“I’ve compiled a laundry list with every to do that came to mind, but you guys will probably need to add to it,” Dimitar, our CEO, said.
It was his last day in the office before a major US trip that would last several weeks and we were at the beginning of May. The deadline for GDPR coming into effect was approaching fast and we had barely scratched the surface of our compliance plan. And with some 500,000 users and a lot of information collected over the past 4 years, it was about to get complicated.
(Sidenote: If you don’t know what GDPR is: 1) I envy you; 2) you should; 3) it’s a good thing; 4) these project management learnings will still apply)
Several weeks later, on May 23, we sent out an email to all users notifying them of our updated Privacy Policy – the key milestone in our GDPR journey. We could hardly believe we had managed to wrap this whole thing up on time.
The more surprising thing was how we managed to do it. No stress, no rush, and a great feeling of – dare I say it? – fun. But you might take a person finding GDPR compliance management “fun” for a bit of a psycho, so I’ll keep my mouth shut 🙂
During a follow-up conversation, another colleague asked me how I managed to work on such a complicated project and not feel overwhelmed or stressed out. I think it’s a question that deserves a written answer.
The recipe for a great project
[click_to_tweet tweet=”Research well, split your tasks, nail them one by one, keep a Done list, and don’t forget to have fun. Is this the recipe for a great project? Here are the details:” quote=”Research well, split your tasks, nail them one by one, keep a Done list, and don’t forget to have fun. This is the recipe for a great project.”]
Looking back, I feel like we got a lot of the steps right. These are no panacea, but chances are they can greatly improve your efficiency – and keep you sane!
Do your research
Dealing with GDPR compliance is a tough nut to crack. There are a lot of points that are anyone’s guess and a question of interpretation. So it was paramount to find a source we could rely on. For us, this was Suzan Dibble. It seemed she had most of the answers we were looking for, but the amount of reading needed was astronomical.
So we ventured into the wonderful world of research. My advice here is “Don’t move forward unless you have everything figured out.” By “everything” I obviously don’t mean e-v-e-r-y-t-h-i-n-g. But you should be able to answer a couple of questions:
- What’s the end goal of the project? Why are we doing it and what do we expect as an end result?
- What’s the scope of the project? What needs to get done?
- What’s the relationship between all the moving parts? Are there dependencies, does some task need to happen before another one?
Yeah, you run the risk of spending unnecessary time in research rather than moving to implementation quickly. However, in my experience, you always feel you have stuff figured out before you actually do. Whatever you do, you will surely jump to implementation before you’re truly ready. Just be a bit readier.
Divide and conquer
Me and one of our lead developers, Alexandar, were tasked with bringing that project home. We sat down on a Monday morning and opened up a brand new Trello board. We listed all the tasks we could think of, assigned priorities, and split the work between ourselves.
This was a great first step because it let us see the full picture and get a feeling about the project scope. It cleared out the fear of the unknown. It also helped us see if we had any chance of finishing this whole thing on time – after all, we were working with a very strict deadline.
I’ve noticed that I have a tendency of procrastinating whenever I run into uncertainty. Project scoping eliminates uncertainty. Once we had stuff laid down, I felt much more secure and ready to take on the world.
Run to the next mark
Once you see the big picture, you should promptly forget about it. If your brain is abuzz with the thought of 20 different tasks coming up, your ability to focus decreases significantly. So zoom into the first task. Work on it. Get it done. Move to the next one.
I’d employ the same tactic when I feel like I can’t run my usual 6 km in the morning. I’ll just focus on running to the next mark – finishing up this kilometer, running to the next curve in my route, focusing on the upcoming water break. One by one, each milestone falls and before you know it, your tracker buzzes with a congratulatory message.
Keep a Done list
One great thing about using Trello to manage a project is having a Done list. Moving a card there is an action that celebrates progress. And in some time, you can look back at the list and remind yourself how much you’ve already accomplished.
We’re generally pretty bad at recognizing our own successes. That’s why having something to remind us about them is a great thing.
Split tasks based on personality and skills
This was a project where we could split tasks however we liked it. My strengths lie in research and writing. So I took on the job of preliminary research and writing up documentation – Privacy Policy, data inventory, internal guidelines, emails to users, you name it.
It’s not always possible to split tasks based on personal preferences, but you should at least take them into account. Or even consider them before thinking about company roles. What if your lead dev has a knack for customer acquisition hacks? Why not let him lead a growth meeting and see what comes out of it?
Build your tribe
Obviously, GDPR compliance was a major thing for everyone – and the number of jokes and memes was record high. Just look at this gold:

Every now and then, we’d share a good joke on Slack. It helped to lighten up the mood but it also did something else – it created a true sense of being a team. We were the GDPR tribe and the internal jokes we’d laugh at and no one else would get proved that.
You can’t always get what you want
There are a couple of things I need to point out. These are prerequisites about a project running smoothly, but I know sometimes you’re dealt a crappy hand and you can’t always count on them.
Ocean’s Fifteen
A guest in a podcast I was recently listening to likened a well-working team to a bank heist gang. The key ingredients are the same, she said. It’s a group of professionals, each in their own field, who have established trust and can completely rely on one another.
This is what working at Enhancv feels like. Objectively, the facts were similar to what a lot of friends dealing with GDPR had going on: “higher management dumped it on us.” But the perception was totally different. Since I have full confidence in our team, I didn’t feel like our CEO just handed off the unsexy job to us as subordinates. It felt like peers coming to help a teammate who needed us. And I know that if I come to a point where I can’t handle stuff on my own, my heist gang has got my back. It’s a great feeling and I hope you have the same.
A partner in crime
The second key ingredient for a successful project is who you work with. This was a project with a very lean two-person team. What we could do was split the task and know that the other person will just do their job – on time and to the best of their abilities.
Not having to worry and constantly check on other people is a luxury. I hope you have the same.
Am I just bragging?
Not at all! (Well, yeah, a little – I’m proud of my team!)
I just need to point these things out and be completely honest: I have no idea whatsoever how to have a successful project without a good team. I do recognize that I’m very lucky. I don’t have an answer on how to get through a project with zero stress if you’re working with people who are, well, royal jerks.
Your mileage may vary
I don’t feel like I’ve mastered project management based on this GDPR project – or any of the dozens I’ve led before. Project planning and execution can vary greatly between companies, industries, teams, or even points in time.
But the first step is taking the time to think what worked and trying to replicate the working bits in the future. I’d love to hear any conclusions from your successful projects.



