The prompt library

I'm screening a new opportunity against our box: sectors [list], EBITDA [$10–75M], leverage up to [X]x, hold size [$X]M, senior secured. Here is the teaser: [paste / attach]. In five lines tell me: (1) is this worth a deeper look and why, (2) the single strongest reason to pass, (3) the two pieces of information I'd need before I could decide. Be blunt — assume my time is the scarce resource.

Read this teaser. Give me the three things most likely to kill this deal in our credit committee, and the three questions I should ask the banker before spending any more time on it. Don't be polite about the weaknesses. [paste / attach]

I can only progress one of these this week. Here are two teasers — Deal A: [paste], Deal B: [paste]. Compare them in a short table on credit quality, downside severity, and fit with our box, then recommend which to prioritize and the one reason that decides it.

I'm uploading a CIM. First, in plain English: what does this company actually do, who pays them, and how does it make money? Skip the marketing language. Then give me the top five risks to credit quality — for each, the evidence from the document with a page reference, and one line on the mitigant the sponsor is offering (if any). End with the three things my investment committee will push hardest on. [attach CIM]

Read this CIM and state the sponsor's growth thesis in three sentences, stripped of optimistic adjectives. Then list every assumption that thesis depends on, and tell me which single assumption is most fragile and why. [attach]

This CIM is a sales document. Tell me what's conspicuously absent — the data, disclosures, or context a careful lender would expect to see and doesn't. For each gap, explain in one line why its absence matters for credit. [attach]

Pull every quantitative claim about market size, growth rate, or market share in this CIM into a table: the claim, the page, the source it cites (or "no source"), and your read on whether it looks defensible. Then tell me which three claims I should independently verify first. [attach]

Here is the financial covenant section [paste]. Translate it into plain English: what does the borrower actually have to do each test period, and what happens if they miss? Then tell me what's borrower-friendly and what's lender-friendly about it, and the one definition (EBITDA, debt, cash) most likely to be gamed.

Given this covenant package and an opening total leverage of [X]x, walk me through exactly what happens if EBITDA falls [15]%: do they trip the leverage covenant, and do the add-backs and EBITDA definition let them avoid tripping it? Show the calculation, and tell me the level of EBITDA decline that actually breaches.

Compare this documentation and covenant package to standard market terms for a sponsor-backed [unitranche] of similar size and sector. Where is it loose and where is it tight? Give me the two points I'd most want to negotiate and a one-line justification I could use with the sponsor for each. [paste]

Here is a section of a credit agreement [paste] and here is our firm's preferred position on these points [paste]. Produce a redline-style list of the specific changes I should request, ordered by importance, each with a one-sentence rationale I could drop into a markup. Flag anything in the draft that's a hard no for us.

Walk me through this model. What are the tabs, what does each one do, and what are the four or five assumptions that drive everything else? Then flag anything that looks circular, hard-coded, or inconsistent between tabs.

Stress this model: drop revenue growth by [300]bps and EBITDA margin by [100]bps in years 2 through 5. Tell me total leverage, fixed-charge coverage, and maintenance-covenant headroom in each year, and build a new tab with the output. Then tell me the single assumption the downside is most sensitive to.

Here is the EBITDA bridge from reported to adjusted [paste / attach]. List every adjustment with its dollar amount and the rationale given, and grade each one: defensible / arguable / aggressive / won't fly. Order from most to least defensible. Then total the "aggressive" and "won't fly" adjustments as a percentage of adjusted EBITDA, and tell me what adjusted EBITDA looks like if I strip them out.

Here are the key figures from this model [paste]. Check them for internal consistency — do the revenue growth, margins, working capital, and cash conversion hang together, or is something too good to be true? Flag anything contradictory and tell me the one number I should personally verify against source first.

Build a comparison table across these [3] companies on the dimensions that matter for credit: scale (revenue/EBITDA), growth, margin, leverage, customer concentration, cash conversion, and the single biggest risk for each. Here is the data: [paste]. After the table, tell me which one is the strongest credit and which is the weakest, and why.

