A friend recently asked me to send them the link to my blog post about having effective skip levels, and to my dismay, even though I talk about skip levels all the time, I hadn't ever actually put my thoughts into a blog post!! I'd only incorporated aspects of thinking through offsites as subsections of posts. So, here's your guide to effective skip levels.

First off, what is a skip level?! A skip level is exactly what it sounds like... a conversation with the people who report to the people who report to you.

Now, here are some common sentiments about skip levels:

• I barely have time for 1:1s, how am I supposed to fit skip levels in?
• It's super weird for me to talk to people when I don't have a lot of interaction with them.
• Meeting with my skip levels undermine the folks who report to me in the eyes of my skip levels.
• My direct reports are uncomfortable with me having skip level conversations.

I've always found skip levels incredibly helpful and effective so I want to give you some ideas and tips on how to introduce them, how to structure them, and some new ideas if you don't have time to really chat with everyone.

How to introduce skip levels

Skip levels often get this bad reputation for being systems to "check in" on a manager or try to catch individuals in some work issue, but this isn't (and shouldn't!) be what they are used for. Skip levels are used to get information about what's working well and what isn't, about what messages or company priorities are understood by folks and what isn't, to help spot gaps within the system, and to further support individuals.

When I roll out skip levels to managers, I let them know that this is a way for me to get to know individuals as people, understand what they're working on, as well as what they think is going well and what they'd love to see improved more broadly. A key detail here is that I tell managers to please give me a sense of what they're talking about to their individuals (either for improvement needs or growth opportunities) so that I can be on the same page. The last thing I want is to go into a skip level and accidentally give someone signals that they're either doing well where they aren't, or provide advice, ideas, or opportunities that are contradictory to where their manager is trying to encourage them towards.

When I roll out skip levels to individuals, much of the messaging is the same... that these are casual conversations to get to know them, hear more about their perspective on their team or the department or company, and understand what they think is awesome and what they're feeling "meh" about. It's also an opportunity for them to get to know me, so they can also feel free to bring anything that's on their mind that they want to discuss further.

The most important part of this is that there truly can't be any immediate negative consequences to someone sharing something in these skip levels. A large part of these conversations is about building trust with both your direct reports and the folks that report to them, so if you hear something that feels concerning or worth looking into further (and you will), make sure to think about how to handle that in a way that doesn't destroy the trust you're attempting to build or maintain.

How to structure skip levels

Usually, my goal is to meet with everyone, individually, once per quarter for 30 minutes (see below if you have a larger department or if once per quarter is just not feasible for you). I'll schedule a handful per week every month and that usually gets me through a good number of folks without it feeling like it pulls too much from my calendar.

I keep these conversations pretty casual HOWEVER I always have a structure for them. We don't need to keep to the structure... much like a regular 1:1, you'll have some folks who come with an agenda and full list of items they want to discuss, and others who will say "things are good" and if you don't have a bit more of a structure, you'll be tempted to end the conversation early or continue it in a way that likely feels awkward and painful for both of you.

My broad questions are:

• What's on your mind? (always start with just a broad opening. This gives people who came prepared and ready the opportunity to jump right into their agenda, and for others, it gives them a chance to share if there is anything they're thinking about)
• What kinds of things are you seeing or working on that's making you happy or feeling positive right now?
• What kinds of things are you seeing or working on that are feeling frustrating or unclear?
• Anything you want to see more of from me or in the department as a whole?

From here, there are always a few "variable" questions I throw in based on what's going on that month.

• I posted about X in the last couple of weeks, did you have any questions about that? OR How did that land for you?

This question is really helpful if I or the company rolled out a new policy, process, or idea in the last couple of weeks. Sometimes I get "oh, I didn't see that. Can you remind me what you're talking about?" From there, sometimes I'll then reinforce with managers the need to share important messages directly with their teams, or it will give me the chance to ask something like: Was the channel I posted in ok? which channel or what method would you have seen it in?

• I've been noticing X, I'm curious if you've noticed it too/if you have any thoughts about that?

This is helpful for information collecting... when I'm starting to see a pattern or trend and I'm curious how it's affecting people.

• I saw X metric change recently. From your perspective, how are you feeling about X?

There are various tools that I use to track and measure developer sentiment and productivity. Sometimes these conversations are after a larger engagement survey, other times after a pulse survey, or a developer satisfaction survey where I'm noticing numbers that have gone up or down. This is my chance to not get the "well I think people might feel," but to really get just from them and their individual perspective how they interpreted a question or how they're feeling about something.

Alternate ideas to 1:1 skip level conversations

Individual skip levels on a regular basis only scales so far. If you have a larger department, you need alternate approaches to keep in touch at this level with folks. It's often the first thing to go or to be cut from the calendar, which leads to issues down the road. So here are a few recommendations for what you can do instead.

