Why implementations fail to deliver value
When the glow of the sales cycle turns into the duldrum of implementation reality.

When a sales cycle for an enterprise software solution concludes, there is a euphoria amongst the business leaders where they can see their vision come to life. Business transformations that are long overdue appear to be within grasp. Soon after, though, when implementations begin the stark reality sets in where tight budget, organizational inflexibility and technical limitations are slowing down any dreams.
What drives those headwinds and how can organizations prepare to be successful?
Start with setting expectations
When executives evaluate project success, they compare it to their expectations. Going into a large enterprise software implementation, the drivers are frequqntly business outcomes (such as cost to operate, time to market, regulatory compliance) or technical changes (retirement of legacy systems, reduction in cost to serve, gaps in security and resilience).
The value of the implementation needs to be documented at every stage and measured regularly. Too many times expectations are unspoken and assumed. This can lead to delay in decision making and confusion about direction and prioritization.
Organizational Reasons
Not many organizations are prepared for a transformational implementation.
Here are a few reasons where things can go wrong on the organizational side:
- Executive versus middle management: While executives desire a revolutionary business transformation, those changes need to be turned operational and implemented. This is where the middle management and the rest of the organization play a critical. They need to embrace the larger vision and make changes along the executives vision. That sometimes could mean having a smaller team or less influence.
- Resistance to change: For any large project, there will be team members that are not willing to adjust. This may not always manifest in open push-back, but often be seen in resistance and non-adoption.
- Insufficient resources: Running an implementation and keeping a business going at the same time will strain the available resource. You want to have the best people on the project making decisions for the future, but the day-to-day needs to be still covered. Cutting short the design or consensus finding processes may result in problems further down the line.
- Lack of change management: While chnages may be clear to the central proejct team, it needs to be communicated and implemented in the whole organization. Without a chnage management plan and team, there are risks of confusing messages/rumors and missed stakeholders.
- Old becomes new: In order to speed up implemention, unexperienced team fall back on a lift and shift appproach where existing processes are transferred to new technology. This can have significant risk since the new technology likely works differently and limits the potential benefits of the new technology.
Technical Reasons
Choosing the right solution and making the best of what was purchased is key to achieving results. Here are a few reasons where things can go wrong on the organizational side:
- Not enough due diligence: Sales team are specializing in sharing an optimistic view of the solution and are trained to diffuse concerns. Unless the project team has validated that key features work as expected, there is a lot of risk in buying software blindly. Reference calls wioith other customers can help eleviate that risk, but only make sense when the requirements are well documented.
- No skilled resources: Even the best software needs to be configured and operated. For that, specialists are needed initially and an internal team should be trained up. This process becomes more risky when there are only a handful skilled experts in the market in the first place.
- Standard vs customized: Many software packages offer the ability to create new custom objects and modify the system behavior to a certain extend. While this may seem enticing, the decision to go down that road involves a commitment to increased budget for implementation and maintenance and continued staffing.
- Industry solutions: Software systems are generalists. They are designed for a large market with the lowest common demoniator. This may not work for specific industry requirements such as health-care, public entities or professional services.
- Integrations: Software solutions need to play nice in an existing system landscape. The number of integrations required is often underestimated and the effort to design and deliver them is usually the main culprit for project delays.
What to do about it
There are a few clear learnings that apply to addression most of the above reasons:
- Set clear expectations: Organizations work best when goals are cleary stated and pursued. These goals can be stretch goals.
- Continuous mindset: In the old world, you had one shot to set things in concrete. With modern Saas solutions there are options to work iteratively. Achieve inital goals early and make successes visible, then invest in structures that allow you to roll out improvements on a regular basis. This takes the pressure of "getting it right once" to a more experimental approach where new settings can be tested and improved.
- Chose the right vendor: Select a vendor that provides features for the immediate need and allows for growth as your needs change and you are ready to take on more.
