2025 Product Team Goals

Improve team-wide understanding of business priorities and goals

Outcomes:

Developers can clearly articulate the top 3 customer needs and business goals driving the product roadmap
Developers proactively suggest product improvements that align with business objectives
Developer questions in sprint planning reflect deeper understanding of customer use cases and business model
Developers demonstrate increased customer empathy and business acumen in design and scoping discussions
Code, architecture and technical decisions show clear alignment with product and business priorities

Implement an incremental feature delivery process to enable faster time-to-value and iterative development

Outcomes:

Features are broken down into small, independently valuable increments that can be delivered within 1-2 week sprints
Each feature has clear acceptance criteria and demo milestones defined upfront
Regular demos showcase incremental progress to stakeholders every 1-2 weeks
Feedback from demos/testing is incorporated into subsequent iterations
Development work stays focused on MVP requirements before expanding scope
New features follow a consistent process: planning > incremental delivery > stakeholder review

Establish a predictable and low-stress release process

Outcomes:

Releases happen on a regular cadence with clear entry/exit criteria
Release planning and testing activities are time-boxed and scheduled in advance
Release scope is locked 24-48 hours before release with no last-minute additions
Testing notes and documentation are complete before code enters release candidate
Release-blocking issues are identified and addressed early through improved testing
Post-release verification confirms successful deployment with minimal disruption
Team maintains work-life balance during release cycles without requiring overtime

Code cleanliness & velocity

Outcomes:

Code reviews consistently catch and address technical debt, maintainability issues, and architectural concerns
Pull requests are sized appropriately for meaningful but quick review (generally <400 lines)
Team maintains agreed-upon code quality metrics and test coverage targets
Code documentation and internal APIs are kept up-to-date as changes are made
Developers regularly refactor to improve code organization and reduce complexity
Build and test pipelines run efficiently with minimal false positives
Technical debt is actively managed with dedicated time for improvements each sprint
Development velocity remains consistent without sacrificing code quality
New features and changes can be implemented quickly due to clean, well-structured codebase

Retro of Retros

Summary

Based on the retros, application developers most struggle with understanding:

Building Industry Terminology

Confusion between “programs” vs “projects”
Misunderstanding of contractor vs consultant roles
Limited knowledge of building phases

Customer Workflows

Did not understand how CPC used different roles
Unclear on permissioning needs
Struggled with bid and procurement processes

Example from Chuck: “I definitely did not understand fully what the product was supposed to do […] I didn’t even know that consultants are different from contractors.”

The gaps caused significant rework - Chuck mentions throwing away three weeks of work due to misunderstanding building industry concepts and workflows.

Root causes appear to be:

Limited direct interaction with end users
Lack of domain knowledge documentation
Complexity of building industry processes
Most developers new to construction software

This particularly impacted Generic Projects where developers had to understand complex building industry workflows to implement appropriate solutions.

Based on the retrospective meetings, these key problems have persistently recurred:

1. Project Management & Planning Challenges:
- Lack of dedicated project management causing developers to split focus between coding and PM work
- Difficulties with scope creep and changing requirements, especially in Generic Projects
- Challenges with prioritization and tracking progress across multiple projects
- Communication gaps between engineering team and stakeholders about project status

2. Process & Documentation Issues:
- Inconsistent ticket management and board organization in Zenhub
- Incomplete or unclear documentation for features and requirements
- Challenges with sprint planning and release processes
- Need for better demo/feedback cycles during development

3. Technical Debt & Infrastructure:
- Ongoing issues with staging environment (Fly) stability and costs
- Flaky tests requiring multiple runs
- Database connection and environment setup difficulties
- Security-related technical debt

4. Team Communication & Coordination:
- Challenges coordinating across distributed team members
- Multiple overlapping standups causing meeting fatigue
- Difficulty tracking work across different sub-teams (calc service vs momentum)
- Questions about when to have synchronous vs asynchronous discussions

5. Development Environment:
- Inconsistent local development environments
- Difficulties with onboarding new team members/contractors
- Problems with database access and configuration
- Challenges with testing and QA processes

These issues frequently led to discussions about potential solutions, including hiring a dedicated PM, improving documentation practices, and establishing better processes for addressing technical debt.

Top 10 Recurring Issues Analysis

1. Project Management Bandwidth

Problem: Team lacks dedicated project management, causing developers to split focus between coding and PM tasks.

Examples:

Sep 18, 2024: “Jason’s doing a good job heading all of the projects, but at the same time, he’s doing a lot more things too”
Aug 7, 2024: “I’ve been pushing pretty hard about letting’s make our Thursdays […] And it’s going to cause a few problems”
May 21, 2024: “It’s just a matter of being able to explain this well enough so that people aren’t […] their anxiety level stays low”

Attempted Solutions:

Rotating project management responsibilities among team members
Creating more detailed documentation and specifications upfront
Implementing weekly feature scoping meetings
Adding project-specific standups
Breaking down work into smaller, manageable chunks (“rooms”)

2. Technical Debt Accumulation

Problem: Team struggles to prioritize and address technical debt while maintaining feature development velocity.

