4 guests 5 episodes 1,788 words

The Speed Trap: Why the Fastest Companies Are Not Always Moving Fast

Should leaders optimize for decision speed or decision quality?

Ramp built a competitor to American Express in three months with eight engineers. Amazon writes six-page memos before making major decisions. Both companies are legendary for their execution. Both would tell you they optimize for speed. And yet their methods look nothing alike.

The confusion is that most people conflate speed with velocity. Speed is how fast you are moving. Velocity is how fast you are moving in the right direction. The fastest-moving company in the world is wasting resources if it is running the wrong way. Four product leaders from Ramp, Amazon, LaunchDarkly, and the intersection of Stripe, Twitter, and Google offer frameworks that resolve this tension -- and their advice is more compatible than it first appears.

You are leading a product team. Every decision feels urgent. Competitors are shipping. The market is moving. Should you optimize for speed of decision-making, or invest time in getting the decision right? The answer seems obvious -- go fast -- until you realize that some of the most successful companies in tech built their cultures around slowing down at critical moments. The tension between these approaches is real, and resolving it requires a more nuanced framework than either camp typically offers.

The 4 Positions

1 / 4

Velocity is everything -- speed de-risks decisions by lowering the cost of being wrong

Geoff Charles (VP of Product · Ramp)

Advocates: Geoff Charles (VP of Product, Ramp)

Ramp's entire operating model is built on the idea that speed is not just a value -- it is the value. Velocity permeates hiring, promotion, incentives, and organizational design.

"Velocity is everything at Ramp. It's how we design our product development process. It's how we incentivize teams, it's who we want to hire, it's who we want to promote, and it's everything around how we make decisions and how we organize the organization."
Geoff Charles
▶ 00:07:27

The core logic: when you can ship and iterate extremely fast, the cost of any individual wrong decision drops dramatically. If you can build, ship, test, and iterate in days, you never need to spend weeks analyzing. The decision itself becomes cheap.

"If the cost of that decision is really low, then you're able to essentially simplify a lot of decisions."
Geoff Charles
▶ 00:08:44

Speed also creates a virtuous cycle for talent. The best people want to join companies that ship. Shipping attracts talent. Talent ships faster. The companies that move fastest end up with the best people, which makes them move even faster.

Ramp's track record gives this theory teeth. They built a competitor to Amex in three months with eight engineers. Six months later, they built a competitor to Expensify. They hit $100M ARR with under 50 people in R&D. This is not theory -- it is proof that speed, systematically applied, can compress what most companies think takes years into months. The organizational design reinforces speed: small teams, minimal process, and a culture that treats velocity as a first-class metric alongside quality and impact.

When This Applies

The decision is easily reversible, you have fast iteration cycles, the cost of being wrong is bounded, and learning requires real-world data

Go slow to go fast -- distinguish one-way and two-way door decisions

Bill Carr (Former VP of Digital Media · Amazon)

Advocates: Bill Carr (Former VP of Digital Media, Amazon)

Amazon's framework provides the nuance that the pure speed camp lacks. Not all decisions are created equal. One-way doors (irreversible, high-stakes) deserve deliberation. Two-way doors (reversible, low-stakes) should be made quickly.

"To really go fast, you actually need to go slow first and to be very clear on what you're doing and where you want to go. Most people confuse speed with velocity, and the difference between the two is that velocity has both speed and a vector to it."
Bill Carron Lenny's Podcast (Amazon's philosophy on speed vs velocity)

The problem is not that companies move too slowly. It is that they apply the same deliberation process to every decision. When a two-way door decision requires a six-page memo and three review meetings, that is not rigor -- it is dysfunction. Amazon's six-page memos are reserved for the decisions that warrant them.

The practical implication: most product decisions are two-way doors. Ship it, measure it, reverse it if wrong. The few one-way doors -- major architecture choices, pricing model changes, market entry decisions -- deserve the slowdown.

When This Applies

You are a senior leader making consequential calls, the team has information you lack, or previous rapid decisions in this area have required multiple reversals

Your pace degrades to the speed of your recurring meetings

Claire Vo (CPO · LaunchDarkly)

Advocates: Claire Vo (CPO, LaunchDarkly)

Claire Vo identifies the most common and insidious velocity killer in organizations: the meeting cadence becomes the decision cadence.

"From a pace, it's know what your internal pace is, and essentially don't let it degrade to the pace of your recurring meetings. I often find that pace of organizations degrades to the pace of the recurring meetings."
Claire Vo
▶ 00:23:23

If you have weekly syncs, decisions take a week because people defer to the next meeting. If you have biweekly planning, every decision waits for the next planning cycle. The structural solution is to push decisions between meetings, maintain urgency through asynchronous communication, and never let a recurring meeting become the default decision venue.

This is not about eliminating meetings. It is about recognizing that every meeting creates a gravitational pull that slows the decisions around it. Leaders must actively fight this gravity.

When This Applies

Your team is capable of fast decisions but organizational processes are throttling them, meetings have become decision gates, or the cadence of your planning cycles does not match the cadence of your market

Listen deeply and ask one vital question -- quality of understanding beats speed of decision

Shreyas Doshi (Product Advisor · former PM Leader at Stripe · Twitter · Google)

Advocates: Shreyas Doshi (Product Advisor, former PM Leader at Stripe, Twitter, Google)

Shreyas Doshi offers the deepest contrarian position. Rather than optimizing for decision speed, he argues for optimizing for decision quality through better listening.

