An imaginary IT Project Director is dropping some truths about IT Project Management right now – and readers are LOVING it. (see readers comment at the bottom)
Chapter One: Helen’s Mad Idea
To paraphrase my colleague Helen: We should probably start by admitting whose fault this is.
It started on a Tuesday evening, somewhere around the second glass of Primitivo, when Stoneseed’s Marketing Manager Helen found herself wondering what it would actually feel like to be a middle-aged IT Project Director trying to deliver an AI transformation programme while the organisation slowly rearranged itself around him.
The answer turned out to be Gary Clencher.
If you haven’t met him yet, Gary is the fictional 51-and-three-quarters-year-old hero of a diary series Helen’s been writing – styled, quite brilliantly and deliberately, on Adrian Mole. (Diary note: I wish I had a pound for every time Helen has had to explain who Adrian Mole is to a younger member of the team. I’d have £11!)
Gary has a RAID log that grows every time someone tries to shrink it.
He has a colleague called Trevor who attends meetings, says almost nothing, and writes things down in a way Gary finds “actively threatening.”
He has written a six-page policy about how to write prompts for an AI tool, using the AI tool, and noticed the irony a little too late to do anything about it.
To be honest, we didn’t expect much from Gary Clencher beyond a laugh in the office. Three instalments in, it’s been forwarded round more inboxes than anything else we’ve put out this year – and not because it’s clever (I mean, it is clever, in case Helen reads this). It’s more because people keep recognising someone, usually, themselves but it also turns out we’ve all worked with our fair share of Trevors.
Chapter Two: Gary, As It Happens
Here’s the uncomfortable bit. Gary isn’t really a joke. He’s a composite. None of the characters we meet are real – and yet we instantly know them. You can easily open up your contacts in your phone and point to the Priya, Deborah or Rob in your life (I just got off the phone with my Priya). It’s all beautifully well observed.
Take the bit where Gary’s tidy, fourteen-person Prompt Engineering Policy gets “absorbed” into a 3,400-person Company AI Adoption Policy within about 48 hours, on a six-week timeline, with a budget marked “to be confirmed” – which, as Gary correctly notes, means no. Anyone who’s watched a sensible piece of work get adopted as the foundation of something much bigger, much faster, with none of the resourcing to match, has lived their own version of that week.
Or the moment Gary asks the AI to help him write a policy governing how staff are allowed to use AI, and quietly parks the philosophical problem with everything else he’s not dealing with this week.
Or Trevor’s nineteen-minute “light-touch governance review” that produces eleven written observations and zero spoken words.
Or the RAID log item that gets logged twice, because nobody quite owns it.
None of this is exaggerated for effect, particularly. It’s just what a programme looks like from the inside, with the diplomatic language stripped out.
Chapter Three: What We’d Actually Do With Gary
This is the bit where we stop laughing and look at why it’s funny.
Strip away the jokes and Gary’s diary is a fairly accurate map of what actually keeps an IT Director awake at night.
There’s the strategic fear: scope expanding faster than resource. Gary’s Prompt Engineering Policy that I mentioned earlier, for example, that becomes a Company AI Adoption Policy. That’s not a “Gary problem” – that’s what happens whenever a good idea gets adopted upward without anyone asking who’s actually going to deliver it.
There’s the operational reality underneath: a RAID log that grows every time someone tries to shrink it, the same risk logged twice because nobody’s quite sure who owns it, and three different stakeholders – Patricia, Vanessa, Trevor – all wanting something slightly different, none of them wrong. Most programmes don’t fail because the thinking’s bad. They fail because nobody’s holding the unglamorous, constant work of tracking, owning and rationalising all of that while the Director is busy doing everything else.
And then there’s the personal bit, which is the one people actually message Helen about. The dread of being quietly outpaced by your own team – Priya asking the question Gary should have asked eighteen months ago. The eight-second silence after a slide nobody understands. And the moment Deborah takes ownership of the RAID log and Gary realises, with some relief, that a problem has stopped being only his.
That relief is the whole pitch, really. Gary doesn’t need less responsibility. He needs someone else properly holding the parts of the programme that are eating his week – the tracking, the governance discipline, the dependency mapping – so the things only he can do (the judgement calls, the board credibility, the actual leadership) get his full attention instead of the leftover 20%.
That’s what PMaaS is, underneath the acronym: not a replacement for Gary, but the Rob, Priya and Deborah that Gary Clencher didn’t have in week one.
If you bump into Gary, give him Stoneseed’s number (01623 723910). Just not yet, eh? Let’s see what happens in the next chapter, before we send in the cavalry to save the day.
I mean, “Day One – Phoned Stoneseed and they fixed everything” would not have been nearly as entertaining.
Next chapter please Helen.
Readers Comments
- Brilliant, more please. And please let Gary know that the first job I got Claude to do was to scrape my local authority website each week and email my husband which bins to take out! Sadly I can’t automate him reading my emails…. CIO/Transformation Director
- I’ve no idea how this found my feed – that’ll be “the AI did it!” – but I’m so glad it did. Please continue!! -Director of Transformation & Change Programme Management office
- This was brilliant – please write more! Turn it in to a book!! – Coaching and tailored consultancy
- Loved this- more please. Perked up my Friday morning -Transformation Director
- Loved this on a rainy Thursday – thank you Helen. -CEO
- Guffawed out loud (only Copilot was listening and asked me to spell it). Me, 53 and not even a quarter. Please write more – Programme Delivery
- This made me laugh a lot. Guffaw actually to steal the word above used by another reader. Can’t wait to read the next instalment. – IT Programme Manager
- It’s hilarious actually….yes we want more. (Written by me not A I) -Business Development Co-Ordinator
- Even funnier reading it the second time! – IT Systems Manager
Read the story here:
Weeks 1&2 (25) The Secret Diary of Gary Clencher, I.T. Project Director – Aged 51 and ¾ | LinkedIn