Examples:

Sep 18, 2024: “We still stumble on a ton of dishes to do and aren’t well organized for it”
Jul 24, 2024: “We got to make sure that any Nixon, little things that you guys are doing are part of those rooms”
May 15, 2024: “Sometimes we find a mountain of work, whether it’s the fly staging, again, the flaky test stuff on security”

Attempted Solutions:

Creating dedicated backlog grooming meetings
Setting aside 20% of sprint time for tech debt
Creating threads in Slack for prioritizing issues
Adding tech debt review to sprint planning
Implementing voting system for prioritizing fixes

3. Environment Stability

Problem: Issues with staging environment reliability, database connections, and local development setup.

Examples:

Oct 2, 2024: “Staging fly needs to stay awake longer”
Aug 7, 2024: “I spent a lot of time with Lydia […] it is rather painful to get our local environment set up”
May 29, 2024: “We have a lot of stuff that’s just ask Chuck for this database file”

Attempted Solutions:

Hiring contractor (Lydia) to improve setup process
Creating better documentation for environment setup
Implementing automated setup scripts
Setting up codespaces as alternative
Working on improving database seeding

4. Meeting Overhead

Problem: Multiple overlapping standups and meetings causing fatigue and reduced productivity.

Examples:

Jul 10, 2024: “Are we getting feedback from users? Maybe not users, but, like, are we communicating priorities”
May 21, 2024: “I think we just had to come to this meeting to walk through a figma thing”
Apr 17, 2024: “Release planning and sprint planning […] I found that in that meeting we’re talking about what’s going into the current release”

Attempted Solutions:

Separating release and sprint planning meetings
Making certain meetings optional
Creating project-specific standups
Moving some discussions to async channels
Implementing “office hours” format

5. Process Consistency

Problem: Inconsistent adherence to processes around tickets, code review, and release management.

Examples:

Oct 28, 2024: “Sometimes we’re still not tagging tickets, not putting in the columns”
Aug 21, 2024: “The tickets we’re filing should have a body in detail what it is for, not just titles”
May 15, 2024: “There were items in the release board that actually pegged to have been part of six one”

Attempted Solutions:

Creating templates for tickets and PRs
Implementing conventional commits
Adding process documentation
Creating Zenhub board structure
Setting up release threads in Slack

6. Requirements Clarity

Problem: Unclear or changing requirements leading to rework and confusion.

Examples:

Aug 7, 2024: “Three weeks into the project, I threw away everything I wrote”
May 21, 2024: “We don’t know if we’re going to do one program in the next year or 50 programs”
Apr 17, 2024: “UAB we request the finish line, we pulled out the champagne […] And then we realized this is not what we wanted”

Attempted Solutions:

Implementing PRD (Product Requirements Document) process
Adding more stakeholder demos
Creating detailed design docs
Breaking work into v0/v1/v2 phases
Increasing communication with product team

7. Testing Infrastructure

Problem: Flaky tests and inadequate testing processes causing delays and uncertainty.

Examples:

Sep 18, 2024: “Flaky tests slowed me down because I had to rerun my pull request thing three times”
Jul 24, 2024: “Items fail in staging QA but walk locally”
May 15, 2024: “There are like 50 plus tickets on the queue and almost like 30, 40% of those are security tickets”

Attempted Solutions:

Creating dedicated QA notes section in tickets
Adding testing requirements to PRs
Implementing better test logging
Creating testing documentation
Adding automated test runs

8. Team Communication

Problem: Communication gaps between team members and with stakeholders about project status and priorities.

Examples:

Sep 18, 2024: “Bomi calling us individually […] because she doesn’t know who is managing or who’s looking at what”
Aug 7, 2024: “We have to get ahead of that. And then as soon as that is, is done and we get buyout”
May 21, 2024: “We kind of forget because we are working on it all the time”

Attempted Solutions:

Creating project-specific Slack channels
Implementing weekly demos
Adding more documentation
Creating progress update threads
Setting up regular stakeholder meetings

9. Feature Prioritization

Problem: Difficulty balancing multiple priorities and determining what to work on next.

Examples:

Oct 28, 2024: “In a backlog with crystal clear priorities”
Aug 21, 2024: “Long island expansion. They’ll know about that come up”
May 21, 2024: “We have a lot of big, big rocks or whatever we’re calling them”

Attempted Solutions:

Creating prioritization framework
Implementing sprint planning process
Adding backlog grooming sessions
Creating milestone planning
Setting up regular priority review meetings

10. Security Work

Problem: Balancing security requirements with feature development and technical debt.

Examples:

Oct 28, 2024: “Security […] we need to make a call about how we go about this”
Aug 21, 2024: “The problem with the staging with user switcher was a security issue”
May 15, 2024: “Going to security or computer security […] we need to figure out what we do about it”

Attempted Solutions:

Adding security review process
Creating security documentation
Implementing security testing
Adding security requirements to PRs
Creating security-focused sprints