Episode 34 - Picking Brains


Jen: Hi, Peter.

Peter: Hi, Jen.

Jen: I want to pick your brain about something that I find annoying -

Peter: Huh.

Jen: - which is when someone asks if they can pick my brain.


Peter: I did not see that coming. Yeah, let's - I'm happy for that. You want to pick my brain on picking brains?

Jen: Yes, I do. Are you ready to have your brain picked?

Peter: I think so. This is The Long and The Short Of It.

That was very funny. I did not see that coming.

Jen: Well, I was writing a blog post last night, and what I was trying to express was how to find more clarity in an ask, if what you're doing is trying to ask someone for a favor or ask someone for help. And I thought about what are the typical asks I receive, and the overwhelming majority of them contain a sentence like, "I'd love to pick your brain," stop. And so I was thinking about - and I'd love to get your take on this - a couple of different things: one is, is it hiding to not state outright exactly what you want to talk about? Two, does it really require a full hour of drinking coffee to pick someone's brain? And three, how can we help people to find their courage and get clear on the kind of help they need so that other people can actually help them?

Peter: Mm. I feel like the third point that you made is worthy of discussion. The other two feel like easy answers.

Jen: Yeah.

Peter: The first is, yes, yes, it's hiding. Yes, absolutely it's hiding. If you don't have a specific idea or intention, if you haven't even got one, or if you've got one, but you're not willing to share it with the person, instead you're trying to cover up this idea of, "I have a favor I want to ask Jen, but I don't want to ask her the favor, I'm just going to ask her whether she'll allow me to pick her brain," yes, that is hiding. And we can dig into that some more, but my first response is, yes, that's hiding. Your second question about sixty minutes - absolutely not. Sixty minutes is arbitrary. It's like, the default setting of human beings when we create a meeting, and we go, "Bleep bloop bleep, it must be sixty minutes" - that was me attempting to be a robot, not a human. But yeah, we default to sixty minutes without, without even thinking why. And often, it's the sixty minutes, but then it's like, maybe the coffee shop is twenty minutes away, and so I have to get there, and then I sit there and I have the sixty-minute meeting, and twenty-five of the sixty minutes might be about the thing that they want to talk about, or less, and then the rest of it is, "How about the weather?" and you know, like, pleasantries, I guess. And then you got to walk the fifteen minutes home. So I don't want to come across as, like, anti-catching up for people with coffee, because I love catching up with people with coffee, but in this situation, based on what you just described, I think yes, they're hiding, and no, it doesn't require sixty minutes.

Jen: And wouldn't it be nice if someone wanted to catch up with you if they just said, "Hey Peter, I'd love to catch up with you."

Peter: Yeah. Yes. "You know what, I just haven't, haven't had a chance to catch up with what's happening in your life, and I would love to do that." Like, that would be great. I'd be like, "Sure."

Jen: Yes. For that, I've got sixty minutes.

Peter: Yeah, and likewise with, "Hey Jen, I would love to pick your brain on how you think about storytelling and delivering keynotes for audiences that are corporates," you know, like, I dunno, that was a terrible example, but, "I would love to, like, really specifically talk to you about this one thing." And now you know, "Hmm, am I in the mood to talk about that? Do I think I have something to contribute to this person based on that topic? And is it something I could just send them an email about or refer them to, I don't know, a blog post, or a podcast that I've written already that might help them? Could we do a phone call?" Like, there's all these other options, obviously, as well, so, hmm -

Jen: Yeah.

Peter: - I'm really, I'm really obsessed with, I'm really obsessed with the first point though you pointed out, which is that it's a form of hiding.

Jen: Yeah. Well, there are a couple things there. One is, when you speak in generalities, and/or you create homework for the other person - which, when you don't tell someone what the meeting is about, that could really start the other person needing to do some work on their end to try to figure out where you're coming from - when you do either of those things, I think what you have done is given yourself an excuse. So you are essentially setting yourself up for a "no," and then you don't have to do the work of actually showing up and asking for what you need. So if you are general about it, "Can I pick your brain for sixty minutes?" and someone says, "No," then it's really easy to go, "Well, that person said no to me," or, "I was rejected," or, "I guess people really don't want to help." So it's like, setting yourself up for the easy way out.

Peter: Yeah, it's like, confirmation bias of the story that you want to tell yourself, which is, "I tried. I really tried, but in this case it just didn't quite work out."

