Skip Level Meeting Guide for Leaders | Hacker News Reader

Skip Level Meeting Guide for Leaders

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138 pointswomitt56 comments

I dislike that skip levels are positioned as some sort of variation of a 1:1, as other than the # of people they have nothing in common. The 1:1 is for the employee while skip levels are all about the senior manager. We already have enough opportunities for them to set the agenda and drive the conversation. A real 1:1 is a frank conversation about early-stage (potentially bad) things and based on mutual trust and vulnerability; this is impossible with the power dynamic in a skip level.

>> when it comes to individual contributors, who are a two level skip for me, ... I do a skip level group meeting with three to six people.

and this isn't even a 1:1. I can't imagine you get any sort of honest or actionable feedback in this sort of forum. There's a mismatch between the tool and the operator.

> mutual trust and vulnerability

Depending on your manager and organization, this is definitely not mutual. Managers have power over their reports, even if it is as subtle as being able to influence the decisions of more senior management over who should be promoted, retained, demoted, or fired.

If you have a bunch of cogs working, sure. But if you have a dynamic team that has the courage to point things out to senior leaders it can be a good way to pull back the veil on what’s really going on.

I'm curious what "dynamic" means in this context to you.

People actively working and interested in making the product and business better. Not just “doing time” at work.

This is an extremely delicate issue in any large organization. Skipping one level basically means: "Let's see what important things my report is not telling me". If you are asked for such a meeting, anything you say could be used against your direct manager. You need to know the office politics well before speaking anything that could have even small impact on anything. I saw people freaking out for mentioning minute stuff "behind their backs."

With a small team, it's very different - but usually the hierarchical structure is much more horizontally aligned so this is not much of a problem.

I must have worked at organizations with flatter structure than the others here. Talking with your skip level manager is an ordinary thing, if he has some opinions on the things you are responsible for why would he talk to your manager and not just go directly to you? Managers are mostly for bookkeeping purposes anyway, they shouldn't tell you what to do on a daily basis. At least they didn't in the 3 places I worked.

I had a skip-level yesterday as the Senior Manager talking to a group of 8 IC's in my org.

They brought critical feedback to me about an initiative we as a group are working on. They brought actionable ideas and they communicated them to me in a professional and sincere way.

We worked together to identify their areas of concern to make sure I understood them and I communicated that I would bring these up and work to see if we could adjust with that in mind.

2 hours later, I had my regular weekly 1:1 with a manager involved and presented those proposals. I asked them what could work as proposed and what needed work. Most were accepted, not because I mandated them, but because this is real feedback. Some we are working to get more clarity on and figure out if we can change anything.

Not all of my skip levels are this fruitful but trust and vulnerability come from creating psychological safety. I thanked the group for being a part of making that happen.

----

I also have a rule in my skip levels that if you are uncomfortable raising in the group setting there are two options:

- We can talk privately - You can ask me prior to the meeting to raise the point in the room

The second has never been used yet, but I keep it open if someone feels like they are not comfortable speaking out, but want to discuss something in a group that could be challenging.

Your skip level manager is not any more able to fire you than your manager, so I see no reason why you'd have to be more careful in those meetings than the 1:1 with your manager. I'd even say that if you aren't getting to meet and make an impression on your skip level then there is something wrong. They are your best bet to get promoted and if the organization tries to block that path for you then why should you stay instead of looking for better opportunities?

>I see no reason why you'd have to be more careful in those meetings than the 1:1 with your manager

The first thing that comes to mind is you wouldn't want to tell your skip level manager anything that you wouldn't (or haven't already) told your direct manager. That's going outside the chain of command and creates political and organizational issues that no one will appreciate.

If you're telling your skip level something that you haven't or wouldn't tell your direct manager, that is an indication that you are failing to communicate with your direct manager. That in itself is worth the skip level person knowing.

For this is less about being careful, and more about not going off on a spontaneous rant, which honestly, isn't a good idea to do for the chain of command anyway. Spontaneous rants are for your peers. Deliberate communication up and down the COF.

My two cents anyway.

> That's going outside the chain of command and creates political and organizational issues that no one will appreciate.

I'd refuse to work anywhere that cares about chain of command. Managers are for bookkeeping purposes, not commanding. If your manager doesn't let you talk to the people you need to talk to to get things done then it is a very toxic environment.

