Questions to Ask Real Estate Investors
Questions to ask a real estate investor when you want to learn how the business really works: how they got started, how they find and price deals, how they borrow, what tenants and repairs take out of a month, and what has gone wrong. Every question has a note on what a useful answer sounds like, and a few are for anyone thinking of putting money into an investor's deal.
The questions
Each question, and why to ask it
Getting started
How did you get started in real estate investing, and what were you doing for a living at the time?
Why ask it
The job they had matters as much as the story. A salary, a trade or a partner's income is often what made the first loan and the first repairs possible, and it shows how far their route fits your own situation.
Do you mainly hold rentals, flip houses, or do something else, and why that over the others?
Why ask it
Long-term rentals, flips, wholesaling and vacation rentals are different jobs with different hours and different risks. Their reason for choosing one is usually about temperament or the cash they had, which is the part you can compare with yourself.
What was your first deal, and would you do it again?
Why ask it
Get the plain facts first: what it cost, what it needed and how long they kept it. First deals hold the honest mistakes, so 'I would do it exactly the same way' usually means the story has been polished over the years.
Which mistake do you see first-time investors make most often?
Why ask it
Ask for a person, not a principle: someone they watched do it and what it cost. If the answer is 'not starting sooner', push once more, because that is a slogan and you came for a story.
What would you tell someone with limited capital who wants to start this year?
Why ask it
Say how much you actually have, because advice for five thousand and advice for fifty thousand are not the same advice. A straight answer often points away from buying this year at all, toward saving, learning one neighborhood or working on someone else's project first.
How many units or deals do you have now, and how long did it take to get there?
Why ask it
Scale and timeline together separate a decade of steady work from a lucky run in a rising market. An investor who gives the first number and slides past the second is often newer than they sound.
What do you know now that you wish someone had told you before you bought anything?
Why ask it
The answer is often not about property at all: a partner, a clause in a loan, how long a renovation really takes. Find out what it cost them to learn it the slow way, which tells you how seriously to take it.
If you were buying your first property today, what type would it be?
Why ask it
A single-family house, a duplex and a small commercial unit ask very different things of a beginner in cash, lending and tenants. Notice whether the answer matches what they bought first, and ask what changed if it does not.
Did you keep your day job while you built this, and when, if ever, did it make sense to leave?
Why ask it
A steady salary is often what a lender wants to see, so the job can be the thing that keeps the buying going, and plenty of investors never leave theirs. If they did quit, get the figure they waited for: what the properties had to clear each month before they gave notice at work.
What was worth paying for when you were learning, and what was a waste?
Why ask it
Most investors can name one book, forum or local class that helped and one expensive course that did not. Be a little careful if the answer turns into a recommendation for a program they earn a commission on.
Which local groups or meetups were worth your time, and who else should I talk to?
Why ask it
A name is the most useful thing you can leave with. Check whether you may mention them when you get in touch, since an introduction from a known investor tends to get a reply where a cold message may not.
Finding deals
How do you find deals now, and how is that different from when you started?
Why ask it
Listings, auctions, wholesalers, letters to owners, a call from an agent who knows what they buy: each source takes a different kind of effort. Methods wear out, so the change over time is the lesson, along with whether they still do the looking themselves.
What does a property need to have before you will bother running the numbers?
Why ask it
Investors call this a buy box: a short set of filters such as price band, bedroom count, age of the roof and the street, which lets them reject most listings at a glance. Write theirs down, then draft your own, because clear filters save more evenings than any spreadsheet.
What is the best deal you have ever done, and how did it come to you?
Why ask it
Separate the method from the timing. A deal that came through a relationship, or from a problem other buyers would not touch, can be repeated. One that worked because prices jumped the following year cannot.
What do you look up about an area before you buy there?
Why ask it
You are after their sources as much as their checklist: the county website, a property manager's vacancy figures, a drive around after dark. The follow-up is which one has changed their mind about a street they liked on paper.
Which neighborhoods or markets do you avoid, and why?
Why ask it
Listen to the reasons more than the names: property taxes, insurance costs, flood maps, how slowly the local court moves. Reasons about costs and rules are worth writing down. Remarks about the kind of people who live somewhere are not analysis, and they tell you something about the investor.
Do you buy close to home or at a distance, and what has that choice cost you?
Why ask it
Local owners can drive past a problem, while distant owners depend entirely on the people they hire. Whichever they chose, get the story of the time it went wrong, since that is when the trade-off shows.
