I've started at a gig that (for the purposes of this question) is an established but struggling company using IT as a business enabler, but not a core function. Around 200 staff with 6 IT staff (desktops, CRM, back office, etc.) and one developer; they're struggling to keep people. This sole developer - let's call him Bob - may be a familiar archetype. He's in his 20's, highly talented, enthusiastic, but also temperamental. He's learnt largely by osmosis, lacks focus, isn't methodical and can be very erratic.
So, Bob is the sort of guy who'll be assigned a month-long critical and exciting project that matches both his skills and what he says he wants to do... yet you'll often find him over by the photocopiers having hour-long "discussions" over which backlit keyboards are best for hacking Powershell with. Or, one day he'll notice his line manager is out, notice the production server is nearly full... and spend the entire day "fixing it", including unscheduled maintenance of the website once everyone else had left the office, and going to bed at 3AM.
Which is indeed what happened this week. As far as I can tell, he decided to do this spontaneously, because it "obviously needed doing". No-one signed off on the unscheduled downtime. I don't know if the issue was important; it certainly wasn't urgent; and of course his critical project is pushed back by another couple of days. I understand this happens regularly; but usually someone has walked up to his desk and asked him to pitch in to some ad hoc thing. This is the first time he's done it "by himself".
I am not Bob's line manager (who is clearly exasperated with Bob's behaviour) but I am involved with trying to add structure and generally try to turn things around. Bob's line manager has tried to add process via JIRA and Scrum, but Bob openly ignores issues assigned to him, the sprint board, etc. He seems to like working in an ad hoc manner, even given the problems this causes; and seems to see adding structure to his workday, or have managers run interference for him, as a form of micromanagement, an annoyance to be "worked around".
So, I'd like to have a retrospective / post-mortem on this - but, the small team size, compared with the rather Bob-centric nature of the issue, makes it likely to become a massive blame session at Bob (who is already very touchy on the matter - "I get the blame for everything being crap").
I want this to be constructive. I'll give the standard "this is a space to learn, everyone did the best they could given the situation they had" etc. but I don't think that would work in this situation.
On top of that, I'm not happy in this new role: I'm not able to do the things I've been hired for, there's little structure and I'm bored and frustrated. Seeing if it improves by the three month mark, but already considering leaving. I don't want my issues to infect this.
So, how can I hold an effective learning retrospective under these frankly dysfunctional conditions?
EDIT: I don't think it's a co-incidence this happened the day his line manager was out of the office. He knew he could "get away with it". Perhaps he views this as a form of heroics. On reviewing this question, I'm starting to wonder if this is some form of irrational compulsive behaviour, to be honest...