Artem Zaitsev
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Why Most Tech Projects Fail Before They Even Begin

Published January 26, 20264 min min read
Digital transformation project timeline showing failed milestones and frustrated team members analyzing charts and data

Introduction

Over the years of my career, I have observed numerous digital transformation projects which appeared to be a success and which turned out to be very expensive failures. Time and again I have been brought in to rescue projects that were 12-18 months old and considerable time and resources had been invested either by internal teams or external vendors. When organizations request assistance, all their budgets are used up, the morale of the teams is at the lowest level, and the level of frustration among the leadership is high. Although the initial objectives might have been well-defined the actual results are way below the expectations.

The disturbing fact is that this pattern must have been evident since the inception of these projects, even before any code was written or systems installed.

Where Did Things Go Wrong?

Having undertaken several project appraisals, a certain trend comes out. It is not the failure because of poor technology, poor talent, and poor commitment of money. When challenges occur organizations can usually be seen to make authentic strides to take an off-course correction. But the root of the problem is way deeper - such projects were inherently flawed even prior to the actual development. The red flags are exceptionally similar across failed projects:

  • Development cycles with no value present
  • Solutions that can work technically, but not be adopted by users
  • Hidden costs of opportunity that are never reflected on the financial statements
  • Repeat work cycles that demoralize and crush morale

Discovery Is Not a Checkbox Exercise

The underlying cause of these failures has always been a single shortcoming: discovery is being taken as a checkbox - a procedure instead of a strategy. Organizations tend to take discovery as a shallow "getting to know you" or simple requirements-gathering activity, lacking its real point as a crucial step in defining core issues, defining success criteria and aligning both the business and technical teams to a common goal. This ill-founded strategy turns what would be strategic alignment into a mere wish list - a list of outputs instead of outcomes.

Did you know? The difference between carrying a qualified leadership in the course of discovery is difficult to overemphasize. To be successful, one needs the right people and advocates in the room to lead them under the leadership of a person with strong domain knowledge and process experience.

Purposeful Discovery - Four Principles to Project Success

This may be an internal expert or external collaborator who is able to guide the process to the right direction. Organizations that are in need of guidance are bound to fall into the dangerous checkbox trap without proper guidance. To succeed in discovery, one needs a structured approach that is both enterprise level rigor and practical at the same time. The most effective transformations are those that have undergone a four-step process which considers all the important issues of the project foundation:

Business Context and Strategic Alignment

  • Interview stakeholders in technology, operations and business functions to understand core objective, pain points, and desired results
  • Build mutual comprehension of strategic drivers, whether customer experience improvement, operational efficiency or global scaleability preparation
  • Translate the drivers into themes and delivery criteria to be prioritized and managed proactively

Technical Landscape Mapping and Risk Identification

  • Conduct detailed analysis of the current systems and architectural constraints
  • Map integration points and technical dependencies
  • Identify potential risks and mitigation strategies

Requirement Discovery and High-Level Estimation

  • Scope and elicit business needs, user journeys, epics, functional requirements using agile backlog grooming techniques and proven templates with real-life examples
  • Facilitate structured workshops
  • Understand where custom Agile practices are required to fit within internal bandwidth, regional engagement, and stakeholder structure

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Final Thoughts

Before launching any new transformation initiative or reviewing projects underway, organizations must be honest about:

  • Is the delivery team aware of why this work is important, as opposed to what to build?
  • Have you designed discovery in a manner that empowers delivery and not procrastinates it?

Discovery is not only a more important stage of a project, it is the essential base where clarity is reached, teams coordinate their actions, and strategic decisions are made based on the tangible data and knowledge. It grounds the whole project on initial foundation goals and balances the personal desires with the real and attainable results. Companies that fail to perform discovery properly risk wasting both time and money as well as organizational trust, not to mention the high chances of project failure.

Pro tip: The pitfall that is the most common is misaligned objectives between business and technical teams. Discovery exercises turn into feature wish list exercises instead of strategy alignment. The teams will be fast, but they are running on the wrong path altogether.

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