Why You Hate Selling (And How to Fix Your Offer So You Don't Have To).

You Don’t Hate Sales, You Hate Confusion
As a creative service provider, I’d bet you started your business because you enjoyed the work, not because you wanted to sit on endless sales calls, or bang your head against a keyboard trying to find leads to even sit on discovery calls.
Even if your offer is amazing, if you don’t know how to talk about it in a way that resonates with your ideal customers, it can feel like you're a sleazy car salesman trying to convince someone to buy a car they don’t actually need.
In The Breakroom this week, we hosted Pitchfest, our version of Shark Tank. We were surprised by how many times we heard, “Now I want to work with you,” from our members after someone finished pitching their offer.
People resonated with their pitches so strongly because they understood the problem, how the offer solved it, and why they were the best person to work with.
There are 9 things that we asked them to include in their pitches, and below we’ll break down those same 9 things (as a checklist) across 4 common red flags that’ll make your sales pitches easier.
Red Flag #1: You haven’t earned the right to pitch yet
There’s a common example used in business school that goes like this: “What’s the most important thing to get right if you want to run a successful hot dog stand?”
Most people will say things like “quality hot dogs”, “a recognizable cart”, or “a strong social presence”…but the simple answer is a starving crowd.
If you park your cart in front of a skyscraper at 12:00 PM, you don't need a better recipe—you just need to be there. You don't need to convince a starving crowd to eat.
When it comes to your offers as a creative service provider, there are 3 things that you need to get right before anyone will ask you what’s on the menu (ie: your offer):
Checklist 1: Who is it for?
You may have heard of this as your ICA (Ideal Client Avatar) or Customer Profile. The idea is that you want your offers to feel specific to them (eg: opening your hot dog cart in front of a specific building as everyone leaves for lunch).
At a minimum, what do your best customers have in common (demographics), and what are they trying to achieve (psychographics)?
Checklist 2: The Problem
Some problems may seem obvious (ie: if you’re getting married you need a photographer), but the better you can describe the problem the quicker your customers will feel seen by you (ie: capturing the special moments of your wedding so that you can be fully present, both now and in the future when you’re telling your kids about your wedding day).
Checklist 3: The Cost of Inaction
If someone doesn’t buy your service, what will happen? For the hot dog cart, it means walking blocks or hailing a cab to get to somewhere else that has food, possibly being late coming back from your lunch break. For your customers, it could mean missing out on speaking opportunities, not growing their business, or working in the evenings when they want to be spending time with their families.
Red Flag #2: Your client has no idea what they’re actually buying
People buy solutions, not projects.
If you're just selling “branding”, do your customers understand what that means, or how it’ll (actually) help their business?
In some ways, you can think of your sales process as a trailer for your full service. Taking it a step further, over the last few years, movie trailers have started to put a 3-5 second quick cut “trailer” at the beginning of a trailer to hook your attention to last through a 2-minute trailer.
Checklist 4: The Offer
People skim everything. Your offer name and 1-2 sentence description is the equivalent of those 3-5 seconds at the beginning of a trailer to hook the attention of a potential customer. By knowing your Who, Problem, and Cost of Inaction from Red Flag #1, you can talk directly to your people so that they’re immediately interested in the offer.
Checklist 5: Mechanism
Now that you have their interest, you have a “2-minute trailer” (sales page) to convince them to buy a movie ticket (your offer). Are you selling a fast-paced action thriller of an offer, or a slow and peaceful western with all the vibes?
Okay, enough movie references; this part looks like giving your process a name, and breaking down what the 3-5 biggest steps of the process are, with what they can expect to happen (eg: “We don’t just ‘design’, we go through our signature 3-step audit, build launch framework”).
Explaining the “how” of your offer is about starting to build trust with potential customers that you actually know what you’re doing, and that you know how to solve their personal problems.
Red Flag #3: You’re relying on “Quality” as your only differentiator
The fact that you do good work used to be enough to convince people to buy from you. We are in a trust recession and an economic downturn (depending on who you ask). People are now considering a lot more options when it comes to making purchases.
