The Work We Won’t Let Our Teams Do
The Work We Won’t Let Our Teams Do
The Work We Won’t Let Our Teams Do
The Work We Won’t Let Our Teams Do
Some of my best front-line leaders are my company's largest hidden risk.
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Some of my best front-line leaders are my company's largest hidden risk.
Share
Some of my best front-line leaders are my company's largest hidden risk.
Every one of them is excellent in front of customers, cool and articulate when pressed. They convert detractors into champions. Penetrate new lines of business. Save faltering QBRs.
When an amazing leader takes over, everything falls into place.
But over time, these heroics impact their teams. I run a Customer Success organization. When my Customer Success Managers (CSMs) outsource their most difficult work to their Manager, Director or VP, they unintentionally reduce their roles to logistics like scheduling meetings and sending follow-up summaries. Manger heroics compensate for skill gaps, hiding underperformers and limiting professional growth. And when the leader's calendar becomes too full—or they are promoted or quit—what's left isn't a high-performing team, but a group of capable yet dependent CSMs waiting to be saved.
“Manger heroics compensate for skill gaps, hiding underperformers and limiting professional growth.”
Every one of them is excellent in front of customers, cool and articulate when pressed. They convert detractors into champions. Penetrate new lines of business. Save faltering QBRs.
When an amazing leader takes over, everything falls into place.
But over time, these heroics impact their teams. I run a Customer Success organization. When my Customer Success Managers (CSMs) outsource their most difficult work to their Manager, Director or VP, they unintentionally reduce their roles to logistics like scheduling meetings and sending follow-up summaries. Manger heroics compensate for skill gaps, hiding underperformers and limiting professional growth. And when the leader's calendar becomes too full—or they are promoted or quit—what's left isn't a high-performing team, but a group of capable yet dependent CSMs waiting to be saved.
“Manger heroics compensate for skill gaps, hiding underperformers and limiting professional growth.”
Every one of them is excellent in front of customers, cool and articulate when pressed. They convert detractors into champions. Penetrate new lines of business. Save faltering QBRs.
When an amazing leader takes over, everything falls into place.
But over time, these heroics impact their teams. I run a Customer Success organization. When my Customer Success Managers (CSMs) outsource their most difficult work to their Manager, Director or VP, they unintentionally reduce their roles to logistics like scheduling meetings and sending follow-up summaries. Manger heroics compensate for skill gaps, hiding underperformers and limiting professional growth. And when the leader's calendar becomes too full—or they are promoted or quit—what's left isn't a high-performing team, but a group of capable yet dependent CSMs waiting to be saved.
“Manger heroics compensate for skill gaps, hiding underperformers and limiting professional growth.”
There are legitimate reasons this happens beyond individual behavior that extends beyond Customer Success and into every business function. It is often baked into how we scale. For me personally, I've built large teams on shoe-string budgets by hiring early-career talent, near and offshore teams, or through BPOs. When I'm able to invest in my team's continued development, this works really well. But attrition, re-orgs, or GTM pivots can sideline growth, requiring heroes to keep things afloat.
I’ve experienced similar patterns when early-stage organizations mature and a generalist CSM's work splits out to specialists handling renewals, onboarding, or technical delivery. The commercial or project-oriented tasks that once filled their days as jacks-of-all-trades leave them needing to learn or rebuild skills that drive proactive value.
Even senior CSMs can find themselves trapped when using their Director or VP's title to elevate customer contacts or open doors they can't otherwise crack. I’ve seen that seniority turn into an expectation for the customer, reshaping the relationship for the worse. When customers bypass their CSMs in favor of their boss, even the best of the best, sensing their diminished value, drop accountability. This is particularly dispiriting if that CSM prepares less, cares less, or resigns.
“Even senior CSMs can find themselves trapped when using their Director or VP's title to elevate customer contacts or open doors they can't otherwise crack.”
There are legitimate reasons this happens beyond individual behavior that extends beyond Customer Success and into every business function. It is often baked into how we scale. For me personally, I've built large teams on shoe-string budgets by hiring early-career talent, near and offshore teams, or through BPOs. When I'm able to invest in my team's continued development, this works really well. But attrition, re-orgs, or GTM pivots can sideline growth, requiring heroes to keep things afloat.
