Let's get this out of the way first: Some rules and regulations exist for a reason.
At my company, we always stress being agile and responsive -- but some areas are better run with some structure. Specifically, our employees' quarterly performance reviews and weekly one-on-one meetings have templated question and response fields that are designed to keep everybody moving forward in a meaningful way. Our "rules" -- those templates -- exist for each employee's benefit, so that's an area we tend not to veer far from.
Additionally, I think it's important to maintain structure when it comes to every employee's advancement for promotion. It's critical that everybody at the company knows exactly what's expected of them in order to advance in the company, and for those requirements to be public and accessible. With full transparency, paths to advancement should be clear to every employee
Finally: No, it's never OK to bend the rules when it comes to employees' compensation - namely, in my company's case, New York state law that differentiates between salaried and paid-hourly employees.
Now, here's where you can feel free to bend the rules.
Strict Paid Time Off Enforcement
Rules pertaining to time off could also be a touchy subject -- but they don't have to be. At my company, Arkadium, I like to take a common-sense approach. Some situations are easier to solve than others: Specifically with bereavement leave, our employees know that they can take as much time away as they reasonably need. If an employee is running low on sick days, but suddenly comes down with a contagious illness, of course they can take a day -- not only for their own well-being, but also for the sake of the rest of the office.
We always stress the importance of living a full life, but also understand that in extreme circumstances, weekend work is sometimes necessary. On the rare occasion that somebody needs to put in work on a Saturday or Sunday, we credit them with a bonus day that they can use at their discretion. To us, it just makes sense.
The Unwritten Ban on Gifting
I think it's always important to foster goodwill with my employees, and let them know that they're appreciated whenever possible. Sometimes, that means not going by the book.
In my personal life, I'm a big believer that a thoughtful gift is always more valuable than a gift card or an envelope with some cash. At work, in above-and-beyond situations, I think it's perfectly acceptable to treat an employee with a small, meaningful something that helps them feel appreciated. For instance, after we recently moved offices, I gave our office manager a pass for a two-hour massage nearby.
Of course, this doesn't mean it's acceptable to gift somebody a pair of earrings instead of giving them their bonus. But as an additive gesture, a small, personal touch can go a long way.
Hiring By the Book
Perhaps the most important area to demonstrate flexibility? Hiring.
Sure, all of our job postings list a desired background and experience. But if you're limiting yourself only to candidates who fulfill all your wishes, you may let a future star slip through the cracks.
Your interview process, if done correctly, will tell you everything you need to know about potential candidates. I've interviewed extremely qualified candidates who, after interviewing, turned out to be poor fits for our office. Conversely, I've brought in candidates who were a bit more junior, or didn't have a wealth of relevant experience, who blew me away in their interviews.
When it's time to make crucial decisions, you'll need to go with your gut. But without flexibility, you run the risk of getting it wrong.