5 Signs Your Boss Is Insecure | Proposify

5 Signs Your Boss Is Insecure

When someone says they work in advertising or design, everyone expects to hear exciting tales of last-minute pitches and late-night brainstorming that change the face of marketing forever.

5 min. read

More often than not, it simply results in an idea that sounds like a game-changer when downing that final pint before last call, but in the cold, harsh light of next morning, it looks a lot like an idea two tired drunk people came up. It may involve boobs, a corny tagline and a bengal tiger thrown in for good measure.

Too many times though, poor leadership is responsible for an agency staying in the safe zone, resulting in work that might get sold to clients, but never gets noticed by the creative community as a whole, or worse yet, their clients’ audience(you know, the whole reason they hired an agency). That’s because the agency owner insists on retaining creative control and filtering the great ideas — despite the fact that he has zero experience producing great ideas.

An insecure agency president is incredibly deflating for creative people, and once you recognize him, the key is to cope — to offset these traits by sheer avoidance, direct conflict, or comic embrace. Remember, this is your job so you might as well make the best of a bad situation.

Here's what to look for, and ideally to enjoy, as you witness your absurd superior stumble on a daily basis:


Audi. Saab. BMW. Mercedes. These are vehicles that inspire middle-aged dudes the world over to rack up debt just to impress clients, employees and women in nightclubs half their age.

It's a cliche' for a reason. Simply put, because he's not that good at running the show, he's gotta be good at something. Such as driving the best car at the agency. Bells and whistles mean everything to this guy, and his car is loaded with them. A friend of mine once told me that his boss moaned about the fact that an employee drove a better car than the boss. Obviously this was a window into his insecurity; He needed an outward symbol that proved he was the smartest, most successful guy and the top dog at the firm.

How to cope:

There’s two ways to handle this situation. One way is to sycophantically compliment him on his amazing erection on wheels. The other is relieve yourself in the back seat when he’s not looking and blame it on a passing hobo. I’d say go with both options.

I knew he was planning something shady the minute I read his cardboard sign.


Have you ever seen a grown man dressed way out of scope for his age and his place in society. Yes, admittedly, this is sometimes the sign of a person who is very confident and comfortable in his own skin — and in some instances, the sign of a genuine trendsetter.

However, many of these guys just look like idiots: $300 button down shirts that are way too tight, jeans with that intentional faded style to imply they care so little about how they look they visited seven stores to find them, inappropriate sneakers better matched with a skateboard and, as the worst offenders, fedoras.

How to cope:

You could make a point to “notice” that new pair of leather pants he’s strutting around in, but that plan could backfire (they’ll only get tighter next week).

That’s some high-quality knit work. Where’d you buy that from?

Taking over creative

This one's obvious, but needs mentioning. Confident leaders hire people than smarter than they are and trust them to make them a lot of money.

An agency president who is filled with self-doubt usually doesn’t want any idea coming from his agency unless he came up with it. And if your idea is truly better and has the team excited? He’ll use that one little phrase that ruins everything, ‘let me play devil’s advocate for a minute’.

How to cope:

Wait for his next trip out of town or late night bender to push good work out the door before he has a chance to come in and change everything.

I did this once before, and it was some of my best design work. My account manager and I quickly got the idea and execution sold to the client, and my boss was clearly irritated that he didn’t have a chance to “give his input’. The client was happy, it had a positive impact on their sales and got some local and international recognition, but ‘he wouldn’t have done it like that’. Too bad.

Last-minute Delegation

An effective agency prez can either do it himself, or know how to pass it off to someone more skilled in a particular area. The insecure prez, on the other hand, will only delegate when he knows he's screwed. An example? How about a creative presentation?

Monday: "I'll take the lead on Thursday and run the client through everything."

Thursday morning on the way to the meeting: "John, fill me on again on what this is all about. Oh crap, it's about back-end stuff? Okay, you run with this. I'll just nod a lot in the background after introductions."

Thanks for the leadership, boss. Hopefully, we'll pull through again and win you more awards this year.

How to cope:

Always be prepared to handle the presentation so when the inevitable happens, you’re ready.

False Brilliance

Someone who's good at what he does rarely has to say it out loud. Not the case with the insecure agency boss. He's fucking brilliant, and wants everyone to know it. "Hold on, give me a moment to dwell on this," he'll smugly boast, "I'll be sure to come up with something."

And usually, his "something" is either total shit, or a good idea stolen from an advertising annual.

The insecure boss also loves quoting agency heavyweights to establish more credibility for himself, and because he wants to believe that he's in the same company as them. "Leo Burnett used to say that a great idea is…" Or, as a more recent example, anything from a hip and popular author, specifically Malcolm Gladwell.

“How would David Ogilvy sell these snow peas?”

How to cope:

Smile, nod, take a sip from your travel mug of rum. Then try to look inspired.

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