Leading with Powerful Questions Series: Part 3 - Leading With Why?

Essential for Scaling Startups and Building Great Teams

Jim Cook

Feb 18, 2025

In Part 1 and 2 of this series, we discussed:

Part 1 - Leading with Powerful Questions

Part 2 - Start a Listening Tour

In Part 3 of this Series, I want to expand on Leading With Why?

Why is “Leading With Why” Essential for Scaling Startups and Building Great Teams?

Most startup founders and executives I coach are brilliant at explaining what they do. Many also easily articulate how they do it. But the very best, the ones who successfully scale their companies from scrappy early-stage teams to high-growth and extremely valuable organizations……they excel at “Leading with Why”.

Leading with why isn’t just about crafting a compelling mission statement. It’s about consistently reinforcing the deeper purpose behind every strategy, goal, and decision. It’s what transforms good teams into great ones, aligns execution with vision, and sustains momentum in the face of uncertainty….helping your teams run through the proverbial brick walls.

Here’s why “Leading with Why” is such a powerful force when scaling a startup.

The Science of Motivation: Why Drives People More Than What or How

People don’t get up in the morning excited to hit a quarterly revenue target….well, sales people do but they’re a different breed. People get up and kick ass everyday because they believe in something. Believing in something requires connecting people emotionally.

Bottom line: People will be attracted to your company, your team, and you when they believe you. Getting them to believe you requires tapping into their emotions of greed, fear, changing the world, _____ (your emotional connection goes here).

This isn’t just feel-good leadership speak; it’s rooted in neuroscience. I personally believe in neuroscience and bring it into the equation whenever possible…and have already posted about it several times. Neuroscience is “How” our brains make the connections between our senses, our belief systems, and our actions.

When you focus solely on what and how, you engage the neocortex, which handles logic and analysis but doesn’t drive passion or loyalty.

When you lead with why, you activate the limbic brain - the part responsible for emotions, decision-making, and long-term commitment.

Intuit’s “Why”?

“We need to be faster and easier than a pencil” (Scott Cook; Intuit; 1991; All Company meeting when asked about competition).

Scott’s speech continued: “Our customers can currently write a check with a pen and record it with a pencil in their checkbook register faster than we do it with Quicken.”

“All our other competition is focused on double entry accounting style of writing checks, recording them, and reconciling bank statements. All we need to be is faster and easier than this and we will win.”

Netflix’s “Why”?

When we started Netflix with DVD Rentals by mail in 1997, our “Why” was simple. We believed there was a faster, easier, and more convenient way for people to rent movies.

“We need to be more convenient than Blockbuster to rent a movie” (Marc Randolph, Netflix; 1997; one of our first meetings; there were a total of 6 of us!).

“We need to have the biggest selection of DVD movies; The movies always need to be in stock.”

“We will never charge late fees. No More Late Fees!”

“If we do these 3 simple things, we’ll be larger than the largest Blockbuster store within 12 months:”

Always have the movie our customers want. - Selection
Always make sure they have a movie ready to play without having to drive back and forth to a Blockbuster store. - Convenience
No More Late Fees! - Price

Fun fact: There were 9,000 Blockbuster stores at the time and annual revenues for the publicly traded Blockbuster were $6 billion. The largest Blockbuster store revenue was roughly $3M annually. Yes, we surpassed our first 12-month goal!

Fun fact #2: Yes, that was one of our very first envelopes (pictured below) — before they were red — which few have ever seen! This was a convenient way to ship and return the DVD from one envelope without having to leave your driveway — just put it back in your mailbox!

Mozilla’s “Why”?

“We exist to take back the web and make sure the internet stays open and free for all.”

Mozilla’s why was always about its open source DNA to keep the web open and accessible for all and fight to keep the web from being locked away behind walled gardens.

