What does it feel 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 at an event, this is really what every future boss wants to know… what does it feel like when you are working for me?  How will I be able to get the results from you that I need to succeed at my job?  What will be the good, and the bad, feelings we’ll have working together on problems and opportunities here at this company?

And that’s a problem for just about all of us, because we tend to be much better at telling people “here’s what it felt like to be me.”


We were there, we experienced it, we had the challenging co-workers, or the lack of resources, or the insurmountable problem, or the regulatory issue, and in our remembering of the events of our career, it’s natural for us to share them with others in just the same way we experienced them.

And that misses your future boss’ point — she wants to know, based on your past, what it will feel like to be your boss in the future. He wants to know what he’s getting out of this bargain, not what you got out of yours.

And, look, I hear it all the time: “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.”  

Me too.  And I said some of the same things when I was interviewing for jobs earlier in my career, especially right out of business school.

But you have to realize that this discomfort with ‘horn-tooting’ comes from the contradiction in context.  You were raised to not brag about yourself in social situations, but work, however social it may seem, is a commercial situation.

And because it’s a commercial situation, there are real dollars involved. Just as with any product, the extent to which you mis-communicate the features, benefits, or attributes of a product is the extent to which your customers or clients won’t buy it.

In the case of employment, that product is you, and when they don’t buy because you mis-communicated, that means you won’t get the job.

So the extent to which you under-communicate your value is the extent to which you’ll be underpaid.

And you don’t want to be underpaid, do you?

But there’s actually a great way for you to kill two birds with one stone and communicate effectively to future bosses, colleagues and employers both how you match what they’re looking for, and not feeling too embarrassed in the process.

And you do that by focusing on the facts of your work product, your work style, and your work output.  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.

– 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.

Because here’s the thing.  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”.

In a modern, information-driven and collaborative workplace, being able to communicate well is your job.  If you can’t communicate well with your team, your co-workers can’t work with you as effectively, your boss can’t assign (or re-assign) you productively, and clients and customers won’t know how to make the most of your efforts.

When it comes to “thinking” work, communicating is just as important as the thinking itself.

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

I’m rooting for you.