The Three Conversations You’re Avoiding (That Are Keeping You Small)

You know what's keeping you stuck at $2M ARR?

It's probably not your product roadmap. It's probably not your pricing strategy or your go-to-market motion or any of the things you're spending hours obsessing over in your pitch deck.

It's three conversations you're not having.

I've spent 20 years building and scaling product orgs, and now I work with founders trying to make the same leap. The pattern I keep seeing? Three conversations that don't get had. I watched one of them paralyze a company I worked at for six months. I've seen another one cost a startup the senior hire they desperately needed. And the third one bleeds revenue every single month while founders tell themselves it’s fine.

Pro tip: It’s not fine. It’s never fine.

You're not having these conversations because they feel risky, or uncomfortable, or like they might blow up in your face. So you keep putting them off. You keep working around them. You keep compensating.

And every day you don't have these conversations, you're making the same choice: stay founder-led, stay small, stay stuck in the weeds.

I'm not going to tell you these conversations are easy. They're not. They suck. But I am going to tell you that on the other side of each one is a version of your company that can actually scale, and a version of yourself that can actually step into being CEO instead of being chief everything officer.

Here are the three conversations, what they cost you when you avoid them, and how to actually have them.

You’ve got someone who was employee number three. Rode or died in the early days. Worked weekends, believed in the mission, took below-market salary because they bought into the vision. Maybe they’re still a good human. Maybe you still like grabbing coffee with them.

But they’ve topped out.

The role needs something different now than it needed two years ago. Back then you needed someone scrappy who could figure things out with duct tape and hustle. Now you need someone who can build systems, manage a team, operate at a different altitude. And this person can’t make that leap, or won’t, or just doesn’t have another gear.

I watched this play out when I was SVP of Product at a growth-stage SaaS company. The founding engineer had been promoted to CTO. Brilliant developer, built the entire early platform. But he had zero interest in managing people, zero interest in assessing platform risk, didn't even want to have opinions on core architecture decisions.

At a leadership offsite, we brought in a consultant to help improve team dynamics. The consultant asked the CTO about technology strategy. His response, in front of the entire leadership team: "That's not my job."

The consultant's jaw dropped. The president spent the next ten minutes trying to convince him that yes, having opinions on core technology was literally the CTO job. He didn't buy it.

That misalignment stalled the entire organization for six months. Software development ground to a halt. Product managers and engineers were constantly demoralized because nobody was running the ship. We couldn't hire senior engineering talent because candidates would interview with this guy and realize there was no technical leadership.

Everyone knew it wasn't working. But nobody wanted to have the conversation because he'd been there from the beginning and built everything. So instead of dealing with it directly, the company eventually brought in a VP of Engineering to do the actual CTO job while the CTO kept his title, coded in his basement, and complained about everyone.

That's the cost of the workaround. You spend six hours a week compensating for gaps. You can't hire the people you need. Your team loses respect for leadership that won't make the hard call. And eventually you wind up with a Frankenstein org chart that makes no sense to anyone, where everyone knows what's happening but nobody's allowed to say it out loud.

First, get clear on what the role needs now versus what it needed two years ago. Write it down. Be specific. This isn't about them being a bad person or a bad employee. This is about the gap between what the company needs and what they can deliver.

Then book 30 minutes with them. Not your usual 1:1. A separate thing. And open with: "I want to talk about where your role is headed and make sure we're aligned."

Here's what you're not doing: you're not opening with criticism. You're not dumping a performance improvement plan on them out of nowhere. You're not hedging with a shit sandwich. You're being direct about the gap between what the role needs and where they are.

Walk through the specifics. "The role now requires someone who can manage a team of five, who can build scalable processes, who can operate with less hands-on direction from me. Here's where I see the gap." Give examples. Real ones. Recent ones.

Then give them a choice. Maybe there's a different role that fits their actual strengths. Maybe they can grow into what the role needs if they're willing to do the work, and you're willing to invest in coaching or training. Or maybe it's time for them to find something that's a better fit.

