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How to Make a Big Cold Email Ask When You Aren’t Offering Much Value

I won’t say cold email is ever necessarily easy — but it’s easier if you have something that’s obviously valuable to your recipient and explicitly solves their pressing problem.

So… what do you do when your cold email “ask” is much bigger than what you can offer?

For example:

  • Link building
  • Pitching guest posts to websites that are more prominent/bigger names than your own
  • Reaching out to high-profile podcast guests or potential collaborators
  • Cold email requests in academia, like emailing a professor
  • Outreach to people to try your untested or unproven app/service/business

In all of those cases, you’re asking for more than you’re giving. It’s almost like you’re asking a stranger for a favor, largely out of the kindness of their heart.

Again, cold email is hard enough when you’re offering major value. So when you’re offering negative value? Oof.

Fortunately, though the process is difficult, it’s not impossible.

Here are five strategies you can use when you’re sending a cold email pitch where your big “ask” outweighs what you’re offering in return.

The Big Cold Email Ask: Table of Contents

5 Strategies for Cold Email When Your Ask Outweighs Your Offer

Here are suggestions for proven cold email strategies you can employ in your big “ask” outreach messages.

1. Reference your shared background (especially the same alma mater)

You and your prospect may not know each other personally. It’s likely you’ve never met.

But if you have a shared connection — like you grew up in the same hometown, you went to the same college, or you have a mutual friend — lead with that.

Make sure it’s a good shared connection — do not follow George’s advice from Seinfeld.

Jerry: “Check these out. These are Jerry Lewis’s old cufflinks that he actually wore in the movie Cinderfella. I got them at an auction.”

George: “I got some cufflinks I could’ve loaned you.”

Jerry: “No, Jerry Lewis is gonna be at this Friars Club roast I’m going to next week. Now I have an ‘in’ to strike up a conversation with him.”

George: “You already have an ‘in.’ You have the same first name. Jerry.”

You need a stronger "in" to make a big request

Via: GetYarn.

There’s something in our tribal cave brains that makes us want to help people with whom we share connections. Might as well capitalize on that.

One alternative: If you went to a rival school, you could bring that up as well. I’ve even seen a cold email where someone proposed a bet on an upcoming football game. If their school won, the person they reached out to would agree to have coffee.

Example of referencing your shared background

Subject: Quick question from fellow UT alum

Message: Hello!

My name is Ferris and I’m a fellow UT alum (‘04, lived in the Stacks in the glory days before they turned the lawn into a parking lot).

Anyway, I’m the host of X. We just hit 75 episodes and we’ve had guests including Y and Z. So I’m finally confident to reach out to you about coming on the show. We could talk about A, B, or, if you have anything else in the works, that as well.

Please let me know if you’re interested!


Template for reaching out when you have a shared background

Things to note in this template

  • I put our shared background in the subject line. I figured it was my best shot at getting the open.
  • Notice in the opening line I didn’t just mention we were both alums from the same school, I made a friendly reference to evoke some nostalgia in the recipient.
  • I pumped up the recipient’s ego.
  • I made it clear I had some social proof (75 episodes, other named guests) so I wasn’t asking this person to come on a brand new, no-name podcast.

2. Become an active fan before you reach out

If you’re reaching out to giant celebrities with giant followings, they might not notice you liking all their posts, making high-value comments on those posts, leaving a review about their product, or rising up the ranks of your newsletter referral program.

But everyone else, even one tier down from giant celebrities, will notice when the same name keeps popping up over and over. And those highly-engaged fans’ names become embedded in their brains.

So if you’re an active fan for a month or two (or longer) before you reach out, it makes your cold outreach slightly warmer — and makes it feel like less of an imposition.

More advice: Continue to stay as active after you make the ask, even if they don’t write back. Every time your name pops up it will be a little guilt-inducing reminder for them to write back to you and makes it more and more likely they’ll eventually respond.

Example of reaching out as an active fan

Subject: Quick question from Ferris (@ferrisp on Instagram)

Message: Hello!

My name is Ferris. I’m a big fan of your work (you may have seen @ferrisp in the comments on pretty much everything you post on IG).

I was wondering if you could do me the hugest favor. It’s my wife’s birthday next week and she also loves your stuff. Would you be willing to send a quick video wishing her a happy birthday? Her name is Anita. And her favorite book of yours is Love and Other Mysteries.

Please do NOT send the video if it slows you down even 20 seconds on writing the sequel.


Template for reaching out when you're an active fan

Things to note in this template

  • I included my username in the subject line, hoping they’d recognize it then open the email.
  • I then opened the email again referencing my activity on their accounts.
  • I jumped right into asking the favor, keeping the “ask” reasonable from a time commitment standpoint.
  • I made the last line a joke that, again, shows I’m a big fan and hopefully breaks down their defenses so they do the favor.

