Skip Level 1:1s – Recipe for disaster or success?

by | Jun 21, 2023

Skip level 1:1s can be an extremely effective way to build your rapport and cohesiveness with your larger team. Obviously skip level 1:1s can only happen if you have direct reports who are managers, thereby giving you the possibility of having 1:1s with their direct reports.

There are quite a few things to navigate in order to hold successful skip level 1:1s and some of these apply to any skip level meetings (not just 1:1s) that you may have with one of your managers’ direct reports.

First and foremost, your direct reports are your people. Your direct reporting manager’s people are not directly your people.

The “make or break issue” for successful skip level 1:1s

In using People First Operations™ concepts, your first obligation and consideration is to the manager who reports to you. As such, you need to make sure that the process that you’re using to meet with their direct reports is serving your direct reporting manager first. It certainly seems obvious that we would want to make sure that our people were feeling served by our involvement with their direct reports but I’ve seen colossally bad situations happen over and over again where a manager is completely “managed around” and the “director” (or any upper management) goes right around this unsuspecting manager and directly manages one of their direct reports…or worse, the whole team! Needless to say, it leaves that manager wondering what they’re even there for. That is a great way to demotivate and disrespect them. You might get away with it once or twice, but it won’t take that person long to see the pattern. At that point, you have trouble brewing between them and you. It’s obviously best to avoid that situation at all cost. Honestly, that move is worse than micromanaging the manager. At least micromanaging that manager involves their participation and engagement, albeit poorly.

The “two bosses” problem

I also want to bring to light that if you are giving instructions to this person directly, you are now forcing them to have 2 bosses. This puts that person in a very difficult position because you are not the one who is directly giving that person their performance review and you may be giving them instructions that at least competes with the directions and instructions that their actual manager is giving them. If that’s true, then you’re likely forcing them to put in more time and effort that could be beyond what is reasonable or acceptable. This is bad for them, it’s bad for your direct report, and it’s ultimately bad for you since you want your greater team to function smoothly, efficiently, and with as few pain points as possible.


If at this point you disagree with me, I would simply ask for you to take a minute in some calm reflection to consider how you would feel (or what you would think) if your manager were to go around you routinely and directly manage your people. If you can honestly say that it wouldn’t bother you one bit, then I probably cannot convince you in this blog post alone. You may just need to talk to your people as their experience may be different than your own and really listen to them.

Also consider the situation where your boss and your boss’s boss were both piling on work for you to do separately. How would that make you feel or what would you think about that?

Moving forward…

So how then can we have skip levels that put our own people first and also really serve well the person that we’re meeting with? Let’s get into it!

Scheduling the 1:1

When you (“the boss’s boss”) schedule a skip level 1:1 with someone, they will first wonder if they’re being called “into the principal’s office”. If no information is given as to the nature of this meeting, that will create an information vacuum and their mind will fill it, usually, with something negative or incorrect which is likely fed by some amount of fear or insecurity. To avoid this entirely, you should make sure that in the invitation, you’ve provided the stated outcome and an agenda (see below). From that, they will feel much better about the meeting to be had with you and not be afraid. Once you start the meeting, they then should understand that they are very important to you; however as conversation happens and topics “tick by”, they will also see that your direct report (their manager) comes before them in terms of who you’re serving. This would not be dissimilar to when we have discussions with our kids. For me, if my kids start to speak disrespectfully about “Mom” to me, complaining about her and her actions, they will quickly find out that I will not stand for them disrespecting their mom to me. They will get a very clear indication that that is not ever ok and that I’m “for Mom” before I’m “for them”. In that situation, how they speak about someone is every bit as important as what they say about them and they are accountable for both of those.

A Suggested Agenda

The agenda that I would typically use for my skip level 1:1s would maximize time for them talking and me listening. I would avoid (yes, I did say avoid) giving them any tasks to do. Doing so would immediately break the rule of not managing this person directly and only allowing their task list to be affected by their own manager (my direct report). I would instead maximize the time I spent building a healthy relationship with them and not have them go giving me a “status report” – that would not be the focus of what I wanted them to tell me about. My agenda would also largely consist of asking them open ended questions. And I would be sure to let them know that they also could ask me anything. So, here’s my typical agenda for a skip level 1:1:

  1. Check in – How are you doing? (For this one, I really want to know – not a superficial “ask” and their answer could and usually would lead into some other questions that allowed me to better understand them, their challenges (at home and maybe at work), their hopes and dreams, hobbies, etc.
  2. Is there anything you want to tell me? Some thing(s) you feel I should know?
  3. Is there anything you want me to tell you? Some thing(s) you need to know? Questions that you have?
  4. What thing(s) could I do to help you, your team, and your manager? Any blockers or pains that you have?
  5. (Time permitting and if you want to go here) What are you doing in the next week/month/quarter/year that you’re looking forward to?

Most of the time, the first 4 questions would last me an hour. However, there were times that we whipped through that Q&A quickly and so that 5th item could serve to fill the rest of the time…see below why that is important.

