How to Ask for Advice and Get People to Commit the Time to Answer
Apparently, this doesn’t just happen in cartoons.
People often ask me for advice on fundraising, generating deal flow, hiring, increasing visibility, triathlons, babies, etc.--a really wide range of stuff. This post isn’t meant as a criticism of anyone for doing so. It’s just meant to share some transparency around how to best get me and, I think, others to engage.
As is the case with any major company, career, or life function, the breadth of information one could pass along in each of these areas could fill a book.
That means that a chat over coffee or a phone call is going to deliver a largely incomplete picture of how to master any of these areas. As the person giving the advice, doing a half-assed job of getting someone all the information they need is pretty unsatisfying—so that becomes a barrier to wanting to do it at all.
At the same time, it's much more rewarding to share advice with someone who gives off the kind of signals that they're going to make the most of it. In my experience, that often correlates highly to people who have done a lot of work before they've come to me, as opposed to starting with me to get the basics.
Not only does showing what you’ve done so far help me trust you're going to follow up on all the homework I give you during our meeting, but starting with the very basics is kind of a waste when you’re making an ask of someone experienced. You could find amazing primers on Medium or great starter videos on Youtube that could shift the focus of our discussion to some very specific and advanced advice tailor-made for your situation.
You never want to hear, “I haven’t started yet” when your response to their “How do you find X?” question is “Have you tried Y?”
Also, consider the exchange of value when you ask for someone's time.
Everyone has a bar when it comes to how valuable they consider their time as well as some way to objectively measure the utility of being helpful. Being a helpful person to one other person feels good, but being a helpful person in a way that you uniquely can be helpful feels even better.
It's like, "Wow, am I so glad you came to me because I have a really good answer for this!"
I feel that way when someone asks me to point out the sights in Brooklyn Heights and I get to tell them that 58 Joralemon Street is not a real building.
This works in quantities as well. That's why I'm always giving talks to students or to groups of newbie founders. Sure, their questions might be pretty basic, but when there are a lot of eager faces in the room, the little bit of basic startup knowledge you're passing on to each one gets multiplied across the whole group.
When you’re asking for a one-on-one, you want the other person to feel like this is going to be a thoughtful and interesting exchange with someone who has already done a bunch of work before they’ve gotten to you. They’ve exhausted all the ways they could simply Google, Tweet, or post asks on LinkedIn for the information, and put most or all of those things into practice.
Now they’re coming to you with thoughtful and specific questions about the ways they’ve gotten stuck, what didn’t work, or the conflicting advice they’ve received from online searches (one of my favorite things to opine on).
At that point, I’m going to be way more excited to engage.
The other thing I would suggest is getting some of your questions out in the intro e-mail—because the reality is that we all have limited time, and especially if I don’t know you, I may not be able to carve a synchronous meeting out of my “regular business hours” time. That being said, I’ve been known to respond back with some epically useful thoughts that I’ve written in pieces throughout the day between meetings or at 1AM when my brain decides, “This is a great time to work efficiently!”
This also allows us to build a relationship. Maybe the first time you ask something thoughtful, I’ll send a few thoughts over by e-mail, but our connection doesn’t have to stop there. Next time, you might comment on a blog post and the time after that, I might see you IRL on a panel—turning you into a real three-dimensional person in my mind instead of just an e-mail address or a talking head in a Zoom room. Too many times, I’ve engaged with someone, given them some good advice, and the relationship just ends there. They don’t wind up subscribing to anything I put out there and I never hear from them when I have a random ask for a kayaking volunteer or a recommendation on a space to host events in NYC.
Allowing for different forms of answering your questions gives me some confidence that you understand something about human relationships, how to invest and nurture them, and that this ideally is a long-term build-up.
At the end of the day, I and other people really do like being helpful, but those of us with some visibility too often find ourselves on the short end of the stick—brain sucked on a drive-by with very little follow-up on whether they took the advice, if they found it useful, or whether anything came out of it.
And no, just putting me on your company’s mass update e-mail isn’t relationship-building.
Last thing—this is why podcasts and other types of live interviews are such great hacks for learning the basics of new things. Instead of asking me how to find LPs for a venture fund, do a video interview with me about it that I can post to all my channels. This way, I have something to point to every time anyone else asks me for the same thing and you’ve also done me the favor of being an outsourced content editor. Having a following requires continuously feeding the beast, so when you interview me, you do me a favor by doing all the hard work of putting something together to give to them.
