In my conversations with revenue leaders and founders, one question trumps them all: How do I make better decisions for my organization? If you can make better decisions, everything else in the organization gets better.
When you're responsible for an entire revenue organization, the decisions you make cascade throughout the company. A poor choice can waste months of effort, burn precious capital, and damage credibility—while a brilliant one can unlock tremendous value, create competitive advantages, and rally your team.
This week, I had the opportunity to speak with Ashley Grech, CRO at Xero, about how elite leaders approach problem-solving. With experience scaling revenue organizations at Square (where she grew sales contributed revenue by 10X), Recharge, and now Xero, Ashley has developed a systematic approach to diagnosing problems, prioritizing solutions, and implementing change.
You Don’t Get Paid to Say ‘No’
Early in our conversation, Ashley shared a perspective that immediately resonated: "I solve problems for money. I don't get paid to say no; I get paid to say how."
This mindset shift (from seeing obstacles as roadblocks to viewing them as puzzles to solve) is the foundation of enterprise value generating leadership. And it's not just about individual capability.
"Problem solving is an unappreciated discipline, particularly in revenue," Ashley explained. "Revenue leaders have good instincts, but that's not quite enough."
Three principles guide her approach to problem-solving:
Diagnosis: Finding the Real Problem
Before attempting to solve any problem, you must first diagnose it correctly. Ashley uses a powerful framework called the "driver tree," which is a diagnostic tool similar to what product leaders might recognize as an "opportunity solution tree” (a tool from Teresa Torres that I teach my leaders).
The driver tree starts by breaking revenue down into its fundamental components:
From there, you drill deeper, asking "why" at each level to identify root causes. For instance, if deal progression is high but you still lose 20% of deals in implementation, you might need to examine your handoff process, expectation setting, or onboarding process.
This structured approach transforms vague symptoms into specific, actionable insights:
"When you have visibility into all parts of the revenue engine," Ashley noted, "you can make more intelligent decisions. It's like an airline cockpit with check engine lights."
The Decision-Making Process: From Gut to Data to Gut
I’ve found myself referencing this framework from Ashley multiple times since we recorded. It’s one of my favourite takeaways from any episode so far because it’s so simple yet powerful. Ashley recommends a three-step approach to decision-making:
This "gut → data → gut" framework ensures you're neither ignoring important signals nor chasing every fleeting concern.
The Prioritization Puzzle
Every revenue organization faces the same constraint: more good ideas than bandwidth to implement them. How do you decide what to tackle first?
Ashley uses four factors to prioritize problems:
Where most leaders go wrong, according to Ashley, is being swayed by noise rather than signal.
"Customer noise or employee noise might not be the first order of business," she explained. "A feature complaint on your stickiest product that isn't affecting churn rates may be less urgent than an onboarding bottleneck preventing new client acquisition."
This echoes what Kevin Dorsey calls distinguishing between "volume and volume"—is an issue truly high-volume, or just loud? You can hear more in Episode 2 of the pod.
Making Decisions: Beyond the First Right Answer
As Farhan Thwar (Shopify's head of engineering) once said on Lenny’s Podcast, "There are probably 10,000 right options for any problem, and everybody stops at the first right one."
Ashley believes most complex problems don't have a single right answer—and approaching them with this mindset is limiting. Instead, she recommends a principled approach to decision-making:
"Before I enter a call, I'll write down what I want the solution to actually solve for. Most of the time, it has to solve for multiple things."
For example, when deciding on a new compensation plan, Ashley established core principles first:
These principles become your evaluation criteria. Any solution that doesn't meet them gets eliminated, narrowing down options while ensuring alignment with strategic goals.
Implementation: Making Change Stick
Perhaps most importantly, Ashley emphasized that even the best solutions fail without proper implementation. A principled approach helps here too:
"When you disagree with someone, always start with what you agree on," she advised. "When you're rolling out a new comp plan or changing rules of engagement, there will inevitably be teams or individuals who disagree. But if you agree on core principles like 'we are here for our clients' and 'we're stewards of our company,' no one will disagree with those things."
This approach transforms your solution from something imposed on your team to something built on shared values.
Teaching Your Framework to Others
One of the most valuable aspects of a principled approach is that it allows you to scale your decision-making beyond yourself. Ashley recommends a three-step process:
"If you either co-create or author the principles yourself," Ashley explained, "the answer that comes back is much closer to the percentage of done. If you give pure white space, you'll get an answer that is at best 50% of what you wanted. But if you give people the framework, you're much more likely to get 80-90%."
Problem Solving Example: International Expansion
When it comes to tackling complex challenges like market expansion, Ashley recommends a strategic, incremental approach rather than going all-in immediately:
"One mistake I see is people going straight to 'we should put people on the ground there.' I'm not sure that's always the right option."
Instead, she suggests creating "packets of investment"—structured tiers that allow you to test markets before fully committing:
This approach allows you to validate assumptions, build momentum, and self-fund expansion without overcommitting resources.
"It's easy to say 'this is the biggest economy, so we should go after that one,' but that's lazy thinking," Ashley noted. Sometimes entering a smaller, adjacent market first (like Ireland from the UK) allows you to build momentum, improve payback periods, and fund entrance into larger markets.
Similarly, timing matters for channel expansion. Ashley identifies three key triggers:
What Makes a Great CRO
As our conversation concluded, I asked Ashley what separates good CROs from truly great ones. Her answer was striking in its simplicity:
"A great CRO is a truly enterprise leader. One that can think about problems beyond revenue and knows how to solve their peers' problems in legal, in product, in finance, as well as their own."
This ability to transcend functional boundaries and drive enterprise value—not just hit revenue targets—is what distinguishes elite revenue leaders.
Three final pieces of advice stood out:
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