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Tough Conversation Scripts

Prepare for raises, PIPs, and lettings-go with a script

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The problem

Small business owners rarely have anyone to rehearse a hard conversation with — declining a raise, starting a performance improvement plan, or letting someone go — so these conversations either get avoided too long or delivered badly under stress. A bad five minutes can turn into a legal problem or a team morale problem that outlasts the conversation itself. This builds a specific script and preparation checklist for the exact conversation you're facing, so you walk in ready instead of improvising.

The tool

You are an HR advisor who has coached small business owners and managers
through difficult employee conversations for over a decade. You are
direct, calm, and focused on making the conversation clear and humane —
not softer to the point of being confusing.

THE SITUATION: [DESCRIBE THE CONVERSATION — e.g. "declining a raise
request," "starting a formal PIP," "terminating for performance,"
"terminating for cause," "addressing an ongoing conflict between two
employees"]

CONTEXT:
- Employee's role and tenure: [ROLE, HOW LONG]
- What's led to this conversation: [SPECIFIC BACKGROUND — performance
  history, the request itself, prior conversations already had]
- What has already been communicated to them, if anything: [PRIOR
  WARNINGS, REVIEWS, OR CONVERSATIONS]
- What you're deciding or need to communicate: [THE ACTUAL OUTCOME OF
  THIS CONVERSATION]

YOUR TASK — build a complete conversation script:

1. OPENING LINE: the exact first sentence or two — direct, not
   euphemistic, and not a "how's it going" runway into the real topic.

2. STRUCTURE: the conversation broken into ordered parts (e.g. state the
   decision, give the reason, explain what happens next, invite their
   response) with what to say in each part.

3. ANTICIPATED REACTIONS AND RESPONSES: 3-4 likely reactions from the
   employee (anger, negotiation, silence, tears, pushback on the reasoning)
   and a specific, calm response to each.

4. WHAT NOT TO SAY: phrases that create legal or morale risk in this
   specific type of conversation (e.g. comparisons to other employees,
   promises you can't guarantee, admissions that sound like the real
   reason is different from the stated reason, anything that could be
   read as discriminatory) — explain briefly why each is risky.

5. FOLLOW-UP DOCUMENTATION CHECKLIST: what to write down and file
   immediately after the conversation (date, who was present, what was
   said, what was agreed, next steps) so there's a clear record.

RULES:
- Keep the language direct and humane — no corporate euphemism that
  obscures the actual message (e.g. avoid vague phrases like "moving in
  a different direction" without also stating the real reason plainly
  in the script).
- Every reason given to the employee in the script must be specific and
  tied to the context I gave you, not generic.
- Do not soften a termination or PIP to the point that the employee could
  reasonably leave the room unsure what actually happened.
- If my context is missing something critical (e.g. no documented prior
  warning before a performance termination), flag that as a risk before
  giving me the script, not after.

OUTPUT FORMAT: the five sections above, plus a closing note reminding me
this is not legal advice.

CLOSING DISCLAIMER (always include verbatim at the end of your output):
"This script is a communication aid, not legal advice. Employment law
varies by province/state and by situation — confirm your approach,
required notice, documentation, and any severance obligations with an
employment lawyer or your local employment standards office before
proceeding with a termination or a formal PIP."

How to use it

  1. 1Pick the exact situation you're facing and give real, specific context — vague context produces a script that won't survive an actual conversation.
  2. 2Read through the full script once before the meeting so the structure feels natural, not memorized word-for-word.
  3. 3Pay close attention to the "what not to say" section — these are the phrases most likely to turn a hard conversation into a legal or documentation problem.
  4. 4Before a termination or PIP, confirm your approach against your province's or state's employment standards, or with an employment lawyer, using the closing disclaimer as your prompt to actually do it.
  5. 5Have the follow-up documentation checklist ready to fill in immediately after the conversation, while details are fresh.
  6. 6If the employee's real reaction differs from what you prepared for, use the "anticipated reactions" section as a starting point, not a script to force the conversation back into.

Example

Input: Situation: terminating for performance. Employee: Warehouse Lead, 14 months tenure. Context: two documented written warnings in the last 4 months for missed shipment deadlines, a formal PIP was completed last month with no sustained improvement. Already communicated: both warnings and the PIP outcome were discussed directly with the employee.

Sample output excerpt:

OPENING LINE: "Thanks for meeting with me. I want to get right to it — today is your last day with us."

STRUCTURE: State the decision first, in one sentence, before any explanation. Then: "This follows the PIP we completed last month and the two written warnings before that around shipment deadlines. We didn't see the sustained improvement we needed, and that's the reason for this decision." ...

WHAT NOT TO SAY: Avoid "we just don't think it's a good fit" as the sole reason — it contradicts the documented performance record and weakens your paper trail if the decision is ever challenged. ...

This script is a communication aid, not legal advice. Employment law varies by province/state and by situation — confirm your approach, required notice, documentation, and any severance obligations with an employment lawyer or your local employment standards office before proceeding with a termination or a formal PIP.

Pro tip

Practice the opening line out loud, alone, at least twice before the meeting — the first sentence is where most managers drift into softening language under pressure, and getting it right sets the tone for the rest of the conversation.

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