Hard Conversations

The conversations support agents dread don't come with a macro. The furious opener. The third contact on the same bug. "Get me your manager" in the first sentence. A refund you have to refuse. A customer who mentions a lawyer, or tells you something heavy in the middle of a ticket about invoices.

Hard Conversations gives you a move for each of them. It's written for software and B2B support, where the ticket history is part of the conversation, the fix often sits with engineering or billing, and one account can have several people pulling in different directions. Its method starts from the ticket record rather than the tone: count the contacts, name who owns the next action, find what the customer stands to lose, and the stuck map tells you which play to use.

Each of the 24 plays covers one situation: what to do in order, a decision rule, words you can say in your own voice, the reflex line not to say, the traps to watch for, a check to run before you send, and a short agent prompt for drafting written replies. Every play has a matching role-play card, so a team lead can turn the book into weekly practice instead of a document nobody opens.

For leads, two plays tackle the "new people escalate everything" problem directly: how to write decision boundaries agents can act on (with a worksheet of starting defaults and the reasoning behind each), and how to run a short weekly role-play hour. A measure sheet shows you how to tell, from your own team's data, whether any of it worked.

Plays that touch distress, legal mentions, abuse, contracts or employment matters tell you to follow your company's policy and route to the right owner. Nothing in the book is legal, HR, medical or crisis advice.

What's inside

• 24 plays in six chapters: anger, uncertainty and waiting, saying no, pressure and boundaries, tricky situations, and making it stick
• Every play: the situation and trigger, the move, a decision rule, "say it like this", "don't say", what to watch for, a fallback, a check before you send, and an agent draft prompt
• 24 role-play cards: a customer brief, the agent's goal, what good looks like, and the one behavior the coach watches (the two lead cards flip it: the coach plays the agent)
• The method: read the ticket before the tone, with the stuck map for choosing a play from contact count, owner of the next action and what the customer stands to lose
• A "Start here" reading order on the welcome page, one for agents and one for team leads
• A "find your play" table: start from what the customer is saying and jump to the right play
• Decision boundary worksheet for leads, with labelled starting defaults and the reasoning for each
• Escalation route card, with a handoff summary format
• Six of the most used plays adapted for voice, chat and email
• Three made-up conversations, each with the bad version beside the fixed one
• Five worked judgement calls, plus a table of what you'll often be told and what to do instead
• A measure sheet for tracking manager requests, reopens, third contacts and missed updates on your own team
• Phrase swap sheet: common lines that inflame, and plain alternatives
• Four longer agent prompts: rewrite my draft calmer and shorter, turn a long thread into a playback, check my reply for blame language, prepare me for a hard call
• Role-play hour scorecard
• A 46-page PDF you can print or keep open next to your queue

Who it's for

• Frontline support agents at software and service companies who want words for the conversations that rattle them
• Team leads who onboard and coach agents and want a ready-made practice kit
• New agents who escalate everything because nobody has written down what they can decide

Who it's not for

• Anyone looking for legal, HR or crisis guidance: the book points you to your company's policy for those

Good to know

• Written by Draft First, a customer success and support lead.
• The examples use made-up companies and people.
• The agent prompts produce drafts for you to review. Use an AI tool your company approves.
• Free sample: three complete plays with their role-play cards.
• Questions: hello@draftfirstcs.com
• All sales are final, so please read the free sample first.

Get Hard Conversations

Questions before you buy? Email hello@draftfirstcs.com.