For many young people in Boston and around New England, summer brings a first real job. It might be scooping ice cream, staffing a day camp, working at a grocery store, helping at a community garden or doing office tasks. A first job teaches lessons no classroom can: showing up on time, handling a tough customer, asking for help and managing a paycheck.
It also brings new stress. A teen may feel nervous, confused about expectations or unsure how to handle a problem with a supervisor. A trusted adult who checks in regularly can make a big difference. That adult might be a parent, an aunt or uncle, a neighbor, a coach, a faith community member or a family friend.
This guide offers a simple structure for weekly check-ins and practical topics to cover.
The Mentor’s Role
A mentor is not a manager or a fixer. The goal is to listen, encourage and help a young person think through situations on their own.
Good mentors:
- Ask open-ended questions and listen more than they talk.
- Celebrate small wins.
- Share their own early job experiences, including mistakes.
- Help the teen find solutions rather than stepping in to solve problems.
- Keep conversations private unless there is a safety concern.
Setting Up Check-Ins
Consistency matters more than length. A fifteen-minute conversation each week is plenty.
- Pick a regular time, such as Sunday afternoon or after the teen’s last shift of the week.
- Choose a relaxed setting: a walk, a coffee, a porch chat or even a phone call.
- Keep it casual. This should feel like a conversation, not an interview.
- End each check-in with one small goal for the coming week.
Week One: Settling In
The first week is often overwhelming. Good questions:
- What surprised you most?
- Who are the people you work with, and who seems helpful?
- Is there anything you are still unsure about, such as breaks, uniforms or schedules?
- How are you getting to and from work?
Help them think through practical details like transportation backups, what to pack for lunch and how to set reminders for shifts.
Week Two: Communication
Many first-job challenges come down to communication.
- How do you let your supervisor know if you will be late or sick?
- Have you had to ask for help? How did it go?
- Is there anyone who is hard to work with?
Practice a few scripts together. For example: “I want to make sure I am doing this right. Could you show me one more time?” or “I am running about ten minutes late because the bus is delayed. I am on my way.”
Week Three: Money
The first paycheck is exciting and sometimes confusing.
- Look at the pay stub together and talk about deductions in general terms.
- Discuss a simple plan: some for spending, some for saving, some for goals.
- If the teen does not have a bank account, talk about options and what they would need to open one.
Keep the conversation supportive. The goal is understanding, not control.
Week Four: Rights and Safety
Young workers should know that they have rights and that it is okay to speak up. Massachusetts has specific rules for workers under 18, including work permits and limits on hours and certain tasks. School counselors and the state’s official labor resources can explain the current rules.
Questions to ask:
- Do you feel safe at work?
- Are you getting your breaks?
- Has anyone asked you to do something that felt wrong or unsafe?
If something sounds concerning, help the teen figure out who to talk to, such as a supervisor, a program coordinator or a trusted adult who can help them find official guidance.
Mid-Summer: Skills and Strengths
By July, teens often settle in. This is a great time to reflect.
- What are you getting better at?
- What do you enjoy most? Least?
- Is there a skill you want to learn before the summer ends?
Encourage them to ask for feedback from their supervisor. It is a powerful habit to build early.
End of Summer: Wrapping Up Well
How a job ends matters as much as how it starts.
- Encourage the teen to give notice if they are leaving before school starts.
- Suggest they thank their supervisor in person or with a short note.
- Help them write down what they did, so they can add it to a resume.
- Talk about whether to ask for a reference.
Finding a Teen to Support
You do not need a formal program to mentor. Many teens already have adults in their lives who could step into this role with a little intention. Let a young relative, a neighbor’s kid or a member of your faith community know that you would be glad to hear how the job is going. Youth employment programs, schools and community centers sometimes look for volunteer mentors as well, and they usually provide training and background checks. If you join a structured program, follow its guidelines about communication and meeting places, which are there to protect everyone.
Signs a Teen Needs Extra Support
Watch for signs of stress that go beyond normal nerves, such as trouble sleeping, dread before every shift or worries about safety. Listen without judgment and help them reach out to the right people. A good mentor does not have all the answers but knows how to help find them.
Why It Matters
A first job can shape how young people see themselves as workers and as members of their community. When a caring adult is in their corner, they are more likely to stick with challenges, speak up for themselves and carry those lessons into the next opportunity.
You do not need to be an expert. You just need to show up each week and listen.
Quick check: What is the main role of a first-job mentor?
- To call the teen’s boss whenever there is a problem
- To listen, encourage and help the teen think through solutions
- To manage the teen’s paycheck
Show answer
B. Mentors support and guide; they help teens build their own confidence and problem-solving skills.
