What a coach walks in with
This is everything Grapevines hands a coach before they meet someone. It starts with a resume and a fifteen-minute conversation. Nobody on the coaching team typed any of it.
Rosa Delgado · 11 years in hotel operations, Mexico City · moving into product roles in software
Fictional person. The employers, target companies and people in this packet are invented for demonstration. No real participant data appears anywhere in it.
Inside
| 01 | How this gets built | inputs and time |
| 02 | The resume she uploaded | the raw material |
| 03 | The positioning conversation | five questions, her answers |
| 04 | The read | who she is, with the evidence |
| 05 | Her story, ready to use | positioning, bridge story, talking points |
| 06 | For the coach | what to spend session one on |
| 07 | Between sessions | the plan she sees |
Input 1
Her resume. Uploaded when she joins the program. One page, written the way most people write them: duties, not decisions.
Input 2
A positioning conversation. Five questions, about fifteen minutes, on her own time before the first session. The questions adapt to what she says.
The read. Her positioning in plain language, the strengths worth leading with, and the paths she's positioned for. Each strength cites something she actually said or did.
Her story, ready to use. A positioning statement, a bridge story for "why the change," talking points with the evidence behind each, and a LinkedIn headline and opening.
Notes for the coach. What's already handled, what's worth the first session, and what to watch for.
A plan between sessions. Short, ordered, and in front of her on the days her coach isn't there.
Roles, companies and people come later. Once she and her coach choose a direction, every role she considers gets scored with the gaps named, and each company gets researched along with the people worth contacting.
A coach can disagree with all of it. Disagreeing with a draft is faster than starting from a blank page, and that is the whole idea.
What your firm sets. Where participant data is stored, which parts go to AI providers, whether the people lookup runs at all, how long anything is kept, and whether your reporting shows totals or individual detail. Set per program.
Rosa Delgado
Mexico City · rosa.delgado@example.com · +52 55 0000 0000 · linkedin.com/in/example
Uploaded 14 March
Operations leader with 11 years in hotel operations, most recently directing a 214-room property. Experienced in team leadership, process improvement, systems implementation and budget ownership. Seeking a role where I can apply operational expertise in a technology-driven environment.
B.S., Hospitality Management
Universidad Anáhuac, 2014
Spanish (native) · English (fluent)
Team leadership · Process improvement · Budgeting and P&L · Vendor management · Systems implementation and training · Opera PMS · Salesforce · Excel
Certified Hotel Administrator (AHLEI), 2022
What Grapevines flagged in it
Buried: a software rollout for 200 users, a process redesign across five departments, and a reopening plan. Each is a product-shaped decision described as an operational duty. Missing: a number on any of the three. Working against her: the summary sells "operational expertise," which is what files her under operations.
She answered these on her own, before the first session. The questions follow her answers, so no two participants get the same five. Her words are unedited.
When everything was running smoothly, what did that actually look like?
"Nobody had to ask anyone anything. The front desk knew a VIP arrival was coming before housekeeping finished the room, engineering already knew the AC was out on that floor, and the night manager didn't have to explain any of it to the morning shift. When it works you can't see it working. When it breaks, a guest is standing in the lobby at midnight and three departments are blaming each other."
Used for: the positioning line, and strength 3.
You listed a systems migration. What was the hardest decision in it?
"Whether to run both systems for a month or cut over in one night. Everyone wanted the safe version, both systems, but that means every person doing double entry at 2am and getting it wrong. I chose a phased cutover, department by department, and I made front office go last because they had the most to lose. We trained 200 people in six weeks. Two departments hated it for a week and then it was fine."
Used for: strength 1, and the bridge story.
What do people come to you for that isn't in your job description?
"Translating. The GM speaks in numbers and the floor speaks in problems. I spent years in the middle of that. Also anything involving a vendor who isn't delivering what they sold us."
Used for: the translation framing in the read, and talking point 2.
What do you want less of in your next role?
"Being on call for a burst pipe. I don't mind pressure, I mind pressure that has nothing to do with judgment. I want to work on the thing that stops the pipe from being everyone's problem in the first place."
Used for: the paths she's positioned for, and a flag for the coach. She's moving away from something, which is worth a conversation.
Where do you think you're weakest for the roles you're looking at?
