A Lesson on Empathy from Satya Nadella

The moment everything changed

In 2016, the CEO of Microsoft gave me a piece of advice I still can't unhear.

I was sitting on the top floor of Atlanta's Ponce City Market in a room of 25 Techstars founders... and one very calm CEO, Satya Nadella.

I hadn't built anything of my own yet, but I knew I wanted to.

At the time, my role was "GTM associate" for 10 startups from around the world. My job? Get them investor-ready in 90 days.

So I did what any curious operator would do and became a sponge. I sat in on every investor meeting I could. I took notes like my life depended on it. I made cold calls for founders who barely slept. I scoured reddit for any scrap of market intel I could find.

(2016 Reddit was wild btw. Can't wait to tell my grandkids.)

Then, a few weeks before the end of the program, we got the announcement: Satya Nadella was coming in for a casual 30-minute roundtable.

No slides. No PR team. No fanfare.

Just a room full of founders... and me.

What Satya actually said

That's when he dropped this gem:

"Building a business is hardly ever about the tech. It's about what you can do with it. The possibilities are endless. So if you want to chart a path, make empathy your starting point."

That line changed everything for me.

Up until then, I was fixated on what I could build, who my co-founder would be, how I'd raise capital.

Honestly, I just didn't want to be broke.

But I had no clear vision of who I wanted to help or why it even mattered to begin with.

The shift: From "what" to "who"

After that day, my question shifted:

From: "What can I build?"

To: "Who can I help... and how?"

That single question sparked an 8-year journey into sales enablement.

I worked with tech unicorns, scaling startups, and enterprise sales teams. I built training programs, coached thousands of sellers, and ran countless deal reviews.

And along the way, I discovered something most teams were missing.

What sales teams actually need

The problem with traditional sales training

Most sales training focuses on tactical execution:

• How to run discovery
• How to handle objections
• How to negotiate price
• How to close deals faster

These skills matter. But they're not the root problem.

The real gap: Strategic thinking

The best sellers don't just execute tactics. They understand how their buyers make decisions.

They know:

• Which internal stakeholders hold real influence
• What metrics executives actually care about
• Where deals stall (and why)
• How to build consensus across a fragmented buying committee

These sellers think like consultants, not order-takers.

And here's the crazy part: most sales leaders intuitively understand this. They just don't know how to coach it.

Why? Because, unless you're jumping on all of your reps calls AND doing account research, no sales leader has enough context to truly develop strategic thinking in their reps.

So instead they default to coaching what they can easily measure: activity metrics, pipeline coverage, and call performance.

The problem with approach is that enterprise deals aren't won on calls. They're won in the moments between calls, when your champion is selling internally, when procurement is comparing vendors, when the CFO is questioning the ROI.

Building deep empathy for each buyer's worldview takes time and effort that sales leaders can't afford to give.

A new approach

Look, I know 'empathy' has become a buzzword. Every sales guru on LinkedIn tells you to 'lead with empathy.' But here's what's different in sales: we finally have the tools to actually do it. Call recordings. Win/loss data. CRM analytics. We can stop guessing what buyers care about and start knowing. That’s why I started Storytechr. I got tired of watching sales leaders know what their teams needed but not having a repeatable way to deliver it.

So I built a methodology around three core principles that most sales programs ignore.

Start with Empathy

Every Storytechr engagement starts the same way. We dig into your call transcripts and CRM data to answer one question:

How do your buyers actually make decisions when you're not in the room?

Here's what we dig for:

• Where your deals actually stall (not where your CRM says they stall)
• What words your best champions use when they're selling you internally
• Which objections kill deals vs. which ones are just buyer theater
• How your top performers navigate buying committees without you even knowing it

This isn't guesswork. It's AI-fueled pattern recognition based on your buyer's actual words.

Lead with Clarity

Once you understand the buyer's decision-making process, your job as a sales leader is to create a process that’s consistent enough for sellers to follow, without being so rigid that it stifles creativity.

Here's the paradox you're dealing with: sellers need consistency without rigidity. Clear expectations without micromanagement. You need to give them guard rails, not handcuffs.

That’s why we focus on frameworks rather than playbooks:

• Strategic narrative development – Teaching sellers to craft deal-specific stories that move buyers forward
• Performance scorecards – Objective metrics that measure strategic thinking quality, not just pipeline activity
• Deal showcase sessions – Live coaching that helps reps learn from each other's wins and losses

The result? Sellers who navigate complexity, build internal champions, and close bigger deals because they know exactly what 'good' looks like.

Drive Accountability

Most sales leaders tell me: "I wish I had more time to coach."

But when I look at their calendar and pipeline, I see something else. Time isn't the issue. Clarity is.

Reps hear feedback like "think more strategically" or "understand the buyer better" and have no idea what to actually improve. Why? Because there's no shared standard for what "strategic" looks like.

That's why we build feedback loops that are quick, consistent, actionable, and clear:

• Scoreable outputs – Focus on what sellers create (POVs, problem statements, business cases), not just what they say
• Defined rubrics – Give managers a 1-5 scale with real examples so feedback is objective, not gut feel
• Fast iteration cycles – Turn "you need to think strategically" into "your problem statement is a 3/5/. Here's what's missing, and how to get it to a 4/5."

The result? Coaching that actually compounds. Sellers improve deal after deal because they know exactly what to fix and how to fix it.

Empathy isn't soft. It's strategic.

Satya was right.

It was never about the tech.

It's about who you're helping, and why it matters.

That's why I didn't build a SaaS platform or another training curriculum.

I built a coaching methodology rooted in buyer empathy, because when you understand how your buyers make decisions, everything else gets easier.

Ready to shift from tactical coaching to strategic enablement?

If you're a sales leader tired of coaching the same objection handling and discovery techniques while your deals still stall in late stages, let's talk.

We'll start where Satya told me to start all those years ago:

With empathy.

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P.S. What's the one piece of advice that's shaped your career? I'd love to hear it—drop me a note.