This part is all about making you stand out from the crowd, and stay at the front of mind for your ideal customers.
Checklist 6: Differentiation
The Purple Cow Theory in marketing (roughly) states that if you’re driving down the road and pass a herd of cows, most people won’t pay attention to them because they’re all the same & common. But if you passed a field that had a purple cow in it, most people would stop and stare.
You have different interests, skills, and life experiences. That gives you advantages that literally no one else has. Lean into what you can do better than anyone else, the things that you do differently, or how you don’t include certain things in your packages (and why).
Call out the industry status quo and how your offers deliver better for your clients.
Unless you’re intentionally creating a beef like Jimmy Kimmel & Matt Damon, try not to specifically call out other service providers in your differentiation strategy.
Checklist 7: Show Proof
Once people are paying attention, the fastest way to build trust is to show proof. This could be:
- Testimonials: “She’s the first person who created a marketing strategy that actually worked.”
- Metrics: “Clients see a 50% increase in inquiries within 90 days.”
- Volume: “We have helped over 100 clients re-brand their businesses.”
This may feel like a lot of work, but just build it into your process. Automate asking for reviews 2 weeks after your project ends. Or get permission to use their analytics anonymously.
Red Flag #4: You’re selling the plane, not the destination
When you’re going on vacation, are you making travel decisions based on the airplane you’ll be flying on?
Most people decide on their vacation based on things like beaches, ski slopes, or family that they’ll see once they step off the plane.
Your sales process should be the same way. Instead of wrapping up with “you’ll get 72 hours to choose which photos you want edited,” talk about the benefits: “you’ll be able to work from bed and wear sweatpants whenever you want, since you’ll have professional photos to use on your socials” (assuming this is a pain point of your clientele…).
Checklist 8: Transformation
If you can solve a problem & (honestly) tell them you can give them the life they’re looking for, signing the contract becomes a formality, and as long as your price isn’t ridiculous, they won’t think twice about what you’re charging.
A website build goes from being 5 pages, a blog & SEO, to being credible and an asset that’s generating customers.
A branding photoshoot goes from 4 hours & 200 photos, to elevating how both you and your customers see you as a professional leader in the nutrition & wellness space.
A clickup/notion/project management tool build goes from a dashboard & 4 integrations, to saving you 20 minutes at the beginning of every meeting with your team, since everyone is looking at the same numbers.
The more personal you can make your transformation to your Who, Problem, and Cost of Inaction - the more people will be banging down your door asking you to take their money.
Checklist 9: The Ask
The average person has over 6,000 thoughts a day.
Or a little over 14 seconds per thought (including while sleeping).
If you’re not making it easy for people to know what the next step is to work with you… They’ve probably already moved on to the next thought
A good CTA (call to action) reduces friction. It’s a tradeoff between Effort vs. Commitment. Asking someone to "Comment the word BRANDING" is low friction, so you'll get more volume (but you have to follow up). Asking someone to "Book a Call" is high friction; you'll get fewer people, but they will be much warmer leads. Choose the one that fits your capacity.
If you’re missing 2+ checklist things, we should talk.
When you get all 9 of these checklist items dialed in, your sales process can go from pulling teeth to half way through a sales call, people asking how soon they can start. They’ll know immediately that you get them, and know how to solve their problems… with the proof that backs it up.
The problem is, oftentimes it’s really hard to get these 9 things correct since you’re so in the weeds of delivering for your current clients, and struggle to zoom out far enough to get a clear picture.
That’s where other people come in handy, whether that’s a coach who can walk you through proven frameworks or fellow creative service providers who are on the same journey as you and can share what they’re learning.
We just launched a new coaching intensive called the Offer Accelerator, where we support female founders in building offers that are proven, profitable, and recurring. In 30 days, we’ll work with you to refine your offers with weekly done-with-you workshop-style sessions. If you’re interested in an intensive, send us a DM on IG @joandlyndon to get all the details.
- You can see our ongoing coaching offers here
- Or if a community is a better fit, check out The Breakroom our membership for Creative Service Providers to learn and build their businesses together
