Simplifying Digital Transformation: A Guide for Engineering Managers to Handle Challenges, Lead Teams, and Keep Projects Running Smoothly
Digital transformation can feel like climbing a mountain — especially for large companies. Whether you’re starting from scratch or building on existing systems, the path is filled with complex challenges and risks.
As an Engineering Manager, you’re responsible for navigating these obstacles and finding ways to overcome them. Success in digital transformation comes down to one key thing: anticipating challenges and staying prepared.
In this article, I’ll share the most common challenges I’ve faced during digital transformation and give you practical tips to help you tackle them with confidence. Let’s explore how to make your transformation journey smoother and more successful.
> CRUSHING DEADLINES WITHOUT CRUSHING YOUR TEAM
Tight deadlines are a common challenge in the software industry. While time is indeed money, the pressure intensifies when multiple projects run simultaneously, creating dependencies and strained resources.
While it’s best to address these issues early, complexities can still arise. Take time to re-prioritize, set clear expectations to all involved parties, and agree on a plan. This is essential when managing complex situations. Have in mind that multiple possibilities are available, from shifting people between projects to adjusting scope of certain projects or even extending some of the deadlines. Burnout should never be an option. Nor should sacrificing quality or piling on technical debt. These are temporary fixes, and you’ll pay for them in the long run.
> MANAGING COMPETING PRIORITIES
Each project might have either a single sponsor or multiple ones. Of course, they have interest in their own projects and might not care about other ones, so could easily arrive at the scenario where everything is a priority. If that’s the case, make sure to clearly expose not only to involved stakeholders but also to upper management the following: what the roadmap looks like, where the dependencies and what the blockers are, and the deadlines the team have based on current resources. They will need to make decisions, and clearly define what the priorities are between all of the projects and adjust as needed.
> NOT GETTING LOST IN THE CHAOS: TRACKING IS YOUR LIFELINE
Things need to be tracked, no matter whether you are using any methodology framework. This includes but is not limited to: new requirements, change-requests, sign-offs, deadlines, dependencies, etc. There are several tools that can be used for this purpose, so why not take advantage of them? Yes, it takes some time and requires some effort to keep it updated on a daily basis, but trust me, it is worth it really.
The benefit is extremely useful: it allows anyone to take a look at any moment, check the status of things, the history, the progress, dependencies and make decisions based on that. The information there can be used to support your work anytime, but especially in those not comfortable situations that could happen from time to time where you need to justify some missed deadline or some inconsistency between what was defined and the implementation itself.
On the other hand, the lack of tracking has some side effects related to efficiency. Some common examples of this are having regular meetings to ensure progress and get updates or exchanging endless chains of emails, or even losing information when somebody is no longer in the project or the company, just to mention some of them.
> MASTERING CROSS-TEAM DEPENDENCIES
Even if you are working on a big project or building a product that interacts with some other existing products/features, as long as many teams or parties start getting involved into the same project, it’s inevitable that at some point they will need to interact with each other.
While it seems to be something obvious, these teams must be communicated from the very beginning. Each team should know what they need to deliver, what the timelines are and how that deliverable piece will fit into the desired output of the project.
Given the fact that each team might have their own projects, priorities, timelines, etc, it’s clear that development won’t necessarily occur in parallel. For that reason, it’s super important that involved teams make an agreement on the contract which must reflect their interaction in advance. This means, each team should know:
- what parties they have to interact with
- how to interact with those parties
By doing this, each team will be able to do their own development without worrying about the readiness of other parties’ pieces. Of course the previous is valid only by respecting what was agreed previously, which allows them to mock the missing pieces in the meantime. Any change there should be properly communicated to the rest of the interested parties, so that they can make adjustments as needed. In the end, some integration efforts might be done to test the feature or the product end to end and ensure everything works as expected, but it should be smooth if they did properly the mentioned before.
> ADAPTING WHEN STAKEHOLDERS LEAVE
It happens from time to time that people who were in a position of taking high-level decisions get out of the project, the role or even the company. This usually occurs when objectives or goals are not met or even when the results were not expected ones. In those cases, new people come in, and this could bring a situation where either defined priorities or even the vision for the business change.
My piece of advice here is to establish a new partnership as if you were starting from day zero but taking advantage of all the knowledge you already have about the business, the applications and the ecosystem itself. Show yourself and your team as helpful and resolutive by focusing on the value you can add to the business even if the new direction taken is exactly opposite to the current one.
> MANAGING MULTIPLE TEAMS AND PARTNERS WITHOUT SILOS
As larger a company is, more chances are that it could work with multiple software providers. What is more, it could be the case that all of them might be spread across different teams or working in isolation. The key **under that scenario **is to work closely with all the team leads and make sure that all of them encourage their teams to follow defined practices and standards and avoid having “silos”. Having regular meetings with leads where people can be aware of what’s going on in other teams plus sharing experiences and facilitating tech discussions might be useful for that purpose.
> NAVIGATING RESISTANCE TO CHANGE
Digital Transformation usually comes to break the status quo. In most cases, this involves introducing a completely new way of doing things which can produce that some people could feel frightened about it and refuse to collaborate because of that. Remember, digital transformation isn’t just about upgrading technology. It’s about getting your team on board, every step of the way.
FINAL THOUGHTS
Successfully navigating these challenges requires a proactive approach, strategic planning, and a commitment to fostering an inclusive culture that embraces change. By approaching digital transformation as a collaborative journey rather than a mere technological shift, organizations can pave the way for lasting innovation and growth.
What challenges have you faced during digital transformation? Share your lessons learned!
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