Fall 2020
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Why Box-Checkers Don’t Check the Box
Why strategic project managers are worth their weight in gold.

Project management has come to be viewed by many as a skill that employees can perform without necessarily having deep expertise. In fact, many companies and even consulting firms operate as if every consultant on staff can be a project manager. While it is true that basic project management can be easily taught or mimicked, the true value of project management is achieved only when you deploy project managers (PMs) who are strategic in nature and not just “box-checkers.”

Unfortunately, too many PMs address projects by simply checking the boxes of their required PM methodology. They complete the required phase gate deliverables and develop timelines, RAID logs, and status reports. But the content is shallow and does little to propel the project forward, solve the business problem, or mitigate issues and risks.

This type of PM could be called a “box-checker,” one who focuses on checking the boxes of the methodology or how the project will be delivered. By contrast, a PM who is more strategic in their approach—who focuses on the what and, more importantly, the why of the project being delivered—can be thought of as a strategic PM. While neither are formal titles or credentials, of course, they do give us a terminology for thinking about the different levels of value each brings.

The strategic PM still checks all the boxes in the PM methodology but with a different intention and purpose. Projects delivered by strategic PMs in your PMO will consistently be delivered with a high degree of quality, minimal post-delivery issues or defects, and happy stakeholders. But do not fret: The box-checker PMs in your PMO, with the right coaching and deeper knowledge, can be trained to think more strategically and up their game.

Strategic PMs fundamentally approach projects in a different way than box-checker PMs. The strategic PM leverages the PM methodology to propel the project forward and control costs and timelines, while also focusing on understanding, articulating, and socializing the what and why of the project. By nature, these PMs are curious, ask tons of questions, and soak up knowledge that the subject matter experts and stakeholders provide. They seek to understand the business problem and easily engage in brainstorming and deep-dive discussions. They can drive workshops by asking leading questions, convey complex topics in an understandable fashion, and ensure alignment to the business needs. Strategic PMs can stand at a whiteboard and field top-level questions of any dimension—architecture, technology, business impacts, value, etc.—without having to turn to the subject matter experts. Their understanding allows them to participate in the solutioning process, thus helping to minimize misunderstanding and avoiding reworking, while also guarding against unnecessary delays and cost overruns.

Because of their natural curiosity and propensity to dive deep into the content of the project, strategic PMs can clearly articulate the major concerns, pain points, or “gotchas” to be addressed. They can work side by side with project counterparts, SMEs, and senior leadership to vet and resolve issues. They can clearly articulate the various perspectives of stakeholder groups and drive understanding of the consequences of potential designs, delivery approaches, or deployment plans. Key stakeholders’ input will always be invaluable but can often be a siloed perspective without the wide-angle lens of the strategic PM.

The ability to drive business decisions between multiple groups who often have conflicting points of view is a key attribute of a strategic PM. While that attribute tends to come naturally to a strategic PM, it can be encouraged and developed in box-checker PMs. Box-checker PMs will need additional content and functional training in addition to coaching and mentoring. With time, however, they can begin to think more strategically.

The box-checker PMs in your PMO, with the right coaching and deeper knowledge, can be trained to think more strategically and up their game.

Two neighborhood picnics

Consider how differently a neighborhood picnic might be organized using each of these PMs. Sure, each picnic would have the basics covered: food, drinks, tables/chairs, music, games, plates, napkins, etc. Yet the experience of the guests would be dramatically different.

Think of the box-checker as your overextended friend who volunteers to help but does not have much experience planning large events, as opposed to a strategic PM party planner who has done this type of work professionally for years and has the time to focus on its success.

The strategic PM likely would develop a complete menu considering each guest’s dietary needs and then would vet that menu with some key guests. In contrast, the box-checker might offer a simple, easy-to-cook menu without considering appropriate options for children, vegetarians, or guests with gluten-free diets.

As for music, the strategic PM may spend hours compiling a family-friendly playlist that will seamlessly provide fun music to get the party started and keep it going. In contrast, the box-checker may need to wing it and jump through various song requests, some of which may be inappropriate for the audience, playing them from a phone that runs out of power halfway through the party.

