Scott Shippy work management
February 20, 2019

Advice from a Work Management Expert: Scott Shippy, PMO Sr. Director at Viasat

This is the first post in our new series about masters of modern work. Subscribe to our blog to get on-the-ground advice from work management experts like Scott Shippy, PMO Sr. Director at Viasat (featured below).


Scott Shippy never set out to be a project manager.

He started his career in broadcasting, then moved into IT, followed by working as a software developer. But something about these jobs didn’t sit quite right with him. It wasn’t until he stumbled across the Project Management Institute (PMI) that he discovered his calling. Reading their definition of project management, he realized he was wired for the field, given his interest in relationships, organization, and communication. So he pivoted.

Since that time, Scott earned an MBA in technology management, maintains his PMP certification, wrote a book on project management, and is featured in Done Right. Over the course of three decades, he’s gained extensive experience and is a source of wisdom on the topic.

One of the primary pieces of wisdom he promotes is that project management experts must be willing to admit when they’re wrong — even if they’re a veteran in the field. Scott says that for him this means that despite his decades of experience in project management, he believes he’s likely still wrong at least 20% of the time (though he says his spouse of nearly 25 years will claim it’s higher).

He writes, “What leads to wisdom is learning and applying that last 20% where we make our mistakes. Wisdom comes from experience, its failures, its successes, its mistakes, its joy and its sorrow; but most of all wisdom comes from dropping pride long enough to seeing oneself as we really are — and improving from it.” This principle reflects the title of his book, The Last 20%: Perfecting Project Management in an Imperfect World, a book filled with anecdotes and learnings from his life’s adventures. He advises young people to “take those moments of being wrong. Learn from them. Admit to them. Own them, and move on.”

Scott’s suggestions go well beyond admitting mistakes. He also encourages people to ask “why?” at least five consecutive times after a project failure, peeling layer by layer to understand exactly what went wrong. In the same vein, he encourages people to expect that projects will not go according to plan, citing what he calls Scott’s Law: “If there is a 50% chance of something going wrong, then 9 times out of 10 it will!”

Above all, Scott believes in the importance of communication, saying, “90% of my job is communication, with the remaining 10% being the actual work.” He adds, “What most people do not realize is that it is the responsibility of the person communicating to make certain the message that was given was understood.” To this end, Scott errs on the side of over-communicating messages. For instance, when his team had to change project management methodologies, he made sure that his team “heard the same message 8 times, but in dramatically different ways.” This included a teaser email message, a formal email announcement coupled with a visioning document, an hour-long kick-off session, a formal training session, a testing and review session, a refresher meeting that answered new questions, an audit session to ensure understanding, and ongoing mentoring until the transition was complete. This repetition made the change smooth.

That said, Scott believes that it’s also crucial to not change for the sake of change. “Change can easily become a crutch for not implementing change correctly,” he writes, acknowledging that sometimes change is the wrong way forward. He adds, “Without change we can never grow and improve. However, never underestimate the power of stability!”

“If there is a 50% chance of something going wrong, then 9 times out of 10 it will!” — Scott Shippy, PMO Sr. Director at Viasat

During our interview, we talked about all these things and more — including the distinctions between project management and work management, what to look for in a system of record for work, and the best advice for people starting out in the field.

Below is a transcript, edited for length and clarity.


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What advice do you have for young people who are starting a career in work management?

The most important aspect of my entire education was learning to understand how I am internally wired. I am a person who loves puzzles. I love taking complex programs and ideas then turning them into reality. I like starts and ends. Bottom line, I am a consummate project manager, and I love it.

So my advice is to try out new things and figure out what fits your personality. Don’t worry about staying in the same job your whole life. As a matter of fact, by the time you are 40, hopefully you have had 3 or 4 jobs.

Try new things. Take risks. Make mistakes. Have failures. All of these will lead you to your passion and understanding of how you are wired.

Generally speaking, what aspect of work is most challenging today?  
Focusing on the correct work to be done. Social media has moved us toward a new manner of thinking where we believe we need to look at everything all and do everything. Sometimes the greatest aspect of work management is focus. Doing a few things right all of the time, and building upon those successes is far more important than doing more.

What’s the biggest challenge you face when implementing work management tools?

Adoption is always the biggest challenge. I often joke that everyone wants a good project manager until they have one. The same can be said for work management tools. Everyone wants a good work management tool until they get one.

Tools of this nature take time, care, and feeding. They’re only as good as they’re used and supported.

Everyone wants a good project manager until they have one. — Scott Shippy, PMO Sr. Director at Viasat

Too many people think that adopting these tools will be a silver bullet that will automatically do the work management planning and execution for them. That’s simply not the case, and the ongoing challenge is coaching people that these tools still require the best skills that program and project managers provide.

