A surprisingly long list of all the ways we sabotage our own success

At a networking event recently, I heard some variation of “Oh we struggle with pricing”from every business leader I met. While this struggle is shaped differently depending on the team and stage of the company, here are nearly three dozen reasons I continually hear from seed-stage to PE-backed leadership, from product to services. 

Which of these have you experienced directly?

Customer Intelligence Gaps

1. We don’t know precisely who our best customers are.
2. We don’t know enough about our customers’ operations.
3. We don’t know enough about our customers’ goals & strategies.
4. We don’t know enough about what our customers’ value most.
5. We don’t know enough about our customers’ other business expenses.
6. We don’t know what customers are currently paying for equivalent help.
7. We’re undercounting the number of people in the customers’ org we can help.
8. We haven’t considered ‘What if customers are wildly successful due to our help?’.

Internal Money Beliefs

1. We’re applying our own biases and sensitivities about money to our customers.
2. We’re uncomfortable talking about money at all – let alone when meeting a prospect for the first time. 
3. We’re uncomfortable saying large dollar amounts out loud.
4. We’re uncomfortable saying large dollar amounts out loud in front of prospects.
5. We can’t imagine our offering being worth that much.
6. We’re insecure about the implications and expectations if someone actually does pay that much.

Competitive Misunderstanding 

1. We’re assuming our competitors are far more sophisticated at pricing than we are.
2. We’re assuming our customers expect us to price like our competition.
3. We’re defining our competitive set far too narrowly.
4. We’re defining our competitive set from our perspective, not our customers’ perspective.

Value Proposition Articulation Failures

1. We can’t yet articulate a compelling value proposition in the customers’ own words.
2. We’re defining our value proposition much too narrowly.
3. Our value proposition requires customers’ enthusiasm for an unproven technology.

Pricing Model Misalignments

1. We’re assuming there’s only one way to price.
2. We’re assuming the offering must have a single price for everyone.
3. We’re assuming the offering must have a single price everywhere.
4. We’re assuming pricing must remain static for any period of time.
5. Our pricing model conflicts with the value delivery model.
6. Our pricing model conflicts with how customers want to pay.
7. Our pricing model conflicts with how many customers we can actually support.
8. We lack a structure to evaluate pricing after every sale.

Build-First Mentality

1. We assume price is driven by our costs to deliver, not the other way around.
2. We’ve accumulated inventory before securing purchase agreements.
3. We waited until the offering was perfect before asking customers if they want it at all.
4. We’re underestimating how long it takes to get in front of customers.
5. We’re underestimating how long it takes to complete a single successful sale.

¯\_(ツ)_/¯

1. We don’t know where to start to improve our pricing, so we keep not starting.