The Best Questions To Ask in an Informational Interview [Real Estate]

Informational interviews can be really powerful networking tools, but if you aren’t asking the right questions during these conversations, these can end up going to waste.

And in my experience (having done hundreds of these throughout my career), there’s a huge variation in the value you can get from a meeting or a phone call, and this almost all comes down to how you guide the conversation.

So in this post, we’ll walk through five of the most powerful questions you can ask in an informational interview, and why each of these is so important.

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Question #1: “Why did you decide to get into real estate?”

In my opinion, this is one of the best ways to start a conversation, because this can give you a lot of insight into how your values and goals line up with those of the person you’re talking with.

This can also help you understand whether this person followed through on what they initially wanted to accomplish, and whether the career path they pursued is something you’d want to emulate.

I’ve talked to a lot of very successful senior leaders of some very big companies who have answered this question by telling me they had always wanted to start their own firm, but eventually, life got in the way.

In other situations, I’ve talked to people who were absolutely determined to make their goals a reality, and these people told me about the risks they took and the issues they ran into when trying to make that happen.

My goal was always to weigh the advice of people who had very intentionally built their careers more heavily than the people who didn’t end up where they wanted to be, even if those career paths didn’t look as prestigious on paper.

I also love asking this question because it tends to be one of the best ways to make these conversations human and less transactional overall. This question allows you to understand each person’s values and priorities at a much deeper level, while also getting a clearer picture of how those align with what you personally value.

Question #2: “If you had to start your career over again, what would you do differently?”

This question is a great way to indirectly ask people about what they regret about their career, and this can give you a very honest look into the mistakes that people ahead of you have made.

Some of the answers to this question I’ve heard over the years include acquisitions managers wishing they had gone into brokerage, chief investment officers wishing they had struck out on their own, and VPs of huge companies wishing they had jumped ship to a smaller, more entrepreneurial firm.

This question is a great way to get more clarity on what career paths provide the most income upside, what career paths provide the most autonomy, and what career paths provide the best work-life balance in the industry, so this is a really helpful question to ask if you’re not sure where you want to start.

Question #3: “What’s something people think your job involves, but actually doesn’t?”

This question directly calls out a lot of preconceived notions that you might have, that could also have a major influence on the career path you choose to pursue.

Answers to this question I’ve heard over the years include travel being a lot less glamorous than it sounds (especially as you get older), the amount of time spent doing more tedious, time-consuming work being a lot more than you’d think as you start to manage more people, and even a lack of involvement with some key parts of the transaction process for senior acquisitions professionals working at bigger firms.

I like this question because it’s a very respectful way to ask someone about the least appealing parts of their job, and this can help you get a much more realistic sense of what your day-to-day experience might be like if you were to go down a similar path.

Question #4: “What’s the most worthwhile thing you did early in your career to progress more quickly than your peers?”

When you’re just starting out in commercial real estate, there are a ton of things you could pay attention to, but the answers to this question will help you use your time as efficiently as possible.

Responses to this I’ve heard over the years include joining industry organizations, taking on certain projects at work, pursuing additional real estate-specific education or training, or even moving to a new city for exposure to new opportunities.

I like this question a lot because it can give you very clear direction on the most impactful things you can do with your time, especially when you hear this from people you admire.

Question #5: “Based on what you know about my background and goals, is there anyone else in your network you’d recommend I talk to?”

This is one of the biggest networking hacks I know of, and this can allow you to exponentially grow your network (if you go about this the right way).

The goal of asking this question is not to be overly pushy and ask for a connection to a specific person, but if you come off during the conversation as hard-working, respectful, and full of potential, a lot of people are going to be willing to make an introduction to at least one person in their network.

If someone isn’t comfortable doing this, they’ll often say something like, “I’ll think about it and get back to you,” and they ultimately won’t follow up. However, if the person does end up wanting to help you, the potential upside to asking this question is huge.

This one question allowed me to get in front of some of the most successful people in the industry (who would have never agreed to talk to me with just a cold email), and this is one of the best methods out there to make connections quickly.

Two Key Things to Remember

When you have these conversations, there are two things you want to keep in mind, regardless of the questions you decide to ask.

The first thing to keep in mind is that you want these conversations to be as natural and fluid as possible, so don’t go into a phone call or meeting with the goal to march through a pre-built itinerary. Instead, ask follow-up questions on things the person is talking about and treat this as a normal conversation, rather than just a way to extract information.

The second thing to keep in mind is to make sure you follow up with these people within 24 hours of the initial conversation to say thank you, highlighting a few key pieces of advice that stood out to you from the meeting. Several months after the initial conversation, you’ll also want to follow up with your progress, how you implemented each person’s advice, and how the conversation has impacted your career.

The more you can make it clear that you were listening and taking the conversation seriously, the more likely it is that you’ll be able to build a long-term relationship with the people you connect with. And if you plan to build a career in this industry, these connections can help you many years down the road.

More Networking & Job Search Strategies

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