It pains me to write this, but my first question about your boss is this: is he taking the time to talk with you in a private setting? A 1:1 is a frequent, regularly scheduled meeting between you and your boss, and if it’s not happening, I, uh, don’t really know where to start.

A 1:1 is a time for the person who is responsible for your professional well-being to check in and see how it’s going. Yes, a 1:1 is a time for team and project status too, but I’m certain that information is bouncing around elsewhere in the company. A 1:1 should, on a regular basis, involve a frank discussion of how you are doing professionally.

There are large and successful companies like Google that have stunningly large employee to manager ratios, which means there is no practical way for regular 1:1s to occur. My question is, “How are these employees growing?” Yes, there’s a world of experience to be had writing your code, arguing with Felix the QA guy, and working 27 hours straight to hit a deadline, but there’s free and hopefully painless valuable experience sitting in your boss’s brain right this very second.

One of the hats your boss should wear is that of mentor. He’s likely seen more than you, which means there’s a high likelihood that you can bring any random question, idea, or disaster to his desk and he can comment...hopefully valuably.

The absence of a 1:1 is the absence of mentorship, and that means your need to gather your experience in the trenches. And while there is nothing to replace “real-world experience,” I’m wondering what the value add of your boss is. If he’s not taking the time to pass on what he’s learned, isn’t he just a project manager?

If you don’t have a 1:1, ask for one. Maybe it’s not every week, maybe it’s once a month, but it’s an essential time to reflect on your job and career and to plan.

Your boss’s appetite for information can be discerned by how he runs his staff meeting. By understanding how he constructs and runs this one meeting, you can get a good idea of how he wants his information presented. I have a spectrum that I use to assess engineers that also applies to managers. They’re either organic or mechanic, and I’ll describe each briefly.

An organic manager uses the word “feel.” A lot. He understands the personality makeup of his team because, of course, he has 1:1s. He wants to know how you feel because he understands that the messy parts of being a human being very much affect his team and his projects.

The mechanic manager understands the world through structure. Like any typical geek, his interaction with the world follows the mental flowchart of “how things work.” The mechanic manager values predictability, consistency, and facts.

With that brief description, let’s see how these personalities define a staff meeting:

Understanding whether your boss is organic or mechanic is directional, not definitive, data. I’m organic with mechanic tendencies. Your boss is also a mix of both, and different aspects of his personality are going to manifest depending on different scenarios. My last boss was intensely organic until senior management started to lean on him, and then he went completely mechanic.

Your job if you want to communicate with your boss is to figure out his particular mix and how he uses it.

You don’t really need to worry about adapting to or shaping your communication style for a primarily organic manager, because he’s willing to adapt to whoever you are and how you communicate. The organic gets people and, as such, will deftly manage the conversation towards the information they need.

Mechanics need structure. Mechanics need predictability. I had a manager who was so mechanic that if I changed the order of my 1:1 updates, he became visibly flustered. “We talk about people before products, right?” You don’t wing it with mechanics. You tell them what to expect, deliver, and then confirm the delivery.

Contrasting communication styles are a hindrance to the ability to effectively communicate. Mechanics think organics are frenetic babblers. Organics think mechanics are passionless automatons. We’re both wrong.

If you happen to be on the other side of the communication chasm with your boss, remember that it’s just as much his job to build the bridge as it is yours.

Over my career, I’ve gone back and forth on the value of status reports. The mechanic manager in me loves the weekly structured rhythm of ascertaining and communicating your week. My organic tendencies remind me that if you’re relying on a status report to understand what’s going on in your organization, you’re probably hiding in your office too much.

The presence of status reports is a sign of a mechanical manager, and it might not be your boss, it might be his boss, but that’s not the interesting data. Let’s assume it is your boss who is asking for status reports. What do you learn?

My impression is that the presence of status reports is an indication that your boss doesn’t trust the flow of information in your organization. I’m not talking about paranoia; I’m talking about unfulfilled information acquisition needs. Your boss sees the status reports as a means of filling a perceived information vacuum.

The question you need to answer is: why is he seeing a vacuum? Maybe he is intensely mechanic and doesn’t have the social skills to gather the data in the hallway. Maybe status reports are just the way he’s always done it, or perhaps he’d prefer more data in your 1:1?

If status reports are a corporate mandate from on high or just part of the culture, you’re likely stuck with them, and I say embrace it. A good status report doesn’t read like a passive-aggressive, boring bulleted list. It’s your chance to write what happened this week, why it matters, and what’s next.

If the status report is just being requested by your boss for no valuable purpose, your job is to kill it, and you do that by determining what communication gap he’s trying to fill.

I’m heavily pushing direct human-to-human communication because while status reports might be structured and reliable, nothing compares to the understanding you gather when you look someone in the eye.

Another good way to assess your boss’s information appetite is to look at the meetings he schedules outside of 1:1s and staff. I’m not talking about the meetings he attends, I’m talking about the ones he takes the time to schedule either on a regular basis or as one-offs. These are not the meetings he has to attend; these are the ones he wants to attend.

There are two classes of meetings you’ll find:

In your scheduling assessment of your boss, you’re less interested in a single meeting than in the meeting aggregate over time. You need to step back and look at two weeks of boss-scheduled meetings. Lots of technical meetings? He still thinks he’s an engineer. Alignment meetings everywhere? Your boss is attempting to reconcile differing opinions somewhere in the building.

Conventional wisdom is that when you become a manager, you’re going to forego the technical aspects of your career. Let those closest to the bits make the hard decisions. But I think there’s a balance to be struck here. A totally technical manager won’t see the larger project landscape and will stumble when tricky people-based issues get in the way, whereas a project-focused manager has likely forgotten the basic rules that motivate engineers.

In your meeting assessment of your boss, like organics and mechanics, you’re looking to see where they land on the technical/alignment spectrum because you want to know what they need to hear. Are you bringing in the technical minutia or the project details?

If everything is working, your boss can get everything he needs to know from you, his boss, or his peers. However, “everything working” is rarely the case in companies. Information moves at different speeds in the company based on a dizzying number of factors that we’ll talk about in the next chapter. And there will be times that your boss will, inexplicably, put his hand in the cookie jar.

The cookie jar is a metaphoric representation of when your boss crosses an organization boundary that he shouldn’t. The classic cookie jar move is when a senior manager bypasses one his direct reports to talk to one of their direct reports. There are perfectly acceptable reasons for this manager to make this request, but there are equally many ways this can screw up team communication and morale.

I’ll explain. Senior manager Frank has a manager named Bob who has a bevy of employees, one of whom is named Alex. One day Frank is frustrated that a bug hasn’t been closed in Bob’s group, and Bob is nowhere to be seen—virtually or otherwise. In his frustration, Frank goes straight to Alex, who owns the bug, and asks what’s up. Alex happens to be all over this bug and has proven it’s a user error and is happy he’s able to instantly defuse Frank’s frustration. Everyone’s happy, right?

In isolation this is fine, this is a team of people communicating, but now Frank knows he can get instant bug gratification from Alex, and Alex knows he did a solid for the big boss. My question is: where the hell is Bob?

Maniacal rules regarding the chain of command are the domain of the military and don’t belong in software development, but the organizational chart, and the manager and employee relationships, exist for a reason. These relationships define who is accountable for what. The precedent that is unintentionally set by a cookie jar violation is that it isolates people who should be in the know.

A cookie jar violation can occur in any direction on the organization chart. It is the act of deliberately circumventing individuals from the flow of information and decisions, and if your boss is a cookie jar violator, he’s either not getting the information he expects or he doesn’t understand how teams of people communicate.