Nov 8, 2018 - Justin Emond

Five Keys to Digital Project Success for Large, Federated Organizations

Third & Grove primarily works with mid-market and enterprise clients, and many of them have complex stakeholder ecosystems that have to be actively managed during a project to ensure success. When we need to navigate a tricky situation, we find ourselves going back to these five principles.

Stay focused on your goals

The two most important professional pieces of advice I have ever gotten came from rather different sources: a TV show and a speech by a business owner.

The first bit of advice came from Scrooge McDuck in an episode of Duck Tales I watched when I was 8 or 9 years old. The second, and the one relevant here, came to me in a speech I read by Charlie Munger, Warren Buffett’s business partner, vice chairman of Berkshire Hathaway, and possibly the wisest person in the world.

Charlie’s advice was dead simple, powerful, and has helped me over and over again: “Start with the end in mind.”


One of the important paths to project success is to start with and stay focused on t key project goals. Clearly identifying the goals at the start allows you to work backward and ensure that your proposed digital strategies and design changes are focused at all times. This focus ensures the best return on investment.

This is especially crucial when you’re dealing with many stakeholders because the goals can be used as a means to control feedback and discussion. They are a common reference point for vetting ideas, and helpful during reviews.

A CEO once said, “If we have data, let’s go with that. If all we have are opinions, we’re going with mine.” Don’t mismanage your project and enable that CEO.

Use proactive project management

One important strategy for effective project management is being proactive. If you have a client that struggles to make decisions, you can flip around the standard playbook of emailing, “Hey can we do this?” to “You have two options, X and Y, and these are the pros/cons of each. We are proceeding with X in three days unless I hear otherwise from you.”

Used effectively, this approach can be absolute magic. One of two things will happen: They will be motivated to make a decision quickly, or they will stay silent, in which case you get a decision anyway.

Committees are where decisions go to die. Proactive project management is especially useful in these situations.

Use stakeholder committees

I know, I know. I just said committees are where decisions go to die. But, they do have some utility when managed properly. Managing stakeholders effectively is all about taking control of the conversation to maximize the utility of their feedback, both in how it can improve the final outcome for the client, and stop that feedback from derailing the project.

A stakeholder committee is a great way to achieve these goals. You can create one, or multiple committees. Just make sure to define who is on the committee, what areas of the project they will be involved in, and the key points in the project when the committee will be brought together. You need to control the agenda for each meeting, run each committee session, and steer the group toward the feedback you need.

This allows you to use the committee structure to handle information flow, deal with any dissension (a vote, if necessary), and maintain project momentum.

Anticipation problems before they happen

Outstanding digital project managers have one trait in common: They would make terrific 19th-century British butlers. Why? Let me try to explain through a movie.

There is a terrific period piece film called Gosford Park that focuses on the dynamics between the servants and the wealthy people in a rich British household. (Spoilers ahead!) A central character is murdered, and in the film’s climax, you find out that one of the servants actually murdered this character because they had figured out that another person was going to kill him; by doing it first; he was protecting his client.

Now, I’m certainly not saying to use murder to smooth out a complicated project. But this rather extreme example is illustrative of how important it is for a project manager to constantly be on the lookout for problems and be proactive in solving them.

When you foresee an issue and have a solution ready to deal with it, you seem prescient to your colleagues and they will be very impressed. The best part is that it’s not hard to do. Like most things, the important part is the doing. Just take a moment to ask yourself, “What could go wrong, or what could someone object to, or how a meeting could go bad?”Whatever you are working on next in the project, just briefly think, “How could this go sideways?”

This skill is especially useful with large projects, because as the number of stakeholders on a project increases, so does the number of problems. Why? Because communication nodes exist between all stakeholders. With just two people, there are only two nodes of communication (A to B). But with four people, there are suddenly six nodes (A to B, A to C, A to D, B to D, B to C, C to D). The more people in the project, the worse it gets.

Why do more communication nodes matter? Because each of those communication nodes is a potential for a miscommunication, confusion, or an expectation gap to appear in the project. The only way not to be overwhelmed with issues is to constantly be vigilant about what could go wrong.

The old wisdom is true: Hope for the best, plan for the worst.

Accept that the obstacle is the way

Every project has problems, and with a many-stakeholder project, you are going to have some especially, let’s say, interesting ones. There will come a point when you have a gnarly problem that you can’t process away. You are going to have to face it head on and deal with it.

In Meditations, a memoir of sorts by Roman emperor Marcus Aurelius, he writes, “The impediment to action advances action. What stands in the way becomes the way.” But the title of a recent book puts it more simply: The obstacle is the way.

You must forge a solid relationship built on integrity and kind honesty with your single point of contact (SPOC) on the project. You have to be willing to have a come-to-Jesus moment with your SPOC when an issue needs addressing. Unaddressed problems are about as productive in digital projects as they are in marriages.