I’ve experienced similar patterns when early-stage organizations mature and a generalist CSM's work splits out to specialists handling renewals, onboarding, or technical delivery. The commercial or project-oriented tasks that once filled their days as jacks-of-all-trades leave them needing to learn or rebuild skills that drive proactive value.
Even senior CSMs can find themselves trapped when using their Director or VP's title to elevate customer contacts or open doors they can't otherwise crack. I’ve seen that seniority turn into an expectation for the customer, reshaping the relationship for the worse. When customers bypass their CSMs in favor of their boss, even the best of the best, sensing their diminished value, drop accountability. This is particularly dispiriting if that CSM prepares less, cares less, or resigns.
“Even senior CSMs can find themselves trapped when using their Director or VP's title to elevate customer contacts or open doors they can't otherwise crack.”
There are legitimate reasons this happens beyond individual behavior that extends beyond Customer Success and into every business function. It is often baked into how we scale. For me personally, I've built large teams on shoe-string budgets by hiring early-career talent, near and offshore teams, or through BPOs. When I'm able to invest in my team's continued development, this works really well. But attrition, re-orgs, or GTM pivots can sideline growth, requiring heroes to keep things afloat.
I’ve experienced similar patterns when early-stage organizations mature and a generalist CSM's work splits out to specialists handling renewals, onboarding, or technical delivery. The commercial or project-oriented tasks that once filled their days as jacks-of-all-trades leave them needing to learn or rebuild skills that drive proactive value.
Even senior CSMs can find themselves trapped when using their Director or VP's title to elevate customer contacts or open doors they can't otherwise crack. I’ve seen that seniority turn into an expectation for the customer, reshaping the relationship for the worse. When customers bypass their CSMs in favor of their boss, even the best of the best, sensing their diminished value, drop accountability. This is particularly dispiriting if that CSM prepares less, cares less, or resigns.
“Even senior CSMs can find themselves trapped when using their Director or VP's title to elevate customer contacts or open doors they can't otherwise crack.”
While we all need leaders who aren't afraid to roll up their sleeves, we also need leaders who aren't afraid not to. When closely attached to too many customers, their span of control shrinks to very small teams. As our most expensive resources, a CS organization that relies on large management structures artificially limits its return on investment and risks downsizing.
While we all need leaders who aren't afraid to roll up their sleeves, we also need leaders who aren't afraid not to. When closely attached to too many customers, their span of control shrinks to very small teams. As our most expensive resources, a CS organization that relies on large management structures artificially limits its return on investment and risks downsizing.
While we all need leaders who aren't afraid to roll up their sleeves, we also need leaders who aren't afraid not to. When closely attached to too many customers, their span of control shrinks to very small teams. As our most expensive resources, a CS organization that relies on large management structures artificially limits its return on investment and risks downsizing.
Leading, Better
Solving this requires those in charge to make a conscious shift from being heroes to creating heroes. I've struggled at times to find the right balance, but have adopted a series of heuristics to help achieve this:
First, I encourage my management team to celebrate consistent performances over big turn-arounds that required their rescue. Second, while Customer Success leaders will always meet with customers, when there, they should enable CSMs to lead the conversation. One of the simplest changes I've seen work: define in advance who owns the agenda—and bias towards the CSM. Practically, this means no matter where the conversation turns, the CSM drives the conversation—fielding questions and looping the leader in, rather than having customers address them directly. Debrief and coach afterwards. It's a small shift from taking over, but it gives CSMs room to stretch, experience discomfort, and be challenged. That said, not every CSM will make it. Coaching out those too comfortable in legacy habits is difficult and often emotional, but essential to scaling.
“No matter where the conversation turns, the CSM drives the conversation—fielding questions and looping the leader in, rather than having customers address them directly.”
Leading, Better
Solving this requires those in charge to make a conscious shift from being heroes to creating heroes. I've struggled at times to find the right balance, but have adopted a series of heuristics to help achieve this:
First, I encourage my management team to celebrate consistent performances over big turn-arounds that required their rescue. Second, while Customer Success leaders will always meet with customers, when there, they should enable CSMs to lead the conversation. One of the simplest changes I've seen work: define in advance who owns the agenda—and bias towards the CSM. Practically, this means no matter where the conversation turns, the CSM drives the conversation—fielding questions and looping the leader in, rather than having customers address them directly. Debrief and coach afterwards. It's a small shift from taking over, but it gives CSMs room to stretch, experience discomfort, and be challenged. That said, not every CSM will make it. Coaching out those too comfortable in legacy habits is difficult and often emotional, but essential to scaling.
“No matter where the conversation turns, the CSM drives the conversation—fielding questions and looping the leader in, rather than having customers address them directly.”
Leading, Better
Solving this requires those in charge to make a conscious shift from being heroes to creating heroes. I've struggled at times to find the right balance, but have adopted a series of heuristics to help achieve this:
First, I encourage my management team to celebrate consistent performances over big turn-arounds that required their rescue. Second, while Customer Success leaders will always meet with customers, when there, they should enable CSMs to lead the conversation. One of the simplest changes I've seen work: define in advance who owns the agenda—and bias towards the CSM. Practically, this means no matter where the conversation turns, the CSM drives the conversation—fielding questions and looping the leader in, rather than having customers address them directly. Debrief and coach afterwards. It's a small shift from taking over, but it gives CSMs room to stretch, experience discomfort, and be challenged. That said, not every CSM will make it. Coaching out those too comfortable in legacy habits is difficult and often emotional, but essential to scaling.
“No matter where the conversation turns, the CSM drives the conversation—fielding questions and looping the leader in, rather than having customers address them directly.”
I trust that my front-line is smarter and more aware of our customers' business than I am. The best advice I was ever given was to selectively free front-line managers out from the field so they can build strategic programs that improve their team's results. The greatest leaders are resistant to this change, because it's counter-intuitive for them to step away from customers—even briefly—to build a better, more scalable experience. But it works. Case-in-point: one of my leaders used this opportunity to build a structured mentor program that paired CSMs to help our managers scale, promote independence, and prepare the next generation of managers. An outsized impact that would’ve been impossible to spot or action from the frontline.
Helping my leaders recognize and solve their innate desire to save their teams from every challenging situation is as much my responsibility as it is theirs. We get comfortable with what we do best, and for many managers that means taking control. It is a quiet form of micromanagement to play the hero over and over.
“It is a quiet form of micromanagement to play the hero over and over.”
I trust that my front-line is smarter and more aware of our customers' business than I am. The best advice I was ever given was to selectively free front-line managers out from the field so they can build strategic programs that improve their team's results. The greatest leaders are resistant to this change, because it's counter-intuitive for them to step away from customers—even briefly—to build a better, more scalable experience. But it works. Case-in-point: one of my leaders used this opportunity to build a structured mentor program that paired CSMs to help our managers scale, promote independence, and prepare the next generation of managers. An outsized impact that would’ve been impossible to spot or action from the frontline.
Helping my leaders recognize and solve their innate desire to save their teams from every challenging situation is as much my responsibility as it is theirs. We get comfortable with what we do best, and for many managers that means taking control. It is a quiet form of micromanagement to play the hero over and over.
“It is a quiet form of micromanagement to play the hero over and over.”
I trust that my front-line is smarter and more aware of our customers' business than I am. The best advice I was ever given was to selectively free front-line managers out from the field so they can build strategic programs that improve their team's results. The greatest leaders are resistant to this change, because it's counter-intuitive for them to step away from customers—even briefly—to build a better, more scalable experience. But it works. Case-in-point: one of my leaders used this opportunity to build a structured mentor program that paired CSMs to help our managers scale, promote independence, and prepare the next generation of managers. An outsized impact that would’ve been impossible to spot or action from the frontline.
Helping my leaders recognize and solve their innate desire to save their teams from every challenging situation is as much my responsibility as it is theirs. We get comfortable with what we do best, and for many managers that means taking control. It is a quiet form of micromanagement to play the hero over and over.
“It is a quiet form of micromanagement to play the hero over and over.”
More importantly, it's a sign that even our most valued performers can be a vulnerability—and that kind of self-awareness, however humbling, is where the opportunity to scale truly begins.
More importantly, it's a sign that even our most valued performers can be a vulnerability—and that kind of self-awareness, however humbling, is where the opportunity to scale truly begins.
More importantly, it's a sign that even our most valued performers can be a vulnerability—and that kind of self-awareness, however humbling, is where the opportunity to scale truly begins.
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© 2025 Planhat AB
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© 2025 Planhat AB
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© 2025 Planhat AB
Customers
© 2025 Planhat AB