Case Study
Prioritizing effectively against real-world constraints
Overview
A challenge I’ve seen repeatedly in my career as a design leader is the struggle to balance business needs, user expectations, and real-world constraints. Designers are trained to advocate for the best possible user experience, but in fast-moving product environments, the “best” experience is often constrained by engineering effort, business goals, and time. The key isn’t just knowing how to make trade-offs, it’s knowing which trade-offs to make and how to advocate for decisions that create impact without slowing progress.
One of the most pivotal moments I’ve had coaching a designer through this challenge was during the development of a split payments feature. It was a long-requested addition by the bank that would allow users to divide a shared transaction and send requests to family and friends via Interac e-transfer — a highly complex experience with deep technical dependencies. A designer on my team, a talented and user-focused thinker, was deeply invested in crafting this seamless, flexible, and intuitive interaction model. But as the project evolved, she found herself frustrated: product and engineering were pushing for a simpler version due to scope constraints, while she felt strongly that certain user-friendly elements were being sacrificed.
Her question to me was one I’ve heard many times.
A challenge I’ve seen repeatedly in my career as a design leader is the struggle to balance business needs, user expectations, and real-world constraints. Designers are trained to advocate for the best possible user experience, but in fast-moving product environments, the “best” experience is often constrained by engineering effort, business goals, and time. The key isn’t just knowing how to make trade-offs, it’s knowing which trade-offs to make and how to advocate for decisions that create impact without slowing progress.
One of the most pivotal moments I’ve had coaching a designer through this challenge was during the development of a split payments feature. It was a long-requested addition by the bank that would allow users to divide a shared transaction and send requests to family and friends via Interac e-transfer — a highly complex experience with deep technical dependencies. A designer on my team, a talented and user-focused thinker, was deeply invested in crafting this seamless, flexible, and intuitive interaction model. But as the project evolved, she found herself frustrated: product and engineering were pushing for a simpler version due to scope constraints, while she felt strongly that certain user-friendly elements were being sacrificed.
Her question to me was one I’ve heard many times.
A challenge I’ve seen repeatedly in my career as a design leader is the struggle to balance business needs, user expectations, and real-world constraints. Designers are trained to advocate for the best possible user experience, but in fast-moving product environments, the “best” experience is often constrained by engineering effort, business goals, and time. The key isn’t just knowing how to make trade-offs, it’s knowing which trade-offs to make and how to advocate for decisions that create impact without slowing progress.
One of the most pivotal moments I’ve had coaching a designer through this challenge was during the development of a split payments feature. It was a long-requested addition by the bank that would allow users to divide a shared transaction and send requests to family and friends via Interac e-transfer — a highly complex experience with deep technical dependencies. A designer on my team, a talented and user-focused thinker, was deeply invested in crafting this seamless, flexible, and intuitive interaction model. But as the project evolved, she found herself frustrated: product and engineering were pushing for a simpler version due to scope constraints, while she felt strongly that certain user-friendly elements were being sacrificed.
Her question to me was one I’ve heard many times.
How do I fight for the right design when
business and engineering keep pushing back?
#1: Reframing the Challenge
The first thing I helped her do was step back from the all-or-nothing mindset. Instead of seeing the choice as “ideal vs. compromised,” I encouraged her to think of it as “impactful vs. unnecessary complexity.” The best user experience isn’t always the one with the most features — it’s the one that balances usability, feasibility, and business outcomes.
Together, we mapped out the core problem split payments needed to solve: users needed a clear, reliable way to split a payment without confusion or errors. That was the foundation. Anything beyond that had to be measured against effort and impact.
The first thing I helped her do was step back from the all-or-nothing mindset. Instead of seeing the choice as “ideal vs. compromised,” I encouraged her to think of it as “impactful vs. unnecessary complexity.” The best user experience isn’t always the one with the most features — it’s the one that balances usability, feasibility, and business outcomes.
The first thing I helped her do was step back from the all-or-nothing mindset. Instead of seeing the choice as “ideal vs. compromised,” I encouraged her to think of it as “impactful vs. unnecessary complexity.” The best user experience isn’t always the one with the most features — it’s the one that balances usability, feasibility, and business outcomes.
Together, we mapped out the core problem split payments needed to solve: users needed a clear, reliable way to split a payment without confusion or errors. That was the foundation. Anything beyond that had to be measured against effort and impact.
Together, we mapped out the core problem split payments needed to solve: users needed a clear, reliable way to split a payment without confusion or errors. That was the foundation. Anything beyond that had to be measured against effort and impact.
