How to Succeed at Digital Project Management

Pro tips from a PM that’s been there

There’s plenty of advice about how to be a successful project manager that focuses on the basics of project planning — managing scope, resourcing, and budgets. But what if you’re ready go beyond the basics, and level up your PM skills?

Here are some practical tips to ensure your digital project is a success,
tried and proven from my own experience over years deep in the trenches of agency life.

If I had six hours to cut down a tree, I’d spend four hours sharpening the axe — Abe Lincoln

Every project has constraints — find out what those are early in the project, and make sure all stakeholders are in agreement. Understanding constraints gives you the freedom to explore the space you have to work in and helps define priorities.

The classic PM decision triangle balances scope, time, and cost, and can be summed up by asking: Do you want your project to be done good, fast, or cheap? Pick any two — but you can’t have all three:

Play along or share with stakeholders

You know what they say about assumptions…

… but really

There are things we are aware that we know (known knowns) and things we know, but not consciously (unknown knowns). Then there are things we know that we don’t know (known unknowns) and things we don’t realize we don’t know (unknown unknowns).

Handy visualization via:

Assumptions are the unknown knowns, but they can be become known knowns by asking good questions.

  • Why do we think that?
  • Why does it have to be hosted here?
  • How many people are actually visiting our site on mobile?
  • How did the designer come up with that estimate?
  • Will content be ready by that date?
  • Do we have the technology and expertise to meet these needs?
  • Why does this project exist? Why does it need to be done now?

Asking the tough questions as early as possible forces good thinking and can dispel assumptions before they get a chance to wreck your plans.

Different projects require different approaches to planning, but one thing that’s guaranteed on every project is that plans will change. A new priority springs up, a developer has the flu, your website gets hacked by the Syrian Electronic Army, or some other unknown variable arises to complicate what should have been an easy task.

Even when plans change and schedules slip, they still add value to the project. They provide an opportunity to expose assumptions, clarify agreements between people and organizations, and to help team members see how their role fits in to the larger picture.

Knowing that unknown unknowns are inevitable, plan to be adaptable to change, and open with communications.

  • Extra resource hours in the budget? Create a bucket of contingency hours ahead of time, to dole out as needed — you’ll find a way to use them. Build in more or less contingency hours in new projects plans depending on how familiar you are already with the technology, how clear the requirements are, and experience from previous projects.
  • Check in with the team regularly so you understand the status of all the moving pieces, and be transparent about any potential impact to the overall schedule. Sprint planning for Agile teams encourages this in many ways, but any team can (and should) be doing daily stand-ups at a minimum.
  • Be flexible to change— while the deliverables and milestones themselves may not change, their placement on the timeline might. Get creative, make trade-offs, and keep everyone up to date on the latest schedule.

One of the biggest challenges as a PM is also one of the best benefits. Working across functions and departments, you get to learn and understand all aspects of product development. But, you also have to figure out how to motivate and inspire people who don’t report to you, and might not even understand what the project is about.

My approach to gain respect and get people on board:

  • Be transparent and open. Make sure everyone knows how their role fits into the project and roadmap, share the high-level picture, and where you currently are. You’re the ambassador to the team with the 10,000 ft view to let them know what’s going on and why their contributions matter.
  • Focus on clear communication. Particularly with internationally distributed teams, and technical discussions, things can get lost in translation. It’s easy enough to ask someone to clarify or take notes, and worth it in the long run.
  • Be respectful. This should be a no-brainer. You catch more flies with honey — people are more likely to help if you ask nicely and listen to understand.
  • Be proactive in helping people. Don’t know the answer to something? Information is boundless, so be resourceful— ask a developer, ask a stakeholder, get people that can help each other in touch. Search bug reports and documentation for clues. Ask Google or Quora or StackExchange. Pay attention for trends or patterns, and learn to anticipate where the gaps will be.
Step up and be the person people come to for help.

Attentiveness. Pay attention. To everything. All. The. Time. The best PMs I’ve worked with succeed because they really care about all aspects of a project and take action on anything that keeps the project moving.

Help write test cases or acceptance criteria. Click on all the things and make sure the links go to the right places. Try the new social login feature you’re adding. Check the design in a different browser, then on your phone, then on your co-workers’s phone. Don’t ship products with major bugs.

Include QA engineers from the beginning of a new project and updated all along the way, so they can write accurate test plans and know when something is not working as intended. QA is great at helping uncover unknown unknowns, and can provide insights into how people will try to use your product.

Processes are like living and breathing things — they should not be set in stone. With each new product release or website launch you can find opportunities to improve the process and become more efficient, but you don’t need to wait until the end of a project.

Retrospectives are a great way to learn what’s working and how to improve the process while it’s happening. If done on a regular cadence with the whole team, the productivity benefits really start to kick in as people start looking for opportunities throughout the week prior to the meeting.

Even if you’re not doing Agile sprints, find a way to check in regularly with your team to learn what’s working and what’s not working.

Time is money. Literally, when you are paying someone’s salary or services by the hour. Don’t waste it, and be aware of other people’s time as well as your own. Always be looking for ways to be more efficient, and keep in mind that (fingers crossed) AI will be here soon enough to handle the dirty work and automate even more.

  • Schedule 15 or 30 min meetings — As proven by Parkinson’s law, work will expand to the time allotted, and meetings are no exception. Try shorter meetings with clear agendas, and see how much can be communicated via email ahead of time.
  • If something comes up during a standup or team meeting that needs more discussion but is only relevant to a few people, make a note for them to follow up afterwards, so as to not waste other people’s time and keep your meeting on track
  • Timebox — especially on projects with time constraints, limit the amount of time designated to task. For instance, spend no more then 20 minutes troubleshooting before escalating, or limit a research spike to 1 hour to avoid getting lost down the internet rabbit hole. Agile Sprints essentially timebox the amount of work that will get done during the sprint cycle, and the increase of productivity is a key reason Agile methodologies have gotten so popular. I’m also a fan of the Pomodoro Technique, working in 25 minute intervals of pure focus, with short break between.
  • Rules and folders in Outlook can help filter your inbox and keep you organized. For example, my teams use JIRA and Basecamp, so I set up folders for different projects and created rules that send any emails with the project key in the subject line to that folder. Our company also has in internal email list where we share interesting articles and tech trends, so I’ve set up another rule to for any emails to that alias to I can keep my inbox clear for important messages, and check the folder when I have time to read and reply.
  • Other favorite time-saving hacks: JIRA workflows and templates that can be re-used on new projects, Confluence templates for consistent documentation, and checklists for any repeated process.
Set up rules in Outlook to help organize your inbox

This is one that I’ve had to learn the hard way, from direct feedback. It’s easy for your email to get lost in a full inbox or ignored during a busy day of meetings, so don’t assume it’s been read —if it’s important, follow up in email or in a meeting, and work on writing compelling subject lines that stand out.

If something unplanned comes up, it can be scary to tell a stakeholder that we might miss their deadline— but if the risk is valid, they will want to know sooner rather then later, so they can communicate any changes to the plans accordingly. Call out red flags, even yellow flags, as soon as you know of them and have an idea of the impact and a potential solution.

And don’t forget the documentation!

What’s your favorite PM hack? Let me know!

Digital professional, creative life. Product manager for design systems at REI.

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