9 out of 10 monkeys believe they are not behind glass

Always a fun topic for me since my boss needs plenty.

From here:

I’ve worked for huge corporations and tiny firms, and whenever I switch from one to the other I have to do a certain amount of unlearning and re-learning when it comes to social habits.

With a corporation, you should only tell your boss about success you’ve attained or problems you need him to solve. This is because corporate managers deal mainly in delegations, introductions, and schedules. If you tell a corporate manager about a problem only you can solve, he/she will think, ah, they’re telling me about a problem they have, I don’t know how to solve it, so I’ll delegate this to XYZ person. Then you end up with XYZ person tripping all over the problem space, trying to figure it out, while you try to implement the solution.

You could have thought, aha, here’s my manager, I’ll just keep them up to date, but if you don’t keep them up to date in the right way, your schedule could be compromised by their very attempt to help. Many people respond to this by blaming the manager, but that’s because the tech culture has a very irresponsible attitude towards communication. If you’re on schedule, you say something to somebody, and now you’re off schedule, that’s your doing.

Now conversely, with a small business, you need to justify your time. Small businesses are more budget-conscious. This is true even for prosperous businesses on expensive projects with well-funded clients; it’s not a matter of being on a budget per se, but of focus. Large corporations aim for economies of scale. Small businesses aim for efficiency. This is why innovations always come first from small companies. It also means your client or manager will need a different level of detail.

Small companies also have much smaller social networks, so your higher-up will not be thinking in terms of, is this under control or do I need to do some delegating or make some introductions? Your boss, or client, or whomever, is going to be thinking more in terms of, is this done, and how long will it take, and what steps remain? (Also, if you charge a hefty rate, your client may want to be sure you’re not doing anything simple or basic that they could offload to one of their more affordable people.)

It’s important to keep this in mind. Talking to a corporate manager the way you talk to a small business owner results in the corporate manager thinking you’re overwhelmed and don’t know what you’re doing. Talking to a small business owner the way you talk to a corporate manager results in the small business owner thinking you’re self-important and wasting time. (And this is, of course, assuming in either case optimal corporate managers and optimal small business owners. Any dysfunctions in either case can of course mean further compounded communication errors.)

And from here:

1. Meet your boss’s needs. This is the first and most important key to getting to “yes.” Everything else in this article is a footnote to this point.
2. Pick your battles. I have a basic rule when it comes to pitching my boss: I don’t take a swing unless I am confident I will hit the ball. I would encourage you to do the same. Don’t make the pitch unless you intend to make the sale. Your credibility as a manager is at stake—with your boss, your peers, and your direct reports.
3. Do your homework. I’ve already mentioned this in passing, but it is worth repeating here and amplifying. In my experience, this is the number one reason why people don’t get to “yes.” They simply haven’t thought the proposal through. As a result, it is full of holes. Each of these provides an easy out for the boss and a quick “no” for you.
4. “Bullet proof” your proposal. This is where the battle is won or lost. Unfortunately, it’s a step that most people skip—to their own detriment. Spending 30 minutes working on this is the best investment you could make.
5. Make the pitch. Schedule a time to make the pitch. Pick a time when your boss is likely to be the most receptive. Has it been a bad month? Don’t schedule an appointment right after he’s likely to get the news. Is he more alert in the morning or the afternoon? Use some common sense and try to schedule the meeting when you have the best chance of success.
6. Accept responsibility for the outcome. When I was further down the food chain, I used to hear my peers constantly complain about how unreasonable their boss was or how bureaucratic the company was. Blah, blah, blah. They had a thousand and one excuses for why they didn’t “make the sale.” Few of them were willing to accept the fact that their proposal just wasn’t that compelling. Their presentation skills sucked, and it was easier for them to blame someone else rather than accept responsibility for the outcome. As a result, they missed the opportunity to improve their skills.