But the initial “Why” when Firefox was launched in the 2004-2005 era was also super simple and focused on just 3 things:

Faster - “Are We Fast Yet?!”
Easier - Tabbed Browsing; Search Bar, “Awesome Bar”, Add-Ons
1. First to introduce Tabbed Browsing vs opening a new Microsoft Window for every URL.
2. First to embed the Search Bar into the Menu Bar allowing for faster, easier searching.
3. First to introduce Add-Ons to make the core of Firefox run better - the precursor to Mobile’s now ubiquitous App Stores.
4. First to introduce the “Firefox Awesome Bar” - a prediction engine in the location bar based on your past locations.
Private / More Secure - The browser was a truly independent piece of software that wasn’t bundled into the core of the operating system - making it remarkably faster and way more private and secure.

The video below: 13 years ago (2012) - “Must Press Play”; One of the best “Why’s” I’ve ever been involved with. The people I worked with here were world-class and the shared purpose was off the charts.

Scaling Requires Alignment, and Alignment Requires Purpose

As a startup scales from a small, tight-knit team to hundreds or thousands of employees, one of the biggest challenges is alignment. In the early days, everyone sits in the same room, decisions happen quickly, and informal communication fills in the gaps. But as the company grows, people naturally begin to focus on their own functions. Marketing cares about campaigns; Sales cares about quotas; Product cares about features; Engineering wonders why Product-Sales-Marketing aren’t aligned!

This functional fragmentation leads to misalignment, inefficiencies, and a culture where people optimize for their own departments rather than the company’s mission…..or better said, the company’s purpose…or wait for it….the company’s “Why”!

Amazon’s “Why”: Customer Obsession as a North Star

Jeff Bezos made “Why” the driving force behind Amazon’s growth: to be the world’s most customer-centric company. This singular purpose aligned every team’s effort from the warehouse to engineering to innovations like AWS. Jeff continuously anchored this customer focus using “Why Frameworks” such as High Quality, High Velocity decisions (see my Decision Making Series). If the new project showed great customer promise, more money was invested in that project. If it didn’t resonate or get adopted by customers, the project was killed. That simple.

Startups that fail to anchor their teams in “Why” often find themselves struggling with silos, miscommunication, and wasted effort as they scale.

“Leading With Why” Fuels Resilience in the Face of Adversity

Scaling a startup isn’t a straight line….it’s a rollercoaster. There will be moments of crushing setbacks, market downturns, lost deals, and internal crises. Teams that are only motivated by short-term targets tend to burn out or jump ship when things get tough. But teams that deeply believe in why they’re doing the work? They push through.

SpaceX’s “Why”: Making the Impossible Possible; “Make Humanity a Multi-Planetary Species”

Elon Musk’s why for SpaceX isn’t just about launching rockets. It’s about making humanity a multiplanetary species. That vision is what kept his team going through early failures, explosions, missed milestones, and near bankruptcy. It’s why top engineers took pay cuts to join. It’s why, when things got hard, they didn’t just give up.

Startups need that same level of resilience. If your team understands why their work matters, they’ll persist even when the odds are against them.

“Leading With Why” Enables Decision-Making at Scale

In a 10-person startup, the CEO can personally approve every major decision. At 500 employees, that’s impossible. Leaders who fail to embed “Why” into their organization end up creating bottlenecks, as employees constantly need approval and reassurance before acting.

But when teams are deeply aligned around “Why”, they can make higher-quality and higher-velocity decisions because they fully believe in the ultimate purpose of the company.

Shopify’s “Why”: Empowering Entrepreneurs; “Make Commerce Better For Everyone”

Tobi Lütke didn’t scale Shopify by micromanaging every product decision. He scaled it by making sure every employee understood the company’s “Why”…..to make commerce better for everyone.

Product teams shipped features without waiting for CEO approval. Customer support reps made judgment calls without rigid scripts. Shopify scaled rapidly by staying focused on their shared “Why”.

If you’re constantly being pulled into low-level decisions, it might be because your team understands what they’re doing, but not why it matters or when they really need you and when they should be taking ownership.