Jen: Yeah. I'm reading this book right now which is rocking my world, which is called, the book is called Who Are You, Really?: The Surprising Puzzle of Personality by Brian R. Little. And this was published by TED, and it's a, fittingly, a little book, but it is, it packs a punch. It is so interesting. It's so amazing. Anyway, we'll probably have to do a whole separate episode on everything I've learned from this book, cause it's really blown my mind, but one of the questions he asks is, when you acknowledge what you're doing, like, "I'm reaching out to Jen to see if I can pick her brain for sixty minutes," you've got to really ask yourself, "What do you think you're doing?" So, do you think that you are planting the foundational seeds for a longterm relationship? Do you think that you are establishing a mentor/mentee relationship? Do you think that you are building your professional network? What do you think you're actually doing when you do the things that you're doing? And just that little reframe is so powerful. So when you ask someone, for example, "Can I pick your brain?" what do you think you're doing?

Peter: I love that. It reminds me of, I was gonna say, another way of asking yourself a question or thinking about this is like, what's the question behind the question? Is, sure, you've asked, "Can I pick your brain?" but like, what are you really asking? What's the, what's the question behind that question? Because you're hiding behind that very general question. So I think that that, like, talks to what you just described as well. And, I mean, what, what is also very obvious in hearing all of this, all of these ideas as we talk about them is, essentially, we are, we're telling and reminding listeners to be clear on "What's it for?"

Jen: Yes.

Peter: The ultimate question of, if you're going to do something, do it with intention. Ask "What's it for?" and be clear in what that intention is. And, "picking someone's brain?"

Jen: No. Ouch.

Peter: It's not very clear. And yeah, also painful. Ow.

Jen: And the other thing is, the action of "picking someone's brain" is so unspecific, that as the person on the receiving end of that, I feel like I don't know what I'm getting into, but if someone - so here are some examples of things that have been very successful when someone has asked for help: so I've had people reach out and say, "Hey Jen, I'm moving into a coaching role, and would love to talk to you about your first year in business and how you helped people see you as a coach when they were used to seeing you a different way."

Peter: So specific.

Jen: I will totally sit down and talk to you about that, because I know, I know the answer to those questions. Or someone might say, "Hey," - there's an example I used in my blog post - "Hey, I'm thinking of going back to graduate school, and I've narrowed it down to three programs, and I'd love to show you what the curriculum is, and based on your knowledge of my work, which of these three feels like the best fit for what I need to learn?" Yes, I will totally sit down with you and do that, but I, on the other extreme end of the spectrum, have gotten requests like, "Hey Jen, would love to sit down with you and talk about coaching."

Peter: Yeah.

Jen: It's like, are you, you want to sell me on your coaching? Do you want me to coach you? You want to just talk about what it's like to be a coach? Like, what are we talking about?

Peter: Yeah, I - it's funny you just, like, sparked a thought, or a memory where just recently I got an an email from someone asking whether I would be interested in catching up to discuss how we might work together, and I was like, "In what, in what capacity? And also who are you? What do you do? What - do you know what I do?" Like, just this, this idea of collaboration and working together was kind of the, that was the body of the email, and I was like, "What?" But if they had been so much more specific like you just described, perfect examples, then I can make the decision of, "Yes, this is worth my time, because I might be able to help you in this way," or, "No, it's not worth my time, but I know someone who will be able to help you. I can point you over here."

Jen: Well, it's funny because it seems like people are trying not to step on toes, where it's like, "Well, I don't want to be too specific, because I don't want this person to think I'm presumptuous," but it is far more presumptuous to be general and just presume that someone would give you an hour of their time when you haven't acknowledged any of the projects of theirs that you are aware of, where you're coming from, or what collaboration means to you. So it is so much more unlikely that someone would say "yes" to an hour-long conversation about collaboration, as opposed to, "Would love to talk to you about having you as a guest on my podcast," or, "Have you considered co-writing a blog, a blog post, one from the perspective of what it's like to be in the audience of a keynote, and then also from the perspective of the keynote deliverer? I would love to collaborate on that one thing with you."

Peter: Hmm. Sounds like a cool blog post, by the way.

Jen: Doesn't it?

Peter: I think - yes, all of that. And what I would use in my head as a way to think about that is, it's generous, like, it's generous to be more specific about what your intention is. And I know that people might think that, "Oh, it's, it's easier if I just say, let's pick, I want to pick your brain because I," like you said, "I don't want to step on toes. I don't want to presume anything. I don't want to, like, say one thing and they, and then they decline, because they're actually more interested in talking about the other. So I'll just throw a blanket over it and that will be more generous." But I agree with you that it's more generous to be clear. And I mean, Brene Brown talks about "clear is kind," right? Like, so it's so much more generous for you, to the other person, to be clear on, "What's this for? What's the question behind the question? What do you really want to talk about, and how might I be able to help you?"

