Many times the subtle anchor that holds employees back from quicker career growth is merely a lack of the right kind of visibility from the right people. In highly bureaucratic organizations most of the great work that you do will be many layers away from the most important decision-makers in the organization. While you might be able to impress your boss with your superior efforts and output, doing so will only enable you to climb one rung of the corporate ladder at a time.

Two years ago I found a way to hack this common corporate limitation. In a joking manner, I refer to this tactic as “dating your boss’s boss”. By this, I don’t literally mean having a romantic encounter with a coworker, instead, I mean using a specific method to request a simple meeting with someone higher up in your organization than you normally interact with.  I’ve used this tactic to jump multiple levels of the corporate ladder in my life and more recently, I have witnessed others have similar success with this tactic. This article is the first time I have shared this tactic publically.

The goal of the “date your boss’s boss” tactic is to build positive visibility within your organization above your normal sphere of influence. To do this, you must show your boss’s boss that you are valuable and that you can help solve their most important problems. The tricky part of this is that you need to do this without outwardly bragging and without stepping on the toes of your boss.

In order to accomplish this feat, you need to send your boss’s boss one of the best e-mails that they have ever received. I’ve included the actual e-mail script that I have used below.

The key elements of the e-mail are:

  • Show your boss’s boss that you are interested in solving their problems (rather than acting like most employees and just going to them and identifying a new problem that needs to be solved)
  • Provide a well thought-out agenda so that your boss’s boss knows that if they accept the meeting, the time will be well spent.
  • Make it easy for your boss’s boss to fit you into their schedule by highlighting times that they already have available.

Feel free to use the script below as-is or modify it to fir your own context. While sending this e-mail may be scary, it has the potential to get you the visibility you need in order to leapfrog your way up your organization’s management ladder.

Meeting Invitation E-mail Script


I’m YOUR NAME from the DEPARTMENT NAME team. I’ve been working at the company for AMOUNT OF TIME. Like you, I am big into self-development and would really love the opportunity to take you to coffee in order to learn more about you and your goals for COMPANY NAME. I am very eager to pick your brain.

I realize your time is at a premium so I have prepared the following agenda for you to see beforehand.

Proposed Agenda:

  • When you think of the best employees who have worked for you, what makes them stand out in your mind?
  • What is your biggest problem and what can I do to help solve it?
  • Who or what is our biggest threat?
  • Where do you see COMPANY NAME in 1 year? 5 years? What does success look like for you?
  • Where do you see the industry trending and what are we preparing to do?


I see from your shared calendar that you have the following times available:



Do any of those times work well for you?


Thank you in advance!



After you send this e-mail, let the receiver take their time to respond. After they do respond, confirm the time and place and prep for the meeting with a printed agenda and something for you to take notes with. You are likely going to want to do more listening than talking.

After the meeting takes place, immediately follow up with your boss’s boss with any information that was requested or discussed. A month later, consider following up with them again if you have any valuable information to share. Keep yourself on their radar.

I hope this tactic works as well for you as it has for me and my friends. Let me know how this works out for you either in the comments below or via e-mail (My e-mail address is available on this page).