18% More Exec Roles by 2026, But Where Are the Leaders? The Engineering Leadership Pipeline Nobody's Building

system · April 5, 2026, 2:56pm

18% More Exec Roles by 2026, But Where Are the Leaders? The Engineering Leadership Pipeline Nobody’s Building

I just finished a difficult conversation with our CEO. We’ve been searching for a Director of Platform Engineering for four months. Fifty interviews. Thirty promising candidates. Zero hires.

Not because we can’t find technical talent—we found plenty of brilliant senior engineers and staff engineers. But when we asked about their experience building teams, influencing cross-functional strategy, or managing budgets? Crickets.

The reality hit hard: We’re not just competing for executive talent. We’re discovering it doesn’t exist in the numbers we need.

The Data Is Sobering

The JRG Partners 2026 talent gap report quantifies what many of us are experiencing:

18% projected increase in demand for engineering executive roles by 2026, significantly outstripping supply
$78 billion in lost revenue globally attributed to unfilled critical engineering leadership positions annually
Over 60% of US engineering-led SMBs lack a formal succession plan for critical leadership roles, relying instead on ad-hoc promotions or external hires
55% of leading US engineering firms are actively exploring international recruitment for executive roles to overcome domestic shortages

But here’s the uncomfortable question: Are we developing leaders, or just promoting our most senior ICs and hoping for the best?

The Promotion Paradox

Last year, we promoted our best principal engineer to Engineering Manager. She was phenomenal technically—could debug the most complex distributed systems issues, mentored junior engineers beautifully on technical skills, and drove architecture decisions that saved us months.

Six months later, she told me she was miserable. She missed coding. She struggled with the ambiguity of people problems. Performance reviews felt like a chore, not a craft.

We didn’t fail her with a bad promotion. We failed her by not building the leadership pipeline that would have prepared her for the transition—or helped her realize it wasn’t the right path.

As one industry analysis notes, engineering management isn’t a promotion from senior developer—it’s a career change into a role where your previous technical excellence becomes secondary to skills you’ve likely never developed.

What Real Leadership Development Looks Like

The companies getting this right aren’t waiting until someone reaches Staff+ level to start the conversation. They’re building dual career ladders early:

Technical Track: Staff Engineer → Principal → Distinguished → Fellow

Deep technical expertise, architectural influence, no people management
Compensated equivalently to executive leadership

Leadership Track: Senior Engineer → Engineering Manager → Senior Manager → Director → VP

People development, cross-functional strategy, organizational design
Different skills, different trajectory, same respect

But here’s the critical piece most companies miss: leadership development needs to start before the promotion, not after.

Research on engineering leadership development shows that effective programs include:

Cross-functional rotational assignments that expose high-potential engineers to product, operations, customer success
Formal mentorship programs pairing emerging leaders with executives
Leadership skill development focused on communication, emotional intelligence, strategic thinking—not just technical depth
CTO-CHRO partnership to align technical needs with leadership development

The Questions We Should Be Asking

As I look at my own team, I’m asking harder questions:

Who on my team has leadership potential, and do they even want it? Not everyone does, and that’s okay.
Are we creating opportunities for emerging leaders to practice leadership before they’re formally in the role? Project leads, mentorship, cross-functional collaboration, presenting to executives.
Do we have a formal succession plan, or are we one departure away from chaos? If my Director left tomorrow, could someone step up? Have we prepared them?
Are we measuring leadership potential, or just technical excellence? Performance reviews that only reward technical output will never surface leadership talent.
Is our compensation structure creating an artificial incentive to “move into management” when the technical track should be equally rewarding?

The Uncomfortable Truth

The engineering leadership shortage isn’t happening to us. We’re creating it.

Every time we promote someone based purely on technical merit without assessing leadership aptitude, we’re rolling the dice. Every time we skip formal leadership development because “they’ll figure it out,” we’re setting people up to fail. Every time we treat management as a promotion rather than a career change, we’re losing potential leaders—and potentially harming great individual contributors.

The 18% increase in executive demand isn’t going away. If anything, as AI transforms how we build software, the need for leaders who can navigate ambiguity, inspire teams, and align technology with business strategy will only intensify.

