I’ve worked with a number of bosses in a variety of creative industries. And in my experience, these are industries in which some of the greatest results require a good balance of skill and creative experimentation. I’ve come to learn this combination means that a good manager (for better or for worse) won’t—can’t, really—give you clear guidance 100% of the time.

Not feeling like you have clear instructions can be frustrating, to say the least. When you’re in a role where you’re continually learning, it’s natural to look to your supervisor to advise you when you’re stuck on a problem or at a loss for solutions. So what do you do when that person simply doesn’t provide explicit directions? How will you ever know if you’re on the right track or if you’re completely wasting your time?

When it seems as though the person that’s supposed to be leading you toward success isn’t making it any easier for you to get there, what are your options?

OK, first, let’s give your boss the benefit of the doubt and examine how three common vague statements could—and maybe should—be interpreted.

1. “I Trust You to Make the Right Call”

What it Sounds Like

There’s a “right call” and a “wrong call,” and I expect you to know the difference by proving it to me.

If it feels like your boss is trying to test you (or worse, catch you failing), then it might help your nerves to take a step back. Consider why she might be giving you more responsibility (because hint: That’s not necessarily bad news).

What it Actually Means

I trust you to know how to make this decision. If I really felt it were that high stakes, or that you were incapable of handling it, I wouldn’t be leaving you to diffuse this bomb alone.


You need to take initiative on your own—because I don’t have an easy answer to this either.

In either case, the statement is about granting freedom, because you honestly have earned it. This may be hard to swallow if you’ve worked with nightmare management in the past, if you’ve gotten used to working under micromanaging reigns, or if you’re the kind to jump to imagining the worst.

From a practical point of view, your failure wouldn’t exactly make your supervisor look good either. So, as easy as it is to imagine that she’s acting as your ultimate career foil, that’s most likely not the case. Think about your past experience working with this specific type of problem, researching solutions, and making decisions. Somewhere along the way, you’ve proven that you’re very capable of handling things on your own, so cut yourself some slack and be confident in your next move.

2. “Keep Going and See What Happens”

What it Sounds Like

There's a chance this could be cool, but you could also be wasting your time. We’ll see which it is once you’re done.

Does it feel like your manager just wants to keep you busy because there’s nothing better for you to be working on? Or worse, because she doesn’t trust you to be doing anything else? Before you let your mind wander to that suspicious place, take a breather for yourself. Your boss is probably thinking of the big picture, and if you can do the same, it’ll help you understand where the project needs to go next.

What it Actually Means

This is a really innovative approach, and I think it has potential—you’re definitely on to something. I’m curious to see what you can come up with on your own, and don’t want my own opinions to derail your creative process.

Fortunately, most companies don’t have unlimited resources to keep you busy and waste your time. So, if it even looks like you could be on the wrong track and wasting company resources doing it, know that your supervisor would put a stop to it if that were truly the case.

You may believe you could be doing something worthwhile, but trust that your boss sees this as the most important assignment for you right now—even if that means putting other tasks on the back burner.

Use this period to take creative risks because that’s what your manager is actually trying to encourage here. If there’s time, consider trying multiple approaches to discover the best possible option.

3. “What Do You Think?”

What it Sounds Like

I don’t like what you did, but I want to hear your defense. Try to convince me why you’re right.

This question can often feel like a trap. Say the wrong thing, and your boss will find out that you made decisions for all the wrong reasons, or worse, that you’re a fraud who’s unqualified for the job.

What it Actually Means

I’m curious why you made certain choices rather than others. Given my experience, I would’ve approached it differently, and I’m intrigued by your thought process.

Being honest about your thought process is the only way you can get feedback on it—otherwise you’ll continue making the same mistakes, or worse, you’ll ditch those practices without fully understanding why.

Disagreeing with your boss is a huge learning opportunity, though it might take a little courage if you’re unaccustomed to doing it. Having a conversation and gleaning more information from each other’s different professional backgrounds and creative processes will hopefully help you both improve your craft.

When you’re the kind of person who craves a step-by-step manual for every assignment, it’s easy to write your boss off as uncaring, uninvolved, and uninterested in your professional success. But try to step into his or her shoes and understand where the ambiguity is coming from, and embrace the liberty that’s a part of your manager’s vague tendencies.

From a managing viewpoint, there’s actually plenty of reason to be open-ended and take a hands-off approach—especially when your employee is struggling to take flight for the first time. So, next time your boss tells you to “just throw something together,” don’t overthink it. The trying, failing, and trying again process produces results that he never could have instructed you toward otherwise. And when you do finally soar, you’ll realize how valuable he was in giving you the freedom to make it happen.

Photo of boss showing employee something courtesy of Thomas Barwick/Getty Images.

Updated 6/19/2020