The Ultimate Skip Level Meeting Guide for Leaders

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The Ultimate Skip Level Meeting Guide for Leaders - Interview with Sarah Milstein & Tanisha Barnett from Mailchimp

The higher you climb in leadership, the more important skip level meetings become for you.

You have to see what’s happening on the ground floor of your organization. You have to build relationships with different people all over the company. You need feedback on how your direct reports are doing.

You need to get out there, get to know your people, and see the organization through their eyes, so you can make it all work from a leadership perspective.

This is what skip level meetings are for.

How do you do them? How do you avoid making your individual contributors anxious just by your title? What should you focus on to make skip level meetings productive?

Take a page from the playbook by Sarah Milstein, Senior Director of Engineering at Mailchimp, and Tanisha Barnett, Director of Engineering at Mailchimp. Learn how they handle all kinds of skip level meetings in different contexts, and perfect your own meetings to build better connections. This interview is from episode 33 of the Level-up Engineering podcast, hosted by Karolina Toth.

We're covering:

• Skip level meeting definition
• Organizing skip level meetings
• The reason they started doing skip level meetings
  • It came with management
  • Building connections
• Skip level one-on-one meeting and regular one-on-one comparison
• Choosing the people to schedule skip level meetings with
  • Based on report structure
  • Based on ongoing work
• Notifying the in-between manager about skip level meetings
• Skip level meetings' role at Mailchimp's engineering culture
• Using feedback about your direct reports from skip level meetings
  • Share positive feedback
  • Coach reports to give constructive feedback
  • Sometimes, take matters into your own hand
• Keeping track of the content of skip level meetings
  • Keep running notes
• Skip level meeting questions
• Reactions of employees when approached by directors and above
  • Lots of anxiety
• Icebreakers for skip level meetings
• Sensitive topics at skip level meetings
  • Avoid gossiping
  • Avoid making final decisions
• Ideal length for a skip level meeting
• Advice for new leaders on skip level meetings
• Skip level meeting stories
• Bonus advice
  • You learn about the context
  • You build your reputation
  • Make time for it

About Tanisha Barnett and Sarah Milstein

Tanisha Barnett has been at Mailchimp for almost two years, and she’s currently a Director of Engineering. Before joining Mailchimp, she’d spent a long time at Macy’s Engineering Department, steadily rising through the ranks.

Sarah Milstein is a Senior Director of Engineering at Mailchimp, where she arrived over two years ago. She is the site director at Mailchimp’s satellite office in Brooklyn. She brought a lot of leadership experience from a long history as a leader in different positions at various companies.

What is a skip level meeting? Why is it important?

Sarah: A skip level meeting is with an employee who reports to one of your direct reports. For example, Tanisha reports to me, so a meeting with one of her reports is a skip level meeting for me. A skip level one-on-one meeting means there are only these two people present.

An important reason to have skip level meetings is to familiarize yourself with the context of the work going on at different levels and departments of the company.

Tanisha: The main idea behind skip level meetings is to build relationships with the next level of the organization. When employees need to ask for help from an engineering director, or just want to have a conversation, it’s easier if there is an existing connection. Mailchimp’s engineering culture does a good job with this.

It’s a great way to learn about the things your employees care about and to understand their work. You also get feedback about their manager, your direct report, which you may not get otherwise.

What do your skip level meetings look like?

Sarah: I hold them regularly every two months. They're set on the calendar, so everyone knows they're coming. I do skip level one-on-ones with engineering managers, who report to my team of engineering directors.

When it comes to individual contributors, who are a two level skip for me, I use a different meeting format. In this case, I do a skip level group meeting with three to six people.

It’s a helpful format, because sometimes people hear each other say things that surprise them. It often helps them understand that it’s okay to give feedback, and it’s better for everyone if they share their thoughts.

I encourage employees to reach out to me for a one-on-one if there’s anything they didn’t want to talk about in the group. This happens occasionally. Taking part in a skip level group meeting helps me build a connection with them, so they trust me enough to talk to me.

What was your reason to start doing skip level meetings?

It came with management

Sarah: I’ve been doing skip level meetings in some form since I became a manager. It has evolved along the way.

Ever since I arrived at Mailchimp, I've had at least 70 people reporting to me. It’s been impossible to do skip level one-on-ones with everybody, so I’ve evolved the skip level group meeting over the past year.

