Waltzing with Da Vinci

the role of design thinking in project leadership

Monica Croy, Senior Associate, Point B


Da Vinci represents the ultimate project leadership paradox. The greatest thinker of his time, Da Vinci, was notorious for not completing projects. Arguably, his greatest work was his notebook in which he sketched designs of helicopters, scuba gear, cameras, plumbing, military armanents, and human anatomy. Although he delivered few innovations, his designs sparked centuries of innovative projects that transformed the world we now live in. Design, without project leadership, cannot transform the world we live in.

After World War I, France invested heavily in building the Maginot Line, protecting its borders from future invasion. Deemed a successful project, it met all the requirements of defending against infantry-based trench warfare. As World War II broke out, French leadership was very dismayed as German tanks and aircraft “waltzed” around the Maginot Line and captured Paris in days. Project leadership, without design, cannot transform the world we live in.

The Importance of Design Today

Exhibit 1 – The Importance of Design Today

Background – What is Design Thinking?

Design thinking is human-centered innovation (Brown, 2009, p62). It represents a set of concepts used to create some of the most innovative products over the past 20 years: The iPhone, eBay, and iPad are examples of innovation that tapped into human needs and behavior, pushing the boundaries of product/service strategy and development. These solutions would not have been introduced without the process of design thinking. Design thinking is now being applied to some of the most complex issues we face today: world hunger, sustainability, and health care delivery. It is no longer confined to a department or role; it is changing the very face of leadership.

Design thinking employs an iterative and collaborative approach to taking on business or societal challenges. It pushes beyond our familiar project management methods of iterative development and deductive problem solving. It brings together people from different disciplines to explore new ideas and envision solutions that are more human centered and more viable for successful execution. Imagine a help desk clerk, your market research analyst, a product design specialist, and the logistics expert augmenting your team as you wrestle with the next major scope issue affecting your supply chain system.

Design thinking works off three basic concepts, as shown in Exhibit 2. Inspiration fuels a leadership team's drive to observe “what's going on” inside and outside the organization and “what's going on with the customer.” Ideation translates those trends and needs into ideas and actions that the team can take. It is here where design research helps bridge intuition with evidence so that executable but meaningful actions are produced (Fulton, 2008, p 53). Implementation_represents the known world of project management tactics to drive those actions to results. Implementation tactics augment our known management practices around iterative development with new concepts—like storytelling to drive stakeholder alignment and business readiness around a concept and parallel thinking to get multiple teams to attack the same issue from different perspectives.

Processes in Design Thinking

Exhibit 2 – Processes in Design Thinking

The Role Design Thinking Plays in Project Leadership

Today's project management discipline has evolved to deliver predictable and consistent results. The toolkit to manage scope, resources, effort, quality, and schedule has allowed us to bring the focus and control needed for consistent project delivery; yet, change continually hits the project leader. Our organizations are bombarded with changes in regulations, competitive landscape, labor, and the business partners we rely on for delivery. Customer needs and perceptions change at the speed of light.

Our project management toolkit has struggled to keep up. We have developed new methodologies (e.g., agile) and broader risk management frameworks to identify issues earlier, respond quicker, and increase our flexibility to adapt to changing conditions. Even with these new methods, today's project managers still often find themselves a step behind, reacting to the external and internal threats facing the project. As Exhibit 3 illustrates below, these dynamic forces create real challenges for the project manager to solve:

Challenge #1 – The solution no customer needs

A public sector Enterprise Resource Planning (ERP) project team “awakens one day” in testing to find new rules that need to be configured as the result of last night's collective bargaining agreement. A product company in the last stages of development discovers a competitor has beaten them to market with a competing product. An insurance claims project finds out that they have just been bought out by another company, and a new leadership with a new vision will arrive soon. These common occurrences put the project manager in a game of Russian roulette—to go forward with a product no one wants or to bring the momentum to a “screeching halt.” Our first response typically is to “defend.” We fall back on the last sign-off, the last stage gate, or our requirements to fight a losing game of scope management. The big challenge: Could we have done anything differently or influenced the outcome if we had seen the change coming earlier or better understood what the customer needed?

