Episode 15: Operator-to-Leader: Engineering a Middle-Management Pipeline That Doesn't Derail
Welcome, welcome to the People-Forward Leadership™ Podcast. If you're here for the first time, I'm thrilled you found us. And if you're a returning friend, welcome back.
Let me start with a story that might sound painfully familiar.
Six months ago, Lucy (or Larry) was your superstar. Customer satisfaction scores through the roof. Technical skills that made other team members look to her for guidance. The kind of employee who made you think, "If I could clone her, all my problems would be solved."
So you did what seemed logical: you promoted her to management.
Fast forward to today. Lucy's in your office, eyes red-rimmed, asking if she can go back to her old job. Three of your best people have requested transfers. And that customer satisfaction score? It's tanking faster than you can say "leadership development."
Sound familiar?
Well, you're not alone. I've watched this movie play out for 30 years across multiple industries, from hospital floors to biotech trials, from non-profits to transit authorities. Today, we will unpack why this keeps happening and, more importantly, how to rewrite the ending.
Here's what nobody tells you when you're building your leadership pipeline: Being great at the work and being great at leading people who do the work are completely different skill sets. It's like expecting someone who's great at playing the violin to automatically conduct the orchestra. Sure, they understand music but conducting requires an entirely different set of skills and a completely different mindset.
The research bears this out. Six out of 10 first-time managers usually crash and burn within 24 months, not because they lack intelligence or good intentions but because they haven't been set up for success from day one. Because of their superstar status, in many ways, they've been set up to fail.
Think about Lucy again. For years, her success formula was simple: work harder, know more, and deliver faster. She controlled every variable. Then, when promoted suddenly, her success depended on other people's performance, and you can't just work harder to fix things anymore (unless you decide to do everyone's job or micromanage your people to death).
As a leader you have to work through others and unfortunately this isn't something that's taught or sufficiently explained to new leaders.
Inside my People-Forward Leadership™ framework, this sits squarely in Pillar 2: Developing Others. When we leave the operator-to-leader bridge unbuilt, we lose not just a supervisor or manager but also service reliability, brand reputation, and morale in one swoop.
The key is to start before the starting line by building a leadership pipeline.
What most organizations get wrong is that they wait until the promotion happens to start developing that new leader. That's like waiting until the day of the race to start training for a marathon. It's a little late by then.
Now, I'm not saying don't train and develop your new managers; it's absolutely critical to support them once they're in their new role, and I'll share strategies for that in a moment. What I'm saying is your real competitive advantage comes from developing your pipeline of high potentials BEFORE they ever step into leadership. Think of it as priming the pump. When you prepare future leaders while they're still individual contributors, you're not scrambling to save a drowning manager or disgruntled team; you're launching someone who already knows how to swim.
In most organizations, the current "pipeline" system looks like this:
First, we still promote seniority instead of readiness. However, time served does not teach coaching skills or emotional intelligence.
Second, we rely on one-and-done training, and let me tell you, an eight-hour slideshow and a congratulatory handshake won't cut it. A new supervisor is lucky if they remember half of it when the first 3 a.m. crisis call comes in.
Third, we create peer-to-boss whiplash. Yesterday's lunch buddy is now today's "manager," and without creating space for intentional trust-building, collaboration turns into silence, and friendly banter can even become hostile.
Finally, there's no feedback loop. We promote, we hope for the best, we move on and last time I checked, hope was not a system for success.
To create a viable pipeline, you have to shift from the "let's promote our superstar and hope for the best" model to the strategic "let's promote the person who's most prepared to lead our next generation" model. It's the difference between crisis management and succession planning.
So what can you do for those high potentials "waiting in the wings?" Here are five what I call "Leadership Pipeline-Priming" activities that create leader-ready talent before they ever manage their first direct report.
1. Provide Shadow Assignments That Matter. Don't wait for promotion to expose future leaders to leadership realities. Create structured shadow experiences where high potentials sit in on difficult conversations, budget meetings, and strategic planning sessions. But here's the key: debrief afterward. Ask them, "What did you notice? What would you have done differently? What surprised you?" This transforms observation into learning.
2. Give Stretch Projects with Safety Nets. Give pipeline talent leadership experiences without the full weight of leadership responsibility. This is where you can flex your well-developed delegation skills. Have them lead a cross-functional project team, run a task force, or manage a process improvement initiative. In these situations, they can practice influence without authority, stakeholder management, and team coordination, all while you can still coach them through mistakes without major consequences.
3. Set Up Teaching Tests. Nothing reveals readiness to lead like the ability to develop others. Have your high potential create and deliver training in their area of expertise. Can they break down complex concepts? Do they adapt their style to different learners? Are they patient with questions? Teaching forces the shift from "I know" to "I can help others know"—a fundamental leadership transition.
4. Allow for Reverse Mentoring Relationships. Pair your high potential with senior leaders, but flip the script. Have them mentor executives on frontline realities, emerging technologies, or generational perspectives. This builds their confidence in adding senior-level value and helps them understand the broader organizational context they'll need as leaders. In addition, it will enhance their communication and people skills as they learn how to have cross-generational conversations. Plus, it creates advocates for their eventual promotion.
5. Employ Leadership Simulation Labs. Before pilots fly solo, they spend hours in flight simulators. Create the equivalent for your future leaders. Run monthly scenario sessions where high potentials work through real leadership challenges: "Your top performer just gave notice," "Two team members are in conflict," and "You need to deliver tough feedback to someone twice your age." Let them practice in a low-stakes environment where failure leads to learning, not lawsuits.
The beauty of these "Leadership Pipeline-Priming activities is that they become self-selecting, which means that some people will discover that they love the challenge of leadership and will lean in harder, looking for more opportunities to grow their leadership muscles. Others will realize that leading people (and problems) is not for them and that they prefer being that superstar individual contributor. They may decide to opt out of any "people leader" type promotions before you've invested in a promotion that won't work. Either outcome saves everyone time, money, and heartache.
So, if you're listening to this and thinking, "Carol, I already promoted my superstar, and they're drowning. Now what?" First, take a breath. It's not too late, but it does require intentional intervention. Here are five shifts you can help them make so they can successfully continue transitioning into their new leadership role.
Shift 1: The Mindset Revolution (Ongoing)
This identity shift will be an ongoing process. Your new manager is likely oscillating between trying to prove themselves and feeling paralyzed by the weight of responsibility. This phase is about fundamental mindset shifts:
For example, start by moving them from "I Do" to "We Grow." As individual contributors, they perfected the "I do." I solve the problem, I meet the deadline, I save the day. But leadership requires a fundamental rewiring to "We grow." We solve problems together, we develop capabilities, and we succeed as a team.
You can help with this by asking them daily, "What did you as a team accomplish today?"
Teach them to stop thinking of themselves as Firefighters and instead think of themselves as Fire Prevention Specialists. Great leaders don't run from crisis to crisis but instead design systems that prevent fires. They create clear expectations before confusion sets in, build feedback loops before performance gaps widen, and foster psychological safety before trust erodes. Asking them about the systems they're creating to handle situations is a great way to reinforce that mindset.
And the final mindset shift is to go from Solo Hero to Talent Multiplier. This one can be the hardest mindset shift to make and the hardest pill to swallow. As a leader, your individual contribution matters less than your ability to multiply others' contributions. Let me say that again: As a leader, your individual contribution matters less than your ability to multiply others' contributions. Your new superpower isn't being the smartest person in the room; it's making everyone else in the room smarter. Ask them how their team is growing, what they are learning, who they see as their next potential leader, and why. These types of questions help them focus on their people, not just their tasks.
These mindset shifts can feel radical. Even when leaders believe in these concepts, they struggle to live them out. That's why it's essential that this is not a one-and-done activity but an ongoing focus to help develop and solidify these leadership mindset shifts.
Shift 2: The Skill Sprint (Days 31-90)
Now, with the mindset shifts underway, you can focus on the five "leadership survival skills" that prevent early failure.
Teach them Delegation without Abdication: Have them start with low-risk tasks they can delegate to one of their team members using the "watch one, do one, teach one" method. You can start by modeling this with them, giving them a low-risk task and requiring brief check-ins rather than detailed oversight. Then, support them as they do the same thing with their team members.
Use Feedback as Fuel: Have them practice giving feedback to you. Teach them to start with positive feedback first (it's harder than you think), then move to constructive conversations using a framework like the SBI model (explaining the Situation, description of the Behavior, and the Impact of that Behavior on the Situation).
Teach them to Influence without Authority: Yes, they now have the authority to take the "do it because I said so" approach to management, but instead, teach them to lead with questions, not commands. This may also help break the belief that leaders have to know all the answers. The best leaders lead and teach by asking questions and helping to develop the critical thinking skills of their team members, not by having all the answers.
