My Five Biggest Failures

in Software

Will Klein

About Me

ten years

six jobs

fired twice

About Me

three years in Colorado

Rally Software

CA Technologies

Crownpeak

It’s only when we move away from the idea that we need to be perfect that we will heal ourselves and others around us. I could easily pretend I have my act together. But what good would that do? No one learns anything that way.

My onus is never to look good or be considered perfect.

 

My only mandate is to be authentic and help release others from inauthenticity.

Shefali Tsabary

Interview published by the Washington Post

Experiential Learners

Pattern Recognition

Retros & Postmortums

The Homerun

Problem:

Unclear Expectations

Patterns

• no review structure
• no clear goals
• no regular checkins

Strategies

• setup a review structure
• create & track goals
• have regular 1-on-1s

The Heart

Problem:

Exhaustion

Patterns

• long hours
• bad sleep
• getting sick
• decreased productivity

Strategies

• limit work hours
• good sleep
• take time off
• quit

The Ambition

Problem:

Blind Ambition

Patterns

• lack of experience
• poorly defined scope
• sizing
• schedule slip

Strategies

• a senior mentor
• define scope
• sizing
• respect projections
• raise the white flag

The Stall

Problem:

Boredom

Patterns

• easily distracted
• decreased productivity
• not learning
• lethargy

Strategies

• stay fresh
• keep learning
• change projects/teams
• change jobs

Family

Problem:

Priorities

Patterns

• time away from family
• time away from friends
• time away from hobbies

Strategies

• establish work hours
• establish time off
• checkins with family
• checkins with friends
• listen

The Outage

Strategies

• a great culture
• a great manager
• mentors
• three month rule
• be healthy
• know when to move on

Failure

Failure

...is healthy

Let me think about the people who I care about the most, and how when they fail, or disappoint me, I still love them, I still give them chances, and I still see the best in them. Let me extend that generosity to myself.

Let me realize that my past failures of follow through are no indication of my future performance, they're just healthy little fires that are going to warm up my ass.

Ze Frank

An Invocation for Beginnings

Will Klein

@willklein on Slack

@willslab on Twitter