Based on everything in front of you, draft a confirmatory diligence question list organized by workstream: financial, commercial, legal/structural, and operational. Put a star next to the questions whose answers could actually change our decision, and cut anything that's just box-ticking. [attach materials]

Based on these three lead risks [paste], build a management-meeting question set. For each risk give me: (a) the framing question I'd open with, (b) two or three follow-ups to push if their first answer is generic, and (c) one question saved for the end to test whether they're being straight with me. Then add five questions about the business itself that aren't about risk.

For this investment thesis to work out, what would have to be true? List the five most load-bearing assumptions, and for each one tell me how I could actually test it in diligence and what evidence would make me comfortable or kill it. Here's the thesis and materials: [paste].

Using everything I've given you, draft a first-pass IC memo with this structure: (1) the deal in two sentences; (2) why we like it — three specific bullets, no marketing language; (3) the three biggest risks, each with the evidence and how we get comfortable; (4) what we're still trying to figure out in confirmatory diligence; (5) recommendation, one direct paragraph. Match a direct, analytical tone — no "compelling," no "differentiated," no hedging. Don't put any sponsor marketing phrase into the memo.

Read this memo as the most skeptical PM at my firm — 25 years in, has seen every flavor of bad deal. What are the three questions they'll ask me first that I haven't answered here? Then rewrite the two weakest sections to pre-empt them. [paste memo]

Cut this to three sentences for an IC member who has 30 seconds. Don't lose the recommendation or the single key risk. Then give me a one-line version for the subject line of an email. [paste]

Rewrite this so every sentence is direct and willing to be on the record. Remove "potentially," "may," "could be," "we believe," and any corporate adjective. Keep my meaning and my recommendation intact — just make it sharper and shorter. [paste]

Draft a follow-up email to [the CFO we met Tuesday], who [was interested but needs to talk to his board first]. Keep it short and useful — give him something concrete to act on (offer a one-page summary of the key terms he could share with the board). Don't sound like a robot. Goal: [a next conversation this week].

Draft a short note to a [sponsor deal team] that's gone quiet after [our second meeting]. Direct but not pushy. Give them one easy reason to reply and a clear next step. Two short paragraphs maximum.

Draft a two-paragraph LP update on [portfolio company]. Plain and confident, no jargon: what changed this quarter, what we're watching, and why we're comfortable — or, if we're not, what we're doing about it. Don't overstate; LPs trust candor. Here are the facts: [paste].

Here's a long email thread [paste / open in Outlook Copilot]. Summarize it in five bullets for my PM: where it stands, what's been decided, what's blocked, and the one thing that needs a decision from us. Then draft a two-line reply I could send to move it forward.

Here is a portfolio company's latest compliance certificate, quarterly financials, and my call notes [attach]. Summarize the quarter in five bullets: the trajectory, the single watch-list item, and what materially changed since last quarter. Flag anything trending toward a covenant or liquidity problem.

Compare these latest results to the original investment thesis [paste both]. Where is the company tracking ahead of underwriting, and where is it falling behind? Be specific with numbers, and tell me whether the original thesis still holds or needs revisiting.

Draft a two-paragraph portfolio update for my PM — direct, no padding. Flag the one thing they should care about most this quarter and what I recommend we do about it. Here's the quarter: [paste].

From these financials and the covenant definitions [paste], calculate current headroom against each financial covenant. Then tell me how many quarters of [10]% year-over-year EBITDA decline it would take to trip each one, assuming everything else holds.

Pretend I'm a new analyst and walk me through [a PIK toggle / this covenant structure / this sub-sector] for the first time. I want to actually understand it, not just know the definition. Use a real example I'd see in the market, and slow down where it gets technical. I'll stop you to ask questions.

I'm going to ramble for ten minutes about a problem I'm stuck on. Don't interrupt me and don't try to structure it — just let me talk it out. When I say I'm done, pull out the three things I'm actually worried about, the thing I think I should do, and the thing I'm avoiding. Be honest with me.

Assume we did this deal and two years later it's a workout. Tell me the most likely story of how it went wrong, step by step. Then tell me which early-warning signs I could start watching for now, and which covenant or reporting item would catch each one first. Here's the deal: [paste].

Build me a primer on [sector]: how the industry is structured, the three or four large players, typical unit economics, how recessions tend to hit it, what private credit lenders specifically worry about in this space, and the questions I should always ask management for a company here. Then pick the one thing most analysts get wrong about this sector.