6 Brutal Questions to Ask Before Starting a Community on Skool

6 Brutal Questions to Ask Before Starting a Community on Skool

I’m gonna be real with you right from the jump… not everyone should be starting a community on Skool right now.

I know that’s probably not what you wanted to hear. You’re excited, you’ve been watching other people build thriving communities, and you’re ready to dive in. Trust me, I get it.

But here’s the thing nobody else is telling you flat out—launching before you’re ready is going to waste your time, your money, and honestly? It’s gonna frustrate the hell out of your members.

I’ve been there. I’ve seen what happens when you launch too early, before your foundation is solid. And spoiler alert: it’s not pretty. Your members feel abandoned, your trust gets damaged, and you end up working twice as hard to rebuild what you could’ve gotten right the first time.

So before you set up that Skool community and send out invitations, let’s do an honest self-assessment together. We’re checking six critical things that need to be in place before you launch—and by the end of this, you’ll know whether you’re ready to move forward or if you need to pause and get some foundational clarity first.

There’s no shame in either answer. Better to know now than to launch and struggle.

Question 1: Do You Actually Know Who You Serve?

And I’m not asking if you have a vague idea like “entrepreneurs” or “women in business.”

I’m asking if you can describe your ideal members so clearly that you could literally pick them out of a crowded room. That literal.

Because here’s the thing about starting a community on Skool—you cannot build it for everyone. It won’t work. When you try to serve everyone, you end up serving no one. Your messaging gets all watered down and generic, and nobody feels like “oh, this is for ME.”

In my community, people tell me all the time: “Dee, you’re reading my mind.” That’s not magic. That’s avatar clarity.

What Avatar Clarity Actually Looks Like

So how clear do you need to be? There are three things you gotta nail:

First, understand their demographics—their age, income level, where they’re at in life. The concrete stuff.

Second, know their psychographics—their fears, their desires, what keeps them stuck at 2am when they can’t sleep. The emotional stuff.

Third, and this is the real test: can you describe them in one sentence?

Let me show you what this looks like in practice. My avatar is Jasmine. Jasmine is a woman earning between $55K to $85K a year who has valuable knowledge and experience. She wants to build a digital product business, but she’s completely overwhelmed by the tech side of things. She’s tired as hell of hustle culture and wants to build something sustainable that doesn’t require her to work 80 hours a week.

See how specific that is? I can see Jasmine. I can feel her frustration. I know exactly what she needs and what she’s struggling with.

That’s what you need before you start building on Skool.

When you have this level of clarity, your content makes people say “Oh my God, this is exactly me. How did you know this?” But when you don’t have it? People read your stuff and just scroll past because nothing’s hitting. Nothing’s sparking recognition.

The test is simple: Can you pick your ideal member out of a crowded room based on who they are and what they need? If not, you’re not ready to build just yet. You gotta do some avatar work first.

Question 2: Do You Have a Clear Promise?

And by promise, I mean the transformation you’re offering—not what you’re teaching, but what they GET.

What changes in their life because they joined your community? What’s different now that you’re in it?

Your promise is the before and after state. It’s the gap between where they are now and where they want to be later. That bridge? That’s your promise.

For me, my promise is this: I help regular women build real digital product businesses using simple systems, creativity, and AI that actually makes their life easier—without the tech overwhelm or the hustle.

It’s specific. It’s clear. It’s transformational.

What Doesn’t Work (And Why)

Here’s what doesn’t work: vague promises that sound safe but attract no one.

Things like:

  • “We help entrepreneurs succeed” (Okay… how?)
  • “Community for moms” (Cool, but what do they get?)
  • “Support for business owners” (What kind of support?)

See, vague promises feel safe because you think they’ll attract more people. But the truth is, vague promises attract NO ONE. Nobody hears that and thinks “Yes, that’s what I need!”

Specificity is what sells. When you’re specific about the transformation, the right people say “That’s it. That’s what I’ve been looking for.” And the wrong people? They move on. Which is exactly what you want.

