When I joined Airbnb in early 2013 as the Head of Global Hospitality and Strategy, CEO and co-founder Brian Chesky also asked me to be his in-house mentor (and I’ve continued in that mentor role even after I left a full-time position with the company in 2017). My boss was my mentee. In reality, we were both “menterns,” simultaneous mentors and interns.
Brian often asked me for leadership advice and sometimes looked for my guidance in providing performance reviews for his direct reports. You can imagine how awkward it was when Brian gave me my first review a few months into the job. Generally, it was a positive review with some fair feedback.
After listening to him for fifteen minutes and reviewing some of his written comments before our time together, he asked me, “So, what do you think?” I responded, “Well, do you want my feedback as your mentor or as your direct report?” We both chuckled and realized this unusual conversation might become more common in the future as Millennials review Boomers in the workplace.
Here are my three tips for creating a collaborative relationship with your younger boss (especially when they’re a decade or two younger):
- Try developing a “mutual mentorship” relationship such that you’re open to learning from each other. Brian taught me DQ (digital intelligence), and I taught him EQ (emotional intelligence) and we were both better off for it. This requires humility from both parties.
- Intern publicly and mentor privately. If you need to give your boss some wise feedback that’s meant to help them be a better leader, do it privately and in a way that doesn’t make them defensive. That means empathizing with what they’re going through, sharing a time when you were going through something similar, and outlining what you learned. Find common ground whenever you can, and don’t talk down to your boss.
- Take cues from your young boss concerning how they like to communicate. One of the biggest differences between younger and older workers is what mediums they prefer for conversing. If he or she likes Slack, it’s time for you to like Slack. Younger people prefer faster, more direct conversations, which means their text can feel a little clipped or curt. Don’t take it personally. Once again, you have something to learn from each other.