How are my managers really doing?
What’s really happening in my organization?
What do my people really think?
Am I missing anything important?
Whether you’re a veteran leader or brand new to having real hierarchy below you, these kinds of questions are likely to be on your mind often.
The more removed from the day-to-day work you are, the harder it is to have a feel for what’s happening and how people are really doing.
Skip level meetings are one of the best ways to keep a pulse on things and gather insights you couldn’t get any other way.
Skip level meetings are one on ones where you– whether you’re a manager or the CEO– sit down with the direct reports of all your managers (see above).
Today, we break down everything you need to know about meeting with your skip level team members to answer key questions you may have like:
- Are skip level meetings a good fit for you?
- How do you start skip level meetings?
- How do you make the most of your skip level 1 on 1s?
Let’s dive in.
Everything You Need to Know About Skip Level Meetings
As you rise in an organization, your challenges change:
- First, as an individual contributor, your job is to do your work to the best of your ability to help the team and company.
- Then, as a manager, your job is to get the best performance from your team. You’re now a multiplier.
- When you manage other managers, you need to develop leaders under you, and look out for the macro behaviors & culture across your department. Your efforts are now exponential.
Becoming a manager requires a totally new mindset, and the jump to managing managers has many significant challenges of its own:
- You were an okay manager, are you ready to teach others how to be a good manager?
- You don’t know everything that’s happening all the time anymore. Can you make good decisions with partial information?
- The demands on your time (and meeting requests) have never been higher. Are you investing your time wisely for the short and long term?
- Dozens, or maybe even hundreds, of people are looking up to you. Are you setting a good example?
It can certainly feel daunting. The can-do, take-on-any-project attitude that may have made you a great individual contributor is impossible at this level. You have to be careful with your time, and deliberate in your approaches.
Skip level meetings improve your communication architecture
Throughout all these challenges, information needs to be flowing up and down your organization. It’s why Ben Horowitz wrote about how critical this is all the way up to executives, and especially the CEO:
How you and the leaders that report to you communicate with their teams is essential to everyone’s success. One on one meetings are a key part of this as Horowitz continues from the above excerpt in The Hard Thing About Hard Things:
Skip level one on ones go beyond meeting with your managers and give you a way of improving the communication architecture of your entire team by meeting with their direct reports.
Are skip level meetings a good fit for you?
A wise man once said, “If you want to know what’s important to someone, look at what they choose to spend time on.”
How do you spend your time as a leader?
Skip level meetings are all about improving communication and the flow of information. If you find yourself trying to accomplish any of the following, then you will get a lot of value out of skip level 1 on 1 meetings:
- Find out how your managers are really doing beyond what they tell you.
- Get feedback and insights to help your managers, and their teams, improve.
- Get a pulse on what’s happening on the front lines you’re layers removed from.
- Build trust with those lower in your organization so they stay engaged and contributing.
- Learn where there is dysfunction, insufficient communication, or confusion within parts of your organization.
- Personally demonstrate you value everyone in your organization in a scalable way.
With just a few hours of your time each week, you can get insights from people you rarely get to interact with otherwise.
Greater than the sum of its parts.
Even better, when you consider the sum of everything you hear, patterns will emerge that help you understand more of what’s happening across teams and your organization as a whole.
This helps you make better decisions, catch problems with a manager before it leads to turnover, and strengthen relationships with everyone in your organization.
With all these potential benefits for you to be an effective leader, it’s no surprise those that have them swear by them.
Having a relationship with your skip level team members is profoundly powerful. One manager we spoke to even went as far as saying:
“I’m comfortable stating that not having skip level 1 on 1s is abdicating your responsibility as someone who manages a manager.”
How to start skip level meetings
So you’ve bought into the idea of having these meetings, but how do you start them?
There’s a number of steps to take to make them a success:
- Tell your managers – to avoid surprises or concerns about what will be a net positive for them.
- Tell your skip level team members – so they know why you are meeting with them and what to expect.
- Schedule them in a manageable way – there are still only 24 hours in a day, so you need to be deliberate in scheduling them at the right frequency, and not miss anyone.
Let’s break each one down.
1) Tell your managers
If you just started having skip level meetings without telling your managers, they’d probably wonder what was going on. Don’t do that.
Instead, explain to them why you’re doing them and address any of their concerns.
If you have a 1 on 1 with them soon, talking about it there is a great way to have time to answer their questions. It also has the bonus of allowing you to convey your genuine, positive body language as you share your goals of doing them.
It’s all in how you frame it.
It would be easy for a manager to feel undermined by skip level meetings if they thought it was just to check up on them. That’s why you need to frame it as a net positive and clearly state your true intentions.
