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  • Sarah Freiesleben

An "Inconvenient Truth" About Strategic Initiatives




In 2019, I left the corporate world after spending 13 years working in increasingly senior positions on complex strategic enterprise tech projects that all "delivered" on their project KPIs, yet implemented systems that made the business suffer with countless workarounds, duplicate data entry points, misaligned data, and sometimes such poor functionality they had to be replaced ASAP. I left with a burning desire to drastically improve the way we execute strategic change initiatives. The failure rate for transformation initiatives is cited to be at around 70-85%, yet we have more experts, consultants, and sophisticated project management methodologies than ever. Getting trendier PM certifications, hiring more expensive consultants, and implementing fancier technology will not solve the root cause of this problem. We need to fundamentally change how organizations approach change and how they measure project performance.

Common Approach to Change: Strategy consultants recommend a portfolio of programs to implement the strategy; these programs get fed into the project portfolio pipeline, initiated, and planned for execution. Soon after, large teams are ramped up and all too often face a high variation of opinions about what the scope actually is. Some understand they are implementing a software, others believe they are transforming an organization and its processes; chances are they are trying to do all of the above, but without being empowered to be adaptive. Spoiler alert: This is a recipe for disaster.


Ironically, as the projects begin to show signs of problems, most leaders begin to think their projects are understaffed or the project team lacks the right skills, even when they are in fact overstaffed and many of the needed skills are present in the team but not being used. They believe this because managers often report resource constraints as the cause of much more nuanced problems because they lack the reporting mechanisms and freedom to tell the real story. You can’t fit “the project team is confused because the strategy they are trying to roll out has various contradictions & competing objectives” into a traffic light report. Upon hearing of the resource constraints, the leadership approves more resources and hires in more consultants. The vicious cycle continues. Project Performance Measurement: Project KPIs are generally reduced to quantitative targets focusing on time and cost. Quality is involved, but mostly in binary terms: “Did we complete the test cases successfully (y/n)”; “Did we fulfil the requirements? (y/n); “Did we train the users? (y/n)”. However, understanding the true quality would rely on answering more complex questions like, “Did the test cases represent real life scenarios?”; “Do the requirements clearly articulate the business value that is trying to be achieved?”; “Do the users understand how and why to use the system?”. Projects are filled with nuances which the constraints we use to manage them do not permit. This creates a sad reality where the truth speakers become the outliers.


How can we drastically improve? The unexpectedly simple way to improve both levels of problems is to engage more effectively with the humans inside of your organization. Just because we are more often than not implementing technology as a means to achieve a strategy, it is time to stop believing technical experts and systems are the solutions to our most strategic problems. The humanities disciplines give insights into navigating complexities that projects fail to take into account; such as: narrative, nuance, integration, and context. Paying attention to what makes us human is critical to successfully running an organization that will survive the future, and this cascades into how we run projects.


It is critical not to misunderstand this point, I am not suggesting the popular theory that leaders all just start relying on their gut instincts. In fact, I am suggesting quite the opposite: I am suggesting that we purposefully work to incorporate the insights from academic subjects such as linguistics, cybernetics, complex adaptive systems theory, anthropology, biology, complexity science, logic, literature, philosophy, religion and literature into how we navigate the more complex initiatives in our organizations. This points to practicing situational sensemaking, conducting coherent safe to fail experiements, pulling innovation practices into our "normal" business functions, building contexts where emergence is likely to occur, listening to learn from other points of view, incorporating the requisite variety of people into discussions, etc. To get a bit more specific, I will briefly explain what this could look like in relation to drastically changing the two main areas influencing strategy execution.


Adaptive Change Initiatives: Instead of making every project have fixed, predictable deliverables even when some of the elements are unpredictable, create adaptive change initiatives for the more complex strategic change ambitions. This means that your "transformation program" itself does not have a predictable fixed TO BE state but rather a shared understanding of the desired future state expressed in qualitative terms. You can then break down the initiative into more predictable parts to be run as projects: implement software X, re-structure parts of the organization, etc. Adaptive change initiatives will include the requisite variety of stakeholders from the beginning as participants who help influence the pattern shift toward the envisioned future. You will have open and honest conversations together in order to build an initiative you all buy into. These initiatives will still be measured, but they will be measured by whether or not they are trending consistently in the right direction instead of with black and white targets.


Allow for "true quality" in projects: Once you have projects running, the openness needs to continue in order to be able to allow for true quality. Leaders need to have the courage to ask the real questions and be open enough to hear the answers. And here is the most surprising part: they need to be open to hear the answers from a larger variety of the team than they expect.


I read so many job ads searching for project managers who challenge the status quo. Yet every PM I have seen who does that (including myself) has suffered the consequences. It is time for leaders to realize that if they want different results, they need to be willing to hear the truth from within their projects, even if it isn't fun or convenient to them. If the strategy is misaligned, your project manager is not going to be able to fix that. But they need to be able to make you aware of it, without being afraid of the consequences.


If you are a leader in an organization that suffers from projects that do not deliver business value or that are disconnected from the strategy the company wants to achieve, some key questions you could ask yourself are: Are we setting our programs & projects up for success in the way we scope them? Are we allowing our projects to aim for true quality or are we restricting them in our efforts to be robust? Are you tolerating ubiquitous project failure by falling into the convenient trap of believing your project managers just are not good enough or that it is someone else’s “fault”?




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humanITsync  •  Copenhagen, Denmark  •  Sarah@humanITsync.com  •  +45 3173 0396