How to Make Requests That Don’t Frustrate People

Get to the point quickly - Issue #106

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I was talking with a client recently about how to send emails to potential advisors, investors, etc. I think the natural tendency is to lead up to the “ask” because you are nervous about asking someone for their money, time, or connections.

You feel like you have to tell the story and persuasively make your points before you ask them for something. It’s normal to feel that way. I’ve especially noticed this with phone conversations.

Many people also behave like that in person too. They make a lot of small talk before getting around to the real point of the conversation.

But, written communication is a bit different. You want to share important information in the first few sentences.

Then, you can add other details. Finally, you may follow that with extra background information. Journalists call this the “inverted pyramid” model.


Everyone is busy

I would imagine that the people you plan on contacting are very busy. Aren’t we all?

The average businessperson receives over 130 emails per day. If they can’t quickly figure out what someone wants, they move on. They will probably never make it back to your email.

Almost every business-related message has an ask of some type (i.e., the request).

Even if you are only requesting a call or meeting, they will want to know why you want that call or meeting. Real-time conversations consume precious time, and we are all protective of that.


What is your ask?

Messages tend to ask for one or more of four things:

  1. Money (e.g., Will you invest, donate, buy, loan?)

  2. Time (e.g., Can you meet with me, give me feedback or advice, attend an event?)

  3. Networking (e.g., Can you introduce me to someone?)

  4. Reputation (e.g., Can I use you as a reference?)

The recipient already knows that you want something, so it’s best to be clear and upfront with how you think they can help you.

Put the request in the first sentence or two.

Be very specific with how you think they can help (e.g., an introduction, a donation, an investment, etc.).

This isn’t the time to be coy.


Rough outline for your message

  1. Who you are and your one-line pitch. Make it intriguing enough to keep them reading.

  2. What your specific request is (e.g., money, time, network, reputation)

  3. One to three short bullet points to support your request (e.g., why it matters, why they should care, what’s in it for them)

  4. What you are specifically doing or creating that requires this request (e.g., your startup, your cause, your job search)

  5. Briefly repeat the request with how you think THEY specifically can help (why did you choose them?)

  6. Thank them, and close with easy ways to contact you

That’s it.

Keep it short, simple, and to the point.


Don’t frustrate someone when you need their help

It’s frustrating to receive a fuzzy email where you can’t figure out what the person really wants.

It’s also frustrating to receive a vague invitation to talk or meet (“Hey buddy, let’s get coffee!”). You already know that the person is going to make some other request in that later meeting.

Just tell me what you want now. I’ll decide if it’s worth my time to take a call or meet with you.

When you are direct, it shows respect for me and my time. It saves you time and energy, as well.

Are there any other tips or techniques that have worked well for you?


Do the following Career Tips interest you?

  • Why you have to change your environment to be successful with any personal or professional goals.

  • Why you can’t let guilt hold you back in your career pursuits.

  • How you can tell when a layoff is going to happen at your company.

  • How to secure the training and education you want this year.

Upgrade to the paid subscription for this newsletter and receive more quick career tips during the week! 


What I’ve been reading and writing

  • I wrote about my experiences with layoffs in Silicon Valley in How to Tell When a Layoff is Coming. My list of ten clues will tell you if the executives at your company might be planning a layoff. Recognize the warning signs, and you can prepare yourself ahead of time!

  • In Will This Be the Year That You Quit Your Job?, I shared a framework for deciding if you should stay or go. Perhaps you’ve endured too much conflict with your boss. Or, you’re tired of working with negative coworkers in a toxic workplace. You can’t imagine spending another year dealing with any of this. But, you don’t know if long-term career success will be more likely if you stay vs. quit.

  • In Why Remote Work is Eating the World, Chris Herd suggests that “Remote working will continue to explode as more people want to operate remotely and more jobs are able to be done that way. Tools that enable this will accelerate this transition and within 20 years the majority of people will be remote workers.” Big corporate campuses are going to die out; they just don’t realize it yet.