Unfortunately for the partygoers at the box-checker’s picnic, there are plenty of tables and chairs, but they are across the park and away from all the action during inappropriate-for-children party games. At the strategic PM’s picnic, the party games, which were researched, planned, and tested, are right next to the main party pavilion and surrounded by comfortable chairs with blankets to keep guests cozy in the crisp fall air.

Both picnics delivered what was typically expected, but the guests had drastically different stories to tell the next day. Certainly, your overextended friend could have planned the same party as their strategic counterpart, but they did not have the time or experience to think through all the different components.

Another major difference is that the strategic PM has mastered the art, not just the science, of project management, including the necessary soft skills. Studies show that PMs who learn to master soft skills to supplement the hard skills are the most successful.1 Strategic PMs most likely have been taught to use social skills and awareness to build solid relationships with project team members and key stakeholders, thereby strengthening their project leadership effectiveness. They learn how to communicate effectively within an organization’s culture and how to foster a collaborative environment that allows team members to communicate openly and honestly. Since most project employees do not report to the PM, this skill is critical to motivate teams to keep them moving toward the common goal.

Back at our neighborhood picnic, we can see these soft skills in action as the strategic PM engages with each guest, checking in to make sure they have what they need to enjoy a fun day and directing them toward other guests who have common interests and hobbies. The strategic PM orchestrates the various aspects of the day, while being mindful of the wants and needs of the guests and adjusting plans as necessary.


So, what role does methodology play in all of this? A robust methodology may include several phase gates, sign-offs, and detailed deliverables to ensure effective management and reduce risk along the way. Even the most robust and ironclad of methodologies, however, are not enough to overcome the gaps and shortcomings of a box-checker PM. In fact, in many organizations, the project methodology may have become bloated with additional steps, deliverables, or sign-offs implemented in response to quality, cost, and time issues on projects historically run with box-checker PMs. In contrast, running projects with strategic PMs may allow an organization to streamline its project methodology and simplify deliverables in addition to sign-off and approval processes. A strategic PM will bring gate meetings to life by actively facilitating a robust discussion focused on highlighting key risks and resolution of issues rather than a rote readout of project status.

Understanding that a strategic PM is critical to your success, how do you make sure that’s what you are getting? While there is certainly value in certifications such as the Project Management Professional (PMP), you cannot solely rely on it or a person’s years of experience to determine whether someone is just a box-checker. When evaluating a potential employee for the role of strategic PM, ask plenty of questions to enable you to evaluate the depth and breadth of understanding of what they have delivered, the problems solved, and the resulting impact to the organization in terms of people, processes, and technology. Also ask questions to evaluate their understanding of the impact on—and implications of what was delivered to—key stakeholder groups and whether the business benefits were realized or measured.

With any of these lines of questioning, if the candidate focuses on the processes or “how” things were done, they are likely a box-checker PM. In contrast, the strategic PM will be able to clearly and concisely articulate these items from the perspective of business and/or technology leadership.

A place for both kinds of PMs

Is there a place in your organization for the box-checker PM? Yes, in fact the box-checker can provide critical support for your senior strategic PMs working on large, complex projects or programs. The box-checker will provide additional capacity to strategic PMs by helping them complete project methodology documents, develop status reports, push approvals, and gate sign-offs. The strategic PM would provide the content and final reviews of these items, thus ensuring robust and clearly articulated content. Also, during this time, the box-checker PM can shadow the strategic PM during key stakeholder meetings and while developing key deliverables to learn how to be more strategic. With the correct training, coaching, and encouragement, box-checkers can begin to see projects in a different light and approach the methodology with a different goal in mind.

In the end, a project delivered by a strategic PM will result in fewer post-project issues and defects because the entire executive team will have been well-informed and appropriately engaged in decision-making and risk mitigation along the way. Yes, you will pay more to staff your PMO with strategic PMs, but rest assured they are worth their weight in gold! And if you are a box-checker PM, seek out a strategic PM and learn from their ways as though they are your sensei.

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