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The pains of transformation

Dima Svetov
4 min readOct 4, 2023

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In today’s fiercely competitive business landscape, the ability to adapt and evolve is not merely advantageous — it’s imperative. Organizations, in their quest to stay ahead of the curve, must constantly undergo transformative changes. As my boss aptly puts it, “In today’s business world, failing to evolve means inevitable degradation and falling behind.” However, the path to transformation is fraught with challenges that require a dedicated commitment to navigating hurdles and overcoming obstacles.

In this blog, we embark on a journey through the intricate landscape of engineering transformations. In the relentless pursuit of improvement, we often find ourselves entangled in a web of complexities that extend beyond the commonly discussed hurdles of resistance to change, securing buy-in, and maintaining momentum. Here, we delve deeper into the multifaceted challenges that engineering managers face as they endeavor to lead their teams through these transformative processes.

Challenge 1: Establishing Measurable Success Criteria

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Identifying what constitutes success in a transformation can be an arduous task. Often, transformations involve multifaceted changes that span several months or quarters. Defining success becomes even more challenging when you realize that merely tracking tasks completed in a tool like Jira isn’t sufficient. It doesn’t measure the real impact of those tasks.

To overcome this challenge, we advocate breaking down the transformation into smaller, monthly milestones, providing flexibility and room for experimentation. For instance, if your goal is continuous delivery, a monthly milestone could be achieving delivery to a staging environment. This approach allows teams to see tangible progress and stay on the right track throughout the transformation journey.

Challenge 2: Balancing Transformation with Daily Operations

Engineering teams are often inundated with urgent issues, project deadlines, and ongoing maintenance tasks. Keeping the transformation effort alive amidst this chaos is an uphill battle. The key to success here lies in fostering buy-in among engineers by showing them how the transformation directly benefits their daily work.

For instance, if your engineers are bogged down by QA delays, automation can help alleviate this bottleneck. By automating validation tasks, engineers can focus on their core responsibilities, and this tangible improvement links the transformation effort directly to their daily lives.

Challenge 3: Determining Completion in a Continuous Process

The concept of “done” in engineering transformations is paradoxical: it’s never truly finished, yet there are countless moments of completion along the way. Celebrating these minor milestones is crucial for morale and motivation. Acknowledging achievements, whether internal (e.g., increased squad velocity) or external (e.g., higher customer satisfaction), keeps teams motivated and engaged.

Understanding that transformations are ongoing journeys but also recognizing and celebrating the steps taken is vital for maintaining momentum.

Challenge 4: Navigating Stakeholder Reporting

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Reporting progress and results to various stakeholders can be a daunting task. Different stakeholders require different types of information, making it challenging to provide a comprehensive overview. The VP might be interested in gains like velocity and reduced downtimes, while product owners are concerned with how transformations affect roadmaps.

Additionally, some reports may initially show unfavorable results before improvements become evident. To navigate this challenge, it’s crucial to have strong support from senior management. Expectations should be managed, and a mitigation strategy in place for low periods.

One effective approach is to communicate potential setbacks well in advance of reporting deadlines, cushioning the impact and allowing stakeholders to understand the bigger picture.

Challenge 5: Balancing Short-Term vs. Long-Term Goals

Engineering transformations often require a delicate balancing act between short-term and long-term objectives. While it’s crucial to demonstrate quick wins and show immediate benefits to maintain momentum and gain support, it’s equally important to keep the long-term vision in mind.

Short-term goals may involve streamlining specific processes, reducing bottlenecks, or improving team efficiency. Achieving these goals can help build confidence in the transformation efforts.

However, focusing solely on short-term wins may lead to neglecting critical long-term strategic initiatives. These could include fundamental architectural changes, cultural shifts, or upskilling the workforce. Ignoring long-term goals can result in technical debt, stifling innovation, and hinder the sustainability of the transformation.

Successfully navigating this challenge requires a well-defined roadmap that incorporates both short-term and long-term objectives. It’s essential to strike a balance between addressing immediate pain points and strategically positioning the organization for future success. This approach ensures that the transformation is not just a quick fix but a sustainable and evolving journey.

In conclusion, engineering transformations are complex endeavors, but with the right strategy, they can lead to success. Engage all stakeholders, clearly communicate the benefits, and address challenges as they arise. Remember, not every transformation is suitable for every organization, so be open to the possibility of failure. The key to success lies in continuous evaluation, adaptation, and iteration. By doing so, you can foster a more efficient and effective engineering department, ready to meet the ever-evolving demands of the business world.

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