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Curiosity vs. Ambiguity: How Cold DMs Fail

Curiosity hooks are among the most useful instruments in the marketer’s toolbox. It’s how headlines attract readers, how short-form content attracts subscribers, and how sales letters generate phone calls. But curiosity can easily devolve into its ugly cousin: ambiguity.

Curiosity vs. Ambiguity

Curiosity piques the reader’s interest and gives them a reason to keep reading. It helps ads capture more potential customers. It helps the sales collateral those potential customers read next stay engaged for longer, increasing the probability of them converting to customers. It also allows skillful copywriters to create a sense of urgency and scarcity, encouraging the readers to take action now, not later. It leads to the creation of a story loop when executed correctly, making the sales copy more memorable and persuasive.

However, when taken too far, curiosity easily turns into ambiguity.

This is a problem. Ambiguity never works… at least not in your favor. Ambiguity creates confusion, frustration and annoyance (the most dang­erous of these is confusion, because the confused mind always says “no”). Even good offers can be destroyed by ambiguity.

For example, I received a DM on Twitter a few weeks ago from someone I didn’t know, and who didn’t follow me. (Pro tip, I’m almost guaranteed not to respond to a DM from someone who doesn’t follow me. I haven’t done any research on the subject, but I’d wager most other people are of a similar disposition.) The DM was exceedingly ambiguous; the author told me he had “an idea that could be of use” to me, and then asked me if he could send it over as “free value.”

I ignored this offer for three weeks until I decided to use it for the purpose of this letter. I then opened it and invited the author to send his idea, and it wasn’t half bad. I was a decent idea with good potential for positive impacts, but I almost didn’t even look at it. Here’s what made the initial message ambiguous:

I said no because the offer was vague

I knew only that this anonymous person had an idea. I didn’t know what the idea was, or even what it pertained to. I also had no knowledge of the sender’s qualifications to offer advice to me. Lastly, I had no clue how useful or valuable this idea would even be.

  • No indicator of benefits beyond “maybe of use”
  • No knowledge of sender’s qualifications or expertise
  • No understanding of the idea itself.

Bottom line: why should I care?

I didn’t know what would happen if I said yes

Responding to a DM isn’t that much of risk. But it is a risk. If I respond to a cold DM, I run the risk of a few mildly unpleasant out­ comes, such as: An uncomfortable sales conversation; disappointment with the decision to respond; or just an awkward moment with someone who doesn’t know how to converse very well.

Basically, awkwardness was the only risk I faced by responding. But the benefits of responding that I could identify still didn’t outweigh that risk.

It gave me no reason to say yes anyway

That’s really all it comes down to. The offer was vague. The benefits of saying yes weren’t clear. There were a few reasons, however trivial, to say no (or to not respond at all in my case)… and there was nothing on the other side of the scale to get me to do any different.

The difference between curiosity and ambiguity can be summed up with one simple comparison: Picture a woman in a bar late at night, by herself, en­joying a quiet drink. There’s a man at the other end of the bar who keeps glancing at her. Is this exciting to her, or is it creepy and unsettling? The answer is “it depends.”

Is the man well­ dressed, or is he barefoot and wearing overalls with no shirt underneath? Is his hair styled nicely, or is it matted and unkempt? Is he confident and forthright in his eye contact, or is he nervous and shifty eyed? Has he been talking to people around him throughout the night, or has he been alone and avoidant the entire time?

Your personal brand and immediate appearance is a big determining fac­tor in whether you come across as mysterious and enticing or vaguely threatening. Next, let’s go into how to convert ambiguity into curiosity.

Four factors to turn ambiguity into curiosity

Let’s go back to the man at the bar. For him to be alluring and not threatening, there are four boxes that need to be ticked (and, equally importantly, four other boxes that need to remain unticked).


First, he has to look interesting. He doesn’t necessarily need to be interesting (although it certainly helps). He just needs to appear that way. He has to be well-dressed, have good posture, and be involved in conversations happening in the room.

How does this relate to a cold DM or another form of outreach? Simple. You need to have a bold claim. The DM I received had no such boldness to it. If he had told me “Hey, I have an idea for a short form content piece that might bring five or six new clients for you if executed properly,” I’d have been more inclined to respond.

