Anchor & Orbit Small Biz Advice: Cold Emails?!

We here at Knit Wit love us some Sarah Schulweis, the founder and head-honcho of business consultancy Anchor & Orbit. So much so, in fact, that we thought Sarah ought to have her own little piece of Knit Wit—a place to answer all of YOUR big, burning questions about getting out and getting on your feet as a small business person. And, because we’re starting out cold with our first-ever column with Sarah, we decided to start with a super-apt and very relatable question about cold emails and first impressions (as in, making good ones). Read on and find out why, no it’s actually not that scary and yes, you should consider sending them.

Hi Sarah,

I finally took the plunge and I am officially freelance full-time. The clients who were once my side hustle are now my full focus. It’s scary, but I’m enjoying the freedom, and frankly, the clarity of not being so scattered.

I know that some of the ongoing client work will keep me afloat, but I am hoping to create some kind of pipeline or, better yet, a financial buffer so if my client relationships change, I’ll be prepared. Here my question:  I know I have to start marketing myself, specifically doing outreach. This is totally new for me and I am really struggling. How do I start doing outreach without being too sales-y? Help!

Thank you, Resistant but Persistent

Wonder how many uncomfortable self-introductions Anna Wallack, founder and designer of Misha + Puff has had to send in her time… (Photo by Susie Cushner for Knit Wit Issue 5)

Wonder how many uncomfortable self-introductions Anna Wallack, founder and designer of Misha + Puff has had to send in her time… (Photo by Susie Cushner for Knit Wit Issue 5)

Resistant but Persistent,

Woah! Huge congratulations to you! The world of freelance is lucky to have you. You seem to have your head on straight and know what you need to make this work. First of all, I hear more about this problem (or fear) more than almost anything else. Toggling between the work you do every day to the work that keeps your business running is one of the most difficult parts about being independent, whether it’s freelance, small business, entrepreneurship, or whatever you’d like to call yourself.

I know you’re asking about cold emails to potential clients, but I look at businesses holistically, so I need to make sure you have a few things in order as you start to build your business. The below will really help you when it comes to professionalism, which is what your client is looking for, especially in a new freelancer (i.e.: more risk without a track record, no matter how long you worked in your prior job.)

Consider some of these assets:  

  • Website / Social / Marketing - nothing fancy, but if you can afford design and some customization, it makes a big difference in the eyes of clients who, frankly, don’t know who the eff you are. Testimonials of any kind are gold. Simple social media effort works and so does consistent and targeted outreach.

  • PDF overview of your work - when we talk about cold emails, I’ll reference this. Clicking on an attachment in an email keeps people in their inboxes, not distracted AND is a quick peek to prove you’re as talented as you say you are.

  • Systems -  contracts, payment terms, delivery time, will all be something your client will ask you about so have those answers (or decisions for yourself) ready.

  • Work hours/response times  - boundaries will save your life. Decide how you want your week to look and don’t forget to build in some lunchtime, times to work out your body, and times when you are not looking at a screen.

The Cold Email

In my experience, and because of the nature of my work, cold emails have nearly never worked. But that’s just me! When people are ready to work with me, they’re looking for my service and find me through asking their friends and searching for articles. If they aren’t ready and looking, the concept of working with a business consultant is too new (or cold) to even try to pitch. What has worked is my happy clients talking about the solid work I do with other people. When those referrals come my way, I make sure I have all of the assets I listed above and below ready to go.

Whatever your business is, do take how your customer wants to find you into consideration. For example, if I grow my services to be more workshop based for bigger companies, I think cold emails will end up being a huge part of building that aspect of my business. For now, what has worked is getting a warm introduction from my network to companies or people I have wanted to work with.

(Sidebar! We can talk about retainer clients another time, but long-term contracts are also going to be a huge part of how to stay sane and cashflow positive)

Ok ok. The cold email. The below outline should be three short paragraphs with a closing line AT MOST.

Photo by Susie Cushner for Knit Wit Issue 5

Photo by Susie Cushner for Knit Wit Issue 5

  1. Get a warm introduction if you can

  2. A simple headline, like “Copywriter looking to work with [Insert Company Name]”

  3. Keep it short

    • Brief introduction

    • Tell them how you’re going to improve their business

    • Tell them about your services/expertise

  4. Link out to your website AND include a PDF of your services & expertise (it might seem redundant, but think of it as thorough instead)

Upon response:  Create another short email and include a link to book a call with you. This system is a HUGE time (and fumble) saver.  Calendly is great, but I know there are a few other services that will help people book you automatically. Assume your client is busy - make their life easier from the get go.

In regards to being to sales-y:

Let this fear go. You have to talk about yourself and what you do to get work. But the key is that the people who are hiring don’t care who you are per se - they are already short on time and are looking for help. They care about what you can do for them and that you’re not going to steal their money. Ask them questions about the business to clarify your understanding of what they might need, and tell them how you’re going to help them.

Bad sales tactics are when you promise too much or (the worst offense) pressure people into saying “yes.” If you are telling the truth and are honest about what you can do, good clients will respond to that. Oh, and spell/grammar check everything.

Good sales tactics are to get them on the phone swiftly,  listen with intention, tell them what you can (and can’t) do. Once they are interested, send a proposal as soon as you can (or if you’re swamped, tell them when they can expect it and send it on time.) If they are ready to move forward, send the contract and invoice quickly. Once they’re in and saying yes, get the paperwork done and the deposit in motion. Even those who are ready and willing have a tendency to back out.

Honestly, setting realistic expectations and delivering above and beyond will help you with your future sales cycle in a big way. Happy clients lead to happy referrals.

And have fun!


Sarah Schulweis is the founder of Anchor & Orbit Consulting and works with her team of experts to help businesses and creative professionals find their path to growth. Sarah believes that to create an effective strategy, you must have internal clarity about your values and motivation. And that maybe, just maybe, creativity can only happen when you understand your finances.