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Gollum/Smeagol lessons for aspiring CIOs

What’s the most creative way your team have given you feedback?

One of my teams once took the time to stab a toy Gollum/Smeagol in its plastic heart with a red pen, and spread the ink over tissue paper so it looked like it was bleeding to death. Apparently some decisions I’d taken earlier that day were unpopular!

Some of my best friends came from that team, good times :)

How did we end-up there?

From 2003-2005, for reasons known only to a higher power, I was given command of a grown-up multi-million dollar project. The team would grow to 33 staff at peak, including permanent staff, contractors, and assigned vendor staff. I had never managed anyone, knew nuffink. It was and remains the most intense period of my professional career, and the most formative.

Fortunately I wasn’t completely stupid and knew I had to recruit managers into this team who actually knew what they were doing. Nearly half the team came from one vendor, and I won the battle to have the vendor I felt I needed, based on the PM allocated to be in charge there. His name was Vince Di Chiara, who taught me loads and has since gone on to much higher things than teaching me.

I also brought in a good friend who was significantly more competent than me in organisation, Richard Davis. We kinda tbh made up his job as we went along, which you could get away more easily in them days. But he was vital. After the project the vendor hired Richard, so impressed were they.

I survived the project despite my absolute lack of experience by simply working like a maniac. Not a management method I recommend, and can’t have been great for the team (though comfortingly I received positive words from several, years afterwards).

The team were made up of the usual IT crowd: intelligent, good-humoured, whilst an HR manager’s nightmare. For my birthday they clubbed together and bought me talking Gollum/Smeagol toy. At the time I was rocking a shaved head and obvious body-piercings (something of a look in a traditional bank’s Steering Committees), I admit the appearance matched.

The toy had a Gollum head (bad), and a Smeagol head (good), and they could be changed. The team would thus jovially walk up to my desk and swap heads depending on whether they thought the direction I was leading in was a good idea.

It came out of nowhere, but became a “thing” and was a great interaction tool. Enabled immediate feedback and took away any hint of potential confrontation if the feedback were negative.

And the ultimate "Boss, I think we’re going the wrong way” from the team? Genius.

Here’s where I talk about this and other “how not to be a good boss” tips that I’ve learnt.