You can also make yourself more interesting to strangers by having a great profile picture, a well-written bio, and a high follower count. What is apparently interesting to others will likely be interesting to you too.


Second, he has to be credible. Credibility is usually made apparent after the conversation begins. He speaks eloquently and clearly; he maintains eye contact; he asks good questions and includes his partner in the conver­sation. You can display credibility in your conversations with people online by having social proof readily available in your profile and bringing up the results you’ve gotten for clients or customers in the past. By doing that, you can make your con­versations more about your partner than yourself without ignoring your accomplishments.


Third, he has to be attractive. This isn’t talking about physical att­ractiveness. Physical looks are a part of interesting. Interest is what starts the conversation; attractiveness is what keeps it going and leads to future conversations.

The man in the bar is attractive because of his personality. He’s a skilled conversationalist. You don’t feel awk­ward when you talk to him. He doesn’t make you feel small or uninteresting, and he doesn’t make the entire conversation about himself. He makes you feel interesting, important and valuable.

The skills the attractive man in the bar has are the same skills you need in business. You have to make your clients feel good and give them a reason to continue talking to you. You can’t make them feel stupid for not knowing what you know or not having the skills you have.


Finally, the attractive man in the bar needs to feel safe. If a woman is worried that the man is going to be pushy, aggressive or dangerous, she’s going to avoid him like the plague regardless of whether he’s actually dangerous or not. The man in the bar makes women feel safe by not blocking them into a small space, maintaining open body language, not making excessive demands of them, and not being generally ominous.

The key to making prospects feel safe is similar in business. Don’t come off as pushy or desperate. Don’t act shifty or nervous. Use humor to indicate that you’re not taking things too seriously. Use your per­sonality to set your prospects’ minds at ease. Be fun and unintimidating without being lackadaisical or boring.

Four factors to avoid

Each of the four requirements above has a reciprocal that needs to be absent to have a successful conversation:

If a guy is uninteresting at first glance, he’s got very low odds of starting good conversations. If he tries anyway, he’s often perceiv­ed as annoying.

If he’s interesting and starts a conversation but isn’t credible (ends up being less interesting or valuable than he first appear­ed), he’s going to frustrate people by making them feel like they wasted their time or were tricked.

If he’s interesting and credible but isn’t very attractive (read: not a skilled conversationalist, is arrogant, awkward, rude, etcetera), he’s going to come off as off-putting.

If he’s got everything else going on but is pushy and demanding or otherwise makes people uncomfortable, he’s going to come off as threat­ening.

The same is true in your marketing. Be interesting. Don’t annoy people by sending them vague, unclear or ambiguous messages.

Be credible; don’t sucker people into conversations with big claims if you know you can’t back them up.

Be attractive. Be a skilled conversationalist. Make people feel good about themselves and their businesses.

Be safe. Don’t use high-pressure sales tactics, don’t be pushy and aggressive. Otherwise, you come off as threatening.

Tips for cultivating positive curiosity traits

Remember the order of operations and pursue them sequentially. First, be interesting (not annoying). Second, be credible (not frustrating). Third, be attractive (not off-putting). Finally, be safe (not threaten­ing). Let’s look at each of these point by point.

How to be interesting (and avoid being annoying)

To avoid being annoying, be specific. If you’re sliding into my DMs, show me why you are worth their time and attention. If you’re the man in the bar, be well-dressed, confident and forthright. Be someone who looks like they have the right to be bold.

To do this, make a bold (and specific) claim. Have a strong pro file that highlights your qualifications. For example, if you’re offering marketing, make it apparent on your profile that you’re in the business of market­ing and have a reasonable degree of success with it. Otherwise, you’ll look like a waste of time and won’t start as many conversations as you should.

How to be credible (and avoid being frustrating)

To avoid being frustrating, don’t offer bold claims that you know you can’t fulfill. This is something that LOADS of people are doing these days. They consume content from highly skilled six and seven figure business owners, even though they aren’t operating at that level yet.

And shouldn’t be expected to either. It’s perfectly acceptable to be a newcomer to the world of business and even your own chosen niche. Be honest about your skills and abilities—don’t try to come off as an expert if you aren’t one yet. If you’re honest about being a novice, I promise nobody will think less of you for it.

