5 email mistakes you make every day and what to do instead

The Unwritten Rules of Email

Learning how to ask for a meeting by email is an art form. It's a feeling process. One where a single word can close or destroy a deal. In email: Every. Word. Counts.

I've made a great deal of terrible email mistakes along the way.

Here are five mistakes that I've made so you can avoid them.

1. DON'T: Write "Feel free to."

I used to try to sound breezy in my emails. Thrilled that someone had actually opened my email, I'd close my follow up note with phrases like "feel free to take a look at the attached." Or "feel free to share some dates that may work for a meeting.."

Never do this.

What I didn't realize is that I was telling the recipient of my email that things are open ended. I had no deadlines. I didn't have a goal in mind.

By telling the recipient to "feel free to" I had dumped the responsibility of following up on the recipient.

Not cool.

DO: Write "I will."

Shifting your voice from passive to active will change the tone of your email. Now you have an agenda. You have a goal. Now you've committed your time and effort to the recipient and you're ready for next steps.

Stating: "I will follow up next Monday at 10 am to address any of your questions" is much more powerful than "feel free to follow up with questions."

2. DON'T: Reach for false rapport.

Recently a young executive solicited me via email. Not unusual, and appropriate. But, yet moments after she sent me the first email, she sent a follow up attempting to strike up a conversation about my love of CrossFit.

This false attempt fell flat because it wasn't coming from a genuine place. She was looking for an activity that I love and attempted to wedge herself into that love. Not cool.

DO: Build rapport by starting small.

My friend Oren Klaff is the master at building rapport via mail. I used to send sales emails with lots of links, too much detail, heavy copy etc. I would lose the deal before my prospect even opened the note.

Now I listen to Oren and I start my prospecting email communications short and sweet. Like this:

"Dear John, If I sent over a short one page overview on my company, would you give it a look and give it a quick yes/no?"

Short, simple and to the point. You've communicated your desire to share information about your company, and you've taken the work out of the response. All the recipient needs to do is say - yes, send it over, or no, thank you. Easy. Plus, once you get a response, now you have a conversation!

Building rapport takes time. Be careful not to force it via email.

3. DON'T: Write it's "urgent."

If it were urgent you'd call, or show up, or call 911. We're not curing cancer here. We're conducting business. If something is urgent, don't send an email. It's never urgent for the recipient.

If you feel the need to write "urgent" in the subject you need to reevaluate your motivation for sending the email. Where does that urgency lie? Is it urgent that you make the sale? Urgent that you tell your boss you received a reply?

You should never impress urgency upon the recipient of your emails. It just won't work.

DO: Write "there are a few time sensitive matters I'd like to discuss with you."

Expressing that there is time sensitivity is fully appropriate. Communicating that urgency in an urgent manner isn't.

Yes, there is a difference.

If you're leveraging email as a communication medium, you can properly communicate an appropriate sense of urgency without screaming that the sky is falling.

4. DON'T: ask "Why haven't you replied?"

This is never an appropriate follow up. I cringe when I admit it - but I've sent this email. Please don't make my mistake.

DO: Install Hubspot's Sidekick, and sit tight.

It's not personal. They're busy. If they're interested they'll get back to you. If they're not interested, they won't.

Simple. A little painful, but simple nonetheless. Move on and focus on closing the next deal.

5. DON'T: Read into responses, and or lack thereof.

Some people can be passive aggressive via email, for sure. Some are also bad writers, and come across as aggressive when they don't intend to.

For example, you may ask a prospect a question, and they may reply with a simple "no."

To some this sounds arrogant, or harsh. To others this is something altogether different. The recipient may have sent this note minutes before takeoff, as a flight crew is telling her to shut down her mobile devise.

No malice, or aggression intended.

Simple and effective email communication that isn't "softened" with everyday language should never be viewed as anything but simple and effective.

Reacting to what you think is a bad email can backfire in a big way. Take a step back. Or better yet, sleep on it. Never, ever fire off an email in anger.

DO: Take every email with a grain of salt.

It's an imperfect medium in which we add heavy emotional weight. It's our nature to interpret. Allow yourself distance from the immediacy of email.

RELATED: 18 things successful people do in their 20s

18 things successful people do in their 20s
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5 email mistakes you make every day and what to do instead

When you're just starting to build your career, it can be difficult to arrange your days for maximum productivity.

As Étienne Garbugli, a Montreal-based entrepreneur and author, explains in his presentation "26 Time Management Hacks I Wish I'd Known At 20," setting deadlines for everything you're working on and avoiding multitasking are two keys to effectively managing your time.

While there are those who spend their 20s drifting without direction, there are others who are so afraid of failure that they take a job solely because it provides a comfortable paycheck.

But, says Quora user Rich Tatum, that job you're not interested in quickly becomes a career, and by the time you're 30, it's a lot harder to start pursuing your passion.

The key, says author Cal Newport, is to pursue something that you're passionate about and is valuable to employers.

A Bankrate survey of 1,003 people found that 69% of those ages 18-29 had no retirement savings at all. Twenty-somethings who don't have enough foresight to recognize that one day they're going to retire and need money to live on are missing out on years of money gained through interest.

Entrepreneur Aditya Rathnam writes on Quora there's no need to start investing too much, since you're just starting your career, but it's essential to take advantage of your company's 401(k) matching program, if one is available, and/or open an IRA account.

