Succession planning often fails because organizations wait too long or rely on outdated assumptions about leadership transitions. This article compiles practical advice from industry leaders who have successfully prepared their teams for change. Their insights cover everything from building autonomous systems to testing future leaders under real-world pressure.

  • Stretch People in the Messy Middle
  • Actively Use Your Plan, Don’t File It
  • Cultivate Leadership Through Shadow Co-Leadership Daily
  • Build Systems That Thrive Without You
  • Rotate Emerging Leaders Through Challenging Projects
  • Rotate Ownership To Spread Critical Skills
  • Identify Leaders Through Learning Agility Early
  • Develop Leaders Before You Need Them
  • Simulate Crisis Scenarios With Multiple Candidates
  • Pick Curious People Over Senior Employees
  • Align Business Continuity With Personal Development
  • Establish Readiness Benchmarks For Timely Transitions
  • Nurture Analytical Thinkers With Data Clarity
  • Design Teams That Don’t Need Founders
  • Test Leadership Potential Under Real Pressure
  • Ensure Cross-Functional Readiness Across Departments

Stretch People in the Messy Middle

Succession planning isn’t just about having a list of names in a drawer; it’s about building people before you need them. In my experience, the biggest mistake leaders make is waiting until someone resigns to start thinking about who’s next. By then, you’re already behind.

At MTD, I’ve always treated succession planning as part of everyday leadership. Every manager is expected to be developing their “shadow”—someone who could step into their role tomorrow if needed. That doesn’t mean cloning yourself; it means stretching people, giving them exposure, and letting them make real decisions before it’s “safe.”

Here’s what I’ve learned: you can’t spot future leaders in a training room; you spot them in the messy middle of real challenges. I’ll often throw someone into a project slightly above their comfort zone just to see how they think under pressure. The ones who thrive there are the ones I invest in.

So my best practice is this: succession planning shouldn’t be a secret exercise in HR. It should be a living, breathing part of your culture. Everyone should know growth is expected, not just for the business but for themselves. That way, when the time comes for someone to move up, it’s not a surprise—it’s a natural next step.

Sean McPheat

Sean McPheat, Founder & CEO, MTD Training

Actively Use Your Plan, Don’t File It

The biggest lesson I have gleaned from leading succession planning frameworks is that real succession planning requires active engagement, not just documentation. I honed this lesson when analyzing a company’s leadership transitions and noting that despite having a formal succession plan, we were primarily filling vacancies with external hires rather than developing internal talent.

To address this, I implemented specific action plans to better utilize our existing framework. We began investing deliberately in each person identified in the succession plan, accelerating their development toward their targeted future roles. I also shifted our review cadence from annual to quarterly discussions with our executive team, ensuring everyone knew who these high-potential leaders were and their projected career paths.

The results were swift and meaningful. Within months, we saw a significant increase in leadership positions being filled through internal mobility. Employee engagement metrics also improved as team members recognized genuine long-term career opportunities within our organization.

My key takeaway from this experience is straightforward: don’t just HAVE a succession plan, actively USE it. The plan itself has little value without consistent implementation and follow-through. Treating succession planning as an ongoing strategic priority rather than a compliance exercise makes all the difference.

Angela Heyroth

Angela Heyroth, Principal, Talent Centric Designs

Cultivate Leadership Through Shadow Co-Leadership Daily

Succession planning begins with trust and unfolds through shared ownership. We focus less on replacement and more on continuity. Leadership is not handed over; it is cultivated through collaboration, emotional intelligence, and a deep understanding of the brand’s rhythm.

One practice that continues to shape our approach is shadow leadership. Emerging voices are invited to co-lead projects, contribute to strategic decisions, and hold space for both creative vision and operational clarity. This process allows future leaders to grow within the brand’s culture rather than outside of it. When transition becomes necessary, it feels less like a shift and more like a natural evolution.

The most valuable lesson has been this: succession works best when it is not delayed until departure. It thrives when nurtured in the everyday, when mentorship is woven into the workflow, and when leadership is seen as a shared responsibility rather than a solitary role.

Sahil Gandhi

Sahil Gandhi, CEO & Co-Founder, Blushush Agency

Build Systems That Thrive Without You

Being the founder and managing consultant at spectup, I see succession planning not as preparing someone to take your place, but as preparing the company to thrive without depending on any single person, including you. In startups, leadership often becomes personality-driven; decisions orbit around the founder’s instincts, relationships, or vision. That works in the early days, but it becomes a risk as the company matures. I learned this when one of our key consultants had to step back unexpectedly. We realized how much operational knowledge lived in people’s heads rather than in our systems. It was a wake-up call that culture, not contingency, should drive succession.

