I’ve been fortunate to have several opportunities for professional development in the past few years, both within and outside of my workplace. Among the webinars, cohorts, workshops and trainings I’ve pursued, working with a mentor has been the most beneficial.

First, I have to say that I can’t believe mentorships aren’t more common. I know people who have had similarly positive transformative experiences with personal and professional mentors, but it feels like an arrangement that remains massively underutilized on the whole.

The phrase like a boss strikes a chord with me as a young professional seeking to up my game. Who wouldn’t want to take control of their career and work life like a boss? 

But as a father of a toddler, I realize you can’t always act like a boss—sometimes you have to act like a parent. This is certainly the case when you’re caring for a child, but more and more, I’ve found myself applying lessons I’ve learned from my threenager in my work life.

Give to the Max Day is an annual charitable giving event hosted by GiveMN. The event draws attention to the thousands of nonprofit organizations and schools serving communities throughout the state and encourages philanthropic giving. Last year, Give to the Max Day raised over $17 million for Minnesota organizations in 24 hours.

Give to the Max Day has become something of a holiday for me. I race to my inbox early on the morning of Give to the Max Day to tally up donations to my organization the same way I used to race downstairs to see what Santa had brought me. The energetic buzz around my office on Give to the Max Day is infectious—coworkers shout over cube walls when big gifts come in and create complex high five gestures to congratulate one another. It’s the most wonderful time of the year.

For most of my life I’ve considered the act of learning something that happens in a classroom: there is a teacher who has expertise and knowledge, and there are students who do not yet have that knowledge. Students sit quietly, take notes, study, and eventually learn new information and skills.

I admit it: I’m a fan of the When You Work at a Nonprofit Tumblr. I’ve spent a fair amount of time (at work!) poring over hilarious captioned gifs that capture what it means to work for a nonprofit organization: the dizzying highs when you receive a major gift; the soul-crushing lows when you notice a typo in your annual report; the mad rush for new office supplies or leftover snacks from a board meeting…it’s all there. More than once I’ve found myself reacting to posts like this by saying “RIGHT?!” a little too loudly and looking around for someone to high-five in agreement.

But.

It's inevitable. No matter how well you work with your supervisor, there will come a time when you simply do not agree with her or his approach. This can be a tricky situation: do you bite your tongue and go with the flow? Or do you speak up and risk seeming uncooperative or unwilling? I've found that by following a few guidelines you can navigate this territory and strengthen your working relationship with your boss in the process: