4 Ways to Ask Your Boss for (Almost) Anything

Conversations with the boss are challenging. In your mind, you have a perfectly reasonable desire: more money, the opportunity to continue working from home, space to complain about a co-worker or extra time off. But “up conversations,” the conversations you have with someone up the hierarchical chain, are fraught with pitfalls. Hierarchical power struggles taint these interactions. Power imbalances, conflict avoidance, the fear of emotions and dysfunctional communication patterns are common barriers to respectful, mutually beneficial exchanges.

There are, fortunately, methods that can help you avoid these hierarchical power struggles. With a few changes in your approach, you can engage in productive conversations that dramatically increase your chances of getting what you want.

No matter the ask, having the right conversation at the right time, with the right attitude in the right way will bring out the best in you and your boss.

Here are four tips for navigating those potentially hazardous conversations:

1. Ask to have a conversation about the conversation you want to have. 

Because these conversations can be fraught with tension, it’s easy to put them on the back burner. However, when frustrations simmer, they can boil over at inopportune times. At the end of a long meeting, you might unexpectedly blurt out, "By the way, we really need to talk about my future here." In a flash, your boss is on the defensive, and later you will probably kick yourself for opening your mouth.

Avoiding the up conversation allows our dissatisfactions to grow over time; it’s better to make an ask or bring up a concern sooner rather than later. A well-considered request to schedule time for a future discussion is enormously beneficial. Consider: "Jami, can we compare notes next week about my work and my future with the team? I’d like to discuss my goals and get your advice." Keep it simple,professional and make it as specific as possible. A request for a conversation sets the stage for the discussion and gives you and your boss time to prepare.

2.  Check your negative emotions at the door.

In any relationship, managing your emotions is crucial for honest, productive conversations. John Gottman, a respected researcher in marriage stability, found that "the difference between happy and unhappy couples is the balance between positive and negative interactions during conflict. There is a particular ratio that makes love last. That 'magic ratio' is 5 to 1." Applying that ratio to business relationships increases positive interactions, which builds a relationship's emotional bank account, allowing you to enter a challenging conversation with an affirmative spirit.

Entering a conversation with anger or resentment won’t serve you well. To check your negative emotions at the door, you have to unwind from them. This brief article illustrates how our brains are wired toward a "negativity bias." When we’re stuck in a negative loop during difficult situations, our fears and stress hormones kick in. The good news is that our brains are plastic, and with self-awareness and a little practice, we can rewire our thinking so positivity can reign.

Rather than blurting out in frustration, "You just don't appreciate my work!" you can enter a conversation with a positive attitude. Instead say, "I love my work, and I'd like some feedback on how I'm doing from your perspective."

Don't forget to show gratitude: "Thanks for giving the team credit at the meeting with the VP." A dose of appreciation can cure so much of what ails a relationship.

3. Examine your desires and goals.

Desires and goals are inspirational, but we're often disappointed when our wants don't align with reality. I once had a client who desperately wanted to be a director. He was convinced that he was in line for the next promotion. Desperate for advancement, he failed to see that what he wanted wasn't possible at that moment.

It’s crucial to understand your goals in the context of your situation. A request for a promotion in the shadow of a poor evaluation won't serve you well. And when a company is cutting back and offering voluntary leave packages, you shouldn't be asking for more of anything.

An appreciation for the bigger picture can drastically shift the power dynamics of a conversation. An excellent way to start a conversation is by demonstrating your grasp of the company’s context and the challenges your boss may be facing. Depending on the situation, you might need to show patience, demonstrate a willingness to compromise or make a creative suggestion about other possibilities. It might be helpful to say something along these lines: "I realize the timing for a promotion isn't right, but I'm willing to take on more responsibility if we can review the position and salary in three months." Educating yourself about the facts — like them or not — will always ground you in reality and guide you toward a thoughtful conversation.

4. Accept the rules of the hierarchy.

Power dynamics are stressful in any relationship. In hierarchies, someone is always above you, no matter your position. Even the CEO has a boss.

Balancing power in conversations is a central challenge in any hierarchy. A boss — bad or great — has authority on their side. They have the responsibility to make decisions, small and large, that have consequences for your life.

A good job comes with benefits and sacrifices. On one side of the coin are steady pay, a 401(k), vacation time and health insurance. On the flip side are the aspects that are harder to accept, most notably your lack of control over most facets of your employment. You won't always get what you want. The challenge is to avoid the temptations of negativity bias. Don't be someone who says, "I knew he'd get the promotion," or "I can't believe they passed me over!"

Self-awareness and acceptance of both sides of the coin are psychically healthy. Rather than fighting reality, we can bring our best selves to a conversation by accepting a boss's authority and channeling our ambitions into what's possible in the future. Imagine saying something like, "I appreciate the tough decisions you have to make, and I'd like to know how I can improve and work toward a promotion." Focusing on the quality of your work and your relationships will enhance your chances of getting more of what you want.

Approaching these conversations with the right attitude is vital for realizing your ambitions. To get more out of your career, reflect on these four tips for engaging your boss in a collaborative conversation. If you can avoid anxiously pushing to get what you want, you might be surprised by how much you can shift the mood of the conversation. With some self-reflection, a little practice, a dash of humility and a positive attitude, you can find new ways to ask the boss for almost anything.