Armchair analysts, take a shot in the dark!

• My boss is a very nice man with some very strange shortcomings that I cannot explain. Help me out with some wild conjecture. I work in the media industry as a designer. My boss is a very sweet, emotional, sensitive and kind man. He is very positive and upbeat, and easily gives praise. There is not a malicious bone in his body and I like him very much as a friend. But as a boss, working with him can be very difficult. I've been puzzling over the reasons for his sometimes odd behavior for months. The biggest problem I have with him is his seeming inability to relay a message correctly. Clients will tell him why they don't like a layout, for example. "We don't like the guy with the hat in the corner. He looks too formal." He will come back to our design team and say, "No guys with hats, get rid of that guy, he has a hat", when in fact, the guy in question is perfectly acceptable. So we'll get rid of a guy from a photo who we could have used because he did not relay the gist of what the client said, just the most superficial level of it. It's gotten to the point where I never trust anything he says when it comes to relaying information, because it's almost always either fractured or outright wrong. You have to be able to grasp nuance to communicate to your designers, and since most of us never get to meet with our client, this makes our job very difficult. He often misunderstands instructions and has on several occasions told me the incorrect deadline, or misquoted someone. When I double check this information, the person who was misquoted or who gave the deadline professes confusion, and we discover that it was my boss who gave the incorrect information. As far as I can tell, he is not hard of hearing. Or someone who barely even knows us or our company will mention, "I hear your company is going to lose XX% of its workforce". And instead of thinking back to last month when we lost XX% of our workforce and realizing that the stranger is clearly referring to what has already happened, he immediately assumes that something is being hidden from him, and panics that we're all going to lose our jobs. He has very low standards for work, and usually approves the first thing that lands on his desk instead of pushing anyone to do better. He will bring up what he perceives to be a problem, "This layout has the blonde in front, don't you think she should be in back?" and when you try to explain your point for putting the blonde in front, instead of listening to your reasons or pushing his own point, he says, "Ok! Got it, just thought I'd ask" and walks away. All of this I could understand better if he were unintelligent, but he's not. He is very earnest and sincere, but he also has a dry wit and it's always a delight to be at the butt of his affectionate jokes. To try and fill in the picture more, he is very nervous and takes some kind of medication for his nerves. If not Xanax, then something like it. So why does this charming, lovable man have such a problem with communication and translating the thoughts of others?

• Answer:

  I work in the creative services industry and this is very common. we tend to have account executives whose only job it is to transcribe any wishes a client may utter (aka. keep meeting minutes) and make sure deadlines and briefs are being addressed. they're often dismissed as suits who carry your presentation and laugh at the clients jokes but this schmoozing can make a world of a difference. have an AE who the clients likes and who gets how the client thinks and you'll have a way easier time selling your work. the only problem is that AE's will constantly try to run the ship because all they care about is how much money is being billed on their watch (which means caring about the client being happy regardless of how idiotic a wish might be). I am certain you already have someone whose job it is to deal with administrational duties relating to the client in your company (writing invoices, proposals, following up on calls). have that person write down exactly what the client said they wanted and when. let's talk about your boss. unfortunately he is ill-prepared for his position. he lacks maturity and experience. I see this all the time. I have well-liked and absolutely nice guys on my team but they still need supervision. I had a person the other day who said she could do something and when I checked up two hours before the presentation the work had been performed sub-par. I would love to make this nice person a manager but she demonstrates with behavior like that that I still need to check her work. your boss is just like that. he hasn't learned to be diligent yet. he hasn't learned to listen closely and check every last dot no matter how bored he is. that's an experience issue. you need time to figure out what matters most and nothing but time can help you get it. I doubt he will be able to improve quickly. the "not pushing you" part is trickier as it hints at a lack of professional knowledge and -in this case- passion for design. apparently he doesn't realize what you are capable of. does he not have a comparable education? does he not have the drive to grow? smart managers surround themselves with people better at certain things than they are and if he doesn't dream of producing something better than he could do himself I'd question his motivation. what is important to him? does he come over to your desk to show you the latest cool website or book or is he proud of the latest earning reports? (neither is bad but look at what matters to him personally and you know what matters to him professionally.) finally let us talk about possible solutions: (1) his behavior suggests he does not enjoy talking to clients. you should try to be the one who talks to clients. offer to come along to a client presentation and help out. there will be an opening somewhere. prepare as much as you can and shine. make sure the client loves you and make sure your boss realizes on his own you're capable of making him look good. a basic but good trick is to begin your presentation with "I thought about X you said last time and it got me thinking about a solution like Y..." do this right and you will end up seeing this client alone and -eventually- be trusted with presenting to other clients by yourself. I have two young guys on my team who I know I can send to clients on their own without having to fear they might embarrass me or the company and they are quickly becoming my go-to guys when I'm stressed. (2) he might in fact be stressed out. do you think he has too much on his plate? if so, what could you take off his shoulders? the less one has to concentrate on at the same time, the more focussed one can be. it's just like sending a text message while driving. (of course he might have problems other than workload. don't try to be a psychiatrist in that case.) (3) consider other options. this is the nuclear option. if your boss won't let you grow, if he turns out to feel threatened by your help, consider changing jobs. if it's time would be a different ask.me question, so I won't elaborate here, but it should always be on your list of possibilities.