We scaled headcount without scaling leadership—and now we're paying for it

[alex_architect]

I joined my current EdTech startup as VP of Engineering nine months ago. On paper, everything looked great: growing revenue, recent Series B, engineering team of 35 that needed to scale to 80+.

Week one, I discovered the problem no one had named: we had zero engineering directors.

Seven engineering managers reported directly to me. Each managed teams of 5-8. When I asked about the director role, the previous VP said they “never found the right people externally” and were “waiting for managers to be ready.”

Translation: we scaled headcount without scaling leadership.

The Math Doesn’t Add Up

I started digging into industry data, and here’s what’s keeping me up at night:

• 18% surge in engineering executive demand by 2026 (source)
• Hiring timelines doubling—senior roles now take 40-50 days vs historical 30-35 (source)
• 25% of working engineers plan to retire within 5 years, with 200,000 new engineers needed annually just to keep pace

Meanwhile, here in Atlanta’s tech scene, every growth-stage company is competing for the same tiny pool of proven engineering directors.

The external hiring path isn’t going to save us.

Are We Promoting Too Late or Training Wrong?

I’ve been reflecting on my own path: IC at Google → EM at Google → Senior EM at Google → Director at Slack → VP at current company.

I had years of leadership development. Structured programs. Rotations. Mentorship from VPs who invested in me. Access to executive coaches.

Now I look at my managers—brilliant engineers who are drowning in operational work—and realize we’re asking them to figure out leadership on their own while also scaling their teams.

We promoted them based on technical skills, then expected leadership capability to magically appear.

When I shadowed one of my managers for a week, I watched them spend:

• 40% of their time in 1:1s and team ceremonies
• 30% on cross-team coordination and escalations
• 20% in hiring and interviews
• 10% on their own manager responsibilities (roadmap, strategy, people development)

Zero time learning how to be a director. Because that’s not a thing we do here.

What Would Leadership Pipeline Thinking Actually Look Like?

I’m wrestling with this question right now. Some early ideas:

1. Identify high-potential ICs 18-24 months before promotion
Not “who’s ready now?” but “who has trajectory with coaching?”

2. Create learning opportunities that mirror the next role

• Shadow director/VP meetings
• Own a cross-team initiative
• Attend leadership training (not just send them a book)

3. Be honest about the capacity gap
If I need 3 directors but only have 1 manager “ready,” I can’t wait 2 years. I need to build the pipeline and hire externally.

4. Measure leadership development like we measure delivery
What’s our internal promotion rate to director? How many high-potentials have we lost? What’s our bench strength?

I’ll be honest: I’m still figuring this out.

We just started a “future leaders” cohort—6 engineers (managers and senior ICs) meeting monthly with an external coach. It’s early, but the quality of their questions and self-awareness is already shifting.

The Question That Haunts Me

Every time I see an open director role take 60+ days to fill, or watch a manager burn out, or lose a high-potential IC because they don’t see a path forward…

Are we promoting too late? Or are we training wrong?

Maybe it’s both.

What does leadership development look like at your company? Is it structured, or are we all just hoping people figure it out?

I’d love to hear what’s actually working—or what you’ve tried that failed spectacularly.

[product_david]

This hits close to home, Keisha.

I’ve been thinking about this exact problem from a different angle—one that doesn’t get talked about enough in these conversations.

The First-Gen Leadership Gap

When I became Director of Engineering at my financial services company three years ago, I realized something uncomfortable: I had no mental model for what a director does beyond what I’d observed.

I’m first-gen college. My parents were blue-collar workers in El Paso. Amazing role models for work ethic and resilience, but they had no context for navigating corporate leadership. I couldn’t call my dad and ask “how do you handle a VP who wants different roadmap priorities than your product partner?”

The managers and ICs I mentor through SHPE face the same challenge, but compounded. They’re not just figuring out the technical aspects of leadership—they’re also translating an entire corporate culture and vocabulary that their networks didn’t prepare them for.

Your question “Are we promoting too late or training wrong?” assumes people have equal access to informal leadership development. They don’t.

What Actually Worked: Shadow Board Program

After losing two high-potential engineers (both Latino, both first-gen professionals) to companies that offered them director titles, I stopped waiting for “the right time” and built something intentional.

We created a Shadow Board program:

The concept: 6 high-potential engineers (mix of managers and senior ICs) attend our monthly director-level strategy meetings for 6 months. They don’t present. They observe, take notes, ask questions in a debrief afterward.

What they learn:

• How decisions actually get made (spoiler: not like the textbooks say)
• The vocabulary and frameworks directors use
• What “strategic thinking” looks like in practice vs theory
• How to navigate cross-functional conflicts and stakeholder management

The results after 18 months:

• 3 internal promotions to director (vs 0 in the prior 2 years)
• 2 participants left for director roles at other companies (I count this as success—they were ready)
• 1 decided they wanted to stay IC and pursue the Staff+ track (also success—better to know)

The program costs us basically nothing except meeting time. But the transparency and demystification of the role? Invaluable.

