Leadership Pipelines Are Drying Up: How Executive Search Can Help You Build the Next Generation of Leaders
If you ask most CEOs what keeps them up at night in 2026, you’ll hear a common theme: “Do we have the leaders we’ll need three to five years from now?” The answer, increasingly, is no. Deloitte’s 2025 Global Human Capital Trends report found that two-thirds of managers and executives believed their recent hires weren’t fully prepared for the demands of the job, pointing not just to a skills gap, but an “experience gap” in critical roles.
At the same time, a Deloitte–WSJ survey of senior leaders stressed that executives must “make a bigger commitment to developing leadership at all levels” to avoid future pipeline shortages.
This is where modern executive search is quietly evolving—from filling today’s vacancies to helping organizations intentionally build tomorrow’s leadership bench.
From Skills Gap To Experience Gap
Most organizations feel the talent crunch, but the root cause is shifting. We used to talk almost exclusively about a skills gap: people lacked specific technical capabilities. Now, in many sectors, the bigger problem is experience.
Deloitte’s research shows that organizations struggle to find leaders who have actually lived through the kinds of transformations they’re asking for: integrating AI, restructuring operations, or steering through multi-year change.
Compounding the problem, the traditional path to leadership is disappearing. Many of today’s senior executives came up through apprenticeships, internships, and entry-level roles that no longer exist at the same scale.
Those rungs on the ladder have been pulled up, leaving fewer opportunities for emerging leaders to gain the depth of experience they need. That creates a widening gap between what organizations want in their next CFO, COO, or VP, and what the market can readily provide.
Executive search, when done well, helps close that experience gap—not by conjuring the mythical “perfect unicorn” candidate, but by clarifying which experiences truly matter, where they can be found, and how to assess them consistently.
Why Leadership Pipelines Are Under Pressure
Several forces are converging to strain leadership pipelines at once:
More Selective Hiring At The Top
Forbes noted that employers heading into 2026 slowed hiring and became more selective, especially in finance, technology, and corporate services. That means fewer executive moves—but much higher expectations and scrutiny for each one. Organizations want leaders who can both deliver outcomes now and grow into future roles.
Short-term Decisions With Long-term Consequences
In a widely shared commentary on the WSJ’s coverage of the job market, talent experts warned that companies that stop investing in junior and mid-level talent today “will have a huge void in people with the knowledge and skills to become the next leadership team.”
When organizations over-index on immediate efficiency—automating aggressively, trimming early-career roles—they risk starving their future leadership pipeline.
Confidence Gaps At The Executive Level
A Deloitte–WSJ survey highlighted a “confidence gap” among top executives, many of whom worry their organizations haven’t done enough to develop leaders at all levels. This uncertainty can lead to reactive hiring when a key executive leaves, rather than a proactive, pipeline-driven approach.
Executive search firms that understand these dynamics are helping clients step back from one-off hiring and ask a bigger question: What does our leadership pipeline need to look like if we want to grow, transform, or expand markets over the next decade?
How Executive Search Supports Long-term Leadership Pipelines
Forward-thinking organizations are no longer treating search assignments as isolated events. Instead, they’re using each executive search to strengthen their broader leadership strategy. That often includes:
Linking Search, Succession, And Development
Rather than writing a job description in isolation, strong search partners start by looking at the broader leadership picture: Who could grow into this role internally in two to three years? Where are the gaps? What experiences are missing across the bench? The search then serves two purposes—filling the immediate need and clarifying how to develop internal successors.
Defining “Must-have” Experiences, Not Just Titles
Modern executive search emphasizes outcome-based profiles: what the leader needs to have done, not just where they’ve worked. That might mean scaling a finance function through an acquisition, leading a technology modernization in a constrained environment, or rebuilding a disengaged team.
This focus on experiences helps organizations differentiate between candidates who have simply held big titles and those who’ve actually delivered under similar conditions.
Proactively Mapping Future-ready Talent
As hiring gets more selective, search firms increasingly engage with leaders before there’s an open requisition. Market mapping identifies executives who fit your stage, sector, and culture—even if they’re happy where they are today. That intelligence feeds both near-term searches and longer-term pipeline planning.
Supporting Leadership At Different Growth Stages
Leadership requirements for a $50M regional company are very different from those for a national, multi-entity organization. Search partners help clients sequence executive hires—finance, operations, commercial, technology—based on their growth plans, then replicate that model across locations and business units as they expand. Over time, this creates a repeatable leadership “blueprint” that can be applied in new markets and divisions.
Executive Search As A Scalable Leadership Engine
When organizations embrace this longer view, executive search starts to look less like a transaction and more like an engine. It can:
Give Mid-sized Companies Big-company Reach
Regional and growth-stage organizations may not have the name recognition of national brands, but they still need top-tier leaders. Search partners help them compete by telling a compelling story to candidates, highlighting challenge, impact, and culture—not just headlines and compensation.
Create Reusable, Multi-location Hiring Frameworks
A well-run search process can be turned into a template: intake questions, scorecards, interview structures, and onboarding playbooks that work across functions and geographies. That allows companies to replicate successful executive hires as they open new offices, expand services, or launch new entities—without reinventing the wheel each time.
Bridge Gaps Between External Hires And Internal Growth
Search is not only about bringing in outsiders. It can also surface high-potential internal leaders by applying the same evaluation rigor to internal candidates. That creates a fairer, more transparent process and often reveals people who were “hidden in plain sight.” Combined with development programs that address the experience gap, this builds a healthier, more diverse pipeline.
This scalable, system-like view of executive search is especially powerful for organizations that anticipate multiple leadership hires over several years, or that plan to replicate successful business models across new markets. It transforms what was once an ad hoc activity into a strategic capability.