I agree with this, and disagree with the parent comment's framing of this as "going outside the chain of command", but I do think that if you have a healthy relationship and open communication with your direct manager, I can't think of many reasons not to tell your direct manager something before telling your skip-level (or above), as a courtesy and an opportunity for them to address the issue first but not because of some rigid expectations around "command structure".

Of course this isn't a hard rule, if I'm having a conversation with my skip-level and some topic happens to come up that I haven't spoken with my manager about before, I'm not necessarily going to hold back just because of that, I can follow up with my manager later. But if something's bothering me or I have some feedback or something like that, I'd generally chat with my manager about it before anyone above them.

This is half true. When I was an employee I viewed the chain of command as existing for my benefit, not my manager's. If some random bigwig wanted me to do something for them I would direct them to my manager. It wasn't my job to arbitrate between differing management demands on my time.

Know who butters your bread.

I always did whatever the higher power wanted. It served me well.

Managers aren't for bookkeeping or commanding; they're for leadership.

> Your skip level manager is not any more able to fire you than your manager

True, but say something that reflects negatively on your manager, and if they hear about it, they may rapidly become _more likely_ to fire you than the skip-level manager.

Why would you say something (whether it's negative or not) to your skip that you haven't said to your direct manager? Skip-level meetings should be about distilling important topics from your 1:1's with your direct manager and sharing with your skip what they need to know. There shouldn't really be any information that your skip has that your manager hasn't gotten weeks earlier (if it's negative, so they can try to fix it).

Not all of your work has to involve your direct manager. Some of it might come from the skip or higher, either because it’s super-secret or to give you more visibility.

In that case you still need healthy communication with your own team manager, but you wouldn’t be telling them everything except what they need to know to manage your workload.

> Your skip level manager is not any more able to fire you than your manager

Not in my experience. For my manager to fire me I need to be first put on an improvement plan. Skip manager can waive this and fire me on the spot, risking a potential lawsuit for the company.

> A real 1:1 is a frank conversation about early-stage (potentially bad) things and based on mutual trust and vulnerability; this is impossible with the power dynamic in a skip level.

This is true but I do think you’re over-dramatizing it a little. It’s also a good time to be positive (remind them what you do around here) or just talk. Which is important when everyone is working from home!

I would see that kind of group thing as more about building some rapport in a less scary environment than a skip level so that they feel if something was up they can come to you.

> this is impossible with the power dynamic in a skip level.

That is emphatically not true in the general case. It certainly isn't for me with my senior leadership.

The dynamic exists in all relationshps regardless of (and even still in) your specific interpersonal dealings.

I would love to have a skip level meeting going 2 levels up. My one on ones with my manager have become repetitive because he asks me what my problems/concerns are, I tell him variations the same 3 or 4 things every time, and has asks me for ideas about what he/we can do to try to solve them from below since he doesn't have the direct power or influence to address them from above. Unfortunately I know who his manager is and I know that my/our concerns are not going to be addressed by that person.

Talk to your manager about that meta problem. It may be awkward but you should push them to become a more effective manager, which they can do by pushing on their manager and skips.

I didn't intend for this to become an outlet for me to complain about the organizational problems at my employer. They were having leadership difficulties before the pandemic, which halted all growth and even shrinking of existing business. I think my manager is doing his best but that the organization is going to let the team atrophy and be absorbed by another, or at some point down the line when there's more money available reconstitute it. I'm leaving because that's what I see as the most likely future, people who disagree with me are staying and I am wishing them the best and washing my hands.

> My one on ones with my manager have become repetitive

My 1:1s with my boss are basically useless and I think we're both aware of that.

What do people generally talk about in 1:1s?

I've never really been clear what the purpose is other than to check a box and say it happened.

1. Opportunities for timely feedback (in both directions)

2. Concerns/issues

3. General chat

Most people forget the third option. It’s OK if it’s just time to hang out with each other.

That said, it’s your meeting more than it is your manager’s. If you want to cancel, you should. However, frequent cancellation is a signal of a problem to my mind.

As a manager, the only thing more frustrating than a 1:1 which is like pulling teeth, is a 1:1 with somebody who doesn’t want to communicate at all.

Except in unusual circumstances, I normally find that #1 and #2 don't change much on the one or two week cadence that 1:1s usually happen. Every couple months there might be a significant amount of time spent on one of these, and then there might be a few check-ins on that afterwards, but in most cases it's not anywhere near enough time to fill a 30 minute slot every 2 weeks.

