Taylor Rooks on How to Instantly Connect With Anyone

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1:33There's no safe like SimpliSafe. From Entrepreneur Media, this is Problem Solvers, a show that solves entrepreneurs' toughest problems. I'm Jason Pfeiffer, Editor-in-Chief of Entrepreneur Magazine, and each week I take a problem that you're probably dealing with and get tactical solutions from people who have been there and solved that. So, let's get solving. When I was single in my late 20s, I had this strange recurring experience while dating. And I promise this is going to loop back around to business, but just stick with me for a second. So, I'd go out on a date with a woman, and we wouldn't really click, and I'd be totally bored, which, you know, is a normal thing on dating.

2:12Not everyone is a match. Then I would get home after this boring date, and I'd have an email or text from the woman who I just saw who thought that it went great. and she's telling me what a great time she had and how she can't wait to do it again. And after a few of these, I thought to myself, what is going on here? Like, I can't be that special. And then I realized the problem. The problem is that I have a journalism background, which means that I learned how to ask questions and carry a conversation and develop a quick rapport with someone. Because in journalism, you only have so much time with people and you need to get them comfortable and trust you and share information and do it pretty fast.

2:53And so that's what I had been doing on autopilot on these dates, which I didn't even realize. And that was probably very different from all of these dates that these women had had with guys who did not know how to ask questions or just talked about themselves all night or whatever. And that is where the miscommunication happened. Anyway, I was thinking about this recently because I was invited to talk with Taylor Rooks. And if you're an NBA fan, then you definitely know Taylor Rooks. Here is how the Today Show describes her. She's one of the buzziest names in sports right now, Emmy-nominated journalist Taylor Rooks.

3:26As the New York Times said, she gets the NBA interviews that go viral. Taylor is the lead host of NBA On Prime, Amazon's new NBA coverage. And in her interviews with NBA players, you can see these guys feeling comfortable around her and opening up to her, which I assure you, as someone who has also interviewed a bunch of NBA stars, is not an easy thing to do. These guys can be really guarded. And I got to thinking, you know, this is a skill that entrepreneurs need because when people like you, they buy from you or work with you or work harder for you. And nobody seems to do that better these days than Taylor Rooks.

4:06So I asked her. And I thought it would be interesting to hear you think back to earlier in your career, because right now you seem to know everybody and you've built that trust. But in the earlier days, how did you start to build that rapport and build it fast? Because that is actually something that entrepreneurs need to know how to do. Walk into a room, build trust really quick. And you have to do it at an incredibly high level with people who are in insane demand? And I bet you've learned a lot about that. Yeah. Oh, great question. You know, I think something that I knew very early on in my life and certainly early on in my career as well is that people really enjoy talking about themselves.

4:52And I think even more than that, it's that people are always actually searching for someone to just listen to them. And it is really surprising how much trust can be built by just opening up your ears and allowing somebody to tell you something about themselves or their lives or their day or their family. There is just this connection that happens when they feel like they can divulge. And I think that sometimes, whether it is in media or in entrepreneurship, a lot of the times we believe that the job is our output, but a lot of the time, like it's really our input. Like I tell people as much as I am supposed to be a talker more than that, I'm a listener.

5:36But I think that that is a fact that is transferable and really in the arena. I think that you can build that, that sort of trust in that relatability, but also that desire to come back to you by making people feel as though not even necessarily that you're on their side, but at least that you want to understand their side. And that has been something that has worked for me for my career. I have to say what follows in this conversation is one of my favorite interviews I've done this year. Taylor is really thoughtful about how to create that connection and how to build upon it. And she shares some pretty interesting personal stuff about it too.

6:18So today on Problem Solvers, it is Taylor Rooks on how to build rapport fast. Really useful if you are an NBA reporter or also an entrepreneur. And it is coming up after the break. All right, we're back. Today, I'm talking to NBA on Prime host Taylor Rooks. Just before the break, she made this great point that people always want to feel heard. And so I asked her, Have you found any go-to ways to start that relationship? And the reason I ask that is because I totally agree with you that the number one thing that people want is to feel heard. But also, people don't always know who they can trust to share with and how that is going to be received.

7:08And the sense that I have gotten, especially when talking to super high level athletes is, look, people are asking them for things all day, every day, and they're getting asked questions. People want to listen, but they don't know if this is a person that they can actually trust to talk to. How do you signal that? So a lot of it, I think, is you're signaling it in the work that you put in. Like, so for me, whenever I'm about to interview somebody, it is incredibly important that I watch all the interviews that they have done. And it isn't just so I can research things about their life or their game or, you know, their team, whatever.