Writing or saying something like this can frame skip levels as a win for everyone:
And here’s a text version you can copy, paste, and adapt to fit your personality:
I wanted to let you know I’m starting something new. Occasionally, I will do skip-level 1 on 1 meetings with your team members to get a pulse on strategy, build relationships, and understand your team members’ perspectives.
From these conversations, you may hear new feedback or questions from your team members. That’s healthy and to be expected. I’ll also share any patterns or common feedback I hear that’s relevant to you.
Most importantly, these meetings are to help everyone in our organization work more effectively. I am not going behind your back to second-guess your work nor undermine your leadership.
Let’s plan to discuss this more in our next 1 on 1 together.”
With the right expectations set and a little trust from your managers, they’ll buy into what you’re doing.
2) Tell your skip level team members
If you haven’t built a relationship with many of your skip level team members, they may be surprised or concerned about you wanting to meet with them. They may wonder if they’re in trouble or did something wrong.
That’s why going into the meeting you should set their expectations, too. Writing or saying something like this can help them come into your first skip level 1 on 1 with a positive outlook and knowing exactly what to expect:
And here’s a text version you can copy, paste, and adapt to fit your personality:
I’m starting something called skip level 1 on 1s with you and your peers. It’s a chance for us to meet, get to know each other, and talk about what’s working and not in our organization.
The goal is to help us all work better together, and ensure you’re happy and successful working here.
I’ll bring a few questions for you, and if there’s anything you’d really like to discuss, we’ll start with that. Ideas for improving your team, observations you think I should know about, and feedback on your manager are all good topics. I’m also happy to answer any questions you have for me.
Our first skip level 1 on 1 will be on <DATE & TIME>. I look forward to talking with you then!”
When you set expectations, it removes the risk of people having the wrong idea coming into them. Then, you’re much more likely to start the first skip level 1 on 1 meeting off on the right foot with everyone.
3) Schedule them in a manageable way.
The challenge with any plans for skip level 1 on 1s is how quickly the number of meetings you need to have can grow. It’s easy to suddenly realize you have 20, 30, 60, even 100 people you could meet with.
While it can feel daunting, breaking it down into bite-size pieces is how you can make it all possible. Here’s what to do:
- Make regular time: Take a look at your calendar and ask yourself how many hours a week you can devote to these.
- Example: You set aside 3 hours a week for skip level meetings
- Divide by your number of skip levels: Divide the number of skip level team members you have by your number of hours you’ve committed to in step 1. This is how many weeks it will take to get to everyone before starting the cycle again.
- Example: With 60 skip level team members, it would take 20 weeks to meet with everyone once.
- Start scheduling recurring meetings: Get them on your calendar so the time doesn’t get filled with other commitments, and so that you & your skip level team members can prepare.
- Example: Cushioning for time off, holidays, and unavoidable conflicts that means meeting with everyone once every 6 months (26 weeks)
By making the weekly commitment, you can slowly chip away at even large teams, and build a healthy rhythm.
While the meetings will be with different people each week, you’ll get used to having them as part of your workweek. This is the key to making skip level meetings a successful habit for you.
Is this really possible?
Yes. With a little planning and a commitment to meeting, you can keep in touch with even large teams. Most leaders we’ve spoken to meet with their teams of 40-50 people quarterly. At companies like Netflix, some leaders even manage to have skip levels annually with over 300 reports.
Maybe your team of 25 isn’t so bad after all? :)
How often is too often?
If you’ve recently risen to the rank of managing managers, you may not have that many skip level reports. When there’s only a dozen or so of them, it can be tempting to meet with them almost as often as your weekly 1 on 1s with your team.
However, you need to avoid having them that often. They’re a great tool, but the primary means of communication should be Individual Contributor (IC) -> Manager -> You. Your skip level meetings skip that middle step.
This is why one of the key things to ask in a skip level meeting is, “Have you talked to your manager about this?” to reinforce and encourage good communication between IC and manager.
You can have too much of a good thing in this case. If you rely on skip level meetings too much, you’re sending mixed signals to the manager of that team.
Of course, your skip level team members want to speak to you. And yes, they are going to share the most relevant interesting bits because you are The Boss. Though too much skip leveling can ultimately degrade confidence in what should be the primary means of communication: IC -> Manager -> You.
If you tell your managers and team members what to expect and make it a habit to have some every week, you’ll be well on your way to great skip level meetings.
Now, let’s look at how to make the most of them once you’re in the meeting.
How do you make the most of your skip level 1 on 1s?
Walt Disney may be referring to his Oscar-winning cartoons above, but it also applies to you and your team members you have skip level 1 on 1s with.
Done well, you’ll help build a healthy organization they love working for and will tell their friends about. They’ll also start to look forward to their skip level meetings with you.
