I was recently reminded of an incident that took place around 2010 that, upon further reflection, has an important lesson for Millennial leaders. Let me paint the picture so you understand the context.

I was not in a formal management position but was starting to lead more projects with global teams and gain exposure to senior leaders in my area. I was on a project where I was the most junior person on the team so it was a great learning opportunity. The project involved long hours and was ultimately a success. In parallel my wife was applying for residency positions and she got an interview in a town a couple of hours away. I took a day off so that we could stay in town the night before the morning interview. On the way back we stopped at a place that many in southern Ontario may know called The Big Apple. They sell amazing apple pies, which I love, so we picked some up. I also thought it would be a nice gesture to grab a couple of extras for the people I was working with on the project. We passed by my work on the way home so we popped in to drop them off to my teammates and took the opportunity to have my wife meet some of the team.

Boy was that a mistake! That gesture got me labelled as a suck up to many of the senior leaders in my area. When you’re an up and coming leader that’s not a label you want attached to your name. Now, in the grand scheme of things the effects of this situation were minimal but the consequences could have been far worse.

Let’s break this down a bit further. What was the mistake? Naivety. Being the most junior person on the team and the only Millennial, buying something for everyone else could certainly be perceived as sucking up. What I missed was that the act was probably not something those people were used to – it was something not aligned to that group’s work culture – so they looked for and actualized an ulterior motive. Side note: a $6 apple pie would be a pathetic way to try to get ahead in your career so if you do want to bribe your way up go a little bigger!

This also touches on a broader topic which is perception vs. reality. This affects everyone at work and is something I’ll write more about in the future but in this scenario the reality was that while buying myself some nice treats that are hard to come by since you can only get them by driving 1.5hrs out of town I thought of doing something nice for some coworkers. The perception was that I was trying to curry favour via their taste buds.

So what is the lesson here especially for Millennial leaders who are likely working with leaders from other generations? Pay attention to the culture of those around you and ensure you don’t do things that may be perceived very differently than you intended. Two points though:

1. Culture evolves so I’m not advocating merely falling in line since as a leader your role is to drive team culture. Also, as more Millennials take on more significant leadership roles the culture of companies will change so help change it for the better.
2. I’m not saying you shouldn’t ever do nice things for your coworkers. Given you spend so much time with them I believe that building strong personal relationships will lead to a better work experience for all. But be smart about it so that you don’t get yourself in trouble.

Would I do it again given what I know now? Absolutely not. But would I do it in a different team/company environment? Maybe, depends on who and what the culture is. And whether or not they like apple pie.