A Guide to High Stakes Decisions with Ashley Grech, CRO of Xero

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.

Listen to Ashley's episode on Apple and Spotify.

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:

1. It's impossible to have seen it all. You cannot rely solely on firsthand experience forever. How do you build confidence in scenarios you haven't encountered before?
2. Don't run the same playbook. Even if symptoms look similar from company to company, the root causes might differ significantly. You need to understand root causes before applying solutions.
3. If you can model it, you can teach it. This is key to scaling yourself and your impact. Teaching others your framework allows your organization to solve more problems without you becoming the bottleneck.
   

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:

• Quantity (deal volume)
• Quality (deal size)
• Conversion rates
• Velocity (time to close)
  

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:

• Is inbound volume too low to hit targets? That leads you to marketing.
• Are outbound leads not getting past discovery? Listen to calls to identify whether it's a value prop, skill, or targeting issue.
• Is deal progression high but implementations failing? Examine product or onboarding processes.

"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:

1. Start with Gut - Pay attention to qualitative signals. When topics repeatedly come up in customer conversations or you notice competitors winning more deals, your instincts may be flagging an issue worth investigating. Staying close to the front lines and your customer are key here.
2. Dive into Data - Use your driver tree to examine trends and validate whether your gut instinct represents a real problem or just noise. Try to get to root cause.
3. Apply Judgment - Recognize that you'll rarely have 100% of the information you need. As Jeff Bezos famously noted, "Most decisions should probably be made with somewhere around 70% of the information you wish you had. If you wait for 90%, in most cases, you're probably being slow."

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:

1. Resource constraints: What can be tackled effectively with current team and budget? Sometimes you simply don't have the right team to tackle a problem at that time.
2. Linchpin problems: Does one issue unlock many others? Small fixes with high impacts get priority. Ask yourself: "Is this a linchpin problem?"
3. Impact vs. effort: Focus on problems with the biggest potential revenue impact within a reasonable effort level. At Xero, they literally scope problems to dollar values when possible.
4. Strategic alignment: Does it align with company priorities? Not everything that's important to you will be important to others.

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:

• It must be globally applicable regardless of market maturity
• It must scale for multi-product offerings
• It must work across multiple countries with their own unique products

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:

• Model it first - Work through several problems together with your team, showing your thought process.
• Co-create principles - Develop the framework collaboratively, which builds buy-in and ensures broader perspectives.
• Gradually increase independence - After establishing the principles, ask your team to apply them independently, offering feedback to refine their approach.

"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:

1. Exploration Tier: Marketing-led demand gen with no boots on the ground and no language customization.
2. Partner Tier: Add channel partners and light product-led sales motion, perhaps using international call centers to cover multiple languages.
3. Development Tier: Full human presence with active outbound sales force in market.

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:

• When you need to diversify revenue streams
• When you need to meet customers where they are in their decision-making process
• When market dynamics and competitive positioning create clear opportunities

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:

1. "Whatever you are, be a good one." The fastest way to get the next opportunity is to excel at what you're doing today. Own it all, even the uncomfortable parts of your role.
2. "Your comfort zone was once an unknown frontier." Constant discomfort is the greatest gift you can give yourself. One of Ashley's proudest moments was when a direct report told her, "This past year has been so uncomfortable in the best way."
3. "Don't hold the gray too long." While seeing multiple perspectives is valuable, sometimes indecision hurts more than making the wrong call. If you're naturally curious and hold off on judging too quickly, you might allow situations to persist that negatively
   
   

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