#2: Prioritization Through a Decision Framework
I introduced her to a simple but effective decision framework:
I introduced her to a simple but effective decision framework:
I introduced her to a simple but effective decision framework:
User Impact
Will this feature meaningfully improve the experience or just be a “nice-to-have”?
Will this feature meaningfully improve the experience or just be a “nice-to-have”?
Will this feature meaningfully improve the experience or just be a “nice-to-have”?
Effort & Complexity
What level of engineering effort and time commitment is required?
What level of engineering effort and time commitment is required?
What level of engineering effort and time commitment is required?
Business Alignment
Does this support key objectives like conversion, retention, or revenue?
Does this support key objectives like conversion, retention, or revenue?
Does this support key objectives like conversion, retention, or revenue?
#3: Think Like Product Strategists
One of the hardest lessons for designers is understanding that the best design isn’t always the most elaborate — it’s the one that moves the business forward while solving real user needs. I coach my designers to think beyond visuals and interactions and start speaking in terms of business goals and product outcomes. Instead of just advocating for the “better” design, I encouraged her to reframe her argument.
Instead of: “Users will be confused without this extra step”
Try: “This change reduces drop-off and increases successful completion of split payments, improving conversion.”
That shift made all the difference. She started working closely with the product manager, using data from user research and heuristic evaluations to support her case. Instead of pushing back emotionally, she started advocating strategically.
One of the hardest lessons for designers is understanding that the best design isn’t always the most elaborate — it’s the one that moves the business forward while solving real user needs. I coach my designers to think beyond visuals and interactions and start speaking in terms of business goals and product outcomes. Instead of just advocating for the “better” design, I encouraged her to reframe her argument.
Instead of: “Users will be confused without this extra step”
Try: “This change reduces drop-off and increases successful completion of split payments, improving conversion.”
That shift made all the difference. She started working closely with the product manager, using data from user research and heuristic evaluations to support her case. Instead of pushing back emotionally, she started advocating strategically.
One of the hardest lessons for designers is understanding that the best design isn’t always the most elaborate — it’s the one that moves the business forward while solving real user needs. I coach my designers to think beyond visuals and interactions and start speaking in terms of business goals and product outcomes. Instead of just advocating for the “better” design, I encouraged her to reframe her argument.
Instead of: “Users will be confused without this extra step”
Try: “This change reduces drop-off and increases successful completion of split payments, improving conversion.”
That shift made all the difference. She started working closely with the product manager, using data from user research and heuristic evaluations to support her case. Instead of pushing back emotionally, she started advocating strategically.
#4: The Art of Strategic Compromise
A major lesson I instill in my designers is knowing which battles are worth fighting. Not every detail is worth delaying a launch, but some are critical to success. I told her you don’t need to win every argument, just the ones that truly impact users and business outcomes.
She realized that while she couldn’t get every design element she originally envisioned, she could focus on the highest-value improvements. In the final iteration, she successfully pushed for:
Enhanced visual hierarchy and clear entry points for the feature, aiming to increase user engagement and make navigation more intuitive.
Streamlined tracking model that simplified the view of request statuses, allowing users to easily distinguish between submitted, completed, and cancelled requests.
An uncomplicated calculator tool offering both custom (allowing users to input specific amounts) and equal split options, providing flexibility in managing shared expenses.
A major lesson I instill in my designers is knowing which battles are worth fighting. Not every detail is worth delaying a launch, but some are critical to success. I told her you don’t need to win every argument, just the ones that truly impact users and business outcomes.
She realized that while she couldn’t get every design element she originally envisioned, she could focus on the highest-value improvements. In the final iteration, she successfully pushed for:
Enhanced visual hierarchy and clear entry points for the feature, aiming to increase user engagement and make navigation more intuitive.
Streamlined tracking model that simplified the view of request statuses, allowing users to easily distinguish between submitted, completed, and cancelled requests.
An uncomplicated calculator tool offering both custom (allowing users to input specific amounts) and equal split options, providing flexibility in managing shared expenses.
A major lesson I instill in my designers is knowing which battles are worth fighting. Not every detail is worth delaying a launch, but some are critical to success. I told her you don’t need to win every argument, just the ones that truly impact users and business outcomes.
She realized that while she couldn’t get every design element she originally envisioned, she could focus on the highest-value improvements. In the final iteration, she successfully pushed for:
Enhanced visual hierarchy and clear entry points for the feature, aiming to increase user engagement and make navigation more intuitive.