How to Craft Your Promise

Let me walk you through how to do this. It’s actually pretty simple, but you’ve gotta be thoughtful.

Step 1: Identify the problem. What are they struggling with right now?

Step 2: Define the transformation. What do they want instead? What does success look like for them?

Step 3: Bridge the gap. How does your community get them from point A to point B?

Your promise should be one clear sentence that answers all three of these pieces. If you can’t articulate it simply, you’re not clear enough yet.

And honestly? If you’re struggling to nail this down, that’s a sign you might not be ready to launch. Work on your messaging first. Get crystal clear on what you’re actually offering before you ask people to join.

Question 3: Do You Have Consistent Messaging?

This one trips people up all the time.

You might have avatar clarity and a solid promise, but if your messaging is all over the place—talking about fifteen different things in fifteen different ways—nobody’s gonna know what you actually stand for.

Consistent messaging means three things:

Your voice: How you talk, your personality, your tone. Is it consistent across everything you create?

Your values: What you believe in, what you stand for, what you won’t compromise on. Can people articulate your values after following you for a week?

Your point of view: Your unique perspective on your topic. What do you see differently than everyone else in your space?

When I show up, whether it’s in my emails, my community posts, or my Instagram stories, you know it’s me. The voice is consistent. The values are clear. My point of view—that regular women can build successful digital businesses without tech overwhelm or hustle culture—comes through in everything.

That consistency builds trust. And trust is what keeps people engaged in your community.

If your messaging is scattered, if you’re changing your angle every week, or if people can’t quite pin down what you’re about, you’re not ready to build a community yet. Get your message tight first.

Question 4: Do You Have Content Depth?

Here’s a question that’ll tell you everything you need to know: Could you talk about your topic every single day for years without running out of things to say?

Because that’s what running a community requires.

You need enough depth in your knowledge and passion for your topic that you can consistently show up with valuable content, answer questions, provide insights, and keep the conversation going.

This isn’t about being the world’s leading expert. But you do need to be able to go DEEP on your topic. You need layers. You need perspectives. You need enough substance that you’re not repeating yourself after month two.

Think about it honestly:

  • Can you answer questions about this topic without Googling every answer?
  • Do you have personal experience solving the problems your members face?
  • Can you provide multiple approaches or frameworks, not just one way of doing things?
  • Do you genuinely enjoy talking about this topic, or does it feel like work?

If you’re struggling to come up with content ideas already, before you’ve even launched, that’s a red flag. You might love the IDEA of having a community around this topic, but do you love the topic itself enough to sustain it?

Be honest about this one. Your future self will thank you.

Question 5: Do You Actually Want to Hold Space for People?

Okay, this one’s about energy, and it’s where a lot of people realize community might not be their model.

Holding space means being present emotionally. It means answering questions, celebrating wins, and supporting people through their struggles. It means creating a safe environment where people can be vulnerable. And it means showing up even on days when you don’t feel like it.

Because here’s what they don’t tell you about starting a community on Skool: you’re taking on people’s burdens, their struggles, their stress. They’re coming to you because they’re stuck, and they need help. That’s beautiful—but can you hold it?

Do you have the emotional capacity for it?

The Honest Assessment

Let’s get real about what this requires:

Do you genuinely enjoy helping people? Like, does it energize you or drain you?

Can you handle people’s emotions? Every community comes with frustrations, setbacks, and emotional moments. Can you hold space for that?

Are you okay with being needed? Some people don’t like “needy” people. But as a community leader, your members are going to need you to lead. Is that something you can handle?

Do you have the capacity to be consistent? Not just with content, but with emotional availability.

Here’s the truth: if holding space sounds exhausting before you even start, community might not be your model right now. And that’s completely okay.

You can build a successful digital product business with courses, templates, workshops, or a digital product store. You don’t necessarily need the community aspect of it.