What are you seeing in your market right now that someone outside it would miss?
Why ask it
This is the answerable version of asking where the market is going. An active buyer knows how long listings sit, how many bidders turn up and whether rents are being achieved or only advertised. Treat any prediction that follows as a guess, theirs included.
How do you work with real estate agents, and what makes one worth calling back?
Why ask it
Investors tend to want different things from an agent than a home buyer does: rent figures, speed, and no flinching at a low offer. If you are an agent, the answer is a job description. If you are a buyer, it is a list of things to look for in your own.
How do you arrive at your offer price, and how many offers does it take to land one?
Why ask it
The first half shows whether the price comes from their own numbers or from the asking price. The second resets expectations: an investor who writes many offers for each purchase is telling you that rejection is part of the method.
What do you check between an accepted offer and closing?
Why ask it
Inspection, title, existing leases, utility bills and permits are where a deal on paper meets the building. Find out what one of those checks once turned up that made them renegotiate or walk away.
What do you do in a stretch when nothing on the market works?
Why ask it
Sitting still is harder than it sounds once money is waiting. Some widen the search area, some accept a lower return and some simply wait. Which one they did last time tells you more than which one they recommend.
The numbers
Can you walk me through the numbers on something you bought recently?
Why ask it
A real walkthrough shows the assumptions a summary hides: the rent, the empty months allowed for, the repair budget, the price they expect to sell at. It is a big ask, so offer to leave the address out, and take a refusal without pressing.
What return do you need before you will sign, and how do you calculate it?
Why ask it
Cash-on-cash return, cap rate and total return are different sums, so start by pinning down which one their number is. Then check whether it pays them anything for their own hours, which is an easy line to leave out.
Do you buy for monthly cash flow or for appreciation, and has that changed?
Why ask it
Cash flow pays the bills while you wait, and appreciation is a bet on a future sale price nobody controls. Investors who switched sides usually did so after a particular year, so ask which one.
Which expenses do new investors always underestimate?
Why ask it
Expect to hear about big replacements such as a roof or a furnace, the cost of turning a unit over between tenants, and insurance that goes up at renewal. Push for an amount per unit per year from their own records, which is more useful than a percentage rule.
Which rule of thumb do you still use for a first look, and where does it fail?
Why ask it
Shortcuts such as rent as a share of price are fine for sorting listings and poor for deciding. The second half of the question matters most, because a rule that held in their market may be badly off in yours.
How do you estimate rent and repair costs on a place you do not own yet?
Why ask it
Both figures are guesses until someone tests them. A careful answer involves phoning a local manager about rents and walking the property with a contractor. A casual one stops at an online estimate.
How do you decide whether an upgrade will pay for itself?
Why ask it
The plain test is extra rent or sale price against the cost, inside a time limit. Get one improvement that earned its money back and one they would never repeat, such as a kitchen too good for the street.
What surprised you about taxes once you started investing?
Why ask it
Depreciation, how a sale is taxed and what counts as a repair all differ by country and by your own circumstances, so treat the answer as a list of topics. Take that list to an accountant who works with property owners where you live.
Do you go back after a year and compare a property with what you projected?
Why ask it
Going back to compare is how estimates get better. The detail to collect is which line was furthest out last time, whether that was rent, repairs or empty months, and whether they changed the assumption for the next purchase.
Financing
How do you fund purchases, and what does your debt look like right now?
Why ask it
Debt is usually what turns a bad year into a forced sale, so the shape of it matters: fixed or variable rate, how long the term is, when anything comes due. A large loan maturing in two years changes how you should hear every other answer.
How did you pay for your first property, and would that route still be open today?
Why ask it
Savings, a family loan, living in one unit of a small building, a seller who carried the note: the first purchase is often funded in a way the later ones are not. Lending rules and rates move, so find out what a beginner would have to do differently now.
What does a lender ask of an investor that it does not ask of someone buying a home?
Why ask it
A larger down payment, cash reserves, rental history and a different rate are common, though the details vary by lender and country. Hear what surprised them the first time they applied, then put the same question to a broker where you live.
Have you borrowed from hard money or private lenders, and what did the money end up costing?
Why ask it
Short-term loans are quoted as a rate plus fees, and the fees and extension charges can add up to more than the rate suggests. The project that ran past the loan's term is the one to hear about.