The key is not making the choice for them. Lay out the reality, lay out the options, and let them decide. But be clear about the timeline. "I need to know by the end of next week how you want to move forward."

If they step up, great. You now have a roadmap and expectations. If they don't, or if they can't, you've given them agency in how they exit. Most of the time, they already know. They've felt the gap. They've been waiting for you to acknowledge it.

And once they're out or transitioned to a different role, you can hire the person you actually need. The person who doesn't need you to be the safety net. The person who removes you from the critical path instead of adding you to it.

You’ve got a customer who’s been with you since the early days. Maybe they were one of your first ten customers. Maybe they gave you the case study you needed to close your next five deals. They’ve been paying $500 a month for the past two years.

The problem is that plan doesn’t exist anymore. You’ve added features, you’ve improved the product, you’ve moved upmarket. New customers are paying $2,000 a month for what this customer is getting. And you keep telling yourself it’s fine, they earned it, they took a chance on you when you were nobody.

Every month they stay at $500 is $1,500 you’re leaving on the table. That’s $18,000 a year from one customer. Multiply that by however many customers you’ve grandfathered in, and you’re probably looking at $50K-$100K in ARR that you’ve just decided to give away.

But it’s worse than that. Because every time you look at your pricing, you see this weird exception. And it makes it harder to think clearly about what you should charge. It makes it harder to have the pricing conversation with your team. It creates this precedent that pricing is negotiable, that loyalty means never having to pay full price.

And meanwhile, you need that revenue. You’re trying to hire. You’re trying to scale. Every dollar you leave on the table is a dollar you can’t invest in growth.

Start by pulling the data. What are they actually using? What features have you added since they signed up? What are comparable customers paying?

Then reach out. Email is fine for this. You’re not ambushing them. “Hey, wanted to give you a heads up. We’re updating pricing for all our early customers to reflect the product changes over the past two years. Here’s what that means for you.”

Lay out the new pricing. Explain what they’re getting now that they weren’t getting before. Give them options: they can upgrade to the new pricing, they can move to a plan that makes sense for their usage, or they can walk. But the $500 plan is going away.

Here’s the key: frame this as bringing them into alignment with the rest of your customer base, not as punishing loyalty. “We want to make sure everyone is on pricing that reflects the value they’re getting.” That’s it.

Most of them will upgrade. Some will negotiate a middle ground. A few will walk. The ones who walk probably weren’t your ideal customer anymore anyway.

Your ARR goes up, obviously. But more than that, you’ve cleaned up an exception that was making it harder to think clearly about your business. You’ve set a precedent that pricing reflects value, not history. And you’ve freed yourself from the guilt of leaving money on the table every month.

This one’s the hardest. You started the company with someone. Maybe you’ve known them for years. Maybe they’re your best friend. Maybe you couldn’t have gotten here without them.

But the company has outgrown what they’re good at, or what they want to do, or maybe you’ve just realized that the role they’re in doesn’t make sense anymore. And you’re stuck. Because this isn’t just an employee, this is a co-founder. You can’t just have a performance conversation and move on.

I was recently in conversations with a Series A company about a product leadership role. Brother-sister founding team, good traction, interesting product. But they'd kind of tapped out their addressable market and were trying to figure out what came next.

In the first conversation, it became crystal clear they weren't aligned on where the company should go. Not small tactical disagreements - fundamental strategic misalignment about the direction of the product and the business. And they had no idea how to work through it.

I turned down the opportunity. Not because it wasn't good on paper, but because I knew that misalignment would mean every product decision would become a referendum on their relationship. I'd be stuck in the middle of a co-founder dynamic that hadn't been resolved. For all I know, they were still working through something that happened when they were six - maybe he flushed her Polly Pocket down the toilet and she's been holding a grudge for thirty years. I have no idea, and I don’t care to know. But it was painfully obvious to me that I didn't want to be the person trying to build a product roadmap in the middle of it.