3. Give legitimate, personal insight into their work, company, or product

Cold emails that open with flimsy, generic praise almost never work — especially in a case where your ask outweighs your offer.

But real insight that shows you’ve actually read, processed, and given serious thought to someone’s work? Real experiences as a power user of someone’s software product? Being a paying customer of someone’s company?

Those show you aren’t sending a generic mass email — you’re sending them a cold message specifically because you’re actually invested in what they do.

And that’s going to pique their interest and make them more likely to hear you out.

Example of giving legitimate, personal insight

Subject: My 3 best pieces of feedback about MoneySoft (+1 quick question)

Message: Hello!

My name is Ferris. I’ve been on the MoneySoft premium plan since October and it’s become a huge part of my daily workflow.

I wanted to share my feedback (plus one question)…

  1. I absolutely love the ability to turn any action into a recurring automation. The more powerful you can make this feature, the better.
  2. It would be great if there were a faster way to get info onto the platform from my phone. Email-to-task, mobile Safari extension, anything!
  3. As a power user I lean on keyboard shortcuts. But there aren’t shortcuts for changing the recurrence of a task or text formatting inside of cards.

And one question: I am a freelance writer in the SaaS space (here’s my portfolio). I would absolutely love to write a post sharing some of my tricks for getting the most out of MoneySoft for your blog. Is that something you’d be interested in?


Template for reaching out when you have legitimate interest

Things to note in this template

  • I made it clear I’m a paying user and I’m invested in their product.
  • I am trying to offer real value to the company here in terms of feedback. That value does not outweigh what I’m asking for, but at least I’m giving something.
  • I’m really trying not to ambush them with my request — which would make all of the other stuff in this email seem like it’s in bad faith. That’s why I mention in the subject line and before I give the feedback that I have a question for them. I wanted to prime them mentally to expect my request.
  • I didn’t ask for money; it’s implied I’d do this job for free. If I do a good job, this post could lead to paid work with them in the future. And even if it doesn’t, it’s a strong portfolio piece and backlink for me.

4. Make a good joke based on their biographical info

Odds are your prospect has put out some funny bit of information somewhere — whether it’s in their on-site bio or their social media accounts. If you can reference a deep cut and make a good joke about it, you’ll stand out.

I’ve mentioned this in blog posts before, but here at GMass, we all put a few jokes into our bios on the About Us page. That was by design. I put those in there so savvy cold emailers could use them as icebreakers when they reached out to us.

So far, only one person has; she referenced the movie I cited as my “Shameful Love.” She made a good joke about also being a fan of Miss Congeniality 2: Armed & Fabulous which caught my eye and showed me she’d researched me and put some thought into her message. And even though I wasn’t looking for the service she was offering at the time, she’s on my short list to contact when that day arrives.

Example of making a good joke based on someone’s biographical info

Subject: Quick question (and a 2nd quick question, about The Waterboy)

Message: Hello!

I’m Ferris and I’m reaching out to a few websites to see if they’d be interested in adding a link to the Greatest Thing I’ve Ever Written to one of their blog posts. (It’s this article, by the way, about 15 different ways to make chocolate-covered vegetables.)

But we have something more important to talk about. I was scrolling through your Twitter and saw your impassioned defense of The Waterboy as Adam Sandler’s best movie. It’s controversial — I’ve always leaned Billy Madison and thought he went a half-step too over-the-top in Waterboy  — but I get where you’re coming from. At least you’re not one of those “he’s actually a really good actor have you seen Uncut Gems” people. Thank you.

Anyway, let me know if you like my link and you might want to add it or if you want to switch to Will Ferrell and argue about why Talladega Nights is better than Old School.


Template for reaching out with a good joke

Things to note in this template

  • I took a very, very casual approach here. I intentionally almost brush off my request to get to all the funny banter about their biographical info.
  • I spent the majority of the email on the joke, not my request. I’m trying to pattern interrupt with that technique. I’m sure this person gets plenty of cold email requests. I doubt any have engaged them like mine. Which, I’m hoping, will make them more likely to do me the favor I’m asking.
  • By the end, I’m hoping they think of me almost as a friend or peer, making them more likely to write back. And when they write back to banter… they’ll also have to address my request.
  • Even if this doesn’t lead to the link, it could be a networking opportunity and establishing a rapport with this contact.

5. Offer some kind of ancillary value

Your cold email offer might not be great. It might be terrible. But there’s probably something of value you can offer.

One approach I’ve seen a handful of times is the coffee offer. Instead of asking someone to meet you at a coffee shop, you do the Zoom-era equivalent: You offer to buy them a coffee during their meeting with you. (Send it via a delivery app, send a coffee gift card, even mail them a bag of coffee grounds — any of these can work.)

Another approach I’ve seen is link builders offering social or newsletter promotion. If you add a link to their site, they’ll promote your article to their n number of subscribers or followers.

