Abbey Woodcock: “How To Be Great At Sales Without Seeming Salesey”

Do you know your business could be much bigger than it currently is, but aren’t sure how to get there? I can help!

Sales has a bad reputation even though it’s a critical part of our economy and survival. Sales doesn’t just mean convincing someone to buy something. It means convincing your kids to eat their vegetables or your spouse to take you to the restaurant you like or your mom to stop worrying. It means selling your attention and your value to all kinds of people.

As a part of my series about how to be great at closing sales without seeming pushy, obnoxious, or salesy, I had the pleasure of interviewing Abbey Woodcock.

Abbey Woodcock has been a direct response copywriter since 7th grade when she wrote a 30-page sales letter asking her crush to the dance. Since then, she’s converted better… writing sales pages and emails you’ve probably read from some of the biggest names online.

Now, she teaches the business side of creative freelancing including setting up systems to grow a freelancing business and building out an in-house content team that seamlessly “gets” your voice.

She’s also a chainsaw instructor and mom to 2 awesome kiddos in Upstate NY.

Thank you for doing this with us! Before we dig in, our readers would like to learn a bit more about you. Can you tell us the “backstory” about what brought you to this career path?

I’ve been in marketing and copywriting for about 12 years now. About 5 years ago, I discovered that most freelancers focused on getting really great at their craft but weren’t so good at the “business side” of their business.

This includes finding and closing clients. Most creative freelancers had no idea how to systematically find potential clients and what to do once they connected. I developed the Socratic Close sales system, a way to have a “sales call” that’s tremendously valuable to the potential client and positions you as an authority — even if you have less experience, no samples, or case studies to share.

Can you share with our readers the most interesting or amusing story that occured to you in your career so far? Can you share the lesson or take away you took out of that story?

A couple of years ago, I became a client rather than a freelancer and saw the “other side” of sales calls. I had calls with about a dozen copywriters. That really showed me how poorly most freelancers were at closing deals.

I’d been where they were many times and would have killed for a client to tell me why I didn’t land the gig. So that was the start of my sales training.

I put together a list of seemingly simple pieces of advice like “have a professional email address” and “be on time to the call.”

It was fascinating to me that so many people were missing these basic fundamentals.

Are you working on any exciting new projects now? How do you think that will help people?

There’s a lot of confusing and conflicting information out there for freelancers right now, especially when it comes to COVID-19, the government stimulus package, and other benefits. We’ve created a comprehensive guide for freelancers about all the government and non-profit benefits freelancers may qualify for. We break down each benefit — what it is, how to know if you qualify, and how to get it.

We’re updating it daily and giving it to freelancers for free so that they can be informed. Our mission has always been making creativity sustainable and now more than ever that is a critical mission.

Also, after working with hundreds of freelancers over the past 5 years, I’ve created a methodology for freelancers to “go pro” in their business. We work with freelancers who want to step up their business game when it comes to the legal, financial, and operations parts of their business. We take freelancers through a 5-part assessment and then shore up those areas through a 6-month program.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

In my life, nobody has had a bigger effect on my business than Kevin Rogers of Kevin helped me discover what it is I love to do and build a freelancing career from that. He has an amazing talent for finding the “hidden talents” in freelancers and then illuminating the path to building a career from those talents.

He’s always been a huge cheerleader for me and central to my success. I’d highly recommend a conversation with Kevin for anyone that isn’t sure if they have the chops or the experience for success in freelancing. He’ll shine a light on talents and skills you took for granted or didn’t even know you had.

For the benefit of our readers, can you tell us a bit why you are an authority on the topic of sales?

I’ve personally closed over a million dollars in sales for my own business using my Socratic Close methodology and thousands of freelancers have used it as well.

As a copywriter and marketing consultant, I’ve helped my clients close over $25 million in sales. Core to my approach is selling in your own voice. You DON’T have to sound like a used car salesman in order to apply principles of behavior psychology and sales to your copy and your conversations.

Let’s shift a bit to what is happening today in the broader world. Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the COVID-19 pandemic have understandably heightened a sense of uncertainty and loneliness. From your experience, what are a few ideas that we can use to effectively offer support to our families and loved ones who are feeling anxious? Can you explain?

Anxiety is a completely normal and acceptable feeling right now. For freelancers especially, there’s so much uncertainty in the normal day-to-day that is just exacerbated in today’s business climate. One thing that I have been telling my clients is that as business owners, we need to be drivers. And what I mean by that is that we need to be people who make things happen, not people who things happen to.

We can’t just be reactive, we need to focus on what we can control and move those things forward. Freelancers are in a great place to be agile in their businesses and now is the time for it. We can’t feel bad about selling or buying right now. As business owners WE are the economy and we need to keep money moving. We need to earn money and spend money.