Have you bought with a partner or with other people's money, and how was it split?
Why ask it
Who put in cash, who did the work and who signed the loan should all have been written down before the purchase. Pay attention to how they describe a partner they no longer work with.
If someone wanted to put money into one of your deals, what should they ask you first?
Why ask it
Use this one if you might hand them money one day. A straight answer covers results they can document, their fees, what happens when a deal loses money and how an investor gets out. Raising money from outside investors is regulated in most countries, so check that side with someone independent.
Has anyone who put money in with you lost some of it, and what happened next?
Why ask it
Save this for when you are seriously weighing an investment with them, and then do not skip it. A calm, detailed account of a deal that fell short, including who was told what and when, is a better sign than a spotless record nobody can check.
How did your portfolio behave when rates moved, and what did you change?
Why ask it
Anyone who held a variable rate, or had a loan come up for renewal while rates were rising, has a concrete answer. Steer toward what they did, whether that was refinancing, pausing purchases or building up reserves, and away from how it felt.
Managing
Do you self-manage or use a property manager, and what changed your mind?
Why ask it
Plenty of owners start out doing it themselves and hire a manager at a certain number of units or after one bad tenant, and some go back the other way. Ask what the trigger was and what the manager's fee did to the monthly figure.
What does your tenant screening involve, step by step?
Why ask it
You want the order of events: application, income check, references, a call to the previous landlord. Anti-discrimination law limits what a landlord may ask or weigh, and it varies by place, so find out which rules apply where you would buy.
How do you set the rent, and how do you raise it on a tenant you want to keep?
Why ask it
Setting it is research. Raising it is a judgment about what an empty month would cost against a small increase, and some areas cap increases or require notice, which is worth asking about too.
What do you do when a tenant stops paying?
Why ask it
Have them tell it in stages: the first phone call, the written notice, the point where a lawyer or a court got involved, and how many months it all took. Eviction rules differ a great deal between states and countries, so their timeline describes their area and may not match yours.
How long does a unit usually sit empty between tenants, and what shortens that?
Why ask it
Days empty is a number a careful landlord knows without looking it up. The practical part is the timing: when the listing goes up, when the painter and cleaner are booked and who shows the unit.
What repairs do you do between tenants, and which ones are never worth it?
Why ask it
Paint, flooring, appliances and the yard are the usual list. What they stopped doing teaches more, whether that is replacing carpet a deep clean would have rescued or repainting walls that only needed touching up.
What happens when something breaks in the middle of the night?
Why ask it
Every owner has a burst pipe or a dead furnace story. Behind the story is a system, so listen for who the tenant calls, who may spend money without asking, and up to what amount.
Who is on your team, and how did you find them?
Why ask it
A reliable contractor and a lender who understands investor loans tend to be the hardest people to find. How they were found, whether through a referral, a supplier's counter or a bad experience with someone else, is advice you can use this month.
How do you pay a contractor so that the job gets finished?
Why ask it
A common pattern is a small deposit, payments tied to finished stages and a final amount held until the last item is done. Schedules like that are usually learned by paying too much too early once, so ask about that job.
What do you use to keep track of rent, bills and repairs?
Why ask it
The tool matters less than whether they can pull up one property's year in a couple of minutes. If the answer is a shoebox and a good memory, weigh their return figures accordingly.
How much of your time does this take in a normal month?
Why ask it
The honest figure is what separates a hands-off holding from a second job. A normal month hides the real cost, so follow up with the worst month they have had and what filled it.
Risk and exits
What is the worst deal you have done, and what did it cost you?
Why ask it
A number makes this the most useful story of the conversation, and what they changed afterwards turns it into advice. An investor who says they have never lost money on a property is either very new or not answering the question.
How much cash do you hold back for each property, and when did you last dip into it?
Why ask it
A reserve that has never been touched is a theory. The last withdrawal, whether for a roof, a long vacancy or a tax bill, tells you what size is realistic for the kind of property they own.
What insurance claims or legal problems have you actually dealt with?
Why ask it
A burst pipe, a fall on the front steps, a dispute over a deposit, a neighbor's fence: the examples show what really goes wrong. Two details are worth having, what the policy turned out not to cover and what they changed in their leases afterwards.
How do you hold title, and what did your accountant or attorney advise about structure?