What you’re doing here is finding a way to offer something of value, even if it’s not directly related to your offer itself. You’re trying to solve a different problem or, in lieu of that, at least showing you’re not asking for someone’s time for free.

And by finding another means of providing value, you’re re-balancing the cold email equation to make a prospect more likely to respond favorably.

Example of an ancillary value add

Subject: Quick question

Message: Hello!

My name is Ferris and I’m a graduate student at the X. I am currently writing a paper on Y and after reading your research on Z I would love to get your insight on the topic.

Would you be available to do a 20-minute video chat with me sometime in the next few weeks? Normally I’d ask to meet for coffee, but since we’re 2,156 miles apart, I’d love to do the next best thing: Postmates some coffee to you (maybe from Beanz on Main)?

Please let me know if you can fit me into your schedule or if you have any other questions.

Thank you,


Template for reaching out when you can offer ancillary value

Things to note in the template

  • I went back and forth on my subject line quite a bit. Ultimately, I couldn’t find a succinct way to bring my request, the coffee, or both into the subject. So I went with the more generic but (at least for now) still somewhat effective: “Quick question.”
  • Though I didn’t do it in this message, this would be another situation where offering a piece of unique insight into the recipient’s research would be ideal personalization.
  • I cited a specific coffee shop near their campus to make it clear I’m dead serious about the coffee delivery idea.
  • I would only send this message to one person in a department at a university at a time. Colleagues talk.

Using GMass to Send Your Cold Email

Once you figure out the strategy you’re going to use to send this “ask” email, you’ll need a way to send the message.

And sure, you could fire off a single message from your email account. But if you’re looking for a more thorough and effective means of sending cold emails, you should take a serious look at GMass.

Here’s how GMass can help you send your big “ask” emails to maximize your odds of getting a reply.

Advanced mail merge personalization

You may be sending a single cold email to a single recipient. But there’s also a good chance you’re planning to send your message to several recipients.

With GMass’s advanced Gmail mail merge personalization you can send your cold emails at scale and make them look indistinguishable from one-on-one messages.

You can use GMass to send individual, personalized messages to everyone on your outreach list. And you can customize more than things like name, company, and website. You can send personalized links, images, attachments, or even entire paragraphs.

Using mail merge in GMass

With GMass you can also use fallback values in case you don’t have merge data for various recipients.

Fallback values in GMass

Another unique feature: If you’re sending your emails to people you’ve corresponded with in the past, GMass can send your messages as replies to your last email with each person. That’s another way to really sell that these are one-on-one messages.

Spam Solver

Deliverability is a big deal for all cold email senders. GMass has a variety of helpful deliverability tools for cold email campaigns like custom tracking domains with SSL and email address validation.

For your campaign, Spam Solver can be a huge asset. Before you send your message, test it using GMass’s Spam Solver tool.

GMass's Spam Solver

It will assess whether your message is destined for the inbox or spam folder. And if the verdict is “spam,” Spam Solver will give you suggestions to land in the inbox. Then you can re-test to see if those tweaks make a difference.

Auto follow-ups

Persistence is important when you’re reaching out for favors. It’s unlikely that your recipients will move your email to the top of their priority list — and it’s entirely possible they’ll forget all about it.

You’ll need to assess how persistent you can be without burning the bridge. But at least one, and maybe two or even three, follow-ups could greatly increase your odds of getting a response.

It’s super easy to set up auto follow-ups with GMass. You can decide how long you want to wait between each follow-up and what trigger should stop the emails (for instance, end the sequence when the person responds).

Auto follow-ups in GMass


There’s nothing quite like putting yourself out there with a big “ask” in an email… then never knowing if the person has even read it.

With GMass you can track your email, even if you’re just sending to one person.

Reporting in GMass

Track whether they opened it, clicked a link, or replied. Take some of the mystery out of the cold email send-and-wait process.

The Big Cold Email Ask: Takeaways and Next Steps

A traditional cold email offers significant value to a recipient. But not every outreach message has a ton of value to offer — there are scenarios where what you’re asking for is a lot bigger than what you have to give.

So what do you do in those situations? Here are some approaches you can take to improve your success rate:

  • Reference your shared background with the recipient, like the same hometown or school
  • Become an active fan to catch their eye before you reach out
  • Give legitimate, personal insight into their work, company, or product
  • Make a good joke based on their biographical info
  • Offer some kind of ancillary value

While your response rate may still not be quite as good as you’d get from a strong offer, these techniques will help improve your odds on favor-focused cold emails.

And regardless of which approach you take, GMass is a great way to improve your cold email outreach.

GMass works directly inside Gmail, so there’s no new platform to learn. You can get started on a free trial by downloading the Chrome extension — no credit card required. Then you can use GMass to send up to 50 emails a day during your trial before you upgrade to a paid plan.

See why GMass has 300k+ users and 7,500+ 5-star reviews

Email marketing. Cold email. Mail merge. Avoid the spam folder. Easy to learn and use. All inside Gmail.


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