I’ve seen plenty of leadership development approaches succeed, and plenty fall flat. Some of the best work happens through solid fundamentals: structured off-site retreats that force real conversations, reading that actually sticks because it connects to what people are dealing with daily, competency frameworks that drive decisions instead of just sounding good in PowerPoint. The issue isn’t these tools themselves. The issue is when they’re treated as the complete answer instead of pieces of a larger system. What actually works is far simpler and requires less budget but considerably more intention.
The difference between a pipeline that produces leaders and a pipeline that produces résumés sent to your competitors comes down to mechanics. Specific, measurable, unglamorous mechanics.
Identifying Talent: Stop Confusing Tenure With Potential
Most organizations promote based on tenure or technical competence. That’s how you get a fantastic subject matter expert in a role where they’re miserable and ineffective. You need a different approach.
Start by identifying people who naturally gravitate toward problem solving beyond their immediate role. These aren’t always your highest performers on traditional metrics. Look for the person who starts improving a process nobody asked them to improve. The one who jumps in when coverage is tight not because they’re desperate for overtime, but because they can’t stand watching things run poorly. The one who your team naturally gravitates toward when something goes wrong.
I’ve found these signals matter:
- Someone volunteers for projects outside their normal scope. Not to pad their résumé, but because the problem bothers them. They see something broken and their instinct is to fix it.
- They ask clarifying questions about why things are done a certain way. They’re not arguing or being difficult. They genuinely want to understand the reasoning. That curiosity is foundational.
- They handle setbacks differently. When something doesn’t work, they ask what we can learn from it. Most people complain. Some people learn. The learners are the ones worth investing in.
- They make others around them better. Not by being loud about it, but through how they approach their own work and how they help peers think through problems. Culture flows from these people.
Your first tool is an actual assessment, not a gut feeling. I’m not talking about personality tests that cost three figures and tell you nothing actionable. I mean structured conversations with their current managers about specific observable behaviors. What do they actually do when they encounter a problem? How do they respond when they’re wrong? What’s their instinct when they see a teammate struggling?
Then validate it. Put them in a small developmental role first. A team lead role on a special project. A shift supervisor slot. Something with real responsibility but clear guardrails. Can they handle it? Do they want to handle it? These aren’t the same thing.
Structuring Developmental Roles: Build the Actual Pathway
Here’s what kills most pipelines: people get identified as “high potential” and then… nothing happens. They get a title bump and hope it works out. That’s not development. That’s luck.
You need sequential developmental roles that build specific capabilities. Think of it as a staircase, not a ramp.
Level 1: Team Lead or Project Owner
This is someone managing a small team or owning a defined project. Three to six months minimum. They’re responsible for hitting metrics but in a contained environment. They learn to delegate, handle basic people conversations, and see how their decisions affect outcomes. They also discover very quickly whether they actually want to lead people or if they prefer technical work. Both outcomes are valuable information.
Level 2: Shift Supervisor or Functional Lead
Now they’re managing a shift or a specific function. Larger scope, more complexity, more variables they don’t control. They’re dealing with unplanned absences, escalations, and competing priorities in real time. They’re having conversations with peers about resource allocation. They’re starting to see how the operation actually works.
Level 3: Senior Supervisor or Manager
This is where they start owning outcomes they can’t directly control. They’re managing multiple areas or larger headcount. They’re responsible for training their own replacements. They’re starting to think about strategy, not just execution. They’re sitting in meetings about things that don’t directly affect their area because they need to understand the full operation.
The specificity matters. Each role has a learning objective, not just a title and a raise. You know what you’re trying to teach them at each stage. You measure whether they’re actually learning it.
Mentorship: Make It Transactional, Not Inspirational
Most mentorship programs fail because they’re vague. “Find a mentor.” “Meet monthly.” Then nothing happens. The mentor doesn’t know what they’re supposed to be teaching. The mentee doesn’t know what they’re trying to learn. Six months pass and you’ve accomplished nothing except one more thing people feel obligated to do.
Real mentorship is specific and measurable.
The mentor gets a clear charter. Not “help develop this person” but “help them understand how to manage conflict with peers” or “teach them how to think about staffing models” or “show them what executive visibility actually looks like.” That’s concrete. The mentor knows what success looks like.
You set a timeline. Typically three to four months for a specific skill or knowledge area. That’s long enough to make progress, short enough that it doesn’t become just a coffee buddy situation. You meet every other week. You have an agenda.
