ENGINEERING
Defining the Foundation
Setting Early Milestones
Set short-term and long-term goals that align with the product vision. Milestones provide structure and benchmarks for tracking progress.
Why it's Important
Keeps the team focused and motivated.
Helps identify risks and bottlenecks early.
Builds momentum by celebrating smaller wins.
How to Implement
Break down the product vision into actionable steps using a roadmap.
Apply the SMART framework (Specific, Measurable, Achievable, Relevant, Time-bound) to set milestones.
Hold collaborative planning sessions with the team to ensure buy-in. Include all relevant stakeholders.
Estimate the work involved in completing each milestone. Keep track of your original estimates so you can later compare to how much work the milestone actually took.
Brainstorm the steps or tasks involved in building each feature.
Create a timeline or Gantt chart to visualize the sequence of deliverables.Be sure to include time for research or experimentation, especially if you are developing new technology.
Consider incorporating Agile methods such as a Daily Standup and Sprint Reviews to maintain momentum and keep the team focused.
Regularly validate the product by gathering user feedback on completed features.
Regularly review and adjust milestones based on user feedback or obstacles.
Available Workshops
SMART Goal-Setting Workshop: Collaboratively craft specific milestones, ensuring they are measurable and realistic.
Backward Planning Exercise: Start with the long-term vision and work backward to identify key milestones.
Risk Assessment Workshop: Brainstorm possible risks to achieving each milestone and create mitigation plans.
Prioritization Session: Use frameworks like MoSCoW (Must-Have, Should-Have, Could-Have, Won't-Have) to rank milestones.
Timeline Mapping Exercise: Build a shared visual timeline to sequence milestones and dependencies.
Role Clarity Workshop: Define who owns each milestone and their responsibilities.
Sprint Planning Workshop: Determine what features and milestones your team will focus on over a set period of time, usually 2-4 weeks.
Agile Estimating Workshop: Use prior data to accurately estimate how much your team can realistically build in a 2-4 week sprint.
Deliverables
Roadmap with clear milestones and timelines.
List of risks and corresponding mitigation strategies.
Assigned ownership for each milestone.
A prioritized backlog of tasks related to the milestones.
How to Measure
Track milestone completion rates.
Monitor team feedback on milestone feasibility and pacing.
Evaluate progress regularly through retrospectives and reporting.
Track estimate accuracy
Real-World Examples
Basecamp
Defined milestones for early feature development to launch incrementally.
Netflix
Shifted from DVDs to streaming through phased milestone execution.
Tesla
Published a multi-phase "Master Plan" detailing milestones for sustainable energy products.
Get It Right
Prioritize milestones that deliver user value first.
Keep milestones achievable within a reasonable timeframe.
Regularly celebrate completed milestones to maintain morale.
Continuously reassess and adjust based on feedback.
Align milestones with your available resources.
Don't Make These Mistakes
Setting unrealistic or overly aggressive timelines.
Ignoring dependencies between milestones.
Skipping regular reviews of progress and risks.
Failing to communicate milestones to all team members.
Overloading the roadmap with too many minor goals.
Provided courtesy of Tricia Ballad, Tech Leader
Disentangled Tech