Here’s how to make the most of your skip level 1 on 1s:
1. Remember what’s at stake.
These meetings are about the health of your organization. People leave managers, not companies, so if you don’t build a relationship with everyone, you can lose large parts of your department because of a bad manager.
Too often, people have the mindset, “If I had a problem with my boss here, I’d probably just leave the company.” This happens when they feel they have no avenue to address problems with their manager.
While there are many things to discuss in your skip level 1 on 1 meetings, this is one of the biggest. This default mindset to give up if you have a bad manager only changes if you do something about it.
2. Start with rapport
A little rapport goes a long way. Think about how much easier conversations are with strangers you meet once you find you share a hometown, common interest, kids the same age, past city you lived in, etc. The same applies at work.
Your first skip level 1 on 1 can be a little awkward, so take some time to build rapport with them. If you can find out some things about them from their manager, all the better, but the key is to demonstrate you care about them as an individual. Everyone has a few things they care about most, and they appreciate you taking a few minutes to ask about them.
Not sure where to start? Worried an age difference could make this hard? The right question or conversation starter can help immediately start building rapport and move the conversation forward. For example, try and find out if you both:
- Grew up in the same city/state/abroad or went to the same high school or college
- Have a big or small family
- The same hobby or passion
- Like the same sport, or even better, back the same team
- Have the same taste in TV shows, movies, books, or podcasts
Or specifically, try questions like:
- What made you decide to join our company?
- What motivates you to come to work each day?
- Where did you grow up? Where did you go to college? (if you don’t have much information, questions like this are great to help you probe for things you have in common)
- What’s your favorite book you’ve read / podcast you’ve listened to / movie you saw recently?
- What made you decide to become a(n) [engineer/marketer/sales person/customer success/role]?
Want more ideas on how to build rapport? Here are 81 ideas for building rapport with anyone.
3. Get feedback and ideas
One of the most important parts of building great skip level relationships is trust. If you have built rapport and trust with them, then they’ll be much more likely to come to you with problems and ideas.
The ideas and feedback they provide can help you in a variety of powerful ways:
- Fix problems when they’re small: Catching an issue while a skip level perceives it is much less expensive than when it boils over to reach you 2 layers higher in your organization.
- Retain your teams: As mentioned earlier, without an avenue to give feedback on their manager, many people will just leave. Getting feedback on their manager is a great way to help the manager improve and avoid costly turnover.
- Get ideas for improvement: Your skip level team members have a very different vantage point than you do. They can provide valuable ideas and feedback on initiatives you’re unlikely to think of yourself.
You have to ask for it.
The key is you have to ask. A general request like, “Do you have any feedback on your manager?” is much less likely to get results than asking more directed questions like: (Hat tip to Cate Huston for the manager questions below)
- What’s one thing we could improve based on how <last major project they were on> went?
- What’s the best part of working with <their manager>?
- What’s the hardest part of working with <their manager>?
- What do you wish <their manager> would do more of?
- What do you wish <their manager> would do less of?
- Can you tell me about a time you needed your manager’s support to accomplish your goals, and what happened there?”
The more specific the better. Specific questions help them more easily think of something valuable.
Even better, if you ask a group of skip level team members the same specific question, you can spot patterns to identify what to prioritize of what you hear. A broad, generic question won’t do that.
More skip level meeting questions
Here are some more ideas for great skip level one on one questions to gain feedback:
- When was the last time you had a conversation with your manager about your career? How did it go?
- Are you happy with your career progress here? Why/why not?
- How does your manager handle questions when you ask for help?
- What is a recent situation you wish your manager handled differently?
- If you were in charge of the team you work on, what’s one thing you would do differently? Why?
For more great skip level meeting questions, check out 47 Skip Level Meeting Questions to Improve Your Managers and Engage Your Employees and One on One Meeting Questions Great Managers Ask Their Teams.
Meanwhile, if you’re looking for more ideas on feedback, you can learn about fresh approaches like feed forwards and 5-word reviews here. Also, make sure you build the habits to help you get more feedback here.
4. Praise them
Praise costs you nothing and has massive value. If word gets all the way to you that someone is crushing it, tell them! Nothing will put a smile on someone’s face faster than some genuine, specific praise from a leader in their organization.
If you don’t know which of your skip level team members are your stars, then start asking.
Ask people in their skip level 1 on 1s, “who on your team is doing great work?” or “who do you enjoy working with most?” And follow up by asking why and for specific examples. This makes it easy for you to relay the good news to the great people you want to keep.
Remember: Giving praise has a profound impact on a company’s bottom line, and their retention:
“[Those answering “strongly agree to] “In the last seven days, I have received recognition or praise for doing good work” is responsible for a 10% to 20% difference in revenue and productivity.
