Ten Ways for Project Leaders to Successfully Navigate Digital Transformation

Suzanne S. Davenport
6 min readJun 14, 2023

In my last blog, I talked about harmful AI development and the rapid technological changes we are seeing. This is particularly true since ChatGPT launched and AI development began increasing exponentially (or so it feels). From my perspective businesses struggle with rapid change and many are totally unprepared for the digital transformation that is happening now. In this blog, I offer ten ways that project leaders can help businesses successfully navigate this digital transformation.

1. As businesses navigate the digital transformation, soft skills, such as active listening and empathy, will become increasingly important.

Difficult conversations have been a constant in the business world and project work for years. Let’s face it, if you pull together a team of super sharp individuals, they aren’t going to agree on everything. And frequently those different perspectives can be invaluable in helping you solve problems, innovate, build competitive strengths, and simply operate the business. Don’t underestimate the value of your project leaders when it comes to solving problems outside of the specific projects they are working on.

2. Risk management systems can be adopted at the organization level — even when there is no project.

For years, I’ve written about the importance of risk management. Sometimes, I still feel like a lonely voice. It’s not that trained project managers don’t understand. I just wonder if other business leaders understand. I almost never run across a new project management tool that incorporates risk management. They are almost always about task management.

This digital transformation will be accompanied by increasing risks, as it becomes harder to distinguish between facts and opinions and to know the truth.

The #ai digital transformation will be accompanied by increasing risks, as it becomes harder to distinguish between facts and opinions and to know the truth. #artificialintelligence #chatgpt #projectmanagement #business #management

3. Procurement contract management can be used to ensure that business leaders understand their responsibilities.

Occasionally, I have written about procurement contract management. It’s a technique that trained project managers have learned. Most larger companies have a procurement department with highly trained specialists, but if you are a small business, you may not have that department.

If you have a trained project manager on staff, consider using them to review any procurement contracts — even ones that are not attached to a particular project. As the digital transformation evolves, businesses will be forced to acquire new systems to compete effectively. Your project managers can be on the lookout for the responsibilities that the business has and the potential or risk from harmful AI development used on purchased or leased software.

4. A well-respected project leader can help you ensure that you are selecting the most valuable projects.

One of the biggest jobs that business leaders have is to figure out how to allocate project dollars. Most business leaders have more ideas than money or time, and so, the question is where to invest those dollars. You cannot do it all. At least, not all at the same time. Focus, focus, focus.

But where should you focus? This digital transformation will bring massive changes that can distract us from what is important. Are you taking the time and the breaks from regular work to consider whether you are still directing your focus on the right target?

I recently read about Matt Emmons — the sharpshooter, who in the 2004 Olympic finals was so far ahead of the competition that all he had to do was come close to the bullseye. And after he fired, the judges reviewed his target and realized he had aimed at the wrong target. He was worried about calming down and forgot to look at the number of the target. Are you focusing on the right target?

A well-respect project leader can you help you review your project investments to ensure that you are putting your money and time in the best place.

5. Project leaders can choose to work in well-defined and focused time blocks.

I recently read something about the negative aspects of using the word sprint — since it suggests a race. I’m not talking about pushing employees to meet unreasonable deadlines or sprinting for two weeks to finish an unreasonable amount of work. I’m talking about breaking your work into deliverables that you can deliver to your client or your management team at the end of some short period of time. Developing a sustainable way of working is critical as we navigate this digital transformation, and I wrote about that in a blog on employee turnover.

Begin your sprint or time block with a well-defined understanding of what you want to accomplish and allow your teams to focus on that work without interruption. You’ll be amazed at what your teams accomplish.

Begin your sprint or time block with a well-defined understanding of what you want to accomplish and allow your teams to focus without interruption. You’ll be amazed at what your teams accomplish. #business #projectmanagement #team

6. Project leaders can be more assertive with business leaders to understand what ‘done’ looks like.

One of my pet peeves is when people work for months on a task without any feedback. We can’t have teams or individuals working indefinitely on tasks without any accountability for finishing it within the allotted hours.

When I see this happening, it is often because the activity requirements weren’t defined well or the person doing the work didn’t break the task into manageable steps. Or, it’s because the activity is too challenging for an individual. In a world where much work requires deep thinking and finding creative problem solutions, we have to be careful that we aren’t overworking intellectual tasks past the point of any benefit to the client.

In my recent book, Herding Smart Cats, I wrote about the importance of understanding what ‘done’ looks like and the sweet spot for challenging people with work that is just above what they know, but not so advanced that they flounder indefinitely.

7. A project leader with expertise in cost management can help leaders understand their cost of employee turnover.

Employee turnover is costly. If we aren’t careful this digital transformation may increase employee turnover as workers simply get tired of the chaos and wear out.

According to Tom DeMarco, in his book Slack, we have no idea how much it is costing us. No one seems to be tracking the cost of employee turnover. And it will vary from organization to organization, and perhaps within projects. I know, as a project leader, I don’t always replace a team member who exits before a project is done. The time needed to bring them up to speed may not be worth the investment.

Once you understand the cost of your employee turnover, perhaps you will realize how important it is to focus on creating a sustainable way of working and a healthy culture.

8. Trained project leaders understand the value of stakeholder and communications management.

Most project leaders will tell you that stakeholder and communications management can be one of the largest parts of any project. It always is for me. And it’s often something I cannot delegate, as I can with issue or risk management, or even cost management.

I want to frequently sit down and talk with various stakeholders, and those conversations aren’t always short, easy, or particularly focused. Sometimes people just need to vent — to be heard. I’ve also found that it takes time to write an email that anticipates the questions that people have. Thinking simply takes time. And we don’t always see thinking as work that has value.

9. Only a handful of your activity deadlines are that important. Focus on those and relax a bit on the others.

When I see a project manager unnecessarily pushing teams to meet every deadline, I see a red flag. This is particularly true on projects which are not exceptionally linear. On those projects, not every deadline will be that important. And teams simply perform better with positive feedback.

When you plan your project, identify the activity deadlines that are critically important and insist that teams meet those. Then, use another set of deadlines as targets to keep the project moving along.

The rest of the activities can be worked into the project as time allows. Focus on planning your sprints well, and delivering the promised results at the end of every sprint.

10. Use cross functional project teams to solve your big problems.

No one can accurately predict the problems that are going to face your organization as harmful AI development continues. And it will continue. But cross functional project teams can be very good at solving problems.

I am fascinated by the rapid development of AI and how it can change and improve our lives. I’m also interested in ways that project leaders and change managers can improve our work and help us cope with this digital transformation. To continue the conversation, please subscribe to my newsletter.

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