1. “I looked at your website.” (or being phony with flattery or AI)
2. “I’m looking forward to hearing from you.” (or speaking to you)
3. “Thank you for your patience.”
4. “I want to be respectful of your time.”
5. “I’ll keep this short.” or “Have you got 60 seconds?”
6. “I’ll be in touch if it makes sense.”
7. “I hope you’re doing well.” (to a stranger)
8. “Sorry for the late reply. I’ve been busy.”
9. “So, where do you live?” (on a call)
10. “So, what are we talking about today?” (on a call)
11. “I guess you’ve been busy.” (on a second email attempt)
12. “Did you see my last email?” (on a second email attempt)
Intro
You don’t get a second chance to make a first impression. Whether it’s fair or not, we get judged when we speak with someone new, or send a cold email to a potential new contact. They say that you shouldn’t judge a book by its cover, but what else can you do, read every book in the bookstore before buying? So of course people cut corners when they read email. We all do.
But I was shocked when I learned how little time a reader gives. I was fundraising for a startup, and one of my advisors suggested I use Docsend. It’s a great cloud service that not only stores your investor slide deck and other materials, it also tracks who’s clicking and how long they spend reading. I assumed that the average investor would spend 2 or 3 minutes reviewing my easy-to-read, well-written 10-page slide deck with very little text.
Nope. 30 seconds. Sometimes 60 seconds, but sometimes less. That’s how long I had to get the attention of an investor.
It makes sense. How many seconds do we give to a YouTube video before clicking elsewhere? How much attention do we give to the inbound emails we receive?
For this reason, when you’re speaking with someone, or sending them an email or message on LinkedIn, you have to be smart. You have to get their attention with your tone and word choice.
With that in mind, here are 10 things never to say in a message or when speaking to someone.
1. “I looked at your website.” (or being phony with flattery or AI)
Don’t do this without specifics. If you say, generically, “Oh, I spent time researching your business and thought we could be a great match”, or “What you are doing is so impressive”, it’s obviously phony flattery. A generic message with hollow compliments ironically signals “I didn’t spend any time on your website”, but also “I think you’re stupid enough to get fooled by this”, which is even more insulting.
How to fix it? Include specifics. If you really spent time on your target’s website, show it by manually tailoring your email to what you learned. Do it as warmly as you can, because AI tools in 2026 are capable now of generating “specifics” that thank goodness still feel false. You want your real, actual target research to read as genuine, because it is genuine.
Another variant of this is using AI to write your message. (Or to “rewrite” it, whatever that means. I think you’re fooling yourself that the resulting message is somehow from you.) Okay, I will admit that a lot of muscleheads will get fooled by AI, which writes bland, tone-deaf, alien feeling prose. But do you want a deal with a musclehead? How about making a deal with world-mover, somebody with the power and influence to elevate you and your business to the next level?
Those people aren’t so easily fooled. When you send an AI-written message, you’re saying:
- I’m willing to deceive people.
- And I think you’re stupid and will accept this as written by me.
So, don’t do that. Don’t write phony AI messages to people. What were you thinking? Look. People (except an occasional musclehead) only buy when they have found a perfect match. You want your target to think, “I’m so lucky! Look what I got today in my email! It’s exactly what I need.” You’re just not going to get there with AI. You are spinning your wheels. You are grinding up the Internet. If you really feel that you (a) cannot target customers who truly need you and (b) therefore must blast spam to the world hoping for random bites, then either (c) you do not have a worthy product or service, and should improve it or (d) you just haven’t done your homework to find the right target customer, the potential customer who does need you desperately.
Try reading the book “Crossing the Chasm”, by Geoffrey Moore. Instead of blasting form letters to 10,000 people, you will learn to identify the 200 people who need you the most. That’s not such a large number. For 200 people, you really could write a warm, well-researched message with points of connection that feel real, because they are real. They came from your spending a few minutes on each target to craft a custom communication. Those are the messages that break through the noise, that get read.
To recap, focus your targets to a small list, then research each target and write something specific and not phony seeming into every message you send, to prove that you’re not spam. It proves that you care, and that makes the recipient think, “Maybe I should care, too!”
