If You Want A Response, Ask Specific Questions

I try to respond to all of my emails. I’ve always been like this – it’s just part of my value system. I used to be annoyed by other people who don’t, but I let go of that emotion a long time ago. But I still try to respond to all of my emails. A big hint, which is the reason for this post, is to ask specific questions if you want a real response.

Part of my morning drill is to systematically go through all the emails from the previous night. I usually end up at close to – or at – inbox zero when I finish this drill. Over the course of the week I get a little behind on non-urgent stuff so I end up responding to them over the weekend.

The result is a lot of what I like to call cliche loops. Here’s an example of the “will you look at our business, no, will you make a referral” loop.

Cliche Loop

Fortunately I use Yesware so I can respond quickly via templates I’ve already set up. Here’s how the more detailed conversation goes:

Entrepreneur: Happy New Year!  Attached is the our BP. Please let me know if you are interested to talk.

Me: Thx for reaching out again. I took a look – I don’t think it’s something we’d be into investing in but hope to run into you at anonymous-place at some point.

Entrepreneur: Thanks for the quick reply. Can we apply for the techstars?

Me: Of course!

Entrepreneur: Thanks for the advice. If you are willing, can you please comment on our BP? We wish you can be our advisor.

Me: I can’t be “an advisor” in any formal way. I’m also not part of the selection process for Techstars so I encourage you to just apply.

Entrepreneur: Thanks. We understand. You turned down our BP almost right away. So we are really appreciated if you can tell us what we can improve, or whats wrong there.

Me: I wrote a post about saying no in 60 seconds a while ago – http://www.feld.com/archives/2009/06/say-no-in-less-than-60-seconds.html. Your overview is ok – just not something I’m into.

Entrepreneur: Thanks for the detailed message. Do you have any other investors that you can point us to?

Me: Re: Asking for a referral – I wrote a blog about this a while ago – I hope it makes sense. http://www.feld.com/archives/2007/11/dont-ask-for-a-referral-if-i-say-no.html

Now, I’m not try to be an asshole with my responses. I’m just trying to get through one of “yet another email I’m not interested in” and be polite to the sender. If the entrepreneur had asked me any specific questions about his business, I would have tried to answer it or said “sorry – I have no clue” if I have no clue. But all of the questions are of the “please engage more with us” kind. Even the most specific question “So we are really appreciated if you can tell us what we can improve, or whats wrong there.” is painfully generic.

I realize that part of the reason I’m writing the book Startup Opportunities is so that I can point people like this at it. I get between one and five emails like this a day and have for a long time. I’m happy to get them – I just wish I could help more.

  • I may have mentioned this to you before, but I was shocked to find that most of the “high profile” people I’ve emailed have been extremely responsive. You are one of those people, but I could give lots of examples.

    A long time ago my dad taught me that the best way to learn anything was to ask questions.

    BTW, answering questions with a link to a blog post is not rude, it’s called working smart. Pro tip: you don’t even have to write the posts sometimes. I use one of yours all the time – http://www.feld.com/archives/2006/02/why-most-vcs-dont-sign-ndas.html

  • Brian Makare

    Good post. I’m sure when I get in a hurry, even after 30 years of experience, I still write flat, uninspiring email requests that are not specific enough. Note to self: If it’s important enough to write the email, put the time and thought into what you want from the recipient.

  • Alex Devkar

    This is very nice way of handling generic requests that hopefully pushes the requester in the right direction.

    One curious thing I’ve noticed: If you never responded at all, the requester might think: “He’s busy. He probably never saw my email.” But because you were responsive and tried to help, now you are a person that rejected the requester. That is harder to accept and often hurts feelings. In short, help -> hurt feelings most of the time.

    • Yeah – I run into this but am now immune to it. I say NO to people over and over and over again (it’s the nature of what I do) so I’m ok with being direct.

      • Glenn Whitney

        Yes- reminds me of the quip: “No good deed ever goes unpunished”…

  • The fact that you engaged in a conversation with them proves you’re not an asshole. Believe me, the fact you didn’t ignore their email puts you in a great position. And you were honest (and yes, you wrote those blog posts).

  • vimadan

    Hopefully this cuts your email clutter, but I suspect the same folks pounding your inbox haven’t bothered to read your blog. If they had they would have gone about the initial outreach very differently. Always appreciate the pro tips, thanks for sharing.

    • Truth, but that’s ok. Now I can just point them at this blog post!

  • How many of your 1-5 request like this get a response of “Yes, I’m interested” instead of a a “No”? Do the 1% of Yes’ (my guess) provide good deal flow that you would have missed otherwise?

  • Rick

    This was a good post. I think the best approach for you would be an auto-reply saying “Don’t bother me.” That sounds bad but it’s not. Think about it a bit before judging it.
    Tell us what the objective would be for us to read your book? That sounds backward but it’s a good question. I have $30 or whatever and I have to spend it wisely. So if I read your book what will it help me do? What specifically can I count on accomplishing using the information in the book? Also can I get started performing some tasks after the first chapter or will I need to read the whole book to get started applying the information in it?

    • I’d enjoy being reached out to. I don’t view it as a bother. I’m just trying to give hints about how to get something useful back from me.

      • Rick

        Set up the “Don’t bother me.” auto-responder. Then pick one email a month to be a project and help that person for the next month… Rinse and repeat.
        You have to commit to some *true action*. You’re confusing chit-chat with true action.

