Why you can’t book outbound meetings

In today’s issue, I will break down the failure of many SDRs to book outbound meetings.

Booking outbound meetings is more challenging than ever, mostly because money isn’t flowing as it used to. Prospects are careful with their budgets, and they are reluctant to take calls with stressed out sales reps.

But if you’re in sales, you still need to book meetings and to generate pipeline.

So today, I’m going to break down the 3 most common mistakes I see sales reps making with outbound prospecting, and what I’d recommend they do instead.

Mistake #1: Writing essays

I’m writing this newsletter right after a training session I gave to 20 sales reps. We went through their cold emails and they were making the same mistake as 99% of people I train.

Their emails looked more like essays, with convoluted sentences, buzzwords, and way too many words.

Imagine receiving a cold outbound message and having to spend time deciphering it. You would do it once and ignore every email that remotely looks similar.

This is what prospects are doing, and the reason you can’t get replies.

Mistake #2: Being inconsistent

Consistency is 80% of your success in cold outbound. Most sales reps I train have no prospecting routine when I first meet them, and those who choose to create one see quick results after a few days.

Here’s a typical week of an inconsistent SDR:

  • Monday: Spend hours looking for 100+ new prospects

  • Tuesday: Send a first touchpoint to a part of their list

  • Wednesday: Send the remaining touchpoints to their list

  • Thursday: No replies, 100+ follow-ups

  • Friday: Still no replies, slowly becoming desperate

If this schedule looks familiar, then you’re doing something wrong.

Mistake #3: Not focusing on existing accounts

The last type of mistake I see all the time is the result of the “growth at all cost” model that was predominant in the tech industry until Q1 2022.

The last 5 years were exceptional in terms of funding, and the goal of most high-growth companies was to acquire new logos. If they could show that they were able to open new accounts, they’d get money. As a result, SDRs have been exclusively dedicated to opening new accounts.

However, things are different nowadays. If you can’t expand new accounts, you’ll have a hard time generating new opportunities, and you will miss your targets.

Instead, here’s what you can do:

The first thing you need to do is to reduce the size of your cold outbound messages. Write messages with 3 to 4 sentences that can be easily read on a smartphone without scrolling. For example:

Mary, saw you changed position around 5 months ago.

What are you doing to prevent your team from turning off prospects with pushy LinkedIn messages?

If you’re into it, I’d love to share a quick video on how your team can start genuine conversations with prospects on LinkedIn.

Should I send it over?

Second, build a prospecting routine. I wrote a detailed article on how to do that here.

Finally, review your strategy and start focusing on existing accounts. I started doing it a few weeks ago, and I have already booked 5 meetings and closed one deal with this strategy.


  • Don’t write essays

  • Don’t be inconsistent

  • Don’t ignore existing accounts

  • Do write short messages

  • Do prospect every day

  • Do focus on upsells and cross-sells

I hope this helps!



P.S. When you’re ready, here are 4 ways I can help you.
  1. Build your outbound prospecting system from scratch here (230+ students)
  2. Write cold messages that get a 38% reply rate and 27% meeting rate here (40+)
  3. Book me 1:1 or for your team here
  4. (NEW!) Sponsor my newsletter & get 3K+ eyeballs on your ad!

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