Why ask it
Whether to own in a personal name, a company or a trust depends on the country, the lender and the owner's wider finances, so their conclusion may not transfer to you. What does transfer is who advised them, what it cost to set up and what they would ask that adviser now.
Which local rules have changed your plans: rent limits, short-term rental bans, zoning?
Why ask it
Regulation is the risk a spreadsheet cannot price, and it arrives by council vote. Find out how they hear about a proposal before it passes, whether through a landlord association, council minutes or an attorney.
What would have to go wrong for you to be forced to sell?
Why ask it
It is a blunt way of asking how fragile the portfolio is. Answers that name a specific combination, say two long vacancies and a loan coming due, come from someone who has done the arithmetic.
How do you decide between holding, refinancing, and selling?
Why ask it
Some investors refinance to pull cash out for the next purchase, some sell when the equity tied up in a building could earn more elsewhere, and some never sell. Look for a stated trigger, a number or an event, and not a feeling about the market.
What made you sell the last property you sold, and what was left after costs?
Why ask it
Agent fees, repairs before listing, the loan payoff and tax can take a large bite out of a headline gain. A seller who knows the net figure to the dollar was keeping score the whole time they owned the place.
What are you buying now, and what would make you stop buying?
Why ask it
The stopping condition is the real measure of how they read risk. Confident plans with no stopping condition at all are worth remembering when you weigh the rest of their advice.
What is the long-term plan: how many properties is enough, and what happens then?
Why ask it
Some investors want a set monthly income, some want to hand buildings on to their children and some have never thought about stopping. The goal explains choices that otherwise look odd, such as paying loans off early or selling a property that is doing well.
Learning from working investors
Practical guidance for the conversation itself
Getting the conversation at all
- 1Go where they already are. Local landlord association meetings, county auctions and property manager events tend to work better than a cold message.
- 2Ask one specific question instead of asking for mentorship. A specific question can be answered in ten minutes, and an open-ended request for guidance is easy to ignore.
- 3Offer something concrete in return: driving to a viewing, pulling comparable sales, checking permit records, sitting an open house. Time is the currency here.
- 4Follow up with what you did after their advice. That message is what tends to turn one conversation into a second.
Choosing from a long list
- Over a coffee you will get through five or six questions. Pick the ones from the part of the list where you are stuck, and keep the others for a second meeting.
- At a meetup, stay in Getting started and Finding deals. People answer those happily in front of others, while debt and losses belong in a one-to-one conversation.
- With a landlord in the family, lean on Managing. Those are the answers only someone who owns in your area can give you.
- If you are an agent meeting an investor client, start with what a property needs to have, the return they need, how they fund purchases and how they like to work with agents. Those four tell you what to send them and what not to.
- If you may invest with this person or lend to them, the Financing and Risk and exits questions stop being curiosity and become due diligence. Ask to see documents as well as hear stories.
What to listen for
- Timelines. A portfolio built in three rising years teaches different lessons from one built across a downturn.
- Whether numbers come with sources. Rent, taxes, and insurance are all checkable, and investors who quote them precisely usually track them.
- Losses told with figures. A story that ends with what they changed afterwards is worth more than any success they describe.
- Labor. Ask who does the work, since a return that depends on their own unpaid weekends is not the return you would get.
- Whether their strategy still works. Some methods depended on interest rates or prices that have since changed.
What not to ask
- Their net worth or income. It gets you a defensive answer, and the interesting numbers are per-deal anyway.
- For free analysis of a property you are considering. Ask how they would analyze it instead, then do the work yourself.
- For money at a first meeting. It puts someone who was happy to talk in the position of having to refuse, and it usually ends the conversation.
- Whether real estate is a good investment right now. It is too broad to answer and it invites the market speech. Ask what they are seeing in their own market instead.
- For a partnership before you have done anything on your own. Bring evidence of work first.
Verify independently afterwards
- In many places ownership records, tax assessments and recorded sale prices are public, though some regions keep sale prices private. Where you can, look up a deal they described instead of taking the numbers on faith.
- Where permit records are open to the public, they show whether renovations were approved, which says something about how carefully someone operates.
- Check any rent or vacancy figure you were quoted against current listings and a local property manager's view.
- Take anything you heard about tax, lending or legal structure to a professional where you live before acting on it. An investor's experience is one person's, in one place.
- Anyone recommending a paid program, a fund, or a syndication is no longer only giving advice. Treat that part of the conversation differently and ask who pays them.