The tools themselves are like glasses. They sharpen the optics, improve communication effectiveness, and clarify the message. On their own, work management systems are no more useful than a pair of glasses sitting on a night stand. In other words, I would not say that work management systems, in and of themselves, make anyone successful. They are, however, a key tool in a leaders chest of tools to be successful.

Tools allow you to scale. They allow you to not spend so much time maintaining your processes. That’s why they’re essential, despite the challenge of adoption.

What do you see as the difference between project management and work management?

Project management is about getting compartmentalized pieces of work across the finish line and making sure everybody is joining you at the same time to complete a specific initiative. It's sort of like herding cats, as the saying goes.

Work management goes beyond the project. It includes business as usual — ongoing activities that occur in a cyclical nature. Work management focuses on how you keep the business running in an efficient way day in and day out across the organization.

Why did you move toward a system of record for work management?

Our move toward a new system of work management wasn’t done on a whim or to follow the latest trend. Rather, it was born out of a necessity to standardize and implement tools that facilitate repeatable processes, transparency to status, accountability, and formal systems that support partnerships during escalations rather than encouraging the traditional finger pointing and blame game. It was a decision to manage all work across the company.

What were you drawn to in a work management tool?

I was drawn to work management tools that can be configured — not customized — to meet business needs. This allows me to be flexible and ensure that the tools are less important than the actual work that needs to be done.

Interesting. Why was the distinction between configured and customized important to you?

I wanted a configured tool because it allows me to control my own destiny. I can try new approaches more easily. I can quickly succeed and fail. Configured tools allow me to mold features to fit my needs on my own.

Customized tools, on the other hand, require hard coding of the system from a third party. What happens with customization is that people say, "Oh! I have this bright idea!" Then they wait six months, get it customized, and say, "Shoot! They gave me exactly what I was looking for, and it doesn't work!”

It’s much better to be able to experiment on your own terms and adapt quickly.

So what are the most critical processes that need to be in place before someone fully adopts a work management tool?

First, have a process. Implementing work management tools before you've given any thought to process is usually doomed for failure. I've seen companies do that. They buy a product, thinking it's going to solve all of their problems, and they don't realize there was a certain amount of blood, sweat, and tears required before installing the tool. Personally, I implement all process on paper, manually, before I implement a tool.

"It is the responsibility of the person communicating to make certain the message that was given was understood.” — Scott Shippy, PMO Sr. Director at Viasat

As far as specific processes, I’ll go with the PMI three: scope, schedule, and cost.

Scope requires you to list the problems you're trying to solve. Not in paragraphs, not in books, not in volumes. Just simply list the problems you're trying to solve.

Schedule requires you to ask when do you need to get them done. This coincides with prioritization. Certain things need to be done sooner than others. Scheduling is a matter of taking your bulleted list and putting those items in order.

Finally, cost requires you to ask how much time and money you should give to solving any one of the items on the list.

When you figure out these three dimensions of process, things run a lot more smoothly.

What are the most critical features of an effective work management tool?

These tools should support collaboration, communication, and accountability. I’ve touched a bit on the first two, so I’ll elaborate briefly on the third. A good work management tool does not allow people to hide. Any tool that allows a person to not be accountable or hide their accountability is a failed tool.

What advice do you have for someone who’s interested in work management tools?

Make sure you know that every situation requires some tweaks to the tools you use. In addition, unless you are working in a strict environment, where repeatable processes are required by regulation, sticking to one tool or approach is rarely effective. Having a good set of tools that can be used in a variety of ways allows leaders to assess the need and fit the right approach to solving the problem each time.

A great work management tool is more like a Swiss Army knife that can be used by leaders in creative ways each time it is pulled out.

What is the single biggest thing you think people who aren’t in work management get wrong about work management systems?

People who do not agree with work management systems often view these tools as supporters of bureaucracy and the waterfall methodology. In a sense, it’s true. But it isn’t necessarily bad. In fact, I hate to tell you, but we live in a waterfall world. Life is a progression. We have contracts. We get up at relatively the same time every day, step through the same steps and go to bed, all in a roughly the same predictable manner. Life is a waterfall. Life is a process.

However, I believe that properly implemented work management systems bridge the gap between the waterfall world we live in and Agile efficiencies we strive to bring into the workplace. Work management systems and Agile, SAFe, or DevOps are not diametrically opposed, but rather, complementary.   

Finally, what do you think is the most important work skill to succeed in the future?

Communication. Those who can effectively communicate and take accountability for their decisions will be those who own the future. With the advent of worldwide social media, it’s harder and harder to hide the truth, and that’s why accountability and integrity are becoming a key component to being an effective communicator.


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