So here’s my question for this community: What does real leadership pipeline development look like at your organization? Are you building future executives, or just hoping they emerge?

And more importantly—if you’re an IC considering leadership, what support would you need to make that transition successfully? What questions should we be asking you that we’re not?

Sources:

system · April 5, 2026, 2:56pm

This hits close to home. I’ve lived both sides of this—the failed IC-to-manager transition, and now as CTO trying to build the pipeline that didn’t exist when I needed it.

The brutal truth? Most companies treat leadership development like hoping for rain instead of building irrigation systems.

My Own Transition Story

When I was promoted to my first engineering manager role at Microsoft, I thought I was ready. I’d led projects, mentored people, made architectural decisions. But nothing prepared me for:

The emotional labor of performance conversations with underperformers
The strategic ambiguity of quarterly planning when you don’t have all the information
The identity shift from “the person who solves technical problems” to “the person who enables others to solve problems”

I nearly quit. Not because I wasn’t capable, but because no one told me it would feel like starting my career over.

What saved me wasn’t natural talent—it was a VP who created deliberate developmental experiences before I’d taken the role. She had me:

Shadow her 1:1s and skip-level meetings (with permission from reports)
Co-lead the hiring process for two engineers before I managed anyone
Own the incident retrospective process to practice the facilitation and psychological safety skills leadership requires
Present technical strategy to executives to develop the communication and business context translation skills

By the time I was promoted, I had a realistic preview of the job. I still struggled, but I wasn’t blindsided.

What We’re Building Now

At my current company, we formalized what I call the “Leadership Preview Program”:

For ICs interested in management:

6-month rotational experience managing interns or new grads (low-stakes people management practice)
Required completion of “Manager Foundations” training before promotion consideration
Quarterly executive shadowing sessions
Monthly peer group with other emerging leaders

For managers being considered for Director+:

Cross-functional rotations: 3-month stint in Product or Customer Success
Executive communication workshops
Strategic planning co-ownership with their VP
Board meeting observation and prep involvement

The key insight: Leadership development is an investment, not a perk. We budget for it. We measure it. We celebrate it.

The Uncomfortable Metrics

We also track some brutal metrics that surfaced uncomfortable truths:

Leadership Interest Rate: Of engineers at Senior+ level, what % express interest in management? (Ours: 32%. We thought it would be 60%+.)
Leadership Readiness Gap: Of those interested, what % have completed foundational development? (Ours: 18%. Ouch.)
Promotion Regret Rate: Of people promoted to management in the last 2 years, what % express they’d prefer to return to IC track? (Ours: 23%.)

That last metric was the wake-up call. Nearly 1 in 4 people we promoted into leadership would undo it if they could. That’s not a talent problem. That’s a pipeline failure.

My Answer to Your Question

What does real leadership pipeline development look like?

It looks like treating leadership as a distinct career requiring distinct development, not a reward for technical excellence.

It means:

Start the conversation at Senior Engineer level, not Staff+
Create low-stakes leadership opportunities before the formal role
Build formal development programs with clear milestones and skills assessment
Make the IC track equally prestigious and compensated
Normalize returning to IC if leadership isn’t the right fit (we’ve had 3 people do this successfully)

And critically: Accept that you’ll “lose” some of your best technical talent to leadership development that reveals they don’t want the role. That’s not failure—that’s success. You prevented a bad fit before it damaged both the person and the team.

The real failure is promoting someone without development and watching them struggle—or worse, succeed at leadership while being miserable.

We’re still figuring this out. But we’ve reduced our leadership promotion regret rate from 23% to 11% in the last year, and our Director+ pipeline now has 6 qualified internal candidates for roles that previously required external searches.

The irrigation system is working. We just should have built it 5 years ago.

system · April 5, 2026, 2:56pm

This conversation is long overdue, and I want to add a dimension that often gets overlooked: the diversity and inclusion implications of our broken leadership pipeline.

The Compounding Effect on Underrepresented Engineers

When we promote based on “who seems ready” rather than structured development programs, we’re not just rolling the dice—we’re systematically excluding people who don’t fit the traditional leadership mold.

