Jobs › MyPath

Lead Caregiver

MyPath · Brookfield, WI · $17.00–$19.00 an hour

Posted Sep 16, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

As a Direct Support Supervisor you will train and coach caregivers in the home. Tell me about a time you helped someone get better at their job.

What they are checking: Whether they can coach peers patiently and know what good care looks like.

How do you move from being a coworker to being someone's supervisor?

What they are checking: Whether they can set expectations with people they used to work alongside.

What would you do

A staff member tells you a coworker was rough with a client. What do you do?

What they are checking: Whether they know to report allegations of abuse to management immediately and not investigate alone.

You are on call and a caregiver calls to say they will not make their shift in an hour. What do you do?

What they are checking: Whether they can solve coverage problems quickly without leaving clients unsafe.

How do you prepare meals that follow a client's dietary guidelines when the client wants something else?

What they are checking: Whether they can respect client choice while following health requirements in the care plan.

About the work

How do you build a work schedule that keeps the home covered and is fair to staff?

What they are checking: Whether they can balance coverage needs with staff fairness, which affects morale and turnover.

This role includes managing client funds. How would you keep those records accurate and protected?

What they are checking: Whether they understand that client money must be tracked carefully and openly to prevent misuse.

Walk me through how you give medications safely and what you do if you notice an error.

What they are checking: Whether they follow medication procedures strictly and report errors right away instead of hiding them.

How do you keep guardians and case workers informed without sharing more than you should?

What they are checking: Whether they communicate well while protecting client confidentiality.

What changes in a client's health would make you call a nurse or doctor right away?

What they are checking: Whether they watch for warning signs and act on them, a key part of health monitoring.

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The full job description

As published by MyPath.

Majority Women Employee-Owned. Empowered by Everyone to Transform Lives. Overview HIL is looking for a Direct Support Supervisor (DSS) to join our team. A DSS will be responsible for supervising caregiver staff in the home, training, coaching and mentoring your team. Provide supervision of personnel and client care, enhancing the overall health, safety, and welfare of the clients and programming. As a Direct Support Supervisor , you will : • Maintain work schedules, training of staff, implementation of company policies and procedures • Management of client funds • Maintain excellent communication with guardians/case workers/management and overall health monitoring of clients • Report allegations of abuse, resident rights violations, conflict of interest, harassment, or fraud to management. • Maintain professionalism and confidentiality. • Health monitoring and medication administration • Meal preparation in accordance to dietary guidelines • On Call Responsibilities Benefits: • Wage based on experience: $17.00-$19.00 • Referral Bonus Program - $2,000 Bonus per positive referral • Health, Dental, Vision, 401k, Life Insurance, Paid Time off, Company Stock • Access up to 50% of your earned money before pay day comes • Tuition Reimbursement and Loan Pay-down Programs Qualifications • Minimum of 18 years of age • Reliable transportation to and from programs and training classes • Communication & Problem-Solving skills • 1-2 years of previous supervisory experience preferred • Ability to work with individuals with special needs or willingness to learn • Managing stressful conditions by maintaining self-composure and self-control • Successful completion of a caregiver background check, TB test and Health Screen • Valid Driver’s License with 3 years of acceptable driving record, required • Ability to read, write, and speak English fluently Additional Information MyPath and its Operating Companies provide specialized services and dignified care for children, adolescents and adults with special needs. Our companies provide a spectrum of services and support which promote the ability of those we serve to live as independently as possible in the community. MyPath is composed of a beautifully diverse spectrum of employees with different characteristics, abilities, and life experiences. We believe that equitable, diverse, and inclusive practices in our workspaces are integral to the existence of MyPath. We value our diverse spectrum of Owners, the individuals we serve and the communities we encounter. Our success as an organization is directly proportional to our ability to create belonging and genuinely engage our Owners and potential Owners. We ask for demographic information so that we can be intentional in supporting our Owners best. Although not required, we would appreciate you sharing to help our commitment of cultivating a diverse, equitable, inclusive, and belonging MyPath. Our Culture At MyPath, we support an ownership culture throughout the organization. Our culture is based on our five beliefs and behaviors: • Passion • Accountability • Teamwork • Openness • Continuous Learning and Innovation As an employee owner, you can expect transparency, respect and appreciation. You’ll impact the place you work and map a career within MyPath. With your passion and our breadth of services, your options are nearly limitless! MyPath is proudly Majority Women Employee-Owned, with women leading at every level from the frontline to the boardroom. Our strength comes from all of us. Every Owner, regardless of gender, plays a vital role in shaping our culture, driving our mission, and building a workplace where opportunity and ownership are shared by all. MyPath is an Equal Opportunity Employer (EOE) committed to fostering a diverse, equitable, and inclusive workplace. We embrace the unique characteristics, abilities, and life experiences of our employees and believe that equitable and inclusive practices are essential to our success. We value the diversity of our Owners, the individuals we serve, and the communities we engage with.

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