Overheard: “Tasking out the sprint in hours should have been more accurate than doing it in something as imprecise as story points”.
Every time I hear the word “should” my ears perk up. Ding, ding, ding… alarm bells, warning flags…! Using an agile mindset we need to look at what did happen, not what should have happened. For years I heard colleagues talk about how we should have planned better, that design should have worked, employees should be happy with what we gave them… And yet history teaches us something else – it teaches us that we learn by doing, by experimenting, by testing our hypothesis against what actually did happen, not by clinging desperately to what we thought should have happened.
When was then last time you said,”It should have worked. We just didn’t try hard enough”. Can it be replaced by “We did x…. and here’s what actually happened. What did we learn from that? What do we want to try next?”?
History is an available teacher. It’s up to us to do the learning.
Susan K DiFabio 
Agree with all this. “Should” is sometimes a keyword signaling shame. See -> http://clabs.org/blog/TechnicalIntimidation
Thanks chrismo. That’s an interesting notion that there is a connection between “should” and shame. The trick is to recognize it when it happens and replace shame with curiosity.
Yeah, something I’d learned from a counselor that I’ve found to hold true. Feelings of shame are attached to my identity and beliefs about my self. Sometimes that’s not a bad thing. I think humility involves feeling healthy shame about my shortcomings. But often times these statements as you detail out in your post are coming from a place of wishing the current situation wasn’t true, and then applying an incorrect belief that I have more control over things than I actually do. Believing I’m more powerful than I am can set myself up for a lot of perceived failure that ultimately is a waste of my time and energy.
This is why I think Agile is so powerful. It’s sort of like the Serenity Prayer for software development. It humbly acknowledges we don’t have all the answers, so let’s own up to it and live as if that were true, instead of a Big Up Front culture that is foolishly holding on to the belief that EVEN MOAR effort the next time can conquer everything the first time.
Oh, and I just remembered an old post of mine that is along the same lines as yours: http://clabs.org/blog/EmergentAngst
A coach friend of mine uses the phrase: stop “shoulding” yourself.
Clever. I’ll have to remember that one. Thanks.
Susan