What is the best way to email a group of people and how do I save the list for future use on G-mail? Thanks so much, Cheryl Rosenberg, becounted4israel.org.

That’s a great question, as it brings up two important factors in sending emails en masse. First, the etiquette of sending to many people at one time requires you to construct your emails in a pretty specific way. Second, how do you actually send the emails without being flagged by your recipients’ mail servers as a spammer?

Proper bulk-email etiquette requires you to BCC your recipients. First and foremost you want to protect the privacy of the people your organization interacts with, allowing you to maintain a healthy level of contact with them. Without blind copying the email list, you would essentially be sharing sensitive, proprietary data with every other person you’ve emailed. Ensuring this level of privacy shows your contacts that you are out to protect their interests, as well as get your message across.

Also, it is important to give your recipients the opportunity to opt out of your emails. This allows for those who don’t wish to see your emails to tell you as much, while at the same time protecting you from getting flagged as a spammer. I would like to point out that once your email address gets flagged as spam and blacklisted on a mail server, it is incredibly hard to get that status reversed. This can lead to your emails being automatically blocked from going to any recipient with that mail client.

Take your time to make sure the email addresses are correct. It is very frustrating to have to sift through bounce-back ‘Mailer Daemon’ emails to figure out whose address is incorrect. Also, make sure not to manage personal and work emails through the same site or program. I can’t tell you how many times I’ve received emails from clients’ personal, rather than work, email addresses. It’s always good practice to keep your business and personal life separate, and that applies to email as well.

Now, if you are going to send bulk emails on a regular basis, there are two companies that I would recommend to handle your contact lists that are already green-lighted by most mail servers to send mass emails. They are: Constant Contact (www.constantcontact.com) and MailChimp (www.mailchimp.com). Both have a free version that allows you to test out their system to see if it’s what your organization needs. Constant Contact gives a 60-day free trial for fewer than 100 contacts. However, you can send out unlimited email “campaigns” to those contacts. MailChimp has a permanently free option under 2,000 subscribers, although you can only send out 12,000 emails per month. However, the free MailChimp does not give you access to certain tools for increasing your email’s deliverability. It does not have MailChimp’s “SocialPro” to analyze your subscribers’ social media activity, and doesn’t allow for auto-responders.

The Constant Contact free trial ends quickly for many beginners because, if they are doing it right, they quickly exceed 99 subscribers before their trial ends. Constant Contact’s fees are $15/month for fewer than 500 subscribers. There is also an additional $5/month for image hosting, but this is not necessary if you have a website to store your images. This also includes five active auto-responders.

MailChimp costs $10/month for fewer than 500 subscribers and $15/month for fewer than 1,000 subscribers. After that, their pricing converges. Constant Contact wants you to pay monthly and have pre-payment and non-profit discounts. MailChimp offers monthly plans as well as pay-as-you-go plans that act like stamps. Both sites provide templates and pictures that can make your email campaign that much more attractive. Constant Contact, for instance, has Hebrew and Jewish clip art.

Both companies have support during the trial period to help you upload your contact lists and get your emails sent out. What makes these two services more attractive than just sending from your own email address are the reports you can run. These reports can show who received the email, and even if the email is read or rejected.

It is also a good idea to separate your email lists to tailor to different groups receiving your emails.

(Tip: If you aren’t sending email to your list at least once a month, don’t bother—your subscribers have forgotten about you).

Shneur Garb is the CEO and Founder of The Garb IT Consulting Group in Teaneck. For questions or comments email [email protected]

Shneur Garb