How to Master DM Sales Without Feeling Gross (The Human-First Approach)

If you are a creative service provider, there is a good chance you have a complicated relationship with selling. We know the feeling of dreading the "DM slide." We’ve all been on the receiving end of those generic, copy-and-paste pitches that have absolutely nothing to do with us, and the last thing we want is to make our own audience feel that way. The fear of coming across as "sleazy" or ruining a potential relationship often stops us from taking any action at all.

What if selling in your direct messages didn't have to feel gross? What if it could actually be a joyful, deeply connected experience?

We sat down with Kendra (@kendraashtoneducation) on The Sustainable Creator Podcast (@thesustainablecreator) to ask how. She is a family and wedding photographer, a former corporate recruiter, and a business coach for photographers. Kendra brings an incredible, refreshing perspective to this topic, largely because 85 to 90 percent of her own sales come directly through Instagram DMs.

Her secret? It’s a 100% human-first approach. In business, if you pursue the human first, the sales will naturally follow. Here is a breakdown of how you can master DM sales, build authentic relationships, and finally get out of your own way when it comes to selling.

Listen to the full episode of the Sustainable Creator Podcast here:

The Mindset Shift: "Simmering" vs. "Boiling"

When creative business owners hit a low sales month, panic usually sets in. You feel an urgent need to increase the bottom line, which often leads to rushing your sales activities.

Kendra beautifully describes this anxious energy as a "rolling boil". When you are boiling, you operate with urgency, expecting everyone to love your offer immediately. It feels similar to going to the grocery store when you are hungry, everything looks good, and you buy too much; you want to convert in every DM conversation because you feel desperate for a sale. This forced energy never feels good for you or your potential client.

Instead, the goal is to "simmer". A simmering approach to sales is peaceful, fun, authentic, and aligned. It means you are constantly building relationships over time without turning the heat up to a stressful level. By actively and consistently connecting with people, you are stacking the bricks of your foundation long before you ever ask for a sale.

The 3 Levels of Listening (and How to Use Them in the DMs)

To successfully simmer, you need to actually listen to your audience. When we are stuck in our own heads looking for a sale, we only consume their words to see how it benefits our business. To fix this, you have to elevate how you engage. In the episode, we broke down a classic executive coaching framework: The Three Levels of Listening.

Here is how those levels apply directly to how you show up on Instagram:

Level 1 Listening: This is where you hear the words coming at you, but you are only doing the bare minimum to participate in the conversation. On Instagram, this translates to passively tapping through someone's stories or scrolling past their feed without ever interacting.
Level 2 Listening: At this level, you are showing visual cues that you are engaged, like nodding your head. In the digital world, Level 2 is liking a story, interacting with a poll, or dropping a quick emoji reaction. It says "I am here," but it doesn't open the door for much else.
Level 3 Listening: This is the gold standard. Level 3 is where you actively ask follow-up questions because you care enough about what the person shared to take a genuine interest. On socials, this means taking that half-step further to actually reply to a story with a thoughtful message starting a conversation instead of waiting for them to come to you.

Having a conversation in the DMs should feel like playing a game of tennis. If you are the only one hitting the ball over the net, it’s not fun for anyone. Use Level 3 listening to grab a racket and hit the ball back & forth.

How to Start Genuine Conversations (Without Being Weird)

So… what do you actually talk about if you aren't supposed to pitch your services right away? You talk about them.

Take an interest in their real lives. However, you must avoid the "creepy marketer" trap of trying to forcefully connect random parts of their life to your offer. For example, if someone posts that they like the color orange, do not slide into their DMs to ask if they want to wear orange in a brand photoshoot. That is just weird.

Instead, use these two natural entry points:

Encourage them: Every single person on the planet needs more encouragement. Compliment their work, tell them a certain color looks great on them, or uplift them.
Ask for help: Humans naturally love to help others and provide value. If you see them doing a hobby or using a product you genuinely want to know about, ask them for their advice.

As you build these relationships, remember the 80/20 rule for your own content. Aim for your stories to be about 80% personal, real-life content, and 20% active business offers. Showing your humanness does not erase your expertise or professionalism. In fact, it invites people in and builds trust.

Frictionless Booking: Keep Them in the App

When a genuine relationship naturally transitions into a sales conversation, your priority must be to eliminate friction. As business owners, we often build systems for our own comfort, like a 10 question inquiry form, rather than making it easy for the client to purchase.

From a neuroscience standpoint, 95% of purchasing decisions are emotional, while only 5% are logical. If a potential client is excited and messaging you in the DMs, do not send them to a link on your website. As soon as they have to click away and wait for a page to load, they shift from an emotional state to a logical one, and you risk losing the sale.

Kendra equates this to having someone over for dinner at your table, but telling them to go pick up to-go food somewhere else. Stay at the table. Keep graphics of your packages and pricing saved directly on your phone so you can send them right in the chat. Only move them out to a client portal or email after they are ready and have made their payment.

Handling Ghosting Gracefully

Even with the best intentions, conversations will stall. When someone "ghosts" you, it is vital that you do not internalize it or let it trigger your own feelings of rejection.

In an anonymous survey Kendra conducted regarding ghosting in the photography industry, 100% of respondents said they never actually meant to ghost the business owner. Usually, they either didn't realize they needed to respond because the business owner never asked a question, or life simply happened and their mental filing cabinet got too full.

When you follow up, you must use language that removes any accidental shame or embarrassment. If they feel awkward, they won't come back.

Follow-Up Best Practices:

Follow up a maximum of two times, and keep it in the same platform where you were originally talking.
Use a gentle phrase like, "Hey, just popping this up on our radar" to show that you are in this together.
Always end your messages with a specific question (e.g., "Does option A or B serve your family best?") to give them an easy way back into the dialogue.

If they still don't answer, just unpin the conversation from the top of your DMs, accept that they are a little cold for now, and return to engaging with them simply as a human.

Your First 100 Days: The DM Sales Action Plan

If you want to revamp your sales strategy and commit to this human-first approach, here is the roadmap for your first 100 days:

Study Humans: Become obsessed with understanding the real, daily lives of your audience so you know exactly when and how they might need your offer.
Identify the Symptoms: Write out the specific symptoms and hardships your clients face right before they need your services. This acts as your diagnostic tool so you know exactly when to confidently offer a solution.
Audit Your Communication Skills: Send a message to the people who know you best and ask them how you communicate most effectively. If your strength is speaking, lean into sending voice memos.
Remove the Barriers: Send your booking process to someone completely outside of your industry and ask them to try booking you. If it's difficult for them, remove the barriers until booking with you feels incredibly simple.

Selling in the DMs doesn't have to be a dreaded chore. When you let go of the rigid timelines, embrace your own humanness, and simply focus on serving the person on the other side of the screen, you will watch your business—and your joy—grow exponentially.

Are you wanting to dive deeper into these psychology-backed sales strategies to fix your cash flow slumps? Kendra is actually our guest speaker inside of The Breakroom for March, and we are going to be diving even further into the metrics and tactics that we couldn't fit into this podcast episode!