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Setting a Meeting With Your Boss’s Boss

By In Workplace

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.

Their Mindset

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.

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I help companies turn their technical ideas into reality.

CEO @Sourcetoad and @OnDeck

Founder of Thankscrate and Data and Sons

Author of Herding Cats and Coders

Fan of squash, whiskey, aggressive inline, and temperamental British sports cars.

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Asking For Feedback the Right Way

In Workplace

The vast majority of people will agree that feedback is the most important tool we have to improve ourselves and others. How else are you supposed to know if you’re doing a good job if nobody tells you? How are you supposed to improve if your weaknesses remain hidden? Understanding these two oversimplifications allows most people to buy into the idea that feedback is a valuable tool. Many of us even pay real attention to the act of asking for feedback or offering it. The problem is that 90% of the time, we’re doing it wrong.

I typically see two main categories of feedback being handed out:

  1. The “good job” feedback.

This is the easiest type to give, and it’s really important. Letting someone know they did a good job on a task is very powerful. Giving feedback directly after the task’s completion makes this even more impactful. Rapid, positive feedback has three huge benefits:

  • Positive feedback adds to the bank account of trust in the relationship.
  • Letting someone know their strengths can help build a person’s confidence.
  • It creates a culture of positive reinforcement.
  1. The classic “compliment sandwich.”

A lot of critical feedback is in the form of “I think you did this well, and this could be better, but this other thing was good.” The compliment sandwich is a really useful way to deliver difficult feedback safely, without hurting someone’s feelings.

So what is wrong with these two approaches?

These two approaches themselves are not broken, but the way they’re used is. And it’s not the person giving the feedback’s fault either! It is the person soliciting the feedback who is to blame.

Requests for feedback should be specific — based on intended outcomes or incremental improvements in an area where someone is focusing on improving.

Why don’t we ask for feedback the right way?

Motivation is a big reason for starters. Most people have jobs where they are stressed all the time, totally disengaged, or lack any support from their peers and supervisors. In these situations, it’s difficult to imagine finding the motivation to work out where you should improve. Why should you make strides in a workplace you don’t care about?

The other reason we don’t do feedback correctly is because it’s hard. It requires effort and direction. Knowing what you want and then working towards it is much harder than just showing up. Many people don’t realize that their careers and their lives are in their hands, so it’s a perspective that requires a person to step back from their day-to-day life and actually think about. No one, and I mean no one, does this instinctively or naturally. It’s a habit and a skill that we have to learn.

How can we fix this?

The solution to many of life’s problems is in the cunning use of paper and pens (or pencils). Writing down your ideas is a life-changing skill. I’m not going to go into the psychology and the validity of this point, but if you want to read more about it, you can here, here, here, and here — and a million other places. If you start with a simple list of your goals and then a shortlist of your strengths and weaknesses, you’ll be off to the races.

Start with your goals. What do you want out of your life, your career, and your current job? Just those three for now.

When you’re done, list what skills and experiences you’ll need for each one of those three goals. (Don’t write down anything about changing other people.) Next, write down which skills and experiences you already have and where you are weak.

Create a list

For example, a very stripped down version might look like this:

  • I would like to be a manager or a team lead in the next few years. Managers need to:
    • Skills
      • Be able to manage up.
        • I’m not great at communicating with my manager the way she likes.
      • Understand business goals.
        • I think I’m good at understanding why we are working on something.
      • Design and measure specific data for success.
        • I think I’m very good at defining success metrics.
      • Design processes and make sure they’re being followed.
        • I’m pretty terrible at making plans and getting others to follow them.
      • Communicate clearly with their direct reports.
        • I’m a little shy when it comes to voicing my opinion.
        • I’m too much of a people pleaser.
    • Experiences
      • Develop a background in the type of work they’re managing.
      • Have led smaller projects in the past.
      • Learn about management from books or school.

Write down some feedback questions

Now pick two, ONLY two, to start with and start working on them. Once you know which two you’re going to work on, write down an example feedback solicitation for each one.

  1. Pick one strength and start getting confirmation that you are actually good at it. For example:
    • I’ve created a list of success metrics for this next step of the project. Could you look at it and let me know if this is good? I’m trying to make sure that I’ve got this down.
  2. Decide to strengthen one of your weaknesses. For example:
    • Can I ask you for some feedback? I’m trying to voice my opinion more in team meetings while still trying to work toward consensus. Did you feel like I spoke up more than usual in that last meeting?

And there you go! Those are feedback questions. There are two huge benefits to this technique:

  1. You are now the one driving your career and skills growth. It’s no longer a random crapshoot of lessons you’re picking up from the work environment through hints, clues, and osmosis.
  2. It signals your intent to the people you are soliciting feedback from. This tells them you are serious about improving in some aspect. Your actions demonstrate that you are open to change and are inviting others in to help. Your openness tells them you are a thoughtful person who cares about growth. It lets them know that it’s okay for them to ask you for feedback, too. In this way, feedback can be like sizzling fajitas at a restaurant: When the first person orders it, everyone else hears the sound and smells the sizzling peppers and starts ordering the same thing.

Unsolicited Feedback

Every now and again, you are going to want to give someone unsolicited feedback. Hopefully, this is mainly in the “good job” category, but sometimes you have to make people aware of a problem that they are not working on. General feedback like this still has utility, but use it lightly. Treat these situations as though your target had asked you, “Where do you think I can improve in [x] specific area?” and then hit them with the compliment sandwich. With any luck, this new data can become the focus of their next set of skills to work on. Sadly, it’s often ignored.

You can’t guarantee that taking your career into your hands, building out a plan, and then executing that plan will work. You cannot predict how people will react when you ask them for clear and specific feedback. If no one around you is going to enjoy the sizzling fajitas effect of your earnest feedback attempts, then they don’t deserve you!