When you need to convince your boss about something, such as upgrading your development machine, the most common mistake you can make is to talk about your problem. You’ll face some situations in which your opinion, your problem, your pain is not really that important compared to all the other issues your boss must deal with. In fact you should never make the assumption that the person you will talk with is going to put your interests before his own. Of course you know many people that will be genuinely interested in your well being, but most of the time, convincing someone to do something you think is good can be very difficult, especially for the introverts. Coming up with a solution instead of the problem alone is not enough. You must learn to focus on other people’s interests and come armed with facts rather than opinions.

Focus on him, not yourself

Focus your argument on your boss’s interests, and avoid mentioning yours. Let’s take the example of the machine upgrade: you want a new machine because your existing one is too slow and you really dislike working on it. Don’t go to your boss and tell him: “I need to upgrade my machine because mine is too slow, it is painful to develop on it”.  If your boss cares less about your comfort than his budget, you will certainly get answers like “Maybe later” or “I’m out of budget” or even “But you are not blocked right?”. Instead, put yourself in his shoes and try to identify what’s important for him.

To help you with that, try to ask yourself how he is evaluated by his own bosses (or customers). How does he report his own performance? In that particular scenario, there are good chances that he will be praised if his team brings new functionality on time and blamed in the case of late deliveries. Your lack of productivity is the pain. Try to tell him: “I need to upgrade my machine because my productivity is really badly affected right now”. Be prepared to get another kind of answer! At best a formal acceptance without resistance but in many cases, a demand for clarification.

Come with facts

Any serious boss will ask for more information to understand your needs and eventually use it to validate their decision. You will certainly meet bosses that use them to cover their own backsides. Don’t wait to be asked for it, and augment your request with facts that demonstrate the real positive impact on the pain you identified earlier. Be sure to use real facts: articles written by an industry authority is not enough. There are good chances that your boss practices critical thinking and coming with blog posts from people he has never heard of will have little effect. For the example we used earlier you could calculate the startup time or the gain in compilation time. You must convert that time into a metric he is sensitive to: money. Multiply the time you save for one or two years by your hourly cost and compare it to your upgrade’s costs. If the gain is real, you won’t have any problem in getting your upgrade.

To increase your chances, be sure that your argument uses simple words to avoid any misunderstanding, especially if you are presenting it to non technical people. Be sure to be concise as well: you would be surprised by the number of people reading only the introduction and conclusion or who ignore any email longer than a certain size.

Formula = Boss Pain(s) * (Real) Facts * Simplicity * Conciseness

More tips

• You should never ask your boss for permission to use a given development practice. Your boss should not impose a way to work on you but should focus on the result instead. You don’t tell the taxi driver how to drive his car. You don’t tell the hairdresser how to cut your hair. You don’t tell a coder how to work with his code. If you think your code needs refactoring. Refactor it. You are the expert, your team should decide what practices you use. Your boss is supposed to decide WHAT to do and more importantly WHY you are doing it. You should take care of  HOW you build it. If you are in the situation where your boss tells you how to work, you should ask yourself if that environment is really good for you.
• If you want to attend a conference, try to compare the costs to formal training courses and be sure to put all the advantages such as the opportunity to network.
• If you need a specific tool, be sure to scan the seller’s website to help you find the facts to make a good case.