Most people don’t have a problem talking to their boss or direct supervisor. Hopefully, you have casual access to this person every day and formal interactions through one-on-ones and other reviews. Sometimes though, you want to (or need to) go over your boss’s head. That can be a challenging and stressful task. In this post, I’ll go over a few reasons you might want to do this and some tactics on how to approach it.
This may be easier or harder, depending on how many layers of management and bureaucracy your company has. It will be much easier to contact the CEO of a fifty-person, founder-led startup than in a publicly-traded firm.
Skip Level Meetings
Some organizations institutionalize these meetings. People call them “skip-level” meetings. They’re a good way for upper management to get an idea of how their direct reports are doing. That’s not what this post is about. This is about how you should set a meeting that skips a level — in other words, going over your boss’s head.
The first thing you need to know is that getting a request for a meeting that bypasses a layer of management can be stressful for both parties involved. Out-of-the-ordinary meetings often put managers on edge when trying to work out why the meeting has been requested.
There have been more than a few occasions where a team member whose manager is my direct report has asked for a meeting, and I prepared for the worst. “Are they going to quit? I thought they were happy here? Do they have a complaint about their manager?” These thoughts race through your head. It gets worse when I request an agenda, and the team member responds: “Well, I would rather discuss it in person.” Now I KNOW they’re going to quit. Well, I think that. When the day comes for the meeting, I sit down and ask: “So what is all this about?”
- “Well, Greg, I just wanted to say that my [manager’s name] is so amazing. I think you should give them a raise.”
- “Greg, I wanted to let you know I’m buying a new house! I thought you would be proud.”
- “I wanted you to be the first to know; my wife is pregnant!”
At this point, I am flooded with a mix of emotions. I’m relieved, happy, and a little annoyed that there could have been SOME foreshadowing in the request.
So, here are some points to consider before you decided to raise the blood pressure of people who might have something to say about your annual bonus.
When Is It Appropriate?
When You Have Good News
This is the best! Sometimes you and that person two levels up have a personal or long-term professional relationship, and you have to let them know something before anyone else. This will make their day. Just let them know the meeting is positive beforehand.
It’s About Your Direct Supervisor
Praise or recommendations about someone’s direct report is often the highest compliment you can pay a manager. Do this!
Complaints or concerns need to be handled VERY carefully. Only approach your supervisor’s supervisor if you have not been able to resolve the issue with them. It’s likely the person two levels up knows about the issue and is giving advice or coaching their report on it. However, there are exceptions. You are ethically obligated to report any claim about harassment, bullying, inappropriate behavior, criminal activity, or discrimination.
You Want to Apologize for Something or Commit to a Course of Action
Sometimes we make mistakes. Well… a lot of the time, we make mistakes. Saying sorry in-person shows courage and professionalism. Just don’t grovel or overdo it.
You Want Their Expert Opinion on Something
There are many cases where your skip-level supervisor is an expert in some professional or technical task. They would love to talk your ear off about something they knew when they were an individual contributor or about their bread baking hobby. Just be warned!
You Want to Talk About Your Supervisor’s Peer
In rare cases, you will want to have a conversation with your boss’s boss about one of their other direct reports. All the same rules above apply here, but know that this can be very sensitive if you don’t have a really clear reason why you are going around your supervisor.
When is It Not Appropriate
You Want to Gossip
Gossip is never a great idea in the workplace, but it’s especially bad in a skip-level meeting. It will make you look petty and wasteful of company time. If you hear a rumor about anything from a merger to an HR issue, ask your direct supervisor about it directly. Don’t go to her boss and try and get the “real” story.
You Want to Resign
This one is tricky. Sometimes it feels easier to hand in your notice to your supervisor’s manager simply because it doesn’t feel as personal. It also might feel more natural to resign to the person who hired you, and there now might be a layer of management in between you and them.
There are some organizations where this is appropriate, but my suggestion is to let your direct supervisor know. If you go over their head, they may think they are the reason for your leaving, and if that isn’t the case, then it is not fair to them.
You Want to Ask About Your Peers
Similar to gossip, talking about, or asking about, your peers is something you should only do with your direct manager. Better yet, handle it with your teammate yourself – managers are there to guide the process, professionals manage themselves.
You Are Looking for a Raise
Raises should always be discussed with your direct supervisor first. If your manager is not prepared to take your request up the chain, then they are not going to be an advocate for you when their boss comes asking about why you didn’t go to them first.
General Rules to Follow
There are a few things that you will want to do in all cases:
1. Most managers appreciate employees reaching out. Remember that they are regular people just like you, and you should treat the meeting with the same level of care and professionalism you would with any meeting.
2. If you don’t request the meeting with an agenda, the assumption will be you have very bad news or are resigning. Clearly set the expectations for the meeting beforehand (unless it is so sensitive you can’t put anything in writing). Even if it is bad news, you should set the tone when you request the meeting.
3. Think through what you’re going to say beforehand. Often you can just work through the agenda, but if you do have something sensitive to discuss, you can write it down first to rehearse the conversation. This way, you can avoid hyperbole or gossip.
4. Take notes during the meeting. It’s still a meeting, and it’s the professional thing to do. The same rules apply. Work out what actions are going to be taken as an outcome of the meeting. Make a note of any follow up it will require.
5. Discuss with your boss’s boss how you are going to communicate the outcome of this meeting (or its existence) to your direct supervisor. A simple, “Would you like me to discuss the contents of this meeting with my manager or would you?” is perfect.
6. Send a follow-up email! Oftentimes, people get a little stressed out when doing skip-levels, and so the standard meeting etiquette goes out the door. When meeting with your boss’ boss it is the time to take MORE care than usual. Send a thank you message, a summary, or both, and you will look more professional. It’s also the correct, human thing to do.