1. Small group skip levels: Instead of 1:1 skip levels, you could maintain the same structure of the conversation, but have them with groups of 5-8 individuals. This allows you to hear similar perspectives and ideas around the questions you would ask individually, but with a larger group, covering more people in each occurrence. Something to keep in mind with this approach: you have to be really careful with group dynamics. Don't do small groups of people who all have the same manager, be aware of power dynamics if you have folks who are new to their careers with folks at a much more experienced level, etc. And understand how those dynamics may change how the conversation flows (or doesn't).

2. Office hours: Offer optional, but regular office hours (often monthly) where the agenda discussed is whatever topics people bring to discuss. This gives people a way to proactively bring their thoughts and ideas to you, providing them with that same outlet. I also have periodically posted something like "in this office hours, I'm really curious to hear about X, so if you have a perspective on that or thoughts, please try to attend." These aren't recorded to allow for freer conversation and they can be a great way to understand what is on people's minds or get information on something. A couple of things to keep in mind with this approach: first, you'll get a lot of people who don't have anything specific they want to talk about but want to hear what other people say or ask about. In this scenario, you risk having one individual regularly dominate the conversation, or everyone coming for that reason and no one really having anything they actively want to discuss. Second, it is up to YOU to make office hours compelling and fun. You want people to want to attend office hours. When there's lots of silence or it feels awkward, people start avoiding attending office hours, and then it's just 30 minutes of wasted time on your and their calendar, so always have a couple of fun topics, stories, ideas, etc. to pivot to so people keep coming back whether there's something "spicy" going on or not.

3. Department-wide retrospectives: Quarterly, you can run a longer department-wide retrospective. This gives people a structured way to discuss and address things they're loving and things that are concerning to them. Some critical things to think about when going down this path, that make this option a more challenging one: you're only hearing about these issues once in the quarter, which can lead to people waiting until this retro happens, as opposed to you or others proactively putting improvements or solutions in place. Additionally, you should allot enough time to really get into some of these issues, meaning these sessions will likely be 90-120 minutes to allow for adequate time. Finally, speaking from my experience as a facilitator, you need to have a plan to make sure this conversation effectively gets thoughts and ideas out into the open, while keeping it productive and proactive, and making sure everyone remains engaged for that amount of time. This is hard to do with a large department so it takes time to plan and be really thoughtful and intentional about it.

Additionally, I recommend to always try to do skip levels with a handful of individuals. Pick maybe 15 people to try to meet with quarterly. And RESIST THE URGE to make this group just any of your more experienced/higher level folks who are in that skip level layer. If you're only talking to those folks, you'll get a skewed sense of how things are going. Within that mix, pick a few people that are often vocal about changes, people who report to a variety of managers, gender diversity so you're getting broader perspectives, and some who are newer in their career and/or to the company and some who are more tenured.

Quick tips

• Don't take skip level conversations as 100% truth. We know that we catch people on certain days and times. Sometimes they're in a good mood, sometimes not. Sometimes their manager has just had a difficult conversation with them, other times they just got a promotion. Anything that someone tells you in a skip level should be noted, but then, make sure you're checking that information with others or keeping an eye on it. You can also follow up with them in a subsequent skip level, something like "last time you mentioned X, are you still feeling that way?"
• Expect it to take a little while for people to warm up. Your title, no matter what it is, makes you scarier for people. Plus, who knows what you'll DO with the information. They don't want to get anyone in trouble (or maybe they do, but they're not sure if talking to you will backfire) and they don't want to be seen as a tattle-tale or fear retaliation of any sort. Plus do you actually know what they do day-to-day? How could someone at your level know or remember what it's like to operate daily like they do? And there's always baggage from other roles in the past where skip levels either didn't happen, didn't happen consistently, or were weaponized in unproductive ways. So keep all this in mind, don't give up, keep your structure, and remember that it'll take a few skip levels to really get people to start talking to you about things.
• Once it feels like there's a lull, space them out a bit or mix them up. There will be a point when people are comfortable coming to you outside of skip level times. When, if there's really an issue or a question they have, they'll just ask it in a department meeting, chat app channel, or a DM. When this happens, don't just drop skip levels, because you don't want to start them up when something is wrong or not going well, but you can, at that point, space them out a bit or change the format to maximize your calendar and time.
• Take notes! You'll have skip levels less often than 1:1s so you'll want to make sure you're taking some notes so you remember what you talked about last time before going into the next conversation.

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Trying to figure out how to make skip level or other meetings more effective and productive? Book a free consultation call with me today. I'll help you talk through what actions will lead to the outcomes you're looking for.