How to Ask for Things

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If there was one skill I’d want to impart to my future kids, it would be how to ask for things.

My career is essentially a succession of asking for things: asking someone for a job, to work for me, for money, to do something for me, or even for an introduction to someone else. There are probably dozens of other examples.

Despite it sounding simple, I think it’s quite a difficult skill to master, so I wanted to give you my personal guide with a few anecdotes to help you.

I’ve broken this guide into four parts:

1. Considerations before Asking

2. How to Ask Effectively

3. Asking for Introductions

4. How to Handle Rejection

Considerations before Asking

These are things I wanted to make very clear before you ask for things.

No one is obligated to help you or answer your ask

I’ve always set the expectations for asks very low. Expecting someone to say yes or to help you will just set you up for disappointment and put undue stress on your relationship.

I also feel that the strength of your relationship shouldn’t play a big factor in this. For example, one of my best friends was getting married in Europe and asked if my wife and I could attend. In my head, it was a no-brainer; we were going to attend. However, she shouldn’t expect us to come or get frustrated if we couldn’t make it since it’s an expensive trip from Australia.

The best approach here is asking if I could make it but reassuring me that it’s understandable if I couldn’t make it or if it was too much money. Ensuring the other person feels comfortable saying no is just as important as making the ask.

Holding your relationship ransom for the ask is a terrible way to approach things.

Make your gratitude and appreciation loud and clear

Expectations can also cause less appreciation from the ‘asking’ party and potentially slight resentment from the ‘asked’ party.

For example, if my wife drives us somewhere and she does it 10 times in a row, then it becomes the norm or expectation. It can cause me to become complacent and her to get resentful. This is why, even though it’s my wife, I try not to set expectations and show gratitude when she offers to drive. Small things make a difference!

Is there an assumed ask you make every day that you could show more gratitude for?

Trust me—no acknowledgment or gratitude can eventually wear down a relationship. No one will get sick of hearing praise from you, but the opposite can have a negative impact.

Don’t assume rejection

I believe many people don’t ask for things enough. If you compare a salesperson who asks for a sale 100 times a day versus a salesperson who asks for a sale once a day, their results will be night and day.

If you apply that logic to everyday life, what would happen if you asked for things 10 times more? Would your surface area for luck also increase 10 times more? Most likely, yes.

Perhaps you don’t apply for a job because you assume you won’t get it. You are most likely making hundreds of these assumptions every day for dating, jobs, introductions, and more.

Don’t assume rejection—just ask!

How to Ask Effectively

Now that we’ve covered some important considerations, let’s think about how to ask for things. Here is a bit of a formula that I use for asking, especially for a ‘cold ask’—i.e., asking someone for something when you don’t have a relationship already.

{ Buy In }
{ Introduction }
{ Ask }

Just these three parts will make your ask stronger and more effective. Let’s discuss the “Buy In.”

In marketing, you may be familiar with the ‘hook,’ which captures attention. This is the same in making an ask, as you want the person to get interested in helping you.

There are a few buy-in types you could use:

• Commonality → Perhaps you went to the same school as someone or share similar interests. Use this to get them interested in you as a person. Do they play Baldur's Gate 3? Maybe ask them if they have done a Dark Urge play through. Do they watch Korean dramas? Give them a recommendation.

• Interesting Project → Are you doing something interesting? If so, maybe lead with that. For the longest time, when I reached out to people, I would tell them about the great work EntryLevel was doing. It was unique and cool enough that people usually replied!

• WIIFM (What’s In it for me) → What does your ask give the other person? If you’re asking for a partnership, how does it benefit the other party?

Next is the Introduction, which is just a quick summary of who you are, your company, or anything else that might be relevant. Remember to keep the entire ask very short. Ideally, this is just one sentence and straight to the point.

Finally, the ask should consider the level of time or commitment you think the person would be willing to give. Typically, with someone busy, if you ask them for a dinner off the bat, that is a little too intense. I would suggest, for the most part (unless, for example, you want to hang out with a fellow student), you should ask for a 10 to 20-minute phone call. If your ask is compelling enough, a 10-minute phone call should be easy to accommodate.

