The first few times it happens, it feels like a positive signal.

Somebody wants your advice and perspective. You must be good at what you do.

And that’s gotta translate to your career…somehow, right?

Thing is, it’s fun to feel appreciated, right up until the moment when you don’t feel appreciated anymore.

You realize that your time and expertise is worth more than a cup of coffee (even if it’s really good coffee). You get tired of people ignoring the advice they asked for (or worse, doing the complete opposite ).

Maybe the only reward for giving out free advice is…being asked for more free advice?

And maybe that’s why nearly every single one of my creative friends have added to the collective groan:

“Ugh, another person just emailed me asking if they can buy me a coffee and pick my brain about a project. Don’t they realize my time is valuable?”

Say yes? Say no? Scream into the void?

I’m the kind of person who likes helping people. I’m also the kind of person who doesn’t like saying no, especially when I’m pretty sure I can help someone. These two traits are a dangerous combination.

And I owe a lot of my business success to being generous with what I’ve learned. It’s why I’m able charge premium prices for my consulting work. It’s a large part how I’ve built relationships with smart, interesting people around the world.

Sharing is part of my personal and professional DNA.

So instead of slapping a price tag on my coffee dates, I’ve come up with a much better system that helps weed out time-wasters, boost my own industry credibility and puts me back in control…all without saying “no.”

Here’s how it works.

Start with this Magic Email Response

If you’ve indulged in coffee dates that let people pick your brain, you’ve probably noticed that a lot of people don’t have an idea of what they actually want to ask…or they have a bunch of lead-in questions before they actually get to the REAL question they want to ask.

I want this person to get to one of those questions as quickly as possible, without using my time to figure out what question they even have.

So while I often slightly tweak the exact response, almost every inbound “hey, can I pick our brain?” type message gets a version of this email response:

I’m happy to help! I do keep my limited 1-1 time available for my consulting clients, students, and Indy Hall members, so right now the best way for me to help will be to know what questions you have upfront. Try to pick 1-2 that are most important to you, and the more specific the better!

Send those over and I’ll try my best to respond as soon as I can!

This magical email does a couple of very important things.

With little more than a copy/paste, this email weeds out a good 70% of inbound requests from random people who haven’t and won’t bother to think about what their questions are ahead of time. I’m unlikely to be able to help them, anyway.

It also takes the pressure off me to work on their schedule. I can respond in a moment of downtime, or while I’m in transit (I do a lot of email triage on my commute to make it productive).

And when people who DO respond with specific questions (which is less than 3 out of 10 times), I can kick off the second stage of the process in one of a few ways.

Sidenote: sometimes the questions I get back are vague. Sometimes the person ignores the “1-2” questions constraint, and sends back 20 questions. I consider both of these red flags that the person isn’t really listening or trying. If they weren’t far off I’ll give them a direction to get more specific or pick a priority. Other times, a gentle “sorry I won’t have time to answer this” provides honest closure. Careless or absurd requests get ignored.

Option 1: Get your answer on record.

You don’t have to give a lot of advice to realize that you’re giving the same advice over and over.

It might sound annoying, but Step Two of my “magic process” hinges on this fact.

The problem with coffee date brain picking is that the advice you give (along with the time spent giving it) is lost into the ether. Helping one person at a time - for free - isn’t terribly scalable. But what if the advice you give one person could help two, ten, hundreds, or even thousands of people…without the impossible effort of sit down to coffee with each individual person?

So whenever I see a new question (emphasis on new, more on that in a second), I try to give my answers in some kind of recorded fashion:

  1. Most often, it’s some written form like an email or a comment on a discussion list.
  2. Sometimes I’ll record my answer as audio or video, and transcribe it with later with a service like Temi.

It doesn’t need to be the quality of something that I’d publish, so I don’t worry about editing. It’s just the best advice I can deliver in the least amount of time.

And I hit send.

Option 2: Don’t Repeat Yourself

This step is where the magic really happens.