Ok. Thanks for all that. Let’s now jump to the main core of our interview. As you know, nearly any business a person will enter, will involve some form of sales. At the same time, most people have never received any formal education about how to be effective at selling. Why do you think our education system teaches nearly every other arcane subject, but sales, one of the most useful and versalite topics, is totally ignored?

Sales has a bad reputation even though it’s a critical part of our economy and survival. Sales doesn’t just mean convincing someone to buy something. It means convincing your kids to eat their vegetables or your spouse to take you to the restaurant you like or your mom to stop worrying. It means selling your attention and your value to all kinds of people. But when you start to teach behavioral psychology and the psychology of sales, people get extremely uncomfortable. It feels wrong or manipulative.

But manipulation doesn’t necessarily mean bad. Kids need to eat vegetables and if you can manipulate them to do that, they are better off for it.

Sales and behavioral psychology are tools. Of course you can use any tool for good or for evil.

This discussion, entitled, “How To Be Great At Sales Without Seeming Salesey”, is making an assumption that seeming salesy or pushy is something to be avoided. Do you agree with this assumption? Whether yes, or no, can you articulate why you feel the way you do?

I wholeheartedly agree that you don’t have to be (nor should you be) pushy during sales. I don’t agree that all sales is pushy. When we buy something we love, we feel good about it. There was likely a sales process that moved us along that path, but it felt good.

Buyers’ remorse comes when we are pushed along a path we don’t want to be on. When we spend money but feel confused or even regretful about it. That’s the result of poor salesmanship. Unfortunately, when we talk about “sales” that’s the first thing that comes to so many people’s mind.

The seven stages of a sales cycle are usually broken down to versions of Prospecting, Preparation, Approach, Presentation, Handling objections, Closing, and Follow-up. Which stage do you feel that you are best at? What is your unique approach, your “secret sauce”, to that particular skill? Can you explain or give a story?

In my sales, and how I train my community uses what I call the “Socratic Close” method. Instead of presenting a solution, you’re digging deep on identifying the problem that your prospect is facing. You do this by asking questions and allowing the prospect to tell you about what is going on in their business or life.

Then, all your presentation becomes is asking more questions and repeating back what they say. The result is that the prospect feels heard and that you understand their problem on a deeper level than any other person they’ve talked to or considered working with.

It instantly eliminates competition without feeling like you have to “sell yourself,” brag, or talk down about competitors. It feels really natural and pleasant for both sides of the conversation.

Lead generation, or prospecting, is one of the basic steps of the sales cycle. Obviously every industry will be different, but can you share some of the fundamental strategies you use to generate good, qualified leads?

The best way to get in conversation with great leads is to understand deeply what your prospects are looking for. And I don’t mean the service you provide. I mean the outcome you provide. For me, clients aren’t really looking for copywriting or words. They are looking for more sales. If I can show someone during the lead generation process that I know how to get that outcome, they don’t really care about the process I use to get there.

I don’t have to talk about previous results or brag about headline formulas. I just have to show them that I understand their business and I know how to solve the problem they have.

In my experience, I think the final stages of Handling Objections, Closing, and Follow-up, are the most difficult parts for many people. Why do you think ‘Handling Objections’ is so hard for people? What would you recommend for one to do, to be better at ‘Handling Objections’?

The first step in “handling objections” is to understand what those objections are going to be. Some people have this idea that they are going to get on the call and their prospect is going to have some surprise objection that they won’t know the answer to.

In truth, every industry only has about 5–7 core objections you need to overcome. You can list those out and develop answers for them well before the end of the conversation. For prospects looking to hire copywriters, those objections are usually how much it costs, finding a writer who can write in their voice, and how long it will take. I can talk about these concerns early in the conversation so they understand the process and why they shouldn’t be concerned about any of these.

Addressing common objections early helps the prospect feel at ease and again, feel heard and understood.

‘Closing’ is of course the proverbial Holy Grail. Can you suggest 5 things one can do to successfully close a sale without being perceived as pushy? If you can, please share a story or example, ideally from your experience, for each.

1. Closing doesn’t just happen at the end of the conversation. The first thing people can do is create “mini closes” throughout the conversation. I’ve heard this called “building a yes train.” When you ask questions and then truly listen to the client, you can repeat back what they say. For example, a client may tell me that they don’t believe their sales page is converting. So I might ask, “why do you feel like it’s not converting?” or “what would you like the conversion number to be?” Then I just repeat back what they said, “Ok, it sounds like you have a 3% conversion and you’d like it to increase to 5%, is that right?” They’ll say yes. Then I’ll ask another question. “When we achieve that, what would that mean in terms of revenue?” When they answer, I just repeat it back again. “Ok, it sounds like increasing your conversion percentage from 3 to 5% would mean an additional $50,000 per month, is that correct? Great, so over a year, that’s worth $600,000 to you. I just want to make sure my math is right.” They feel heard and I’m building my sales case as we go.

