I love the leverage you get when strategic planning is working well.
At Rally, I run our strategic planning process with help from Jean and others in our organization. We have experimented with many agendas, internal facilitators and guests, but we’ve found the most success when Jean facilitates these meetings and I lead them. It is challenging work and we try really hard to create a setting that leads to magic and allows the best to emerge from the group. As you might imagine, if you know Jean and me, we never stop trying to improve the process. In addition to our desire to keep advancing, the context at Rally keeps changing. Whether from growth, hiring, market changes, maturation of agile, or changes in customer demographics; our overall setting for strategic planning keeps shifting. It is a difficulty that we wrestle with, but knowing it is ultimately unsolvable, we have learned to embrace the dance.
I do not recall what was the chicken and what was the egg, but we started working on strategic agile topics last year and it launched two efforts and blog series: N Levels of Planning, and Scaling Agile to the Strategic Level. In this post I am bringing the two series together to explore tooling the process of strategic planning in an agile context with Catherine and Ronica. Larger Rally customers and past employers have shown that managing a strategic plan in a spreadsheet creates vacuums. Through our efforts at Rally, we have learned that trying to maintain strategic alignment with our development teams without a single source of record to visualize variances on plan versus actual is challenging. (HINT: Slides are not a very capable source-of-record :)
It is difficult to integrate big-bang, waterfall planning/stage-gates and traditional budgeting with effective agile teams who keep learning and adjusting. It is even more difficult to stay on course as an agile organization without effectively closing the feedback loop on roadmap/strategic planning efforts. In the first instance, it is easy to simply be driven by a naive plan. In the latter, it is easy for the development effort to drift apart from the goals and direction.
These well-validated difficulties led to the birth of Project Stratus and the N-Levels of Planning efforts at Rally. These two initiatives are intended to help increase the effectiveness of strategic planning in an agile context. They are helping us balance the need for forecasting delivery while also benefiting from the fast feedback that flows out of agile teams and programs. We like to talk about this process as steering realistic roadmaps to maximize the delivery of value.
To explore this problem space, we diligently carried out discovery and validation exercises that led to a working application (Project Stratus) and a service offering (Agile Strategic Planning) that we use to ensure the delivery of a Whole Solution. Through our customer interviews, we found that the most common strategic planning solution when doing agile development is a strategic planning person holding the plan of record in an Excel spreadsheet. This spreadsheet holds some form of a roadmap of releases, programs and resource allocations. It is updated on a regular cycle, typically quarterly. However, two major problems exist with the spreadsheet approach.
- The plan is outdated as soon as the work starts because there are two sources of data; one for planning and one for tracking progress
- Planning in a vacuum happens as correlating the empirical data into a highly customized spreadsheet leads to outdated data which tends to erode trust
As a result, this most common solution is horribly disappointing with human translations that lead to over-aggressive estimates and/or status updates progress reports. Bringing agile values into this faulty process will shorten feedback loops and bring real data effectively into the cycle.
In exploring the space, we are discovering multiple ways that organizations manage the strategic planning process. As we are still making sense of these patterns, it is early to report on our findings. However, one approach does stand out.
The model articulated in Dean Leffingwell’s newest book, ”Agile Software Requirements: Lean Requirements, Practices for Teams, Programs and the Enterprise“ is clearly one of the patterns of agile strategic planning. You can see a snapshot of this method on his blog, but if you really want to learn it, you should get his book. It is a clear articulation of how to manage your strategic priorities as series of releases. The book breaks the problem into three agile requirements management areas: the team, the program and the portfolio. The beauty of this approach is how it trains all levels of product owners, product managers and portfolio managers to run in agile unison. Dean developed this model starting with the teams and working systematically up through the enterprise portfolio level (ie bottom to top). And, importantly, Dean worked this iteratively through a number of his consulting customers over the past decade (see the Big Picture section of his blog to the incremental progress laid out over time).
In addition, in Agile Software Requirements, Dean has described a “business epic kanban system” which he uses to make the work in process visible, understand the state of epics as they transition to development, and to get the portfolio planners on a similar agile page as are the agile development teams. He and a number of our customers have used this system effectively in a number of large enterprises, so we know it makes a good starting model for portfolio/strategic planners who run portfolios as a sereis of releases.
As a result, this model of strategic allocation and roadmap planning is proven to work well for agile teams that ship code series of releases. Here is Dean’s model from that book and his web site.

Big Picture: Scaled Agile Delivery Model by Dean Leffingwell
We have a number of customers making very good progress in developing strategic roadmap steering capabilities using this approach and Rally’s Project Stratus. If you are interested in this approach paired with Stratus, consider contacting Dean or Ronica, our services owner, directly or through your Rally Account Manager. (See Ronica’s contact information below.)
We will continue to explore hybrid waterfall/stage-gate, other hybrid agile (scrum/kanban), and continuous flow techniques for strategic planning in the coming months. Please stay tuned.
Finally, to fully explore the problem and solution space, we created the RallyON conference. We will host this conference in Boulder on May 10th and 11th. We limited the conference to 150 attendees and it has sold out quickly to our most active users and champions. Don’t worry if you are not attending as there are a number of ways to engage in the conversation including:
- Responding to this post with your challenges, ideas and comments on strategic planning in an agile context
- Sharing your opinion or challenges related to topics that Rally Coaches, Technical Account Managers and Product team members are posting for the conference on our new Coaching Blog.
- Posting your agile, scrum, kanban and xp questions on pm.stackexchange.com or programers.stackexchange.com to have a the community formulate answers to your questions prior, during and after the conference. We will have expert users from both of these stackexhanges on site at the conference to help us leverage this rapidly growing community.
- No matter what choice you make, please tweet your efforts with the #RallyOn11 hashtag. It will get the attention of the Rally coaches, technical account managers and product team, in addition to all the physical and virtual RallyOn attendees.
Please join us online before during and after the conference to explore the topic of strategic agile.
About the authors:
Ryan Martens is a member of NRDC’s Environmental Entrepreneurs, founder/CEO of the Entrepreneurs Foundation of Colorado, and Founder/CTO at Rally Software Development.
Special Thanks to Catherine Connor, the lead on Project Stratus at Rally and Solutions Evangelist Ronica Roth, who owns our Services strategy at Rally.You can reach Ronica at ronica[at]rallydev.com