For this newsletter I thought i’d share some (anonymised) examples of mistakes i’ve made when creating IT strategies, i’m doing this for a couple of reasons:

  1. You might find them amusing “haha look at Richard, what an idiot!”
  2. You might find them useful when thinking about your IT Strategy work
  3. I think the mistakes i’ve made that i’ll share in this post are examples of wider pitfalls or Strategy creation anti-patterns that it can be useful to be aware of and avoid (of course these may well be very obvious, you are already aware of in which case this post will mainly be 1) :)

Settling, a missed opportunity

One time I worked with a medium sized public sector organisation, working with their IT Director and his boss, one of the Exec Directors to create a new IT Strategy for the organisation. For a variety of reasons the IT organisation was long overdue a shake up with an outmoded view of its role in the organisation, for example barely started on an IT Service Management journey, and an outmoded way of delivering technology e.g. when i started working with them they were just about to start on a physical to virtual migration of their main ‘datacentre’ which was a large cupboard in the basement of one of their buildings.

The strategy that we came up with was pragmatic, it made steps in the right direction, it was definitely achievable (I later worked with them on the implementation planning and project) and was welcomed by all the key stakeholders and signed off easily. But did we transform their colleague’s and customer’s experience? Did we help the organisation make a step change through their use of technology? No and thats why, even several years later i feel like there was a missed opportunity to really challenge (ie potentially piss off) the IT leadership and create a more ambitious IT Strategy

What is the lesson here? Creating a great IT Strategy should not be a comfortable experience. It should ruffle feathers, it should cause debate, disagreements and lead to people shifting their positions and challenging their assumptions, because if the opposite of a strategic decision is not an equally plausible option, you probably aren’t making an important strategic decision.

Missing stakeholder expectations

One time i was working with another business on their IT strategy, i thought i’d done a good job of engaging with all the right stakeholders and created a great IT Strategy. I had a session presenting back a summary of the strategy to a group of the key stakeholder, senior managers drawn from across the organisation. The presentation (and I) absolutely bombed. Despite the 121 interviews I’d had with many of the stakeholders and making sure i’d addressed their concerns and needs in the strategy, I’d not addressed a really key element. They had zero confidence in the IT leadership team’s ability to deliver, what they expected, but hadn’t quite had the confidence to express in my interviews with them (or I hadn’t been able to get them to feel comfortable enough to express) was they wanted a root and branch change in the IT organisation (and essentially a hatchet job from me). Several months later and a change in the IT Directors line manager, they did eventually get what they wanted.

What is the lesson here? Essentially i’d failed in my engagement with the stakeholders, I thought I’d understood their needs and their criticisms of the current state individually, but hadn’t stepped back and understood the totality of the weight of their concerns. Also, as an outsider i’d probably missed a whole layer of politics that an incumbent in the business may have been aware of (sometimes as a consultant thats a good thing, in this case it wasn’t).

Criticising the wrong person

One time i worked with an organisation to develop an IT Strategy, I spoke with a senior, non IT stakeholder and was surprised to learn that this person was working with an external company developing a software solution for their business area, spending £900k (for comparison roughly 15% of the IT Org’s annual budget) an over estimated 18 month period, with zero IT involvement in the process, limited business involvement, no previous experience of delivering software projects and no defined delivering process beyond ‘we give them money and 18 months later they give us software’. Naturally I challenged the stakeholder on the approach and raised my concerns. What became apparent in subsequent meetings was that this stakeholder had strong senior support and essentially a licence to do whatever they sort fit to support and grow their business. My challenge in this area was unwelcome, lacked senior stakeholder support and I ultimately didn’t get to complete my strategy work with the organisation because of it.

What is the lesson here? well part of the lesson for me is about integrity, the strength of my challenge in this area was me acting in the best interests of the company. Another lesson was again around understanding the stakeholder landscape, I have to admit my initial and subsequent challenges were actually not at the right level, leading to a ‘he said this’ scenario that ultimately led to me not continuing to work with the organisation.

(Oh and no the 18 month £900k project didn’t stick to time or budget and i heard it ultimately got canned)


In this post i’ve talked about 3 examples of mistakes i’ve made in creating IT Strategies. The common theme in each of these mistakes highlights the absolutely fundamental importance of effective stakeholder management. The best IT strategies will fail without engaged and bought in stakeholders. Without stakeholders onboard a strategy can fail even before we get to Implementation.

IT Strategy mistakes