Employees who report that they’re not adequately recognized at work are three times more likely to say they’ll quit in the next year.”
Set the example you’re an organization that values its people by making praise a part of your skip level 1 on 1s.
5. Anything burning on their mind
Especially when you start these meetings, you’ll need to have questions ready to break the ice and build trust. Over time though, many of your skip level team members will start to feel comfortable bringing things up themselves.
While you may have a number of topics you’d like to cover, don’t let that block them from talking about what’s burning on their mind. As Andy Grove knows above, you want to be sure you hear out anything bothering the team member.
Sometimes these issues are things they’ll immediately put on the agenda, or open up at the start if you ask, “what’s on your mind?” or “what should we talk about today/” Other times you need to watch out for the Zinger as described by Andy Grove in High Output Management:
“…be wary of the “zinger,” which is a heart-to-heart issue brought up at an awkward time…the subordinate might tell you something like he’s unhappy and has been looking outside for a job and give you only five minutes to deal with it.“
Regardless of how or when it comes up, use your skills of listening and observation to look for when a team member has a lot to say about something. These kinds of insights are exactly why you have these meetings and can save you from major problems later like turnover and dying projects.
6. Take notes
It’s a simple act, but it means so much. When they tell you something and you demonstrate you care enough to make a note, it shows you value their input. Also, as Grove astutely reminds us, it implies that what they said could lead to change or action.
Taking notes builds confidence that it’s a worthwhile effort to bring things up with you. You should already know this from your 1 on 1s with your team, or start doing it there, too.
7. Follow up and follow through
If you made it to the level of leading other managers, this should be pretty obvious, but it’s worth reinforcing. These meetings will not be valuable conversations for long if people feel like nothing happens after you talk. Take action.
When you determine next steps at the end of a skip level 1 on 1 meeting, they fit into 3 common categories:
- What they will do: Whether it’s sending you some information, doing their part to help address an issue, or acting on your advice, it’s important they’re owning part of the outcomes.
- What you will do: What you discuss may be about fixing problems, sharing information, or implementing good suggestions. By making it clear what you will do, you build their confidence in coming to you again later.
- To discuss with their manager: A big part of a good skip level 1 on 1 is getting feedback directly or indirectly about their manager. Making it clear you will address their concerns can help with especially critical moments when a manager is doing poorly and the team is considering quitting.
Bonus: “Have you talked to your manager about this?”
There will be times where you hear things that are better dealt with by their manager. Or, you may want to know what their manager has or has not already done about it.
That’s why it’s so powerful to ask your skip level team member, “Have you talked to your manager about this?”
Their answer reveals all kinds of valuable insights; maybe they hadn’t thought to, the manager took a surprising action, or maybe they were afraid to.
You want them to know they can come to you, but also that their manager should be their first call. If they’re not, that’s worth understanding why and addressing.
Then, you can coach their manager on either building more trust or helping them behind the scenes to address the issue. This gets you working from both sides to get them talking more. That’s great coaching.
Want help organizing all these notes and action items from your skip level 1 on 1s? Lighthouse is purpose-built to help managers like you succeed, and we’ve built a feature specifically for awesome skip level 1 on 1 meetings.
You can sign up for your free trial here and mention skip levels on the signup survey to get access.
8. Don’t miss anyone
Once you start these, everyone deserves their chance to meet with you. You don’t want to miss a valued perspective, and want to avoid looking like you’re playing politics with certain people.
Especially introverts may not be forceful to get on your calendar, which is why it’s important to make sure you don’t miss anyone. Otherwise, they can feel slighted or not valued as much as others you did meet with.
Skip level meetings are a powerful investment in the health of your organization
When you break it down, a once seemingly daunting task can appear much easier. While you can’t meet with your skip level team members every week, with a little planning and preparation, you can keep in touch with everyone at least a few times a year.
The insights you gain from them will help you improve all your managers, boost retention and loyalty, and increase the overall health of your organization. What else can you do that has that much of a positive impact?
Ready to start skip level 1 on 1 meetings at your company?
Need help making the most of the ones you already have?
- Be more organized: Keep all your notes for your 1 on1s and skip level 1 on 1s in one easy to navigate place, not 500 Google docs.
- Be prepared: Always remember what happened last time no matter how long ago with prep messages, and be ready with our suggested questions to spark discussion.
- Never forget a good thought: Add notes where you already are: email, Slack, web, and mobile.
- Save time doing the right things: Automatically route action items from a skip level to the next 1 on 1 with their manager to discuss and address it.
…and much more. Sign up for your free trial now here and start building a great communication architecture in your organization.