Jen: Well, while we're talking about thought-leaders, another way to look at this - yes, "clear is kind, unclear is unkind" - thank you, Brene. Also, let's look at this through the "Start with Why?" lens from Simon Sinek. If, "Can we sit down for an hour so I can pick your brain," that is starting with "What?" If you were instead to start with "why?" talk about what you're about, talk about what's inspiring to you, what is it that's inspiring about the work the other person is doing, and then get to the "What?" after you've started with the "Why?"

Peter: Yeah. I think that's really important, and I, I don't think, like, I don't want this to come across as, I don't think it's worth catching up for people with coffee, because I think, I think, like, so many of us, so many of those conversations have led to some amazing, like, collaborations, or some amazing clients, or some amazing freelancers that you've ended up hiring, but I think most of them don't start out - in fact, almost all of them haven't started with, "Let's just have a general conversation about I'm not really sure what." Most of them have started with some sort of intention, and whether or not you go in there and you leave having only talked about that thing, I doubt it, like, it might be that you end up down a rabbit-hole (if you have a conversation with me, we'll probably end up down three rabbit-holes, and you might end up walking away having talked about something else), so it's not, like, if there's that fear that that's the only thing you're going to talk about, if you put that in the the body of the email or reach-out, or whatever it is, I don't think that's necessarily a valid fear. Like the, the purpose of an email to you, Jen, to say, "Can I pick your brain?" really the purpose is, "I'd love to get some time in Jen Waldman's calendar," and then whether I get there and we talk about something a little bit different, like, that might be okay, but as long as you're obviously acting with integrity and not just completely lying, saying, "I want to talk to you about this thing, and I'm now I'm going to talk to you about this thing and pitch you," I think, like, we're human beings, it's going to be a conversation, so naturally we're going to move around.

Jen: I think that's a great call-out, and I'll just share that from my own personal experience: if I'm the one doing the reaching out and wanting to connect with someone, and I don't know specifically what the agenda is going to involve, but it's really not brain-picking, I'm not trying to just take from the other person, I want there to be mutual giving, I'll say something like, "I've been following your work. I'm really excited about what you're doing. There are some really interesting projects going on on my end, too. Would love to sit down with you, share what we're each working on and see where there might be some overlap." So to me, that's the less intrusive and yet still specific way to say, "There's work that we both like that may lead to a collaboration, but I'm not suggesting before we sit down and meet that we might be collaborators," that, that feels presumptuous to me. But to sit down and say, "I'd love to hear what you're working on. I'd love to share what I'm working on and see if there are any interesting overlaps."

Peter: Yeah. But also in that, in that example you described, you're, you're almost laying out a little bit of, "This is what I am working on, and this is what I know you're working on." Like, so you're actually, you've done a bit of research, and you've done a bit of homework to say, "I think it's worth our time, basically, because I see a little pattern, but I would love to sit down and see if that pattern is real."

Jen: Yes. And I think what you have just pointed to is so critical to a successful interaction, which is, do your homework. Do your homework. If you are asking someone a question that could easily be found by typing it into Google, you have not done your homework, and it doesn't warrant the other person offering up the time to sit down if you're coming to the table, having not lifted your own weight.

Peter: So yes, do your homework. And also, I think that reach-outs don't have to be - I mean, I know we started this talking about reach-outs being about "picking brains" and catching up - I also think that there is so much room for a generous reach-out with no ask, right? Like -

Jen: Yes!

Peter: - I've started to get into the habit of, when I read a good book, I'll just reach out to the author and say, "I really liked your book because of this reason. It made me think about this, so thank you for writing it." And I send them with no, like, expectation of a reply, cause they're a successful author, they're most likely incredibly busy. But what's interesting is often they reply, and just say, "Hey, thank you so much. That means a lot." And I'm not asking for anything. I don't want to pick their brain, necessarily. I mean, I would love to, but that's not the purpose of that reach-out. The reach-out was just a generous thank you, and I, I don't know if we do enough of that, to be honest.

Jen: I agree with you. I am very big on, well, what you call "good finding." When you find something that's good, tell the person who made it that you're aware of it, and that it mattered to you without any need for a reply. Like, when you click "send," that's it, you've crossed the finish line, you don't need to worry about it anymore. But you're right, sometimes the icing on the cake is that someone will reach back out. I've actually already started working on my reach-out to Brian Little, because this book is blowing my mind, and I of course want to say, "Thank you for blowing my mind," without asking for anything. I don't need to sit down with him for an hour to talk about the things in the book that he wrote that he already knows that I want to reiterate. I just want to say, "Thank you for the work that you do, and the impact that it's having."

Peter: I like it. So, we started with brain-pickings, and we sort of finished with brain explosions, and of course, if anyone's out there and feels like reaching out, please do: hello@thelongandtheshortpodcast.com. We love hearing from each and every one of you. And that is The Long and The Short Of It.