I am working in a software consultancy company, and our job has a good deal of direct interaction with clients. We are a very international bunch of people, but we are based in Germany, and all our clients are German. From the professional point of view, we not only have to be good technically, but look business-like.
There is a new colleague, let's call him Bob, who is a motivated person eager to work and technically quite good. But he is very timid and quite a nerd - he is not interested in sport at all, his posture is really bad, shoulders sloping, arms always hanging alongside his body and not moving while he walks. He dresses OK, somehow, but the most disturbing is his hair. He hasn't cut his hair for ages, washes it rarely and never combs it, same with facial hair - very patchy beard, and he has a nasty habit of twitching his hairs when he's bored. In short, he looks like a hobo, although in nice clothes.
The boy is actually nice, he is young, new in the city and would like to have friends, one can see that. But I really can't see that shabby look at all, I always avoid him, but we have to work in the same team. He goes to the client with us, and I am ashamed of the image we produce as a company when he looks like that. I also think that if he changed the way he looks and realized that he can look much more likeable, it will also help him feel better about himself and get more friends.
I have noticed that most of the questions in this forum can be answered by very direct communication. It's that easy. But unfortunately it is not an option in this case. If I talk to Bob, even very nicely, he will definitely just get offended, and that will make our teamwork worse. My colleagues agree with me about his looks, but no one wants to talk to him in fear of him getting offended. I have already talked to my boss who also said it would be weird if he as a boss did it, then poor Bob will get scared to death. The boss presented me with an option to talk to one common colleague who works remotely, let's call her Alice, she's a very friendly lady and they are almost friends with Bob since they started together - the suggestion was to ask her to play a role, telling Bob that she has a couple of girlfriends who would like to meet new people, but before she can organize a meeting for him with them, she would like to go to a hairdresser's with Bob and pimp his style. Although the idea is interesting, I seriously doubt that Alice will be happy to do it, and that it might work at all.
So. I understand the easiest option would be for one of us to talk to him. The question is, who and how. Let's try to get creative here. As I said, being direct will damage our communication. I would normally be very direct, but that does not always work for all people. All of the other colleagues I see take care of how they look, and I want this one to do too, I want to have a pleasant team, have a good image before the customer and maybe help this guy understand it's nicer for everybody if he takes care of himself.
What's the best way we can ask/motivate Bob to clean up his hairstyle?
Edit: Information collected from comments:
My boss agrees that the guy looks bad, and that it would be better if something was done about it, but he himself is indecisive for now how to handle this.
Our HR department is kinda "separate" from us and the decisions about hire are mostly made by our technical employees, so they won't help us in this case. We generally strive to have a "family" atmosphere in the company, we are relatively young, but growing fast, and it's becoming hard, but we are trying to leave it like that and it's of utmost importance to our boss, that's why he said it would be inappropriate for him to do it.
I understand my boss as a person, but I guess as a boss he is still probably the most appropriate person to do it. I don't think he thinks this as important. But he does not work with Bob. I agree, this is not something that will ruin the entire career of our company, but for me as a team-member it is something I would really like to change.
We are actually going to have a "review" meeting about assessing the job we do in a week or so, just came to my mind it could be a good time to mention this. Review is going to be done by the boss and one other colleague.
Alice once asked him why he wouldn't trim his hair and he said something along the lines of "I'm too lazy".
I have had a couple of talks with different colleagues, they understand me and some of them also get frustrated because of this, the HR department also complained to us this is inappropriate, but the customers Bob works with so far haven't worded anything yet. He might be transferred to other customers soon. The managerial part of the company have decided they will leave this as it is until the customers make remarks - then this will definitely be addressed. Meanwhile, the guy who manages Bob's work has somehow taken Bob to a sports facility and has a plan to go to a hairdresser's and take Bob with him=)