Since then, my approach has been to make leadership development an everyday habit rather than an emergency measure. At spectup, we identify potential leaders early and involve them in strategic decisions long before they’re officially in charge of anything. They sit in client briefings, join investor discussions, and get space to make independent calls. I remember one of our project leads who once froze in her first big client meeting. Instead of shielding her, we debriefed together afterward, turning it into a learning moment. Six months later, she was leading a team through a seven-figure fundraising project.

The best practice I’ve learned is to document leadership thinking, not just tasks. We keep internal “decision logs” where key choices and rationales are recorded, making it easier for anyone stepping in to understand the why behind the what. Succession, in my experience, isn’t about replacing people; it’s about replicating clarity and confidence. When everyone on your team understands not only what to do but why it matters, continuity becomes natural, not forced.

Niclas Schlopsna

Niclas Schlopsna, Managing Consultant and CEO, spectup

Rotate Emerging Leaders Through Challenging Projects

My approach to succession planning is to treat it as leadership development, not replacement planning. That mindset makes the whole organization stronger and less dependent on single points of failure. One best practice that’s worked for us is exposure through rotation. We regularly give potential leaders temporary ownership of projects outside their comfort zone—whether it’s running a client pitch, leading a cross-functional sprint, or managing a budget cycle. It reveals how they think under pressure and gives them a safe space to grow before the stakes get higher.

Daniel Haiem

Daniel Haiem, CEO, App Makers LA

Rotate Ownership To Spread Critical Skills

I take succession way more seriously now because I learned the hard way that scaling gets stuck if only one person can do a certain thing. At SourcingXpro in Shenzhen, I started building second layers under every critical function early, even when we were still lean and only running on 5 percent commission sourcing and free inspections. I rotate ownership on key supplier relationships every quarter so skills get spread, not siloed. Honestly, that reduced risk so fast and saved us when one senior buyer left in 2023. My best lesson is this: succession planning should start years before you need it, not after someone gives notice.

Mike Qu

Mike Qu, CEO and Founder, SourcingXpro

Identify Leaders Through Learning Agility Early

At Invensis Learning, leadership continuity has always been viewed as a strategic necessity rather than an afterthought. The most effective approach I’ve found to succession planning is to start early—identifying potential leaders not only by their current performance but by their learning agility and ability to adapt to change. A recent Deloitte survey showed that organizations with formal succession programs are 1.6 times more likely to achieve above-average business results, and that insight resonates deeply with my experience. Encouraging emerging leaders to take ownership of real projects, exposing them to cross-functional challenges, and providing structured mentorship ensures readiness when the time comes. The biggest lesson learned is that succession planning isn’t about replacing leaders—it’s about cultivating a culture that consistently produces them.

Arvind Rongala

Arvind Rongala, CEO, Invensis Learning

Develop Leaders Before You Need Them

My approach to succession planning is to develop leaders before you need them. At Otto Media, we let team members make small, meaningful decisions early. This helps them gain confidence and context before taking on bigger roles. The best lesson I’ve learned is that succession isn’t a handover event; it’s a continuous process of mentoring and trust-building. When people already see themselves as leaders, the transition feels natural and the business doesn’t miss a beat.

Callum Gracie

Callum Gracie, Founder, Otto Media

Simulate Crisis Scenarios With Multiple Candidates

Our succession planning is rooted in “Scenario-Based Shadowing.” Instead of just naming a successor, we identify two to three high-potential employees for each key role and have them participate in simulated crisis or opportunity scenarios.

A best practice we’ve learned is to mandate cross-functional shadowing at the senior level.

For example, our Head of Operations spends one week a quarter “shadowing” the Head of Design, making key inventory decisions based on design trends. This ensures that potential future CEOs don’t just understand their vertical, but they grasp the full, holistic customer journey, from creative concept to physical delivery, which is vital for a personalized goods company like ours.

Nir Appelton

Nir Appelton, CEO, Adorb Custom Tees

Pick Curious People Over Senior Employees

I start succession planning way earlier than feels necessary by having leaders document their playbooks and train a “shadow” on key processes. The big lesson: don’t just pick the most senior person; pick the most curious person, the one already asking how the business works. That makes transitions quieter, faster, and way less emotional.