2. The close should just be a summary of what we talked about. When I send a proposal to the client, there’s nothing surprising in it. It’s simply a summary of the problems we identified, the solutions I can offer and the logistics of pricing and timeline. I summarize what they said in their own words. Too many people make the mistake of guess or predicting what the client wants. Just ask them! They’ll tell you. People love to talk about themselves, especially when it comes to problems they are facing.

3. Enthusiasm can handle a lot of objections. My goal on every sales call is to fall in love with the client and the project. If I can’t, then it’s probably a bad fit. By digging into what they are doing, I start to get excited about how I can help. And I communicate that with them. People are nervous to invest in other people. A great way to combat that is to be genuinely excited about what your client is doing and who they are. People want to work with people who understand them and are as passionate about solving this problem as they are. It puts clients at ease and makes them feel like you are the best solution because you care about them.

4. If you’re scared of pricing, don’t talk about pricing on the call. I take a good cop/bad cop approach to contracts and invoicing. My job as the salesperson is to fall in love with the prospect and make the prospect fall in love with me. Then price is just a detail. My go to line at the end of a call is

“I am so excited to work with you. I think we can do amazing things together. If it was up to me, I’d do this for free and start tomorrow. But my project manager gets real mad when I promise that. Let’s do this. I’ll take all the notes, get together with my project manager and send you a proposal in the next 24 hours. That will summarize what we’ll do and include all the pricing and timeline information. If you have any questions when you get that, we can hop on another call. Sound good?”

I’ve never had a potential client say no to this because it’s a completely reasonable request.

5. The proposal document should just repeat back what we said on the call, using the prospects own words. I use a 4-part proposal. 1) what they said the problem is 2) the solution I propose 3) how the solution happens 4) logistics of pricing and timeline. They read the proposal and it feels like I read their mind because I’m using their own words. Nothing is surprising.

Finally, what are your thoughts about ‘Follow up’? Many businesses get leads who might be interested but things never seem to close. What are some good tips for a business leader to successfully follow up and bring things to a conclusion, without appearing overly pushy or overeager?

There’s a few ways to address the long-tail follow up.

  1. Ask early how urgent a problem this is for the client to solve. If they don’t want to solve it now (they are just “window shopping”), then it’s probably not a great lead after all.
  2. Put an expiration date on your proposal. At the bottom of every proposal, I have a 7-day expiration date and the line, “Our schedule does fill up quickly and we regret that we can’t hold dates without your go-ahead and payment.” This encourages them to get the ball rolling
  3. A few days after the proposal if I haven’t heard anything, I send a 9-word email (credit to Dean Jackson for this approach). This email just says, “Hey NAME, are you still interested in hiring a copywriter?” and nothing else! It makes it nearly impossible for the client to ignore and restarts the conversation around timeline.

As you know there are so many modes of communication today. For example, In-person, phone calls, video calls, emails, and text messages. In your opinion, which of these communication methods should be avoided when attempting to close a sale or follow up? Which are the best ones? Can you explain or give a story?

I love video calls for closing sales and email for follow up. So much of sales is building trust and seeing someone’s face allows the enthusiasm to come through and really builds trust in a way that email and phone just can’t do.

For follow up, I love email because you can hammer out logistical details as well as keep a running timeline of the conversation.

Ok, we are nearly done. Here is our final “meaty” question. You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

I believe my reason for having this business is to make creativity sustainable. For me, that comes from arming creative freelancers with the resources they need to be professional business owners that are in control of their own story and their own success.

Already, creative freelancing is a huge movement and I’d love to have a world where more people living lives where they are doing meaningful work as well-being time and location independent.

How can our readers follow you online?

My website is here:

I am on twitter here:

I am on Instagram here:

Thank you for the interview. We wish you only continued success!

About the author:

Mitch Russo started a software company in his garage, sold it for 8 figures and then went on to work directly with Tony Robbins and Chet Holmes to build a $25M business together. Mitch wrote a book called “The Invisible Organization — How Ingenious CEOs are Creating Thriving, Virtual Companies” and now his 2nd book called Power Tribes — “How Certification Can Explode Your Business.” Mitch helps SaaS company founders scale their own companies using his proprietary system. You can reach Mitch Directly via [email protected]

Abbey Woodcock: “How To Be Great At Sales Without Seeming Salesey” was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.

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