IT Strategy Matters: The 12 Days of IT Strategy (a festive reset for leaders who want 2026 to go better than 2025)
Dan Coleby
Forwarded this email from a colleague? If you would like to receive future editions directly, you can sign up via my website
December is always a funny month in IT.
Half the organisation is trying to finish “one last thing before Christmas”. The other half is already mentally on leave. Meanwhile, you are staring at a list of unresolved risks, half-delivered projects, and next year’s budget, wondering how on earth it all fits together.
If that sounds familiar, you are not alone.
The end of the year is actually a brilliant moment to do something that rarely happens in the rush of normal working life: pause, take stock, and reset your strategy.
So, in the spirit of the season, I have put together The 12 Days of IT Strategy.
Think of it as an advent calendar for IT leaders. It is not about perfection. It is about small, meaningful actions that will make your strategy clearer, your delivery easier, and your next year more successful.
If you do nothing else this month, pick three of these and do them properly.
Day 1: Write down the outcome you actually want
Not the project. Not the technology. The outcome.
If you cannot describe your IT strategy in one sentence that starts with “We will improve…”, you will struggle to align your team and your stakeholders.
Quick action: Write one sentence for the year ahead. Then ask three stakeholders if they agree it matters.
Day 2: Name the constraint that will bite you
Every strategy has a constraint. Usually several. Capacity, skills, funding, procurement, security, change fatigue.
Ignoring constraints does not make them go away. It just makes your plan fictional.
Quick action: List your top three constraints and what you will stop doing because of them.
Day 3: Decide what you are not doing next year
This is the hardest day.
Most IT plans fail because they are a list of “yes” decisions with no “no” decisions. The organisation hears “we are doing everything”, so it expects everything.
Quick action: Create a “not doing” list. Share it with your leadership team. Watch the conversation get real.
Day 4: Check your strategy has an owner, not just a document
A strategy without ownership becomes shelfware. Ownership is not just governance. It is someone being accountable for outcomes, trade-offs, and momentum.
Quick action: Name the owner for each major strategic theme. If you cannot, you have found a risk.
Day 5: Do a one-page map of the current reality
Before we paint the future, we need to see the present properly.
Most IT teams have lots of information, but not a shared view of reality. That is why debates go in circles.
Quick action: On one page, capture:
-
What is working well
-
What is not working
-
What is fragile
-
What is blocking progress
Day 6: Identify one piece of technology debt you will actually repay
Technology debt is not a moral failing. It is an economic reality. But if you never pay any of it back, you will eventually lose freedom to move.
Quick action: Pick one debt item that is causing daily pain. Define what “repaid” looks like and put it on the plan.
Day 7: Make one decision about data
Most modern strategic ambitions, especially anything AI-related, depend on data being accessible, governed, and useful.
If your data is a mess, your strategy will be held hostage by it.
Quick action: Choose one:
-
Improve data quality in a critical domain
-
Reduce duplication of core data
-
Clarify ownership of data
-
Fix access and security around sensitive data
Then write a simple plan for it.
Day 8: Make security a design choice, not an afterthought
Security is easiest when it is baked in. It is painful when it is bolted on.
This is not about fear. It is about reducing friction. When the secure route is also the easy route, people follow it.
Quick action: Choose one control to strengthen in a way that improves experience as well as risk, such as better authentication, safer device posture, or simpler reporting of suspicious activity.
Day 9: Decide what “good” looks like for your users
IT strategy is not just internal. It is experienced by real people doing real jobs.
If you are not explicit about the experience you are aiming for, you will accidentally optimise for internal convenience.
Quick action: Write a short “day in the life” of a user in 12 months’ time. What is easier? What is faster? What no longer happens?
Day 10: Convert one project into a product mindset
Many IT functions still run everything like projects. But the work that creates long-term value is rarely “done”. It evolves.
A product mindset improves adoption, accountability, and continuous improvement.
Quick action: Pick one key service or platform and define:
-
The outcome it exists to deliver
-
The measures that show success
-
The roadmap you will iterate
Day 11: Plan how you will create belief
This is the “change” day.
Even the best strategy fails if nobody believes in it, understands it, or has the confidence to support it.
Belief is created through involvement, clarity, and visible progress.
Quick action: Identify the groups who need to believe in the strategy, and one action you will take with each group in Q1.
Day 12: Create a simple rhythm for governance and learning
Most strategies are written once a year and then ignored. The best strategies are revisited, tested, and adapted.
You do not need a complex governance structure. You need a rhythm.
Quick action: Put three recurring sessions in the diary for next year:
-
A monthly review of progress and blockers
-
A quarterly “are we still aligned?” check with stakeholders
-
A twice-yearly reset based on learning and changing conditions
A final thought for the season
If you are reading this at the end of a long year, feeling tired and slightly overwhelmed, I have good news.
You do not need to solve everything in December.
But if you can create clarity about what matters, and take a few deliberate actions that reduce friction for next year, you will be amazed how much easier January becomes.
Pick three days. Do them well. Then enjoy the break.
And if you would like a hand turning these prompts into something your leadership team can rally around, that is exactly the kind of work I love doing.
Might I be able to help you?
-
If you want a light-touch IT strategy reset session for your team, reply to this email or get in touch here and let's talk.
-
If you want ongoing support, ask me about coaching or a bespoke engagement.
Thank you for reading, and for your support throughout the year. I'm really proud of the community that we are building together and that more people are thinking differently about how to define and deliver their IT strategy.
Until next time, remember: IT strategy matters!
Dan - The IT Strategy Coach
IT Strategy Matters
Newsletter from The IT Strategy Coach, sharing thoughts, ideas and IT strategy community insights. Sign up here! Note that you will receive an email asking you to confirm your subscription. If you don't get this, check your Junk email folder!
Responses