The Question We’re Not Asking

Here’s what keeps me up at night, though:

How do we make leadership development accessible to people who don’t already “look the part”?

When I scan the room at director+ meetings in our industry, I see a lot of the same backgrounds. Similar schools. Similar companies on their resumes. Similar networks.

The informal leadership development you had at Google and Slack, Keisha? That’s systematically unavailable to people who didn’t get those early-career opportunities.

And when companies say they’re “waiting for people to be ready,” what they often mean is “waiting for people who remind us of ourselves.”

Your “future leaders cohort” is exactly the kind of intervention that works. But I’d push one level deeper:

Are we selecting for high-potential based on demonstrated leadership capability, or based on confidence and communication styles that reflect existing power structures?

Because the quieter, more collaborative engineer who thinks deeply before speaking? They might be a better director than the person who sounds confident in every meeting.

Practical Takeaway

If you’re building leadership pipelines, ask yourself:

1. Who gets nominated for high-potential programs? Track the demographics. If it’s skewed, your selection criteria are biased.

2. What does “executive presence” actually mean at your company? Be specific. If it’s code for “talks like the current executives,” you’re replicating the same patterns.

3. How are you creating access for people outside traditional networks? Shadow programs, rotations, and structured mentorship help level the playing field.

I’d love to hear from others: What’s working in your orgs to build diverse leadership pipelines? And what assumptions are we still holding onto that need to be challenged?

[vp_eng_keisha]

Luis, your Shadow Board program is brilliant. I’m stealing that.

But I want to challenge something both of you are dancing around:

The timing paradox isn’t just about when we promote—it’s about how many leadership roles we’re creating.

The Hard Truth I Learned

Two years ago, I lost one of the best architects I’ve ever worked with. Sarah had been with us for 6 years. Staff engineer. Led the migration to our current platform. Everyone came to her for technical decisions.

She told me she was leaving for a Director of Engineering role at a competitor. I was shocked.

“Sarah, you’ve never managed people. You love being hands-on. Why director?”

Her answer: “Because that’s the only path to growth you’ve shown me. I’ve been at the same level for three years. I don’t want to manage, but I do want progression.”

I promoted her too early and burned her out. She quit 11 months later.

Promote too early and you burn people out. Wait too long and they leave.

That’s the paradox Keisha described. But I think we’re solving the wrong problem.

Leadership Capacity Planning (Like Systems Capacity Planning)

Here’s the framework that’s been working for me:

1. Forecast leadership demand 12-24 months out

Just like we do capacity planning for infrastructure:

• How many teams will we have?
• What’s our manager:IC ratio target?
• How many directors can I realistically support as CTO?
• What’s our span of control breaking point?

2. Map current leadership supply

• Who’s ready now (6-12 months)?
• Who’s high-potential (12-24 months)?
• Who opted out of management (Staff+ IC track)?

3. Identify the gap and fill it two ways simultaneously

If I need 3 directors in 18 months but only have 1 high-potential manager:

• Hire 1-2 directors externally (don’t wait)
• Invest heavily in developing the 1 internal candidate
• Create Staff+ IC roles for those who want growth without management

The mistake I made with Sarah was assuming one leadership ladder when we needed multiple.

Maybe It’s Not About Timing—It’s About Options

What if the real problem is that we’ve created exactly one definition of “senior leadership” in engineering orgs?

Here’s what we’ve built at my current company:

Engineering Manager Track:
IC → Manager → Senior Manager → Director → VP → CTO

Technical Leadership Track:
IC → Senior IC → Staff Engineer → Senior Staff → Principal → Distinguished

Rotating Leadership:
6-month rotations for ICs who want leadership exposure without committing to full-time management. They lead initiatives, mentor, represent engineering in cross-functional planning.

Result? Our “leadership pipeline problem” got a lot smaller when we stopped funneling everyone toward the same bottleneck.

The Question That Changed Everything

Luis, you asked: “How do we make leadership development accessible to people who don’t already look the part?”

I’d add: Are we defining “leadership” in a way that only fits one archetype?

The quieter engineer who writes excellent design docs and mentors junior engineers? That’s leadership.

The IC who sees a gap in our observability strategy and rallies three teams to fix it? That’s leadership.

The manager who creates psychological safety and has the lowest attrition on their team? That’s leadership.

But we only promote one of those paths to “director” and wonder why our leadership pipeline is narrow.

What’s Actually Working

Specific tactics that have worked at our 120-person engineering org:

Staff+ IC track with clear expectations and compensation parity

We lost too many technical leaders to management because that was the only way to get comp increases. Now our Principal Engineers make the same as Directors.