7:49It's also so that I can see what they are always asked so that I can avoid it. Because it's also, are you open to listening to someone or do you want to listen to somebody if you aren't even hearing the things that they've already said? So when these athletes give these interviews and they are asked the same question over and over and over again, why would you feel like this person wants to learn something new about you when they're already asking you information that is already out there? So I think it also starts with, okay, this person cares because they put in the work. They did the research.

8:22They wanted to approach this from creative angles and not things that we have seen over and over again. And with athletes or really anybody in the public eye, who they are or who they are believed to be is already in the room before they even get there. So I think it is your job to parse through what elements of that is real and what isn't. And they want to really have that opportunity to talk to somebody to address some of the things that are, but also confirm some of the things that are. And so I think I established that through the genuine curiosity. And I think that that shines from the moment that we meet.

9:08But I'm also a big believer in just cutting through the bullshit. Sorry, I don't know if we cuss on here. No, you cuss all you want. Like just, you know, cutting through that and just telling you exactly what this is. You know, sometimes I say, I don't want to waste your time and I don't want to waste my time. What works for you in interviews and what doesn't? What do you feel like isn't being talked about? What do you think is misunderstood? Where have people gone wrong? Like, I believe in attacking these things sort of head on so that both people know the corners that we stand on and we can find, you know, what that common ground is for the interview to work.

9:45But I think that that is just a valuable way to approach everything. Tell people what you're about. You know, you want them to trust you. I mean, let let them know that they can and then show that through obviously the examples that they already know about you. but then how you show up in the interaction as well. I really love that answer. And I'll tell you what it makes me think of something that I learned to do a long time ago when sitting down with someone for a cover story. So, you know, if we do an entrepreneur cover story, it's Jimmy Fallon or Michelle Pfeiffer or whatever, and no big deal.

10:22No big deal. Right. Yeah. Just regular people. And I started to do this thing and I didn't even know why I started to do it, but it worked really well. And then I think I came to a reason why. So I'm just going to share it with you and see what your reaction is. Yeah. So what I would do is I would sit down and I would start by saying, Jimmy Fallon, we have a project together today. And that project is this. I write for entrepreneurs and they pick up the magazine because they're trying to build something for themselves. And so I'm not really interested in your pop culture background or any of the kinds of things that like Entertainment Weekly or somebody would ask you about because that's not helpful to entrepreneurs.

11:06Instead, what I want to do is work with you to find the thing that you know really well that entrepreneurs can use in their own business and then basically teach it to them together. So the start of our conversation is going to be searching around for what that is. And then I'm just going to start asking you a lot of follow-up questions and digging into it and trying to get really tactical so that we can teach entrepreneurs something. And when I give them this little spiel, I can see them loosen up and get really excited because I don't think that's something that people often invite them to do.

11:41And I was thinking about why does this work? And the answer that I came to was something that I heard you articulate in that answer that you just gave, which is that what I was really doing was proposing a joint project. You know, whenever you interact with somebody in some way, whether that interaction is small, it's at the grocery store, or it's what you and I are doing right now, it is in some way an interaction where we are going to create something. And maybe that something is just a good experience when I buy my kids Doritos or something, or maybe it's a podcast or whatever of the hell it is.

12:14We have some joint project. And if both people know what their roles are in the joint project, and both people feel like there is a collaboration in that joint project, then you get excited about it. And you feel like you know how to contribute to it. And that is not something that I knew how to do or even thought to do earlier in my career. But it is something that I do a lot now. And I see that it really works. And I hear you doing a version of that too. Yeah. No, I think that's such a great way to put it because yeah, it's like we are in this thing together. And the best thing for both of us is to know what is our goal?

12:53Because I don't really think the goal of, you know, the interview, it isn't to talk, right? It's to talk towards something or talk about something and to give people a takeaway from whatever that discussion is. So the more you can really lay out to your point, what those roles are, what we are looking to accomplish, it's going to feel like a more pointed and valuable discussion. And also to your point, that's for anything. People want to know where they're headed. So yeah, whether it is, you know, you are an entrepreneur, you're like leading a company, it helps when people understand what are we working towards and it can shape their responses.

13:32is. It can shape their actions. So I love that. And I, I completely agree with you. Here's another thing that your answer had made me think of. I hadn't thought about this in a long time, but when I was much younger, I flew to Toronto and I interviewed Benedict Cumberbatch for like 10 minutes. You know, it was like one of those media junkies. I love Toronto, like one of the best great city. It's going to remind me of Chicago. I just, I love it. It's clean. The people are nice. The architecture is really in like uniform in a way, but yes, I love Toronto. Totally beautiful. And that like baseball stadium is really something.

