Common questions about email

Today I’m sharing some of the email questions I’ve been asked by consulting clients and coaching students… in case you’ve been wondering some of these same things as you’re working on your email marketing:

#1) I’m afraid of mailing too much… I don’t want to seem desperate or pushy.

Operate from the assumption that people are super busy and miss the thing you’ve said 20 times already. Take it from the head of an internet marketing guru’s copy team – I can put the same message in 50 different places and STILL get people asking me if I ever posted that message. They’re busy. They’re distracted.

Not trying to be mean, but most probably aren’t waiting by their computer waiting for your email and lighting candles at their altar in preparation for reading it. That’s a GOOD thing.

First, that kinda customer probably would drive you nuts. Second, it means your definition of “bothering” is slightly warped and distorted. They’ll tell you when you’re bothering them, trust me. I can send the nicest, most helpful email out there and if someone’s having a shitty day, they’ll write back and tell me to go fuck myself (instead of simply unsubscribing??). 

Your job is to put the message out there. Swallow the instincts of being too pushy and too desperate – remember you’re on a mission to help people. And helping people sometimes means getting in their face (in a loving and compassionate way).

#2) Some people say mail once a week, and some say mail every day. What should I do?

All kinds of people say all kinds of things. 

I was on an expert panel at a conference for copywriters – this was back in March (which feels like 20 years ago) in San Diego. Someone in the audience asked the panel how we got clients. 

I was last to speak out of the 5 of us, and the interesting thing is that the four who spoke before me each had a different answer. 

So THAT was my answer – I want you to take note of the fact that everyone up here gave you a different answer. Everyone up here is successful. The takeaway here is that it ALL works. What you’ve got to figure out is what works for YOU.

I’ve tried every method of prospecting under the sun – I even dropped flyers and spent time cold calling. Now I prefer networking and live events for drumming up business. But that doesn’t mean flyers, calls, and other forms of prospecting don’t work. I just hate doing those, so I don’t.

#3) I’ve got a CTA in my emails… it’s “if you’re interested, visit my website and book a call”. Do I need a “harder” call to action, or to put one in every email?

Couple things:

1) you don’t need a hard CTA in every email. Only you can know if that feels right to you and your customers – and you’ve gotta test (and be willing to lose subscribers) to find out for sure.

2) yeah that CTA is not doing you any favors. There’s no urgency, no scarcity, no drive. Plus it’s passive… one simple, subtle, and POWERFUL shift you can make is reframing it from “IF you’re ready, do XYZ” to “WHEN you’re ready, do XYZ”. 

#4) I hear automated emails are the way to go. How long should an automated sequence be?

The longest sequence I’ve ever run is for a live event. It takes a LOT of touch points to sell seats to a live event, and I like to start promoting about 4-6 months out (and my first email is usually a save the date type announcement with a biiiiiiiiiiiiiiiig space between that and the “official” start of the registration sequence).

And lemme tell ya – I’ve never ONCE run those sequences uninterrupted. Meaning twice a year every year, my team and I kick off this registration. And every year we have to adjust the order or add or delete emails, or react in real time to something that happened that we couldn’t possibly have predicted.

Prime example… this year the entire live event promotion campaign was put on pause because guess what? Like every other big event in April, it was canceled.

I tell you all that to say, having a sequence is good. But I never run them unmonitored/uninterrupted/without consideration for what’s happening now and how the narrative needs to change. 

If I were still sending out event registration emails or attendee emails to get them psyched up for coming to an event in Florida right now (beginning of May 2020, as I write this… when we’re still in the middle of a global pandemic), they’d think I was completely tone deaf and heartless and just cared about the money.

We had to shift gears and let people know the event’s canceled – we are planning on doing this virtually but have no idea what that looks like for now, so just bear with us as we move a 1000+ person live event online in less than a month. Ya know?

Plan for the worst, hope for the best. Give your automated sequences some flexibility to react to what’s happening now, or risk looking out of touch at best (or predatory at worst).


Got any questions on email marketing? Pop ‘em in the comments below and I’ll answer them. 

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