Considering Pivotal Tracker? Longtime user? Try these tips:

Jon Dobrowolski
4 min readMay 27, 2015

I love Pivotal Tracker, but I wasn’t always a fan. Before someone really walked me through success with (Pivotal) Tracker I struggled to appreciate the product. If you’re looking to optimize morale on the team, your mgmt software is probably some low hanging fruit. We’ll get in the weeds on a few things I’ve observed from a great team adopting Pivotal Tracker full sale and really reaping the benefits.

First, its important to keep in mind what Tracker is actually supposed to be doing:

  • Conversations — Tracker is not JIRA. I find that JIRA inspires CYA and blame. Your job becomes more about passing tickets around and less about making software. Tracker’s model inspires (requires) conversations instead substituting for your team’s communication.
  • You tell a story in conversation — Remember that what you’re writing isn’t a ticket, tickets are for bug tracking. The value comes when you’re writing modern user stories.
  • Predictability — Do points properly, choose the right scale, and watch as you get the deeper pulse on your product and your team velocity.
  • Better with age — Your User Stories, once completed, should serve as living documentation. I go back to user stories all the time to reference them in new stories, get people the context they’re looking for, or remind myself how we did something. Proper tagging is key for this (more below). If you want to go a step further, we delete comments that are irrelevant to our future selves. Comment discussions on an old story are important for context. Make sure you can get your bearings fast by deleting comments after acceptance that are no longer relevant to the final product, keep those that are.

Pivotal Tracker is prescriptive, but sadly it’s not communicated properly in the product.

Pivotal Tracker is a light-weight and prescriptive product. However, Tracker’s team has taken measures to make it more palatable to teams that don’t want the prescription. This was probably in service of scaling the product and business. With that in mind, here are some tips to get the most of out Tracker — in some cases these tips came from Pivotal Labs themselves (thank you!):

  • Tagging — Your stories are your business documentation, it should match up to the quality of your test suite (aka technical documentation, which is really good right?). Your well tagged stories make it easy to locate decisions made by your team and reference them in other stories for the benefit of hollistic communication. You may not be around forever, be a friend to another Product person and document your stories properly.
  • “Blocked Tags” — Probably the best tip I’ve received is to use ‘blocked’ tags. These are tags like “needs design”, “needs detail”, “needs QA”. This allows the owners of that discipline to quickly sort work that is blocked until it gets their attention. These are not assignments, they’re left to each team member to prioritize to keep the team velocity on point. These tags can be used on stories in the ice box, or actively blocking current work. I use them often to remind myself that I haven’t fully detailed a story. Update: use the chrome extension “Red Labels” to enhance this.
Use ascii blocks or patterns to add scanability to your blocked tags — Copy and Paste for Critical Blockers: █, Secondary Blockers: ▒
  • Release Markers — one of the missing features in Pivotal Tracker is the ability to separate stories in your backlog visually. Use a release marker with no date to delineate groups of work that can be prioritized within themselves.
  • Parsability — Your goal with Tracker is to be using it for as little time as possible. Writing your stories with the same general template each time saves time and forces consistent communication. Using something like StoryScrip with Tracker to make it quick and easy to stay consistent. This takes the tedium out of writing to a story template.
  • ‘Roll’ on points — If you haven’t tried this you’re truly missing out. Estimating in Tracker is one of the most important things for your success. Estimate properly and you’ll be pretty amazed at velocity and its powers of prediction (don’t forget to encourage the use of Team Strength as well to keep velocity accurate).
  • Not working? — When in doubt, communicate with your team. Do regular retros and try to constantly ask if the system is working. The only way you discover new/better/novel approaches to software is by talking with the team and iterating on your solution.

If you’re considering Pivotal Tracker: When you choose a management style, think hard about the tool you use. I find so many large decisions like the tool your team will use every day made in snap judgement or on groundless brand affinity. Doing Agile or XP? Look at tools that were built from the ground up to do this kind of work and will get out of your way.

These observations were gathered over the last couple years of Product management, specifically a lot of learning I did as Director of Product (mobile) at Refinery29. These small details keep me thinking. Happy people make great software quickly. Please press ‘recommend’ to share with other folks.

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Jon Dobrowolski

Multifinality / Concept / Product / Process / Design / Development