14:09It's great. And good food. Well, here we are. We're actually making a travel show about Toronto. So I flew to interview Benedict Cumberbatch and I was, I was very young in my career and I was very nervous to interview him. And I had like a list of eight questions that I had memorized basically. And the first question, it started with some version of in the whatever upcoming movie you have, you know, you play this character and something, something. And then he jumps in to fill in what he thinks the next part of the question is, which is something like, and how much of that character is like me?

14:49Right. And that's, that's what he thought, because that's what everybody asks every actor, right? It's just like, you're playing this character? How much is that like you? Which is such a stupid question. Who cares? But that's what he thought I was doing. And it wasn't. I can't remember what I had asked him, but it was not that. It was something more thoughtful than that. And so when he said, how much is that character like me? And I said, no, that's not what I was going to ask. And then I was going to ask this other thing. And then I went in a different direction that he didn't anticipate. And this is going back to when you were saying, when you ask the question that people aren't usually being asked, I found that just me introducing something more thoughtful and nuanced than he was used to immediately earned his attention.

15:32And then I think about how the least interesting thing in the world that somebody can reach out and ask me about is getting coverage in Entrepreneur Magazine. I hate that question because I get it all the time. I'm sure you have that version. What is that? What is that for you? What is the thing that everyone asks you all the time? Well, I love the Benedict Harvest, right? It's so good. Because also too, when I hear that, it's like, now I'm curious, okay, is that question frustrating? And like, do we have just a misunderstanding of like what it is to be an actor and where you're pulling from and why?

16:03How often have you asked? Like, I just feel like there's probably this really cool conversation about like, no, when I'm acting, I am acting. And like, I am, that is a decision that I am making. And so he's probably hearing that all the time. It's just annoying. That's true. It's like, whatever you were about to say, please say it. But I just wanted to say, well, you just said that I realized, oh my God, asking that question, like how much is the character like you is actually just revealing probably a misunderstanding of the person's job. And he has like some really enlightening response to like why that's not a question that makes sense to him.

16:42So yeah, no, I love that story. But I, and I love that you're asking something else. What do I feel like I'm always asked about? I am almost always, and I'm sure any woman that is listening through your podcast understands this too, but I feel like I'm always asked about just like what it is like to be a woman. The challenges of being a woman. Right. You know what they say about being a woman in this military industry. Right. And obviously there is space for those sort of discussions because we have to have them. There are many things that I would want to change for women in this space. So I am not discounting the importance of the discussion around the advancement of women.

17:32But I also think that it's a little lazy. One, because I've answered it so many times that there just isn't a new thing. Right, right, right. If you want to know what you think about that, just Google it. Yeah. It's like, I've answered it so many times, but it's like, there also just has to be a more creative way to have that discussion. But I also think that it signals in many ways that you might think the most interesting thing about me is that I'm a woman. Because it is continuing to come up and come up and come up. So I would probably say that, not because there isn't space for the conversation, but because there just has to be a better way to have it?

18:12What do you think is the better way to have it? I think we could all benefit from having this conversation without centering women. I think there is a way to center men because I think that we are all operating within the systems that are presented to us. So what is it that are the issues with those systems and how have those blood into, you know, what it is we believe about women in this space. I think that language is important. I don't really think that we should say that this is male dominated. I think that there are more men. I don't necessarily know if they dominate it. Maybe there's a conversation about the way that we talk about women's space in this.

18:55That's a great parsing of the language. You know, because I also think that we are continuing to, without realizing it, like perpetuate this idea that the women are niched they are being invited into the male space is this like addition as opposed to like being in it because we belong in it and so i think what people are actually trying to hint at when they ask me that question it's actually a question about belonging or owning or dominating or, you know, why are we always framing the challenges of being a woman? There are so many things where I think that my womanhood and my perspective and experience as a woman makes me more suited for the job.

19:46It has opened up doors because of how those experience has shaped me. So I don't know. I just think there are ways to advance it outside of like, what's it like being a woman in a male-dominated industry? It's like, I mean, I don't know. Right. Right. Ask somebody who feels that. But what? So that's the thing. It's also an assumption. You are assuming I believe this could be a hurdle that I am overcoming. And this Taylor interestingly loops back on what we were just talking about a couple of minutes ago. Watch me draw this line. So that question to Benedict Cumberbatch or any actor, what is the character like is, as we just hypothesized, a fundamental misunderstanding of their work and how they think about their work.

20:35And so the question just reveals an ignorance about their work. And you just said this version of the same thing, which is if somebody asks you this question, what's it like being a woman in a male dominated industry? It is a fundamental misunderstanding of the way in which you see your own work and place in this industry. Fantastic. That's not what they're looking for. Although I believe now, again, there are many things need to be fixed. There are challenges, absolutely, that come with it because of these systems that have presented to us. But if your question to me is what is it like being a woman?