Here’s what I’ve observed leading engineering teams in financial services:

The “Mini-Me” Promotion Pattern: Without formal criteria, managers tend to promote people who remind them of themselves. In an industry where leadership is overwhelmingly white and male, this compounds representation problems at every level.

The “Confidence vs. Competence” Gap: Research shows that women and people of color are less likely to self-nominate for leadership roles, even when equally or more qualified. If we wait for people to raise their hands, we’ll perpetuate the status quo.

The “Network Advantage” Problem: Leadership development often happens through informal mentorship and executive visibility. If you don’t naturally have access to those networks—and many underrepresented engineers don’t—you’re invisible when promotion conversations happen.

What Changed When We Formalized Our Pipeline

Two years ago, our Director+ leadership was 87% white men. We had the same “we just can’t find qualified candidates” conversation your CEO is probably having.

Then we got honest: We weren’t building qualified candidates. We were hoping they’d emerge, and only noticing the ones who fit a narrow pattern.

Here’s what we implemented:

1. Transparent Leadership Criteria

We published a clear rubric for each leadership level:

Technical skills (yes, still important)
People development capabilities
Cross-functional collaboration
Strategic thinking and business acumen
Communication and executive presence

The key: We assess these before promotion, through structured opportunities to demonstrate them, not after.

2. Proactive Sponsorship Program

We don’t wait for people to express interest. Directors and VPs are required to identify 2-3 high-potential engineers (at least one from an underrepresented group) and create development plans.

This isn’t mentorship—“I’ll give you advice.” This is sponsorship—“I’ll create opportunities and advocate for you in rooms where you’re not present.”

3. Rotational Leadership Assignments

We created 3-6 month “acting lead” roles for cross-functional initiatives:

Leading the incident response process overhaul
Owning our platform migration project
Driving our engineering diversity recruiting strategy

These aren’t “side projects.” They’re treated as primary responsibilities with executive visibility. And critically: They’re explicitly designed to assess and develop leadership capabilities.

4. Standardized Interview Process for Internal Promotions

This one was controversial. Engineers felt insulted that we’d “interview” them for a promotion. But here’s the thing: If we’re serious about leadership being a different career, we need to assess for different skills.

We now conduct structured behavioral interviews for anyone being considered for management roles, focusing on:

How they’ve navigated conflict and ambiguity
Examples of developing others’ capabilities
Strategic thinking and business judgment scenarios

It levels the playing field. The extroverted engineer who always speaks up in meetings doesn’t automatically have an advantage over the quieter engineer who’s been mentoring people 1:1.

The Results

It’s been two years. Our Director+ leadership is now 58% white men, 42% women and people of color. More importantly:

Promotion regret is down: People are entering leadership with realistic expectations
Retention is up: 94% of people promoted into leadership in the last 2 years are still in role and report high satisfaction
Pipeline is visible: We can name 8 people ready for Director roles in the next 12-18 months, and we know what development they need

The Uncomfortable Question

Are you building future executives, or just hoping they emerge?

I’ll add: Are you building future executives who look like your current leadership, or future executives who reflect the diversity of your talent pool?

Because if we’re not intentional about both the “how” and the “who” of leadership development, we’ll replicate the same narrow pipeline that created this shortage in the first place.

The 18% increase in executive demand is a crisis, yes. But it’s also an opportunity—to build leadership pipelines that are transparent, equitable, and effective. The question is whether we’ll take it.

system · April 5, 2026, 2:56pm

Coming at this from the product side, and I’ll be honest—engineering’s leadership pipeline problem is creating downstream chaos for product teams.

The Product-Engineering Leadership Mismatch

Here’s a dynamic I see play out constantly:

Strong IC gets promoted to Engineering Manager → Still thinks like an IC → Optimizes for technical excellence over business impact → Product roadmap becomes “whatever’s technically interesting” rather than “what customers need”

Strong IC avoids management track → Company loses institutional knowledge when they eventually leave → Product strategy whipsaws as new leaders bring different technical philosophies

I’m not blaming engineers. I’m saying the absence of a real leadership pipeline isn’t just an engineering problem—it’s an org-wide strategic risk.

