How Millennial Managers Can Lead Older Sales Reps

There’s a lot of conversation about how to work with millennial sales reps who have different ways of learning and value systems than previous generations (including one of our own posts). But what hasn’t been discussed is the mirror opposite – when millennial managers find themselves in the position of leading a team of tenured, older sales reps. It’s an inversion of the expected norm that merits a closer look to see how these unusual dynamics can be successfully handled.

Get to know reps on a personal level.
In a Reddit thread posted by a millennial manager with this very quandary, a former Army officer who transitioned into sales pointed out in a reply that the situation is similar to what young officers go through in their early assignments. The key to both scenarios is getting to know the older subordinates as people, with an emphasis on finding out their goals and motivations.

For managers, they can more easily establish buy-in from their more experienced reps by figuring out and demonstrating how they can help older reps realize their goals and use tools and tactics that work with a given rep’s motivational source. This process validates sales reps as people and eliminates the top-down authoritarian managing style that could backfire in a young leader/older reports environment.

Listen to reps in both one-on-one meetings and team discussions.
Another way of respecting the wide swath of experience that older sales reps bring is to ask them for feedback and strategy suggestions in meetings. Doing so addresses the concern some senior reps have that a young manager might not respect or value their methods and what’s worked for them in the past. As part of this, managers should also give credit to their reps for ideas that came from their reports – not only is promoting someone else’s idea as one’s own unethical, it’s a one-way ticket to losing control and respect of the team.

Maintain accountability on both sides.
Sometimes when young sales managers make mistakes – particularly those that occur as a result of lacking life experience – they’re afraid to admit it because they fear it will make them look incompetent and unable to handle the job. The reality is actually the other way – accepting responsibility for and taking ownership of errors helps establish accountability and can actually improve manager-rep relations – provided it’s clear what the manager will do to either rectify the issue or prevent it from happening again in the future, and that there’s follow-through with those changes.

Conversely, millennial managers might be wary of pointing out problems in the way their older co-workers are doing things. The thinking is that it could create conflict on the team and be a disruption. In fact, not addressing issues is actually a sign of weakness that will undermine the manager’s ability to lead and runs the risk of issues spreading further. Instead, the problem should be respectfully brought up and a collaborative conversation held to find out the source of the issue, followed by coaching or training (as needed) to fix the problem.

Remember you were made manager for a reason.
The crux of many of the tensions an inverted-age team situation ultimately lies with the young manager’s own fears and insecurities, laced with a strong sense of Imposter Syndrome. These feelings are natural. But millennial sales leaders need to remember they were put in the position because senior management believed them ready and able to take the mantle of leadership.

To alleviate these concerns, seek out the advice of senior management when needed. Consume books about sales leadership – there’s plenty of good ones out on the marketplace. Harness those doubts by using them as a pathway to engaging with team members in an empathetic, caring way. Even something as simple as telling yourself, “You got this” can help.

While an unusual situation in the sales world, millennial managers in charge of a veteran sales force does happen. Creating a successful team dynamic will require a delicate balance built on mutual respect and collaboration and flexibility on the part of the manager. It can also be a rich intergenerational experience that proves rewarding for all involved.

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