The Engineering Leadership Pipeline Is Broken—And We're All Feeling It

General
1

I’m in the middle of scaling our engineering team from 25 to 80+ engineers, and I keep running into the same wall: where are all the engineering leaders?

Not senior engineers. Not staff engineers. I mean people who can lead teams, build culture, make hard decisions, and still understand the technical details. People who can be Directors, VPs, eventually CTOs.

The data backs up what I’m feeling:

  • We’re facing a 4.7 million STEM graduate shortfall by 2030 globally
  • Engineering executive demand is up 18% just this year
  • Yet only 28% of engineering executives were promoted through a dedicated internal technical leadership track

Let that sink in. We know there’s a crisis, we know internal development works (companies with structured leadership programs see 25% higher retention), yet 72% of engineering execs came from outside their companies.

Three Pipeline Failures I’m Witnessing

1. Promoting Too Late

We wait for Staff or Principal engineers to “express interest” in management. By then, they’re 8-12 years into their careers, deeply invested in IC work, and honestly? Many of them have already decided they don’t want to manage.

The best engineering leaders I know started thinking about leadership at L4-L5 (mid-level). They got exposure, coaching, and permission to explore before they were “ready.”

2. Training Wrong

Technical training ≠ leadership training.

I see so many companies send their new managers to a 2-day “management bootcamp” and call it done. Then we wonder why they struggle with performance conversations, team dynamics, and strategic thinking.

Leadership skills need deliberate, continuous development—just like technical skills. But we don’t treat them that way.

3. Hiring Externally By Default

When a Director role opens up, the default answer is “let’s hire externally.”

Why? It’s faster (3 months vs. 2-3 years to develop someone). It feels lower risk. And honestly, we’ve already failed at building the internal pipeline.

Meanwhile, 55% of US engineering firms are now exploring international recruitment for executive roles. We’re not even building domestic capacity anymore—we’re outsourcing the problem.

What’s Actually Working (At Least For Us)

At my EdTech company, we’re trying a few things that seem to be working:

Leadership “shadow track” starting at L4-L5:

  • Not a commitment to management, just exposure
  • Engineers can opt in, shadow directors, attend leadership meetings
  • About 40% decide they want to keep exploring, 60% return to pure IC work—and that’s fine!

Quarterly leadership workshops:

  • Not performance review conversations—actual skill building
  • Topics: Giving feedback, delegation, technical strategy, managing up
  • Led by our engineering leaders, not external consultants

Lateral moves are encouraged:

  • Want to be a good engineering leader? Spend time understanding product, design, data
  • We actively encourage engineers to do 6-month rotations before moving into management
  • Cross-functional understanding makes better leaders

The Uncomfortable Truth

Most companies say they value internal mobility but then:

  • Offer external hires 20-30% higher comp for the same role
  • Promote based on “readiness” (code for “already doing the job”)
  • Treat leadership development as a “nice to have” rather than strategic investment

If we’re serious about the engineering leadership shortage, we need to invest early, train deliberately, and promote internally by default.

My Questions For You

  • Where are your future engineering leaders coming from? Internal or external?
  • If you’re developing leaders internally, what’s working? What’s failing?
  • How do you identify high-potential ICs who don’t self-nominate for leadership?
  • Are we promoting too late, training wrong, or something else entirely?

I don’t have all the answers. But with 18% increased demand and a 4.7M talent shortfall looming, we need to figure this out—together.

2

This hits home, Keisha. The pipeline problem is worse for underrepresented groups—and I say that as someone who lived it.

I’m a first-generation college grad from El Paso. At Intel, no one told me that IC → manager was even a career path. The leadership track was informal—you had to “know” to ask. The people who knew to ask? They had parents who were engineers, managers, directors. They understood the game.

I didn’t.

Your three failures are spot-on, but I’d add a fourth: Access Barriers for First-Gen and Underrepresented Engineers

Even when leadership development programs exist, they’re often invisible to the people who need them most. Or they require “sponsorship” from a senior leader—but if you don’t naturally network with execs (because you don’t share their background, interests, or social circles), you never get nominated.

What I’m Building (That I Wish I Had)

At my financial services company, I’m trying to make the invisible visible:

Explicit leadership track on our internal wiki:

  • Not hidden in manager 1:1s
  • Clear criteria, clear timeline, clear application process
  • Anyone can see it, anyone can opt in

Mentorship pairings (junior engineers with directors):

  • Assigned, not opt-in—because opt-in favors those already comfortable asking
  • Monthly coffee chats, quarterly shadowing
  • Focus: demystifying what directors actually do all day

“What does my manager actually do?” monthly sessions:

  • Open to all ICs, led by our engineering managers
  • Topics: sprint planning decisions, hiring, performance reviews, budget conversations
  • Makes the “hidden curriculum” of management transparent

My Big Question

Luis here—how do you identify high-potential ICs who don’t self-nominate?

This is my biggest challenge. The engineers who raise their hand for leadership opportunities? Often already have the confidence, network, and social capital. The ones who’d be incredible leaders but don’t believe they’re “ready”? They stay quiet.

Keisha, your “shadow track” sounds great, but how do you invite people into it? Do you tap people on the shoulder? Use performance data? Manager nominations?

