Portland Digital PM Workshop Recap

Thanks to the 50 or so attendees who came to yesterday’s digital PM workshop at Instrument! I had a great time co-leading the event with Brett, and it seemed like the general consensus was that people found the exercise and discussion valuable.

We started off the day with introductions and then jumped straight into the project planning exercise. Attendees were handed one of two scenarios:

  • Scenario A, a fast-turnaround one week project
  • Scenario B, a more complete full redesign and rebuild project over the course of several months

From there, people took to paper and pen to individually put together a project plan for their scenario, noting assumptions, schedules, budgets, and more.


After individual project plans were prepared, small groups formed to discuss their different approaches to the scenario. From there, teams took to large sheets of paper and came up with a unified group plan to address the project.



After projects were planned, we had groups tweet photos to the hashtag #DPM2014 to share. Two teams for each scenario presented their plans to the group, followed by some brief Q&A for each presenting team.



The approaches were all unique and insightful, involving lists, gannt charts, timelines, and more. A favorite presentation for the one-week slightly crazy Scenario A involved a curve that looked a bit like a snow-capped peak and unintentionally evoked the challenges of climbing a mountain when it comes to projects of that duration. The exercise proved that while tools are helpful, paper and pen and experience is all it takes to communicate a project plan.

After a quick break, we did away with the tables in favor of a big circle for the sake of acoustics without mics in the big room at Instrument. From there, we had a group discussion around four topics: people & teams, process, tools, and managing expectations. We led in that order partly because while I’m mixed on agile methodologies, I’m a big believer in the agile manifesto, and particularly “individuals and interactions over processes and tools” when it comes to how we approach projects.



People & Teams

I led off the discussion on people and teams with a few different thoughts:

  • I touched on the idea that when you feel overwhelmed, think back to the core parts of your role, which boils down to two things: 1) identify and minimize project risks, and 2) help your team (including the client) work better. If you focus on the most important tasks in those categories every day, it’s hard to not be successful as a PM
  • I mentioned my belief that the two pizza team (a team that can be fed by two pizzes, or 4-8 people) is about ideal for most projects
  • I introduced the concept of personalities falling under Challenger (the individuals who question the status quo, or devil’s advocates), Doer (the really productive ones – often your favorites as a PM), Thinker (the architects and creative directors of the world), and Supporter (those who maintain and grow team harmony). Teams need all four of these roles to some extent to be successful, and project managers get to fulfill all four at times!
  • I discussed Tuckman’s stages of group development and how groups form, storm, norm and perform. I called out that this doesn’t necessarily reflect the project life cycle, but instead it reflects group maturity. Performing is great, but the danger of simply performing too long is boredom, so it’s important to understand group maturity and when it may be time to reform underperforming or stagnant groups

From there, Brett talked about being your team’s psychologist, which comes with a variety of responsibilities, including knowing how to deal with sensitive information and how to look after your team’s mental wellbeing. The soft skills of the PM role are vast and incredibly important to project success.


Brett got the process discussion started by talking about Happy Cog’s custom, flexible approach to projects and that they like to focus on building process that meets client needs. We do things very similarly at Metal Toad. He also touched on the importance of communicating process to clients and educating clients in process in order to remove bottlenecks through misunderstanding.

I touched on the classic agile versus waterfall debate and gave some insights we’ve had at Metal Toad over the past year as project scopes, timelines, and budgets have grown. At a smaller scale, waterfall is great for a short duration project where requirements are well-defined, and uncertainty is low. Agile is great for ill-defined projects with longer timelines and healthy budgets. It’s hard to impossible to have a successful Agile project without dedicated resources and enough sprints to be able to measure and predict velocity.

I also encouraged attendees to think in frameworks when it comes to process. Each project manager at your organization will do things differently to match their own personal work style, but it’s also important to communicate shared knowledge around process. Build a framework for your organization’s processes that identifies the shared tasks, activities, and checkpoints across all projects.


We discussed what tools we use and why!



Managing Expectations

Brett discussed the importance of closely reviewing the project scope with your clients, to the detail level of making sure all stakeholders understand what was agreed upon in a statement of work. Brett also introduced their status update format for weekly updates to clients (which we’ve also adopted to great success at Metal Toad):

  • What Happened Last Week
  • What is Happening This Week
  • Action Items
  • Timeline Updates/Adjustments
  • Budget Update
  • Risks

Above all else, Brett emphasized honesty and transparency as key in managing client expectations on projects, which I wholeheartedly agree with!

I brought up my practice of always outlining a plan B (and potentially plans C and D) when it comes to delivering bad news. You never want to leave a client hanging with bad news. Instead, provide a potential solution. There’s always an option, though you might have to get creative about it. I also emphasized the importance of non-finger-pointing retrospectives, including both internal team retrospectives and retrospectives with clients.

Finally, I brought things full circle back to the concept that project success is all about teams and people, and it’s crucial to managing expectations to make sure your client understands that they’re part of your team and the commitment they need to have to their own project.

More Event Opportunities Coming Up

If you missed this workshop but would like to attend one, you have two more options this year. Brett will be putting on similar workshops in Minneapolis (May 10th with Meghan Wilker), and New York (date TBD with Aretha Choi). That’s all leading up to the 2014 Digital PM Summit this October in Austin! I’ll be there with a few fellow team members from Metal Toad, and if it’s anything like the 2013 event, I’d encourage anyone who can make it to attend.

On the local Digital PM scene, our next meetup is April 8th at Swift, and you can RSVP now if you’ll be attending. I hope to see you there!


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