The Pricing Conversation That Changed Everything

Hey there,

Last week, I had a fascinating conversation with a fellow fractional CTO that made me rethink everything about pricing conversations.

He'd been stuck in the hourly billing trap, constantly justifying his time and feeling guilty about every invoice. Sound familiar?

Then he made one simple shift that transformed his business: he stopped selling time and started selling outcomes.

Here's what that looks like in practice:

When a prospect asks about your rates, resist the urge to quote an hourly figure. Instead, redirect the conversation to value with questions like:

• "What would it mean for your business to solve this problem?"

• "How much revenue are you leaving on the table right now?"

• "What's the cost of not addressing this issue?"

The key is to anchor your fee against the value you create, not the hours you work.

I recently used this approach with a healthcare startup. Instead of discussing my hourly rate, we talked about the $2M in revenue they were losing annually due to technical debt and system inefficiencies.

Suddenly, my $10K monthly retainer didn't seem so steep. In fact, it was a bargain compared to the value at stake.

This isn't about charging more (though that often happens naturally). It's about aligning your compensation with the impact you deliver.

Here's how to structure these conversations:

1. Start with the "what and why." Understand their desired outcome and why it matters.

2. Quantify the impact. Help them put concrete numbers around the opportunity or problem.

3. Present outcomes, not hours. Offer different levels of engagement and support.

4. Focus on results. Set clear expectations about what they'll achieve, not how many hours you'll work.

Remember: You're not a contractor selling time. You're a leader selling outcomes. 

The moment you internalize this shift, pricing conversations become remarkably easier.

What's your approach to pricing conversations? Hit reply and let me know - I'm always curious to learn from you.

To knowing your worth,
Lior

Lior Weinstein 
Founder & Head Coach, CTOx