Peter DeCaprio Insights

Credit · Venture debt · Infrastructure

Questions for Management That Change a Credit View

Ten questions for a management meeting whose answers could move a lending decision, and why each one reaches past the prepared presentation.

Peter DeCaprio seated at an office desk in a white shirt, reading a printed document, with a lamp, a monitor and a window behind him

Most management meetings arrive with an agenda already printed. It runs through the company history, the market opportunity, the strategy and the growth plan, and it has been rehearsed. I read it before the meeting and then put it to one side. The agenda answers questions the company wanted asked. The time is better spent on questions whose answers could change whether I lend, how much, or on what terms. A question that cannot move the decision is politeness, and there is little time for it. What follows is the list I work from, and the reason each item earns its place.

What would you cut first if revenue fell sharply?

This tells me whether management has already thought about a bad year, which is its own answer. A team with a ready list, naming specific costs and specific projects in order, has done the work a lender would otherwise have to do for them. A team that answers with a general promise to be disciplined has not. The content matters too. If the first thing cut is maintenance spending, the savings are borrowed from the future, and my stress case needs to show that.

Which customer would you least like to lose?

Concentration shows up in the numbers, but the numbers do not say which relationship is fragile. Management knows. Asking which customer they would least like to lose, and why, often surfaces a contract up for renewal, a buyer who has started dual sourcing, or a relationship that depends on one salesperson. The answer tells me where to push in the customer calls and what portion of revenue I should treat as less certain than it looks.

Where does cash get stuck between the sale and the collection?

Every business has a place where cash waits. It might be inventory sitting in a warehouse, receivables from a slow paying segment or work in progress on long projects. I ask management to walk the path from order to payment and say where the delays are. If they cannot describe the cash conversion cycle in plain terms, they probably do not manage it, and working capital becomes the line in my model I trust least. If they can, the answer usually comes with a figure for how long each stage takes, and those figures go straight into the stress case.

What did your worst recent quarter teach you?

Every company has had a bad period. How management describes it tells me whether they learned from it or explained it away. I listen for specifics: what they saw late, what they changed and whether the change stuck. An answer that blames the weather, the market or a single customer and stops there suggests the next bad quarter will arrive with the same surprise attached.

Who has to agree before you borrow more?

This question is about control. In a sponsor owned company the answer may be the sponsor’s investment committee. In a founder led business it may be one person. In a company with several lenders it may be a group that has never had to agree on anything. Knowing who decides tells me how quickly the capital structure could change after I lend, and whether my position could be diluted by someone I will never meet.

What would you sell if you had to raise cash quickly?

The answer reveals which assets management regards as separable and roughly what they think those assets are worth. It also shows which assets they consider essential, and those are the ones a lender most wants to understand, because they will not be sold until the very end. If the list of sellable assets is short, the recovery case depends almost entirely on the business continuing to operate.

Which cost saving are you proudest of, and will it come back?

Management is usually happy to talk about efficiency gains. The follow up question is whether the saving is permanent. A renegotiated supply contract may reset at the next renewal. A reduction in headcount may reverse as soon as volumes recover. My interest is in which margin improvements are structural and which are timing, because the model I build treats them very differently.

What do suppliers ask of you now that they did not before?

Suppliers are often the first outsiders to notice stress. If they have started asking for deposits, shortening terms or requiring guarantees, they are telling me something the financial statements will only confirm later. Management sometimes answers this more candidly than a direct question about liquidity, because it feels like an operational detail rather than a financial admission.

How are you personally paid?

Incentives shape decisions more reliably than strategy documents. If management is rewarded on revenue growth, expect acquisitions and aggressive pricing. If rewarded on an equity exit, expect a focus on the reported earnings figure a buyer will pay a multiple of. Neither is wrong, but a lender should know which way the pressure runs, and should build the covenants and the limits on restricted payments with that pressure in mind.

What would you do with a year of surplus cash?

A good year tests a management team almost as much as a bad one. The answer shows the order of priorities: paying down debt, building a reserve, investing in growth, or returning cash to owners. Lenders rank somewhere in that list, and I would rather hear where before lending than find out afterward from a distribution notice. The answer also tells me whether the limits I negotiate will feel like a guardrail to this team or like an obstacle they will spend every year of the loan working around.

At the end of every meeting I ask one more question, and I have never regretted it. What should I have asked you that I did not? The answer is sometimes nothing. Sometimes it is the most useful thing said all day. Managers know where the soft spots are, and many will point to one when invited, if only because it is better for them to raise it than for a lender to find it later. So the last question is always the same, the one I would keep if allowed a single question: what should I have asked you that I did not?