Rotation programs for high-potential ICs

Want to try being a manager? Lead a team for 6 months. Hate it? Go back to IC with zero stigma. Two of our best Staff Engineers did this and realized management wasn’t for them—but they became way better technical leaders.

External hiring for 50% of director+ roles

Controversial take: hiring externally isn’t failure. It brings in new perspectives, relieves pressure on your internal pipeline, and gives your high-potentials examples of different leadership styles.

“Leadership capacity” as a budget line item

We allocate 15% of engineering budget to leadership development: coaches, training, conference speaking opportunities, offsites. It’s not discretionary. It’s infrastructure.

Back to Keisha’s Question

Are we promoting too late or training wrong?

I think we’re asking people to compete for too few roles, defined too narrowly, with too little support.

The answer isn’t just better training or faster promotions. It’s creating more pathways to leadership and actually investing in them.

Otherwise we’re just optimizing the timing on a fundamentally broken system.

[alex_infrastructure]

Okay, I’m going to be that guy who asks the uncomfortable question from the product side.

Michelle, Luis, Keisha—everything you’re describing makes total sense for building better engineering leaders.

But here’s what I’m seeing as VP Product:

The best engineering leaders I’ve worked with didn’t just come up through engineering.

The Cross-Functional Blind Spot

Story time: Six months ago, I had an eng director shadowing me for two weeks. His CTO suggested it as “leadership development.” I was skeptical—what’s a product person going to teach an engineer about leading engineers?

Turns out, a lot.

Week 1: Customer Research

I took him to 8 customer interviews. B2B SaaS, so we’re talking CFOs, ops leaders, end users.

After the third interview, he said: “I’ve been here 4 years and I’ve never actually talked to a customer. I’ve read PRDs and sat in product reviews, but I’ve never heard them describe their problems in their own words.”

After the eighth interview: “Holy shit. Half the features we built last year solved problems customers didn’t actually have.”

Week 2: Go-to-Market Strategy

Sales kickoff planning. Pricing discussions. Competitive positioning. Partnership negotiations.

His reaction: “I had no idea how much of product-market fit happens after we ship the code. I thought engineering was building the product. We’re actually building one input into a much bigger system.”

The Revelation

By the end, he completely changed how he approached his roadmap.

Before: “What does the product team want us to build?”

After: “What customer problems are we solving, what’s the business impact, and what’s the least engineering investment to validate that?”

His team’s delivery speed stayed the same, but their impact doubled because they were solving the right problems.

Are We Training Leaders in a Vacuum?

Here’s my challenge to the group:

Most engineering leadership development is engineering-only.

• Technical strategy workshops
• Architecture reviews
• Eng management training
• Coding best practices

All important! But also… incomplete?

The eng leaders who become CTOs vs those who plateau at Director—the difference isn’t technical depth. It’s understanding how engineering creates business value.

And you can’t learn that by only talking to other engineers.

What If Leadership Development Meant Cross-Functional Rotations?

Crazy idea (maybe not that crazy?):

High-potential engineers should spend time embedded in:

Product for 1 month:

• Join customer calls
• Attend sales demos
• Review analytics and user research
• Understand how product decisions actually get made

Sales/CS for 2 weeks:

• Shadow enterprise sales calls
• Sit with customer success on support escalations
• Hear what customers actually say about the product (vs what we think they say)

Finance/Operations for 1 week:

• Unit economics deep dive
• Budget planning process
• See how engineering investments get justified to the board

Go back to engineering with context:

Now when product says “this is a P0,” the eng leader can ask:

• What’s the revenue impact?
• What customer segment needs this?
• How does this affect our competitive position?
• What’s the cost of delay vs cost of building it wrong?

The Uncomfortable Truth

I’ve worked with eng directors who think their job is “build what product tells me to build, on time and with quality.”

Those are Senior Managers.

Directors and above? Your job is understanding the business well enough to challenge the roadmap.

But we’re not training people to do that. We’re training them to be really good at engineering.

Practical Suggestion

Keisha, for your “future leaders cohort”—what if you partnered with other functions?

• Pair each engineer with a PM for monthly customer research
• Have them present engineering strategy to the sales team (not technical details, business impact)
• Make them sit in on a board meeting where the CEO talks about the roadmap

Michelle, your Staff+ IC track is brilliant. But I’d bet your Principal Engineers who understand the business end up having way more impact than those who just go deeper technically.

Luis, your Shadow Board program—does it include cross-functional leaders? Or just eng directors?

The Question I’m Really Asking

What if we’re optimizing for “better engineering leaders” when we actually need “business leaders who came from engineering”?

Because when I look at the CTOs I admire most—they can talk to the CFO about unit economics, the VP Sales about competitive wins, and the board about market dynamics.

And none of them learned that in engineering leadership training.

Are we promoting too late or training wrong?

Maybe we’re training in too narrow a domain.