Relationships
How to Earn Custom Rewards at Work
"Do business" with your boss to earn the rewards you want.
Posted December 14, 2021 Reviewed by Gary Drevitch
Key points
- Identify what discretionary resources your boss has available, and concrete ways to earn them.
- Do your part to help your boss clear custom rewards with HR.
- Consider what isn't negotiable, to better leverage the aspects of your performance which are.
- Don't underestimate the power of formalizing requests in a proposal.
If you want a custom deal at work, you need to know what discretionary resources your boss has at their disposal and help them help you get access to more of them:
- Money and benefits. How much of your base pay is fixed? How much is contingent on clear performance benchmarks tied directly to concrete actions you can control? What is the value of your benefits? What are the levers you can pull to drive your own compensation up?
- Schedule. What is the default work schedule? How much flexibility is there? What levers can you pull to earn more scheduling flexibility?
- Relationships. Who will you be working with? Which vendors, customers, coworkers, subordinates, and managers? What levers can your pull to have more control over who you have a chance to work (or not work) with?
- Tasks. Which regular tasks and responsibilities will you be assigned to do? Are there any special projects? What levers can you pull to get more opportunities to work on choice tasks, responsibilities, or projects?
- Learning opportunities. Will there be any special learning opportunities? What levers can you pull to access more learning opportunities?
- Location. Where will you be located? How much control will you have over your workspace? Will there be much travel? Are there opportunities to be transferred to other locations? What levers can you pull to control your location?

The key here is to ask yourself: What can you do to earn more? What hard work can you offer? What extra efforts can you make? What value can you add? What leverage do you have? What can you bring to the table as a bargaining chip to earn more of those discretionary resources? Make sure that the boss feels as if they are getting a very good bargain—that they will end up being delighted to have made a special arrangement to reward you, because you are delivering so much value in return.
Look out for really tough assignments—special assignments—and roles that are hard to fill. Look for ways you can save your boss trouble. Think of these stretch opportunities as your chance to prove yourself and make a huge investment in your career and build a professional reputation.
Be Realistic
You have a right to expect to be recognized and compensated for the work you do. But you don’t want false hope or false promises. If your boss thinks that what you need and want from the job is unrealistic, you want to know that immediately so that you can adjust your expectations. You need to figure out how to “do business” with each boss.
“If you want a helicopter…that’s just not going to happen,” one manager in a non-profit community service organization once told me. “But if you want free memberships for your family members, that’s no problem. If you want to leave early to visit your sick nephew, that’s no problem. When employees cooperate with me, I cooperate with them. I can’t do everything for everybody all the time. But I will do what I can for you, especially if you are going out of your way to help me out when I need you.” Small, one-time accommodations are among the resources that managers do have available to them. “If you want to be on the receiving end of those accommodations, you have to do your part to put me in a position to help you.”
Maybe your boss lets you come in a little late or make personal calls from the office because you are otherwise valuable and there are not a lot of discretionary rewards available. If you think your boss intends those accommodations as a small reward, mention them. Ask whether you have interpreted the situation correctly. Definitely say, “Thank you.” Whatever it is, make the quid pro quo explicit. Reassure your boss that you know this custom deal is not to be taken for granted, and remains contingent on your continuing to deliver on your part of the deal.
Everything Is Negotiable…Almost
Employment relationships are transactional by nature. If you want special rewards, find out every step of the way exactly what is expected of you and what you can do to go the extra mile and earn extra rewards. Will there be bonuses for early delivery or exceptional quality? Penalties for late delivery or work that fails to meet expectations? The ideal bargain is one that clearly defines the deliverables expected and has a concrete deadline for delivery, along with specific milestones that need to be reached along the way. Every penny of compensation—financial and nonfinancial—would be tied either to a specific milestone you control or to the ultimate delivery by the agreed-upon deadline. In an ideal world, if you work smarter, faster, and better, then you'll get paid more and get more flexible working conditions.
Does that mean everything is open to negotiation? Of course not. In fact, if you are ever going to be in a position to negotiate special rewards and increased flexibility for yourself, the first thing to consider is what is not negotiable. What are the basic requirements of the job, the essential performance standards, and acceptable behavior? What are the basics for which you should expect nothing more than to be treated fairly and paid for your work? Those are the deal breakers.
Once you deliver on the basics consistently, then you put yourself in a position to seize opportunities to go above and beyond and thereby earn more. Keep your eyes peeled for those opportunities. When they present themselves, focus like a laser on the value you bring to the table. Then you will be in a position to negotiate for increased rewards and flexibility. And remember, you’ll have much more success if you don’t try to negotiate for long-term fixed rewards, but rather for small rewards tied to concrete, measurable performance benchmarks that are within your control.
One executive I've worked with put it this way: “You want something from me? When you ask, I want to know: ‘What is the benefit of what you are proposing? Is there a benefit to me? To the company? To the group? What will it take to make this happen? What role are you going to play? Who else is going to be involved? How long is this going to take? Where is this going to happen? How are you going to do it?’”
Indeed, if you answer those questions every time you make a request for a reward of any kind, you will, in effect, be preparing a simple proposal. I have seen this technique work wonders for individuals seeking additional resources or rewards or more flexible working conditions.
Requests are serious business. Learn to write a simple proposal if you want more resources for your work; greater financial rewards for yourself or your subordinates; greater access to perks; credit for results achieved; more challenging tasks, responsibilities, or projects; special assignments; training opportunities; exposure to decision-makers; the chance to work in a choice location; scheduling flexibility; or even quirky personal accommodations. If you impose this discipline upon yourself, you will tend to make fewer requests. You will also make more reasonable requests and, almost certainly, make requests in a more professional manner.
The very act of putting your requests into a proposal format will cause you to consider those requests more carefully. And the more carefully you consider your requests, the more you're able to show your boss the benefits of what you are proposing to do, the more likely it is that you will be able to earn more, and better, rewards.