The right questions to ask before 2027 planning begins

Good digital planning starts with the right questions. Most organisations know what they want to achieve digitally in 2027. Fewer have a clear enough picture of their current estate to know where to start. 

The September planning window 

For most charities, the shape of 2027 is beginning to form. Budgets are being set, priorities are being agreed, and the conversations that will determine next year's direction are already underway. Digital strategy is typically one of the harder ones to conclude. The questions surface: which platform to prioritise, what the website needs to do differently, how AI fits into the picture. But without a clear enough picture of what's actually driving performance, those conversations tend to circle rather than land. 

That clarity doesn't arrive on its own. It requires a structured look at what the digital estate is actually doing, what's causing the results being seen, and what the right order of investment looks like. That kind of thinking requires time and space - and September, before the noise of Q4 takes over, is when both still exist. 

The organisations that use this window well don't just arrive at 2027 with a list of digital projects. They arrive knowing what problem each one is solving, why it comes before the others, and what success looks like. That's a fundamentally different starting point to carrying the same unresolved questions into another planning cycle. 

Where most digital planning goes wrong 

The case for getting digital clarity before 2027 is straightforward. What’s less straightforward is knowing what good digital planning actually involves - and where organisations most commonly go wrong. 

Three patterns show up consistently across the sector: 

The first is solving for the presenting problem rather than the underlying one. The 2025 Charity Digital Skills Report found that a lack of data know-how is one of the most common challenges charities face with their digital systems - and in our experience, this shows up most clearly in how decisions get made. Organisations invest in user journeys, donation flows, and website redesigns without a clear picture of what's actually causing underperformance. The symptom is visible and feels urgent. The root cause sits underneath it, less obvious and harder to address. Investment lands on the wrong thing, and twelve months later the same conversations are happening again. 

The second is making platform decisions without a clear picture of how everything connects. Only 44% of charities have a digital strategy in place - down from 50% the year before. Organisations without that strategic foundation are more likely to make platform decisions in isolation: choosing a new CRM without a clear view of how it needs to connect to the donation platform, the email system, and the way supporter data flows across the estate. Putting it plainly, migrating data into a new system without first understanding what you’re working with means you now have the same problems in a more expensive system. 

The third is treating digital as activity rather than infrastructure. When digital is treated as a series of discrete projects rather than a connected infrastructure - a website here, a new tool there - organisations build capability that doesn’t compound. Each investment solves an immediate problem without really moving the organisation any further forward. 

The questions worth asking now 

Good digital planning doesn’t start with a list of projects. It starts with a set of honest questions about what the digital estate is actually doing and why. 

Do your systems produce the data you need to make decisions?

Over 75% of charities report low data literacy, and disconnected systems are a primary reason - staff spend time manually compiling data from multiple sources rather than drawing on integrated insight. The question isn’t whether data exists. It’s whether it’s usable. 

Do you know whether your digital challenges are symptoms or root causes?

The most common and expensive mistake in digital planning is investing in a solution to the wrong problem. Identifying root causes - rather than the issues that present most visibly - is what makes subsequent investment land in the right place. 

Is there a shared view across your organisation of what digital needs to do in 2027?

Without a clear strategy, digital decisions default to the most urgent request, the loudest voice, or the most visible problem - rather than a considered direction that the whole team can get behind. 

What does the right order of investment look like?

Knowing what to change is not the same as knowing what to change first. A prioritised roadmap - mapped against impact versus effort, and built on a diagnosis of what’s actually causing underperformance - is what turns intent into action. 

What changes when the picture is clear 

Organisations that arrive at 2027 with clear answers to those questions are in a fundamentally different position to those still carrying them forward. 

The most immediate difference is in how decisions get made. When root causes are understood, the order of investment becomes logical rather than contested. Teams stop debating which platform to move to and start agreeing on what they are trying to achieve. Budget conversations become easier, because the case is built on diagnosis rather than assertion. 

The second difference is in how digital investment performs. A prioritised roadmap is not just a list of things to do - it is an investment framework. Each item has a clear rationale, a defined objective, and an expected outcome. That makes measuring return possible in a way it simply isn’t when investment has been made against a problem that wasn’t fully understood. 

Across our work, we've consistently seen organisations arrive with a clear plan - a platform migration already budgeted, a rebuild ready to commission - and leave with a different one. Not because their instincts were wrong, but because the diagnostic process identified where the highest-impact investment actually lay. That shift in direction is often where the most significant value sits. We've helped organisations use that clarity to secure internal sign-off on projects that had previously stalled, to build funding applications strong enough to attract external investment, and to move from reactive digital spend to structured, planned investment that compounds over time. 

About Giant Direction 

Giant Direction is a consultancy service designed for exactly this challenge. We work with you through your digital challenges - separating root causes from symptoms - and deliver a written diagnosis and prioritised roadmap: what to do now, next, and never.  

September is the right moment to start. Beginning now means having that clarity in place before 2027 planning begins in earnest - rather than carrying the same questions into another year.   

If you’re ready to find out where to start, that's what Giant Direction is for.