Challenge #2 – Business case hijacked by competing project

An outsourcing project steams through planning. A new leadership team arrives. The new CEO previously implemented a solution for one of the organization's business partners. His “old guard” convince him that they can adopt the older system and achieve greater cost reduction and customer service quality benefits in a shorter time than the outsourcing project. Particularly in a tough economy, organizations facing often drive parallel initiatives seeking to improve its survivability. These parallel initiatives compete for the scarce resources aimed at meeting that business target.

As project managers, we look to our portfolio management processes to protect ourselves against such conflicts. When these fail, we sometimes tighten project controls even further, locking in resources and requirements. The big challenge: Could we have stepped back from organizational politics and evaluated which initiatives will deliver what the customer and/or organization truly needs?

The Disruptive Challenges Change Brings Project Management

Exhibit 3 – The Disruptive Challenges Change Brings Project Management

Challenge #3 – Stakeholders pursue the next “bright shiny object”

A clinical information system project team is preparing for system conversion and deployment of a key billing and accounting function. Concurrently, several stakeholders get an unsolicited demonstration from a hardware vendor of hand-held wireless tablets that would boost their bedside productivity. Despite the great progress in testing, key stakeholders of the clinical information system project begin to lose focus and support for the system in favor of pursuing hand-held wireless tablets that would boost their bedside productivity.

Faced with this challenge, we often pursue the traditional route of tightening the governance process, watching the impact of delays caused by late decision making, and instituting a new operational readiness assessment process. And yet, these key stakeholders may have uncovered a missing piece of patient workflow that could dramatically enhance both the patient's experience and increase the accuracy of billing/accounting. The big challenge: How could we have reconnected to the customers’ needs at a time when our project team craved stability and rigor?

Challenge #4 – Resource brain drain when you need it most

An insurance claims project team is attempting to deploy a new self-service application aimed at increasing the customer experience. An unplanned acquisition is announced. Suddenly, the key stakeholders and subject matter experts are pulled into due diligence activities and the project stalls. This very common occurrence leaves the project management team pursuing schedule and scope negotiations with project sponsors. The big challenge: Could we have confidently allowed the project to pause while key resources determined the potential impact the acquisition may have had on the business?

Challenge #5 – Teams barricade themselves

A once collaborative cross-functional health care process reengineering project finds many closed doors, as the health care institution balances significant operational cost cutting with efforts to position the health care institution for health care reform and stimulus dollars. Team members renew their parochial ties to their operational owners. All grounds for productive collaboration disappear in the swirl of “nos,” “no ways,” and “nevers” heard across the project floor. The project management team pursues the traditional routes of clarifying and managing hand-offs between work groups, having forced team building sessions, and increased deliverable monitoring. And yet, the changes embodied in both the cost cutting and health care reform could have direct boosts to the charter of this reengineering effort. The big challenge: Could we have admitted our internal change management problem, and agreed to re-charter the shared vision and plan among team members and stakeholders?

The Promise of Design Thinking

These challenges may represent some of the more “wicked problems” facing projects today: there is no clear root cause and certainly multiple competing solutions. As project managers, we have been taught to decompose and solve problems into more manageable “chunks.” Pursuing this path, however, reduces the overall chances for a successful implementation like the founders of the Maginot Line discovered in 1940.

The promise of design thinking extends the project manager into project leadership, where the science of management and art of leadership come together for breakthrough results. Design is change. Design thinkers are leaders who love to challenge the status quo, embrace complexity, and synthesize solutions rather than “decompose them.” They use art, metaphor, and analogies to provoke inspiration around form, function, feel, and experience. Through this process, they break down a solution, while at the same time generating new options (Raney, 2010, p 36). Even within the pressure cooker world of project management, design thinking has its place. Design-thinking concepts allow us to better understand the customer and the world outside the project walls, expand our peripheral vision on threats and opportunities that will define project success, and envision more complete and adaptive solutions to issues and risks we deal with on a daily basis.

