Trello Agile Series: Roadmaps & Retrospectives

Transcript until Q&A session:

Hi, welcome to the Trello Agile Series: Roadmaps and Retrospectives webinar. My name is Brian Cervino, I am the Product Marketing Manager at Trello and today I am joined by Trello product manager and retrospective expert Jess Barnett as well as support specialist Caity Cogdell. The goal of this webinar is to follow up on the first part of the Trello Agile Series which covered sprint boards with how your team can create product roadmaps and retrospectives in Trello.

For those that missed the first webinar in our Trello Agile Series, which goes in depth into successfully running agile sprints in Trello, check out our webinars page where you can watch the webinar on demand.

Full disclosure, I am not a Scrum Master, but I hope that through this webinar you will have plenty of takeaways to bring back to your team when it comes to adapting agile practices into your workflow for increased productivity and transparency.

After the presentation I will be glad to answer any questions you have about roadmap and retrospective boards. If you have any questions please type them into the GoToWebinar question box and I will be addressing as many as possible during the time allotted, with help from Jess and Caity. You can also email any questions to and our support team will be glad to answer any questions that you have. Also, I want to let you know that I will be recording today’s webinar and will email a copy of the recording to all attendees and registrants, and will be following up with links to boards you can copy and helpful resources.

From the Agile Manifesto a retrospective for development teams are defined as “At regular intervals, the team reflects on how to become more effective, then tunes and adjusts its behavior accordingly.”

While agile and scrum dev teams may have popularized them, retrospectives are incredibly helpful for teams of all kinds. Some families even hold regular retrospectives!

The fundamental goal of a retrospective is to figure out ways to work better. Happier people doing more of the best possible work as fast as possible.

Retrospectives are done in all sorts of different ways (and we’re a little biased), but we think retrospectives done with Trello are the best.

Here’s why:

Paraphrasing our Product Manager, Jessica Barnett, using Trello to run retrospectives creates an environment that is open and encouraging to all participants, placing introverts and extroverts on the same level. Everything is written down, and easily accessible by every team member, creating a shared history of every retrospective. Also, everyone gets to write down their own thoughts on a card and then read it aloud, making sure that no one’s ideas are paraphrased by the retrospectives facilitators and everyone is encouraged to speak. Finally, it facilitates a democratic process where the most important issues are discussed in depth by the entire team, and action items are created to address those issues.

Considering that sprints are often heads down focusing on the tasks to accomplish during the sprint, and leave it room for pause, retrospectives are essential for taking the time to reflect as a team what went well and what can be improved, with a clear mind but not too long after the sprint occurred while thoughts and feelings are still fresh.

Scrum teams typically run retrospectives at the end of each sprint, but they definitely don’t need to be limited to that. They can be held regularly with any team or cross-functional team.

This Trello retrospective board has been really effective with scrum teams, dev teams, executive teams, and more .

The board consists of four lists: Went Well, Needs To Change, Questions & Discussion, and Action Items.

Went Well: This list is for all of the positive aspects of the sprint, people to thank or recognize, and parts of the process that went well. Needs to Change: This is list for anything that people think needs to be change, improve, stop doing, or have complaints about. Questions & Discussion: This list is for anything that people want to talk about that don’t fit into the other two lists. Action Items: Cards are moved to this list as they are discussed and action items that need to be addressed and implemented around them are decided and assigned.

Retrospectives should start with everyone joining the meeting being added to the empty retrospective board. Members can be added from the sidebar, or a link to join the board can be shared with your team via Slack or email.

Since more and more teams are partially or fully remote, it’s likely that some or all of the retrospective participants will be joining the retrospective by video chat. Trello makes it really easy to incorporate remote teams into the retrospective in two ways.

First, Trello always updates in real time for everyone, meaning everyone is always in sync.

Second, Trello integrates popular video conferencing apps like Google Hangouts,, and as Power-Ups. By enabling one of these Power-Ups on your board you can create a dedicated room for everyone to join easily accessible right from the retrospective board.

When the meeting starts, the first thing that should be done is everyone adds cards to the retrospective board in either of the first 3 lists depending on the subject to be discussed, what went well, needs to change, or other questions and discussions that should take place regarding the sprint.

The great thing about running a retrospective in Trello and giving time for everyone to add their cards at the same time is that introverts will feel comfortable since they can think then write, as opposed to a retrospective where a facilitator is documenting feedback on a whiteboard because prevents extroverts from dominating the conversation. In fact, retrospective facilitators can even share an empty retrospective board for input days before a discussion starts to give team members some time to think about what they would like to cover during the discussion.

Team members should add themselves to cards they’ve added to the retrospective board so that the meeting facilitator can go through each list and let the person that created the card read their card aloud.

After a set amount of time, typically 3-5 minutes, the facilitator can ask if anyone needs anymore time. If not then the team goes through each list and cards are read aloud by the person that created the card. Anyone else on the team is encouraged to ask questions or request clarification.

When all the cards have been read aloud, it’s time for team members to vote on the cards that they think are most important. Facilitators should make sure to have the voting Power-Up enabled.

Team members can quickly vote on cards by hovering their mouse of a card and pressing “v” on the keyboard, or by opening a card and clicking the vote button. The number of votes on each card will be displayed on the front of each card.

After a few minutes of voting, everyone should be ready for discussion. This is an important step, because it makes sure that what the team deems most important to discuss is discussed during the retro.

Starting with the card with the highest number of votes in either the Needs to Change or Questions and Discussion columns, the facilitator will drag the card into the Action Items column and read it aloud.