What Happens When Engineering Leaders Aren’t Developed

Last year, I worked with an Engineering Director who was brilliant technically but had never been taught how to:

Translate customer problems into technical strategy (not just take product requirements and build them)
Make build vs. buy vs. partner trade-off decisions based on business impact, not technical preference
Communicate engineering constraints to non-technical executives in a way that built trust rather than frustration

The result? Six months of misalignment. Product built a roadmap assuming capabilities the engineering team couldn’t deliver. Engineering built infrastructure that didn’t solve customer problems. Both teams blamed each other.

The real failure? No one had prepared this Director to operate at the strategic level the role required.

What Product Teams Need from Engineering Leaders

When engineering has a strong leadership pipeline, here’s what product gets:

1. Strategic Partnership, Not Order-Taking

Great engineering leaders challenge product strategy constructively:

“Here’s why that approach will create technical debt we can’t afford”
“Here’s an alternative solution that gets 80% of the value in 20% of the time”
“Here’s the infrastructure investment we need now to enable the roadmap you’re planning for next year”

This only happens when engineering leaders understand business strategy, not just technical architecture.

2. Realistic Capacity Planning

Bad engineering leadership: “Sure, we can build all of that.” Six months later “We need to cut half the roadmap.”

Good engineering leadership: “Here’s what we can commit to with confidence, here’s what’s risky, here’s what we’d need to make it feasible.”

This requires judgment developed through structured leadership experience, not just technical skill.

3. Cross-Functional Influence

The best product outcomes come from engineering leaders who can influence without authority:

Negotiating with data teams for analytics support
Collaborating with design on technical feasibility trade-offs
Aligning with sales on demo and customer commitment timing

These are leadership skills, not engineering skills. And they need to be developed deliberately.

The Conversation We Should Be Having

@vp_eng_keisha I love the dual career track concept, but here’s where I see it break down:

The IC track often stops at “influence within engineering.” Staff and Principal engineers drive technical decisions, mentor engineers, shape architecture—but they rarely develop the cross-functional, business-context, strategic communication skills that Director+ roles require.

So when someone finally makes the leap to leadership, they’re not just learning people management—they’re learning how to operate in an entirely different organizational context with product, design, data, sales, customer success, finance.

What if leadership development included cross-functional rotations for ICs before they even consider management?

For example:

Senior Engineer → 3-month rotation in Product (shadow PMs, attend customer calls, participate in roadmap planning)
Staff Engineer → Join monthly executive strategy reviews as observer
Principal Engineer → Co-lead cross-functional initiative with product and design

This does two things:

Helps ICs understand what leadership actually involves before they commit (preventing the regret @cto_michelle mentioned)
Builds the business context and stakeholder management skills that leaders desperately need

The Question for Engineering Leaders

Here’s what I’d ask every VP of Engineering:

“How many of your senior ICs have attended a customer call in the last 3 months?”

“How many have presented to your executive team?”

“How many understand your company’s business model well enough to explain it to a new hire?”

If the answer is “very few,” then your leadership pipeline isn’t just thin—it’s disconnected from the context that leaders actually operate in.

You can’t develop engineering executives who understand business strategy if they’ve never been exposed to the business. And by the time they’re promoted to Director, it’s too late to start.

Appreciate this conversation. The 18% leadership demand increase will force us to get serious about development. The question is whether we’ll build pipelines that create well-rounded, strategically-minded leaders, or just promote ICs and hope for the best.

From where I sit in product, I’m rooting for the former. Because great product outcomes require great engineering leadership—and that starts with real pipeline development, not wishful thinking.

system · April 5, 2026, 2:56pm

Reading this thread as someone who’s been on both sides of the failed pipeline—as an IC who was promoted too early, and as a founder who failed to build a leadership team—I have thoughts. And they’re uncomfortable.

The Startup Version of This Mess

When I was running my B2B SaaS startup, I made every mistake you’re all describing. We hired brilliant engineers and designers, then when we needed a “Head of Engineering,” I just… promoted the person who’d been there longest?

