That’s me

The first time it happened, I was 25 years old and working in Spain on a consulting project for a big Portuguese telecom company.

I was on a small project team responsible for a pile of data analysis that would drive the main project recommendations, and we were nearing a final deadline. The analysis, it turned out, was way over my head. And yet, as I looked around the team and our small office for someone to tell me how to go about it, I had this sinking feeling that the person who knew best what to do was me.

It was terrifying.

Partially the fear came from objectively not knowing enough. I had neither the analytical chops to know how to proceed nor the network of relationships to quickly find someone who could help in time. And I was sure that our firm was getting paid far too much to make recommendations based on what I knew.

So while that moment, stemming from poor planning and preparation, is something to avoid, getting to have that feeling was priceless.

I still remember the quiet, mortifying stillness of, “It’s up to me.”

What an important feeling to be able to identify, because once you’ve felt it you can’t unfeel it, and then you can notice that feeling and notice how much easier it is to kick a decision somewhere – up, down, sideways – to gather more information or maybe to put off deciding entirely.

We kick this habit like any other, with both discipline and nuance.

If you want to learn to swim better, or hit a ball better, or do a yoga pose better, you start with the big muscle groups and body angles and work your way towards subtler adjustments. Just so in the workplace: you begin by making calls in the big, obvious moments where you’ve got no choice but to decide; and you work your way through to smaller moments of stalling, hesitation, and the magical sleight of hand we all engage in to open up “outs” in case things turn out wrong.

It is so much easier to avoid responsibility and future blame.  And it is so much more important to practice putting ourselves on the hook, to practice being the kind of person who makes calls, to practice stepping in to uncertainty.

Step up. Decide. Then make it great.

The person we’re waiting for? That’s you.

Entry Level

The biggest fear when taking an entry level job is whether you’ll end up doing meaningful work. I still remember fretting that I’d spend the summer of my first “real” internship in the U.S. Senate fetching coffee and making copies (I didn’t end up fetching coffee…the copies, yeah, there was some of that).

It can seem like the way to protect against this is to ask lots of very specific questions about the role: what exactly will my responsibilities be? What will a typical day look like? This can help you a bit, but it can also backfire, because the best places for you might be the ones where these questions don’t get the clearest answers (also, it’s tricky to ask these sorts of questions and still communicate that you understand that your job is going to be to make those around you more successful, and that you’re willing to take a “whatever it takes” attitude.)

Better, I’ve found, to focus on two things.

First, when talking to your potential supervisor, figure out if she seems genuinely to care about the people around her, and that she will devote mindshare and energy to investing in you. For example, you could ask a question like, “can you describe someone who has worked for you who has gone on to do great things?” and then focus as much on the energy she has in answering the question as on the content of what she says.

Second, and probably most helpful: try to work in a place that is dynamic and growing. If a place is dynamic and growing, that means that new and unexpected (but cool and exciting) things are going to come down the pike. And if the place is dynamic and growing, that also means that it’s probably not fully resourced to attack that next great opportunity – that’s where you’re going to come in.

In these sorts of places, you’ll hear lots of answers about the general arc of growth and the future, but you won’t hear exactly the specific thing you’ll get to work on…because people don’t know, yet.

For a fun example, check on this great rap by the Ladies of Hamilton, with the lead part (of Alexander Hamilton) played by Morgan Marcell. Morgan is new to Broadway and she’s part of the Hamilton ensemble. There’s no conversation she could have had with the show’s producers or directors that could have predicted that the Hamilton cast would put out YouTube videos that would be seen more than 300,000 times. But she joined something she believed in, she put in the work, she did enough that her peers recognized her talents, and she worked with people who were proud to shine a spotlight on her when the opportunity arose.

And when it did, she was ready to step up.

(Oh, and @Lin_Manuel, yes, I do enter the lottery every day….)

What should I do, boss?

A typical email:

Dear Boss,

Here are all the things going on with this project.   And also this.  Plus there’s this other thing we need to keep in mind.  This too, which is really important.  And I’m worried about this.

What should we do?

Employee

When you’re about to ask your boss to make a call on something, it’s worth stopping for a moment and asking what you’re doing and why.  You have the most information, usually, so the questions you might ask yourself are:

1.       Am I actually worse at making decisions than my boss?

2.       Do I not have the authority to make decisions?

3.       Or is neither of the above true and am I just avoiding responsibility for making a call?

The kicker is, the more you go ahead and decide stuff for yourself, the better you get at making decisions and the more authority you get (if this doesn’t happen, go work for someone else.)

Yes, sometimes you don’t know and/or you really need a thought partner, but I’d guess that happens 1 out of 5 times, maybe 1 out of 10 times, not most of the time.