Get to know them

Generally, the goal of the skip level meeting is once again to build a relationship with those on your greater team. As such, spending time to get to know them is extremely important. Find out about their own story, how they came to the company, their background/career, their interests and hobbies, their family (if they have one), and how they like to spend their time at play and at work! If you have spent time doing the Clifton Strengths Finder assessment with your team, it would be a great idea to look at their Top 5 strengths as a precursor to this meeting. Getting to know each person alongside their Top 5 is wonderful, not only for you but also for them! As I have had someone’s Top 5 in front of me and in my mind, it’s allowed me to ask some really insightful questions that genuinely make the person feel valued and cared for. I’ve gotten looks from some of those questions that communicate “How’d you know to even ask that?” and some will even ask me! Of course, I’m honest with my reply stating that knowing their strengths helps me “see the world a little bit like they must see the world”. Most folks think that that is pretty cool…but results may vary 🙂

Let them get to know you

After you’ve had enough 1:1s with this person and you feel that you have gotten to know them, you may find that they ask you about yourself. It is easy to try to turn the tables and make it all about them but during skip levels as well as in your normal 1:1s with your own direct reports, it IS important to let yourself be known too! So open up to them and let them know your own story, know some about your successes and failures, and in general, this is a time where you can “model the way” for being a bit vulnerable. Obviously you need to use some careful discretion about what you open up about but letting folks know that you’re human and you make mistakes and also learn from those mistakes with a few examples can be really endearing and trust-building.

Discover their super strengths

It is hopefully the case that their own manager has already gotten to know this person’s super strengths but if People First Operations is new to your organization, it’s actually probable that they have not. Most managers do not know their people’s super strengths – the gold inside each person on their team. So this is an opportunity to really dive into what they’re very passionate about so that you can find out what “muscles they like to flex” – those are going to be the strong ones that you will be able to champion on their behalf. We want our folks to be fully engaged in their work and thriving as they do it. As such, to be able to put them in their sweet spot at work is really a big goal for every single person.

If you do discover some super strengths, and you will if you spend time on this, and their manager doesn’t yet know them, you can come alongside them and give them that information along with a suggestion that if there’s opportunities to give to them so that they can use those strengths, they have your full support in doing so. Be a champion of your direct report’s people and help your managers position their own people correctly on projects and work on their team. Let them know that it’s because you want THEM to be successful and are happy to help them and their teams thrive. It’s a coaching/mentoring opportunity for you as well as a leadership opportunity to help them see how they can move in this same way.

Disputes may be “aired out” to you

As you establish a measure of comfortability with those you’re meeting in skip levels, it is possible that a dispute or disagreement can surface that perhaps you were not aware of and this is an opportunity for you to serve both your direct report as well as their team. So how you “show up” in these moments are extremely important. It is not necessarily the case that you should instantly jump to the side of your manager. Nor is it the case that you should jump on the side of the person presenting their side of the story! But you want to make sure that you are being fair and impartial and express that you want to hear both sides of the story. As they say, “it takes two to tango” and there are always two sides to every story (and maybe more!). In these situations, it behooves you to ask a LOT of questions from at least the two people involved, but also from anyone else who was present during the time(s) of the events leading to this.

“Death by 1000 cuts”

These 1:1s also provide the opportunity for you to find out about what pains this person is dealing with on a day to day, week to week, and quarter to quarter basis. After creating the psychological safety that is needed in this relationship, it’s very likely that you will hear some real “stuff”. Sometimes that stuff is actionable and sometimes it’s not…at least not immediately.

During my time doing skip levels, I would often hear that quarterly planning was too painful and did not yield enough “goodness” to justify the expense of a week of planning, including the 2 long days of PI Planning meetings. (if you’re not familiar with PI Planning, it’s part of the Scaled Agile Framework) I welcomed this feedback always and listened to it closely. I would often ask folks who shared this what they would do instead. I would also share that whatever we did instead would need to be communicated upward to higher levels of management because a big part of our quarterly planning was doing “our part” to feed communication up the chain so that those above knew what we were committing to getting done. Oftentimes, the person would not be able to provide a reasonable alternative and they began to understand why quarterly planning was important for the company as a whole, which is another key benefit to skip levels – disseminating a higher level view/perspective of things happening to those who need to know.

At other times though, truly painful and real issues were brought up that I didn’t know about but that were things that we could do something about. When getting information like this in a skip level, you do have to be careful about if and how you surface it to their manager/your direct report. Hopefully you have a relationship with them that allows them to know that this is very much a partnership and that they can trust you when you ask them about things you’ve learned in a 1×1. My most senior and reasonable managers handled my questions with poise and grace. Sometimes they’d laugh because they’d heard it so many times and there was a story or context that they wanted to share with me or sometimes they’d nod in violent agreement and we’d be off to figuring out how we could solve that pain point. In either case, it provided great opportunities to bond with my people and problem solve together for the betterment of their team and their productivity.

Sometimes the truly painful issues that get brought up to you are not from the work side but of a much more personal nature. If, in a skip level, that type of issue was made known, I would usually ask them if they’d told their manager about it already. Most of the time, they had. However, in the off chance that they hadn’t, I would let them know that I would not be the one to tell them and that this would stay here between us until or unless they wanted my help in letting their manager know. I would however encourage them to discuss it with them especially if it was of a nature that would impact their work. Additionally, the Family Medical Leave Act (FMLA) was also something that we could discuss if the situation allowed for that to be considered. If we did discuss that, then it was going to be up to them to approach their manager and ask to discuss the situation as well as their desire to pursue time off through the FMLA.


There is honestly a lot more than can be said about skip level 1:1s but I hope that this has helped you consider the relational dimensions and affects involved in holding 1:1s that serve your people first and allows you to create a fantastic work culture on your team. In so doing, you will be creating the team that everyone wants to join and no one wants to quit!!

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