"I've never written a product spec and I don't know what they expect one to look like. I can tell you what a system should do and why, but I've been the customer, not the builder."
Used for: the vocabulary gap, and what to prepare her for in interviews.
Why this step matters. Everything later in this packet traces back to one of these five answers. A resume on its own produces a generic read, which is why most tools produce the same summary for everyone.
What her resume says
"Operations leader with 11 years in hotel operations… seeking a role where I can apply operational expertise in a technology-driven environment."
Reads as: keeps things running. Files under operations.
What the conversation says
"I spent 11 years learning how complex systems break when real people use them. I ran a 214-room property where three shifts and five departments had to hand off work without asking, and I built the processes that made that true."
Reads as: designs systems for people under pressure.
1. She has run a software rollout for 200 non-technical users.
Evidence: the PMS migration. Phased cutover by department, front office last, six weeks of training, no interruption to service. In an interview this is adoption and change management, not "systems implementation."
2. She translates between people who don't share a vocabulary.
Evidence: her own words, "the GM speaks in numbers and the floor speaks in problems," plus five departments on one handover process. This is the part of product work nobody can teach.
3. She designs for the failure case.
Evidence: an escalation procedure adopted by two sister properties, and a handover redesign aimed at the midnight lobby rather than the happy path.
Positioned for
Product manager, platform or operations tooling · Implementation or onboarding lead at a hospitality software vendor · Director of operations technology on the buyer side
Worth a conversation with her coach
She is clear about what she's leaving and vague about what she's running toward. Those three paths pay differently and move at different speeds. That's a session-one question, not a packet question.
Drafted from her resume and her five answers. Hers to edit, and her coach's to push on.
Positioning statement
An operator who designs systems for people under pressure. Eleven years running hotel operations, including a software rollout to 200 non-technical users, now moving into product.
Bridge story: her answer to "why the change?"
"For eleven years I was the customer. When our hotel moved to a new property management system, I chose a phased cutover, one department at a time, and we trained 200 people in six weeks without interrupting guest service. That project showed me I care more about how the system works than about running the building around it. Product is where those decisions get made."
Three talking points, with the evidence
"I've run a software rollout for 200 people who didn't ask for it."
Behind it: the PMS migration. Phased by department, front office last, no interruption to service.
"I translate between the people with the numbers and the people with the problems."
Behind it: her own words about the GM and the floor, and five departments on one handover process.
"I design for the night it breaks, not the day it works."
Behind it: an escalation procedure two sister properties adopted, and a handover built around the midnight lobby.
LinkedIn, drafted
Headline: Operations leader moving into product · 11 years making hotel systems work for the people who use them
About, first lines: "I've spent eleven years on the operator's side of hospitality software: choosing it, rolling it out to 200 people, and fixing what broke at midnight. I'm moving into product to work on the systems themselves."
What still needs her. Three of her strongest claims have no number attached: guest complaints before and after the handover change, training completion inside the six weeks, and overtime during the cutover. Any two of them make these talking points much harder to ignore.
Already handled
Her history, her positioning, three strengths with the evidence, a bridge story, talking points and a LinkedIn draft. None of it needs session time except to be argued with.
Worth the hour
Watch out for
What this is not. No recommendation about whether to hire her, no ranking against other participants, and no score that leaves the program. The coach decides what to do with all of it.
Before session one
→ Read your positioning out loud. Mark anything that doesn't sound like you. Your coach will start there.
→ Find two numbers. Guest complaints before and after the handover change, and how many of the 200 finished training inside the six weeks. Both strengthen your talking points.
→ Rewrite one bullet. The PMS migration, told as a decision: the users, the tradeoff, the result.
Hold until after session one
→ The LinkedIn changes. Your coach may change which path you lead with.
→ Applications. Bring the roles you've been eyeing to the session instead. Once you've chosen a direction, Grapevines scores each one and researches the companies and people behind them.
What the coach sees
Whether each item got done, and what she wrote when she did it. Not a score, not a ranking, and no nudge sent in the coach's name.
That's the packet. One resume and a fifteen-minute conversation produced all of it, before anyone on the coaching team spent a minute on her file.
Manav Thaker · Founder, Grapevines · mp@grapevines.ai · grapevines.ai