For Managers

Onboarding
& Best Practices

Creating caring workplaces · a field guide for supervisors

A short, practical handbook for noticing when someone on your team needs support — and responding in a way that helps. Most of it takes seconds to use; keep it close.

Lollipop Software · Culture Software Solutions, Inc.
Onboarding & Best Practices
For Managers

Contents

A short, practical handbook for noticing when someone on your team needs support — and responding in a way that helps. Most of it takes seconds to use; keep it close.

1What Lollipop isp.3
2How it worksp.3
3Your role as a managerp.3
4Introducing Lollipop to your teamp.4
5Responding to an alert: connect, don't fixp.4
6Examples of supportp.5
7Keeping engagement highp.5
8Confidentiality & when to escalatep.5
9Your tools — and how to use themp.6

Companion materials — open or print

→Team introduction script — read-aloud for your team meeting§4
→Sample employee introduction email — English & Spanish§4
→Desk references — Active Listening · Body Language · Communication Pitfalls§5
Lollipop · Creating Caring Workplaces
Onboarding & Best Practices
For Managers
1

What Lollipop is

Lollipop gives you a real-time read on how your team is feeling — and simple, practical ways to connect with anyone having a hard time. Two ideas sit at its heart: people need to be heard, seen, and understood; and small, authentic gestures from a manager have a big impact.

2

How it works

1 · Check-inTeam members get a quick text or email asking how they're feeling — a 1–5 mood, optional emotions, and an optional comment, in a few clicks.
2 · AlertA low score or a comment sends you an instant alert, often with a simple suggestion for how to connect.
3 · ConnectYou reach out and offer support. Often a brief, genuine check-in is all it takes.
3

Your role as a manager

Lollipop works because of you. Four simple habits make all the difference:

  • Encourage your team to check in — and explain the company uses Lollipop because it cares.
  • Respond to alerts promptly and reach out with genuine care.
  • Talk about Lollipop regularly — in team meetings and one-on-ones.
  • Lead by example and participate yourself.

Encourage participation — but never require it. Some will use it only when they need it; simply knowing it's there makes a difference.

Lollipop · Creating Caring Workplaces3
Onboarding & Best Practices
For Managers
4

Introducing Lollipop to your team

How you introduce it sets the tone. Where possible, do it in person at a team meeting and cover four things:

  • Why — check-ins so everyone feels seen and supported.
  • How — a quick text or email; a low response alerts you to reach out.
  • Confidential — private; shared only with you and HR.
  • Optional — never required, but if shared, it's seen and it matters.
Tasked with notifying employees yourself? We've written these for you — open, edit, and send:

Team Introduction Script

Read-aloud · Open

Employee Intro Email

EN/ES · Open
5

Responding to an alert: connect, don't fix

Your goal is to connect, listen, and understand — not to diagnose or solve. Be a bridge to the right help, not the help itself.

  • Approach — caring mindset, somewhere private, ask if they'd like to talk.
  • Listen (80/20) — let them talk ~80% of the time; don't interrupt, ask clarifying questions, restate what you heard.
  • Engage — show genuine concern; if work-related, offer a next step; if personal, ask how you can help.

What not to do

Don't minimize (“that's not so bad”), judge (“why didn't you tell me sooner?”), diagnose, or make it about you. Sometimes the best thing to say is “thanks for trusting me with this.”

Printable desk references — open, print, and keep them by your desk:

Active Listening

Open

Body Language

Open

Communication Pitfalls

Open
Lollipop · Creating Caring Workplaces4
Onboarding & Best Practices
For Managers
6

Examples of support

Match support to what someone is experiencing — and celebrate good moments, not just hard ones.

Family emergency or lossRemind them of leave policy; send flowers; have leadership make a personal call.
Transportation or childcareOffer temporary ride-sharing, a schedule change, or work-from-home.
Health, overwhelm, or anxietyPoint to sick-leave, disability options, or the EAP; offer extra breaks or an afternoon off.
A win or milestoneAcknowledge them in a meeting, a handwritten note, or lunch.
7

Keeping engagement high

Adoption takes months; consistency turns checking in into a habit. Mention it regularly, respond to alerts quickly, celebrate improvements (when someone's mood lifts, ask what helped), and lean on your resources — leave policies and the EAP are powerful and often underused.

8

Confidentiality & when to escalate

Keep responses and conversations private — never used for discipline, evaluations, or promotions, and never ask about medical conditions or therapy.

When you must escalate

Immediately notify HR or the General Manager, per company protocols, if a team member shows signs of harming themselves or others (ask directly), or reports harassment, discrimination, or injury.

Lollipop · Creating Caring Workplaces5
Onboarding & Best Practices
For Managers
9

Your tools — and how to use them

Your Manager Resource Library is reachable right from an alert. Tap a name to open it.

Quick Insights

One-minute actions

Research-backed micro-behaviors great managers use to build trust. Pick one to try today.

Open

Conversation Starters

Open the conversation

Ready-to-use questions to connect after a check-in. Filter by an emotion or a situation.

Open

Small Authentic Gestures

Show you noticed

Simple acts of care that help people feel seen. Choose a kind of care, then copy a gesture (no- / low-cost filter built in).

Open

Meeting Icebreakers

Warm up the room

Short, safe questions for teams of 4–10. Hit Random 1 or Give Me 3; keep answers to 30–60 seconds.

Open

Also: Connection Exercises (trust-building activities), Articles & Guides (deeper reading), and the AI CareBot (describe a situation, get thoughtful next steps). Technical issue? Email support@trylollipop.com.

In a nutshell

  • People need to be heard, seen, and understood — small authentic gestures have a big impact.
  • Encourage check-ins, respond promptly, and lead by example.
  • When you connect: listen more than you speak; don't try to fix or diagnose.
  • Keep everything confidential — except a risk of harm, which goes to HR immediately.
Lollipop · Creating Caring Workplaces6