • Talk with your customers! Don't rely on only on sales to let you know what customers are saying. Sales has a great idea of what their specific customers need, so you should always listen to what they are saying, but you should talk with the customers yourself. This is especially true if your product spans multiple industries and verticals. Sales will almost always promote what their customers need the most and don't always have insight into how you can evolve your product to meet needs for customers in multiple areas.

    2. Iterate on the roadmap based on real-world feedback and evolving business needs.

11. Celebrate success stories:

    1. Showcase success stories resulting from the adoption of product management practices.

    2. Highlight instances where the product approach led to positive outcomes, reinforcing the value of the transformation.

12. Provide ongoing support and training:

    1. Offer continuous support through mentorship, coaching, and additional training as needed.

    2. Address any challenges or resistance promptly and adapt the roadmap and practices accordingly.

       • Listen to what people in your org are saying. Even if you don't agree with what they are saying, try to find a way to make them feel heard, answer their concerns or issues, and include them in the process. They are a part of your organization and deserve to be heard and understood. A lot of times, hearing an opposing point of view can help you refine your process.

13. Measure and iterate:

    1. Define key performance indicators (KPIs) to measure the effectiveness of the product management practices.

    2. Regularly review metrics and iterate on the roadmap and processes based on lessons learned.

       • Always use objective research and data. When you are questioned on why certain features have been prioritized or why the roadmap looks like it does, you have actual data to back it up. It's hard to argue with data and numbers...although people try to do it all the time.

In the end, introducing a product management-led roadmap process and getting everyone on-board with a product mindset is about a lot more than just saying that PMs now make roadmap decisions. There has to be a reason for it, you have to be transparent about what is working and what isn't, you have to be inclusive to make sure that everyone feels like they have a chance to contribute, you have to be willing to iterate when improvements can be made, and you have to have data to back it all up. It is a lot of work, but it is absolutely worth it.

Transforming an organization, especially one new to product practices, requires a thoughtful approach to introducing roadmapping. It requires bringing all functions together and sharing how it helps with overall alignment across the company.

Here are some best practices to ensure a smooth transition for an organization that is introducing roadmapping as a tool.

1. Keep it Simple:

• Build a really simple roadmap that showcases value and builds momentum. Use a roadmap format that outlines key initiatives, timelines, and potential dependencies.

• Begin with a basic prioritization framework like value versus effort or potentially RICE (Reach, Impact, Confidence, Effort) if you are feeling a bit ambitious.

• Focus on short-term goals initially, demonstrating the roadmap's effectiveness in achieving quick wins. Celebrate these wins to build momentum. Iterate based on feedback and the maturity of the organization.

2. Get Stakeholder Buy-in:

• Involve stakeholders from all functions - engineering, marketing, sales, support, customer success, and solution engineering in creating the roadmap. This fosters a sense of ownership and accountability.

• Use workshops and brainstorming sessions to gather input and prioritize initiatives.

• Ensure clear communication throughout the process, addressing questions and concerns openly.

3. Be Transparent and Proactive:

• Communicate the purpose and benefits of roadmapping to all teams.

• Present the roadmap in accessible formats and regularly share updates on progress.

• Be transparent about changes made to the roadmap, explaining the rationale behind them.

4. Iterate on the Roadmap:

• Understand that markets and customer needs are constantly evolving.

• Build flexibility into the roadmap to accommodate revisions based on new information or changing priorities.

• Encourage an iterative approach, where the roadmap is reviewed and adjusted regularly to reflect changing realities.

5. Standardize While Encouraging Innovation:

• Establish a basic framework for the roadmap format, including common elements like timelines and ownership assignments.

• Consider using roadmap software to facilitate collaboration and tracking changes. I have used Aha and Productboard and both are great tools

• Within this framework, encourage teams to explore innovative ways to represent their specific initiatives. Allow space for creative approaches as long as they contribute to clarity and communication.

Some additional things to consider for successful rollout:

• Pilot the roadmap first: Implement the roadmap approach with a single team to refine the process before scaling it across the organization.

• Invest in training: Provide training sessions on road mapping best practices and how to use the tool.

There’s already a planning process in your company, it's just likely a poorly defined/understood one with a lot of downsides.

You might start by doing a learning/listening tour, identifying and aligning team members on the current pain points with planning/lack of planning. 

Then you can explain the reasons why change is desirable, the goals of changing the process, then the new process itself.

When you're ready and have some support/buy-in to adopt a new process:

1. Be sure to define the roles individuals and job functions will need to play in the new process.

2. Set a timeline (and recurring expectations) for the new process.

3. Guide everyone through the new process the first 2 times.

4. Hold people accountable to delivering the artifacts of the process.

5. Communicate often and with detail throughout the process.

6. Do retrospectives on the new process, and be open to valid feedback/criticisms and continue to improve over time.