The person who created the card will speak to it briefly and then the conversation naturally opens up to the room to discuss. Generally the most important part of this process is to drive out action items for each card, things that can be done to improve the issue. A good action item is specific enough to be checked in on in the next meeting. Something more than “we’ll try to be better at this” is probably a good idea.

When the team has agreed to an action item for the card, move on to the next card with the most votes until the allotted time for the retrospective has been reached.

At the start of the next retrospective make sure to revisit the action items of the prior retrospective to make sure that the issue has been resolved, or at least progress has been made. If progress has not been made then it’s important to have a discussion about what is blocking progress on any action item as it may be affecting the success of future sprints. This also builds trust into the process. If action items are not acted on your group will probably conclude retrospectives are a waste of time or even depressing.

Here’s a quick tip: To save time, set up a template Retrospective Board with empty lists and copy the board for each retrospective.

Product Roadmap The product roadmap is a place to keep track of all of the features, ideas, or requests from stakeholder and customers, often at a higher level than the individual tasks to build a feature. It’s also a way to transparently share with your company upcoming projects and goals that are going to be worked on.

Trello makes it easy to create a product roadmap that clearly defines and prioritizes features because each card contains a feature or idea to be developed and this provides a dedicated space for the team to discuss and plan in a visual and easily accessible way. Plus, lists show where each card is in the pipeline so stakeholders know exactly what stage a features is in for development, and marketing and sales teams can see what is being worked on and what’s up next to plan for launches, training, and collateral creation.

Once, again this board can be setup however it works best for your team. This one has lists for Ideas, Researching Requirements, Estimating, and Sprint Candidates. Another way to setup this board could be a Backlog list followed by a list for each of the next 3 quarters to plan out the product roadmap.

Cards start in the Ideas list where product managers, stakeholders, account managers can add ideas and requests to be considered in the product roadmap.

Cards should include a description of the feature, including the user story and motivation from a business perspective for creating the feature.

Any cases or tickets that come in from support, success, or sales should be attached to the card so that everyone on the team can access them to learn about customer pain points when considering an idea. Enable the Zendesk, Helpscout, Intercom, and FogBugz Power-Ups if you use those apps to bring information from cases and tickets directly to cards on the board. Also, when attaching to cards with a Power-Up, the number of attached cases is displayed on the front of the card as a badge, so you can quickly make note of the 30 Zendesk tickets attached, and perhaps consider prioritizing that feature.

It’s also recommended to enable the voting Power-Up so that team members and stakeholders can upvote the features they are most interested in. This will also help product managers prioritize the roadmap.

As cards are prioritized they are moved out of the Ideas list, to Researching, so that the project owner can evaluate what needs to get done to design, develop, and implement the feature. Any technical specs and mockups should be attached to the card at this stage via the Google Drive, Dropbox, or Box Power-Ups, or from your computer.

Team members should freely discuss the proposed specs for the feature in the comments section of the Trello card so that the history surrounding decisions made are in one location and accessible by everyone on the team.

Specific steps in designing, developing, and implementing the feature should be added as a checklist on the card.

Once the research phase is complete, cards move to the Estimating list where the difficulty of building the feature is estimated.

Setup a basic point system in Trello by adding points to cards via a handy dropdown list with the Custom Fields Power-Up. Points are estimates measure the degree of difficulty for a task and are often based on the Fibonacci Sequence, which is 1, 2, 3, 5, 8, 13, and can be a quick way to make sure your team is not overloaded with work during a sprint. The reason for a nonlinear numbering system like the Fibonacci Sequence is because estimates are difficult to make, and the bigger the task the more uncertainty revolves around it, this system recognizes the difficulty without producing a false level of confidence for the specific level of difficulty.

Finally, a card is moved to the Sprint Candidates list to await an upcoming sprint, depending on its priority and difficulty with relation to the rest of the features that will be developed in the next sprint.

When a card in the Sprint Candidates list is ready for development simply move the card from the Product Roadmap board to the Sprint Backlog list on the Sprint board for the next sprint.

More recently it’s become popular to use a Trello board to share a public roadmap with your customer and user community. This could either be the same board that your team uses internally, which would be a very transparent move, or it might be something that is more high level that shares more generally what is being developed. Either way, these public roadmap board can also be used to get input from your community.

One public roadmap Trello board that I love is the Front App product roadmap. On this board they’ve enabled the Voting Power-Up so that users can vote on the features they would like to see prioritized for development, and provide a way for users to easily contact the Front App team with suggestions.

To facilitate dialogue between your user community members and get more insight into exactly what people are looking for then allow public commenting on the board. This is a simple way to engage your community and learn more about how they are using your product and what pain points they are facing.

Also, share the progress of feature development by moving cards along the board to show their status, and consider creating a list for each month where all the released features can be organized. We even like to celebrate each big new feature we’ve shipped with a custom Taco sticker!

So that wraps up my presentation on how teams can use Trello for Retrospectives and Roadmaps. I am going to get the Q&A session going with Jessica Barnett joining in just a moment, focussing on questions about the boards and features demonstrated, and will try and address additional Trello questions if there is time. Please enter any questions you have in the GoToWebinar box and I will make sure to address as many as possible in the time remaining. If you have to leave the webinar now and have questions or if you would rather ask your questions in private, or have any feedback on how I can improve this webinar, feel free to email us at And once again, you should receive a copy of the recording of this webinar in the next few days, and please feel free to share it with the rest of your team. Thanks again everyone for taking the time to join me today!