Newsletter #14 • Development

Your Leadership Pipeline is Broken

Why promoting your best ICs creates your worst managers.

The LinkedIn Summary

Ranjit is CEO of a 200-person manufacturing company. Business is stable, profitable.

But when he looks at his senior leadership team, he sees a crisis:

COO is 58. Retiring in 3 years.

CFO is 62. Retiring in 2 years.

VP of Operations is 60. Retiring in 4 years.

The next layer down? Mid-level managers in their 30s. Great at their jobs.

But they lack: Strategic decision-making. Board communication. Cross-functional leadership.

Ranjit has a "leadership vacuum."

Full framework to build your leadership pipeline inside.

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THE CASE: The Leadership Vacuum You Didn't See Coming

Ranjit is the CEO of a 200-person manufacturing company. His business is stable, profitable, and growing steadily. But when he looks at his senior leadership team, he sees a looming crisis:

His COO is 58. Planning to retire in 3 years. His CFO is 62. Retiring in 2 years. His VP of Operations is 60. Retiring in 4 years.

The next layer down? Mid-level managers in their mid-30s. Great at their jobs. But they lack strategic decision-making experience, board-level communication skills, cross-functional leadership capability, and long-term vision.

His options: (1) Promote unprepared managers High risk of failure. (2) Hire externally Expensive, slow, cultural risk. (3) Do nothing and hope Guarantee of crisis.

He chose option 4: Build a leadership pipeline deliberately.

The Core Insight

Deloitte found that only 13% of companies believe they have robust succession plans in place. Senior leadership isn't learned in a classroom. It's developed through exposure, practice, and mentorship. The gap isn't knowledge—it's exposure and practice.

The Experience Gap

Mid-Level Manager Senior Leader
Executes within their domain Thinks cross-functionally and strategically
Manages people and processes Manages complexity and ambiguity
Solves known problems Navigates unknown problems
Reports to leadership Makes company-level decisions
Communicates to their team Communicates to board, investors, stakeholders

The Evidence

Only 13% have robust succession plans (Deloitte)

50% higher financial performance with strong pipelines (HBR)

6-9 months to fill executive roles externally (Spencer Stuart)

Internal hires perform 20% better (LinkedIn)

70% faster readiness with stretch assignments (DDI)

3X higher retention with executive mentorship (Gartner)

Build the Leadership Pipeline

Step 1: Identify High-Potential Leaders (60 minutes)

Who are your 3-5 mid-level managers who could step into senior roles in 3-5 years?

Criteria:

  • Strong domain expertise
  • Respected by peers and teams
  • Demonstrated ability to learn and grow
  • Alignment with company values
  • Aspiration to grow (not everyone wants senior leadership)

Ask them: "In 5 years, do you see yourself in a senior leadership role here?"

Step 2: Design "Shadow Projects" (90 minutes)

Assign high-potential managers to observe a senior leader managing a critical initiative for 4-8 weeks.

Example: "We're evaluating a strategic partnership with Company X."

  • High-potential attends all meetings as an observer (not participant)
  • Observes how decisions are made, questions asked, stakeholders managed
  • Writes a 2-page reflection: "What did I learn about senior leadership?"

Step 3: Create Cross-Functional Stretch Assignments (60 minutes)

Give managers projects outside their domain:

  • Engineering Manager Lead a customer feedback initiative with Sales and Product
  • Marketing Manager Analyze and propose improvements to the sales process
  • Operations Manager Design a new employee onboarding experience with HR

Why: Forces them to think beyond their silo, builds empathy for other functions, tests ability to lead without direct authority.

Step 4: Implement "Leadership Challenges" (90 minutes)

Once per quarter, run a mini-project:

  • Present a real company problem (e.g., "How do we reduce customer churn by 10%?")
  • Form small, cross-functional teams of high-potentials
  • Give them 2 weeks to analyze, develop solution, present to senior leadership
  • Senior leaders provide feedback on how they approached the problem

Step 5: Assign Executive Mentors (30 minutes)

Pair each high-potential with a senior leader for 6 months. 30-minute 1:1 every other week. The mentee brings challenges, questions, or decisions. The mentor coaches.

The Experiment: Board Meeting Observer Program

For the next 6 months:

Once per quarter, invite one high-potential manager to attend the board meeting as a silent observer.

  • They sit in the room, listen, take notes
  • After the meeting, debrief with the CEO: "What did you notice? What surprised you?"

Why it works:

  • They see how the CEO communicates at the highest level
  • They understand what the board cares about
  • They gain perspective on strategic priorities
  • It demystifies senior leadership

Building a "Talent Factory"

The companies that win long-term don't just hire great leaders. They build them.

From Good to Great: Great companies are "talent factories"—they systematically develop leaders at every level.

From The Five Dysfunctions: Great leadership teams require trust. Trust is built through shared experiences. Shadow projects, stretch assignments, and mentorship create those experiences.

Sources & References

  • Collins, Jim. Good to Great. HarperBusiness, 2001.
  • Lencioni, Patrick M. The Five Dysfunctions of a Team. Jossey-Bass, 2002.
  • Deloitte Insights. Global Human Capital Trends: Succession Planning. 2023.
  • Harvard Business Review. "Building a Strong Leadership Pipeline." 2022.
  • LinkedIn Learning. Talent Trends Report. 2023.
  • Spencer Stuart. Executive Search and Succession Report. 2023.

Key Takeaways

  • Senior leadership isn't learned in a classroom—it's developed through exposure and practice
  • Shadow projects give high-potentials visibility into strategic decision-making
  • Cross-functional stretch assignments build breadth and empathy
  • Executive mentorship transfers tacit knowledge that can't be taught
  • Build your leadership pipeline deliberately—and you'll never face a leadership vacuum

Next Newsletter

When AI Creates More Cultural Friction Than Innovation

Read Newsletter #12

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