Anything helpful to do for a socially challenged superior?

Question

I've been in this situation in the past and it might not have been the last time (working in the tech industry, I've seen this type of behaviour also from other peoples' superiors). So I'm wondering whether there's anything useful, helpful, and/or kind to do when confronted with (such) a socially challenged superior - other than or in addition to following SO Workplace Rule #1: Get a new job!

Let me explain: I've had this boss (CEO) who had trouble picking up on cues on his employees' emotions (in particular "negative" emotions) and requests for support. A partner company failed to deliver an important dependency for the third time in a row and a colleague was angry about it and asked for support? "Well, nothing much we can do about it..."

As far as I can tell, this was never malicious - he just didn't notice or grasp the relevance of the problem. Or if he noticed, it was with a delay of months, when the anger at being ignored had already built up, leading to fights with completely frustrated employees and - in at least one case I know of for certain, possibly more - to an exceptionally productive, valuable, kind, and helpful employee quitting in anger. At which point the boss was surprised by the anger and distrust he received and didn't know how to handle the situation.

This boss had a... let's say: very focussed working style - focussing on one problem/project at a time (for months) and disregarding most other issues/projects, which, accordingly, started piling up. When notified of these issues, he'd discard them as unimportant until he couldn't any longer, which, again lead to frustration for his employees, who were then called in to put out the fires.

Also, he had a taste for the path of least resistance, meaning that in frequently the person kicking up the biggest fuss would get their way.

Now, in my eyes that's not a way for a boss to behave. But attempts at discussing some of these issues were - again - mostly discarded or talked down. (Besides, there are so many ways a discussion about "Your management style needs improvement NOW!" can go wrong...) Sometimes there was a short-time improvement but since it took him a conscious effort to uphold, everything reverted back to (un)normal when he was under stress again. (And he was good at creating stress for himself.)

I had a strong feeling that this whole mess stemmed from some sort of mental issue or other. But I'm not a psychiatrist and going around armchair-diagnosing your boss doesn't bode well for your career and isn't respectful.

However, since he was a well-meaning, friendly, helpful, even charitabl eperson (when not completely oblivious to others' feelings - I know this sounds weird as hell), I wonder if there was something productive and/or kind I could have said/done for him to improve the situation. Because not only was it difficult for the employees, it was also unpleasant and stressful for him, and it cost him in talent and motivation.

I'd like to hear in particular if you've been this boss in the past and found a productive way to deal with it. Was there a book or other resource that helped you? A metaphor that you understood and lead you to change something? An event that took place? Something that may have been a small nudge in the right direction to lead you to a happier path?

Or did the happier path come about simply because the naysayers quit and you could finally work without being interrupted by all these useless discussions?

Answer 1

I'd start with a copy of Dale Carnagie's "How to win friends and influence people".

Rather than give an amateur diagnosis of some PDD, let's attack the issue at hand. Thomas Edison, Stevr Jobs, and a few other CEO types, especially hands-on types tend to be absorbed in the work itself, and hate to be bothered with what thy consider details.

The best way to address this is to be the squeaky wheel. If can find a very diplomatic way to pester him with pressing concerns, he'll take the path of least resistance and address them. That's how you can support him.

If he starts to get annoyed with you, reply in a very logical manner that you feel that you are doing your best to catch concerns before they become issues that will require more to address.

Answer 2

I worked for this guy more than 30 years ago. It can be frustrating, I know. But in the long run it was really good for me and my career to have this kind of boss.

I am sure you are asking why at this point. It was good for me because the tactic we had to take was to make almost every decision ourselves since he didn't want to be bothered with details. As a result as a very junior management analyst, I was taking on the tasks of a much more senior manager. I determined the tools and techniques we used, I determined the schedule and budget, I determined the technical regression equations we ultimately chose to use and I organized writing up the results (as document that was over 100 pages long and very complex to put together). I got several promotions out of having an incompetent for a boss. I got to do much more interesting projects later as well since I accomplished a lot when working for him.

So this is what I recommend for you. First accept that he is who he is and he is not going to be what you want him to be. This is usually the hardest part!

Next, start deciding what things you are currently trying to get him to do that you could do instead. Then start doing them and just sending him information about what you chose to do.

For things that must have his attention, then create everything he needs so that he just has to sign off.

Let's take an example of a 3rd party vendor who needs to be fired. First you get a copy of the contract and highlight the applicable clauses he is not meeting. Then you write up a document with dates and times of the problems that meet those conditions. Then you have a lawyer write up the document that he will sign to terminate the relationship. Do some research to find a different and better vendor and have the contract for that person (or to advertise for bid) made ready as well. Then you go to him with everything all prepared, have a meeting to explain the problem and the resolution and give him what he needs to do the task right there in the meeting. THe key is to make it easy so that he can do what needs to be done right in the meeting.

If the issues is that he needs to talk to someone in person, then set up two meetings with him, the one to talk to the person necessary and the one to brief him on what needs to be said. Again prepare any materials he might need in writing to have as reference during the discussion.

If he balks at resolving something that should be his call, then stop him immediately with "Bob, this is a showstopper. We can't meet the deadline unless this is resolved. If you don't want to try to personally resolve it, then the only other option I have is to ..." Then get his permission to do... but don't leave the meeting until either you or he is ready to take action. And tell him flat out the seriousness and the feelings of anger about the issue. This is not a person who will take a hint. So don't even try to hint.

Answer 3

So he has problems picking up cues that are visible to most people. Make it easier for him. Write a sign "mildly angry", another one "angry", another one "very angry", and when you talk to him while being angry and you want him to know, show him the appropriate sign.