I’m curious what others are doing here. The 4.7M shortage is bad enough—we can’t afford to miss the leaders who are already in our orgs but invisible to us.

3

Both of you are diagnosing this correctly. The 25% retention ROI from leadership development programs is real—I’ve seen it at my own company.

But here’s the brutal truth: CTOs and VPs know this, and we still don’t prioritize it. Why?

The Real Reasons We Don’t Invest

Short-term pressure wins:

  • Hiring a VP externally takes 3 months
  • Growing one internally takes 2-3 years
  • Quarterly board meetings don’t reward 3-year investments

Misaligned metrics:

  • Leadership development doesn’t show up in sprint velocity
  • It doesn’t show up in revenue
  • It does show up in retention and team effectiveness—but those are lagging indicators

The classic mistake:

  • “What if we train them and they leave?”
  • The real question: “What if we don’t train them and they stay?”

My Contrarian Take: Leadership Isn’t a Binary Switch

Luis, your question about identifying high-potential ICs is great—but I think the premise is flawed.

The industry treats IC → manager as a permanent role change. You’re either an IC or a manager. Pick one.

This creates two problems:

  1. High-potential ICs are afraid to try management (“what if I hate it?”)
  2. Mediocre managers stay in management (“I can’t go back to IC without looking like a failure”)

What if leadership was more fluid?

At my SaaS company, we’re experimenting with “leadership rotations”:

  • 6-month stints leading initiatives (not teams, but cross-functional projects)
  • No title change, but real leadership exposure and coaching
  • Explicit expectation: you can return to IC work—it’s not a demotion

Early results:

  • About 40% continue toward formal management roles
  • 60% return to IC work but with dramatically better cross-functional skills
  • Both groups become better leaders, regardless of title

The Crisis Is Also an Opportunity

That 18% exec demand increase? It’s a crisis for orgs that don’t invest. But it’s an opportunity for orgs that start building internal pipelines now.

Three years from now, you’ll either:

  • Have a bench of internal leaders ready to step up
  • Be competing with 55% of US firms for international exec hires

Start now, or pay later.

4

Michelle, your “leadership rotation” idea is fascinating—and it makes me wonder: Does this work for non-engineering leaders too?

Context: I’m VP Product, and I see product managers plateau because they don’t understand technical constraints. They pitch features that are architecturally impossible, or they don’t grasp why “just add a field to the API” takes 3 sprints.

Meanwhile, I’ve seen engineers struggle in product roles because they don’t understand customer development, prioritization trade-offs, or how to say no to stakeholders.

The Cross-Functional Leadership Gap

The best product leader I ever worked with at Airbnb? Former engineer who did a PM rotation for 18 months. She could:

  • Read technical design docs and spot architectural risks
  • Have credible conversations with engineering about feasibility
  • Translate customer needs into technical requirements

The best engineering manager I know? Did a 6-month product rotation. He now understands why we can’t build every feature and can explain trade-offs to his team in business terms.

My Question for the Group

Has anyone tried cross-functional leadership development tracks?

Not just IC → manager within engineering, but:

  • Engineers → Product (to understand customer problems)
  • Product → Engineering (to understand technical constraints)
  • Design → Engineering (to understand implementation realities)

What worked? What failed spectacularly?

I’m curious if the 4.7M STEM shortage is partly a multi-disciplinary leadership shortage—we’re not just missing engineering leaders, we’re missing leaders who can bridge engineering, product, design, and business.

5

This whole thread resonates, but I’m going to push back a little on the “we need more formal programs” consensus forming here.

Full disclosure: I founded a startup that failed hard. I learned more about leadership from that 18-month disaster than I did from my entire 12-year career before it.

Luis’s point about explicit leadership tracks is great—especially for accessibility. Michelle’s leadership rotations sound smart. Keisha’s shadow tracks make sense.

But…

Are We Over-Indexing on Process?

The best leaders I know didn’t learn through programs. They learned through:

  1. Side projects that failed (like my startup)
  2. Cross-functional work that forced them outside their comfort zone (like David’s examples)
  3. Organic mentorship (not assigned coffee chats—real relationships)

Here’s a micro-example from my design systems work:

A junior designer on my team took initiative to audit accessibility across 3 product teams. No one asked her to. No “program” existed for it. She just… did it.

Within 6 months, she was the de facto accessibility lead. Product and engineering started coming to her for guidance. Now she leads a team of 4.

She learned leadership by doing, not by attending workshops.

My Question (Maybe Uncomfortable)

How do we balance:

  • Structure (Luis’s explicit tracks, Michelle’s rotations) that makes opportunity accessible
  • Organic growth (side projects, initiative, emergent leadership) that often produces the best leaders?

I fully acknowledge: “just take initiative” is a privilege thing. If you’re a first-gen engineer (like Luis), you might not feel safe taking risks. If you’re working 60-hour weeks, you don’t have time for side projects.

So maybe the answer is: Structured programs that create space for organic growth?

And one more thought: The 4.7M shortage might also be an opportunity to rethink what “leadership readiness” even means. Maybe we’re gatekeeping with outdated criteria—“10 years of experience,” “proven track record”—when the best future leaders are the ones willing to learn fast, fail forward, and build things that don’t exist yet.