I want to know what it feels like to be your boss

“I want to know what it feels like to be your boss.” 

Whether you’re in an interview, or writing a resume, or networking remotely, this is really what every future boss wants to know. What does it feel like when you are working for me? How can you help me succeed at my job? What will be the good feelings and the bad feelings we’ll have working together on the problems and opportunities here at this company? 

Bosses want to know what their experience working with you will be like. 

And that’s a problem, because it’s much easier for you to describe, “what it felt like to be me.” 


In re-telling our work histories, we lived those experiences. We had the challenging co-workers, or the lack of resources, or the insurmountable problem, or the regulatory issue; in our memory of the events of our career, it’s natural to share these experiences from our point of view. 

But that’s not quite the same as your future boss’ needs. What she wants to know is — what will it feel like to be your boss? What will she get out of this working relationship? 

And the best way to communicate that feeling is to talk about numbers. Just like OKRs are the best way to communicate team success, numbers are the best way to communicate what it felt like to be your boss, such as: 

“We set x goals, which were y % above the prior year, and then we took these steps to deliver on them.” 

“I helped increase the revenues by x % through these specific actions.” 

“When we had to reduce cycle time / computing cost / time-to-market / expense ratios, my boss and I agreed on y-path, and by doing the following 1, 2, 3 items, I was able to achieve the goal.” 

Focusing on the facts of your work product, work style and work output, makes the best case for what working with you will be like. In conversations and interviews, let people know that if they work with you, here’s what they can expect… the tasks that you are able to conquer readily, and the ones you are still learning… the situations where you are strongest, and those you’re not… the problems that you love solving, and those that you dread. As you mature in your professional career, you’ll also mature in your communications and your ability to:

  • accurately convey your accomplishments without feeling embarrassed or bashful.
  • discuss your preferences within a role or field or industry.
  • have conversations about hard failures or tough setbacks that you’ve overcome and learned from.
  • share thoughts about work styles that are effective, and ineffective, for you.
  • communicate what you’re good at, by joking about what you’re bad at — that sense of self-deprecation that gives an air of command, while not coming across as braggadocio.

Developing communication as a skill goes hand in hand with growing in your career. 

I hear it often enough: “it’s embarrassing to talk about myself”, “I’m not one to brag”, or “I wasn’t raised to toot my own horn all the time, I just do the work.” 

Being uncomfortable with ‘horn-tooting’ comes with a very real cost to your career. To the extent you are unable to convey your value to future employers, they will underestimate, underappreciate, and, worst of all, underpay you. 

An important part of professional maturity is learning how to communicate your value effectively, and learning how to separate the social from the commercial. There is a distinction. 

You were raised to not brag about yourself in social situations. And you should continue not bragging about yourself in social situations. 

Your work is a product that you sell, commercially, for over $100,000 per year. And of course you’re always hoping to increase that figure.

To get the highest price for your product, in this case, your work, you’ll need to effectively communicate the features, benefits, and advantages of the product to your clients. In this case, your future boss. To the extent you under-communicate your value, so much will you be underpaid. And one of the reasons you joined Ladders was to make sure you were being fairly compensated in your career. 

So while it’s much more comfortable to express “here’s what it felt like to be me”, what you really need to communicate is “here’s what it feels like to be my boss”. 

By putting yourself in your boss’ shoes — by showing him or her what it will feel like to work together — you’ll be getting the most out of your career.