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Avoiding Project Failure: 5 Traits Of Highly Successful IT Project Managers

IT Strategy local_offer

A few years ago, almost 600 IT professionals and their business counterparts were interviewed by Geneca about their IT project management expectations — with shockingly gloomy results.

What stood out was the overall lack of confidence in project success: 75% of the business and IT executives who were questioned in the study said they anticipate their projects will either always or usually be “doomed right from the start.” Moreover, IT Transformation projects are no exception — actually, they are quite the opposite. These types of highly complex, multi-year projects are notorious for having high failure rates.

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IT Project Failure Is Avoidable

What is the reason for such a high failure rate? Moreover, can it be remediated?

According to a study by PricewaterhouseCoopers, 60% of project failures are linked to internal project issues. The analyst company explains further that the three primary reasons for project failure are all internal project factors (bad estimates/missed deadlines, scope changes, and insufficient resources) and comprise 50% of the reasons why projects fail.

So if the top reasons are internal project factors, then you can identify that they can be fixed with the right project management people, tools and processes! Many enterprises have caught on to this fact! Instead of taking failure as a given, executives strive to hire the best IT project managers and equip them with the project management tools and resources they need to achieve success. 

But having said that, you know that being an IT project manager is a tough job that comes with much responsibility. So what exactly is it that sets great project managers apart from mediocre ones?

Over the past years, we have helped hundreds of enterprise IT project teams ready more than five million assets for migration. In  working with lots of different project managers across numerous industry sectors and delivery models (outsourced/insourced), we have experienced firsthand what it takes.

1) Always Align With Business Goals

It is all too easy for any IT project manager to back out of a potentially failing project by saying, "The scope changed so much we couldn't deliver it".

However, how do companies justify spending hundreds of thousands or even millions of dollars on IT transformation projects every year if this investment is not paying off by helping them achieve better outcomes (e.g., by increasing end-user productivity or data security)? Unfortunately, scope change is almost inevitable in such large projects - it is how you manage that change with your business executives and sponsors that will define your success.

Sadly, the reality is that many projects are not properly aligned with clearly defined scope and outcomes. For example, most IT professionals and their business counterparts in the above-mentioned Geneca study said they are often unclear about the goals and objectives of the project. They feel there is a lack of engagement, as well as poorly defined project requirements and boundaries. Fewer than 20% stated that their project requirements are defined in the form of business need. 

How can you avoid falling into that trap? Instead of focusing on just "going live," we have found that successful IT project managers strive to ensure that their project drives business improvements and involve the business throughout the project delivery cycle. They always plan for the plan and ensure that this massive undertaking does not get lost along the way by asking questions like:

  • What is the expected business benefit from the project?
  • Have the business objectives been agreed to by senior management as well as other business stakeholders?
  • What are the key business milestones?
  • What are the primary business risk factors?
  • How do we ensure that the project delivery is engaging with our stakeholders?
  • How do we keep the project risks, issues and activities transparent with our business sponsors?
Read More: The Basics Of Planning An Enterprise Windows 10 Migration


2) Have A Strategic End-to-End Vision

Many times, we find that some project managers only plan their projects to the next hurdle.  For example, some will consider that IT asset discovery is the key deliverable, only to find that what is discovered needs a large amount of categorization, normalization and rationalization work.

They believe everything will fall magically into place if they could only figure out how to get the data. However, if you are planning a resource- and a time-intensive project like an enterprise-wide Windows 10 rollout, getting that data is technically "easy" — it is what you do with it once you have it that matters. 

A project of this scope means juggling thousands of activities at the same time while managing dozens of interdependencies such as hardware procurement or application readiness bottlenecks. With a project so complex and lengthy, it can be overwhelming to think the entire thing through to the end when you have not even started yet.

To provide the foundations for success, you will need to create a business plan, including budget, resourcing and timeline before you even have gotten your feet wet and discovered what you are dealing with. At this point, you do not have an exact understanding of what state your IT landscape is in or how many applications are compatible and which will need re-testing or even re-write. 

However, even though (or precisely because) you are dealing with a large number of uncertainties, having an end-to-end strategy and vision of your end goal is crucial to the success of your project. By taking some additional time to better understand the current state environment against the target state deliverable, you will be much better positioned to understand the journey and potential pitfalls. 

3) Empower Stakeholders With Data

As we just discussed, defining your project requirements as benefits rather than features and getting executive buy-in as early as possible in the project is critical. However, it is equally important that, once you have buy-in, your executive sponsors are kept engaged throughout the process. You just cannot ask them to hang in there for three years before they will see results!

Moreover, while this theoretically makes sense, the reality looks very different. According to the above-mentioned Geneca study, 78% of respondents feel that "the business is usually or always out of sync with project requirements, and business stakeholders need to be more involved and engaged in the requirements process."


What can you do? We have found that projects where project managers who empower and engage with their stakeholders and business sponsors by delivering up-to-date and easy-to-understand information are more likely to be successful.

It is simple. Executives and project managers alike are not satisfied with guessing, estimation or the 'black holes' of project runtime that do not deliver any migration numbers. They do not want "maybe" or "perhaps" — they need to make informed decisions based on accurate data. They want the ability to have key insights readily available in dashboards and easy-to-understand reports that give them the information they need in the format they want. There is nothing more empowering for an executive sponsor that has invested significant budget into an initiative for them to be able to ask intelligent questions and receive real-time answers through project reporting transparency.

This engagement throughout the project also has a tremendous upside for you as a project manager. Instead of blaming others when things go south, your management team is forced to collaborate with you to resolve any arising issues, make decisions and stick by them. 

4) Make End Users Part Of The IT Project Process

No matter how long your project cycle, at some point, there is a time when you are impacting your end users.

As the project manager, you have two choices: You can keep the migration under wraps as long as possible to make as much progress internally as possible before having to roll it out. Or you can engage with your end users as early and often as possible.


While some project managers prefer the first method, we have found that IT project managers who whole-heartedly embrace the second way are a lot more successful.

By using automated email communication, you can engage with your users early and often, whereas self-service portals allow you to give your users the ability to validate critical data points that you would not be able to get access to otherwise. 

Aside from the technical benefits, you can create a pull-effect by getting your users excited and onboard with your project. It allows you to get access to early influencers. Our most successful projects are those where the end user has more control over what is happening to them and when.

5) Make IT Transformation Projects Iterative

According to PriceWaterhouseCoopers, change of scope is the second highest ranked reason for IT project failures. Since most IT Transformation projects span multiple years, project requirements will most likely change over the years as the business needs change as well. Stakeholders or key members of the team might move on to other positions, projects or companies.

Unfortunately, a common scenario is that your IT transformation project will need to remediate a number of things in business as usual before it can move forward. Sometimes this can be an entire shift in IT platform - for example a company that decides to move to Office 365 within a Windows 10 initiative. Other times, it is to remediate broken data such as users without a location, or applications without a business or technical owner.

While it seems tempting to plan one big bang project rather than a lot of smaller, iterative projects (because one larger project is often perceived as less complicated and cheaper than smaller iterative progressions), often the opposite is true.

Continuous IT transformation management practices such as 'Business as Usual' or Evergreen IT allow you to more effectively manage scope creep and executives' expectations. It is easier to set and keep in the lines of the defined deadlines and budgets.

However, most importantly, you can deliver tangible business impact a lot earlier, and you can reduce the overall risk as you apply lessons learned to your subsequent updates. 


It is not easy being a great, proactive and strategically-minded project manager — a job that comes with the burden of great responsibility but also great potential. With the right attitude, approach and tools, you know you can drive tangible business results! 

Click here to download the Windows 10 Project Plan Template