My colleague recently provided excellent insight for experienced workers who are now reporting to someone younger than themselves. 

What to do when you’re that boss?

In coaching our Next Leader Now candidates, I recommend four tools that can help build a productive working relationship with more seasoned direct reports.

Start from empathy

As Rob mentioned in his blog post, older workers reporting to younger bosses may be frustrated, embarrassed, or angry to the point that they’re willing to quit. Even in the best case scenario, where both the boss and the employee are on the same page, it’s inevitable that conflict or ego can get in the way.

Our research into generational communication shows that empathy is the best way to start the working relationship off on the right foot.

“I realize, for some employees, reporting to me wasn’t part of their plan,” said one Next Leader Now alum. “I go into the relationship knowing that they might be coming into working with me with some assumptions, and I do my best not to take it personally.”

Stay curious

When looking at the working relationship between the two largest generations in the workforce (Baby Boomers and Gen Y/Millennials), research has uncovered two trends: Baby Boomers often actively avoid working with Millennials, and Gen Y is unsure about how best to approach Baby Boomers. 

The best Gen Y leaders we have seen are in a constant state of learning, particularly from their more-experienced teammates. Their humble approach of asking for ideas, advice, and perspective allows those who have years of knowledge to continue to be the experts.

One Next Leader Now candidate said, “My role is to keep steering the ship. Even though I’ve been around the business my whole life, there is so much I just don’t know. I’m always asking my team for their perspective and have avoided a couple of awful decisions as a result.”

Play the part

Amongst the barriers of being the boss of an older team are the pervasive stereotypes that have stuck to Millennials. Paired with confirmation bias, Gen Y leaders can easily set themselves back with the people they manage, even if it’s unintentional.

We have seen a few habits that can make Millennial-aged managers significantly more effective: put down the phone, have in-person interactions, and mind the language.

One candidate told us, “I have a couple of people who work for me that joke about me being a ‘typical Millennial,’ but I know it comes from a good place.” She continued, “I’m super-conscious of when I’m using my phone around my team and make sure to take the time to have discussions in-person, which have been much more productive than the long email chains I’d find myself in. Now, my age is an asset and something we can talk about instead of something that is a problem.”

Another candidate said, “I have learned that there are a few habits I had that just don’t work as someone leading a bunch of people from different generations. I ask ‘why’ differently now. I’ve tried to drop ‘like.’ And I have realized that a lot of my pop-culture references don’t apply to all of my team.”

Be fair

Being deferential to those on the team with more experience can help Gen Y leaders be more successful. Unfortunately, it’s not all fun-and-games, and performance issues can arise with any generation.

Gen Y leaders can sometimes struggle with holding older employees accountable. Hesitation to do so, however, can impact the entire team. When addressing issues, consider the impact on everyone, and consider fairness across the whole staff.

Discussing their challenges on this front, an alumnus said, “It took a while for me to learn how to give negative feedback to some of my direct reports who were older. It wasn’t until another employee who was a bit younger than me mentioned that I was hesitant that I realized that it was hurting my ability to lead my team. I learned that if I am fair to the whole team, everyone responds better.”

Bottom line

Millennials are managing in an unprecedented workforce situation, with five generations working and more than sixty years between the oldest and youngest workers. Becoming adept at navigating individual challenges and accounting for the diversity of the generations is no longer optional. 

With just a few adjustments, Gen Y leaders can be excellent leaders in this time of workforce turmoil.