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The Peaks and Valleys of Project and Work Management Modernization

The Peaks and Valleys of Project and Work Management Modernization

In my twenty-five-plus years of Project and Portfolio Management, Work Management, and technology delivery it seems the only constant has been change. There is always a new technology, spin on a methodology, market disruption, threat, or opportunity on the horizon that requires us to transform or be made irrelevant. I would venture to guess that you are either currently on a transformation journey, just finished one, about to start one, or maybe all three. These journeys always involve challenging climbs and often deep valleys. 

I have been involved in many varied transformation efforts, but I have led Portfolio Management and work management modernization journeys more than any other. In one particular case, we had been on a portfolio and work management transformation journey for a few years, as we moved a behemoth organization in a heavily regulated industry from a traditional delivery methodology to SAFe, while also implementing the tool and process changes that accompany such a disruption. We had reached the hard part and the organization's resilience was faltering. 

I sat with our VP of Strategy and Planning, whom I greatly respected and enjoyed working for, as he explained to our team that he would no longer be leading us, and our team was to be split into two organizations; one focused on the formulation of Strategy and one focused on the Implementation of that Strategy through Portfolio Management. We were already doing this, but like most of corporate America, this company never met a re-org it didn’t like. After all, can’t all business challenges be fixed with a re-org? But that is a topic for a different article. 

When he asked if there were any questions, my only question was, “Do you believe that the organization has the fortitude to see this transformation through the valley of despair and on to success.” To his credit, he admitted that he did not know. 

If you are not familiar with the term “Valley of Despair” or the “Trough of Disillusionment,” or some variant thereof, you have probably experienced it without being able to put a name to it. A similar idea can be found in a number of service management, process improvement techniques, and consulting practices such as ITIL, Six Sigma, and Gartner’s “Hype Cycle.” 

The concept is this; over the lifetime of a change effort individuals and organizations go through several phases. First, the change is envisioned and begun, followed by a great sense of excitement about the possibilities and inflated expectations. This gives way to the valley of despair, where the reality of the work, the challenges, and the limitations of the change begin to set in. This is the most likely place for the change to be abandoned. 

If the change is failing and/or it becomes clear that the envisioned benefits will not be harvested, this can be a wise decision. Other times, it is simply a lack of resilience, vision, or discipline on the part of individuals or the organization as a whole, that causes the organization to give up. This can often result in setting them back to, or even worsening their situation from the original state. IF the organization pushes through the valley, and the business case remains sound, it begins to reap the benefits of its efforts and eventually reaches a state of sustained productivity and managed growth and improvement. Below is a visual representation of the change lifecycle. 

TroughOfDespaireI agree with, and as I mentioned, have experienced the truth of this pattern but would offer that it is a somewhat simplistic way to envision a multi-year transformation journey, which most Enterprise-wide transformations will undoubtedly be. 

The pattern I have seen played out repeatedly during Portfolio Management Modernization journeys would look more like several of the charts above placed side by side (See my example below)


In this journey of Portfolio Management Modernization, organizations will typically begin with the realization that scope, cost, time, and maybe even quality need to be understood and guided. This will lead to people being hired or worse, existing people being tapped on the shoulder to ensure these things are done, on top of their existing responsibilities. Often, they will be given little guidance or tools at this stage and left to their own devices to “figure it out,” leading people all over the organization to improvise project and work management. 


Eventually, there is a further organizational realization that many of the processes, practices, challenges, and deliverables are similar and repeatable, which leads to localized standardization of these activities within teams or departments. This standardization delivers the first consistent benefits of portfolio or work management, as the low-hanging fruit of efficiencies, insights, and quality are picked. Just beyond standardization, however, we see our first valley of despair. This valley results as ways of working begin to change, standards are enforced, overhead increases, and results, while impactful, are not such that they are truly transformational or potentially even of notable value. Thankfully, this initial valley is typically moderate because the changes are localized to and controlled within the teams or departments and therefore influenced with relative ease. 