Seventy percent of college students graduated with an average of $30,000 in student-loan debt last year, but that doesn't mean that debt is somehow a badge of adulthood.

Debt will start to haunt you, says Quora user Thea Pilarczyk. Develop a repayment plan that lets you pay off your loans as quickly as you are able to and is within your means, and use credit cards to build credit, not pay for things you can't afford.

As each year goes by, it becomes harder to start a sustained exercise regimen, and harder still to recover from a late night of drinking.

While you're still young, says Quora user Mo Seetubtim, develop healthy habits that will set you up for the next phase of life. Enjoy your vices in moderation, eat well, and choose a workout over a happy hour now and then.

If you're an ambitious 20-something who thinks that adulthood means having things figured out, then getting fired from a job, ending a serious relationship, or having your company fail can be devastating. But the truly successful are able to learn from what went wrong and move forward all the wiser.

"Getting fired and waking up the next day as usual made me realize that failure isn't the end of the world. Getting dumped taught me the difference between a good and a bad relationship, something I already knew inside but refused to accept until the bad relationship was over," says Carolyn Cho on Quora.

Your 20s are a time to start building a network that will establish a foundation for your career. If you know that, it's a good idea to be on friendly terms with your boss, clients, and all of your coworkers.

Eventually, however, you're going to meet people you don't like and those who don't like you. That's normal, and not a sign that you should change yourself, as long as everything else is going well.

"Inevitably, someone will always dislike you. I wish I had figured this out a lot earlier and stopped trying so hard and worrying so much about it," says Cho.

While it's good to set career goals that keep you focused and motivated, you should avoid getting caught up in intricate five-year plans, Joe Choi says on Quora.

Author and investor James Altucher says that one of the main problems he's found among people in their 20s is that they get caught up in absolutes. He recommends keeping yourself flexible and open to new experiences. There's a good chance that the ideal life you envisioned for yourself at age 20 doesn't resemble the one that ultimately makes you happy at age 30.

"With no family to feed and no dependents counting on you, your 20s are without a doubt the years to take a leap and pursue your passion," says Jessie Goldenberg, who abandoned a promising media career shortly after college to start her own business, the successful mobile fashion boutique Nomad.

Of course, taking risks to the point of being reckless is as bad or worse a habit than suppressing ambition. Investor and "The 4-Hour Workweek" author Tim Ferriss recommends taking the time to think through how to recover should your attempt fail and then seeing if it's worth the risk.

Degrees from elite universities may make you smarter and help your reputation, but they won't count for much if you don't keep learning as you go.

Read as much as you can about your industry, and learn to develop skills that you probably never would study in a classroom, like "the abilities to assimilate, communicate, and persuade," Tatum says.

When you're just starting out, you probably don't have much disposable income. But just because you can't take a weeklong ski trip in Switzerland doesn't mean you should confine yourself to the space between work and home.

Your 20s, Shikhar Argawal says on Quora, are a time when "you are mature enough to go out on your own and immature enough to learn from others." Break out of your bubble as much as you can afford to, and don't ignore career opportunities far from home if they arise.

"Your college pals that you think will be your best pals for life? Some will still be there at 40, most will be living their lives doing their thing," writes Sutherland Cutter on Quora. As everyone is figuring out their lives, you'll realize that relationships take work to maintain.

It's worth staying in touch with former coworkers and buddies, though. The 1973 study "The Strength of Weak Ties" by Mark Granovetter of Johns Hopkins University found that the weak ties you share with acquaintances are most often the connections that get you ahead, since they have access to different networks and ideas from you.

Tech entrepreneur and author Ben Casnocha has worked closely with LinkedIn founder and chairman Reid Hoffman for several years and writes that the greatest lesson Hoffman taught him was "that you are the average of the five people you spend the most time around. You really are the company you keep."

There's no need for maintaining toxic personal or professional relationships out of loyalty.

Picking fights and holding grudges will make you miserable, Tatum says, whether that's in your personal or professional life.

You'll realize soon enough that your hard work won't always be recognized, either, Rahul Bhatt writes on Quora. But never let that be an excuse to be lazy or bitter.

Use the time when you're still single and without kids to take bigger risks than you otherwise would, but don't live recklessly.

A decision you make in a few seconds off an emotional impulse "can rob you of years of joy and happiness," Tatum writes.

Quora user Arpan Roy writes that as he looks back on his 20s, he's come to see that even though he loves his parents and appreciates their advice, it wasn't always the best for him.

As you grow older, you'll come to see your parents less as authority figures and more as people just doing the best they can. "After all, your parents are human, and humans are not correct all the time," Roy says.

The deceitful manipulation of others and sucking up to superiors can only take you so far — they're not the keys to a lasting, fruitful career.

"The truth has a way of rearing its ugly head, so the sooner you can come to integrity with yourself and the world at large, the sooner you'll be able to get working towards what you really want, who you really want to be," Arjuna Perkins writes on Quora.

"If I could go back in time, I'd introduce my 22-year-old self to a quotation by the writer Brian Andreas: 'Everything changed the day she figured out there was exactly enough time for the important things in her life,'" Huffington Post cofounder Arianna Huffington writes on LinkedIn.

And if you are obsessed with your work — whether or not you love it — understand that you will actually be making yourself more productive by allowing yourself to enjoy life.


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