Building connections

Tanisha: When I was onboarding as an engineering leader to Mailchimp, I wanted to get to know everyone to see the teams' dynamics. This is why I scheduled skip level one-on-ones with everyone I was going to work with.

I had a team of 35 people, and I scheduled meetings with them over the first couple of months. I spaced them out to make sure they all got my full attention. The initial skip level one-on-one didn’t have an agenda; it was a space for us to introduce each other and have some face time.

It helped me build connections. I still have regular skip level one-on-ones going with people that they schedule themselves.

How is your approach different in a skip level one-on-one meeting to a regular one-on-one?

Sarah: It’s different for me, because I use a standing agenda for skip level meetings. I use the same questions every time. On the other hand, regular one-on-one meetings with my direct reports are driven by what they're working on and by what they want to talk about.

Tanisha: In my case, they’re more similar. Unless there is something specific that I want to discuss, which happens more often with my direct reports, I’m open to talk about anything they want to.

My main focus for skip level one-on-ones is to let the employees connect with me. If I build an agenda for these meetings, it doesn't leave them enough space to talk about whatever they want to.

How do you pick who to have skip level meetings with?

Based on company structure

Sarah: I let the company’s structure guide me. If there is a manager with six individual contributors reporting to them, I invite those six people for skip level group meetings.

I rarely do regular double skip level one-on-ones, where the structure can get more complicated. The reason for that is because when I offer the chance for these meetings, no one shows up. I’m happy to have those meetings, but I don’t want to force it on anyone, so I keep it optional.

It may be because it’s daunting for an individual contributor to meet with a senior director of Engineering. It’s also possible that it's irrelevant to them. My work may not seem connected to theirs.

Based on ongoing work

Tanisha: I use a different approach. I have skip level meetings with the team members of my managers, but I also have matrix managers reporting to me because of their work. I do skip level meetings with their reports as well, because they may not directly report to me, but their work is tightly connected to my responsibilities.

I want them to know that there is another level of management they can come to, because what they're doing is important. I aim to make them feel like we're all one team, no matter who they report to.

Do you notify the manager before you have a skip level meeting with their reports?

Specific notifications

Tanisha: I always notify the managers. The idea is to give them a heads up that a skip level meeting is coming. It helps, because when their direct report tells them they have a meeting with me, the managers can reassure them it’s a routine meeting.

My skip level one-on-ones aren’t set in stone. Most of them are regular; they happen about once a quarter, but sometimes as much as six months pass between two meetings. It depends a lot on the time of the year.

No notifications

Sarah: I have several skip level meetings every week, and I can’t seem to find the time to notify the managers. Just today, I have a skip level one-on-one with one of Tanisha’s reports, and I didn’t notify her!

My skip level meetings are regularly recurring events, however. I have skip level one-on-ones with the engineering managers reporting to my directors every two months. Everybody’s generally aware that these meetings are happening.

Are skip level meetings part of the engineering culture at Mailchimp, or do managers choose to do them individually?

Every leader gets to choose

Tanisha: It’s not specific to Mailchimp. I’ve been doing skip level meetings as long as I’ve been a director. I don’t even think every director at Mailchimp is doing skip level meetings.

Sarah: Not everyone uses skip level meetings at Mailchimp, and not everyone has to. It depends on your work.

The two main points of the skip level meetings:

1. The leader gets more feedback about the manager in between.
2. It’s a chance for the reports to talk to a more senior leader and to build a relationship they may need eventually.

Example from Mailchimp

I don’t work with Tanisha daily, even though she reports to me. This means I’m not closely involved with her work and her team. If I were, the skip level meetings wouldn’t be necessary, because the information could spread, and the relationships may build up organically.

This is why it’s important for me to have skip level meetings with the people reporting to her. These meetings give me a better sense of her work. They also give her people the sense that they can go to another person if they need to escalate something, or if they need a different insight.

How do you use the feedback about your direct reports in skip level meetings?

Share the positives periodically

Sarah: Most of the time, people tell me good things about their managers, and I keep them in a running list. I can share that list when it comes up, for example, in quarterly check-ins. These notes are part of our conversation.

Coach reports to give constructive feedback

When I hear negative feedback about a manager, most of the time I coach the reports to give the feedback directly to their manager. I help them figure out how to have the conversation themselves, and this helps them improve the relationship with that manager.