Be upfront about Managing Former Peers: Tell them to be upfront and address the elephant in the room directly. Help them practice that difficult conversation they'll have directing their former peers. As they start having their one-on-ones, they can say something like: "I know this is weird for both of us. Let's talk about how we make this work."
Talk about emotional intelligence, emotional regulation, and the importance of Self-Management Under Pressure: If they're melting down, their team will too. Talk about the importance of self-care, self-control, and emotional regulation. Introduce simple practices like two-minute breathing exercises before difficult conversations, end-of-day reflection rituals that let them leave work at work, and peer support partnerships that aren't grip sessions but support networks.
Incorporating these practices through ten-minute daily skill bytes instead of day-long workshops will help embed these practices and behaviors. This is where a great executive coach can be a great asset to help reinforce these skills. And by the way, if you need some support developing these practices, be vulnerable and let your new leader know that you can get coaching and work on these things together.
The next three shifts (3, 4, and 5) after the skill development focus on reinforcement and evolution. This is where most development programs abandon new leaders, right when things get real. Instead, intensify support by incorporating weekly huddles and quarter 360 feedback, introducing advanced leadership skills around change management and developing career pathways for their team, and then measuring the ROI by looking at team performance, turnover, and who is within their own leadership pipeline. Ultimately, you want to measure if they've completed the journey from "I do" to "We grow" to "They lead."
Let me share an example of how I've seen this work.
Years ago, I had the privilege of consulting with Oregon Health & Science University (OHSU), an academic health institution that's not only Portland's largest employer but also the third largest in all of Oregon. The stakes couldn't have been higher. We weren't just working with clinical managers—we were developing leaders across the entire organization: IT supervisors managing help desk teams, facilities managers overseeing maintenance crews, HR team leads, research lab managers, accounting supervisors, customer service managers, registration desk leads—every single area where someone was making that treacherous leap from individual contributor to people leader.
We developed what started as a Frontline Leader Program and has since evolved into their Frontline Manager Leadership Certificate. But here's what made it different: Instead of focusing on policies and procedures, we focused on the human side of leadership. We built the curriculum around practical, applied strategies—real communication techniques, relationship-building tools, time management for leaders (not just busy individuals), and frameworks for navigating those inevitable difficult conversations.
Most importantly, we didn't just teach and disappear. We provided ongoing coaching support to help leaders actually implement what they learned when Monday morning hit and reality set in.
The transformation was remarkable. Leaders who embraced this new way of thinking, who truly evolved beyond their individual contributor identity, didn't just survive in their new roles; they thrived. We saw measurable increases in both productivity and retention across their teams, from the research labs to the registration desks.
Working with one particular nurse manager, we introduced a simple concept called leadership rounds. They didn't replace their required clinical rounds, but instead supplemented them. After completing their clinical check-ins, managers would spend just five extra minutes with each nurse asking two questions: "What's your biggest challenge today?" and "What would make your shift 10% easier?"
By consistently asking these questions, she learned to identify and solve systemic problems and raised morale because the nurses felt valued instead of just jumping in and putting out individual fires. She created an empowered, collaborative team, conditions for everyone to do their best work, and a leadership ecosystem.
As I close out this episode, I want to share a few things you can do to start building that pipeline.
Step 1: Assess Your Situation
Ask yourself: Do I need to build a pipeline (which is proactive and preventative) or save a drowning manager (which is a reactive intervention)?
You can download my free Pipeline Scorecard at carolparkerwalsh.com/pipeline. This one-page diagnostic will help you identify exactly where your gaps are.
Then Step 2: Take One Immediate Action
If you're building a pipeline:
Identify three high potentials and schedule one "leadership pipeline-priming" activity from today's episode
Start with the Teaching Test and have them train others on their expertise
If you're saving a struggling manager:
Schedule the mindset conversation tomorrow. Let them know that leading people is fundamentally different from doing the work. They're not failing; they're just learning a completely new position.
Then implement daily check-ins for the next 30 days focused on "What did you and your team (through your leadership) accomplish today?"
The gap between a star performer and a star leader isn't a skills gap; it's a systems gap. We have systems for everything else in our organizations: sales processes, safety protocols, and service standards. But when it comes to developing leaders, we're still winging it.
As they say, great leaders aren't born; they're developed. However, that development doesn't happen through wishful thinking, sink-or-swim approaches, or one-time training events. It happens through intentional, sustained, people-forward practices that acknowledge the massive identity shift required to go from "I do" to "We grow."
Thank you for joining me today and remember, keep leading people forward. I'll see you next time.
