The 80% Rule: What Microsoft Taught Me About Customer Time

Someone told me early on at Microsoft: "If you're not spending 80% of your day talking to customers, you're not a product manager."

That landed hard.

Because as a teacher, I'd spent 100% of my day with my users. They were right there in front of me. Thirty of them, every period, telling me exactly what they thought of my lessons whether I asked or not.

The idea that product managers might build things without constantly talking to the people who'd use them seemed absurd.

But that's exactly what happens in most companies.

The Problem With Imaginary Users

Most product teams build for imaginary users.

They create personas with stock photos and made-up names. "Meet Sarah, she's a 34-year-old marketing manager who values efficiency." They make assumptions about what people want based on what they themselves would want. They sit in offices and guess.

Engineers build what they think is needed. Executives approve what they think will sell. And somewhere along the way, the actual user gets forgotten.

Teachers can't do that. Your users are real and present and will tell you immediately when you've got it wrong. A Year 10 will put their head on the desk and go to sleep if you're boring. A Year 8 will tell you to your face that this is stupid. You learn to listen because you have no choice.

That skill transfers directly to customer conversations. You're not there to pitch. You're not there to convince. You're there to understand.

What 80% Actually Means

The 80% rule isn't just about time allocation. It's about orientation. It's about who you're building for and whether you actually know them.

At this stage, if you're building something new, 80% of your time should be conversations. Not surveys. Not assumptions. Not market research reports written by someone who's never met a customer. Real conversations with real people who might have the problem you're solving.

Most people skip this step. They have an idea, they get excited, they start building. Then they discover nobody wants what they built. Or worse, people want something slightly different and now they have to throw away months of work.

Teachers know better. You don't walk into a classroom assuming you know what students need. You assess. You ask questions. You watch faces. You adjust based on what you learn.

Do the same thing with customers.

The Conversation Framework

Here's what I learnt about customer conversations, first at Instructure implementing Canvas across Asia Pacific, then at Microsoft building Teams for Education.

The framework is simple. You've been doing it your whole teaching career.

Assess: Where are they now?

What's their current situation? What tools are they using? What does their day look like? Don't assume. Ask.

This is the same as checking prior knowledge before a lesson. You can't build from where you think they are. You have to build from where they actually are.

Listen: What's frustrating them?

Let them talk. Don't interrupt. Don't jump to solutions. Just listen.

Pay attention to what they're not saying, too. The hesitation before they answer. The topic they keep circling back to. The concern they mention once and then drop.

Teachers are trained to notice these signals. A student who keeps looking at the clock. A student who raises their hand then puts it down. A student who's suddenly quiet when they're usually engaged. You read these cues constantly. Do the same with customers.

Identify the gap: What's the distance?

Where are they now versus where they want to be? What's standing in the way? What have they tried that didn't work?

This is the learning gap. The space between current state and desired state. Your entire teaching career has been about identifying this gap and designing ways to close it.

Explore: What have they tried?

How have they attempted to solve this problem before? What worked? What didn't? Why did they give up on previous solutions?

This tells you what you're competing against. Not just other products, but also the status quo. The way they've always done it. The workaround they've cobbled together. Often the biggest competitor isn't another company. It's inertia.

Check understanding: "So if I'm hearing you right..."

Summarise what they've told you. Give them a chance to correct you. Make sure you've actually understood before you move on.

You do this instinctively when teaching. "So what you're saying is..." or "Let me make sure I understand..." It's the same skill.

Close: "If something existed that solved this, would you want to know?"

Don't pitch. Just ask. If the answer is yes, you've got permission to continue the conversation. If the answer is hesitant, you've learnt something important about how serious this problem actually is.

What You're Listening For

During these conversations, you're gathering specific information:

Pain: How bad is this problem? Is it a mild annoyance or a genuine source of frustration? Do they complain about it unprompted, or do you have to dig to find it?

Frequency: How often does it happen? Daily problems are worth solving. Annual problems probably aren't.

Current solutions: What are they doing now? What's the competition? This includes other products, manual workarounds, and doing nothing at all.

Willingness to pay: Would they actually spend money to solve this? This is the question most people are afraid to ask. Ask it anyway. A problem people won't pay to solve isn't a business opportunity.

The goal isn't to pitch. The goal is to learn.

Implementation Is Teaching

At Instructure, we never did anything for customers without showing them exactly how to do it themselves.

Even when we wrote code, like integrations between Canvas and their student management system, we'd hand it over and walk them through how it worked. We didn't want them dependent on us. We wanted them capable.

This wasn't always popular. Some customers wanted us to just do it for them. They were busy. They were stressed. They didn't want to learn another system. Just make it work and get out of the way.

But we knew that approach would fail. If they didn't understand their own system, they'd be helpless when something went wrong. They'd call us for every little problem. They'd never feel ownership. They'd never get the full value of what they'd bought.

