June 9, 2025 • 13 mins
The discussion explores the challenges faced by "skip leads," or managers of managers. It emphasizes that managing managers requires distinct skills compared to overseeing individual contributors. Key points include avoiding undermining or covering for line managers, employing task-relevant maturity for effective delegation, and recognizing the significant influence skip leads have on organizational dynamics.
#management, #leadership, #skiplead, #delegation, #organizationaldynamics, #managers, #taskrelevantmaturity
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Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
Welcome to Bite-sized L&D, your quick no-nonsense update on the latest in workplace learning.
(00:10):
Today, we're uncovering the secrets of the skip lead and how mastering this role can
revolutionise your management style. Plus, we'll share innovative strategies like the API
Endpoint experiment to empower your managerial journey. All right, let's get straight into it.
All right, everybody. Welcome to another deep dive here on L&D Bites. I'm Donna,
(00:34):
and as always, I've got my co-host, Jakov, here with me. Today, we're tackling something that
I think is going to hit close to home for a lot of our listeners, especially those of you climbing
that management ladder. Hey, everyone. Yeah, Donna's right about this one hitting close to home.
So here's a question for you. Have you ever heard someone complain about their manager?
(00:56):
Maybe they're micromanaging, or they lack product sense, or they're just not supportive enough?
Oh, absolutely. I feel like that's practically a workplace universal experience. We've all been
there, right? Either we've been the one venting, or we've been the shoulder someone else is crying
on about their terrible boss. Exactly. And there's that classic saying everyone loves to throw around.
(01:19):
People don't quit their jobs. They quit their managers. But here's the thing. What if we've
been looking at this problem all wrong? What if the real issue isn't actually with the direct
manager at all? Oh, interesting. Lay it on me. Where are you going with this? So there's this
concept called the skip lead. That's the manager's manager. And the argument is that pretty much every
(01:43):
manager challenge you can think of, whether it's direct or indirect, actually traces back to this
skip lead. Wait, hold up. The manager's manager? So when I'm complaining about my boss,
I should really be looking at my boss's boss. That's exactly right. Think about it this way.
The skip lead is the one who hired your manager in the first place.
(02:05):
They're the one reviewing your manager's performance, coaching them or failing to coach them.
They're setting the tone for how management works in that part of the organization.
Okay, that actually makes a lot of sense when you put it that way. It's like,
if my manager is terrible at giving feedback, maybe it's because their manager never taught
(02:26):
them how to give good feedback. Or maybe they're not holding them accountable for it.
Bingo. And here's where it gets really interesting. Most organizations completely fail to recognize
that managing managers is a fundamentally different skill set than managing individual
contributors. It's not just the same bag of tricks applied to a bigger group.
(02:47):
Right. And that leads me to think about all those newly promoted managers who suddenly
find themselves with other managers reporting to them. What makes it so different?
Well, think about what changes. When you're managing individual contributors,
you're working directly with people who have all the context because they're actually doing the work.
(03:07):
But when you're managing managers, you're now working through this abstraction layer.
You can't just walk over to the person doing the actual work and ask what's going on.
Ah, so it's like playing telephone, but with management decisions and information flow.
Exactly. And that clear division between makers and managers gets all blurry too,
(03:28):
because now you've got managers reporting to other managers. Plus, getting that unfiltered
information straight from the ground level. That's basically gone.
Makes sense. So what can these new skip leads do about it?
I'm imagining there are some practical strategies here.
There are. One of the most interesting approaches is something I like to call the API Endpoint
(03:52):
Experiment. It's basically a thought exercise where you ask yourself,
if I had zero access to any individual contributor in my organization and could only get information
through my direct report managers, how would I be effective?
Ooh, that's fascinating. It's like forcing yourself to work within constraints to figure
(04:12):
out what really matters. What kinds of questions does that bring up?
So many good ones. Like, how do I help my line managers spot problems on their teams without
talking directly to their team members? How do I help them deal with performance issues instead
of just jumping in myself? When do I defer to their judgment, even if it goes against mine,
(04:34):
and when do I insist my perspective wins out? Those are really hard questions,
especially that last one about when to override your manager's judgment.
That feels like it could go wrong in so many ways. You're absolutely right,
and that brings us to one of the most critical principles. Never undermine your direct report
managers. This is where a lot of new skip leads really mess up. How so? Well, imagine you're having
(05:00):
one of those skip level one-on-ones, you know, where you're talking directly with someone who
reports to your direct report. They bring up a problem, and your natural instinct is to jump
in with a strong opinion and solve it right there on the spot. Feels efficient, right?
Yeah, totally. You want to be helpful and show that you're engaged and that you care about
(05:20):
solving problems. But what you're actually doing is completely undermining your direct report manager.
You're robbing them of the opportunity to learn how to handle these situations. Plus,
you're potentially confusing their team member with contradictory directions.
Oh no, that's like management whiplash. The poor employee is getting different
(05:40):
messages from different levels. That sounds like a recipe for chaos.
Exactly. There's this great example from Jeff Weiner when he was CEO of LinkedIn.
He had a direct report tell him that what he thought were just casual, take it or leave.
It remarks were actually creating massive fire drills, because people were weighing his opinion
(06:01):
so heavily. Right, because when you're the skip lead, your words carry way more weight than you
might realize. So what's the better approach? Listen carefully. Ask lots of follow-up questions,
and then work with your direct report manager to do all the actual follow-up and direction setting.
You become more of a coach and advisor rather than the person making decisions on the spot.
(06:26):
That makes sense, but I imagine there's a flip side to this too. What happens when your direct
report manager is actually struggling or underperforming? Ah, you're hitting on another crucial
principle. Never cover for them. This is probably even more common than undermining,
and it's just as damaging. What does that look like in practice? Picture this. You know your line
(06:47):
manager is struggling with a project or with their team, but instead of addressing it head-on,
you quietly start doing part of their job yourself. Maybe you start pulling double duty,
taking on some of their responsibilities, and then you provide cover for their performance
when talking to your own bosses. Oh, I can see how that would feel like the
(07:08):
compassionate thing to do in the moment. You're trying to help them out and make sure the work
gets done. Right, but it's actually helping no one in the long run. The underperformance
doesn't get addressed. Your manager doesn't get the coaching and support they need to improve,
and you end up burning yourself out trying to do two jobs. Plus, if you're covering for them
(07:29):
with your own boss, then the organization doesn't have accurate information about what's actually
happening. That seems like it could lead to bigger problems down the road. Absolutely,
the better approach is to clearly report the underperformance up the chain, along with a plan
to course correct, get feedback on that plan from leadership, and then set clear performance
(07:50):
expectations with your direct report manager. Okay, so we've talked about not undermining and
not covering. What about the actual work of delegation? How do you figure out which manager
should handle which projects? This is where it gets really interesting. There's this concept
called task relevant maturity or TRM that comes from Andy Grove's classic book High Output Management.
(08:14):
I love that book, but refresh my memory on how TRM works in this context. So the idea is that
you're constantly doing matchmaking between projects and people. Every project or situation is
different. Different scope, risk, ambiguity, technical requirements, interpersonal dynamics,
and every manager is different to different skill levels, experience, emotional maturity,
(08:41):
specializations. So it's not just about who's available or who has the lightest workload.
Exactly. You're asking questions like, which of my managers has dealt with something very similar
before? Who has the right technical skills? Who's been asking to be stretched into a project like
this? Who's senior enough to handle high ambiguity? Who do I trust most with delicate
(09:04):
interpersonal situations? That sounds like it requires really knowing your people well and
being thoughtful about development opportunities too. Absolutely. And here's the key thing,
delegation doesn't mean abdication. You still need to review work on an ongoing basis
and even micromanage when necessary. The book still stops with you as the skip lead.
(09:29):
How do you balance that? Like how do you know when to check in versus when to step back?
There's actually a helpful framework for this. You can think about projects along two dimensions,
uncertainty and impact. A project that's low uncertainty and low impact. You can delegate
that to a newer manager and basically forget about it. But something that's high uncertainty and high
(09:52):
impact. That needs to go to your most capable person and you need to be reviewing it closely
and continually. That makes total sense. And I imagine those high uncertainty, high impact projects
are often the ones that involve multiple teams and cut across different managers.
You got it. Those are exactly the ones where the skip lead needs to stay really engaged because
(10:15):
inter-team communication is inherently difficult. And there are all these competing priorities
and multiple managers involved. This is all really fascinating, but I want to step back for a second.
For our listeners who might be new skip leads or aspiring to be one,
what's the most important thing they should keep in mind? I think the biggest thing is just
(10:35):
recognizing that this is genuinely a different role with a steep learning curve. It's not just
management, but bigger. The skills, the responsibilities, the way you add value. It's all fundamentally
different. And probably being patient with yourself as you learn these new skills, right?
(10:55):
Absolutely. This stuff takes years to master. Even people who've been doing it for over a decade
are still learning and refining their instincts. So for our listeners out there, the next time a
friend comes to you complaining about their manager, maybe the right question isn't,
tell me more about your boss, but rather, tell me about your manager's manager,
(11:15):
because that's probably where the real leverage for change actually lies.
I love it. This has been such an eye-opening conversation. It really shifts how you think
about organizational problems and where to focus your energy for creating change.
Right. And it also gives new skip leads a roadmap for how to think about their role differently,
(11:36):
recognize it's a new role, use thought experiments to build new mental models,
be careful about undermining or covering, and get really good at task-relevant maturity for
delegation. Perfect summary. So for all you current and aspiring skip leads out there,
maybe it's time to take a step back and really examine how you're approaching this role.
(11:57):
Are you managing managers, or are you just trying to manage a bigger group of individual
contributors? Exactly. And remember, the goal isn't to have all the answers right away.
It's to start asking the right questions and building these new muscles over time.
Couldn't agree more. Thanks for tuning in to another episode of L&D Bites, everyone. If this
(12:18):
resonated with you, maybe share it with a skip lead in your organization. They might just thank you
for it. And hey, if you find yourself in that skip lead role someday, remember what we talked about
today. Your impact on the organization goes way beyond just your direct reports.
Until next time, keep learning and keep growing. We'll catch you on the next deep dive.
(13:06):
Stay tuned for more updates.
Welcome to Bite-sized L&D, your quick no-nonsense update on the latest in workplace learning.
(00:10):
Today, we're uncovering the secrets of the skip lead and how mastering this role can
revolutionise your management style. Plus, we'll share innovative strategies like the API
Endpoint experiment to empower your managerial journey. All right, let's get straight into it.
All right, everybody. Welcome to another deep dive here on L&D Bites. I'm Donna,
(00:34):
and as always, I've got my co-host, Jakov, here with me. Today, we're tackling something that
I think is going to hit close to home for a lot of our listeners, especially those of you climbing
that management ladder. Hey, everyone. Yeah, Donna's right about this one hitting close to home.
So here's a question for you. Have you ever heard someone complain about their manager?
(00:56):
Maybe they're micromanaging, or they lack product sense, or they're just not supportive enough?
Oh, absolutely. I feel like that's practically a workplace universal experience. We've all been
there, right? Either we've been the one venting, or we've been the shoulder someone else is crying
on about their terrible boss. Exactly. And there's that classic saying everyone loves to throw around.
(01:19):
People don't quit their jobs. They quit their managers. But here's the thing. What if we've
been looking at this problem all wrong? What if the real issue isn't actually with the direct
manager at all? Oh, interesting. Lay it on me. Where are you going with this? So there's this
concept called the skip lead. That's the manager's manager. And the argument is that pretty much every
(01:43):
manager challenge you can think of, whether it's direct or indirect, actually traces back to this
skip lead. Wait, hold up. The manager's manager? So when I'm complaining about my boss,
I should really be looking at my boss's boss. That's exactly right. Think about it this way.
The skip lead is the one who hired your manager in the first place.
(02:05):
They're the one reviewing your manager's performance, coaching them or failing to coach them.
They're setting the tone for how management works in that part of the organization.
Okay, that actually makes a lot of sense when you put it that way. It's like,
if my manager is terrible at giving feedback, maybe it's because their manager never taught
(02:26):
them how to give good feedback. Or maybe they're not holding them accountable for it.
Bingo. And here's where it gets really interesting. Most organizations completely fail to recognize
that managing managers is a fundamentally different skill set than managing individual
contributors. It's not just the same bag of tricks applied to a bigger group.
(02:47):
Right. And that leads me to think about all those newly promoted managers who suddenly
find themselves with other managers reporting to them. What makes it so different?
Well, think about what changes. When you're managing individual contributors,
you're working directly with people who have all the context because they're actually doing the work.
(03:07):
But when you're managing managers, you're now working through this abstraction layer.
You can't just walk over to the person doing the actual work and ask what's going on.
Ah, so it's like playing telephone, but with management decisions and information flow.
Exactly. And that clear division between makers and managers gets all blurry too,
(03:28):
because now you've got managers reporting to other managers. Plus, getting that unfiltered
information straight from the ground level. That's basically gone.
Makes sense. So what can these new skip leads do about it?
I'm imagining there are some practical strategies here.
There are. One of the most interesting approaches is something I like to call the API Endpoint
(03:52):
Experiment. It's basically a thought exercise where you ask yourself,
if I had zero access to any individual contributor in my organization and could only get information
through my direct report managers, how would I be effective?
Ooh, that's fascinating. It's like forcing yourself to work within constraints to figure
(04:12):
out what really matters. What kinds of questions does that bring up?
So many good ones. Like, how do I help my line managers spot problems on their teams without
talking directly to their team members? How do I help them deal with performance issues instead
of just jumping in myself? When do I defer to their judgment, even if it goes against mine,
(04:34):
and when do I insist my perspective wins out? Those are really hard questions,
especially that last one about when to override your manager's judgment.
That feels like it could go wrong in so many ways. You're absolutely right,
and that brings us to one of the most critical principles. Never undermine your direct report
managers. This is where a lot of new skip leads really mess up. How so? Well, imagine you're having
(05:00):
one of those skip level one-on-ones, you know, where you're talking directly with someone who
reports to your direct report. They bring up a problem, and your natural instinct is to jump
in with a strong opinion and solve it right there on the spot. Feels efficient, right?
Yeah, totally. You want to be helpful and show that you're engaged and that you care about
(05:20):
solving problems. But what you're actually doing is completely undermining your direct report manager.
You're robbing them of the opportunity to learn how to handle these situations. Plus,
you're potentially confusing their team member with contradictory directions.
Oh no, that's like management whiplash. The poor employee is getting different
(05:40):
messages from different levels. That sounds like a recipe for chaos.
Exactly. There's this great example from Jeff Weiner when he was CEO of LinkedIn.
He had a direct report tell him that what he thought were just casual, take it or leave.
It remarks were actually creating massive fire drills, because people were weighing his opinion
(06:01):
so heavily. Right, because when you're the skip lead, your words carry way more weight than you
might realize. So what's the better approach? Listen carefully. Ask lots of follow-up questions,
and then work with your direct report manager to do all the actual follow-up and direction setting.
You become more of a coach and advisor rather than the person making decisions on the spot.
(06:26):
That makes sense, but I imagine there's a flip side to this too. What happens when your direct
report manager is actually struggling or underperforming? Ah, you're hitting on another crucial
principle. Never cover for them. This is probably even more common than undermining,
and it's just as damaging. What does that look like in practice? Picture this. You know your line
(06:47):
manager is struggling with a project or with their team, but instead of addressing it head-on,
you quietly start doing part of their job yourself. Maybe you start pulling double duty,
taking on some of their responsibilities, and then you provide cover for their performance
when talking to your own bosses. Oh, I can see how that would feel like the
(07:08):
compassionate thing to do in the moment. You're trying to help them out and make sure the work
gets done. Right, but it's actually helping no one in the long run. The underperformance
doesn't get addressed. Your manager doesn't get the coaching and support they need to improve,
and you end up burning yourself out trying to do two jobs. Plus, if you're covering for them
(07:29):
with your own boss, then the organization doesn't have accurate information about what's actually
happening. That seems like it could lead to bigger problems down the road. Absolutely,
the better approach is to clearly report the underperformance up the chain, along with a plan
to course correct, get feedback on that plan from leadership, and then set clear performance
(07:50):
expectations with your direct report manager. Okay, so we've talked about not undermining and
not covering. What about the actual work of delegation? How do you figure out which manager
should handle which projects? This is where it gets really interesting. There's this concept
called task relevant maturity or TRM that comes from Andy Grove's classic book High Output Management.
(08:14):
I love that book, but refresh my memory on how TRM works in this context. So the idea is that
you're constantly doing matchmaking between projects and people. Every project or situation is
different. Different scope, risk, ambiguity, technical requirements, interpersonal dynamics,
and every manager is different to different skill levels, experience, emotional maturity,
(08:41):
specializations. So it's not just about who's available or who has the lightest workload.
Exactly. You're asking questions like, which of my managers has dealt with something very similar
before? Who has the right technical skills? Who's been asking to be stretched into a project like
this? Who's senior enough to handle high ambiguity? Who do I trust most with delicate
(09:04):
interpersonal situations? That sounds like it requires really knowing your people well and
being thoughtful about development opportunities too. Absolutely. And here's the key thing,
delegation doesn't mean abdication. You still need to review work on an ongoing basis
and even micromanage when necessary. The book still stops with you as the skip lead.
(09:29):
How do you balance that? Like how do you know when to check in versus when to step back?
There's actually a helpful framework for this. You can think about projects along two dimensions,
uncertainty and impact. A project that's low uncertainty and low impact. You can delegate
that to a newer manager and basically forget about it. But something that's high uncertainty and high
(09:52):
impact. That needs to go to your most capable person and you need to be reviewing it closely
and continually. That makes total sense. And I imagine those high uncertainty, high impact projects
are often the ones that involve multiple teams and cut across different managers.
You got it. Those are exactly the ones where the skip lead needs to stay really engaged because
(10:15):
inter-team communication is inherently difficult. And there are all these competing priorities
and multiple managers involved. This is all really fascinating, but I want to step back for a second.
For our listeners who might be new skip leads or aspiring to be one,
what's the most important thing they should keep in mind? I think the biggest thing is just
(10:35):
recognizing that this is genuinely a different role with a steep learning curve. It's not just
management, but bigger. The skills, the responsibilities, the way you add value. It's all fundamentally
different. And probably being patient with yourself as you learn these new skills, right?
(10:55):
Absolutely. This stuff takes years to master. Even people who've been doing it for over a decade
are still learning and refining their instincts. So for our listeners out there, the next time a
friend comes to you complaining about their manager, maybe the right question isn't,
tell me more about your boss, but rather, tell me about your manager's manager,
(11:15):
because that's probably where the real leverage for change actually lies.
I love it. This has been such an eye-opening conversation. It really shifts how you think
about organizational problems and where to focus your energy for creating change.
Right. And it also gives new skip leads a roadmap for how to think about their role differently,
(11:36):
recognize it's a new role, use thought experiments to build new mental models,
be careful about undermining or covering, and get really good at task-relevant maturity for
delegation. Perfect summary. So for all you current and aspiring skip leads out there,
maybe it's time to take a step back and really examine how you're approaching this role.
(11:57):
Are you managing managers, or are you just trying to manage a bigger group of individual
contributors? Exactly. And remember, the goal isn't to have all the answers right away.
It's to start asking the right questions and building these new muscles over time.
Couldn't agree more. Thanks for tuning in to another episode of L&D Bites, everyone. If this
(12:18):
resonated with you, maybe share it with a skip lead in your organization. They might just thank you
for it. And hey, if you find yourself in that skip lead role someday, remember what we talked about
today. Your impact on the organization goes way beyond just your direct reports.
Until next time, keep learning and keep growing. We'll catch you on the next deep dive.
(13:06):
Stay tuned for more updates.
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