Head of IT – The ingredients list & the five things you need as a Head of IT or Technology

Mario De'Cristofano 16th August 202416th August 2024 0 Comments

Head of IT – The ingredients list & the five things you need as a Head of IT or Technology

If you dont want to read the post, why not listen to it on the Delivery Manager Daily?

I spend a lot of time writing about efficiencies & understanding where to place my effort for maximum results in the shortest time. From personal time management to effective planning techniques covering things from handling global timezones to practical tools & assets. I think its really important to have a think about what you can weaponize as part of your ‘go to’ toolbox as you deploy yourself in your role. Some ideas are not as obvious as you may think!

As I interview & hire IT staff, I am somewhat surprised that folk don’t spend more time thinking about & executing some of this stuff so thought I’d write about it in effort to help others & start a conversation. Feel free to take notes, copy the links & tell me what’s in your toolbox. I’m interested in hearing the tools you use.

What ‘is’ Personal Investment?

When I talk to a lot of peers, colleagues staff & friends, they often consider investment for things like training & paying money on the latest Agile or technical certification, but they never invest in equipment that will save time. A good quality laptop or decent headphones or a good set of travel accessories – these things cost up-front capital but you save time in the long run because ‘it just works’. Instead, they opt for employer provided crap which often limits performance & give a reason for excuse.

I always encourage folk to think about spending money (even if it means using a credit line & paying it off over time) on the very best tools & software that enables the best productivity. But also, think about the documentation you’ve created & how much of it you redo every time you go into a new role. Think about creating ever-green content that you can use (within reason) again & again. I talk about it here in a recent episode of the Delivery Manager Daily podcast (please like & subscribe)

The Five Things You Need As Head of IT

Here are in my opinion, the five critical things you will need then to help you have success in your Head of IT role.

1 An established vendor personal network

You will need ideally to be able to call upon tried & tested contacts to help you deliver your strategy. Whether that’s a well-known VAR you’ve used before, a hardware provider or software account manager, these contacts will help you expedite any of your planning & strategy. It’s in their interest to keep that relationship with you & you can leverage the known quantity of using somebody you’ve used before. I have a go to list of people to help me implement;

Single hardware vendor provisioning
Cloud platforming & architecture
Recruitment
Physical building fit-outs
Marketing & digital media

I recognised the need for this early on in my career & I’ve made a conscious effort to build & nurture relationships to be able to leverage them later in my career. Sometimes you build the relationships with the organisation from a brand perspective, sometimes its individual folk, but it’s a small world so you’ll do well to invest in relationships.

2 Access to turnkey processes collateral & documentation

I’m not saying you can cookie-cutter everything in life, but in my entire career I’m still using the frameworks of processes, policies & procedures no matter what the organisation. Things like acceptable use policies, strategic roadmap templates, BYOD, the use of Ai in the workplace, you should be able to call upon pretty well finished documentation that covers these topics (& more) to be able to refine, personalise & use quickly. I’ve talked about creating evergreen pieces of work before & you should consider the time/effort you spend on creating throwaway documentation that you constantly re-cut & redo, versus work you spend more time on initially but can then re-use. A ‘toolbox’ if you will. I regularly use my;

Agile 101 training, from principles of Agile & Lean, to workshop templates, Miro boards & deployment plans for tooling like Jira.
Project Management & reporting – RAG & status reports, RAIDD, roadmaps & timelines, all able to spin up at a moment’s notice.
Perfected your Jira ticket template, your DoR or DoD, or even how you spin up a project in Confluence? I have, I use it all the time, so I make a note of it so I don’t need to think about it when I start up a new project or need to give a team advice on how to structure theirs.
BC/DR planning
General document template structure – You should know how to write a good document, create a single template you can skin & brand no matter the company you work for.
Budget & Accounting management spreadsheets
Cost of downtime templates
IT Staff training & skills matrix & management
IT surveys

3 Cloud planning & adoption templates

You really do need to be comfortable & familiar with all the great planning & provisioning tools the major cloud vendors offer at no-cost, to help you with your next cloud project. From Microsoft’s Cloud Adoption Framework (here) to AWS’s assessment tooling (here). Resources such as these are a great start for your cloud project & ensure you’re baking in governance right from the get go. I’ve compiled this small list which I use regularly;

Microsoft Azure Pricing Calculator

4 Good equipment & travel tools

I’ve never prescribed to relying on your employer (especially at senior levels) to provide & provision your tools. For me, it’s akin to being a bricklayer & you are expecting the site foreman to provide your trowel & cement! Think about how you can be ready & deployable at any time as an ‘asset’ to either run & facilitate a workshop, start on-site & be self-reliant immediately etc. So ensure you have at least;

High quality laptop(s) & mobile & travel computing accessories
Backup computing & security (portable encryption-able hardware)
Convenience tooling (to help you do your job quicker)
Conference tooling – good quality speakers, microphone/headset

I really do think if you want to perform at a high level you should be using high quality equipment. I put at least two bags together with duplicated kit so I can provision some blindly for my client or organisation (& not have to worry about complying with BYOD policy) but also being ready to travel in various go-bags. So for an overnighter, I have provisions in my car, then at home in the wardrobe I’m packed & ready for a week & two weeks respectively.

5 Investment in personal tooling

Like hardware & kit, don’t skimp on software. I’m always surprised at how many people think investing in themselves is just about qualifications, but its also your tools. Just as a good tradesperson has their van kitted out beautifully so should you. There’s tooling I rely on that I take with me & stomach the costs of the membership plans, month on month. Here’s some of the tooling I use;

Miro (For planning & meeting workshop facilitation)
Adobe Creative Cloud – For asset creation, video editing & media production
Ai tooling (Chat GPT, Claude AI, Copilot)
Office 365 Professional
Azure, AWS & GCP subscription

I justify the cost of all the above as I use them literally every day for hours. Consider the tooling you’re using on a daily basis & consider investing in it yourself.

Bonus – Your thumbdrive

I’m always keen to keep my hands ‘on-the-tools’ so no IT guy would be complete with out a thumb drive full of useful tools, so as a bonus, here’s my top 5

Ventoy – Ventoy is an open source tool to create bootable USB drives for all kinds of file formats without having to format a fresh thumb drive over & over again.

Medicat– Medicat is a toolkit containing password removal tools, ransom & malware recovery, disk utilities & backup & data recovery tooling, all in one place.

Liberykey – Liberkey contains major but free tooling across audio, video graphics, internet, education etc. Its good if you want to be fully open source or get a job done.

Winaudit– to quickly & efficiently audit PCs

WindirStat portable – to visually understand what is taking up hard drive space quickly

Your toolbox is an extension of you, what you do & how you do it.

So for me, that’s what I consider to be a pretty exhaustive list of all the things you want to consider putting together over-time to help build your arsenal as an IT pro. Some of them you should have sooner rather than later, some you can build up over time. So whether you’re building up a longer term strategy or maybe thinking about a 100 day plan think about the tooling you use to, to be effective both in terms of delivery & time management.

References & Links