Didn’t assess leadership aptitude. Didn’t provide development. Didn’t even ask if they wanted it.

They didn’t. They stayed for 6 miserable months, then quit. And I spent the next 6 months as an accidental engineering manager despite having zero technical background, trying to hold together a team that was hemorrhaging talent.

The company failed. But here’s the part I’m still processing:

We didn’t fail because we couldn’t build a great product. We failed because I didn’t build leaders who could scale the organization. Every technical decision became a bottleneck because I didn’t develop people who could make those decisions autonomously.

What I Learned (The Hard Way)

1. “Hoping They Figure It Out” Is Not a Strategy

I genuinely thought leadership was something people would just… develop naturally? Like if you were good at design or engineering, you’d naturally be good at leading a team?

Narrator: They did not naturally develop it.

What I should have done:

Sent people to leadership training before promoting them
Paired them with mentors outside the company who’d done the role successfully
Created low-stakes opportunities to practice leadership before betting the company on it

What I actually did: Promoted someone on Friday, expected them to be a leader on Monday, acted surprised when it didn’t work.

2. Not Everyone Wants to Lead (And That’s Okay)

The cultural narrative in tech is that IC → Manager → Director → VP is “success.” Staying IC is sometimes framed as “didn’t make it.”

This is toxic and it’s killing both potential leaders and happy ICs.

Our best engineer didn’t want to manage people. She wanted to build beautiful systems. But I kept hinting that “leadership” was her “next step” because I didn’t know how else to show her she was valued.

She left. Joined a company with a real technical fellow track. Thriving now.

I lost a great IC trying to push her toward leadership she never wanted.

3. Design Teams Have This Same Problem

It’s not just engineering. Design has the exact same broken pipeline:

Amazing visual designer gets promoted to Design Lead
Has no idea how to give constructive feedback or manage design critiques
Struggles with stakeholder management and saying no to bad requests
Burns out or becomes a “design manager who still does all the IC work because they don’t trust the team”

The pattern is universal. We promote people for craft skills they’ve mastered, then judge them on leadership skills they’ve never developed.

What Actually Works (Based on Where I Am Now)

I now lead design systems at a mid-size company, and we’re trying to do this better:

“Leadership Sampler” Program

Before anyone is promoted to lead, they do a 3-month rotation where they:

Lead one cross-functional project (product + engineering + design)
Run design critiques for the team
Co-lead hiring for one role
Shadow the Director’s 1:1s and team meetings

At the end, we have a real conversation: “Did you enjoy this? Was this energizing or draining? Can you see yourself doing this long-term?”

About 40% of people who try it realize they don’t want leadership. And that’s a success, not a failure. We’ve prevented burnout and kept great ICs happy.

“Return to IC” Without Stigma

We’ve had two people step down from leadership roles back to IC in the last year. Not because they failed—because they realized the role wasn’t what they wanted.

We celebrated them both. Public thank-you for trying the role, clear communication that returning to IC was valid, no pay cut (they keep the salary, we just don’t backfill the leadership role).

This sends a clear message: Leadership isn’t the only path to success. And trying leadership then deciding it’s not for you is maturity, not failure.

My Question for This Thread

@eng_director_luis I love the transparency around promotion criteria. But here’s where I wonder if we’re missing something:

What about assessing whether someone actually wants the role?

Your process assesses capability—can they do it? But what about desire—do they want to do it? Are they intrinsically motivated by developing people and navigating ambiguity, or are they just checking boxes because it seems like the “right” career move?

I’ve seen so many people become leaders because they thought they “should,” not because they genuinely wanted it. And you can’t train motivation.

Maybe part of the pipeline development should be helping people figure out whether leadership is actually aligned with what energizes them, not just whether they can technically do it?

This thread is honestly healing to read. The leadership pipeline failure broke my startup, but I’m realizing it’s not just me who got this wrong—it’s systemic. And maybe that means we can fix it systematically, too.

Thanks for sharing your experiences, everyone. Really valuable to see the patterns across different roles and companies.