How to better your ask to get more helpful responses

Do you ever struggle getting help or even more, simply getting a response sometimes? I have lost way too much sleep boiling over the lack of response to an ask with all kinds of crazy thoughts racing through my head. Sometimes it starts with, “don’t these people check their email” and quickly spirals into suspicion, conspiracy theory, and beyond. What I have learned in the last twenty years is that the problem isn’t usually them… very often it has been me.

Part of my life was before the internet and the other part wasn’t. That’s a pretty big deal. Some people say it has changed the world. One thing I know for sure, the number of requests fired across the universe is now like sand on the seashore. We used to get a few calls a day to a single phone in the house with a spinny dial. Now… how many texts, emails, push notifications, questions, suggestions, assignments are you getting each day? Case in point… We are all inundated with “asks” every day. On one level, we are doing well to identify those messages and notifications that represent the ticking time bombs in our personal universe. Then there is that layer which is what we HAVE to get done each day… personally and professionally in order for life to keep rolling on. Finally, there are all those things in our inbox that are interesting to us, that we really want to accomplish one day when all of the notifications finally slow down (smh!).

Most of us generally are or want to be good people. We want to live a life that involves caring for and helping others at least a little bit. Each day, we get a request from someone else that we really want to respond to… even if there is a price to pay to do so. We care about these people, the cause or result matters to us, etc. We all probably get more than one. But we only get 24 hours in a day and can only do so much. So, who do we help and why? Well maybe it’s our boss and the answer is obvious but maybe not… how much of the why has to do with the ask itself? Here’s what I’ve found:

1. I am the one who needs something

We need to realize that just because we live in America and believe that the customer is always right doesn’t mean we are. I’ve needed to remind myself many times that I am the one with the problem not this person. I am the one who needs help and who is inconveniencing this other person. I need this person to stop doing things they care about and do what I care about. When we understand things in this light, our attitude shifts positively in the right direction. It starts to feel a little right to feel kind of sympathetic and bad for this person, right? Good. That’s better usually.

2. This response matters to me

I have noticed that when I REALLY need something and/or the response I am looking for matters to me, everything about the ask changes. By this I mean, I spend a lot of time working on my ask. I write and proofread it several times. I make it as easy as I can for this recipient to answer me… even to answer me ‘no’ when the ‘no’ itself is valuable to me.

I have now also begun to see this in the ‘asks’ that come to me. “Hey [person], we should get together sometime.” How many times have we said this? We mean well but it usually doesn’t happen. We genuinely like the person and want to see them again… but we are actually not that serious about it. When we are serious, we say things like, “hey, when can we do this again? I’ll be free on…”

Remember: Your ask communicates how much the response matters to you. Let’s think about that a little.

3. Detail matters

When the response matters to me, I think about the details. Why?

When this person opens my email and while I have their attention I need to make sure I have everything needed so this person can respond accurately the first time. How many times have you gotten an email that says something like, “when you get a chance can you tell me what you think about [insert not attached or linked to email thing here].” If we want someone to do something for us, we need to make sure they have everything they need to get the job done. It’s better to assume we’ll only get one shot at this and our audience must have everything they need to help us on their first pass. If one must take additional steps, email us back for something, or work hard to find something then let’s assume we failed. Again, when it matters to us, we do these things before we click send. Remember, we are inconveniencing this person and we want to make this as easy and painless as possible to help us…


  • “Hey, if this link doesn’t work… here are some screenshots or a PDF of the same thing.”
  • “I’ve included a map PDF and a link to it on Google maps… and Apple Maps.”
  • “Here is a link to the article I found about this topic.”
  • “Here is the phone number you’ll need.”

4. Supporting information matters

Software engineering is helping me a lot in this area. If you are describing a problem, I’ve found this to be very helpful:

  • Say what you are trying to do (i.e. the big picture)
    • “I want this button to save this information and the user to see this message”
  • Say exactly what happens wrongly carefully
    • “The page does not redirect, and I get this error message. Bonus points… Here’s a screenshot”
  • Say what you expect or want to happen
  • Detail what you have tried already
  • More extra credit: “I googled it and these two links to results were the most helpful…”
  • Include a picture
    • pro tip: your phone probably lets you mark that image up with arrows, circles, etc to really show me what you’re talking about

5. Timing matters

In this day and age, it’s so easy to fire off a request into the internet ether any time of day and assume our target will see this at a good time. If we are wise, we may at least think about who we are asking and what their life is like especially if the response matters a lot to us. My kids are learning not to ask me anything until I have had some coffee in the morning. But also, not while I’m in the middle of something.

I am reminded of a case where I found out the name of a person who had first-hand knowledge of something in my family history that I wanted to know about. I wanted to contact him immediately but was told that his wife had just passed. It wasn’t the time to ask him to do something for me. I think we all get the picture.

When you are sending your ask over the internet:

  • Will this person get a notification that wakes them up?
  • Consider the medium and internet etiquette and ask correctly.
  • Is a text message really the best way?

6. In person is better

Speaking of the ether, requests that appear out of the ether are easier to dismiss. It’s just a fact. Sometimes messages really matter to us but by the time we collapse after putting three kids to bed, we just forget to go back and respond to that text message even though we really meant to.

If it really matters to us, we probably find a way to go visit the person from whom we need help. Where it is possible, consider doing this. Again, because the response matters to us let’s take some time to consider the other person, how much time they have, what we want to say, etc.

7. Demonstrate that you have already tried some things

  • If you haven’t even tried to solve the problem yourself, it’s pretty hard to respond. Some people are of the ilk that it’s bad for you to reward such behavior and thus encourage more of it.
  • Did you Google it? I hope so. It’s better to do that before you ask. If you did, mention it and a little about what you found.

8. Clarity

Much of the time, when something is really important to me, I find it is really hard to ask. I get anxious. In fact, for most of us it’s hard to ask for and even to need help. I think this is part of what it means to be human. We all need help and must come to grips with that somehow. I think this is good for us actually and represents some type of growth. Anyhow, due to this I find it is hard to speak about my need or communicate clearly. This has also made me difficult to help. Many times, a helper has had to ask me what it was I really wanted or needed.

So, my learning has been to get really good at boiling it down, crystallizing, and clarifying (firstly in spoken word even to myself) what it is that I want or at least think I need. This will help people help us. A number of times, someone tried to help me while misunderstanding my poorly crafted ask and spent a lot of time, energy, and even money doing something I didn’t really want or need. I felt pretty bad about that.

9. Give and take

It’s easy to understand this with a commercial mind and end up playing tit for tat politics. I am not promoting that. I am rather promoting the principle that one reaps what he sows. This comes from a Bible verse (Gal. 6:7-9) which says, that whatever a man sows, this also shall he reap. If we are a person who genuinely endeavors to be helpful over time, my experience is that we also reap the fruit of that tree.

This is just what I can come up with. I am sure there are many more angles I have not considered or learned yet as well as detail and nuance related to these that could be developed. I’d love to hear from you and learn together.

Please feel free to constructively contribute in the comments or email me at