Starting a second career takes a lot. You need to decide whether or not to make the switch, and you must learn how to retarget your skills if you do.

This phenomenon has two sides to the picture, though. Not only may you need guidance and wisdom entering a second career, but you’ll need the same help if you’re working with or above someone in this position. What is it like to work with someone in their second career? Better yet, how can you be a good boss to these employees?

You obviously saw something in them when you first met them. Something about their experience, character, or personality struck you enough to give them a job. However, there is no denying that working with this kind of employee can be a slightly challenging task.

Here are three commons barriers you might run into when working with these employees and what you can do to build a bridge.


We’ve said it before and we will say it again: It is never too early or too late to change careers. Because of this reason, it is not uncommon for you to manage people who are older than you—especially second-career employees.

If you’re managing workers that have five, 10, even 15 years on you, then you may think that you cannot relate to them at all. Maybe they have spouses, families, and have gone through stages of life that you aren’t nearly close to at all. But don’t make the mistake of thinking you can’t relate to them outside of the workplace.

Just because you aren’t married or haven’t seen your first grandchild yet doesn’t mean you can’t take an interest in older employees’ lives. You might not be able to offer advice, but you can still ask about their families or career aspirations. You’ll probably find more similarities than you think.

Younger bosses may also feel uncomfortable correcting older employees. An awkward dynamic may form if your older employees feel disrespected by your assistance. The best way to handle this is to be confident and treat each employee as equal, regardless of age. If you do feel uncomfortable working with your older employees, asking for feedback is a great way to combat this. Your employees will tell you if they feel like the age difference is preventing either of you from doing a good job. Talking it out will help alleviate stress and will allow both parties to succeed in their roles.

On the other hand, you may be thinking that because your employees are older than you, they do not respect you. Do not let that get to your head. If these employees are good workers, they will respect you because of your title and leadership style, without regard to age. Don’t be intimidated by the years that surround you.


While second-career employees may not have as much experience as you in your respective field, they still have professional experience nonetheless. You are the boss for a reason, but being the boss doesn’t mean you have to be closed off to learning something new.

When you find yourself in a difficult situation at work—perhaps a computer program won’t run or people aren’t respecting deadlines—you should turn to second-career employees for advice. Chances are, they experienced something similar in their old industry and could offer some advice. Their specific experience may not be relevant to the issue at hand, but how they troubleshooted and handled certain situations is relevant.

Understand that you can learn as much from them as they can from you!


There are two things you could be thinking of in terms of training: 1. Second-career employees need a lot more training than your typical employee, or 2. They need no training at all. When second-career employees come to work for the first time, leave both assumptions at the door!

While these employees have years of experience under their belts, they may not know the specific ins and outs of your company. From internal softwares to meeting practices, these things may be foreign to second-career employees. It is important that you teach them the tools to be successful in their new positions.

However, as you are teaching these employees all there is to know about your department or company, pay particular attention to their learning style. If you see that they are picking up the information quickly, then don’t hover over their training. But, some employees may take longer than others to get used to everything. Everyone learns at their own pace, regardless of age or experience. Get to know your employees individually so you can help them excel in their new positions.

When you first start working with second-career employees, leave all your myths and assumptions behind. Remember that there are things to learn for both parties involved.

Need some more help connecting with new employees? Give iGenCo a call today and take the first step towards build stronger, healthier relationships within your business!

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