2. “I’m looking forward to hearing from you.” (or speaking to you)
This one I learned from Dale Carnegie’s books. He’s the self-help guru who wrote How to Win Friends and Influence People, a book that’s not about faking anything, but being genuine. When you write “I look forward to hearing from you”, it’s a statement that assumes that the reader will get back to you. It can be read as a demand. Imagine that you went into a bar, met an attractive person there, and said “I look forward to dating you.” Well, you haven’t even asked him or her out yet!
So don’t use this phrase. Instead, if it’s a cold email, try “Would you take a call on this?” or if you are following up on a first call, don’t be desperate, Just say, “Thank you again for the great call and any consideration that may be possible.”
3. “Thank you for your patience.”
This phrase has become common recently and it irks me. Imagine that I call my Internet provider, and before getting to speak with a real peron, I have to punch in a lot of numbers and wait on hold for 35 minutes. That’s 35 minutes of my life. I’m not burning with rage, but it’s annoying. It’s irksome.
Then someone finally speaks with me and says “Thank you for your patience”, which is like saying “You have been patient. You are completely fine with this delay. You have blessed me as not doing anything wrong.” That’s quite an assumption! How awful to be kept waiting and then, instead of empathizing with the person who waited, instead you tell them how they feeling, blowing off their needs and viewpoint. Talk about not reading the room!
So don’t use this phrase in your emails or on calls.
4. “I want to be respectful of your time”
Here’s another unfortunate phrase that has recently become common. If you need to reject someone, you might be tempted to say, “It doesn’t seem like this deal is going anywhere. We could discuss it further, but to be respectful of your time, let’s stop here.”
What a saint you are! So you are not only rejecting the person at the other end of the conversation, you’re making it seem like you’re doing them a favor! It’s like you’re saying, “Of course I’d be glad to keep talking, but I’m so selfless, that I want to give you a little gift. It’s your time that I’m thinking of.”
No, no, no. When you end a conversation, of course it’s your time that you want to save, not theirs. It’s no fun for the other person to get rejected. Don’t make it worse by acting holy. It’s like getting dumped by a partner who says “It’s not me. It’s you.”
Instead, when you need to reject someone, be respectful. Put a little kindness out into the world. Just say, “It looks like we’re not a match,” or “I’m sorry, this isn’t for me.”
5. “I’ll keep this short.” or “Have you got 60 seconds?”
I get it. You want the person who just got your email to actually read it. You’re trying to say, “Hey, please read this! It won’t take you much time at all!” But, by the time you’ve said “I know that you are busy, so I’ll be brief,” you already haven’t been brief. You’ve already wasted some time and probably lost most readers.
If you want to be brief, just be brief. People don’t really read emails these days. We glance at them, trying to figure out whether we should bother to read them. So get to the point immediately. Think of yourself on a cold approach as falling off of a cliff. Your job is to stop that fall as quickly as you can, in the first 5 seconds. So the top of your message should be a grabber, a “wow”, something interesting. Starting with filler, like “I’ll keep this short”, or “My name is _________ and my company is ______”, contains no part of your clever argument to keep them reading.
6. “I’ll be in touch if it makes sense.”
Another version of this is “We will follow up if there is any interest”. Well, of course. Of course you’ll be in touch if it makes sense. But if it doesn’t make sense, you won’t bother to say so? If you decide to say no, you’re declaring, “Oh yeah, I’ll ghost you. If I decide no, good luck waiting and wondering.”
There’s just no need to throw your power around like this. It doesn’t show kindness. If you’ve had a business meeting or a business call, some kind of response is obligatory, even if it’s just a quick, one-line email. If you’ve only had an email exchange, and don’t have an obligation to respond, fine, but don’t throw it in someone’s face and make them feel small.
When I’m hiring, I have to reject interview candidates of course. I reject them at the resume stage, after an interview, and even after more than one interview. I have found that doing it with kindness takes almost no additional time, and it reflects well on me and my organization. Often, the person being rejected writes back and says, “Thank you for at least responding!” and thanks me for my warm tone of voice.
Job hunting (or sales) is dehumanizing. If it’s not a form letter, then there’s a real person at the other end of the email. Show kindness.