Sometimes, take matters into your own hands

It’s not always the right approach. Sometimes I need to talk to the manager directly about how they're approaching things or how they are perceived by their reports. This rarely happens; only about one time out of ten do I think I should take on an issue.

How do you keep track of the contents of your skip level meetings?

Keep running notes

Tanisha: I keep running notes on my skip level meetings. This gives me a reference point and serves as a reminder if I want to follow up on something. Referring back to previous conversations reassures my reports that I’m paying attention to them.

It’s also a great icebreaker and reminds them where we left off.

If I’m specifically looking to discuss something, I put it on the agenda. Often there is no agenda, in which case that’s what I put into the invite. I also follow up the skip level meetings with a Slack message, like, “Thanks for touching base,” because I know it can be stressful to meet with a more senior employee.

I keep my notes for myself. I only ever share them if a follow-up requires it. Even then I may just send a quick note, "We talked about this, and I wanted to follow up. This is what I’ve found out."

Sarah: I use a similar approach. I organize it in a way that I keep a document for each of my direct reports, and I keep running notes in it with the dates and the participants of each skip level meeting. It’s structured by a set of questions for them every time, and these are always on the calendar invite.

Sometimes I get such a strong positive comment, that I want to share it with the manager. In this case, I'll copy and paste the notes from the skip level meeting into the one-on-one meeting agenda for the manager saying, "Here’s something nice your team may not have told you." Other than this, the notes are for me.

What are your regular skip level meeting questions?

Sarah: I always use the same questions.

Here’s the list:

• "What is your manager doing to support you?"

• "What do you wish they were doing?"

• "What questions do you have about the decisions they made or the way they acted?"

• "What questions do you have for me about anything in the company?"

These questions are always on the invite. People expect them and come prepared, so sometimes we get the meeting done quickly. Other times, we blow through these questions and end up going unexpectedly deep in other areas.

I use the same set of questions for both skip level one-on-one meetings and skip level group meetings.

How do people react when an engineering director approaches them for a skip level meeting?

There is plenty of anxiety

Tanisha: It tends to build anxiety when they see the invite for a skip level meeting. I don't bring an agenda partly because I don't want them to feel like they have to prepare for it. But that may also be a source of anxiety.

I try to make it clear that it's about getting to know each other, it’s for me to get a sense of what's going on, and to talk about anything they want to. I tend to ask questions like: "How are things going?" I also ask specific questions about what they're working on; it often helps to jumpstart the conversation.

I keep notes on what I've heard from every person, so I can make it easier for them to talk to me.

Sarah: One of the benefits of the group skip level meetings is that there is less anxiety. The people who have attended these meetings before help anyone new understand that it's a relaxed conversation. We often don't use up the whole time, and there's plenty of room for them to ask me questions or to discuss other things.

I’m also the site director in the Brooklyn satellite office, and I have skip level one-on-ones with every new employee. Not everybody there reports to me, but they all know me to some degree. I don’t let the titles drive the conversation, which helps them talk to me if they need something.

What do you use as an icebreaker in skip level meetings?

Tanisha: I make it a point to know something specific about each person I will have a skip level meeting with. The idea is to establish a connection. It may be about their work, or something other than work that I’ve previously heard they’re interested in.

I use what I know about the person to break the ice. It’s to make them more comfortable and relaxed, so we can have a conversation about what's going on and how I may help them.

Is there anything you avoid discussing in a skip level meeting?

Avoid making final decisions

Tanisha: Don’t avoid any topics.

Just be careful not to give a definitive answer on anything without knowing the full context. In these cases, I take all the information and let them know that I plan to follow up on it later. You have to do your research, and it’s best to start by asking some leading questions.

• “What's your concern?”

• “What call-out do you have?"

Sometimes, they don’t need you to do anything; they just want to vent. This is why you need to make sure you’re clear about their expectations and your next steps. This makes you synched and helps avoid awkward situations.

Avoid gossiping

Sarah: Even though a key reason for the meeting is to talk about the manager, I don't want to support gossiping. It's a structured meeting that we use for giving feedback, not to talk trash behind people’s backs.