I also at some point personally started making a conscious effort to spend less time on #2, bringing up concerns/issues. Nine times out of ten nothing will come out of it anyway (most things are out of your manager's control), and nobody likes a complainer. Your effort is better spent practicing meditation, or else applying to new jobs if things are really bad, rather than spending half an hour every week "voicing concerns" in a 1:1.

That basically leaves a large majority of 1:1 time spent on #3, which I totally agree with the parent comment gets awkward after a while.

I have started wonder if the 1:1 in tech is an "emperor has no clothes" type of situation. Am I so unusual? Or do we all just go along pretending that these are super essential to a functional team, while in practice not much really ever comes of them?

I think what gets lost is that it's your 1:1, not the manager's. Same when you go to a skip level.

If they are the one driving the agenda it is indeed probably going to be a waste of time.

This cartoon is a useful prompter for different things to think about going into them:

https://twitter.com/b0rk/status/1037186572234498048?lang=en

So looking at that list,

We have group meetings to cover the majority of:

- What's going well

- What's not going well

- Team priorities

- Brainstorm

My boss in general doesn't really give feedback.

And the answers "Ask for opportunities", "Career Planning", and "Ask for extra resources" is basically, "This is the job, if you want something else, go find a new job"

I did manage to get a raise and a few extra responsibilities by going out and getting a job offer at a different company.

I think probably the real answer is that my job is a dead end and probably an unhealthy environment to have spent so much time in.

But also I have outstanding work-life balance, which is my highest priority at the moment with three young kids at home.

In a couple years maybe that changes.

My old manager had "optional" 1:1 meetings that were decent enough provided folks above him didn't schedule over them.

We would talk about projects I am working on, their general status and if I have blockers, if the team is working good from my POV, administrative stuff like PTO, performance reviews. He also had varying interests so there was some personality there such as what game you playing, what shows you watching. We even shared a bit of "how things at the homefront".

We were both in our late 20s/early 30s and he was relatively new. He didn't want "that manager" because lord know that company had a lot of managers that existed to attend meetings and divy work up with nothing of benefit to the team.

But, I can echo what you are saying. I have had manager that hold meetings just to dodge work and claim they did some managering that day. Yea, daily 2 hour "team lunches and planning sessions" doesn't do anything for the fact we need to get work done boss.

Have you requested a meeting? You might be surprised.

No, the upper level person in question is overbooked with being in charge of 1/3 or 1/2 of the company's employees. My personal opinion is that person was given too much responsibility too quickly and is in over their head. When my team came into their purview they told us they wanted to spend as little time as possible on my team, and I've deferred to that statement.

> When my team came into their purview they told us they wanted to spend as little time as possible on my team, and I've deferred to that statement.

That sounds like a pretty effective way of hurting morale.

I've seen this before, and generally think it tends to be because technical people who have risen to the top as the org grows don't like giving up power, so they end up holding control over way too many teams/depts and the org suffers for it. (or it's a naive cost saving measure)

I would like to see a comparison of org-charts in highly functioning corps of varying size.

to my outsider ears, this sounds exactly like the sort of situation where you should request a meeting and highlight the issue. Not in a finger point-y way, but as an observation that your team needs more time from someone at their level

1:1 meetings are just as important in my opinion as an open door policy. Yea, you are my boss's boss and have a lot more reports, you probably get pulled in a lot more directions than I as an IC. I understand why, as teams and companies grow, things get more distanced. Even Linus over at LTT laments that his new hires never get the same 1:1 time his earlier employees had.

But, the topics talked about need to have action take on them. Unless you just don't have any power at all, which I can believe. Quarter after quarter at my old company we would mention that the tasks and direction our org were taking weren't the best, would lead to problems, and that we weren't staffed nor compensated individually enough for the new work and responsibilities being loaded onto us. It fell on deaf ears and when I left we had already had almost a full team leave. Shoot, the whole reason I got that job is because they needed folks so bad they took someone not entirely skilled in that area to pick up the slack. The cycle just kept repeating and here it is, MONTHs later, and I hear the same thing.

Suppose grindhouses are good for cutting your teeth at least.

Everytime I have been invited to a 1 on 1 with someone high up the org ladder, I have been given talking points from the people in between

When I was a jr. engineer, I had a skip level meeting with the director of our department (~30 people). I asked the director -- in the snarky way that certain entitled junior employees have -- what he actually did in his job. He laughed and explained that his job was to make sure senior management understood what we were doing and were onboard with why we were doing it. Nobody gave me any talking points and I was too green to worry about the political ramifications of my snark... and there weren't any. It was just a half hour opportunity to talk to someone I didn't usually get a chance to talk to. I now realize that this company, or maybe just that department, was a particularly healthy place to work.

