When and how is he most approachable?

This seems like a simple question, doesn’t it? Yet there is a great deal of insight to be gained by studying when and how to approach your boss. Like all managers, he has a particular style of interacting with his team. Some bosses are informal; you can talk to them anytime, anywhere. Others are more rigid and process oriented. The key is to figure out his preferred interaction style. For instance, can you knock on the door and get a minute of his time? Has he declared his preference about the office popin? If not, ask him directly: Are you open to me coming by your office with a quick question, and if so, when is the best time during the day? If that doesn’t work, ask one of your peers or just pay attention to the pattern of when you’ve been most successful. I once worked for a boss who literally wouldn’t allow the “do you have a minute” request—you had to set up an appointment to ask a simple question. Believe me, I wasted a lot of time and energy before I figured this out, and was getting worried that he didn’t like me. But it really had nothing to do with me. It turned out he preferred to read and prepare for any discussion and didn’t feel equipped to make decisions in informal conversations (this single insight explained a lot about this boss, by the way).

In today’s world, understanding his approachability means knowing when to call, text, or instant message, too. The same principles apply—when is he most approachable, and what are his preferences? Some bosses prefer e-mail over phone calls; others want to talk directly if possible. Some bosses text; others won’t. Some bosses are accessible when they are out of the office and others aren’t. You get the idea. It’s about knowing when and how. But it’s also about knowing why.

Understanding why is what helps you make sense of his behavior. I recently coached Tanya, who was experiencing a huge disconnect with her boss. She kept trying to call him directly, and the boss always refused to take her call; the boss’s assistant would just say, “Send him an e-mail.” And of course, whenever Tanya did that, she received a prompt, thoughtful reply. Strange, I know. Wouldn’t it be quicker to just talk on the phone? Of course, the boss never explained his motive, which drove Tanya crazy; she was convinced the boss thought she was a poor performer. Now, as it happens, in my feedback process, I learned the boss wanted a written record of every interaction. He didn’t like the phone for even the shortest conversations because it didn’t allow for a trail of detail or evidence. Was the boss anti-social? Almost certainly. But the real motive behind his interaction style had nothing to do with that; rather, it was based in a more practical (some would say paranoid) reason. This is a perfect example of the value of digging deep to gain an understanding of the core motives behind your boss’s behavior. The “why” isn’t always what it seems to be, and much of the time, it isn’t about you at all.

The second thing you need to study is his mood pattern. What puts him in a good mood, or conversely, a bad frame of mind? What day of the week is he most approachable? When should you leave him alone? Is he stressed right before a meeting with his boss? Do certain events or deadlines impact his approachability? Try this exercise: For a month, make a daily diary of his moods. Name the mood (angry, happy, sad, etc.) and note how approachable he was each day. Then, study the diary to learn your boss’s patterns and work around them to your advantage.

Third, how much can you challenge your boss in group settings? What style of interaction works best? Is he open to rigorous debate? Most managers hold staff meetings with their direct reports, and there are unwritten rules about challenging the boss’s ideas, how long to debate an issue in front of the team, etc. Do you know where this line is with your boss? Have you ever crossed it?

A lot of bosses are resistant to anyone disagreeing with them in public, and it can take a while to learn that. One of my clients, Craig, was getting frustrated with his boss’s staff meetings because no one would challenge the boss’s ideas. As Craig tried repeatedly to push back on his boss (with respect), he made things worse for himself because the boss didn’t tolerate or appreciate this interaction style. Craig learned to discuss these issues outside of the meeting format, but it took some reflection about the boss’s motives to recognize and make this shift in his approach. The trick is to pay attention to the small signs if you find yourself in a non-productive public conversation with your boss. How is he reacting to you? Study his body language and tone of voice. If you’re pushing his buttons, find a gracious exit to the discussion.

Finally, you have to know what subjects are either allowed or out-of-bounds for your boss. What are the topics or questions you can raise, and what are the sacred cows? Where can you probe, and what should you leave alone? There are some issues you shouldn’t approach him about; and if you do, he won’t talk about them anyway. For years, I tried to get a boss to talk about his life outside of work. He wouldn’t do it. I’m an open person, so I thought that was odd—why wouldn’t he share what he did on the weekend? It was really bugging me. He would talk about sports and current events, but not about his hobbies or family. Finally, I realized I wasn’t going to break through that wall between work and home, and stopped asking him. I accepted that I wasn’t going to change him. If he wanted to keep certain things private, that was his choice; he didn’t have to be just like me. And you know what? Once I stopped worrying about it, our relationship improved.

The bottom line is that you need to be thoughtful about approaching your boss. He wants you to fit his interaction practices, not create new ones. Every time you push him out of his comfort zone, you risk annoying him. How many minor irritations are you willing to add to your ledger? The easier path is to adapt to his style by learning exactly when and how he is most approachable. Then, work out the rationale for his preferences so you understand where he’s coming from; there might be an underlying (albeit quirky) reason that has nothing to do with you. You may not like it, but at least you’ll understand it.