Rising to the Challenge with Design Thinking

The opportunity for leaders in our discipline is to find faster, better ways to meet these challenges. What can we take from design thinking to help toward this end? The strategies to employ design thinking concepts can be categorized into two levels: what we can do systematically_at the project level and what we can do individually as project leaders.

Project Strategies to Enable Design Thinking

Exhibit 4 – Project Strategies to Enable Design Thinking

Project Strategies

#1 – Inspiration: Modify Your Governance Model to Allow for Big Picture Thinking

We design governance models to resolve issues, make decisions, and build ownership. We build capacity for big picture thinking during planning and then shut it off quickly to drive scope, schedule, and business readiness. Our main communication link with our steering committees becomes the status report, which is hardly the vehicle for big picture thinking.

Design thinking reminds us of the need to really understand the customer and the trends in the ecosystem impacting the organization. During any stage of a project, we have the opportunity to re-ground our decision makers in what is happening outside the organization and what impact those changes may have on our project. Tactically, we can seize this opportunity by:

  • Bringing decision makers into front-line customer activities to reconnect with customer perceptions, behaviors, and needs.
  • Establishing customer presence at the governance table itself.
  • Conducting formal external assessments aimed at understanding trends outside the organization.
  • Changing exit criteria at key stage gates to evaluate the impacts of project actions and decisions on the outside world.

Activities like these have a dual impact. First, they intentionally create opportunities to “look up and out.” Second, they begin to create a new sense of behavior and responsibilities for key stakeholders to consider the “outside world” in the daily steering of the project.

#2 – Ideation: Adapt Your Team Engagement Model to Promote Ideation

A team engagement model refers to the way the team engages internally with stakeholders, users, and the outside world. Some engagement models are very hierarchical and rigid. Some are fluid and peer based. Our typical team engagement model is to break down the work, assign the work based on skill and competency, and drive the teams toward successful delivery of their expectations. Teams engage only when there are hand-offs that require formal collaboration.

Some of the challenges we have discussed require cross-functional and inductive (i.e., “white board”) thinking. Tactically, we can strengthen ideation and collaboration by:

  • Redesigning issue resolution teams to bring in outside perspective, such as a devil's advocate or an outside part of the organization to help bring fresh thinking to the table.
  • Using parallel issue teams to attack an issue or risk concurrently during the analysis and recommendation/mitigation activities from different angles before landing on a single path forward.
  • Changing the questions we, as leaders, ask of our issues teams, balancing the common questions of “what caused it,” “who's affected,” and “what's the answer” with a new set of questions like “what business conditions helped foster the issue,” “what is the full range of answers possible,” and “what would the customer say is the preferred answer.”
  • Using 360 risk assessment activities to probe on how the project will stand against different business scenarios and what actions the project would need to take to respond to those business scenarios.
New Metrics Considerations

Exhibit 5 - New Metrics Considerations

The success of activities is really measured in how the conversations around issues and risks change. You can look at what questions and ideas were examined to get to the best answer, who asked the questions, and how long the answer will stand the test of time.

#3 – Implementation: Expand What You Measure

What we measure often drives what we discuss with our team members, sponsors, and stakeholders. We end up evaluating delivery against scope, schedule, resources, quality, and effort. If we take a balanced scorecard mentality, we might pick up additional nuances—like how project morale is progressing, how much ownership is the business demonstrating, and how well we are addressing integration across the project work streams.

Most of the measures focus on the project, not the solution. Great designers consider a different set of attributes when generating a new design. They may look at attributes like proportion, contrast, novelty, scale, and depth to evaluate whether their design is effective.

