New Articles

Start With The ‘Why’: How Good Project Leadership Drives A Digital Transformation

digital visibility acceleration

Start With The ‘Why’: How Good Project Leadership Drives A Digital Transformation

The term “digital transformation” has become embedded in the business world’s vocabulary for companies large and small, as more of them incorporate technology to streamline their processes and customer interactions.

Recent research shows 61% of IT decision-makers agree that the global pandemic forced their organization to begin or implement a digital-first strategy. It’s a big step of change for any company, and having the right project leadership in a digital transformation is crucial to navigating chaos, organizing a business and winning the battle for customers, says Denise Brinkmeyer (, author of Project Orienteering: A Field Guide For Project Leadership and president of Jump Technology Services®.

To simplify and coordinate what can be a complicated process, she says a digital project leader’s first step must be establishing the “big why” behind every aspect of the project.

“Asking and clarifying answers to ‘why’ questions must happen at the start of every project,” Brinkmeyer says. “If you haven’t defined and fully understood context and purpose, your project will be increasingly vulnerable to all the challenges it will meet along the way to completion.

“There will be pressures and conflicts, there will be temptations to go off track, and there will be some delays along the way. That’s what makes it critical to be clear at the outset about why a specific project should be pursued. Ensuring that you’ve done your best with this first step will also enable you to act as your project’s salesperson, ensuring stakeholder investment and support all along the path to completion.”

Brinkmeyer has these tips for project leaders when determining the “big why” during a digital transformation:

Know your constraints. Brinkmeyer says three primary constraints – time, cost, and value – give focus and concreteness to any project vision. “Knowing, for example, that you can’t mandate overtime unless you’re outsourcing work is important to establishing a realistic project timeline,” she says. “Having a grasp on your constraints helps determine how to convert the project’s wish list into objectives that can actually be achieved. As the project leader you’ll have to coordinate resources, address potentially conflicting needs and concerns, and problem-solve. For those reasons, you need a very strong sense of the why that motivates and joins all the pieces together.”

Ask these questions:

Why do you want to do this project? Brinkmeyer gives an example of one answer to this question, geared to what current or potential problem a company is trying to solve: “We must have a new system, so that if we don’t hire more staff and we take on more customers, the work can continue at the same level of quality.”

She says a project leader’s job entails both having a strong sense of the whole with its parts and articulating all of it so that the entire team can understand and act on it. “The words we use to articulate the big why matter dramatically to a project’s trajectory,” Brinkmeyer says.

Why are these the proper objectives for the outcome you seek? In the end, the project leader needs to prove that the project has been successful, which means they need the ability to measure results accurately. “Asking ‘why’ can help clarify the relationship between objectives and vision,” Brinkmeyer says. “You need to provide a clear context for your objectives. The more you leave open to interpretation, the more vulnerable you leave the project to expensive detours and even failure.”

Why are these the people to help you achieve your goals? Brinkmeyer emphasizes spending time finding a vendor whose initiatives and capabilities actually suit your project. And reference-check your vendor options. “Find out if they’ve told the truth about their past projects,” she says. “Then, when you interview vendors directly, ask them, ‘Based on your history, when are we going to start receiving value from this project?’ And be wary of the promises attached to a single, mammoth system that’s said to take care of all your needs. It could take years to learn and implement.”

Regarding the core team in the company involved in the transformation, Brinkmeyer says the project leader’s goal is “to inspire and motivate the people you’ve been given in order to make possible the most positive impact for your project. The question, ‘Why are these the people I’m working with?’ needs to be followed with, “Knowing how they work, how will I activate them to achieve the project goals?”

“Setting yourself up for project success begins with establishing the big why behind your vision and objectives,” Brinkmeyer says, “so that the way you explain it and what you really need come together for the sake of the project’s success.”


Denise Brinkmeyer ( is the author of Project Orienteering: A Field Guide For Project Leadership and president of Jump Technology Services®. She has over 20 years of diverse business experience with various-sized companies and develops business consulting service strategies. Brinkmeyer focuses on the development and implementation of software project management and software design methodologies that dramatically increase both customer satisfaction and department performance.