Once through this valley, the real work and long climb begins, identifying and institutionalizing best practices beyond individual teams and across the organization. This is particularly challenging as this may be the first time in the journey that influence and agreement outside of individual teams or departments is required. Additionally, ways of working that may have only recently been adopted will likely need to change again to make way for the practices that will be adopted by the entire organization. Because these changes are so wide-reaching and begin to require additional collaboration, coordination, and toolsets, if not already in place, this pitch of the climb is often accompanied by a centralization of portfolio and work management and the deployment of PPM and work management tools. Successfully making it to organizational standardization is virtually impossible without strong Executive leadership and a willingness to invest in the required personnel and toolsets. 

An interesting side note is that the lifespan of a centralized portfolio management organization and that of a CIO are similar and, at least anecdotally, seem to be connected. If a Portfolio Management function cannot prove its value within 2-3 years, it will likely be collapsed and the lifecycle often begins again as new leadership comes in to “right the ship.”

Because the changes during this portion of the journey are so impactful, so far-reaching, so disruptive, so costly, and require such influence, even once the level of standardization is reached, the valley succeeding it is the deepest and longest in this journey and the most likely place this transformation will fail or be abandoned. Additionally, at this point in the journey, many become aware that the next pitch of the climb to become a higher-performing organization, optimized to take advantage of holistic, data-driven, strategic portfolio investment decisions and adaptations, is next on the horizon. It is here that perseverance begins to wane but is critical to obtaining the envisioned value. 


The next pitch will lead us to Integration. Here, the organization will build upon the standardized practices, processes, and uniform, related data by integrating systems and processes across the organization. Take heart, however. Although technically challenging and potentially one of the longer climbs, this is also arguably one of the more interesting pitches of the climb. It is during this portion of the journey that all the work that came before begins to truly pay off and people across the organization begin to see and enjoy the benefits of the connectedness of the systems, data, processes, and even the people. Questions become easier to answer. Insights and patterns emerge more quickly. Ideas that previously seemed impossible or even inconceivable become not just possible but within grasp. And value begins to compound on itself. 


However, we have one more valley to traverse and one more pitch to climb before we reach the summit. Post-integration organizations will often experience a lull in the excitement and momentum, resulting from a learning curve and a plethora of ideas and opinions regarding what to do with this newfound data and connectedness. Sometimes the amount of information now available and the number of possibilities can seem overwhelming, making it difficult to select and deliver the right priorities. If we continue onward and upward, however, proactively identifying and taking advantage of opportunities to use the data to provide insights, we begin to move into the realm of Optimization. As we optimize the organization we can look up and out, focusing on the horizon rather than myopically on the immediacy of the tasks at hand. 

In my opinion, this is where the really cool stuff starts to happen. The organization is now aligning virtually everything they do to Mission and Strategy, driving effective, holistic, data-driven, strategic portfolio investment decisions and modifications through Portfolio Management best practices. They are utilizing fully integrated real-time planning and operational portfolio data, and a culture of continuous improvement, all with information captured through the natural flow of work to inform decisions at every level. 

At this level, we are focused on managing excellence, looking to the future, but with an eye on the past and present. Current and future investments are under constant evaluation and alignment within the context of the changing environments within and without, to proactively maintain value-delivery commitments, and continuously improve and optimize to deliver the optimum set of investments to achieve Mission, Vision, and Strategy. 

To get to the modernization summit and become a truly high-performing organization, as we have explored, is a journey with several peaks to climb and valleys to cross. But there is a well-trodden path to complete the journey successfully and obtain the desired value. As encouragement and a bit of guidance, I would offer this:

•    Know that the climbs and the valleys exist
•    Realistically plan and prepare for them 
•    Realistically prepare others for them
•    Persevere 
•    Know the journey is worth it 

Having a guide on your Portfolio and work management modernization journey can help make it as easy and rewarding as possible. If you have questions or need help envisioning the possible, understanding the value path, developing your roadmap, or connecting your systems, data, processes, and priorities to achieve your goal of becoming a higher-performing organization, please feel free to reach out to me or schedule a conversation or demo. I would love to hear what I can do for you. I am happy to be of service.

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