In this Newsletter we’ll talk about common reasons why IT Strategies fail, what failure means in the context of IT Strategy and what you can do to avoid common pitfalls and maximise your strategies chance of success

What is Failure?

I guess when we initially think about what failure might be in the context of IT Strategy its simply “We haven’t executed what we said we would in the timescale that we said we would” I think this sort of framing can be problematic, why? well partly because by that definition i reckon 90% of all IT Strategies are failures.

I think in the context of IT Strategy a more useful definition of failure is about a lack of movement in Two directions:

  1. Failure to move strategic IT capabilities forward enough (a good clue on this is are you still dealing with the same issues/complaints/risks you dealt with before you defined your strategy, or are you now working on new ones?)
  2. failure to move the business forward in achieving their strategic objectives

Why does this happen? i’ll list out some common reasons and how to try to avoid them

Common Reasons

Reason 1

Failure to address the real needs of the business.

This is extremely common, an IT Strategy is created that might look and smell like a reasonable IT strategy, talking about sensible things that other strategies talk about. However it does move IT or the business forward because the strategy has not identified and addressed the real needs of the business. As a result the IT Strategy effectively becomes useless as the true strategic imperatives of the business wash away the sensible but ill-informed IT Strategy.

How to avoid:

In my upcoming How to IT Strategy course we’ll go into more detail about how to ensure your strategy meets the real needs of the business. A couple of key actions to mitigate the risk are:

  • Ensure you put enough time and effort into stakeholder engagement
  • Ensure you are clear on the Business Strategy and the role that IT needs to play in delivering it, and if the Business Strategy is not clear, challenge it!

Reason 2

Failure to address perceived needs of key stakeholders.

You define a strategy, you start trying to execute, but the work you want to do that’s aligned to the strategy keeps taking second place to the demands from your key/senior stakeholders

How to avoid:

Another way of terming this would be ‘lack of executive support’, but in reality that essentially boils down to the same thing, you haven’t identified and addressed your stakeholder needs. As with reason 1, the risk of this occurring can be mitigated through effective stakeholder engagement to both understand need and influence and inform stakeholders.

Reason 3

Being ‘Tactegic’ not Strategic

This can come in Two forms:

  1. Your strategy is too myopic and is a collection of tactical moves to address short term issues or stakeholder wants
  2. Your strategy is overrun by stakeholder desires for short term tactical work that does not progress the strategy

How to avoid

To avoid 1) think about the foundations of your strategy, what are the key pillars that provide the platform for execution? thinking about capabilities rather than technologies helps raise our thinking beyond the short term and tactical

One approach to Avoiding 2) is similar to how you avoid 2 and 3, ensuring your strategy really is addressing business and stakeholder needs, but equally important is that you make use of whatever governance structures you have in your organisation to ensure you are able to simply say no to work that does not align to the strategy. What if you know your governance structures aren’t strong enough for you to rely on them? well then you’ll need to plan to address that as part of your IT Strategy.

Reason 4


You define the strategy, start to execute and then realise you’ve bitten off more than you can chew and you’ve overcommitted your resource and over promised to your stakeholders.

How to Avoid

Estimating accurately is notoriously hard, there are a couple of things i’ve found useful when thinking about the the possibility of overstretching:

  1. Use your knowledge of the history of change within the organisation (specifically within the organisation). Did that laptop refresh take 12 months instead of 6? is this new strategic objective of a similar scale/complexity? then use that as your benchmark
  2. Effective prioritisation of the core strategic IT imperatives and being conservative in your commitments. There is a saying that a road at 100% utilisation is a traffic jam, your teams need space to think, be proactive and innovate within the strategy.

Reason 5

Not having a foundation for execution

You can’t execute the strategy because you simply don’t have the fundamental foundations (people, skills, culture, base technology) to deliver

How to avoid

You need to be honest about:

  1. What are the foundational capabilities (team, culture, technology platforms) that all your endeavours are based on
  2. Their actual ability to help you deliver

In previous Newsletter we’ve touched on how to assess teams and culture, check them out if you haven’t already.


In this Newsletter we’ve discussed why do IT Strategies fail, what failure means, what common causes of failure are and how to avoid them.

In my upcoming course ‘How to IT Strategy’ i provide a pragmatic and proven approach to IT Strategy creation, that amongst other things helps you significantly increase the chance of creating and executing a successful IT strategy. you can sign up for early bird access and an early bird discount at

Please subscribe to this Newsletter so you don’t miss out on the next instalments. If audio is more your thing you can get the companion ‘How to IT Strategy’ Podcast on Anchor, Spotify , Apple Podcasts and all major Podcast Platforms

Why do IT Strategies fail?