When I get feedback about what employees wish their manager would do, I listen, but I try not to reinforce it in any inappropriate way. I say things like, "That sounds difficult," or "I understand why you want that," while I avoid saying, "Your manager really screwed up." I have to be careful about this.

I also try to avoid saying, "I'm going to solve this problem for you." Instead, I try to coach them to solve their problems. I involve myself if there is bullying or abuse, but most of the time, employees can solve their issues with some mentoring.

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What’s the ideal length for a skip level meeting?

Sarah: I normally schedule skip level one-on-ones for 30 minutes, unless the person lets me know that they want to specifically discuss a topic. Then I schedule extra time.

I make 45 minutes for the skip level group meetings. Sometimes they’re shorter, other times they run a bit longer. It varies a lot.

Tanisha: I do the same. I just try to leave an extra 15 minutes after each meeting. It doesn’t only give me time to get ready for the next one, but if the meeting runs longer, I still won’t be late.

What’s your advice for leaders who are new to skip level meetings?

Tanisha: Let your employees know what you're hoping to get out of it. I send out a message to all the individual contributors saying that I’m scheduling skip level one-on-ones, and what to expect at these meetings. This helps lessen the anxiety, because everybody at all levels knows it’s happening.

I have rules for myself when scheduling skip level meetings. I only schedule them from Tuesday to Thursday between 10 am and 3 pm. I try to set them up to have 15 to 20-minute breaks in between.

It takes a lot to be on point all that time, so make sure you give yourself time to put forth the effort, so you can be present for each person. I schedule my skip level meetings longer, to put guardrails around myself, to be able to put in the effort with everyone.

Sarah: My calendar isn’t organized enough for me to be able to do all this up-front. I just repeat how it goes at the beginning of every skip level meeting. Also, when it comes to skip level group meetings, I let the people who have been at these meetings before go first, so the new employees get less anxious.

Would you share a story about your skip level meetings?

Sarah: I had a first-time engineering manager, a man of color, with a group of five engineers, all women of color. After a few skip level meetings with the group, a concern came up about the manager not being aware of some of the team members’ challenges. According to them, he was generally sensitive and well-intentioned; he just missed some of their experience.

They weren't even clear on this themselves, until we were all in the room discussing it.

It was an extremely valuable conversation, and the outcome was that we all agreed that they should talk to him individually, and I should discuss it with him in a one-on-one meeting. This level of follow-up action is unusual. This was helpful for the manager as well, because we managed to show him what he was missing.

Tanisha: I’ve had a few skip level one-on-ones with some interns. At this point, they are no longer interns, but full-time employees, and we’ve kept that connection going ever since. They've always felt that I was a person they can talk to or ask questions from.

Most companies don’t provide interns with access to engineering directors or other leaders. They were so thankful for me making time to meet with them, that it had a huge impact on me. Probably a bigger impact than I had on them.

Because of this experience, going forward I’ll make sure to put new interns on my skip level one-on-one meeting rotation. Especially if they're connected to my work. It seems to be great for everyone involved.

Bonus advice for skip level meetings

You get familiar with the context

Sarah: An essential reason for doing skip level meetings is to see the context that you wouldn't see otherwise. You get even more when meeting with a person who works on a different team.

You get to learn a lot about the other parts of the organization in skip level meetings. It’s a very valuable aspect. You also get to share context with others about what you’re working on, that they wouldn't see otherwise.

Even with a structured set of questions, a lot of interesting stuff comes out.

You build your reputation

Doing skip level meetings consistently will get you a reputation for being a person employees can talk to. Once that happens, if a problem comes up, people are more likely to come to you, even if they aren’t from your group.

This is a big part of being a leader. It helps you create an atmosphere where people feel safe to raise their problems, and ask for help. Your employees can help you a lot in creating this environment.

Make time for it

Tanisha: Make time for skip level meetings. People get a chance to share information with you, and you get a chance to do the same while making connections. All leaders have busy schedules, so it's easy to ignore a complete department because it’s not your priority.

But you’ll be happy when you take the time to do it. You learn so much. It’ll also help you do your own work better, because you become familiar with the wider context.

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About the author:

Gabor Zold is a content marketer and tech writer, focusing on software development technologies and engineering management. He has extensive knowledge about engineering management-related topics and has been doing interviews with accomplished tech leaders for years. He is the audio wizard of the Level-up Engineering podcast.