Valentine's Day Puzzle
All you need is love, but a little project management helps on Valentine's Day.
Getting to the heart of the matter: Project managing the perfect Valentine's Day
Feb 08, 2024, by Stephen Kostrzewa
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Building skyscrapers, launching a billion-dollar marketing campaign, organizing a world tour — all titanic productions. But for many people, they’re still not as daunting as planning for Valentine’s Day. From buying flowers to booking entertainment, there can be a lot to consider, and the stakes are high. After all, who wants to disappoint a loved one on a special occasion?

Fortunately, says Robert Massoud, lecturer of Management at Bryant University, coordinator for the university’s Team and Project Management program, and a past president of the Ocean State chapter of the Project Management Institute, there are some basic, times-tested tactics you can apply to holidays and events that are used by project managers all over the world. And if you follow them, they will put you on the right track toward creating an unforgettable night for you and your partner.

“I like to remind my students, everything we do is a project, and managing those many different types of projects involves a lot of the same principles,” says Massoud, from executing your morning routine to planning a vacation to celebrating a strike from Cupid’s arrow on the most romantic — and, for some of us, the most stressful — day of the year.


Understand your “client” 
The first step in any successful project is making a plan — and making sure it’s what your “client” wants. Don’t just decide what you think a fulfilling Valentine’s Day would be; consider your partner and make sure you understand what they would truly want. What sort of food would make for your partner’s ideal Valentine's Day meal, for instance? How fancy should the restaurant be? Would they prefer the atmosphere to be more lively or more intimate?

“If you truly don’t know the answer, ask the question,” he says. “How can you possibly meet, or exceed, someone’s expectations if you don’t know what they are?”

Plan early and plan well 
Once you have the scope of the project, you can start to think through the game plan. “Anyone can manage a project, but a real project manager can see the entire field,” says Massoud. That means taking stock early of your resources — including time, budget, and distance — so you have the full picture.

From there, do the research. Learn more about local restaurants and flower or candy vendors and, if possible, try them out. It’s also not a sin to ask around to see what others have done, Massoud says. “No two projects are exactly alike,” he notes. “But no project is so unique that you can't look at history and see something like it.”

Be flexible 
Sometimes, Massoud concedes, the original plans for a project might not be feasible. As much as you, or your partner, might have your heart set on something, it might be too expensive, too complex, or even logistically impossible. But that shouldn’t be discouraging; it’s just an opportunity to try a a different route.

While flexibility is key, it’s also vital that you keep true to the spirit of what your romantic “client” wants. It’s about understanding the tradeoffs, Massoud says. “Some alterations are mundane; they're not a big deal. When there are different options, it comes down to: What does the customer want? If it's not what the customer wants, the discussion is a moot point.”

Assess risk 
When it comes to planning a perfect Valentine’s Day, good project managers know that it means keeping your head on a swivel and taking into account every detail: from making sure your travel routes are undisturbed to checking the weather to double-checking that the restaurant isn’t closed due to unforeseen circumstances — and to keep checking so you have an up-to-the-minute understanding of how things could play out. “Good project managers don’t just understand the potential risks; they stay on top of them and actively manage them,” Massoud says.

It also means developing a solid “Plan B” just in case, whether it’s a different route, back-up gift, or even an alternate restaurant. “I’ve never had a project in my 35 years of experience that didn’t have any changes,” Massoud admits. “You need to be ready for that. If you can think of something that could affect the plan, it should be in the plan.”

Keeping a cool head 
Even the best laid plans, and ones that have been risk-managed up to the last minute, can still have unforeseen roadblocks. That, says Massoud, is when true project managers distinguish themselves. “It’s easy to keep calm when things are going smoothly. But it can be more difficult when you start to hit curveballs.”

The worst possible mistake, when confronted with obstacles, is to lose your cool and get flustered — or worse, angry when the bistro loses your reservation or the performance is sold-out. And if unexpected difficulties do come up, make sure you’re upfront about them, Massoud says. “Don’t try to hide anything, because it will come out eventually,” he advises. Better to be honest and straightforward than to exacerbate problems and create hurt feelings later on — or, worst of all, lose your partner's trust.

Lessons learned 
The last step in executing a successful Valentine’s Day, or any project, says Massoud, is planning for the next one. “Once a project is over, we can’t go back in history and change anything, but we can learn from it. And a lesson learned should mean a lesson applied.”

Think about what went well, what didn’t, and what surprises came up along the way. Most importantly, ask your partner and get their feedback — not just general opinions but details. How was the food? The entertainment? Were the flowers up to par? What was their favorite part? Their least favorite? “Honestly, sometimes you need to have a very thick skin,” Massoud admits. “But getting that feedback is an important part of the process.”

Don't overcomplicate 
The last piece, Massoud suggests, is remembering that, when it comes to projects, “good” doesn’t necessarily mean “complicated.” “My wife and I have been married for 43 years,” he notes. “Sometimes our best Valentine’s Days are having dinner together and watching a movie on the couch.”

Often, the best plan is a simple one. 

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