Like most programmers Iâ€™ve generally tried to steer well clear of getting involved in management duties. The trouble is that as you get older I think this becomes harder and harder to avoid. Once you get the mechanics of programming under control you might find you have more time to ponder about some of those other duties which go into delivering software because they begin to frustrate you.
The Price of Success
Around the turn of the millennium I was working in a small team for a small financial organisation. The management structure was flat and we had the blessing of the owner to deliver what we thought the users needed and when. With a small but experienced team of programmers we could adapt to the every growing list of feature requests from our users. Much of what we were doing at the time was trying to work out how certain financial markets were being priced so there was plenty of experimentation which lead to the writing and rewriting of the pricing engine as we learned more.
The trouble with the team being successful and managing to reproduce prices from other more expensive 3rd party pricing software was that we were then able to replace it. But of course it also has some other less important features that users then decided they needed too. Being in-house and responsive to their changes just means the backlog grows and grows and growsâ€¦
The Honeymoon Must End
While those users at the front of the queue are happy their needs are being met youâ€™ll end up pushing others further down the queue and then they start asking when youâ€™re going to get around to them. If youâ€™re lucky the highs from the wins can outweigh the lows from those you have to disappoint.
The trouble for me was that I didnâ€™t like having to keep disappointing people by telling them they werenâ€™t even on the horizon, let alone next on the list. The team was doing well at delivering features and reacting to change but we effectively had no idea where we stood in terms of delivering all those other features that werenâ€™t being worked on.
MS Project Crash Course
The company had one of those MSDN Universal licenses which included a ton of other Microsoft software that we never used, including Microsoft Project. I had a vague idea of how to use it after seeing some plans produced by previous project managers and set about ploughing through our â€œbacklogâ€  estimating every request with a wild guess. I then added the five of us programmers in the team as the â€œresourcesâ€  and got the tool to help distribute the work amongst ourselves as best as possible.
I donâ€™t remember how long this took but I suspect it was spread over a few days while I did other stuff, but at the end I had a lovely Gantt Chart that told us everything we needed to know â€“ we had far too much and not enough people to do it in any meaningful timeframe. If I remember correctly we had something like a yearâ€™s worth of work even if nothing else was added to the â€œTODO listâ€ from now on, which of course is ridiculous â€“ software is never done until itâ€™s decommissioned.
For a brief moment I almost felt compelled to publish the plan and even try and keep it up-to-date, after all Iâ€™d spend all that effort creating it, why wouldnâ€™t I? Fortunately I fairly quickly realised that the true value in the plan was knowing that we had too much work and therefore something had to change. Maybe we needed more people, whether that was actual programmers or some form of manager to streamline the workload. Or maybe we just needed to accept the reality that some stuff was never going to get done and we should ditch it. Product backlogs are like the garage or attic where â€œstuffâ€ just ends up, forgotten about but taking up space in the faint hope that one day itâ€™ll be useful.
The truth was uncomfortable and I remember it lead to some very awkward conversations between the development team and the users for a while . There is only so long that you can keep telling people â€œitâ€™s on the listâ€ and â€œweâ€™ll get to it eventuallyâ€ before their patience wears out. It was unfair to string people along when we pretty much knew in our hearts weâ€™d likely never have the time to accommodate them, but being the eternal optimists we hoped for the best all the same.
During that period of turmoil having the plan was a useful aid because it allowed is to have those awkward conversations about what happens if we take on new work. Long before we knew anything about â€œagilityâ€ we were doing our best to respond to change but didnâ€™t really know how to handle the conflict caused by competing choices. There was definitely an element of â€œhe who shouts loudestâ€ that had a bearing on what made its way to the top of the pile rather than a quantitative approach to prioritisation.
Even today, some 20 years on, itâ€™s hard to convince teams to throw away old backlog items on the premise that if they are important enough theyâ€™ll bubble up again. Every time I see an issue on GitHub that has been automatically closed because of inactivity it makes me a little bit sad, but I know itâ€™s for the best; you simply cannot have a never-ending list of bugs and features â€“ at some point you just have to let go of the past.
On the flipside, while I began to appreciate the futility of tracking so much work, I also think going through the backlog and producing a plan made me more tolerant of estimates. Being that person in the awkward situation of trying to manage someoneâ€™s expectations has helped me get a glimpse of what questions some people are trying to answer by creating their own plans and how our schedule might knock onto them. Iâ€™m in no way saying that Iâ€™d gladly sit through sessions of planning poker simply for someone to update some arbitrary project plan because itâ€™s expected of the team, but I feel more confident asking the question about what decisions are likely to be affected by the information Iâ€™m being asked to provide.
Naturally Iâ€™d have preferred someone else to be the one to start thinking about the feature list and work out how we were going to organise ourselves to deal with the deluge of work, but thatâ€™s the beauty of a self-organising team. In a solid team people will pick up stuff that needs doing, even if it isnâ€™t the most glamourous task because ultimately what they want is to see is the team succeed , because then they get to be part of that shared success.
 B.O.R.I.S (aka Back Office Request Information System) was a simple bug tracking database written with Microsoft Access. Iâ€™m not proud of it but it worked for our small team in the early days :o).
 Yes, the air quotes are for irony :o).
 A downside of being close to the customer is that you feel their pain. (This is of course a good thing from a process point of view because you can factor this into your planning.)
 See â€œAfterwood â€“ The Centre Halfâ€ for more thoughts on the kind of role I seem to end up carving out for myself in a team.