How Do You Know If You’re Overpricing (or Underpricing) Strategic Work?
Let’s start with a question that comes up a lot–usually in a Slack thread, a voice memo, or a “can I run this by you?” conversation:
How do I actually price this?
We’re usually not talking about a brandscript. Or a website. Or something you’ve done 50 times before.
We’re talking about strategic thinking. The kind of work where you’re helping a client make decisions that shape their next 6, 12, 24 months (or more).
Because this is where things start to feel less clear.
You might be looking at a project thinking:
Is this a $5K engagement?
A $10K one?
$20K?
And even after you talk it through with someone, gut-check it, maybe run the numbers a bit… you still kind of land on a number and think:
I think this makes sense… maybe?
There’s usually a moment where you just sit with it for a second. Not in a dramatic way—but just enough to go, “Okay… is this going to land?”
What You’re Really Pricing in Strategy
When you’re pricing deliverables, there’s usually a baseline. You know roughly what a website costs. You know what a messaging project typically runs.
But when you move into strategy, that certainty fades. Because you’re no longer pricing something repeatable.
You’re pricing:
Your Ability to Diagnose the RIght Problem and Solve It
Experience that Expedites Clear Judgment
Pattern recognition
Decision-making
The ability to see what matters—and what doesn’t
And there isn’t a clean market rate for that. You can gut-check it. You can talk it through. You can even model it out a bit.
And at some point, you’re still just… choosing.
That’s the part that doesn’t really go away, even as you get more experienced. So the goal isn’t to find the “perfect” number.
The goal is to arrive at a number you can stand behind—based on how you’re interpreting the value. And how well you can communicate it.
Why the Same Project Can Be $5K or $20K
This is where most of the confusion comes from.
Two people can look at the exact same opportunity and price it completely differently, and both can make a case for their number.
I’ve seen people land on $5K for something that probably should’ve been $20K—
and I’ve seen the reverse too.
And the tricky part is… you can usually justify both, because they’re not actually pricing the same thing.
One might be thinking:
“This is a messaging project. I’ve done these before. Easy peasy”
Another might be thinking:
“This is going to shape how this company sells for the next year.”
Same scope.
Different interpretation.
Which is where this starts to feel less like math and more like judgment.
So What Do You Actually Do With That?
When I get stuck on something like this, these are usually the things I go back to.
Not as a formula—but just as a way to pressure test it.
1. How much does this decision actually matter?
If this work goes well, what changes?
Does it improve conversion slightly?
Or does it reshape how they go to market entirely?
The longer the impact lasts—and the more it affects revenue—the more the pricing should reflect that.
One example of this actually came from someone in one of our masterminds. She did an on-site with a client and realized they were a $2M company because they were positioned to solve small problems for their customers. They didn’t see the value they were providing for their customers. But after meeting with their leadership, she could see they had the ability to be a $100M company - and quickly. She repositioned them as such and now they are on their way to growth.
Was this a messaging project? Sort of.
Was this a strategic revolution in their business with exponential growth potential? Absolutely.
Her follow-up proposal to the client after the on-site was for fractional growth advisory, not messaging execution. That’s the shift. That’s the work of a high-value strategist.
2. How much ownership am I taking on?
Are you:
Contributing ideas?
Or responsible for the direction?
There’s a difference between:
“Here are some options”
And:
“This is the direction I recommend you take”
Ownership increases risk—and value.
Great advisors coach their clients to think deeply, but when the time comes to make a decision, they also aren’t afraid to stand behind a recommendation with conviction.
3. How clear is the problem going in?
If the client is saying:
“We need X”
That’s one thing.
If they’re saying:
“We’re not sure what’s wrong, but something isn’t working”
That’s another.
Ambiguity requires more thinking, more iteration, more judgment.
That should show up in the price.
4. How urgent is this—and what priority are they asking for?
This is one that people skip.
If a client wants:
Quick turnaround
High responsiveness
First-priority access
That has a cost.
At Heights, we’ve had conversations where a client asked for a fast turnaround and priority positioning. Specifically, they asked, “Can you make us your number one priority for the next 60-90 days?”
We told them plainly: That changes the price.
Because you can only realistically do that for two or three clients at a time. There’s only one first seat.
And to their credit—they said yes. But that only worked because it was clear what they were paying for.
And the engagement has been very enjoyable with everyone on the same page about the level of importance and urgency that we’re all working under.
5. Is the scope actually clear enough to price?
This is one I’ve had to learn the hard way a few times.
If you find yourself thinking:
“To make this worth it, I’d have to charge something kind of ridiculous…”
…it’s usually not the price that’s off.
It usually means:
The work is too open-ended
The outcome isn’t defined enough
Or you haven’t done enough discovery yet
In those cases, the move isn’t to inflate the price.
It’s to tighten the scope. To reduce the unknowns for both parties.
Or, break it into phases that you can price accurately.
Here’s an example: Our Heights team is currently working on a proposal for a large client for brand differentiation research and rebranding where the work will likely span 18 months. We’ve split it into 5 phases and provided broad ranges for each phases’ price. Each phase is concretely priced before we start it, but we don’t know how extensive the rebrand will be before we do the research. The client just wants to know how to budget for this kind of work and that we’re going to be thoughtful about the process and the measurable outcomes from the work.
Takeaway - can you break down the scope into smaller phases?
A Quick Reality Check on Clients
Most good clients aren’t trying to get the lowest number. They’re just trying to make sense of it. And they want to make sure the value is there.
They’re asking:
Does this add up?
Do I understand what I’m paying for?
Do I trust this person to deliver this outcome?
And if they can’t quite connect the dots, that’s where things start to feel expensive in the wrong way.
Your goal isn’t to “get away with” a higher number. It’s to make the price feel justified—and slightly uncomfortable in the right way.
Because if it’s too comfortable, it often means it’s not tied to meaningful change.
How This Connects to Your Pricing Model
If all of this still feels a little squishy, keep reading.
We don’t recommend jumping straight from hourly pricing to pure value-based pricing.
At Heights, we tend to work from a hybrid approach:
Start with effort (time, team, complexity)
Then calibrate based on impact, ownership, and context
If you want a deeper breakdown of how to actually do that, we unpack it here:
Because the goal isn’t to guess. It’s to build a pricing approach that reflects both what it takes and what it’s worth.
Closing Thought: Pricing Is a Judgment Call
At the end of the day, pricing strategic work isn’t about landing on a perfect number.
It’s about making a judgment call.
One that reflects:
The weight of the decision
The level of responsibility you’re taking on
And the impact this work is meant to have
You don’t always get this perfectly right. I don’t think anyone does. But you do get better at knowing why you chose the number you chose.
And that part matters a lot more than being exact.