Eric Turney

Eric Turney, President / Sales and Marketing Director, The Monterey Company

Align Business Continuity With Personal Development

Effective succession planning aligns business continuity with personal development and cultural integrity. We prepare successors early to maintain direction without disruption or hesitation. Leadership transitions must feel natural, guided by mentorship rather than urgency. Investing in growth secures stability that preserves innovation through generational shifts. Consistency becomes achievable when learning precedes leadership appointment or promotion.

At our organization, mentoring programs pair emerging managers with senior advisors for perspective. Experience exchange ensures successors carry values alongside operational expertise and discipline. Our program emphasizes adaptability since markets evolve faster than experience alone. Each leader learns that confidence grows through accountability and humility combined. Succession planning safeguards purpose through deliberate transfer of trust and vision.

Ender Korkmaz

Ender Korkmaz, CEO, Heat&Cool

Establish Readiness Benchmarks For Timely Transitions

Succession requires foresight supported by structure, ensuring longevity beyond individual leadership. We identify potential early and nurture it through progressive exposure to responsibility. Candidates learn by leading initiatives under mentorship from senior executives directly. This experiential approach tests capability under authentic conditions, revealing genuine potential. Evaluation focuses equally on character, vision, and capacity for collaboration.

A lesson learned was that timing determines success within leadership transitions. Delays breed complacency, while premature shifts weaken institutional confidence among teams. Establishing readiness benchmarks anchors decisions in clarity and fairness across governance. Structured timelines ensure successors enter roles equipped and respected by peers. Preparation and timing together define sustainable leadership evolution and stability.

Lord Robert Newborough

Lord Robert Newborough, Owner, Rhug Organic Farm & Rhug Ltd

Nurture Analytical Thinkers With Data Clarity

My approach to succession planning focuses on nurturing analytical thinkers who can connect creativity with measurable outcomes. In digital marketing, leadership requires more than vision, as it also depends on understanding audience behavior and market patterns. I guide emerging leaders to make decisions based on data trends and real-time insights to ensure strategies are innovative.

One lesson I have learned is that clarity drives confidence and growth. When team members understand the reason behind each metric, they develop sharper judgment. Regular campaign reviews help transform numbers into meaningful stories that guide better decision-making. This continuous learning process shapes leaders who think strategically and creatively while staying aligned with evolving digital trends.

Vaibhav Kakkar

Vaibhav Kakkar, CEO, Digital Web Solutions

Design Teams That Don’t Need Founders

My approach to succession planning is less about preparing someone to replace me and more about designing a team that doesn’t need me. A lot of founders think succession means finding “the next you,” but that mindset usually creates dependency, not leadership. I’ve learned that real succession planning is about distributing context — making sure knowledge, decision frameworks, and values are embedded in the culture rather than locked in a single person’s head.

One practice that’s worked well for us is what I call “shadow ownership.” It’s when a team member unofficially “owns” a system or function before it’s formally theirs. They make calls, run meetings, even fail in small ways — but with a safety net. It gives them a low-stakes environment to develop judgment and confidence before the title ever changes.

What’s funny is, the best succession plans often make your own role start to feel redundant. That’s a good thing. It means the company’s maturing. I think the goal isn’t to build successors — it’s to build systems that naturally create them.

Derek Pankaew

Derek Pankaew, CEO & Founder, Listening.com

Test Leadership Potential Under Real Pressure

We employ the “Leadership Test Drive” approach. I think leadership potential reveals itself under REAL pressure, so I put up-and-coming talent in “make or break” situations: usually in high-value client pitches, brand launches, or strategic planning sessions. These experiences reveal how they think, adjust, and even lead without a safety net.

I’ve even had a senior media account manager who needed a new vision. I stepped back but remained open to coaching. In that situation, observing her do staff meetings, reconcile arguments, and regain the client’s confidence began to convince me of her potential for leadership. This experience not only prepared her for a future leadership position but also demonstrated that succession planning should be done on the field, not in conference rooms.

Matt Bowman

Matt Bowman, Founder, Thrive Local

Ensure Cross-Functional Readiness Across Departments

I emphasize cross-functional readiness instead of relying on a single successor. Our approach ensures that multiple leaders understand overlapping roles, key functions, and strategic priorities. This creates a seamless transition when someone leaves and prevents operational gaps or bottlenecks. It also builds confidence among team members who see growth opportunities within the organization.

A valuable lesson I learned is to avoid depending on one “go-to” leader because it can make others feel excluded or less capable. Encouraging shared leadership creates a sense of ownership across departments. It allows leaders to develop strategic thinking and decision-making skills. By broadening the leadership base, we build organizational resilience and ensure that success is never dependent on a single individual.

Christopher Pappas

Christopher Pappas, Founder, eLearning Industry Inc

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