Some time after I’ve hit send (sometimes later that day, often a week or two later), I’ll copy/paste my answer (or the transcript) into a text editor. I’ll carve out an hour or two to edit, give it some structure and context, maybe even fill in some gaps that my original advice was missing, or could be clearer. I remove anything specifically identifying about the person or situation that prompted the request - or in some cases, I’ll specifically ask them if I can keep a detail or context that is identifying, but only with their permission.

And then I publish that.

This is magic for two reasons:

First, I never, ever, ever stare at a blank page and wonder “hm, what should I write about?”

But second - and this is my absolute favorite part - is that the next time someone asks the same question (or a very similar one) I can link them directly to a answer-on-record that I wrote before they even asked me the question.

This little move saves me hundreds of hours a year, makes it possible for me to help thousands of people, and all the while makes me look like a goddamned wizard who can read minds.

Option 3: Offer a consultation

While most advice can help more than just the person asking for it, that’s not always the case.

In the cases where someone truly wants custom-tailored 1-1 advice, and that advice directly relates to your line of business or how you earn a living, then what they’re reallying asking for is a consultation.

For these folks, I offer a fixed rate (at a premium price) for a 90 minute video call.

This is the vast minority of inbound requests, but also the majority of serious requests.

And for anyone who balks at the price, I kindly point back to the free advice I’ve published in past articles as available anytime they like!

The hidden benefits of video calls

I prefer video over just audio because seeing someone’s face is super important to me when I’m in a consulting dialogged, but there are significant benefits to this being a “digital” meeting:

  1. I don’t have to change locations. 15 mins of walking to a coffee shop on either side of a 90 minute call is another 30 mins, compared to 5 mins to jump in a phone room at Indy Hall or wherever I am.
  2. Doing these calls using Zoom video chat means I can offer a recording of the conversation as part of the package. They don’t have to worry about taking notes, and can reference the FULL conversation anytime in the future. I don’t have to worry about them emailing back “what did you say about XYZ again?”

Logistically, I only offer these calls on certain days of the week and during certain times where it’s less likely to interrupt my workflow.

Calendly makes it super easy for them to pick a time that works for them without losing time to the calendar shuffle. And with a paid account, I can even ask for payment to complete the booking.

I used to be more shy about this step, but once I got confident in explaining how it works people started booking. Here’s an example of the language I use.

90 minute Q&A Consult: $XXX. This blocks out an a hour and a half for us to go deep into the questions you have, ask clarifying questions, etc. After the call I provide a recording of the video for your future reference, plus any additional resources that might be useful based on the answers given. You can book one of these here: < Calendly Link >

Option 4 (rare): Dinner or drinks

Depending on the person who’s asking, I might decide to say yes to grabbing a drink and/or dinner…but it’s rare. This is most commonly if it’s someone I already know and like (or want to get to know better), and I’m upfront about the fact that I’m interested in hanging out. The advice thing is just part of the convo.


There’s one habit that ties it all together

This entire process hinges on just one habit:

If I catch myself giving a piece of advice more than 2-3 times, I force myself to write it down before the next time I get the question.

And for a bit of meta, that’s exactly how this blog post came to be!

The rest is relatively easy, so long as you use the formula:

  1. Use the magic email to get specific, pointed questions.
  2. Point to articles/resources with your past answers, once you have them written down.
  3. Give people an easy way to pay for your time, on your terms

Common side effects include…more sales & better customers

At the beginning of this article, I said:

Maybe the only reward for giving out free advice is…being asked for more free advice?

Well, over time, your library of free advice will become more comprehensive. The longer you stick to the plan, the more valuable it gets.

But unlike spending countless hours sinking into another cup of coffee with no results, having a library has made it easier to offer products and services that people are happy to pay for after getting so much value from the free library.

I help more people, with less time and effort, and earn more on my own terms.

All without having to say “no.”


There's more where that came from

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