Most people, regardless of their age, don’t know how to communicate what they want or need.

This is especially true when it comes to approaching your boss with a request for resources. How do you ask for a promotion in a way that almost guarantees he will say yes? How can you convince him that providing you with more resources such as people, software, tools, etc. will improve the organization?

If you’re lucky, you can walk into his office and start thinking out loud. We all strive to have this kind of strong, open relationship with our bosses.

If you’re still working towards this kind of relationship, there’s another approach that will enable to you have a constructive discussion with your boss about what you need and build a trusting relationship built on team engagement.

Before you meet with your boss about your request, you need to prepare for the ask. A great boss will truly vet any request that comes his way so he can protect the organization’s resources. Show him you respect this by being prepared to have an in depth discussion about the costs and benefits. Not only will you be ahead of the game in convincing him, you’ll impress him by being prepared.

DO YOUR HOMEWORK

It’s important to understand why you’re asking this from your boss. Here’s how to analyze your request from different angles as well as think big picture. After going through this exercise, it will be apparent in your conversations that you’ve given this request some serious thought.

THINK ABOUT YOUR MOTIVATION

You have personal reasons for the discussion and recommendation. List those. Think deeply about what is motivating you and why. Then, think about how will this will help your team. How will your suggestions benefit the boss and the organization?

For some of us, this may be enough. If our motives are self-serving, we may need to wait and reconsider our priorities. Until you can make a business argument, you are not ready for a discussion.

MAKE A BUSINESS CASE

You have a hunch or an educated guess that you are right. Now prove it. Research and find the answers you need. How would a specific software better serve the organization and clients? What value will your suggestion bring weighed against the cost and disruption of change? Be prepared to discuss numbers and figures. Hard data is more convincing than anything else.
Why do you deserve more compensation? Study the facts in the industry. Do you find support for your assertion?

Facts are objective. Can these realities be disputed? Absolutely. Additionally, you should be ready to acknowledge that you may not have all the facts. This may lead you to do additional research.

Doing your homework will allow you to make the business argument that becomes an imperative. After all, this is a business. Make the case that everyone wins with your recommendation and it’s hard for any boss to say no.

SEE THE BIG PICTURE

No one has the complete picture, so work at seeing the whole world of business in your industry. Your discussion with your boss should be informative for you. We suggest that you have strong recommendations, but keep them tentative. Ask for your boss’s point of view and listen carefully. Ask for other points of view as well. Become a big picture thinker. This will help you become more valuable to the whole organization, clients, and even your profession.

Listening is a key ingredient in learning the full story. What are your boss’s priorities? What does he or she care about? What worries complicate the boss’s role? What are the concerns of others in the organization?

STRATEGIZE

Armed with all the data that you have collected, what is your compelling reason for having this conversation? How will you get to “yes”?

You want a promotion. How will this help the organization? Will it create an opportunity for others to advance? Who benefits? How will this help you serve clients better?

You need more feedback. How will this time investment help the team? How will it help you improve your team? How will it help your boss and the organization?

The best arguments for change are well-researched and brief. Combine all of your research into a short, data-driven recommendation and be prepared for questions.

THE ASK

You’re ready for the dialogue with your boss. You’ve prepared your case, so there’s only one thing left to do.

Go into the conversation in a learning mindset.

DISCUSS AND LEARN

Yes, after you’ve done all your research and are ready to inform your boss about this great recommendation, YOU have to listen and learn? That’s right. This discussion will inform your boss, but it will also inform you. As you listen, you will hear and see the reservations and the affirmations. Make this a two-way exchange of information and learn more about your boss. This may be multiple conversations. Most difficult conversations are not resolved in one discussion. You may leave the meeting with specific actions that need to be taken. Your boss may need to gather other information or talk to others. You will learn in this process about your boss’s decision-making process.

FOLLOW UP

Show appreciation for your boss’s time. Avoid sarcasm and disappointment. If you don’t get an immediate “yes”, schedule the next meeting and continue the dialogue. You are learning and growing as an employee. You are taking initiative and becoming an “owner” of your own career and in the end, you are helping the organization grow as well. Your boss will recognize this and see you as an engaged employee with great potential.

Have you ever been unsure of how to approach your boss about a conversation? What did you do to prepare, and how did that affect the discussion and outcome?