Why Now Is The Time To Rethink Leadership Pipelines
The decisions companies make about leadership hiring today will echo through the next decade. As one HR leader commenting on the WSJ’s job market coverage put it, “Short term decision making often is at long term detriment. Companies not thinking about their long term talent pipeline… will find themselves suffering.”
In practical terms, that means:
- Seeing each executive search as a chance to clarify and reinforce your leadership model.
- Using external partners not just to “fill a seat,” but to benchmark your roles, compensation, and expectations against the broader market.
- Treating leadership development, succession planning, and executive hiring as parts of one integrated system.
Organizations that make this shift will not only fill today’s roles more effectively—they’ll also be building the leaders who will guide them through whatever comes next. Executive search, done thoughtfully, is one of the most powerful levers they have.
Partnering For The Next Generation Of Leadership
If your organization is starting to feel the strain of thin leadership benches, or you’re planning growth that will demand multiple new executives over the next few years, this is the moment to rethink how you approach executive hiring.
The right search partner can help you move from reactive, one-off searches to an intentional leadership pipeline strategy that scales with your business and supports multiple locations, service lines, or practices over time.
Oggi Talent specializes in executive recruiting for finance, accounting, and related leadership roles, partnering with organizations to clarify what success looks like, surface leaders who can deliver it, and build repeatable search processes that support long-term growth. If you’re ready to strengthen your leadership pipeline and build the next generation of executives for your organization, Oggi Talent is ready to help you get there—contact us today!.
FAQs: Executive Search And Leadership Pipelines
Q: What is a leadership pipeline in executive hiring?
A: A leadership pipeline is the planned, ongoing flow of leaders who can step into critical roles as the organization evolves. It includes current executives, ready-now successors, and emerging talent being developed for future leadership positions. Executive search supports this by identifying and attracting external leaders while clarifying what experiences internal talent needs to grow into those roles.
Q: How can executive search help close the experience gap?
A: Executive search partners help define which experiences matter most for a role—such as leading through transformation, scaling a function, or managing complexity—and then systematically seek out candidates who have demonstrated those outcomes. They also provide market insights into how other organizations are building and buying experience, helping you decide when to develop internal talent and when to hire externally.
Q: When should a company start thinking about leadership pipelines, not just one-off executive hires?
A: You should start thinking about the pipeline as soon as you anticipate multiple executive moves over the next few years—due to growth, retirements, restructuring, or expansion into new markets. If you’re opening new offices, adding service lines, or planning regional or national growth, treating each executive hire as part of a bigger pattern will save time, reduce risk, and create more consistency across your leadership team.
Q: Can smaller or mid-sized companies really build robust leadership pipelines?
A: Yes. You don’t need a Fortune 500 budget to think strategically. Smaller and mid-sized organizations can partner with executive search firms to build scalable frameworks, reuse successful profiles and processes across locations, and tap into broader talent networks than they could reach on their own. Over time, this creates a leadership pipeline that grows alongside the business.
Q: What should we look for in an executive search partner to support our leadership pipeline, not just a single hire?
A: Look for a firm that asks about your multi-year strategy, not just the current vacancy; that can support multiple types of executive roles across functions; and that offers structured, repeatable processes rather than one-off “black box” searches. Ask how they handle market mapping, internal vs. external talent, and how they help clients build systems that can be replicated as the organization grows or expands into new regions.
References
- Dennison, Kara. “A Look Back On The 2025 Job Market And How To Prepare For 2026.” Forbes, December 16, 2025. https://www.forbes.com/sites/karadennison/2025/12/16/a-look-back-on-the-2025-job-market-and-how-to-prepare-for-2026/
- “Closing the Experience Gap Through Talent Development.” Deloitte 2025 Global Human Capital Trends. Deloitte Insights, 2025. https://www.deloitte.com/us/en/insights/focus/human-capital-trends/2025/closing-the-experience-gap-through-talent-development.html
- “Confidence Gap Among America’s Top Executives: Deloitte Survey.” The Wall Street Journal (Deloitte WSJ Intelligence), 2025. https://deloitte.wsj.com/riskandcompliance/confidence-gap-among-americas-top-executives-deloitte-survey-1416286910
- “A Look At The 2025 Job Market For The Class Of 2026.” Commentary on The Wall Street Journal coverage, Steve Cadigan via LinkedIn, November 16, 2025. https://www.linkedin.com/posts/cadigan_career-ladder-ai-activity-7396206039051907072-lGPI
- “Navigating Selective Hiring: How Executive Search Helps Companies Win in a Slowdown.” Oggi Talent Blog, January 2026. https://oggitalent.com/navigating-selective-hiring-how-executive-search-helps-companies-win-in-a-slowdown/
- “Building Leadership Pipelines: How Executive Search Partners Support Succession and Development.” Oggi Talent Blog, January 2026. https://oggitalent.com/building-leadership-pipelines-with-executive-search-partnershow-executive-search-partners/
- “Executive Search as a Service Line: How Middle-Market Companies Can ‘Plug In’ Strategic Leadership Faster.” Oggi Talent Blog, February 2026. https://oggitalent.com/executive-search-as-a-plug-in-capability/
- “August 2025 Job Market Insights & Trends.” Boutique Recruiting Blog, November 30, 2025. https://www.boutiquerecruiting.com/august-2025-job-market-trends-update/
- “Navigating 2025: Key Trends Shaping the Future of Executive Recruiting.” Hunt Scanlon Media, March 19, 2025. https://huntscanlon.com/navigating-2025-key-trends-shaping-the-future-of-executive-recruiting/
- “Executive Hiring Checklist: Series A–C Growth Stage Guide.” Hager Executive Search, February 8, 2026. https://hagerexecutivesearch.com/leadership-consulting/executive-search-hiring-executives-growth-stage-series-a-c/