Here's what that cost them: they couldn't hire a senior product leader. And if they can't hire someone at that level, they probably can't hire a VP of Sales or a VP of Marketing either, because anyone with experience is going to see the same dynamic and walk away.

Your team sees it too. They don't respect someone who's coasting on a title. They come to you with questions they should be asking your co-founder, because they know your co-founder won't give them a real answer or won't make a decision or just won't do the work. And the people you need to hire to scale? They see it, and they don't take the job.

You're running two companies. The one you're actually building, and the one where you're working around your co-founder. Maybe they're supposed to be running sales but they're not, so you're doing it. Maybe they're supposed to be running product but every decision still comes to you. Maybe they're just checked out, collecting equity and salary, but not actually contributing.

And you can't hire around them. You can't bring in a real VP of Sales if your co-founder is technically the head of sales. You can't build the leadership team you need because there's a co-founder-shaped roadblock in the way.

This one doesn’t start with a meeting. This starts with you getting really clear on what you want the outcome to be. Do you want them to step into a different role that fits their strengths? Do you want them to step back to advisor? Do you want to buy them out? You need to know before you start the conversation, because this isn’t one conversation, it’s a series of them.

When you’re ready, schedule time off-site. Not at the office. Not over Slack. Somewhere you can have a real conversation without interruption.

Open with: “I want to talk about how we’re working together and whether the current setup is working for either of us.”

Then be honest. Not mean, not accusatory, but honest. “Here’s what I’m seeing. You’re spending a lot of time on X, but the role really needs Y. I wind up doing Y, which means I’m not doing Z. This isn’t working for me, and I don’t think it’s working for you either.”

Give them space to respond. Maybe they’ve been feeling the same way. Maybe they’re burned out. Maybe they want to step back but didn’t know how to bring it up. Maybe they think everything is fine and this is going to be a shock.

Then work through the options together. What role actually makes sense for them? What role do they want? Is there a way to restructure that works for both of you? Or is it time to part ways?

This conversation probably doesn’t get resolved in one sitting. But starting it is the thing. Because every day you don’t start it is another day you’re stuck running around them instead of building with them.

If you can find a new structure that works, you've removed a massive source of friction. You're no longer working around each other. You're no longer splitting responsibilities in ways that don't make sense. You can hire the people you actually need.

If you can't, and they step back or leave, you've freed yourself to build the leadership team you need. You can bring in the VP of Sales who's actually going to close deals. You can bring in the product leader who's actually going to own the roadmap. You can stop being the person who does everyone else's job.

These conversations share something in common: they all require you to choose the company’s future over someone’s feelings in the present. That sounds cold. I get it. But here’s the thing: avoiding these conversations doesn’t protect anyone’s feelings. It just spreads the pain out over months or years instead of concentrating it into one hard conversation.

The early employee knows they’re not keeping up. They feel it every day. Your silence just makes them wonder if you’ve noticed, or if you’re too much of a coward to say anything.

The grandfathered customer knows they’re paying a fraction of what everyone else pays. Some of them feel guilty about it. Some of them just assume you’re bad at business.

The co-founder knows things aren’t working. They’re either in denial or they’re waiting for you to bring it up.

Having the conversation gives everyone agency. It lets them make a choice about what happens next instead of just waiting for the other shoe to drop. And it lets you move forward instead of staying stuck in a situation where everyone knows something’s wrong but nobody wants to be the one to say it.

You don’t scale by being nice. You scale by being honest. There’s a difference.

The companies that make it from seven figures to eight figures are the ones where the founder is willing to have the hard conversation instead of working around it. They’re the ones where the founder chooses clarity over comfort.

So here’s your homework: which of these three conversations are you avoiding? Write down the name. Write down what it’s costing you. And then book the meeting.

It’s going to be uncomfortable. But so is staying stuck.​​​​​​​​​​​​​​​​