When Do You Respond to Unsolicited Asks?

I have always prided myself on being extremely responsive to people whether it’s on email, calls, texts or anything else. I still am very responsive to the people already in my world, but I have had to create new rules around how and whether to respond to unsolicited requests. 

I work on the theory that we are happier when we do things that have purpose and meaning and so, therefore, doing nice things for others is the right thing to do. The problem is the volume of unsolicited inbound requests has become overwhelming. I only have so much time each day and anyone asking for a meeting means there will then be another ask in the meeting itself (and if that ask requires you to ask someone else for help, then you owe that person something too and it never ends). So in order to try to find the right balance between generosity and sanity, these are my general rules for responding across a range of common scenarios:

(1). Unsolicited requests for advice from a young person. I do my best to be helpful in these cases. I can’t always and if it’s an email that seems very broad that clearly went to a lot of people, that’s different than when someone put in the effort to explain why they were seeking advice from me specifically (and let’s be honest, I have a big ego and a lot of insecurity so flattery sometimes works). What doesn’t work is asking me very general questions about my career or life that you can easily get online or from my books or columns or podcasts or anything else. So here’s a tip: be very specific in why you want someone’s advice and exactly what you’re looking for. Otherwise, it’s spam. 

(2). An unsolicited pitch. For me, these come in three forms. First and foremost are startup founders because I have a VC fund. The problem is this: if you can’t figure out how to get to me other than through a spam email, the signal you’re sending is enough – in and of itself – to likely turn me off. And so much of the time, the pitch clearly has no idea what we invest in, what we are interested in or anything that’s germane to our fund. There are now AI programs that allow founders to access the emails of lots and lots of VCs so the spam volume lately has been worse than ever, which also means that even if there is a diamond in the rough, I’m likely to miss it (also, the problem with giving someone polite feedback as to why it’s not a good fit for your fund only leads to requests to use your network to introduce them to investors who are, which means now you’re perpetuating their spam). 

Unsolicited emails also come from nonprofits seeking donations (and political candidates, whom I not only ignore completely but my outgoing voicemail message explicitly says that if you’re a candidate seeking money, do not leave a message) and from comms people looking to place someone on our podcast. I basically ignore all of them. Spam is treated like spam.

(3). LinkedIn messages. Around a decade ago, I had a LinkedIn account. I had to delete it because I was overwhelmed with requests for either help, money or advice and then I was forced to either blow someone off (which I felt bad about), say no (which I felt bad about) or say yes to something I didn’t want to do. A few years ago, we restarted my account but I don’t even know what the password is. Cory manages it. If you’re lucky enough to have someone else manage your LinkedIn for you, it’s probably worth having. But if not, the deluge of requests may outweigh the benefit. 

(4). Social media. I don’t use social media. I also don’t drink poison. Since so much of social media is designed just to get people fighting (that drives a lot more clicks, which makes the platforms a lot more money), why would I want to voluntarily read criticism from random strangers who have zero relevance to my life? And given the general nature of social, why would I voluntarily choose to bring so much negativity, toxicity and strife into my life? How does that help me? I don’t need social media to talk to my friends. That’s what text is for. To me, social media is a tree in the forest. If I don’t hear it, 99% of the time, it didn’t really happen. If you can choose to live that way, I highly recommend it. 

(5). In person. I give a lot of speeches. I teach classes. I own a bookstore that has an event space and sometimes I moderate panels or introduce authors. That all means that people are going to come up to me afterwards and ask for whatever it is they need. Once someone goes to the trouble of physically coming to see me speak, I have a very hard time not at least meeting them. And then you get pressed on the spot, which turns into giving them your email. Sometimes I then follow up on whatever they send, sometimes I realize it’s a bad idea and I don’t. But in person is a tough category to manage. 

(6). Someone you know and like. Meaning someone you’re not in regular contact with but still, you like them when you do interact with them. This one is easy. I’m very responsive to these and if I’m not, I genuinely missed it (rarely happens). 

(7). Someone you know and don’t like. I can’t tell if people who reach out to me who should have some inkling I wouldn’t want to help them have incredible chutzpah or if they’re just totally clueless. Either way, I’ve learned in these scenarios to not respond and if I really don’t want to interact with them, I’ll block them entirely (I have become very liberal around blocking people).

(8). Someone you vaguely know but are indifferent to or barely remember. These tend to fall into the know and don’t like category because if I liked and cared about this person, we’d be in touch or I’d be happy to hear from them. So if I’m not, I will typically either not respond or just say something very polite and vague. Anything more leads to an ask, a meeting or something else I won’t want to do (and keep in mind, I already have at least 5-10 meetings a week with strangers who happen to know someone I know who asked me to do the meeting). 

(9). Someone you don’t know but know of. When I get an email or text from someone I have heard of and consider to be a serious person, I will respond to it and take it seriously. But in most of those cases, there’s a third party who knows both of us and they make the intro. That’s always the better approach whenever possible. 

(10). Reporters, researchers, academics. I started my career doing political communications so I generally like talking to reporters. I am almost always responsive unless it is a far left or far right publication doing a hit piece. I also try to be helpful to researchers and academics. It partly depends what they want (my explaining a particular theory I might have around regulation and tech is very different from wanting to shadow me for a week) and partly whether I actually have anything useful to tell them (often times they think that because I invested or worked someplace I know all the palace intrigue; I usually don’t). But generally, if someone is doing research on a topic I care about, I do my best to help. 

At least for me – someone who always thinks that I owe things to people just because (am working hard in therapy on this) – absent pure spam, every time I choose not to engage with someone, there’s a pang of guilt. But every time I choose to engage with someone against my better judgment, there’s often deep regret. It’s still not easy, but setting some boundaries and sticking to them is definitely worth it.