Software Management 
…for people who just want to get stuff done.
But I Never Want to Be 
a Manager!
Planning Estimation Execution Retrospective 
Project 
Milestones 
Sprints 
Stories 
Software Management Dimensions
Definitions 
Planning 
Estimation 
Execution 
Retrospective 
Project 
Milestone 
Sprint 
Story
Planning Estimation Execution Retrospective 
Waterfall 
Project 
Milestones 
Sprints 
Stories
Planning Estimation Execution Retrospective 
Agile 
Project 
Milestones 
Sprints 
Stories
Planning
All Plans are Wrong 
“No plan of operations extends with certainty 
beyond the first encounter with the enemy's 
main strength.” 
- Helmuth von Moltke the Elder 
“No software plan extends with certainty 
beyond the first component interaction, 
or the first unknown technology.” 
- Cliff McCollum
Planning Techniques 
Dependency Planning 
Critical Path Analysis 
Alternative Delivery
Estimation
All Estimates are Flawed 
The goal is to eliminate your biases in a 
systematic way. 
Can you make half of your estimates too low 
and half of them too high? 
In effect, can you average your errors to 
zero?
Estimation Techniques 
Rely on the expert 
Planning Poker 
The 50th Percentile Rule 
Monte Carlo Simulations 
Fudge Factors
Execution
All Execution is Hard 
Worst challenge is what you don’t know 
All development is learning 
Don’t lie to yourself or 
others
Execution Techniques 
Design Reviews / Code Reviews 
Pair-Coding 
Daily Standups / Reporting 
TDD / MDD / Continuous Integration 
Issue Tracking / Shared Documentation 
Knowledge Discovery
Projects
Project Planning 
Consider separate items of business 
value. 
Deliver them one at a time. Don’t 
interleave all your business value.
Project Estimation 
The further away a deadline is, the less 
precise it becomes. 
Expected Duration Date Accuracy 
One Week +/- one day 
One Month +/- one week 
One Quarter +/- one month 
Six Months +/- two months 
One Year +/- six months 
> One Year +/- Unknown 
You should not estimate > 1 year out.
Project Estimation 
Always plan to produce something 
useful in less than six months. 
Even better, do it in one quarter.
Project Execution 
• I don’t suggest thinking much 
about Dev at this level. 
• This is where you consider 
marketing, communications, etc. 
• Biggest value is watching Tech 
Milestones.
Project Retrospective 
• Too high-level to be of much value 
– unless you plan to write a book
Milestones
Milestone Planning 
Milestones Can exist at multiple levels. 
Group stories in Business-Value sets, with 
natural tech chunks below that.
Milestone Estimation 
Easiest performed as a roll-up of the Stories 
underneath each. 
Add fudge-factors at this level.
Milestone Execution 
Track each story regularly. Ideally daily. 
Burndown charts should be used here.
Milestone Retrospective 
When a date is missed, it is time to be 
brutally honest. 
Why was it missed? 
What is the impact? 
What are you going to 
change? 
Don’t tell lies.
Milestone Retrospective 
Why was it missed? 
New knowledge? 
Difficult problems? 
Changed business situation? 
Team problems?
Milestone Retrospective 
What is the impact? 
Slip the schedule? 
Cut scope? 
Add resources?
Milestone Retrospective 
What are you going to change? 
Don’t tell yourself lies. 
If your estimates were wrong here – they are 
probably wrong everywhere else. 
Working harder is a poor solution. 
Hope is not a strategy. 
You must accept one of the previous impacts. 
What do you change about future milestones?
Sprints
Sprint Planning 
Keep your backlogs aligned to your 
Milestones 
Don’t change a planned sprint
Sprint Estimation 
What is your team velocity? 
How do you know? 
Stretch a little. 
Leave space for the 
unexpected.
Sprint Execution 
Use Burndowns and Daily reviews. 
If you are above the line, find out why 
immediately. 
Address blockers before 
anything else.
Sprint Retrospective 
Lots written about this. 
Don’t skip them.
Stories
Story Planning 
No story should be larger than one person 
can complete in one sprint.
Story Estimation 
If you code it, you estimate it. 
Break stories down into tasks and estimate 
those. 
Follow the 50th percentile rule.
Story Execution 
Don’t lie to yourself: update your estimate 
every day.
Story Retrospective 
Probably not useful.
Q&A

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Software management...for people who just want to get stuff done

Editor's Notes

  • #3: If you develop software, you are either your own manager, you work for a manager, or you desperately need a manager. No sufficiently complex endeavor can be undertaken without management unless you never care when, how, or if it finishes.
  • #4: Every software development process executes on these dimensions. Different methods emphasize some areas more than others, but none of these go away regardless of your method.
  • #6: Every software development process executes on these dimensions. Different methods emphasize some areas more than others, but none of these go away regardless of your method.
  • #7: Every software development process executes on these dimensions. Different methods emphasize some areas more than others, but none of these go away regardless of your method.
  • #20: Don’t believe anyone who says they have a plan whose first deliverable is more than six months out. Just walk away. Or find smaller deliverables.