Streamlined tracking model that simplified the view of request statuses, allowing users to easily distinguish between submitted, completed, and cancelled requests.
An uncomplicated calculator tool offering both custom (allowing users to input specific amounts) and equal split options, providing flexibility in managing shared expenses.
In the example above, we showcase the evolution of our calculator tool, from an early concept to the latest design, refined through multiple rounds of collaboration with our engineering, accessibility, and design systems teams. Our goal was to strike a balance between providing flexibility in calculations while ensuring clear user guidance and compliance with accessibility standards. Ultimately, we streamlined the design to focus on the core user and business need: enabling both even and uneven bill splitting. Introducing breakdowns by method type and percentages proved to be overly complex, so we simplified the experience by defaulting to an equal split. As users input amounts, the split dynamically adjusts, with a clear tally displayed at the top.
In the example above, we showcase the evolution of our calculator tool, from an early concept to the latest design, refined through multiple rounds of collaboration with our engineering, accessibility, and design systems teams. Our goal was to strike a balance between providing flexibility in calculations while ensuring clear user guidance and compliance with accessibility standards. Ultimately, we streamlined the design to focus on the core user and business need: enabling both even and uneven bill splitting. Introducing breakdowns by method type and percentages proved to be overly complex, so we simplified the experience by defaulting to an equal split. As users input amounts, the split dynamically adjusts, with a clear tally displayed at the top.
In the example above, we showcase the evolution of our calculator tool, from an early concept to the latest design, refined through multiple rounds of collaboration with our engineering, accessibility, and design systems teams. Our goal was to strike a balance between providing flexibility in calculations while ensuring clear user guidance and compliance with accessibility standards. Ultimately, we streamlined the design to focus on the core user and business need: enabling both even and uneven bill splitting. Introducing breakdowns by method type and percentages proved to be overly complex, so we simplified the experience by defaulting to an equal split. As users input amounts, the split dynamically adjusts, with a clear tally displayed at the top.
#5: Making Prioritization a Habit
After the project was parked for pick up by developers in the next quarter, we reviewed the experience in our next 1:1. She reflected:
After the project was parked for pick up by developers in the next quarter, we reviewed the experience in our next 1:1. She reflected:
After the project was parked for pick up by developers in the next quarter, we reviewed the experience in our next 1:1. She reflected:
“I used to see constraints as blockers.
Now I see them as part of the process. It’s not about getting the perfect design… it’s about getting the right one for now and improving over time.”
“I used to see constraints as blockers. Now I see them as part of the process. It’s not about getting the perfect design… it’s about getting the right one for now and improving over time.”
That shift, from feeling like design is about winning battles to understanding that it’s about smart decision-making, is what I aim to cultivate in every designer I lead.
Now, in design critiques, I actively embed prioritization discussions:
What’s the core problem we’re solving?
If we had to cut one feature, what would it be?
What’s the smallest change that can create the biggest impact?
By making this a regular practice, designers don’t just become better at prioritizing their work—they become stronger partners to product, engineering, and the business.
In design leadership, success isn’t just about creating great products — it’s about developing great thinkers who can balance creativity, business needs, and real-world constraints. When designers master this, they don’t just execute — they lead!
That shift, from feeling like design is about winning battles to understanding that it’s about smart decision-making, is what I aim to cultivate in every designer I lead.
Now, in design critiques, I actively embed prioritization discussions:
What’s the core problem we’re solving?
If we had to cut one feature, what would it be?
What’s the smallest change that can create the biggest impact?
By making this a regular practice, designers don’t just become better at prioritizing their work—they become stronger partners to product, engineering, and the business.
In design leadership, success isn’t just about creating great products — it’s about developing great thinkers who can balance creativity, business needs, and real-world constraints. When designers master this, they don’t just execute — they lead!
That shift, from feeling like design is about winning battles to understanding that it’s about smart decision-making, is what I aim to cultivate in every designer I lead.
Now, in design critiques, I actively embed prioritization discussions:
What’s the core problem we’re solving?
If we had to cut one feature, what would it be?
What’s the smallest change that can create the biggest impact?
By making this a regular practice, designers don’t just become better at prioritizing their work—they become stronger partners to product, engineering, and the business.
In design leadership, success isn’t just about creating great products — it’s about developing great thinkers who can balance creativity, business needs, and real-world constraints. When designers master this, they don’t just execute — they lead!