How do I deal with a boss who has his "head in the clouds"?

Question

Working with our boss has always been difficult but it's been getting worse in the last few weeks. It seems like he is not paying attention to anything we do or say.

Here is just one example. A few days ago a colleague wrote him an email like this:

At customer John Smith we set up a server and installed our software.
Then we installed all updates. Everything is fine.

His reply to the very same email was:

What is the status of customer John Smith?

As you can imagine this kind of conversation is slowly taking its toll since we have to explain everything a number of times.

Last week he was out of office and he did not read his emails at all. He just called my colleague on his private phone at the weekend and the guy had to tell him everything that was going on in the company. He even asked about the status of things he was supposed to do himself. The hours we spent writing emails were just wasted time. We were told to write daily status mails.

We really don't know how to deal with this. Some people complain about not being taken seriously while some other people complain about wasted time (as they're working on a deadline). Motivation and working atmosphere is going down. I guess if this keeps happening, people will start to leave the company.

Answer 1

Things like this happen in small companies. People have stuff going on in their lives that makes them bad bosses for a while. One of my clients had a very bad year while his wife died of cancer, for example. There was no-one else to carry the weight for him as there might be at a large company.

What can you do? If your boss has a boss, you can ask that grandboss for a meeting. It's possible the company doesn't know what's going on. They can take it from there. But if this is a small company and there is no-one above the boss, you have to decide what to do. You have a couple of options.

What I would probably do is decide he has something big going on in his life (illness of himself or someone close, marriage failure, offer to buy the company, loss of a huge deal causing enormous financial pressure he is trying to hide from you, or the like) and that I will do my best to help. That means sending lots and lots of status emails (as opposed to "what should I do" emails) to try to prevent off-hours rambling phone calls, taking on decisions where it seems I must, and patiently explaining things that shouldn't need explaining. The hope is that by stepping up, the company as a whole can carry the boss through the tough time and afterwards all carry on as before.

Also, the very actions that make things easier for you also make things easier for your boss. The off hours calls are because he suddenly realizes he doesn't know something, and he can't wait until morning to ask, for whatever reason, so he calls. If you just fire information at him as you get it (we just deployed to that customer site, I just got off the phone with X and he's happy, looks like we're getting more work on project Y next week and we can handle it fine, Steve is back from being home sick) then when he wants to know something, it's in his inbox and there's no phone call. Providing full context in every email and including summary lines at the top (Eg start the email with The status of customer John Smith is all on schedule, customer happy, then carry on with details) are habits that will serve you well under normal circumstances as well as exceptional ones. Managing more of your own workload and looking to the bigger picture because no-one is there to do that for you will also grow you as a developer or whatever it is that you are.

Some people wouldn't be willing to work that hard unless they knew it was a temporary situation that "deserved" the help. So if the boss was spiralling into addiction, or the company was going to fail no matter what, they would bail. Such a person should meet with the boss and ask "what's going on?" so they can decide whether to help or not.

Still other people will see the writing on the wall and leave. Get the resume up to date, and adjust what they do at work to support the goal of getting a new job over the goal of carrying this boss through the troubles. That's not a bad choice: if you could run a company as well as this guy, you would probably be running a company, right?

There are more creative approaches, too. For example if you ask the boss "what's going on?" and get a "deserving" answer like a dying wife or whatever, you may be able to suggest getting a consultant to help run things for a year and keep the company afloat. But you would need to provide a lot more detail for anyone here to be able to help with that.

The key, to my mind, is to determine whether anyone can take over for the boss (likely in a large company) and if not, whether you're willing to change your work style to help this situation for a while. It could be very rewarding ... or you could just be the last rat to leave the sinking ship.

Answer 2

Sometimes when people are going through a tough patch at home (illness, divorce, death in the family, etc), they get distracted at work and don't even realize it. In my observation, this is especially true of those people who are trying to keep the issue private (or who are in denial about the issue). It can help if you go talk to him and say something like: "You seem very distracted lately. Is there anything I can do to help?" Don't be accusartory, just say what you have noticed and how can you help.

Now the person may not respond well to this ("Nothing is wrong.") or may break down and tell you the problem or say "I don't want to talk about it." But usually it makes the person realize that others are noticing a problem and that he needs to shape up if he doesn't want people to ask about it.

If you ask him about it and nothing changes over the next couple of weeks, then you can go talk to his boss about it (in a case like this preferably in a group), bring proof of what you are talking about and he can deal with it. But try to let the person know first that you have noticed a problem before you bring in his boss.

In the meantime, just assume something is wrong in his life and give him the benefit of the doubt and give him the support he needs without complaining just like you would want if you were trying to deal with a serious problem. I find it is easier to deal with this type of behavior if you think it could be caused by a personal problem that it is is you just think he is being a jerk.