"He would just listen a lot more than you would expect, say, the CEO to listen. And then he would just ask one vital question and that's something I've tried to use in my leadership style ever since I saw that."
Shreyas Doshi
▶ 00:19:38

The observation: leaders who rush to decide often make mediocre decisions quickly, then spend weeks fixing the consequences. Leaders who listen deeply and ask the one question that reframes the problem make better decisions that stick. The total time -- from decision to successful outcome -- is often shorter with the listening-first approach because there are fewer reversals and course corrections.

This does not mean being slow. It means redirecting the time you would spend in rapid decision-iteration cycles toward deeper upfront understanding. The leader who asks one vital question in a meeting often resolves in five minutes what a speed-optimized team would have spent three sprints iterating on.

Shreyas's approach is particularly relevant for senior leaders who are making fewer but higher-impact decisions. A VP of Product who rushes through a strategic direction change to "move fast" may create months of downstream confusion. The same VP who listens for thirty minutes and asks the one question that clarifies the real constraint saves everyone time. Speed of execution and speed of decision-making are different things, and conflating them is one of the most common mistakes in product organizations.

When This Applies

The decision is irreversible or expensive to reverse, it affects architecture or strategy, multiple teams depend on the outcome, or getting it wrong has compounding consequences

Evidence from the Archive

Ramp

Reaching $100M ARR with under 50 total people in R&D

Ramp building a competitor to American Express in three months with eight engineers

Geoff Charles · VP of Product ▶ 00:07:27

Amazon (Working Backwards LLC)

Amazon's transition from project-based to program-based orientation with single-threaded leaders

The PRFAQ process at Amazon where many great ideas were intentionally not shipped in favor of better ones

Bill Carr · Former VP of Digital Media ▶ Watch

LaunchDarkly

LaunchDarkly where Vo was hired to remind a later-stage company they could operate like a startup

Confronting two leaders who could not work together with direct, immediate feedback rather than waiting for a formal performance cycle

Claire Vo · CPO ▶ 00:23:23

Former PM Leader at Stripe, Twitter, Google

Stripe's small-team culture combining high energy, sound judgment, and low ego to produce magic

Jack Dorsey at Twitter listening through an acquisition discussion and asking 'how does this make our users love Twitter more?'--reframing the entire debate

Shreyas Doshi · Product Advisor ▶ 00:19:38

The Synthesis

The speed vs. deliberation framing is wrong. The real axis is not fast vs. slow -- it is cheap-to-reverse vs. expensive-to-reverse.

Reversibility Axis

Why is the speed-vs-deliberation framing wrong?

Classification Problem

What is the highest-leverage intervention in decision-making?

Structural Bottleneck

What hidden factor throttles even leaders who classify decisions well?

The real axis is not fast vs. slow -- it is cheap-to-reverse vs. expensive-to-reverse. When a decision is cheap to reverse, speed is always right. When expensive to reverse (architecture, pricing, team structure), deliberation is always right. The meta-skill is classification.

Most product teams do not have a speed problem or a deliberation problem. They have a classification problem. They apply the same process to every decision because they have not developed the muscle to distinguish between decisions needing rigor and decisions needing a Slack message.

Even leaders who correctly classify decisions get throttled by organizational structure. If you know a decision is a two-way door but your next planning meeting is two weeks away, the structure defeats the judgment. Fixing structural bottlenecks -- pushing decisions between meetings, enabling async decision-making -- is often more impactful.

Which Approach Fits You?

Answer 3 questions about your situation. We'll match you to the right approach.

Question 1

Is this decision easily reversible?

Question 2

What is slowing you down?

Question 3

Who has the most relevant information?

Notable Absences

The Bottom Line

The final practical insight: most product teams do not have a speed problem or a deliberation problem. They have a classification problem. They apply the same process to every decision because the organization has not developed the muscle to distinguish between decisions that need rigor and decisions that need a Slack message. The highest-leverage intervention is often not changing how you make decisions but changing how you categorize them.

Lenny's Core 4 framework provides the measurement layer for this synthesis. The four dimensions -- Speed, Effectiveness, Quality, and Impact -- show that velocity is not just about moving fast. Teams that are fast but ineffective (building the wrong things) or fast but low-quality (shipping bugs) actually slow down overall because of rework and misdirection. True velocity requires all four dimensions in balance. This is why both Ramp's speed-first approach and Amazon's deliberation-first approach produce excellent outcomes: both achieve alignment between speed and direction, just through different mechanisms.

Sources

Geoff Charles — "Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product)" — Lenny's Podcast, August 6, 2023
Bill Carr — "Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards)" — Lenny's Podcast, November 2, 2023
Claire Vo — "Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD)" — Lenny's Podcast, April 7, 2024
Shreyas Doshi — "4 questions Shreyas Doshi wishes he’d asked himself sooner | Former PM leader at Stripe, Twitter, Google" — Lenny's Podcast, October 31, 2024