7. “I hope you’re doing well.” (to a stranger)
I feel the same way about “Best Wishes”. You’re a stranger writing a cold email, and you’re wishing the recipient your “best”? You hope that a total stranger is in good health?
It strikes the wrong tone. It’s too familiar. How you could credibly care about someone’s health whom you never met yet? Are going to ask them how their mom is, to? It comes across as phony, in addition to being an empty phrase that doesn’t get right to the point. It doesn’t help you get the reader’s attention when you’re falling off of that cliff of limited attention spans.
8. “Sorry for the late reply. I’ve been busy.”
We’re all busy, man. Who are you, the King of England? When you say, “I’ve been busy”, you are communicating two things:
- I think I’m busier than you. (In other words, more successful, more active. It makes you sound superior while simultaneously clueless about how active other people are.)
- I can’t handle my schedule. I’m overwhelmed. (So hire an assistant. Come on.)
9. “So, where do you live?” (on a call)
Once I had an investor call where I brought on one of my team members to back me up, a business guy. Let’s call him Jerry.
I had put a lot of homework into the call. I did my research, was prepared, and knew exactly what I wanted to say, first to bond with the investor socially, and then to make my case to get the funding.
Then the call begins and the first thing that Jerry said was, “So where are you based?” This signaled that he hadn’t even bothered to look at the investor’s LinkedIn page, where the city was clearly written. He pulled the rug out from under my attempt to seem well prepared and warm. What Jerry communicated was, “I know nothing about you” and “I couldn’t be bothered to find out.” It’s almost like Jerry, through his lack of attention, had said, “Even I don’t think a deal is likely here.” So why should the investor think a deal is likely?
Another variant of this is “What time is it there?” Jesus. Look up their location and figure out the time zone. Don’t quote from The Book of Awkward, or The Book of How to Not Bond With People.
10. “So, what are we talking about today?” (on a call)
This one’s even worse than “So where you do live?” Not only have you done zero preparation, and you basically admitted that you don’t care at all about the person at the other end of the conversation — not a great way to make a first impression — but also you’re also giving up the initiative.
Take the initiative. Come to the meeting prepared. Have talking points and a proposed agenda. You set the topic. You drive the conversation. I don’t mean in a bulldozer, aggressive way. Just, you’ll be surprised how far you get just by coming to any conversation knowing what to say.
11. “I guess you’ve been busy.” (on a second email attempt)
Jesus. When you are sending a second message to someone who didn’t reply the first time, don’t be bitter and weird.
- If your first message was a cold email, the recipient didn’t have any obligation to respond to you, so don’t make it sound like you are desperate and annoyed.
- Or if there is some obligation, for example you are a following up on a business call, or following up with someone who offered to read your information packet and get back to you, keep it cool, bro. They just didn’t get to it yet, or who knows, they might have had a very stressful week or been traveling. Just politely say, “I’m just following up on the below.” In extreme cases, you could say, “Just checking in to ask, are we still talking?” If you really feel that you must say “you’re ignoring me!” (for example someone who took a call with you and ignored 6 follow-ups), do it with kindness.
- Try writing this: “No reply. I hope that you’re not having a personal emergency.” Sometimes, they really will be in a personal emergency. Think how foolish you would feel to grump at someone, and it turns out that her father died. Stephen Covey also makes this point in the best-selling business self-help book, The 7 Habits of Highly Effective People.
12. “Did you see my last email?” (on a second email attempt)
What are you doing? This time you’re not just being bitter and desperate, and misreading the recipient’s obligation to reply to a cold email, which is zero… you’re also creating a barrier to the recipient responding if they choose to.
Don’t make the recipient chase down your previous email. That’s work that gets in the way of their possibly saying yes. Don’t assume that the recipient remembers who you are and what you said in your last message, or even that they read in your last message. Instead, resend your previous message and just put at the top, confidently, “Just checking on the below”.
Epilogue
So those are my recommendations what not to say, to anyone. If you found this article too long and ranting, then great. That just means you have a good eye for writing! Keep putting it to use.
Here’s a bonus no-no. Don’t ever say “Dear” in business emails, at least not in America. I know that they teach that in schools, but it is wrong, out of date by 50 years. Good luck.
