The Difficult Conversation Playbook
Scripts for raises, boundaries, feedback and family — what to say, word for word. Thirty conversations, each with the replies you fear and what to say next.
$19.90 one-time · PDF e-book · 41 pages · instant download
The conversation you are avoiding is running your week
Most people avoid it not because they lack courage but because they do not know the words — so they rehearse a hundred versions and say none of them. This book gives you the words: thirty scripts for the conversations people most often put off, each written to be said out loud, each with the replies you are most afraid of and what to say next.
Money and work
Asking for a raise, raising your prices, telling your boss you are overloaded, declining a task, chasing an unpaid invoice, resigning well, telling a client the project is late.
Feedback
Critical feedback to a colleague, feedback to your manager, receiving harsh feedback, telling someone they didn't get the job, the colleague who takes credit.
Boundaries
Family and money, a boundary with a parent, chores with your partner, ending a one-sided friendship, "I can't be your therapist", the neighbour and the noise.
The hardest ones
A real apology, ending a relationship, confronting a lie, telling a parent to stop driving, asking for a reference, asking a doctor for a second look, telling your team bad news — and the conversations you have with yourself.
Every script, the same spine
Open — one sentence that names the topic without ambush · Fact — what happened, observable · Impact — the effect on you or the work · Request — one specific thing · Invite — a question that hands them the floor. Then If they say… with your reply, and the line to hold onto if it gets heated. Change the words in [brackets]; keep the structure.
Who this is for
Anyone with one of these conversations sitting in the back of their mind right now. Read the chapter, copy the script onto one page, ask for ten minutes, and say it.
About the author
Meir Gilady is an Israeli entrepreneur and independent thinker based in Holon. Alongside a career in commercial real estate he builds software under the AILAMA name — including AILAMA Mind and ToolVerse — and writes about physics, technology and everyday wellbeing on Medium.
Questions
Which format? A PDF laid out for 6×9 in — reads well on a phone, tablet, laptop or printed. Refunds? Full refund within 30 days — reply to your Gumroad receipt.