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ResourceHalf-day instructor-led workshop · (Virtual) Instructor-Led Training

Difficult Conversations for New Supervisors

A half-day workshop that gives first-time supervisors a repeatable structure for the conversations they most want to avoid.

Notes for reviewers
  • This entry is a DEMO — every field is filled so the whole page shape is visible.
  • The linked PDF is a stand-in, not this workshop's real deck.
Training time
3.5 hours
Role
Designer / facilitator
Languages
English, Spanish
Built in
Canva, Google Slides
Skills
  • Facilitation
  • Scenario design
  • Rubric writing
  • Rapid prototyping
  • Bilingual delivery
AAnalyze

Problem

Newly promoted supervisors were avoiding performance conversations until the problem was large enough to require HR. Exit interviews named "my manager never told me" as a leaving reason four times in one quarter.

Audience

Twenty-two supervisors promoted from individual contributor roles within the last eighteen months. Most had no management training of any kind. Roughly a third work primarily in Spanish.

Analysis

Six interviews and a review of one quarter of exit data. The gap was not willingness — it was that nobody had given them a structure, so every conversation had to be invented from scratch under pressure.

Findings

Show findings3
Finding #1
Supervisors avoid the conversation because they lack a structure, not because they lack nerve.
  • "I rehearse it in the car and then talk about the weather."
  • 5 of 6 interviewees described a conversation they had put off for more than a month.
Finding #2
Written notes were the single strongest predictor of whether a conversation actually happened.
  • Supervisors who kept notes held 3x as many check-ins.
  • "If it's written down I can't pretend I forgot."
Finding #3
Spanish-speaking supervisors were twice as likely to defer the conversation to someone else.
  • "The words matter too much to get them wrong."
  • Every Spanish-first interviewee asked for a script.
DDesign

User stories

  • As a new supervisor, I want a four-step structure I can remember under pressure, so that I start the conversation instead of rehearsing it.
  • As a Spanish-first supervisor, I want the same phrasing in both languages, so that I am not choosing between accuracy and speed.
  • As an HR partner, I want a shared vocabulary, so that escalations arrive already framed.

Solution

A half-day workshop built around one four-step structure, practised three times on escalating scenarios. Participants leave with a pocket card and a filled-in template from their own real caseload.

Learning objectives

  • Name the four steps of the structure without prompting.
  • Open a performance conversation using a neutral observation rather than a judgement.
  • Write a follow-up note that states one behaviour, one impact and one next step.
  • Deliver the same conversation in Spanish using the provided phrasing.

Visual style

Colors
Headings
#152238
Body
#3A3F4A
Primary Accent
#0F766E
Secondary Accent
#F4C95D
Warning
#B3261E
Typography
Header
Aa
H1
34px
Source Serif 4 Semibold
Body
Aa
P
16px
Inter Regular
Pocket card
Aa
P
13px
Inter Semibold
DDevelop

Storyboards

AI use

AI generated the first draft of the twelve practice scenarios, which were then rewritten against real (anonymised) cases — the generated versions were plausible but conflict-free, and the whole point is the conflict. No AI in the assessment rubric.

Full resource

IImplement

Implementation #1

Mar 2 2026

1 of 2

Audience or pilot group
Cohort 1 — 11 supervisors, distribution centre
Facilitator(s) / instructor(s)
Kyle Matthews
Delivery method
Instructor-led (ILT)
Versions deliveredFull resource v1·Facilitator guide v1·Pocket card v1.1

Readiness

Technical issues encountered

The room projector would not take HDMI, so the deck ran from a borrowed laptop. Twenty minutes lost at the start; the Frame segment was cut to 15 minutes to recover.

Issues by priority

PriorityIssueRecommendation
MajorScenario cards 7–12 were never printed.Ran round three from the screen; added the print run to the checklist.
MinorPocket card text was too small to read at arm's length.Reset at 13pt for cohort 2.
CriticalTwo participants had no Spanish materials despite requesting them.Language preference is now collected at registration, not on the day.
NormalSession ran nine minutes long.No change — the overrun was the closing round, which is worth the time.

Learner support resources

Help desk
HR partner on call for two weeks after each cohort.
Office hours
Thirty minutes, Thursdays, for four weeks.

Lessons learned

Print everything the day before, not the morning of. The Spanish materials failure was a registration problem wearing a logistics costume.

EEvaluate

Evaluation #1

Data sources

  • End-of-session survey
  • 90-day manager check-in
  • HR escalation counts
  • Observation rubric

Results

Completed the workshop
22 of 22
Named all four steps unprompted at 90 days
18 of 22
Held a documented conversation within 30 days
76%
HR escalations, quarter over quarter
−41%
Mean confidence, before → after
2.4 → 4.1

What people said

"I used it the next morning. It was still awkward, but it happened."

"The pocket card is in my badge holder. That is the whole reason I remember it."

"I finally had words for the thing I'd been avoiding for six months."

  • The structure mattered more than the content.

  • Practice with a real case beat practice with a written one.

  • Spanish-first supervisors used the scripts verbatim and said so without embarrassment.

Facilitator observations

  • Round three is where the learning happens; rounds one and two are warm-up.

  • Nobody used the rubric on themselves without being asked to.

Against the success criteria

Partially

  • 80% name all four steps at 90 days.

  • Documented conversations up by half.

  • No participant reports being unable to work in their stronger language.

Two of three met. Recall landed at 82% and documented conversations rose. The language criterion failed in cohort 1 and passed in cohort 2, so it is counted as not met for the round as a whole.

Recommendations

  • Collect language preference at registration and print from that list.

  • Cut rounds one and two to one round and give the time to round three.

  • Send the pocket card as a phone wallpaper as well as a card.

Revisions made after evaluation

  • Pocket card reset at 13pt.

  • Extension prompt added to all twelve scenario cards.

  • Registration form now asks for materials language.

Reflection & next steps

Run cohort 3 with the single-round structure and compare recall at 90 days.
Build the Spanish observation rubric, which is still English-only.