The Art of Asking

It’s Wednesday, September 27th, and today we’re talking about how bad we are at leveraging the wisdom of the community around us, and what to do instead.

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The Art of the Ask

We Need to Get Better at Asking for Help.

Usually, this headline is followed by supportive, encouraging words about how we can’t do it alone and how it’s okay to ask for help.

That is not what I am saying. I am saying that the actual ask is bad.

Making an ask is an art form. As an expert in community, I receive a few of these asks every week. As someone who is hopping in and out of communities all day long, I see members make these asks of each other. It is, perhaps, the single most valuable part of being in community: leveraging the wisdom of those around us.

But hot damn, do we mess it up—and that is a real shame because many of these opportunities can lead to priceless growth. I’ve spent a lot of time coaching members on how to effectively make an ask (and dealing with an influx of my own) and there are some universal strategies here. In this issue, I want to explore:

• How to respond when people ask if they can “pick your brain”

• What a good ask looks like

• A checklist for an effective knowledge exchange

Nails on a Chalkboard

I loathe the words “Can I pick your brain”. It’s usually synonymous with “Can I please waste your time?”.

You've probably heard the phrase more times than you can count. While this question may be well-intentioned, it falls short for two major reasons:

It's vague: Asking to "pick someone's brain" doesn't specify what you need or why you're reaching out. Ambiguity can be frustrating for the person you're approaching. Don’t make them assess and diagnose your problem. Come to the table with specificity.

It's overused: Professionals frequently receive such requests, and frankly, it hurts the brain. The sheer volume of these requests can make folks hesitant to respond. I’ve never wanted to be someone who is slow to respond to people asking for help, but at some point, I just don’t have any more time to give.

I’ve often heard people complain that it lacks reciprocity and that when asking for help, it's essential to consider what you can offer in return. I don’t agree with this. Quid pro quo is not a priority. In fact, this idea is likely responsible for another well-intended question I don’t love: “How can I add value to you?”

Dunno. And don’t really have the bandwidth to figure it out. It’s a nice gesture, but unnecessary.

One of the most important pieces of working for myself is keeping my calendar clear. Freedom is my version of wealth, so when someone reaches out and asks to pick my brain, I respond the same way almost every time. Feel free to use it:

“Hi there! Happy to be helpful where I can. Do you mind starting by shooting over your top two specific questions and we can go from there?”

This allows them to narrow their focus to the parts that matter most and reduces my cognitive load. Nine times out of ten, they never send those questions, because they just wanted to have a general, meandering chat about their ideas.

A Good Ask

Whether it’s a post in a community or a DM on LinkedIn, I’ve noticed that great asks share a few thoughtful components:

1. They’re specific: They clearly state what they’re seeking guidance on. For instance, these are two different DMs I received this month:

“Hey, April! How’s it going? I’m looking to launch a community for [business name] and would love your thoughts on the idea. Can we hop on a call?”

“We have an email list of about 4k people. All of them have taken our free introduction course and I’d like to invite them to be founding members. What would your first step be? Should we be polling them about what they want to talk about or where we should build it?”

While the latter is a big question, it at least gives me a starting point and a clear direction

I wrote it before, and it bears repeating:

…context is more than king; it's a win-win act of efficiency. Context allows people to give way better answers and lessen their cognitive load.

2. They respect my time: I can’t commit to sync conversations. Friends, family, Wondry clients, Techstars, school…like anyone else, there are a lot of priorities to work through. I deeply appreciate when people have a reverence for my time and offer other options for communicating. I’ve had some great conversations that were nothing but an exchange of loom videos.

Adam Grant said it well:

3. They give good context: Not the whole story (remember, start right before you get eaten by the bear), but enough to understand your ideal outcome and why this matters. Particularly in a community post, I see a huge difference in engagement when posters give a little background info.

This idea of honoring the time of those around us is ubiquitous. It’s in community, social media, classrooms, relationships, conference rooms; everywhere. After seeing it done poorly (a lot) and well (sometimes), I present to you:

A Checklist for Getting the Most Out of Your Ask

• Do your homework: Research the person you're approaching to understand their background and expertise. This will help you tailor your request appropriately (generic LinkedIn asks go straight to my trash can).

• Craft a concise message: Keep your initial request brief and to the point. People appreciate brevity.

• Offer flexibility: Be flexible with communication options, accommodating the other person's preferences as much as possible. I really enjoy my communication with David Spinks. We tend to be on the same page and will take audio over video any day, preferring a walk and talk to being tethered to a chair. This makes communicating a pleasure.

• Be prepared: Come to the conversation with specific questions and a clear agenda. This demonstrates your commitment to making the interaction valuable for both parties. And it really helps you get the most helpful answers.

• Show gratitude: Express your appreciation for their time and insights. A simple "thank you" can go a long way.

• Follow up: After receiving guidance, provide feedback on how their advice benefited you and continue to nurture the relationship over time. This is really legend-level stuff right here. An extremely small percentage of people close the loop.

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Marinade

Recently, I mentioned my current favorite newsletter, Growth in Reverse by Chenell Basilio. After doing a little binge-reading on a recent plane ride, it deserves a better callout. Chenell reverse engineers and breaks down the growth strategies of brilliant creators.

Some recent faves:

• How Heather Heather Cox Richardson, a professor of American History, is making 12 million off a niche newsletter

• How David Perell Built an Email List Worth 8-Figures

• Sahil Bloom: The Road to 400k Subscribers in 36 Months

I highly recommend you give it a read. Tactical insights are the 🐝🐝 knees.

Onward,

April

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