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Well Said!

No Need to Walk on Eggshells with Follow-up Emails

By Mike O'Horo

Follow up email examples: No Need to Walk on Eggshells.

When sending a series of follow-up emails to prospects, many lawyers get anxious about how well they’re balancing persistence against the risk of being perceived as pushy and turning off the prospect. This is a legitimate concern.

However, you don’t have to walk on eggshells. As long as you do two things consistently, you won’t risk alienating anyone.

  1. At the conclusion of any contact, whether by phone or email, always ask, “What’s our next step?”
  2. Base each subsequent communication on that declared next step.

Follow up Email Examples: Did This Lawyer Get Too Pushy?

Here’s an actual example of a back-and-forth email thread between “Richard,” a lawyer I coach, and “Janice,” the representative of an industry organization with which he was trying to secure a speaking gig. In the end, he asks me if he pushed too hard.

From: Richard [Lawyer who Mike coaches]
Sent: Monday, April 23, 2018, 10:48 AM
To: Janice [Trade group representative]

Subject: Reschedule our call?

Janice, Looks like this morning didn’t work out for our call. If you let me know another time that may work for you, I’m happy to reschedule at your convenience. Thanks!

Best, Richard

From: Janice
Sent: Monday, April 23, 2018, 11:03 AM
To: Richard

Subject: RE: Reschedule our call?

I’m so sorry Richard, I thought the appt was 10:30 central time so 11:30 est.  Will 11:30 a.m. est work for you today?

Richard and Janice spoke by phone, followed by these email exchanges.

From: Richard
Sent: Wednesday, May 02, 2018, 9:33 AM
To: Janice

Subject: Next steps re [conference topic]

Janice, Thanks for your enthusiasm about the collaboration we’re exploring re: presentations, deeper dives. Next steps? Thanks!

Best, Richard

From: Janice
Sent: Friday, May 04, 2018, 1:27 PM
To: Richard

Subject: RE: Next steps re [conference topic]

Hi Richard — My colleagues and I have been traveling non-stop the past week and next week looks the same.  We will be meeting towards the end of the week of May 15th so I should have an update for you then. Thanks and have a great weekend!

From: Richard
Sent: Tuesday, June 05, 2018, 12:27 AM
To: Janice

Subject: RE: Next steps re [conference topic]

Janice, I hope you are doing well. I wanted to touch base with you. Any thoughts on next steps? Thanks!

Best, Richard

From: Richard
Sent: Tuesday, June 19, 2018, 12:10 PM
To: Janice

Subject: RE: Next steps re [conference topic]

Janice, Since we last spoke, I’ve done some additional speaking on [topic] (e.g., at XYZ Org) and booked some additional future speaking engagements (e.g., ConfABC). If you want to see a sample of what the opening of one of my presentations looks like, here’s a link.

It seems like maybe the initial enthusiasm for having me speak to [Trade group] members has faded with time? Please let me know, thanks.


When things bog down, it’s a good idea to give the person the opportunity to pull the plug. If things have changed and it’s no longer a viable opportunity, you need to know that so you can disinvest. If the prospect has mentally moved away, you don’t want to be the only one still pursuing a dead idea.

From: Janice
Sent: Tuesday, June 19, 2018, 5:05 PM
To: Richard

Subject: Re: Speaking to [trade group] members re AI and alternative data

Thank you, Richard, for your email and update. No, I would not say there is a lack of excitement around this topic anymore, the program side of the conference is still identifying topics and no speaker invites have been sent out yet. I’m expecting to see something from them within the next two weeks or so so please stay tuned.

From: Richard
Sent: Tuesday, July 11, 2018, 2:30 PM
To: Janice

Subject: RE: Next steps re [conference topic]

Janice, I wanted to touch base and see if there was any update?  Many thanks.