Hi, I'm Alistair, the grumpy CIO. What am I grumpy about this week crap boss says who's had one who is one - hope not! But we should be bossing this bossing stuff. Now slight operational risk risk moment for everybody who's invested in a customer of shipshape, our team actually die laughing that I'm presenting this to everybody. But nonetheless, I'm going to press ahead. Right, how not to be a good boss, I've experienced a lot of these things, formed an opinion. Here's some stuff I'm putting out to start with some hygiene factors: time sheeting, measuring, to the last 15 minutes, five minutes, everything that people do, doesn't work doesn't produce any increased productivity for you. It just pisses everybody off, and people just create an art of lying into it. Similarly, clock watching why, like, if you have good staff, and they're into it, you don't have to worry really about when they start to finish they want to contribute, because otherwise, why would they be there, they're gonna get into it. Most of the teams I've been involved in the problem is actually clock watching to get people to go away and stop working because they just into solving problems. Generally being asked now I'm not going to deal with it. But you know, abusive behaviour, definitely dump it. Very important: management by KPIs. This is something that's come up so much in the entirety of my career. You gotta have smart goals, smart, measurable, specific, measurable, whatever, just know, like, yes, KPIs are very important, but they help you manage, they are not the purpose or objective of manage managing the, the idea that got put out so much a lot of management textbooks in my careers. And if you can't manage it, you can't measure it and you want the other way around or whatever, can see how much I seriously I take it no, you measure things in order to help you manage, not the other way round, there are certain things that are just non negotiables, the p&l of the company, the balance sheet, everything else is there to help you. Alright, gratitude to who's helped and who's contributed and who suffered for working with or for me, the entire Project Tango team, you know who you are from 2003 to five, this image on the screen up here is a Gollum or a Smeagol. Great bit of management feedback. This was my first attempt at bossing a team. They had a bought toy for me for my birthday with a goal amid nasty or sneakerhead. Nice. And I would walk back to my desk and generally get feedback from the team of how well I was doing as a boss by actually having the goal and more Smeagol heads just left there. One time, I clearly wasn't having a great day because somebody had taken the time to get some tissue paper, a red pen, and actually drill a hole and fought form Smeagol or Gollum being stabbed to death in the heart and all the reading coming off of the tissue paper. Clearly hadn't been my finest hour. Well... let's go forward Jenny Waugh. Now. This is a lady who worked for me late noughties. And by this stage, I thought I was a pretty amazing boss. I'm the man. Everyone's working for me. And she just turned around to me, she had a very strong Irish accent that I'm not going to copy and just basically told me I was a bit useless at this. What she did give me some specific feedback as to why which was able to cooperate and we'll get back into lessons I've learned later. Marguerite Hudson taught me so much by basically being a really good boss. Fantastic, everyone at Caplin. I'd been a big corporate apparatchik person all the way through the naughties. And then came into Caplin to work in smaller companies in high growth companies and had to relearn how to do this again and got taught by them so much fantastic. Finally, Richard Davis, you know who you are, taught me so much. So how to be a good boss, what for me, it goes in various stages to what your requirements are being a good boss was someone working in a tech department actually changes by the time that they're actually there. So there's a very different modes before someone starts even and on their first day to when they've been there for a while. And I go through, I think I've been learned to mentor to the mistakes I've made one by one. So first of all, before they start, have a bullet point, job description, and remove the crap. Just if you can get a job description down to this and just talk through it with people fantastic, have what you want them to do for the first three weeks and first 90 days, handwritten is actually great. Or just a simple Google Sheet or whatever that you've pulled together. It's much better than having a formal job description it shows that you've thought about it very reassuring the person on the first day that you've actually considered that they want to do rather than just printed on something of Chat GPT to say, here's your job description. Day one, show that you care about their working environment, how you'll pay them, I have worked in a place where they couldn't work out how to pay me 12 weeks after I started and apparently was my fault, but it wasn't really very happy with that. What?! Have a machine for them, make sure they have all the logins, the environment, everybody cocks this up including us at Shipshape and everybody a little bit. But try and your staff will definitely appreciate it for you. Give to have very specific targets. So again, before you get there, write down I want you to do this over the next couple of days show that you've thought about it show that you thought how these tasks tasks mattered to the job to the company, how they're contributing straightaway immediately, but also how they start them integrating the rest of the team so they can start discover the job for themselves. Here, idea is to let them go. And very much my passionate belief is that you know, people drive the ship themselves. And once you've worked out the different compartments of the ship, then let the people go and run them. And there's a book out there called Turn the Ship Around that both myself and my business partner who introduced it to me very firmly believe in. But for the first few weeks, while the team is still working out how to work together do get involved in moulding it basically they do all that your work your your job is to be the boss to do your bloody job and actually help help the team go together because somebody needs to make that decision. And it's unfair, just to let people just have completely free will, everybody just gets annoyed at each other. But then once they're in space that worked out the job: norming. Freedom, again, as rifted on in previous videos, people in IT departments all over like solving problems. So let them just give them the freedom to do to there'll be overall company goals, project goals that every knows they've got to achieve, just let them do it. that you get rid of them, it literally means that they're bored. So how you've got a talented person, what are you going to do about that change up the job, change the job, it is worthwhile having this discussion, but this is a phase that goes through from like when you start through to the end, and hopefully I try and practice what I preach. It is slaughtered by all our team after I've put this out. And the number of ways I haven't done this properly, and so many other different ways that I'm absolutely shit as being a boss. But these are all things that I've cocked up before over a 20 year period sharing with you there is a phase that you go through and don't do by bloody numbers and specific measurements or like reading so many management textbooks. It is it just is nonsense. Humans don't work that way and people build software for builds products that builds profits. Thanks for watching. I am Alistair the CIO of come to us to optimise your venture, your venture capital outreach, you find investors for us that will just get what you're talking about. Thank you


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