The mentee prepares. They bring specific situations they’re dealing with, not vague complaints. “Here’s a conflict I have with my quality manager. Here’s what I’ve tried. What would you do differently?” That generates actual learning.
You measure it. At the end, the person can articulate what they learned and how they’ll apply it. They can point to specific decisions they made differently because of the mentorship. If they can’t, the mentorship didn’t work.
The best mentors are the people two or three levels above in similar functions. Not the CEO (too disconnected from daily reality) and not someone in a different department (different context). Someone who’s dealing with comparable problems and has figured out how to solve them.
Learning and Development: The Strategic Pathway for Senior Leadership
Most L&D departments do entry-level leadership well. New supervisor workshops. First-time manager training. Getting people acclimated to managing people instead of tasks. That’s table stakes.
Where nearly every organization falls short is developing managers who are ready to move from Manager to Senior Manager, Director, or VP level. These are people who are already executing well tactically. They know how to run a shift. They know how to hit their numbers. They know how to develop their team. But they’ve spent three to five years deep in operational execution. They haven’t been exposed to how strategy actually gets made. They haven’t thought about business models, competitive positioning, P&L, or how capital allocation works. They don’t understand why certain decisions get made at the executive level that don’t make sense from a tactical standpoint.
That’s not a failure on their part. It’s a failure of your development system.
Here’s what an actual strategic development pathway looks like:
Phase One: Exposing Strategy (Months One to Three)
Start by pulling these emerging Sr. leaders out of their functional silos. They need to understand how the entire business works, not just their operation. This is where many programs fail because they make it theoretical. You don’t want classroom learning about “strategic thinking.” You want them inside the actual strategy conversations.
Create a structured exposure program. It looks like this: they attend executive leadership meetings where strategy is discussed. Not as an observer sitting in the back, but as a participant asked to weigh in on how certain decisions affect operations. They sit in on board preparation meetings. They see what information flows upward and why. They attend finance reviews and learn how the business actually gets funded. They participate in customer strategy sessions.
This exposure teaches them something critical: most executive decisions aren’t obvious from a tactical level because executives are balancing constraints and trade offs they can’t fully articulate to everyone. Seeing this firsthand changes how someone thinks.
Phase Two: Structured Business Understanding (Months Four to Six)
Now they need to actually understand the numbers and economics. Finance doesn’t have to be complicated. What matters is they understand the business model. What’s your margin structure? Where do costs come from? What drives profitability? How does pricing work? What does a capital expenditure decision actually cost? How long until it pays back?
Partner with your finance team to create a series of sessions tailored to emerging leaders, not to finance professionals. They don’t need to become accountants. They need to understand enough to make decisions that don’t inadvertently destroy profitability.
Have them build a financial model. Something simple. If we staffed differently, how would it affect labor costs? If we implemented this technology, what would the payback period look like? If we lost this customer, what would revenue look like? Make it real and make it tied to decisions they could actually influence.
Phase Three: Cross-Functional Perspective (Months Seven to Nine)
Most operational leaders think primarily about their function. A delivery manager thinks about operations. A sales leader thinks about closing deals. A customer success manager thinks about retention. They don’t naturally understand how those functions interact or what trade-offs exist between them.
Create a rotation or assignment where they lead or participate in a cross-functional initiative. Not a committee meeting. An actual project. New product launch. Market expansion. Service delivery change. Something that requires them to negotiate with sales about capacity. Work with product about roadmap. Coordinate with customer success on go-to-market. Something where they feel the tension between functions and have to figure out how to resolve it.
This is where their mindset starts shifting from “my team hit our numbers” to “how do we move the organization toward this outcome?”
Phase Four: Leadership Perspective (Months Ten to Twelve)
At this point, you rotate them into a higher-level stretch assignment. Not necessarily a promotion yet, but a real taste of what the next level looks like. Running a larger operation. Leading across multiple locations. Managing a budget that’s not just headcount but includes capital and other discretionary spend. Presenting directly to the executive team. Owning a strategic initiative, not just executing someone else’s strategy.
The key is this assignment has executive sponsorship. A VP or Chief is actively coaching them through what senior leadership actually requires. How you build coalitions. How you navigate ambiguity. How you represent your function while thinking about the whole organization.
