Business transformation means different things to different people. Today, the common definition describes a program or initiative that will help an organization respond with digital enablement to either marketplace or customer-centric opportunities. Project management offices (PMOs) are well positioned for these transformation projects because they are often inseparably linked to the IT Department, the centralized engine for business change. Coaching functional leaders, project managers and executive teams during a business transformation implementation remains a top role for the PMO leader. But, how can you lead your team to digital transformation success?

In Hot Pursuit of “Business Transformation”

Let’s look to the pros for some insights on transformative team leadership. Famous Aussie hockey coach Ric Charlesworth mused, “The interesting thing about coaching is you have to trouble the comfortable and comfort the troubled.” If that sounds like your company, you’re not alone. Peter Taylorfrom The Lazy Project Manager cites the same old status quo processes as being one of the main hurdles in managing business transformation. In short, change can feel uncomfortable and risky, even when it’s absolutely necessary. However, the comfort of the way we’ve always done things can be overcome with appropriate solutions wielded by confident PMO leaders.

The need for business transformation might not be so obviously plotted for many naysayers among the ranks, particularly when it appears as risky as a three-point shot. However, the risk is not necessarily in the change, but in the mismanagement of that change. That’s where this paper comes in. In his book, How to Get Fired at the C-Level, Peter Taylor describes how mismanaging change is the riskiest move of all – and the number one reason for executive termination. Change management is extremely challenging at all levels, but every challenge presents yet another opportunity. Many of the risks associated with change also pose opportunity for transformation and growth not just for the c-suite but for all those involved in business change.

We aim to arm you with the information you need to turn these problems into opportunities and undertake a successful business transformation while also positioning your PMO as a well-tuned engine built to successfully drive crucial, strategic change. You will be able to coach change management partners and clearly define the features and benefits needed from your software solutions. You’ll have actual examples from people who’ve been there to underscore your commitment to the goal to help your PMO become more than just a box-checking organization.

Most importantly, you will have the confidence to lead the charge. As legendary head coach of the Dallas Cowboys, Tom Landry said, “Leadership is a matter of having people look at you and gain confidence … If you’re in control, they’re in control.” Change management is a question of controlling the forces of order and keeping the forces of chaos at bay. Let’s get started.

The Winning Business Transformation Process

Business transformation programs, by their very nature, are among the highest risks in the portfolio. But as we noted in the introduction, it’s usually a matter of mismanagement of the process and lack of buy-in. That’s why leadership must structure a solid change management program or partnership at the outset. The most important thing to gift your change agents, according to PMI, is “the authority to stop and start projects, to control the pace of implementation and the pattern of program plans according to the behavioral aspects of change.”

KEY POINT: PMOs aren’t meant to lead the change management programs — business leaders must. PMO leaders must prove the changes are being implemented with unremitting excellence. As the famous coach Vince Lombardi said, “Perfection is not attainable, but if we chase perfection, we can catch excellence.”

We’re All in this Together

Peter Taylor, author of The Lazy Project Manager, has run four global PMOs and has been the leader of business transformations in several industries. Here are the three steps he suggests you take to jumpstart your own business transformation:

1. Solicit the best partners you can to help you create a structure for the program that supports both innovative direction and project objectives. In many cases, the structure will be agile, because that’s how companies best respond to digital dynamics among customers and in the marketplace. Your partners include decision-makers in virtually every function in the company, the people with the budgets and the resources to enable the change. PMOs and their partners must be armed with the ability to execute on benefits while reporting back to project sponsors when they’ve hit a roadblock.

2. Get people on board with a single, strong transformation champion to follow is job number one. No one will have a single definition of what transformation is in your company. The PMO leader is the person at the table who can do so objectively—he or she has no skin in the game and, Taylor says, will thus be able to focus intently upon how: “The portfolio should be entirely and absolutely connected directly or indirectly to the strategic intentions of the organization.” C-Suite leaders and other powerful executives must show unremitting support for the goal — so PMO leaders must illustrate the steps toward the goal using watertight metrics and analytics for planning.

Remember that the PMO leader is also at the table to help delineate governance and strategic guardrails for go, no-go oversight after the program is implemented. Something that may surprise you? Keep-the-lights on projects, such as infrastructure expenditures, are absolutely in tune with strategic vision and must be planned for at regular intervals, so your changes have a road to run on. Just like star athlete Michael Jordan coaches: “You can have all the physical ability in the world, but you still have to know the fundamentals.”

3. The PMO needs to be the driver of change because it will be able to work with multiple departments to ensure the right people are on board. Large scale collaboration requires PMO-centric transformation. They can help everyone rally around the “what” more than the “how” because even though they may own the “how” in the form of the portfolio itself, they must be outcome-focused. With this complete visibility, executives and collaborators of every stripe gain insights to drive execution of the right projects using the right resources to work within budget at the exact right time.

Four areas to ensure you’re doing the right things in the right way:

People – As stated earlier, getting the right leaders and change management partners on board at the PMOlevel will be job one. As Phil Crosby, celebrated English footballer and coach said, “Selecting the right person for the right job is the largest part of coaching.” In our experience, it’s important to ensure that your change management capabilities are up-to-speed but don’t expect the PMO team to be completely in charge of the process. That’s not their place and can alienate others in the company and damage the PMO, as well. When the change management imperative isn’t given its correct resource allocation, it can become a fringe activity that can fall by the wayside. If that happens, you’re setting yourself up for failure.