These types of metrics have a place in our project management dashboard too, as Exhibit 5 illustrates. We enhance the conversation with our teams and stakeholders when we evaluate not only how we are delivering but also whether we are delivering the right solution. We can monitor:

  • Novelty - how novel our solution is against what is happening in the marketplace.
  • Integration - the integration of our solution across the business.
  • Rhythm - the rhythm of our development or quality assurance process (do we speed up or slow down?).
  • Scale - the expected scale of our customer support and deployment efforts.
  • Depth - the depth of our team's product expertise and capabilities.
  • Proportion – the size of the solution to the magnitude of the business problem.

These additional metrics provide another avenue to look at how the solution and the team are proceeding. It may also help re-instill sponsor and stakeholder support for the envisioned outcomes of the project. Perhaps more important, we can catch key issues and risks affecting adoption and benefit realization before the solution is delivered.

Project Leadership Strategies

If you have the systems in place to use design thinking on your project, there are key tactics you can use as an individual to exploit the creativity of your team. Below are four suggestions for where to start.

#1 - Mind Map Your Project Plan

Project leaders have been trained and have largely honed the skill of creating a comprehensive project plan; as a tool, it is critical for our discipline. However, a natural outcome of creating a project plan from a linear, time-based perspective is time bloat. The cascade of dependent, integrated, and related tasks often leads to “project bloat.” Deliverables appear as necessary to get from the beginning to the end, but in reality are not customer-consumable. Do we need them? What about the time it takes to hand off from one team to another? Is that valuable to the customer outcome? Every project leader has been told to “sharpen your pencil,” compress timelines, and reduce deliverables. How can you know what to remove?

An option for creating a project plan to attack some of these issues is to start your work plan from a “mind mapping” approach. Start by describing project success from the customer, stakeholder, and end user perspectives. This starting point immediately puts you in your customer's shoes. Then, instead of working backward along a timeline, work out; in other words, imagine, or physically place, project success in the center of your page, and create tasks that radiate out from success. Different spokes can be different work streams or deliverables required to create the success center. This project map will have the effect of illuminating your critical path as well as your path to project success criteria.

Applying the Mind Map to a Project Plan

Exhibit 6 – Applying the Mind Map to a Project Plan

Most project leaders fear the use of brainstorming for anything except a last resort. Brainstorming gets too many ideas on the table at one time, promotes impossible solutions, and raises unmanageable expectations, but narrowing the field of vision early or consistently to just possible “solutions” limits the team's ability to find the new and innovative. Sometimes the narrowing will bring the project team to a complete standstill on the most difficult issues.

Creating boundaries for brainstorming can help the project leader through the concerns of using brainstorming to resolve issues. The tactic is to create and agree on a set of boundaries to evaluate ideas from the brainstorm. Typical criteria include:

  • Attributes of what the successful solution will include
  • Cost of solution
  • Time boundary—both to generate ideas and time to assess solution options
  • Stakeholders who will be decision makers for the solution

#3 - Creative Thinking Hats

Project leaders and team members sometimes need “permission” to think outside-of-the-box when trying to define a project or resolve project issues. One tactic to grant this permission is to use the Lateral Thinking technique of “Six Thinking Hats,” as defined by Edward deBono. The concept is to deliberately take on a new perspective defined by the color of the hat, to allow the team to see a problem from a new perspective. Project teams have used the six hats to encourage new perspectives, generate new ideas, and minimize blocking factors.

The Six Hats are:

White: facts, figures, and objective information. White Hat thinking focuses on observable, checked and proven facts, and avoids interpretation or any perspective that jeopardizes neutrality.

Red: emotions and feelings. The Red Hat gives the wearer permission to bring feelings into the conversation so that they can be explored as a different perspective.

Black: negative, pessimistic assessment. The Black Hat can point out the potential failures and negative elements in an idea.

Yellow: optimism, construction, and positive “what if.” The Yellow Hat is the opposite of the Black Hat, creating space for exploring value and benefit.

Green: creativity and new ideas. The Green Hat is tasked with both the questioner and listener roles to explore ideas that could move things ahead.

Blue: facilitation and control of the thinking process. The Blue Hat's role is to be conductor, choreographer, or the director to ensure that all the hats are used at the right times to make progress.

The way many project leaders use the hat technique is to specifically ask project members to use a hat to bring that hat's perspective into the problem-solving scenario. Each hat is tasked with a specific perspective, which is likely different than both the perspectives normally represented by the teams and the perspectives normally represented by that team member. It sounds like the project leader saying: “We seem stuck in the numbers of this issue, who will volunteer to take a Yellow Hat and who can take a Green Hat perspective?” or “That solution seems okay, but let me try this Red Hat thinking out on it….” The team generates ideas that wouldn't have come up otherwise and has the opportunity to expand their thinking.

The hats can also illustrate blocks in teammate thinking, in which certain types of thinking are being overused by the project team. Is there too much pessimism? Ask the team to put on their Green or Yellow hat for an hour. Are facts and figures overwhelming the solution options? Ask the team to use their Red hat to consider which solution option might fit. Try a perspective shift and see what possibilities open up.

#4 – Prototyping

One of the key ways that designers learn is by prototyping. When working with complex, unbounded challenges, designers “test early scenarios quickly with real users in their environment…using concrete, provocative prototypes to uncover new learnings. These prototypes allow designers to eliminate unviable options early in the process’ (Raney, 2010, p30).

Creating small, easily tested models of the product or solution allows end users to interact with the solution prior to a significant financial investment being made in implementing that solution. This early input can help the project leader better understand how solutions will play out and adapt them to better meet the need. On our projects, we can experiment with the final solution in a few ways, each with different applicability and different rewards.

  • Break the entire program into smaller, shorter, easily managed parts. When the smaller projects are all aligned and synchronized with the full solution, they give the team quick wins with lots of forward motion.
  • Implement process changes without system changes. Process changes are usually less expensive and can create positive demand for the new solution by allowing end users to test out the business process changes before they have a tool.
  • Get users and stakeholders involved for whiteboard prototypes. Map the tool's user interfaces on a whiteboard and allow them to mentally test them against their current job. Design changes are possible earlier, before end users are disappointed.

Discovering ways to prototype your solutions will create greater and early alignment with stakeholders and give the project leader a creative path to project completion.


Project leadership, coupled with design, have the potential to transform the world we live in. Although no panacea, design thinking provides project leaders with a new dimension to understanding the changing conditions that surround their project and envisioning better solutions to some of the most troublesome challenges facing our projects. It can bring together the intuition and insight of Da Vinci and synthesize real solutions that not only work but meet the needs of the people we serve.

Brown, T. (2009). Change by design. New York: HarperCollins Publishers.

deBono, E. (1985). Six thinking hats. Toronto: Key Porter Books Limited.

Dust, F., & Prokopoff, I. (2009, Winter). Designing systems at scale. Rotman Magazine, 53–56.

Fulton, S. J. (2008, Winter). Informing our intuition: Design research for radical innovation. Rotman Magazine 53–57.

Martin, R. (2009). The design of business: Why design thinking is the next competitive advantage. Boston, Massachusetts: Harvard University Press.

Neumeier, M. (2009). The designful company. Berkeley, California: New Riders.

Raney, C., & Jacoby, R. (2010). Decisions by design: Stop deciding, start designing. Rotman Magazine (winter, 2010), 35–39.

This material has been reproduced with the permission of the copyright owner. Unauthorized reproduction of this material is strictly prohibited. For permission to reproduce this material, please contact PMI or any listed author.

©2010, Brian Turner and Monica Croy
Originally published as a part of 2010 PMI Global Congress Proceedings – Washington, DC



Related Content


Publishing or acceptance of an advertisement is neither a guarantee nor endorsement of the advertiser's product or service. View advertising policy.