But if you love connecting with people? If you light up when you get to help somebody and see their transformation? If you thrive on building relationships? Community is going to be the most fulfilling part of your business.

Through hell and high water, the highs and the lows, my community is the best part of my business. It keeps me alive and keeps me going.

You have to know yourself. Be honest about what energizes you versus what drains you, then build accordingly.

Question 6: Do You Have Time for Simple Cadences?

Notice I said “simple,” not “complicated.”

You don’t need hours every day, but you do need to be consistent. Here’s what a simple rhythm looks like for starting a community on Skool:

Daily check-ins: 10-15 minutes. Going in, filtering to see if you missed anything, reading comments, making a post, liking people’s content, helping your members. Just showing up.

Posting frequency: At minimum, two to three times a week so people know you’re active and engaged.

That’s it. We’re talking about an hour or two a week total commitment at minimum.

Now personally? I post every single day in my community because my community is the heartbeat of my business. I dedicate about 30 minutes to my check-ins. I’m in there posting one to two times minimum every day. I’m checking the dashboard analytics, making sure I’m answering questions, going through to make sure I don’t miss anybody’s comments.

But that’s me. You need to figure out what’s sustainable for YOU.

Be Brutally Honest With Yourself

Can you realistically add this to your schedule? Do you have the mental space for it? Are you in a season where you can actually sustain this thing?

Because here’s what I want you to really hear: launching a community just to abandon it because you didn’t have the capacity is worse than not launching at all.

Your members are gonna feel that abandonment, and it damages trust. I can tell you this from experience—some trust falls off, and it takes you working extra hard to build that back. Take it from somebody who’s been there and done it already.

If you’re already burned out, overwhelmed, or stretched too thin, this might not be the right timing. Get some things off your plate first. That’s not failure—that’s wisdom.

Wait until your season changes, then start building that part of your business when you’re actually ready to put in the time necessary.

The Final Readiness Check: Do You Have All Six?

Let’s bring this all together.

You need ALL six of these pieces before starting a community on Skool:

  1. Avatar clarity: Knowing exactly who you serve
  2. Clear promise: Defining the transformation (the before and after)
  3. Consistent messaging: Your voice, your values, your point of view
  4. Content depth: Something you can talk about every day for years
  5. Energy to hold space: A genuine desire to support people emotionally
  6. Time capacity: A simple, sustainable rhythm you can maintain

If you answered yes to all six? You’re ready to move forward. Keep going. You’re building something amazing.

But if you said no to even one of these? That’s your answer.

And listen, there’s no shame in that. Work on that foundational piece first. Get clear. Get ready. THEN launch.

Why This Matters More Than You Think

Community is incredible when you’re ready for it. But it’s an absolute disaster when you’re not.

I’ve watched people launch communities too early and burn out within three months. I’ve seen trust get damaged because leaders weren’t prepared to hold space. I’ve witnessed beautiful ideas fail simply because the foundation wasn’t solid.

You know what’s worse than waiting to launch? Launching and failing because you skipped the foundational work.

Your future members deserve a leader who’s ready. Your future sanity deserves a foundation that’s solid. And your business deserves to be built right the first time.

So be honest with yourself. If you’re ready, amazing—go build that community. If you’re not quite there yet, that’s okay too. Do the work. Get the clarity. Build the foundation.

The community will still be there when you’re ready.

And if you need help getting that avatar clarity, defining your transformation, or building out those foundational pieces? The Sis, Just Launch It AI Toolkit includes AI prompts specifically designed to help you nail down your messaging, understand your ideal member, and create a clear promise that actually converts. Think of it as your strategic co-pilot for getting all six of these pieces locked in before you launch.

Because honestly? Starting a community on Skool without clarity is like building a house without a blueprint. You might get something standing, but it won’t be what you envisioned—and it definitely won’t last.

Do the work now. Launch when you’re ready. Your community will be better for it.

Hey, I'm Dee

Digital Product AI Creator & Mentor