How on earth do you get people to respond to your outreach (without feeling slimy, sales-y, or overly self-promotional)?

A reader writes in asking about outreach.

Specifically, how on earth do you get people to respond to your outreach messages (without feeling slimy, sales-y, or overly self-promotional)?

In the outreach campaigns I run for myself (and for my consulting clients), there are a few essential rules I’ve picked up over time.

One of the most important – and often overlooked – rules is that you want to start with small asks.

Often (too often) an outreach sequence starts with a Large Ask:

  • “Can we have a call?”
  • “Will you sign up for this with your credit card?”
  • “Do you want to buy this from me?”
  • “Can you answer this intimate question about your business for me, a virtual stranger?”

If your ask is too massive, people will ignore it and ignore your message.

To show empathy for and understanding of the person reading your message, start with a small ask. Make your ask as specific and relevant to the person you’re emailing as possible.

Something in this vein often works well:

Can you answer this one question about…? I’ve already tried A and B, and I’m reaching out to you because of C.

Then, if they reply, keep the conversation going. Follow a stair-step pattern and ask larger questions over time and as you build up the relationship.

That could look like:

  • Can you answer this one question over email?
  • Can I ask a pair of follow-up questions over email?
  • Would you offer feedback on this idea?
  • Are you open to getting on a short 15-minute audio call (I’ll share an agenda w/ 3 questions)
  • Can we jump on a video call, and I ask you a few questions?
  • Hey, I’m going to be in (city) in a few weeks. Would you like to meet up for coffee near your office?
  • You’ve mentioned (problem) a few times. That’s something I specialize in solving for my clients. Are you up for a conversation about how I might be able to help you?

You’re starting with small asks first (

Then, as the relationship starts to form, you’re asking progressively more substantial and more significant asks.

By the way, if you’re struggling to get replies to your outreach emails (or, you aren’t sure where to get started with outreach), you’ll want to grab a copy of The Outreach Blueprint (

In The Outreach Blueprint, you’ll have a system you can follow to:

  • Email people and start a conversation with them
  • Stimulate future conversations around their pains and problems
  • Turn those initial conversations into an opportunity to see if they’re interested in your services

Outreach, at its heart, is about understanding the needs and wants that the other party is experiencing and stimulating a conversation around helping them by solving that problem.

And The Outreach Blueprint is your guide to polite, persistent outreach (