Most of what I write is on TheServerSide.
Estimating software is part science and part making peace with uncertainty. Teams who treat estimation as theater end up with plays that never close. The goal is predictable delivery and fewer unpleasant surprises, not pretending you can read the future. This guide covers practical agile estimation and planning that works for scrum and kanban teams and keeps user stories moving toward production.
Keep it simple. Fibonacci numbers or t shirt sizes are both fine. The useful part is consistency. If you invent a quirky internal scale you will spend more time arguing about what medium means than building features. Pick one scale and stick to it until you have delivery data to improve it.
Tip for humans with short memories: keep three reference stories for each size class and review them quarterly. Reference stories make story points meaningful and keep new teammates from guessing wildly.
Planning poker forces private thinking followed by a reveal. Each team member gives a number privately then shows everyone at once. That prevents the usual parade of guesses where the loudest voice becomes the plan. The reveal sparks useful discussion about assumptions and risk instead of turning the room into a Q and A with one dominant opinion.
Relative sizing compares a new user story to stories you already built. Saying a story is a five because you once built a five gives your estimate context. Keep a small set of well understood reference stories and use them as the yardstick. Relative sizing scales far better than asking for absolute hours on the spot.
If you run scrum set sprint commitments using average velocity. If you run kanban focus on work in progress limits and throughput. Prioritization should include value, risk, and dependencies not just gut feeling. High value low risk items are great for predictable releases. Save risky unknowns for when you can afford learning.
Track delivered story points over several cycles and use the trend to adjust planning. Velocity is a planning guide not a scoreboard. If you start treating story points as a performance metric people will game the system and your forecasts will lie to you.
Recap in plain language. Use a simple scale, keep estimates short and social, ground numbers in past work, and let real delivery data refine your planning. Estimation will not eliminate surprises but it will reduce their frequency and the size of the mess you have to clean up. Now go estimate responsibly and try not to make a performance out of it.
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This is a dedicated watch page for a single video.