Best, Richard

From: Janice
Sent: Thursday, July 12, 2018, 9:14 PM
To: Richard

Subject: Re: Speaking to [trade group] members re AI and alternative data

Hi Richard, Thank you for your constant follow-ups. Invites still have not gone out yet for the breakout sessions on Annual but it does look like some other initiatives are starting to take precedent for this year. I will let you know if anything changes on our end but at this point, I don’t think this will work out for October.

Thanks, Richard, and please let me know if I can be of any additional assistance.


What Happened With These Follow-up email examples?

Here’s where Richard hit the panic button. You can see, though, why he felt like he might have pushed Janice away, prompting him to send me this email:

Based on our concept of making sure to follow-up and get decisions (and not letting things fall through the cracks), I’ve stayed on top of the opportunity below. However, I get the feeling I may have turned her off by pushing too much. I would have allowed more time and taken a softer approach in the past, but that might have its own downsides. Thoughts on this one, and on hitting the right balance in general? Thanks.

Here’s my response, assuring Richard that he actually did a very good job.

It’s possible, but I doubt it. Reviewing the thread:

  • Your May 2 email appears to be in response to a phone conversation.
  • Your June 5 email is in response to her volunteering that she’d have an update around May 15. You gave her two additional weeks of space.
  • Two weeks after that, June 19, you inquired about the update she’d promised a month earlier.
  • Her immediate reply said another two weeks and said “stay tuned.”
  • You gave her three weeks, inquiring July 11.
  • Her reply the next day is the long-promised update. It just wasn’t the one you expected or wanted.

I don’t see anything that I’d consider badgering in either your tone or frequency. The only thing you might consider in the future is mixing in some content relevant to her role and your topic, but unrelated to the speaking gig decision. That way, every message isn’t asking for an update, yet still subtly reminds her that she promised you one and keeps you associated with the topic about which you aspire to speak to her group.

IMO, her email gives a different answer to your earlier “interest fading?” question. It’s fading relative to other priorities. Stay in touch with relevant content so that, when the idea resurfaces, she remembers you.

Remember that “yes” always comes fast; “no” usually takes much longer because people don’t like saying “no,” so they delay it, hoping that circumstances will make it unnecessary.

Negative outcomes aren’t necessarily evidence of error by you, any more than positive ones indicate genius.

Any sale is about the buyer’s interest; it’s rarely about you. My general philosophy is “whether social or business, the limits of progress in any relationship or endeavor are set by the person with the lesser interest.” That’s why selling is so hard. At least initially, sellers always want it more than buyers. That’s why we’re always trying to achieve the elusive balance between persistence and patience.

Richard exhaled in his reply and revealed what had triggered his anxiety.

Thanks. Really, I mean it — thanks. This is hugely helpful. Her comment “thanks for your constant updates” sounded to my ears like “you overzealous spamming pain in my butt.” But I’ll take it as “it is what it is,” thank her for letting me know, and send her unrelated content in a month or so.

Balance Progress Checks With Valuable Content

As you see from this timeline, the pacing of Richard’s emails wasn’t a problem. With the exception of his June 5th email, Janice replied to him every other time, either the same day or the next. It’s hard to interpret this as anything other than a very welcome exchange.

Where we risk alienating someone is by nagging them for a decision when they’re not ready to decide, or aren’t in the position to decide due to factors beyond their control, or there’s been a change in priorities.

Between progress-check emails, intersperse valuable content that isn’t pushing for a decision, and you’ll be fine.

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Categories: Business Development, Communicating, Rainmaking, Well Said!
Originally published May 28, 2022
Last updated May 30, 2022
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Mike O’Horo Mike O'Horo

Known as “The Coach” throughout his long career, Mike O’Horo was a giant among his peers in legal marketing and business development. He trained more than 7,000 lawyers, simplifying powerful sales processes by which they generated $1.5 billion in new business. A serial innovator, earlier he developed RainmakerVT, a virtual BD training tool, and the sales training program ResultsPath. He wrote his column, “Well Said!,” on sales and business development truths for lawyers. Mike passed away in February 2022.

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