If you’ve ever thought, “I don’t know who to talk to,” that’s exactly why your DMs feel awkward.

Most people assume the fix is a better script, a better opener, or a list of perfectly polished lines to copy and paste, but that’s not the real issue.

The real issue is that you’re trying to have sales conversations without a clear process and without the right people in the room.

When you don’t know who you’re for, every DM feels like you’re guessing.

You second-guess what to say, you overthink how to say it, and you either avoid the conversation completely or you over-explain until the other person disappears.

I’m Lisbeth Graham, a messaging and sales strategist for mission-led service-based business owners, and since 2023 I’ve helped over a dozen women sell in the DMs with confidence without feeling salesy or needing a script.

What I want to show you in this post is the simple framework behind “DM sales that feel natural,” so you can stop freezing up when someone says, “Tell me more about what you do.”

The first step to selling in the DMs without feeling weird is making sure you have the right people in your DMs in the first place.

I once talked to a woman who told me that 50% of her DM conversations led to nothing, and at first she thought, “That’s not that bad.”

But when you actually think about it, it’s a big deal.

If you’re spending an hour talking to someone who was never meant to buy from you, that’s an hour you can’t get back. It’s not just time, it’s energy.

And if you’re building a business to make money (not turn this into a hobby), your connections need to be intentional.

Random conversations with random people will always create random results.

This is why target audience clarity matters so much.

When you know who your ideal client is, you stop trying to convince everyone, and you start talking to the people who already have the problem you solve and already want the outcome you offer.

If you’re reading this and you’re like, “Okay, but I’m not even sure who my target audience is,” then you don’t need to push harder in the DMs yet.

You need to get clear first.

That’s exactly why I created the Spark the Conversation Challenge, which is a free 5-day challenge designed to help you identify your target audience in a practical way.

For 20 minutes a day, for five days, you’ll do simple actions that lead you into real clarity, and by the end you’ll have a copy mining blueprint you can use for your messaging, your sales pages, and your content, using the actual words your audience is using.

That matters because the fastest way to make DMs feel “awkward” is trying to sell to people you don’t understand, using language that doesn’t match what they actually care about.

Clarity fixes that at the root.

The second step is starting a personal connection before you make it about business.

Most people don’t want the first conversation to feel like a transaction, and honestly, even in in-person networking, I don’t open with “So what do you do?” because you are more than your business.

I want to know about you. I want to know what brought you here, what you’re trying to build, what you’re dealing with, what you actually want.

If someone tells me they’re a mom, I’m going to ask about their kids. If they’re homeschooling, I’m going to ask what that looks like for them.

That personal connection lowers the pressure and makes the conversation feel human instead of salesy. It also helps you stop treating the DM like a place where you have to perform.

Your job in the beginning is to connect and understand, not to pitch.

Now, there are moments where a conversation starts with business, and that can absolutely lead to a sale quickly, but that’s not the norm for most people most of the time.

I’ve had situations where someone resonated with something I posted and said, “This is me,” and I messaged them right away with genuine support, and they signed up that same day.

That happens when your message is refined and your content is already doing the work of pre-qualifying people.

But for most mission-led service providers who are building consistency, it’s better to assume you’re playing the long game.

When you remove the expectation that someone needs to buy immediately, the conversation gets less awkward because you’re not trying to force an outcome. You’re simply building trust and gathering information.

That brings us to the third step: treat every conversation like market research.

Every DM is data. Whether it becomes a client today, a client later, a referral, or simply a learning moment, it still helps you get better at selling because it helps you understand your audience.

This is why questions matter so much.

If someone says, “I’m scared of selling in the DMs because I don’t want to come off as salesy,” you don’t need to rush to fix it or defend yourself.

You can ask, “What makes you feel like you’d sound salesy?” and let them talk.

That question alone opens the door to deeper insight and gives you language you can use in your messaging later.

When you lead with curiosity, the DM becomes softer, slower, and more productive, and you stop feeling like you have to carry the whole conversation on your back.

Once the conversation has developed and it’s clear they want to learn more, the next layer is what I call permission-based selling.

This is one of the biggest reasons people feel awkward in DMs: they start pitching without consent.

They send a novel about what they do, list every feature, drop a price, and then wonder why the other person ghosts.

The fix is simple: ask permission. “Would you like to hear more about what I do?” “Would you mind if I shared what my offer looks like?” “Do you want more information?”

This keeps the other person included. It signals respect. It also helps you avoid pouring your energy into someone who isn’t actually interested or isn’t actually a fit.

And yes, you need to be picky. Being “for everyone” is how you end up with nightmare clients, mismatched expectations, and a business that drains you instead of supporting you.

When you do share your offer, lead with the transformation before the price.

Price without context makes people shut down.

Transformation helps people understand why it matters.

So instead of “It’s $500,” you explain what they’ll walk away with, what changes for them, and what support is included, then you share the investment, and you bring the conversation back to them with a question like, “How does that sound?” or “What are your thoughts?”

That keeps the conversation collaborative instead of one-sided.

If they need time, that’s fine. You can follow up. The fortune is in the follow-up, and it’s completely normal for someone to take weeks or months to warm up, especially in a market where trust is low and budgets are real.

To implement this right away, here’s your homework:

Start 3 intentional conversations and ask one simple market research question. If you don’t know what to ask, the Spark the Conversation Challenge includes questions you can use.

You can literally say, “Hey, I’m doing a little market research for an offer I’m refining. Would you mind if I asked you one question?”

Some people will say yes, some will say no, and that’s okay. The win is that you’re building the skill of connecting, listening, and leading with questions, which is the foundation of selling in the DMs without feeling salesy.

And as you keep practicing, the awkwardness fades because you’re no longer guessing—you’re using a process that simplifies everything.

If you’re ready to take the next best step in your messaging, join my monthly membership The Phoenix Experience. Click the link for full details!