Having the Here’s-What-I-Want Conversation with Your Boss
by Rebecca Shambaugh
One person stands between you and your next raise or promotion: your boss. While others on the leadership team—and even your peers—may exert some influence on your career, it’s your direct supervisor who can pull the strings to either grant or deny your advancement. But to get what you want, you have to ask for it.
I once spoke at a conference in New York, where a female executive pulled me aside to ask my advice on this topic. She explained that while she was on the verge of being promoted to the C-suite, her family situation with three children had many demands. She was feeling conflicted about whether or not she could take on higher-level responsibilities while remaining both a strong professional and a strong parent. In confidence, she shared with me that she was planning to resign from her position and company later that month.
I then asked her a question: “Did you consider going to your boss and directly asking for what you want—maybe some additional time off or even going part-time for a while—to facilitate your ability to accept the promotion while still making more time for family?” My point was that when it comes to your career, whether your goal is a promotion, a raise, or something else, it doesn’t have to be all or nothing—if you learn how to identify what you want and confidently ask for it.
At its core, the act of asking your superior for something important to your career progression may make you feel vulnerable—yet summoning the courage to do so actually demonstrates strength. Whether you seek more money, higher status, increased visibility, additional resources, or more time off, you likely won’t get it if you don’t specifically ask your boss for it. What’s more, many bosses expect you to directly ask for what you want. Asking shows both self-confidence and respect for your manager, since you are requesting, not just expecting, help.
Assuming that you’ve already done your prep work—researching your case and your company’s policies and financial position—here are a few tips on actually having that conversation with your boss.
Avoid assumptions by asking the right questions
Successful negotiation is about not just asking for what you want, but also approaching your “ask” strategically. A poor strategy is to approach negotiations one-dimensionally, focusing only on your own desired outcomes. Instead, you should take a collaborative approach, building a clear bridge between your boss’s concerns and your request. The best way to do this is to pose a few open questions that explore your boss’s view of the world. When formulating these questions, be curious about how to make your request a win-win. For example, you might try using phrases that imply joint success, such as:
- How do we both do well?
- How would you define success?
- How can we turn this into a win for you?
However, in keeping your boss’s perspective in mind, be careful not to spend too much time listening passively or go overboard with the questioning. The key is to find the perfect balance between listening and asking questions, ultimately steering the discussion toward an answer.
Gather context through open dialogue
Getting the lay of the land directly from your manager before asking for what you want can help you formulate a better strategy. Initiate an open dialogue tailored to the specific points you plan to negotiate. For example, if you’re targeting a promotion, you might ask something like this: “Now that I’ve been in this role for two years, what actions would it take to advance to the next level?”
This type of question can spur your boss to reveal valuable information to guide your future negotiation. For example, your boss may tell you that there is currently a freeze on promotions but it’s an avenue that can be explored in six months. In this case, you’ll then know that the timing is wrong to negotiate for a promotion right now—so you can shift gears to ask for something else, or pose other questions to gather the information you need to get what you want down the road. For example, some questions you might ask include:
- Assuming things are different six months from now, what are my chances of gaining a promotion?
- What specifically do I need to do to achieve this goal?
- Are there stretch assignments that I can take on over the next six months to prepare me for advancement?
Then follow your boss’s guidance, and commit to revisiting the topic in six months for a reevaluation of the timing.
Use “what if” responses
One way to build on your boss’s responses during the open dialogue stage is to have some “what if” responses ready to go. “What if” responses give you a way to further the conversation by suggesting specific actions that you might take when your boss makes a general suggestion. For example, if your boss says that you need more cross-functional experience before you can advance, you might reply with an exact strategy that you could implement to get that experience, such as:
- What if I work directly with the marketing department on the Johnson campaign?
- What if I take the lead in sharing our communications strategy with the sales team?
- What if I shadow the distribution team lead for a week, or participate in a one-day role swap with a peer in the finance department?
Involving your boss in your request by using the “what if” tactic will help gain their buy-in and commitment with a tangible plan that can be tracked and monitored.
Let the conversation evolve
Even if you execute a perfect ask, there may be circumstances beyond your control that cause your boss to reject your request. Don’t become so fixated on achieving your ultimate goal that you leave possible chips on the table. Keep an eye out for viable backup plans that emerge as the conversation unfolds. Even if you get a “no” to your original request, you can still leave the negotiation with a small win that may put you on the path to an eventual “yes.” Your goal should be to avoid ending up in a position where the response is a final “no.”
For example, say you ask for a salary bump, proving through your internal and external market research why you deserve one, and your boss responds that there’s currently no budget for raises in the department. You might then shift the conversation to requesting an extra week of vacation, more flexibility in your job, a benefit option, or paid continuing education in an area that supports your career goals.
Even if you accept a plan B as a result of your current negotiation with your boss, that’s no reason to give up completely on what you really want. If your manager denies your request the first time, it doesn’t necessarily mean that “no” is the final answer.
No matter your perceived level of expertise in negotiation or the style you use to go about it, there is power in simply moving beyond your nervousness and starting a conversation with your boss about what you want. By doing so, you’ll begin to build both your skill level and confidence, preparing you for future negotiations.
While you may not get what you want every time, if you don’t ask, you’ll never know.
Adapted from content posted on hbr.org, November 20, 2015 (product #H02IBL).