21:08It's great. Like that is what my answer is. That is not what they are looking for when they ask me. They want me to feel all of, you know, the pitfalls of being one of the few. Right. And yeah, I don't know. I just, that's probably my, that's my, what parts of yourself have you brought to your role? Yeah. And no, it's great. Right. And what I really love is how through this, what we've done is unpack the way in which questions to people can inadvertently signal a misunderstanding that, to go back to the original theme of our conversation here, could really halt any kind of development of a rapport or trust building.

21:53Because if the first thing that you're going to ask people, or whether it doesn't have to be the first, if it's just infused in there is some version of, I don't really understand you. And I also didn't do the work to understand you walking into this, then you're not going to earn anybody's trust. Are you? No. Yeah. You're no. And it's like, cause an assumption is also in some ways it's like inherently like a limit because you've like put a cage onto the conversation with what you just said that then makes it really hard to get out of because we started from something that maybe isn't reflective or indicative of who that person is or what they believe.

22:30And again, this is about anything, but yeah, you can't, you're just unable to connect when the connection is not coming from the person you're looking to connect to. It is coming from you. Yeah. And I mean, I, I see this in many different iterations in life, but it is for sure something that they can hold you back. Let's just take a quick tactical turn here because how then do you ask the questions that are going to show that you understand, show insight, and do it in a short amount of time? I generally have the benefit because I am not operating on TV time. I generally have the benefit of feeling out a conversation.

23:15You know, the way in which I approach conversations is what I've done with you here, which is like I walk in with basically a general idea of what we might talk about, but I really just lead by listening and whatever you say, I'm going to try to build something on top of. I do a lot of theories. Let me tell you about this. What do you think of that? That's what we've done. And I really love where that goes. You can't do that on TV. You have like 30 seconds to ask somebody something. So how do you do that? Because personally, I've always suffered in that format. I don't know how to be succinct.

23:43You have to. What do you do? Yeah. I mean, depends on the situation somewhat, but leaning into emotions is always great. You know, I see that you have this big smile on your face. Tell me about, you know, the happiness that you feel with X, Y, Z. Although I don't like a tell me about question, but for the sake of it. Sure. I understand. It is the, it is the cliche of broadcast journalism. But yeah, leaning into the emotions, talking about, you know, a year ago or so, I read an article where you said, XYZ, how have you seen that manifest today? So it's also always having like an intake of information about people so that you can refer to other things.

24:28I really love bringing up what people have already said. Yeah, it's a good tactic. It shows that you research, but it also shows that like, you know, life is a progression. what you thought then, maybe you don't think now, or also that thing that you thought could have helped you now, whatever the case may be. So I like bringing up what people say. It is someone that maybe I don't know well, but I know someone that they know. I've always tried to bring that up. No, I was just chatting with your friend, Doug Nowitzki. He said, and then you parlay that into a question. It's always about just like finding little touch points, especially when it's quick, just to put them a little more at ease and feel like they're talking to a friend, but yeah, certainly it's certainly easier when you get to be in the long form setting because you can really build up and you can have that really great opportunity for follow-ups and follow-ups are always asked in sports interviews.

25:24I have sort of realized, but just always making it like a ping pong match. But yeah, I just try to latch onto little things and hope that it leads me down the right path. I love that. And what you're doing is signaling in some way, I talked to this person, I heard you on this thing. You're taking something that you already know is in their head. You already know they think or feel that. You've then signaled that you've done the work and now you're asking them to apply it in a new situation, which forces them to think on the fly, which is really, really interesting. For sure. I also too, I just like never underestimated the value of being a warm person.

26:03like being inviting is one of the best things that you could be ever when i was younger i'd heard that like asap fable about the wind and the sun and like there's a traveler walking down the street and he's trying to they're trying to get his coat off like the wind would blow and blow and blow and so he just pulled the coat tighter but then when the sun beamed this being warmer and warmer and he just took off and i feel that way in this work too like sometimes it can be very easy to get caught up in the, I'm going to have this gotcha moment, or I'm going to create a headline or whatever the case may be.

26:41I think that it is always a lot more lasting, a lot more real, and you have a lot of higher return rate when you act more like the sun and you let people open up on their own with your help, but it feels like it's their decision as opposed to something that they were forced into. So there is a value in being a friend. And I'm sure like in business, sometimes there is that value. People feel like, okay, no, there's value in only being a shark. And I'm sure there's a big value in that. Although once my friend got me this, like a shark's tooth to put on my desk and the reminder is that there's always a bigger fish.