When asking people you know, it’s still important to be clear with your ask and give them a good reason to do it.

Here are real examples from me: (Green → Buy In, Blue → Intro, Pink → Ask)

Hey Austin! I love the work you do in education - we do similar work but in Australia and just did a cohort of 5000 people last month. I’m Ajay from EntryLevel - we do cohort based tech courses but at high volumes of thousands at a time. Would love to chat for 30 minutes next week to discuss collaboration opportunities.

Hey Greg! I’ve run marketing for a firm down the road from you. You have seen our cool mail campaign in your mailbox! My name is Ajay and I’m a 4th year physics student who is doing marketing (weird I know! but I like the math aspect of growing companies). I’m looking for an internship in the marketing space and I really like what you guys do! I saw the latest ad iteration on Facebook and I thought it was a smart idea. Would you have time for a 10-minute chat?

Psst. Curious about how to ask for mentorship? Read more here.

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Asking for Introductions - The ‘Double Opt-in’

When asking someone for an introduction, remember that the person on the other end is welcome to decline. They are not obligated to meet with you, and coming in with expectations can sour relationships.

Here are some considerations:

• When you ask for an introduction, typically, the middleman will ask the ‘asked’ party if they would like to meet without making the introduction. If the other person agrees, then the introduction is made.

• If the other person doesn’t want to meet, don’t take it personally. Everyone is entitled to their time as much as the next person. This has happened to me many times, but you just have to move on. For every rejection, there are probably dozens of people who would love to meet you.

The optimal way to ask for an introduction is the forwardable email. It creates a ‘double opt-in’ so both parties agree to meet before the middleman makes an introduction.

You should also always do this if you are the middleman!

You send an email to the person you want an introduction from and use a similar template to the above section. However, you would say, “Hey, I would love to meet person X,” then have the buy-in, introduction, and ask, which would be a meeting. That person can forward it to the recipient with a simple “Hey, do you want to meet this person?”

It keeps the effort low for the middleman and makes them more willing to make the introduction. They can also assess your email and pre-qualify it for the other party.

Remember, making a bad introduction does have a poor reflection on the middleman, so they also want to ensure they aren’t making bad introductions.

When I act as a middleman, forwardable emails make my life easy and ensure I keep a very high quality of introductions. People know when I make an introduction, they can expect a certain level of trustworthiness or quality.

Even when I meet someone who is absolutely amazing, wealthy, and successful, I would still ask people if they want to meet this person. Even if I’m 99% sure they would love to meet, asking is a mandatory courtesy in my opinion. Also, the act of saying “yes, I would like the introduction” helps them buy into the introduction even more. It gives the other person more control, which is also helpful from a psychological perspective.

Also, my final note is, introductions RARELY work if there are 2 middlemen. Because no one party has an interest in making that meeting happen. Introduction only work well when the middleman knows BOTH parties.

Psst. Need help with networking? Click here for more tips.

How to handle Rejection

I always try to expect rejection. I’d aim for success and keep persisting in the face of adversity, but keeping expectations low and not pushing things too much is a good way to approach it.

With that said, it can be tough. If you really wanted to meet someone or wanted a job, it can be soul-crushing when it doesn’t come through. My honest advice here would be to just get more reps in. When you send 100 emails and get 10 rejections and 10 successes, it’s less soul-crushing than 1 email and 1 rejection. You also become less hung up on a specific email or ask.

Oh, and don’t dwell on rejections—get your mind off it, go for a walk. I’ve spent way too much time worrying about rejections that days, weeks, or months later I’ve totally forgotten about.

There you have it—the guide that I will share with my future kids and help all of you in the meantime. This is the most important skill, in my opinion, so go out there and make 100 asks and get rejected more! (So you get used to it!)

I promise, you will see more opportunities coming your way just by asking more.

Good luck and until next time!

Ajay