It's not that snarky.

Especially from someone new to the field these are questions I would be expecting, especially at a tech company (so pretty equalitarian and meritocratic where the director probably started as an engineer himself). I would also expect the career path to take to get into management to be discussed as well.

It depends how it's said. I would hesitate to correct the person who actually said it about whether they said it in a snarky way unless I was actually there.

Sure, maybe the tone was.

But the question itself doesn't strike me as such, at least coming from a junior engineer.

Someone more senior should know what the tasks of someone at that level are, so asking "what is your job" might be interpreted as implying he isn't doing much.

This depends entirely on org culture. I've worked at places where I had to go thru an absolute gauntlet of "prep" meetings to hone my talking points for talking with someone several skip levels above my manager.

And, I've worked in places where you are free to send a DM to the C-Suite if you feel like it's necessary to get your work done. No pre-approval required.

I say this with privilege, but you need to be asking why. And if you are dissatisfied with the answers, you are working with the wrong place. As you can see from other comments here, skip levels serve many purposes. If in your case it's because skip levels are used to bypass distrust of your manager, then you need your manager to address that with you honestly before you simply do what they say.

Does anybody have advice on how to make the most of meetings with coworkers/mentors 2+ levels up the ladder from yourself? I once had a great session with a c-suite exec in an employer with 5 digits worth of employees, but I think that was as much due to his being a really motivated mentor as any prep or questions I did. I want to make sure I'm prepared for future meetings if the mentor is not as open or enthusiastic about mentorship.

Think about purpose and benefit. A cynical view, perhaps, but the way to a good relationship is to make it part of the transaction.

What are this person's priorities (outcomes they need to make happen) for the year? How can you help make that happen?

Come to the conversation with "you're doing X; how can I help make that happen?" - and when you explain why you want to help, make it personal ("I want to get to Y, and this will help me get there"). You help with X, and they'll hep with Y.

I'm more than happy to take cynical views, I find they're often what I would consider just realistic.

That's a great breakdown and it makes total sense. I've found people respond well when you already know stuff about them. Do you think it would be even better to come in with something like this? "I know you want to achieve X this year, and I have an idea Y or a personal goal Z to help us get there. What do you think?" Or do you think that would be getting too ahead of things?

You want them to be a sponsor of your work to others. At that level of seniority they could really make a difference in your promotion and growth over time if they know who you are and what problems you're solving.

Mentorship should be about someone telling you what they did when they were in your shoes, and coaching is more like performance optimization.

This comment is gold. Even with some jobs and plenty of effort to learn career skills behind me, I feel like I'm only just starting to appreciate the value of someone higher up being a sponsor of your work. Thanks for really singling that out and explaining how it matters.

Your second point is also really insightful. That distinction is also something I've recently begun to really realize, and your wording cuts right to the point. Thanks for your advice!

As a follow up, in your experience, what kind of stuff has been received especially well by higher-ups?

Ask them what the top 3 problems they are spending time on. That will uncover areas for you to invest in understanding to uncover solutions.

People at this level are looking for help from people that are doing the real work in the organization who have a better understanding of the details. Conversely, this level has a wider view of problems that have high impact across the organization. Seek to uncover those problems and find solutions.

That's super helpful, I'll definitely make sure to do that. As a follow-up, if the mentor were way higher up the ladder than you, how would you translate the really high-level goals they see to goals that are actionable to your level? I've had a couple meetings that went along these lines, and I was a bit unsure how to take their executive/c-suite perspective into something I could work on as an individual contributor

I've found that the most useful discussions I've had are around how the people up the ladder think about the junior persons area/projects and how it fits into the bigger picture.

The junior person knows more about the details and the senior person should understand more about the strategy so both have a chance to learn from each other and to each walk away with a better overall perspective.

As a skip level manager myself it's also seems like a better use of everyones time than me answering generic questions.

That's helpful as it gives me a sense of how I can also try to bring value to the meeting. What kind of questions have you found useful/practical from these meetings? I always want to be careful not to ask something that comes off too basic or uninformed.

My number one advice would be to actually listen to what the underlings have to say and keep the groups small. I have been to two of these lately and each time the VPs held long monologues that were only interrupted by some people who tried to suck up to the manger by loudly agreeing. The rest was just sitting around and said nothing.

If you aren’t willing to receive negative feedback about your own role maybe you shouldn’t do these meetings.

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