A Guide for Skip Level One-On-Ones

As you climb to higher management levels and begin leading other managers, keeping in touch with your team's pulse can become difficult. Understanding what is happening at the lowest levels can help you wrap context around what your team brings you. You may also need to build stronger support for your goals and direction.  Introducing skip-level one-on-ones can be an effective way to increase your engagement and understanding with your whole team.

The most important thing you can do with your time is communicate with your team!

Manager jumping over his employees in an office.
How to start

If you are serious about strengthening your connection with your team through skip-level one-on-ones, you should start with a plan. It is critical to be clear about what you want to achieve with these conversations, or you may cause stress or conflict within your team.

Clarify Your Goals

Start by setting aside some dedicated time to consider what you want to achieve with these one-on-ones. Here are some questions to answer to help you.

  • What information are you missing from your team? How can working 1 level past your directs help get that information?
  • What are some things you can learn about the business from individual contributors on your team?
  • How can you clarify business objectives for your team?
  • What goals or objectives can you accelerate by sharing more with the next level?
  • What are some goals you can reinforce for your directs?
  • Who can you help mentor or coach?

I use skip-level conversations to keep sight of the topics the team is concerned about or struggling with. Challenges the team is excited to tackle. Answer their questions about the business. Reinforce and clarify team objectives. If requested, I offer mentorship or coaching around their interests.

Understand Your Time

Thoroughly review your calendar and schedule.  How much of your week/month do you want to dedicate to these one-on-ones? How are you going to fit these extra conversations in?  What do you need to give up to make this possible?

Once you have answered those questions, decide who and how frequently you will schedule time with. Are you going to meet with everyone? Only team members at a certain level? Only people you can mentor? Only team members working on specific projects?

Keep in mind that one-on-ones need to be regularly scheduled with enough time for you and your team members to prepare. For some extra insight, check out this one-on-one guide.

Communicate & Gather Support

Now that you have your plans and know how this will work.  There is one more critical step before you start putting invites on the calendar. It is essential that you proactively share your plan for skip-level one-on-ones with your directs. Please do not put them in a situation where they are surprised by something you shared with someone in their reporting structure. 

As part of these manager-level conversations, ensure you share your goals for the conversations and how you believe the managers can support you. Share who you plan to meet with and the frequency of your conversations and ask that these people get a heads-up before you schedule a meeting. Then, solicit feedback from your team's managers. What would they like you to commit to or avoid during skip-level one-on-ones?

An Agenda

Armed with clear goals and buy-in from your management team, it might be tempting to start chatting and see where things go. However, you must define an agenda for skip-level conversations to ensure your team and you get the most from this time. Additionally, consider sharing some of your questions with them beforehand.

Here is an example of my one-on-one agenda:

1. Their topic: I always start by listening to what is important to them and having a conversation about that topic.  I ask probing questions to understand what makes it important today. I offer direction where I can, but only after hearing them out. They should speak the most during this time.

Some questions you can ask:

    • What is on your mind today? 
    • What has been frustrating? 
    • What are you excited about?

2. Something I'm Curious About: A fantastic way to build strong, trusting relationships with your team is to make opportunities for them to be experts and teach you something.  I try to bring something I want to learn in every one-on-one. They should speak the most during this time.

Some ideas for you: 

    • How is their direct manager supporting them? 
    • How is their project tracking? 
    • What technical aspect do you want to understand better?
    • What process can they offer advice about?

3. Topics They are Curious About: Since messages often get distilled or muddied as they work through the organization, take some time to clarify things they are unclear about. If they have nothing, share something others have asked you about. You will probably speak the most during this time, but leave room for them to expand on their question.

Some questions to get started: 

    • What is something that doesn't make sense to you?
    • Is there a topic that I can help explain?
    • What are you curious about?
    • What have you been worried about?

4. My Goals: I like to close out each one-on-one by reiterating or clarifying a goal I have for the team. Do your best to make this a two-way conversation about the goals.

Some lead-in ideas: 

    • I've been talking to everyone about a goal I have...
    • How do you feel we are progressing on ...?
    • What would help us make more progress on ...?
    • Tell me what you think about our goal of ...

Here's one more agenda idea:  If this is your first skip-level one-on-one with someone, start by explaining your goals for the conversation. This will help them feel comfortable sharing with you.

Also, consider taking some time to share about your background and hobbies. People tend to appreciate understanding how you got to your position, and it helps them understand how and why you make decisions.

Here is an example of how I start a first skip level:

Since this is the first time we’ve had a one-on-one, and I know these can be a little weird, let's start by chatting about how these work and what you can expect. First, I want you to consider this your time to share things with me. If you ever feel like you don’t have something to discuss or there is a pressing priority, just let me know.  We can always reschedule or cancel. You are not wasting my time either way. Next, I will not get upset by anything you share with me, so please be honest, and I’ll do the same for you.  I may want to discuss things with your manager after we chat, but it will be raised as something I’m concerned about, not something you brought up. Finally, I’m not going to share anything that I haven’t already talked to your manager about, and there may be things that come up that I’m not prepared to discuss.  In those cases, I’ll just let you know that I’m unable to answer. What do you think?

Things to Keep in Mind

There are a handful of other key things to be aware of around skip-level conversations.

Be Consistent

Always share a consistent message/direction/strategy with everyone you talk to. It is a bad look to appear to change your opinion based on who you are talking to. For example, if you agree on a direction with one person, do not change that direction when talking to the next person. Always be consistent in describing the team’s objectives and outcomes, and do not purposefully or inadvertently give two people or groups conflicting directions.

Do Not Surprise Anyone

You and your team's managers should share a consistent message. You should avoid sharing something that conflicts with what their direct manager is saying. It is critical to refrain from sharing news, feedback, or assigning tasks during a skip-level discussion you have not previously discussed with their direct manager.

Also, follow up with their direct manager to share anything they need to follow up on or provide support after your skip-level conversation. Don’t let these things wait until their manager finds out from someone other than you. 

Do Not Waste Time

The last thing we need is more time preparing for and participating in meetings, which do not add value. If you consistently do not get valuable conversation from a skip level, cancel the one-on-one series. Don’t spend either of your time on something that isn’t helping. This can take several forms. For example, can you consistently tell that they are saying what they think you want to hear? Are the conversations always met with short answers or no curiosity from them? Lastly, if they consistently miss the meeting time, then it is not valuable to them.

Do your best to avoid missing the one-on-one without advanced notice. Likewise, try to avoid canceling or rescheduling at the last minute. Sometimes, it is necessary, but communicate what is happening and offer to reschedule.

What not to include

Some topics are not for skip-level conversations.  I suggest not bringing these up or redirecting the conversation to their direct manager.

Improvement or disciplinary feedback that their manager still needs to provide directly to them. These topics are best handled and followed up with their direct manager.  You are likely going to be missing some crucial context or information to be able to give good feedback. If you have feedback for this person, work through their manager to deliver it.  However, you can reinforce feedback their manager has given them by offering mentorship or guidance on the topic.

Wrap it Up

Skip-level one-on-ones can be a great way to increase your connection with your greater organization. They can also be a valuable source of understanding as you set direction and share up the organization.

Set clear goals and agendas for your skip-level conversations. Do not surprise anyone on your team with these discussions. Lastly, reflect on your skip-level conversations over time to ensure you are not wasting anyone’s time.


If you found this insightful, check out these other posts.

What Does a Good 1-on-1 Look Like?

One-on-ones with My Manager are Kind of Terrible

When Candid Communication Isn't Enough

 

If you want to improve your leadership skills or want to talk more about improving your one-on-one conversations, consider connecting with me.

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