Transformational Technology Initiatives: Five Red Flags to Listen For


Liberty Advisor Group

As the familiar saying goes, “You learn more from mistakes than from successes.” Yet, when the stakes are high, learning from mistakes can cost time, money, and heartache.

Major transformational technology initiatives such as enterprise resource planning (ERP) projects are typically big, costly, and complicated. Even today, many fail to live up to expectations. As consultants, we’ve spent countless hours helping clients avoid or recover from mistakes – and unsurprisingly, avoidance is always less painful than recovery. In the spirit of helping you avoid costly mistakes in your transformational technology initiatives, we would like to share with you five expressions we commonly hear that tend to indicate there are problems on the horizon.

#1: “Never mind the past. Our focus is on the future.”

While this is a positive and helpful sentiment for life in general, in the context of a transformational initiative it typically means one of two things.

First, “My legacy systems are complicated. I don’t have people that understand them, and I don’t want to invest in the reverse engineering required to build that understanding.” Without this investment, you risk proceeding without understanding what needs to be unwound, adjusted, turned off, or left alone during your next stage of work. We’ve seen this mistake result in serious issues such as duplicate customer orders and billings, data contamination, inaccurate inventories, and financials that are extremely difficult to reconcile. Such repercussions can have a negative impact on your operations and your customers.

Second, the sentiment may translate to, “I’m not planning on applying any lessons learned from earlier work.” If you re-invent the wheel, the chances are that you’ll suffer many of the same growing pains you experienced in the past. Recognizing how history has shaped the organization’s culture, capabilities, knowledge, and toolkits go a long way towards building the right team and approach to accomplish today’s goals.

#2: “We don’t focus on requirement documentation because we are an agile shop.”

Using an agile development methodology is not an excuse to avoid documenting your work or articulating your requirements. Agile requirements may manifest themselves differently than with a waterfall delivery approach, but they should be present as themes, features, epics, user stories, and tasks. If you hear statement #2, be very concerned. There is a real risk that the program is skipping steps that are imperative for your initiative to deliver precisely what the business or customer needs.

It’s worth noting that while agile methodologies can be highly effective in many development shops, these are not always a perfect fit for every phase of every program. Take a large-scale ERP implementation, for example. Such projects almost always involve a tremendous amount of cross-organizational dependency. It’s crucial that in the planning phases, you allocate time to build an understanding of these dependencies. This reduces the risk of effectively shooting yourself in the foot due to a poor foundational decision made without considering upstream or downstream impacts. Resolving such decisions later in the program is typically far more costly than the upfront time and effort required to examine organizational dependencies and setting ground rules that support all impacted parts of the organization.

While it is certainly possible for development activities to happen in an agile manner, blueprinting your solution with broad organizational dependencies in mind can be very valuable in this situation.

#3: “Change management is mostly training. The investment can wait.”

Change management is an area where organizations consistently underinvest. It is essential to think beyond the training elements. Early considerations include how to build champions of the initiative within your organization, how you identify stakeholders and individual impacts, as well as what and how you will communicate to internal and external customers. Effective change management must occur throughout the duration of the project. Delaying and underinvesting in change management can hinder organizational support for the initiative, leaving stakeholders without the proper knowledge of what is happening, and ultimately resulting in painful or failed implementations.

#4: “We need our best people to run the business. They don’t have time to support this initiative.”

Your strongest operators will give the initiative the highest likelihood of providing real value to the organization. Their deep understanding of how the business operates fuels the most impactful ideas and takes into account the operational nuances that could impact productivity.

Your best people are often viewed as such because they are skilled at identifying and correcting inefficiencies. They show promise as future leaders. Allowing them to contribute to major initiatives gives them the opportunity to optimize day-to-day operations, and to advance their careers in the process. Backfilling their regular work by training additional resources can also reduce risks posed by a lack of distributed knowledge within the organization. When embarking on a transformational initiative, we often recommend that our clients consider how they can support their best people’s daily operational responsibilities to allow their dedicated engagement on the initiative. Consideration should also be put into roles for these resources after the initiative is complete.

#5: “This is an IT project.”

Technology is an increasingly important part of how organizations operate. In today’s world, if a key piece of technology goes down, your organization can be ‘dead in the water’. This technology is there to support the needs of the business, and if there were no business, there would be no need for it. For this reason, there are very few true “IT projects,” yet there are many business projects that need the support of the IT organization. We’ve seen many organizations fail due to an ineffective culture, where business operators give the IT department primary goals and ask them to figure out how to use technology to meet them. Without sufficient levels of support from the business, the IT team is left to interpret poorly defined requirements, which can lead to solutions that ultimately do not meet internal or external customer expectations.

To ensure the greatest probability of success in a transformational initiative, we frequently recommend that the initiative be business-led and IT-supported – and not the other way around. If the initiative’s intent is to maintain or improve the way the business operates, it makes sense for it to be led by the people who best understand how the business operates.


Keeping a transformational technology initiative on track is vital and knowing how to identify potential red flags is key: If you have a transformational initiative in progress or are looking for more transformation and assurance material, Liberty Advisor Group service offering can be located here.


Liberty Advisor Group is a goal-oriented, client-focused and results-driven consulting firm. We are a lean, handpicked team of strategists, technologists, and entrepreneurs – battle-tested experts with a steadfast, start-up attitude. Our team, with an average of 15+ years of experience, has delivered over $1 billion in operating income improvement and over 300 M&A deals for our clients. We collaborate, integrate and ideate in real-time with our clients to deliver situation-specific solutions that work. Liberty Advisor Group has the experience to realize our clients’ highest ambitions. This year, Liberty has been named to the 2019 Best Places to Work in Chicago and to FORTUNE’s list of Best Workplaces in Consulting and Professional Services.


Liberty Advisor Group

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