      • Rick

        “I’d enjoy being reached out to.”
        Brad that sentence is waking me up at night. It’s sound wrong. I’m thinking the “I’d” was suppose to be “I”. Should it be more like: I enjoy it when someone reaches out to me.
        It might just be my OCD but it’s driving me batty. Is your sentence proper or should it be stated another way?

        • It’s probably just “I enjoy…”

  • As a recent recipient of one of your very fast, polite and helpful emails, I can say that your philosophy is appreciated, Brad. You’re most certainly not an asshole.

    • Thanks Doc!

    • Hilarious compliment –
      “You’re most certainly not an asshole!”

      QoTD, but I’d agree.

      • Rereading it in a different voice, yeah, I can see why you found it funny. Kinda like telling someone “No! You’re not as ugly as a cross-eyed mule… my grandfather had a cross-eyed mule!” (not the way it was intended, though. And for the record, my grandfather had several mules, but none of them were cross-eyed.)

    • Agree!

  • Saul_Lieberman

    Brad — You don’t really explain how asking a specific question helps. I’ll guess that it gets you focused, gives you a sense that you can help and limits the effort needed to respond.
    For me, asking a specific question gives the listener something to latch onto. I tell job seekers to be specific. Being specific sounds limiting, but it is necessary to get your listener engaged and thinking. Otherwise, the listener is blocked. Once the listener is engaged, he can begin thinking of all kinds of opportunities.

    • 1. A specific question gives me something to focus on / respond to.

      2. It enables a conversation to begin. The most interesting things to me end up in multi-interaction conversations that start somewhere. The more vague the starting point, the less likely the conversation goes anywhere.

      3. The only possible way I can process as much inbound as I do and still try to touch it all is to respond to specifics.

  • Totally off-topic, but I noticed you have a small issue with the comments indicator at the top of this post, Brad. There are 9 comments, and it says 7, even though it says 9 when you mouse-over. http://i38.photobucket.com/albums/e127/dcamp2626/BradSS_zpsed48e90d.png

    • Hmmm. Weird. Will check it out. It could be a sync lag which happens sometimes with Disqus.

  • iuliana schraut

    I cannot agree more with this post. I work in an environment that requires a lot of problem solving. Can you imagine what general questions lead to? I don’t mean to offend anyone, so please forgive me if I seem harsh, but not having specific, goal oriented questions is a waste of time.
    Don’t get me wrong; I used to make the same mistake. I took Python programming at CU Boulder, and I would ask my instructor “is it right”? Or, “can I make my code better”? Finally, my instructor told me that I needed to come up with specific questions, otherwise he wouldn’t help me. Needless to say, specific questions like “I am getting so-and-so error after this cell. Can you please advise how to fix it?” helped me improve my understanding of the whole concept.
    While there aren’t (necessarily) stupid questions, asking more effective questions is the way to go. These questions ought to be goal oriented and specific. Otherwise, don’t be surprised that next time you ask for “the answer to life, to the Universe, to everything,” you get the answer “42.”

  • thanks for writing this. with our hyperconnected world, we can’t expect long thoughtful novel like responses to email. I am very interested in learning what you did with Yesware and how you set that up. I don’t have the email inbox that you have-but it’s still a task I have to accomplish. I truly am touched when people think enough to send me a personal email (not form email, trolling email or spam). I guess it comes from the days when I used to wait for the postman to arrive.

    I read the interaction thread, and I thought it was totally appropriate. Clear, concise, and understandable. Executable. What more does anyone want?

  • Three suggestions:

    1. Gmail Canned Responses (settings > labs) allows you to fully, kindly and helpfully respond to each cliche’ inquiry

    2. Within each canned response, politely direct people to relevant blog posts, FAQ, etc. Be specific that you want them to dive into these resources INSTEAD of further emails with you, unless certain conditions apply (such as a specific question).

    3. Advise that despite efforts to be polite, due to limited bandwidth you’d rather not receive a “thank you” “got it” “okay” or other needless reply.

    • Lylan Masterman

      Regarding #1, I had the same thought. Brad, why do you choose to use yesware over gmail canned responses? I don’t have a strong personal preference; just trying to understand if one technology makes this approach easier to execute than the other.

      • @lylanmasterman:disqus Yesware offers robust tracking of events like if/when opening of emails & downloading of attachments, on a freemium basis. Canned responses is free, but far less capable.

        • Lylan Masterman

          So, how might Brad have used the if/when feature to accomplish what he discusses in his blog post?

          • @lylanmasterman:disqus, Sorry I wasn’t clear. I don’t think these specifically help accomplish what’s in his post – I was just sharing reasons someone might opt for Yesware, in response to your question.

  • Neda Ghazi

    Have you seen http://mailchimp.com/ ? It seems more powerful than yasware.

    • Totally different.

  • Chris McKoy

    Brad, the example email conversations you posted had me in stitches.

  • lunarmobiscuit

    Thanks Brad, this post answered the question I sent you last month, asking how on earth you manage so much email. Is there a tool, you use to be so engaged on the Disqus comments? You do an amazing job of staying engaged here as well…

  • thanks for posting this – if only more people followed this guidance…

  • Wish I came across this post 2 years ago. While it should be common sense, I think a lot of first time entrepreneurs like myself get caught up in thinking that asking somebody to review a business plan (“because you’ll really like it!”) or value prop is an engaging question. Found out the hard way, it’s not. Especially when people like yourself see thousands of these a week.

  • Sagescript

    As someone who also tries to answer all her email I like your idea about setting up templates to use.