Bringing “Why” Into Your Leadership Playbook

Understanding the importance of why is one thing. Making it part of your leadership DNA is another. Here are 3 ways to put it into practice:

1. Communicate “Why” Relentlessly…”7 Times, 7 Different Ways”

Repetition isn’t redundant, it’s reinforcement. Founders and executives should tie every strategic decision, all-hands meeting, and product update back to why. If your team can’t instantly articulate your company’s purpose, you haven’t said it enough.

2. Tie the Individual and Departmental “Why’s” to the Bigger Company “Why’s”.

Every function should be able to see how their work connects to why. Engineers aren’t just writing code…..they’re building a platform that empowers customers. Sales reps aren’t just closing deals….they’re solving a real problem for real people.

3. Hire and Fire Based on “Why” Alignment

A bad hire with incredible skills can do more damage than a great hire with gaps to fill. Prioritize candidates who deeply resonate with your “Why”. Skills can be taught…..alignment to purpose and emotionally believing in the company and team can’t and is ultimately poisonous.

“Why Are We Doing This?”

One of the simplest and most powerful leadership questions is to relentlessly ask why are we doing this? Or “Why are we doing it this way?”. Make sure not to pose your powerful leadership question in a critical way, but rather in a way that asks for clarity and innovation.

Situations Where Asking “Why?” Changes the Game:

When Priorities Get Blurry
- “Why is this initiative more important than the others?”
- “Does this move the needle on our biggest goal?”
When Teams Feel Disconnected
- “Why does this work matter to our customers?”
- “How does this contribute to our long-term success?”
When Strategy Shifts
- “Why are we pivoting in this direction?”
- “What problem are we solving, and why now?”

These questions force teams to cut through the noise and focus on what truly matters.

Why Most Leaders Fail at Leading With “Why” (and How to Fix It)

Most leaders think they’re communicating their purpose, their vision, their “Why” but are surprised when the employees in the company don’t know it or understand it.

Common Leadership Mistakes:

Assuming Everyone Knows the “Why”
- Fix: Repeat it constantly. If you feel like a broken record, you’re probably doing it right.
Focusing Too Much on the “What” and “How”
- Fix: Start every major conversation by reinforcing why something matters.
Letting Urgency Crowd Out Purpose
- Fix: In fast-moving environments, take a breath and ask, “Why are we doing this?” before diving into execution.

Startups That Scale With “Why” Win

Every successful startup I’ve ever seen or been a part of, including Intuit, Netflix, and Mozilla, has anchored itself in why from the beginning. It creates alignment. It creates teams. It creates culture. It fuels resilience. It enables autonomy. And the company connects with them emotionally……turning what was otherwise just another job into something deeply meaningful.

As a leader, your job isn’t just to set strategies and goals and hold people accountable. Your job is to remind people every day, in every decision, why their work (our work) matters.

Great leaders don’t just tell people what to do. They remind them why it matters. They make the connection between vision, strategy, and execution so clear that their teams stay motivated, even in the face of huge hurdles and crisis events.

Because when people believe in “why”, they’ll find a way to make it happen.

Final Takeaways: How to Lead With “Why” Every Day

Never assume people remember the “Why”—repeat it constantly.
Use “Why are we doing this?” as a filter for every major decision.
Connect vision to strategy to structure to execution in every conversation.
When priorities feel scattered, anchor back to the “Why”.
Frame decisions not just in numbers, but in purpose and the ultimate “Why”.

Your Challenge:

At your next leadership meeting, instead of jumping into tactics, start by asking:

“Why does this work matter?”
“How does this contribute to the overall company. And why?”
“Why do our customers buy our product?”

Leading with why isn’t just about inspiration, it’s about constantly creating and connecting alignment from purpose to strategy to structure to execution for maximum focus and impact.

And that’s what great leaders do. If you want to ask just one question….it just may be this one:

What’s Your “Why”?

That’s a wrap on this 3-part series of Leading with Powerful Questions.

Here are the links to the other blogs within this series: