Episode 297 Transcript:

 You know that moment when you find out your boss had coffee with your direct report and you didn’t know about it? It’s not a good moment. These situations can do a lot of damage, although we might think, wait, what’s the issue? Isn’t it a good thing that we can talk freely to anyone and kind of operate in a flat or flat-ish hierarchy. Well, let’s talk about it. These types of meetings between an employee and the manager above their direct manager are called skip level meetings. These conversations can be incredibly valuable. They give leaders real information about how work actually happens. They make leadership feel accessible instead of remote or distant, but handled poorly. They become a masterclass in how to accidentally destroy trust and make your organization more political basically overnight.

Now in preparation for this episode, I reached out to 14 HR leaders to ask for their perspective on skip levels, the good and the bad, and the best practices, and and I’m aggregating these tips and consolidating them with my own experience to share with you truly why we’re having them, why we shouldn’t have them, what to look out for and how to best.

Prepare as a leader holding skip levels with your. Employees two levels down in the org, so to speak, or vice versa. If you are being invited by a more senior leader to join skip level meetings, that is what this episode is about. So stay tuned until the very end so that with your skip levels, you know how to make them as useful as possible and reap all the benefits while avoiding the pitfalls.

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So let’s start with why these skip levels even exist because if you are going to do them, you should know what problem you are solving. The first reason is unfiltered exposure to what’s going on in the day-to-day execution. When you are a few levels up, information gets smoothed out on its way up. This is natural. Things get filtered out, watered down. People summarize, they frame things in a certain way. Sometimes they protect you from details that they don’t think matter or details that make them look bad.

So skip levels let you hear directly from the people doing the work, or at least closer to the work about what’s actually working and what’s harder than it should be. Second, they help you spot patterns early. One person having a bad week. It is kind of just noise, but when three people in different parts of the org mention the same process being slow or the same tool being broken or the same kind of work, burning people out, that’s a signal.

So skip levels give you, as the leader a way to pick up on those patterns before they become full-blown, let’s say retention problems or quality issues. Third, they make leadership visible and human. So a lot of organizations, especially organizations that have grown quickly or are larger senior leaders can feel pretty distant, and most people only see them in all hands meetings or sort of carefully staged town halls. Skip levels are a chance to have an actual conversation, right? It reminds people that leaders are paying attention and that they care about more than just the numbers on the dashboard.

Four. They surface talent. They’re always people in the organization who are doing great work but aren’t loud about it, or whose manager hasn’t figured out really how to showcase their work yet. Their visibility isn’t quite there, but the talent is present. So skip levels give you a window into. Strength and capabilities that don’t always show up in a usual reporting structure.

And that’s really important for you as a leader’s decision making and as you’re assessing the talent and the potential on your team or in your department. So those are the key reasons to do them. They give you better information, earlier signals, stronger relationships, and a clearer picture of your talent.

Now that said, none of those benefits are guaranteed just you put skip levels on the calendar, you have to run them well, and that’s where many organizations or individual leaders

struggle and actually don’t get the most out of these meetings. So let’s look at some best practices here.

Imagine you are in a skip level meeting. You got 30 or maybe 45 minutes even with someone at A level or two down. What should you actually talk about. The most effective skip levels focus on systems, opportunities, and friction. You want to understand where handoffs breakdown, where decisions get stuck, where priorities feel unclear. You probably also want to hear about tools or text that doesn’t work the way that people need it to work, or processes that add steps without adding a value.

You probably also wanna know how to problem solve from someone who is really close to the problem. You wanna hear their innovative solutions, creative ideas, opportunities that may not be visible to you. So that is all the stuff that many leaders don’t see at the top, but really creates a drag every single day for the people doing the work.

And they have answers. They have solutions, but they don’t have a channel to share that with senior leadership, with people who could really make decisions that impact and influence how the work gets done or what type of work is being done. And so that is a huge benefit of skip levels,

but again, the conversations need to actually be focused on this. Now, you may also want to talk about execution and alignment. Are goals landing the way that you think they’re landing? When a priority gets set at the top.

Does it make sense by the time it reaches a team, right, it’s gone now through some, like multiple steps of translation. You translate it to your direct report and then they translate it to their direct report. Has there been a drift between sort of what leadership thinks is happening or what they think the message is?

What’s actually being received on the ground? There are a few layers down. And is that also what’s actually happening? Right. So that is, um, the alignment and execution. Morale and workload are also worth paying attention to. You are not trying to become a therapist in those sessions, right? But you do want to pick up on signals if people are burning out that the capacity is stretched too thin, or that something might soon be breaking under pressure.

These things show up in skip levels long before that they show up in the attrition data. So information in skip levels can really give you a head start to address problems, or at least to have this in the back of your mind of like, Hmm, there’s something I need to start paying attention to that if you didn’t have to skip level, you might be ignoring and any sort of future reference that you would get.

Might just not register based on all the information that’s coming your way. Your brain is constantly filtering out what’s relevant and what isn’t, and without someone, an employee, let’s say, having planned that a seed for you, even if at that point it’s not clear what you wanna do with it, but them just planting a seed for you to remember it.

Down the road will make you have, pay more attention to it, and therefore you’ll be better prepared and more proactive to address problems. Now if you are doing skip levels with multiple people, on a regular basis, start tracking the themes, so. As usual, it’s about how systematic you are. Don’t rely on your memory only either.

Ask if it can be recorded or transcribed so you have sort of AI helping you with all that. Or take good notes and save those notes in a systematic way. If you start to notice that, let’s say people are repeatedly mentioning unrealistic timelines or compensation structures that don’t make sense or that the vision isn’t clear, or that incentives create wrong behavior, when you hear the same thing from different people in different contexts, that’s usually pointing at something structural and you need to address.

Now another thing to pay attention to for an effective skip level is to ask for practical suggestions. So it’s not just blue sky thinking, not just big ideas and raising problems. But it’s also about talking and discussing what would make the work easier, faster, safer, higher quality, more profitable, new ideas, right?

Untapped opportunities to innovate or have more reach or cut costs. And you might be surprised how often answers are small and actionable and people act would love to get your sign off and then take ownership and those little things can add up and actually have pretty significant impact over time. In addition, two people also feeling more empowered and getting a greater sense of ownership because they realize that they can actually, through the communication, through the buy-in from leadership, they can make things better

a quick side note on the psychology of this contribution is a key factor psychologically speaking, in employee motivation. When we feel we are being valued and we can contribute, we are so much more engaged and motivated. Okay, so all that can happen within the skip level and effective skip levels focus on exactly those things.

Now here is what great Skip levels don’t focus on. They don’t become open forums for complaints about individual coworkers unless collecting feedback on people. That maybe the direct manager or someone else is actually the purpose of the skip level meeting. And if that’s the case, by the way, that purpose should be really clearly stated that you are there to collect feedback.

Now I am gonna say something later about feedback if someone brings it up. Nevertheless, even if it’s not the purpose on how to address that. But moving on for now. Great. Skip levels also don’t turn into venting sessions. And the best way to prevent that is from setting really clear intentions in the beginning it must be clear to everyone involved that you’re there to learn, not to collect gossip or become the escalation path for minor frustrations.

And so with that in mind, some of like, here’s what not to do. Let’s talk more about how skip levels go wrong, because there are some very predictable ways to mess this up. Again, such a useful tool to incorporate into a leadership system,

yet if done wrong, this can quickly backfire. So the first failure mode is the open forum trap, right? You schedule a skip level, but you don’t set any boundaries on what they are for. So it becomes whatever people want it to be.

Some people may actually walk into it thinking this is a mentor mentee kind of meeting and they’re gonna show up. Or you feel, wait a second, am I the therapist? I don’t know what this is all about and what I should do with it. Some people use it to air grievances about their manager to vent and. This happens because you likely, as a leader didn’t set guardrails.

So then you end up with a lot of noise and probably very little signal. Also likely not a whole lot of action items. Now, actually worse people may start to think that skip levels are the place to complain and are sort of the avenue to, uh, raise problems up the chain.

And with that, the benefits of skip levels are out the door. So this is really something to watch out for. The second failure mode is teaching people that escalation is faster through a skip level than up the chain of commands, so to speak.

This can happen when a leader reacts in the moment. So let’s say someone mentions a problem in a skip level and the leader immediately makes a change or sends an email or pulls someone into the meeting because they feel like a, my job is to help. I am here to remove barriers. I have an answer, I have a solution.

Let’s just take care of that. And it likely comes from really good intentions of wanting to solve something and then feeling the reward of that. And so yes, it may feel like you’re being responsive and you’re doing what a leader should be doing, but what you’ve actually just taught everyone is that going to the senior leader gets results faster than working with their actual manager.

So now we’ve created an incentive to skip the chain every time something’s hard. And with that, you probably already see how the house of cards is gonna start to fall, when that is the belief employees have

now the third point of failure is if manager trust starts to erode. , So let’s say you are a frontline manager and you find out from your team or worse from your boss that decisions were made or feedback was given during a skip level.

You weren’t in the loop, you didn’t have context, and likely you feel undermined even if the senior leader yet again had good intentions. The result is that managers will stop trusting the process, and when managers don’t trust skip level meetings, the organization starts to get more political. Not less.

They’re going to start to manage up instead of managing their work, they’re going to start to be concerned of what information is shared with whom when, because they can no longer trust the transparency with the skip levels. Stuff feels to happen behind closed doors behind their back when they’re in fact supposed to be taking full ownership.

Of their team members and their work and when we wanna take full ownership, but we feel we are being sidestepped and not included. Suddenly, many leaders, if not most leaders, will start to become protective. That is never useful in organizations.

The next trap I wanna call out is the frequency trap. Skip levels can feel really good to leaders. And there might be an inclination to say like, Hey, I had some great meetings.

I learned something new when I was visiting this office and I met with the skip levels. I should do more. Skip levels. And then maybe you ask around and other people, other managers would say like, yeah, I meet with my skip levels once a month or every quarter.

And so in, in the beginning, this may all sound good, but when they happen too often, it may start to blur the lines of ownership and authority. The manager loses accountability in the process. The employee will likely get confused about. Who they’re actually reporting to because they meet with both people and they can bring sort of bigger career conversations or problems and ideas that are beyond just sort of the day-to-day task.

They can bring those to either of them, so to their direct manager, or to the senior leader, let’s say. That’s you. And naturally we would all go to the more senior leader because we wanna have visibility with them, they have more authority. We need to get their buy-in more so than our manager.

’cause if senior leader buys into it, then the manager kind of has to buy into it as well. Now the lines get blurred, and suddenly you’ve got an organization where nobody’s really clear on who owns what or what are the proper communication channels?

Now, the fifth failure mode is triangulation. This is when skip levels become a way to pass feedback about someone that the employee actually hasn’t addressed directly. So if someone complains to a senior leader about a manager.

Let’s say they’re direct manager and instead of having those conversations directly. The employees will use the skip level as a way to route around the conflict. This is triangulation in it’s poison. It breaks trust, and it creates drama, and it teaches people that the way to handle difficult conversations is to avoid them and to escalate sideways in a way or above them and let someone else more senior provide the feedback or deal with the issue.

So it’s really important that if you are, as a senior leader trying to collect feedback and you are using a skip level to do this, that the purpose is clearly stated. Hey, I would like to check in on how things are going on the team with your coworkers, with your manager.

Your manager, the person in between will know that these skip levels happen. That’s like doing a 360 review. We all know that feedback is being shared upwards and however incorporated into, let’s say, a performance review that needs to be clear and needs to be transparent, not behind someone’s back.

Especially if there’s already conflict and tension. That’s like putting oil on fire if you go behind someone’s back trying to get feedback without letting them know. Now what if you clearly define the purpose of the skip level and expectations, and you go into it as a senior leader, and then the employee starts to say, Hey,

one other thing that I wanted to share with you is some feedback about my manager. I’m having a really hard time. They don’t listen to me. They are not available. Um, I feel like I am cons getting pushback the list goes on, what happens then?

And typically to avoid triangulation in this situation, sort of that triangle, approach. The first part would be to coach that person to have a conversation with their direct manager first. You speak with them directly or how much do they already know that that’s an issue for you? Why haven’t you shared that with them?

How could you share it with them? Let’s walk through an approach. What are you afraid of? Let’s make a plan. So I know you’re gonna speak with them directly and we can then touch base afterwards and figure out a plan. Prepare them and support them in having that conversation. But it’s important for them to learn That feedback needs to be sent directly. Now, maybe they’ve already given that feedback or maybe they’re truly and for good reasons, fear some kind of retaliation. Now, that will be then on you as the senior leader.

To maybe probe and ask a few clarifying questions. Then take that into account and then decide is this something where HR needs to get involved? Is this something where you are not sure if this is actually a pattern or sort of an individual issue and you need to have conversations with other people?

Is this something that you need to bring to the manager right away and sit them down and talk about it directly and how to be sensitive about this? A lot of emotional intelligence is required to read the situation, pay attention to how everyone might feel about what’s being shared and said, and then choose the right approach.

There isn’t really okay here. Here’s one way that you always do this. That’s not the point that would be irresponsible for anyone who suggests, who doesn’t know the context and the people involved. But in 99% of the cases, the message from the leader should mostly be around. This is feedback directly to your manager. This is something that your manager

needs to hear from you directly so that it can actually be addressed between the people who are involved and creating a a challenging situation.

Okay? We now talked about five different traps that we wanna avoid when we have skip level meetings. In order to do this well and to avoid those traps, we need to be intentional, we need structure, and you have to have boundaries so that everyone involved understands what the purpose is and what it isn’t.

okay, as I promise I’m gonna get this even more practical. There are three different groups of people who need a, almost like a playbook for how to handle skip level as well. There’s the senior leader, there’s the manager, and then there’s the employee. Let’s go through each one, and we’re gonna start with sort of the senior leaders playbook here.

If you are the senior leader running skip levels, your job starts before the meeting even happens, right? You need to set intention and boundaries in advance, be really clear about what the meeting is for and what it is not for are you trying to understand execution challenges? Are you looking for sort of moral signals?

Are you trying to get a sense of how strategy is landing? Tell people if you have a clear purpose, don’t make them guess. Second, tell managers first before you schedule a skip level. Let the manager know this is happening. Share the format, explain why you’re doing it. Take the mystery out of it. The worst thing you could do is surprise a manager by having a conversation with their team without any heads up.

That quickly creates paranoia and mistrust. Then when you are in the meeting, you know, start off asking business first questions. Like you’re not there to be a friend or a confidant necessarily. You’re really there to learn about how the business is running, unless, again, there’s a very specific reason why that wouldn’t be the case.

But most often you are there to learn how the business is running, so you’re gonna focus on systems, patterns, opportunities, friction, all of that. You listen for themes more so than sort of one off issues. If one person mentions the problems, that’s interesting, right? But that’s another pattern. If three people mention it now, it turns into a pattern.

So bear in mind not to overreact to individual stories or individual problems or issues, but really take a step back and start to collect the themes. And with that, we don’t wanna make instant changes or make decisions that would bypass the chain.

If someone tells you about a problem and you immediately fix it, or send an email, make a decision, you’ve again, just taught everyone that the fastest way to get something done is to skip their manager and come to you. So route the action through the manager and you can say something like, Hey,

I’m going to talk to your manager about it, and they’ll be in touch with you to figure out the right next step That keeps the chain intact and it reinforces that manager’s authority and ownership. Now. Lastly, after the meeting, close the loop fast. So after you are done around the skip levels, share the themes. Either with that, the skips or with your manager, and discuss next steps.

Don’t let it be a black box where people talk to you and then nothing happens. So tell them what you’ve heard and what you’re going to do about it and who is responsible. That builds credibility and it choice that the time people spent with you actually mattered, that you actually listen and it keeps reinforcing the purpose of those skip levels in the future.

So that was the senior leaders playbook. Now, let’s talk about the manager’s playbook. If you are a manager and your boss is doing the skip levels with your team, your job is to normalize them and to protect trust. So normalizing skip levels means to highlight that message.

Look, this is about support. This is not surveillance. When you introduce the idea or the plan to your team, really frame it as a way for leadership to understand the work better and hear directly from the people doing it. Don’t make it sound like you’re being checked up upon or that they’re being checked upon.

Don’t make it sound like they should be careful about what they say. She’s treat it as a normal part of how the organization operates and highlight the benefits. Second,

make sure there are clear guardrails and there’s clarity in place of the purpose. If your boss hasn’t told you what the skip levels are for ask, get clarity on the format, the frequency, and what will be done with the information. The more transparency the process is, the less room there is for paranoia.

And then third, avoid being surprised. Now this doesn’t mean you need a detailed readout of every conversation, but you should have a light sort of debrief mechanism or prep mechanism that preserves trust. So either leading into if, if there is like a week where your mentor is flying in, or just plans to have most of the skip levels really talk through your employees and say.

Help your employees prepare for the skip levels? If they have questions, what can I say? What should I not say? What’s the best way to prepare for it? They likely don’t have a lot of exposure to that senior leader, so that 30 minute slot that they have, it, the senior leader matters a lot. The senior leaders going to, in their mind, sort of form a picture of their capability and their competence.

Based on that 30 minute conversation. So hopefully they take that seriously. You wanna reinforce like, this is an opportunity. Be prepared, think through what you wanna talk about and encourage them to be open, to be vulnerable. And if there’s any questions or anything that they need to know, then prepare for it.

And then after the skip level, you can ask your boss for a quick summary of themes. Not verbatim quotes or who said what? Just patterns and takeaways, and that way you’re in the loop and you can course correct if something comes up that you weren’t aware of. And then fourth, use the themes for your coaching, right?

So don’t try to figure out who said what and then defend yourself. Use it. Data, use it as information for your next conversations with your team to see what are the issues that are mentioning what’s going on, what isn’t going well, how can we get better?

This is not about protecting an ego. Okay. And then the third person in all of this is the employee. And so let’s talk about how if you were an employee and you’re being asked to participate in a skip level, how you can make the most of that time. First show up with business value, not a list of complaints, right? The goal is not to vent.

The goal is to help senior leaders understand how the work is going and where the friction is. So you wanna think about what you can teach them that they probably don’t see from where they sit or what you can share with them. Information, um, processes, opportunities.

Maybe it’s a tool that doesn’t work the way it should. Maybe it is misalignment between what leadership says is important and what act actually gets prioritized. That’s the kind of insight that’s useful.

Second, I also suggest to bring one specific insight. So try, don’t try to cover everything really. Pick one thing that would make a big difference if changed and be concrete. Say where you observe the problem, where it shows up, what it costs and time or quality or morale, and one suggestion you’d offer to improve it.

Specific beats vague every single time. Of course you can add more topics as well. But for that one thing you want them to walk away with. This one thing being really specific. Third, keep your manager in the loop as well. So if skip levels aren’t a stand part of how your organization works, give your manager a heads up about what you plan to talk about.

Like, again, you don’t need to script it out, but you also don’t want your manager to be blind spots blindsided, especially if you were the one who initiated it. If you think, Hey, I’d like to have a skip level, we never have those. And you reach out to your manager’s manager. Don’t do that without your manager knowing about it.

So you talk to your manager first, say, Hey, I would like to speak with them, and here is why. Ideally you didn’t also CC them in the email that you send to the senior leader so that senior leader sees that no one’s getting blindsided and you keep them in the loop

if something sensitive comes up that you weren’t planning to discuss. Mention it to your manager afterward. That builds trust and it keeps the relationship intact. And finally, we talked about triangulation earlier, but if you ask the employee, have feedback about your manager, that feedback belongs with your manager, not with their boss.

Unless you’ve already explored all different options and likely HR will be involved at that point, if it’s sensitive issues that involve harassment or ethics, hR should definitely be your first contact.

Skip levels are not the place to go around difficult conversations or difficult people. They’re really intended to be a place to talk about work, to build trust and relationships, and to share information.

Skip levels when done well. Reinforce leadership, clarity, trust, and execution. They give you better information to make leadership more accessible, that help you spot problems early, but they don’t replace the chain of leadership, they supplement it. The key here is really to be intentional, and with that I mean clear boundaries on what the scape levels are for and what they’re not for.

Make sure that the managers are in the loop and not on their mind to teach employees how to prepare, so they bring insight, not just complaints, and route all action and ownership through the right people in the chain so that you’re building accountability and you’re not teaching. Other people to bypass people who are actually, responsible and have oversight over a team.

If you are running skip levels right now, pick one improvement. Maybe it’s clarifying the purpose. Maybe it’s setting clear guard rails. Maybe it’s training your team on how to prepare. Just pick one thing and make it better. I recently heard a leader say. That, the only time he accepts a skip level invitation, so he doesn’t have recurring skip levels, but he would accept them.

If someone sends an invitation, is if that person confirms that they’re going to teach them something in a meeting that the leader doesn’t yet know. So that is the pre requirement that that leader sets. And he says, I don’t wanna be there talking about things that are not meaningful.

And I already know, just for us to have some face time, if I take the time out of my day to meet with a skip level, I’m gonna learn something new. So the skip level has to know that and be prepared to deliver on that agreement.

Now my final word here on skip levels before we wrap is cadence. I often hear leaders say that they would like to have quarterly skip levels.

And while that sounds great and supportive, that can quickly turn into a lot of time spent on skip levels. If you have 10 or 20 people, maybe that’s doable, but if you have more than that, quarterly, skip levels are time consuming. So yes, you could set a cadence and say, I do it annually or bi-annually.

But you could also say, I will have skip levels and meet with every person at least once a year. But it depends on whom I’m meeting, when maybe they’re different priorities or different teams. Some skip level meetings get prioritized in Q1, just based on what’s going on with that team right now or the work that they’re doing versus others.

You might not have a reason right now to talk to them, so you’re gonna move that back to Q4, and so you’re spreading all your skip levels out over the course of a year. Now for other leaders who say like. I don’t even see the reason for that. I’m going to do skip levels only when there is a need, when I feel like something’s not quite working.

When there is sort of a transition in management or in leadership when there is a big project that needs a bit more support or the senior leader to be closer to the work, and that’s when they leverage the. My personal opinion isn’t that there is a right or a wrong in terms of the cadence and how you plan it.

As long as you’re being intentional. The purpose is clearly stated and everyone knows that you’re accessible and that everyone knows what to expect, and they know how you think about skip levels and why you might meet with them or not meet with them in any given quarter or year.

I hope this was helpful and really made you think about how you approach skip levels or how you prepare for the skip loves that you might have with your senior leaders. You’re taking at least one thing from this conversation that you’re going to implement.

If you believe this was a useful episode, please share it along with either your team, with your manager, with your coworkers, peers, managers, in the organization. That helps us increase our reach and help more managers.

And if you listen to this on a podcast app, also know we have a YouTube channel where you can watch this episode on video. So check that out in the show notes.

Thanks so much and I’ll see you next week with another episode of the Managed Track podcast. Bye for now.

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