Supervisor Dilemma Cards

Forty realistic judgment calls that new supervisors face, as printable discussion and role-play cards, with a facilitator debrief guide that gives the points to consider and the trade-offs for every card, not one right answer.

Who it is for

• Trainers and L&D teams running new supervisor or first-time leader programs

• Managers coaching a newly promoted shift lead, team lead or crew lead

• Small-business owners promoting their first supervisor

• HR staff who want supervisors to practice decisions before they make them for real

• New supervisors working through the cards with a peer or mentor

The problem it solves

The hardest part of a first supervisor role is not the tasks. It is the decisions no policy fully answers: a friend who now reports to you, a top performer who skips the rules, a manager who asks for something that feels wrong, an employee who seems to be struggling. New supervisors usually meet these alone, for the first time, in the moment. These cards let a group practice them first. Each card is a short, realistic situation with more than one reasonable answer. The group discusses, decides and plans the first conversation, then the facilitator uses the debrief guide to widen the discussion with points to consider, possible approaches and the trade-offs of each.

What is inside

• Copyright, how to use the pack and terms explained (3 pages)

• Guide (5 pages): what dilemma cards are for, five questions for any judgment call, when to ask for help, four ways to run the cards in person and online, how to debrief without one right answer, a four-session program and how to adapt the cards to your workplace

• Dilemma chooser (1 page): all 40 by theme and setting

• 40 dilemma cards (10 pages, four per page): situation, roles with a role-play option, the goal of the practice and discussion questions, ready to cut apart

• Facilitator debrief guide (10 pages): points to consider, possible approaches and their trade-offs, a way to open the conversation, and what to check first where rules apply

• Discussion worksheet (2 pages): blank and filled in

• Dilemma card template (2 pages): blank and filled in

• Editable Word file (46 pages): every card with its debrief notes, plus the worksheet and template

How to use it

1. Read the five questions and choose three or four cards from different themes.

2. Print the cards for groups and keep the debrief pages for the facilitator.

3. Groups discuss, decide and write the first sentence of the conversation, then role-play it if time allows.

4. Debrief with the guide: widen the discussion, name the trade-offs and close with practice.

Formats and file types

• PDF guide, cards and debrief guide, 33 pages, US Letter, print or screen

• Word (.docx), all 40 cards and debrief notes, editable

• Licensed for internal use by the purchasing organization

Frequently asked questions