Making the Mindset Shift Real
The shift from tactical to strategic doesn’t happen accidentally. It requires pulling people out of the day to day regularly enough that they start asking different questions. Instead of “how do we hit our handle time target this quarter,” they start asking “what’s the right staffing model for our customer base and business strategy?” Instead of “how do we reduce turnover,” they ask “what’s our talent strategy and does turnover reduction actually matter for this segment?”
This happens when they see how executives actually think. When they sit in meetings where someone proposes something that seems operationally efficient but strategically misaligned, and they hear that get debated. When they realize that not every problem has a right answer, just better and worse trade-offs. When they understand that strategy constraints what you can do operationally, not the other way around.
The companies that move people successfully into director and VP roles aren’t moving people who suddenly became smart. They’re moving people who got exposed to how the business actually works before they were asked to think and decide at that level.
Your L&D department should own this pathway. It shouldn’t be ad hoc mentoring. It shouldn’t be hoping people figure it out. It should be as structured and intentional as your new manager training, because the stakes are equally high. You’re either developing your next generation of senior leaders, or you’re promoting people who still think tactically and then wondering why they struggle at the next level.
Assessment: How You Actually Know Who’s Ready
This is where most organizations get lazy. Ready for what? Ready according to whom? Some gut feeling? A 360 review that tells you nothing?
Build an actual readiness assessment. Make it transparent. People should know what they’re being measured against.
Here’s what I’d include:
- Operational Knowledge: Can they articulate how the operation works? Not just their piece, but the whole thing. Can they explain why you staff certain ways? How different functions depend on each other? What constraints you’re actually operating under? This takes six months minimum to genuinely understand. Ask them to walk you through a complex scenario. Something broke on the Monday morning rush. What would they do? Who would they talk to? What information do they need? What decisions can they make and what needs escalation? Their answer tells you everything.
- People Management: Have they had effective coaching conversations that changed someone’s behavior? Can they describe specific situations where they gave feedback and it actually landed? Can they talk about someone they’ve developed who got promoted? Not aspirationally, but with actual examples. Can they hire? Did they recruit people who worked out? Do they know what questions to ask to figure out if someone actually wants this job or just needs a job? Have they made a bad hire and learned from it?
- Decision Making Under Pressure: How do they respond when they don’t have all the information? Most inexperienced people wait. They gather more data hoping the right answer will appear. Leaders decide with incomplete information. They gather what matters, they decide, they course correct as new information arrives. Have them describe a decision they made where they didn’t have perfect information. What did they do? How did it work out? What would they do differently?
- Stakeholder Management: Can they have a conversation with someone who disagrees with them without it becoming personal? Can they influence peers who don’t report to them? Have they navigated a situation where they needed to tell someone something they didn’t want to hear? Talk to their peers and their boss. Would you work for this person? Not “is this person nice” but “would you trust them to make good decisions and have your back?”
- Resilience: Have they experienced a genuine failure? How did they respond? Did they blame circumstances, blame others, or did they ask what they could have done differently? Failures are the best teacher. People who don’t have any usually haven’t been challenged enough yet.
Pull the assessment together. It’s not a grade. It’s a clear picture of where they’re strong and where they still need work. It’s honest. The conversation shouldn’t be surprising to anyone involved.
The Measure of Success
You know your pipeline is working when you can fill a leadership position internally and no one questions it. Not because the person is perfect, but because everyone knows they’ve been developed for this role and they’ve proven they can do it. When the team is confident in their leadership not because of credentials but because they’ve watched them work.
You also know it’s working when people who don’t make it to leadership don’t feel discarded. They’ve developed skills that made them better at their current role. They understand why this path wasn’t right for them. They stick around.
The companies that build talent from within don’t have secret talent. They have systems that identify people early, create opportunities for real development, measure progress honestly, and promote people who’ve actually proven they’re ready. No magic. Just mechanics.
Hot Take Tuesday: Your Org Chart Doesn’t Predict Your Future
Everyone obsesses over the org chart. Who reports to whom. How many layers you have. That’s not what determines your capability. What determines it is who you’ve developed to step into roles when people leave. Which they will, by the way. People change jobs. People retire. People move cities. It happens.
The organizations that feel stable and perform well aren’t stable because they keep the same people forever. They’re stable because someone’s always ready to step up. That’s it. That’s the magic. It’s not about keeping people. It’s about making sure you always have someone who can do the job.