Conversely, if you ARE offering a promise beyond your abilities, I also promise that people will notice. So choose a promise you’re able to keep and show social proof (as well as empirical proof—charts, graphs and the like) to your prospects that indicates you’re able to make good.

If your Tinder profile shows you flying private, drinking on yachts and flaunting gold chains, but you don’t actually live your life that way, who can blame the people you attract for being disappointed when they find out who you really are?

How to be attractive (and avoid being off-putting)

This is a trick that’s a little more difficult to control, particularly for those who don’t have strong innate social skills. The key to this is making people feel good about themselves. Those who can do this often don’t understand why. The same goes for those who can’t do it. The human brain has been evolving for hundreds of millions of years and has gotten very good at automating these back-end social practices. If it doesn’t come naturally to you, you’re automatically at a disad­vantage. However, you’re not S.O.L. 

Socialization is a skill that can be learned through a combination of study and practice. However, such info is beyond the scope of this article. For further reading on being socially attractive, I would recommend the 1936 classic by Dale Carnegie “How To Win Friends And Influence People.” There’s a reason this book has been around as long as it has.

How to be safe (and avoid being threatening)

Fortunately, this one is easy. All you need to do to make people feel safe is set the conditions for safety. Remove any factors from play that might make people feel uneasy.

The man at the bar can do this by sitting with the woman between him­self and the exit. If the woman sees that she doesn’t have a clear route of escape if things turn violent, the subconscious processes that are constantly monitoring the situation for threats will be triggered.

Likewise, the salesperson whose prospects are afraid of being pressured can be made to feel more at ease just as easily. Just promising not to push or prod your prospect into making a rapid decision is enough. (Some threatening aspects of any social situation can be assuaged just by bringing them up).

A few other tips

Exclusivity makes your offer—whatever it is—intrinsic11lly more app­ealing. We want what we can’t have, and we want what others can’t have. This is why brands like Gucci and Hermes are able to sell average (and sometimes entirely impractical) products at a premium: because many pe­ople aren’t able to afford them.

If a woman at the bar sees you reject multiple women and talk to her instead, she might be more interested in you. Similarly, if a prospect shows up to a sales call with the knowledge that you only take on 10-15% of the people who apply to work with you, you’ll be the one in a position of power.

Storytelling is also a very powerful technique for creating curiosity. If you start a story but don’t end it, you leave an open loop inside your listener/reader’s mind. By opening that loop and promising a res­olution to it if only the prospect responds to your DM or books a call on your Calendly page, they’ll be more likely to do so (provided the story pertains to them and the resolution is desirable enough to take the risk of replying).

Finally, there’s the power of visibility. On the internet, you are a scammer until you prove otherwise. Sad, but true—there is no due process on social media. Scammers, fortunately, are pretty predictable in their methods. They generally attack only a single front. You never get a spam email from a Nigerian prince and then a phone call a week later. If you attack your prospects on multiple sides from different sources, you automatically make your offer appear more legitimate.


Curiosity is powerful. Creating open story loops and an air of mystery can work for you, but only if you avoid devolving into ambiguity.

Ambiguity creates confusion, and the confused mind always says “no.” To be an object of curiosity, you have to remember: Be interesting, not annoying. Be credible, not frustrating. Be attractive, not off-putting. Be safe, not threatening. Anticipate how the people you approach are likely to react to you, and adjust your approach accordingly.

Most importantly, remember this: the easiest way to hit all of these markers is to be genuine.

Have an offer that people want. Be skilled fulfilling it, and have proof that you’ve done so successfully in the past. Be good with people and able to make them feel good about themselves. Only approach people you genuinely believe would find your offer valuable. (Hint: if this number is small, it probably means you don’t find your offer valuable yourself, which is a catastrophic problem).

If you find yourself having to dress yourself up in clothes that don’t suit you; having to stretch the truth or outright lie to attract prospects; or having to be pushy or desperate to close deals, it means that you need to put in more work. The easiest way to come across as high value is to become high value.

Stay hungry, be confident and get out there. The longer you stay in the game, the easier it becomes to crush your goals and feel damn good about yourself in the process. Good things are coming, my friend. Make sure to stick around long enough to get your cut.


I'm John Kakuk.

I’m a brand designer, web developer and marketer working with architects, engineers and construction companies. My purpose is to help others achieve the best versions of their businesses and themselves.

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