If you are the kind of human who listens to podcasts, you will probably have heard of Gimlet Media and This American Life. Especially This American Life, which was a radio show in the US for years before the internet and podcasting brought it to ears the rest of the western hemisphere. For me, it was the show that made me a person who listens to podcasts, rather than a person who happened to put the Kermode and Mayo Film Review show on their iPod every week, and it’s probably the reason that so much of my podcast content comes from the other side of the Atlantic Ocean. Including Gimlet content. For those who haven’t found themselves tracking This American Life‘s various “offspring” (i.e, its previous producers’ new pod-babies), Gimlet’s founder, Alex Blumberg, started on TAL, and I think that it was either a TAL or an Ira Glass tweet that put me on to StartUp, the podcast about starting up a start up, to which I listened avidly. In the past few years I have learned that it takes one season of StartUp to paint my hallway and stairs, and about six episodes of Reply All, Gimlet’s second show, to drive from Skye to Fort William in late December.

All this strange pod-family history is relevant because I just listened to my first episode of Without Fail, Alex Blumberg’s latest show, in which he interviews his former boss and mentor, Ira Glass. The premise of Without Fail is that Alex interviews people about their successes and failures, and what they’ve learned from both. However, in this episode, the focus is more on how TAL came to be and what Ira puts into it and also on what Alex learned from Ira during his formative years in audio journalism and storytelling: and for me, it’s this last that’s really fascinating.

One of the reasons I really engaged with StartUp was because it arrived at around the time I was working out some ‘what nexts’ in my own career - a career that has featured a mentor / career maker, in the vein that Ira is for Alex - and as I was taking some of my first baby steps into line management and engaging in organisational systems and politics on my own behalf. In one little mini-season, they look at Gimlet as the company is growing (Diversity Report, Disorg Chart, Diversification of Worry, You Can’t Wear a Suit Here, and Shadowed Qualities) and Alex is fairly open his own struggles and weakeness as his company grows. It’s something that makes him human and engaging, and it’s a reason why I go back to his shows.

So, while all of this episode of Without Fail was pretty fun to listen to, the bit that really grabbed me was when the conversation turned to the things Alex learned from Ira. It starts about 31 minutes in, with Ira talking about the hours he’s working at the moment. Alex brings up the subject of the mix notes that Ira produces for TAL and pursues a conversation about what these say about Ira’s habits, working and management. This leads to some reflection on what the fact that Ira Glass is still doing the mix notes on This American Life has to teach Alex about how he works and leads his company.

Here’s one thing that’s particularly interesting to me. (1) Ira is clearly aware that he’s not perfect or a great management role model (Alex says, ‘you’re a complicated boss’, and Ira owns it) - but he doesn’t show the same kind of interest that Alex seems to show in the Shadowed Qualities epsiode of StartUp in developing and changing. Perhaps the fact that he’s running one show, rather than a company producing a stable of shows is at play here, but I suspect he’s also a different kind of person than Alex - and I would put money on me preferred to work for Alex than Ira.

For example, on the subject of the mix notes, Ira says, ‘I shouldn’t be doing this every week’ - but he still does it. And when pushed on why he is still doing it, he says two things: (1) ’Oh, its bad management… it didn’t occur to me I could get out of that too,’ and also (2) ‘I just didn’t get sick of it yet, I like doing it, it makes the mixes better, it’s satisfying.’ To me, this says two things: firstly Ira is pretty bad at delegation and probably operates at a fairly high level of micromanagement, and secondly, he’s not really dealing with the fact that leading something generally means that you don’t get to do some of the things that you loved doing when you didn’t lead a team of people doing a thing. I empathise with both, but particularly the second.

On the first I don’t think I lean much towards micromanagement: but I’m also generally not managing people with whom micromanagement would be in any way productive and effective - not just because of personality, but because of the work itself. And yet I do have to work hard at not taking a, ‘Well, I would do it like this and this would be right,’ approach to some of my line management - particularly of the things I once did and have stopped doing - and also when I’m editing other people’s writing. On the second, well, that’s something I deal with every week. There are things that I used to do regularly in my old job that I don’t get to do as much of any more, things that I miss, but that I had to hand on and continue to have to hand on to an ever greater extent. They are things that were satisfying, to echo Ira: they might have been complicated at times, but they were tangible, fruitful and, omigosh, they reached completion. Basically, they were things that let me feel like I was in control of them, and therefore life, rather than, y’know, not.

From the convesration you get the sense that Ira is aware that’s he’s hanging on to something that he probably shouldn’t be, work-wise, because he gets joy and satisfaction - but he’s also, I suspect, letting it hang on to him, because of his care about the quality of his show. It’s something Alex seems to be more alert to and deliberately engaged in as he works out how to be a good manager and leader and also serve Gimlet with his skills: something, I think, that shows in the way he is asking himself what he is good at and brings to his company, not just what he enjoys. It’s one of the things that make me think I’d rather work for Alex than Ira: both seem able to take feedback and criticism - but one seems more likely to think about changing.

Less this all seems negative, the interview turns from this point to a discussion how Ira feels about watching the baby producers he has nurtured and trained leave TAL to start their own shows and companies - depriving him of the pay-off of his investment in them and making competition for his own show. Ira is simply baffled by the idea that his approach to this - happily sending off his grown-up producer-chicks out into the wider audio-world - might be unusual. It’s a delightful moment that beautifully illustrates Alex’s point that Ira is a complicated boss but also someone who you want to work for and with, because working for someone who quite naturally puts energy into teaching and nuturing you and then happily lets you grow is a joy. And if I ever imitate anything about Ira Glass, I’d have it be that.