So we taught. Constantly. Relentlessly.

We ran workshops face to face before Covid, online during it. Webinars, training sessions, one-on-one calls, documentation, videos, whatever it took to get people comfortable. Some customers needed more hand-holding than others. Some picked things up instantly. We adapted, just like you adapt to different students in a classroom.

The approach was always the same: meet them where they are, not where you wish they were. Find out what they already know. Build on that. Don't assume they understand your jargon. Don't condescend when they ask basic questions. Don't dump information and walk away.

Sound familiar? It should. That's teaching. That's literally the job.

The Hostile IT Team

I remember one implementation where the IT team was hostile from day one.

They hadn't wanted Canvas. They'd been overruled by the academic leadership. They saw us as invaders, as more work, as a threat to their existing systems.

The temptation was to work around them. Go directly to the academics who actually wanted this. Let the IT team be grumpy in the corner whilst we got things done.

But that would have been a disaster. You can't successfully implement technology in an organisation if the IT team is actively working against you. They'd find ways to slow things down, to create problems, to poison the well with end users.

So I taught them. Not the system, initially. I taught them why we were there. What the academics were trying to achieve. How Canvas could actually make their lives easier rather than harder. I listened to their concerns, which were legitimate. I addressed them seriously. I showed respect for their expertise and their existing systems.

By the end of the implementation, they were some of our strongest advocates. Not because I'd manipulated them. Because I'd treated them like intelligent people who deserved to understand what was happening and why.

That's teaching. That's also change management. It's the same skill.

Relationships Sell More Than Pitches

The customers who succeeded weren't the ones with the most resources or the fanciest technology. They were the ones who engaged with the process. Who asked questions. Who tried things and reported back what worked. Who treated implementation as a learning journey rather than a box to tick.

The customers who struggled were usually the ones who wanted us to do it for them. Who didn't want to learn, just wanted results. And that never works, in implementation or in education. You can't learn for someone else. You can only create the conditions for them to learn themselves.

Here's the thing about selling that nobody tells you: relationships sell more than pitches ever will.

A customer who trusts you, who believes you understand their problems, who's seen you deliver when things got hard, that customer will find budget. They'll fight internal battles to keep working with you. They'll recommend you to others without being asked.

At Instructure, something strange started happening at conferences. Customers would see me across the room and come over. Not to complain. Not to ask for things. To hug me.

I'd helped them through difficult implementations. I'd been in their corner when things went wrong. I'd answered late-night emails. I'd talked them off ledges when their leadership was panicking about go-live deadlines. I'd listened to their problems and found solutions when they thought there weren't any.

And they remembered.

It felt like being a nerdy rock star. Which sounds ridiculous, but that's exactly what it was. I wasn't famous. I wasn't important in any traditional sense. But to these specific people, in this specific world, I'd made a difference. They wanted to tell me about it.

Some of those same customers followed me to Microsoft. When I changed companies, they reached out. When they changed companies, they reached out. To this day, when we meet, it's like old friends. We'd been through things together.

That's not something you can manufacture with marketing. It's not something you can buy with discounts or incentives. It's something you earn by showing up, consistently, as a human being who genuinely cares whether they succeed.

Teachers Already Know This

The best relationships with students aren't built on grades and discipline and formal authority. They're built on care, on showing up, on proving over time that you actually give a damn.

The student who trusts you will work harder for you, forgive your mistakes more readily, and remember you long after they've forgotten the content you taught.

Customers are the same. Exactly the same.

You've spent years learning how to build these relationships. How to earn trust. How to show up for people who are struggling. How to be patient when progress is slow. How to celebrate wins and learn from failures together.

That's the 80% rule in action. Not just talking to customers, but actually caring about them. Not just gathering requirements, but building relationships. Not just closing deals, but creating advocates who'll be with you for years.

Your Homework

This week, have five real conversations with people who might have the problem you're thinking about solving.

Not friends who'll be nice. People who'll be honest.

Use the framework:

1. Assess where they are
2. Listen to what's frustrating them
3. Identify the gap
4. Explore what they've tried
5. Check your understanding
6. Ask if they'd want to know about a solution

Don't pitch. Don't sell. Just learn.

Take notes. Look for patterns. Pay attention to the exact words they use to describe their problems. Those words will become your marketing language later.

And remember: you've been doing this your whole career. Every parent-teacher interview. Every conversation with a struggling student. Every time you helped a colleague figure out what wasn't working in their classroom.

The 80% rule isn't new to you. You just haven't applied it to customers yet.

Now you can.

The 80% rule is one of the frameworks in "Teach Yourself Out," which shows teachers how to translate classroom skills into products, income, and options. If you want the full path, the book goes deeper.