Processes – Much of what the PMO will do is explain the whys and hows of business transformation projects to project leadership and sponsors. Taylor predicts difficulties ahead when there is no training program for these sponsors and their PMO-based counterparts. For business transformation to work, everyone must have the same definition of success. Investing in training will pay off richly in the end.

Performance – Identifying what success looks like for your industry, as well as which projects in your PMO bring the most strategic value, will be different for everyone. Accountability assignments to each facet of success in the phases of transformation projects allow your teams to drive forward, together. As the saying goes, teamwork divides the tasks and multiplies the success.

Promotion – One of the most interesting things about leading a business transformation program in the PMO is watching things fail and making lemonade out of those lemons. PM experts, when given the right freedom, know that failures can uncover the most valuable characteristics of their companies — and uncover the threats to their existence. During business transformations, ensure that you shut down anyone who engages in the name, blame, shame game. Your failures, if handled appropriately, will help the company change and grow — the very definition of “transform.” As PMI coaches, “Another important aspect of every transformation program should be to learn from mistakes. Here, the lessons learned, more than in other situations, are vital for adopting a continuous improvement approach.”

Use Technology to Conquer the Competition

For change transformation to take hold, all of the projects and programs in your project portfolio management (PPM) solution must be aligned with your strategic vision. Your software selection is key because it will drive organizational value every day. Even the cultural alignment between your enterprise and your choice of technology solution will aid in the integration and the speed of the transition. Gifted sports trainers not only know the name of every muscle they’re asking you to work but also why it is important for creating the mechanics and strength you need to succeed in any given sport.

Right Fit Solution

Can your existing project and resource management solution deliver the strategic value that your business demands? You might want to take a close look at a few crucial capabilities and work through them in priority order. Many solutions on the market are able to help in certain areas, but few are a good fit in all the areas that you need to succeed. It is important to balance and prioritize features, gain an understanding of what is most important for your team and what are “nice to haves” to understand a best fit solution to get you the transformation your business requires.

When looking for a solution to help support a business transformation goal, here are a few areas to consider:

An accurate skills database that will get you the right tool in hand to drive your transformation initiative. Resource management issues cause more damage than nearly any other PM element.

Lifecycle management capabilities to handle any capacity surges you’ll face during a business transformation project. This includes managing projects beyond completion for the duration of their lifespan. Sometimes this includes maintenance and upgrades, phase 2 approaches and even end of life of activities.

Reporting. Executives and any other stakeholder will be needing insight into the transformation and progress toward goals. Executive reporting will get you far in keeping the right people energized and engaged. Give the people in power the information they need to remain confident and become an advocate for the value your PMO brings.

Ease of use is important when considering solutions. The system is only as good as the data in it, and if no one will use it, you are back at square 1.

Benefits tracking to ensure you are managing to outcomes, not just at the activity level. It is important to use actual data for forecasting and adjustments.

Implementation Partner

Is there a quick-start program or team included with all of the technology enablement and training you should look for when arming your PMO to be business transformation leaders? A successful person never loses — they either win or learn. Before, during, and even after implementation, it is key that your solution partner comes in with a solid definition of how change programs require advanced organizational synchronization and a plan to get there. They will understand the dependencies between different initiatives, as well as business-as-usual processes and activities to activate the system in a way that best sets you up for success. They understand the life cycle of change, and have expertise in ensuring that transformation programs are resourced effectively through the different stages of your programs.

Measure to Avoid Risks

In sports, as in project management, “Coaches have to watch for what they don’t want to see and listen to what they don’t want to hear.” — John Madden

When you manage change through measurement, you’ll be able to use intelligent governance metrics to coach through the transformation. Predictive analytics and intake templates that make measurement easier are two of the top features of a solution. Also, make sure your assessment phase includes measuring the success of the following elements of most change management programs:

    1. Understand which business process model to adopt and set the functional framework
    2. Define offer drivers and the objectives of offer evolution and simplification
    3. Define an end-to-end solution architecture that considers all systems and integrates the change program with business-as-usual projects
    4. Map requirements to process frameworks
    5. Define business case objectives and priorities

Once you’ve aligned these elements you must have a centralized place where everyone can see the key metrics. This will put everyone on the same page and allow you to keep the transformation process moving forward.

It Works If You Work It: Grace Under Pressure

During high-risk transformation activities, we’ve seen one thing that characterizes effective teams: their ability to connect strategy to delivery — guardrails and governance for transformation. Turn your data from your PPM into information and that information into knowledge. Then you can make strategic decisions that lead to transformation.

One of our clients worked hard to change their siloed company into a well-oiled, services delivery machine. In healthcare, especially, their needs were tightly linked to the success of their digital transformation. They were able to get their arms around the actual challenge only by being absolutely clear-eyed about their own shortcomings.

Once they understood reality on the PMO level — what resources broke down when and how their customer and marketplace demand across geographies fluctuated and why — they were able to harness meaningful change. Thanks to solid executive support across country and divisional functional units and IT, their PMO was able to share the good, bad and ugly — and act accordingly, with the whole company behind the charge.


At their simplest level, projects are the management of change. Once you make sure your vision for every project aligns from the C-Suite down, using top-down strategic technology, you can set your team up for a championship season of more frequent change.

Large change projects are daunting because of their promise and their pitfalls. Once you learn that these programs boil down to what most projects need: doing things the right way, in the right order, for the right reasons — but also possess elements that significantly reduce execution risk — you’re well on your way to mastering the transformation life cycle. Vince Lombardi said, “The only place that success comes before work is in the dictionary.

Back to Driving Business Transformation.