[kalleth]

Author here. I've been lucky enough in my career to hold some senior positions, and I thought I'd give a step-by-step on an approach I took with an "enterprise-scale" software project, and how I stole some techniques from university project management courses to meet with some success. Happy to answer any questions :)

[mzarate06]

I'm curious that you mention project management courses from university. How much benefit have you found them to provide in practice?

Asking b/c I've taken two courses in dev process or project management in my academic career, and neither provided substantial value or benefit to how I've lead projects professionally.

[kalleth]

In the early stages of my career, or in startup life? Absolutely not. Very little relevance; XP/SCRUM were both covered together in a single 50 minute lecture, the rest of the PM aspects were tackling paperwork-generation methodologies like the "Rational Unified Process" and "Dynamic Systems Development Model", both of which I feel like would be _hell_ if I actually had to work within.

However, there were techniques (like critical path analysis) that as I've got more senior, started working at larger companies, and started stepping down the senior leadership path, I've started to see some applicability to. Not direct applications - they still need taking with a massive pinch of salt, and modifying for modern learnings in industry, but they do start to provide some value, even if it's just learning what the grey-hairs in the exec are used to seeing :)

[mtippett]

Fully agree. There are huge nuggets of wisdom in old-school engineering. For example PERT is something that most people don't know about. But it's simple to apply in the real world. Get three estimates - optimistic, pessimistic and realistic. double the realistic, add the optimistic and pessimistic and divide by four. It's basically a centerweighted estimate - but it forces you to think about the the corner-cases and what could go wrong.

Lots of other old school stuff that we "just turning grey" people need to translate for the new kids.

[justin_oaks]

How are deadline dates assigned? Is the deadline exactly the same as the estimated completion date?

Realistic estimates aren't padded, but they still have significant probability of being inaccurate. After all, they're estimates, not information from the future transmitted to the past.

[kalleth]

This is where the ideal meets the annoying reality of The Enterprise (tm).

I can't talk in too much detail, but in general, the deadline date was fixed through commercial contracts signed at a high enough level that engineering didn't have sight of them. The concept and commercial case was sound, but the implementation hadn't been worked out yet, when a date was set.

My strong preference would be for estimation to come first, of course, before a deadline is picked (and even then, only picked if it is really a necessary deadline), which is then based on reality, and also include some slack for unintended discoveries.

[hu3]

I had this "Enterprise sets the deadlines" experience just yesterday.

I delivered a spreadsheet with detailed information of how long it would take to develop each feature of the new module they wanted. It totalled around 3 months of development.

Fancy suit folks told me 3 months wouldn't do because sales promised it would be ready in 2 months. Then I was asked where could shortcuts be taken.

In the end we had to cut features that will certainly upset our client given their initial expectation.

[sarks_nz]

Thanks for the article. Curious how you ensure dev outputs match up with other (external) deadlines, for example, the sales/marketing teams firing up a promotion of your new functionality.

How do you incentivise devs to hit those timeframes?

[PUSH_AX]

Our paths crossed on the engineering team of a certain letterbox flower company, for a short time at least. Good to see you doing well Tom, nice article.

[kalleth]

Thanks! And I couldn't possibly comment on which company that could be...

Hope you're doing well too!

[ksec]

Do you think there is a different in how US and UK tech companies in project planning?

[kalleth]

I've never worked for a US tech company, so I wouldn't know, sorry!

[pphysch]

What tools and methods do you use for creating, sharing, and modifying project charts?

[kalleth]

Depends how much of a perfectionist I'm feeling. For the initial development, a sharpie, index cards, and a whiteboard wall - or Lucidchart, because it's basically an in-browser whiteboard/drawing tool.

Once the project is ongoing and you'll need to account for changes, I've either done it manually (which takes an age) or handed it off to PM's to oversee using either MS Project, airtable with a custom-authored set of actions/etc, or PrimaVera.