How to Confidently Ask for What You Want (and Need) at Work

women sitting around desk going over papers
Laurie Maddalena, MBA, CSP, CPCC Photo
Executive Coach/Consultant
Envision Excellence LLC

8 minutes

6 tips to aid in speaking up and taking action without fear of negative consequences

Have you ever wanted something at work but were afraid to ask for it? Perhaps you spent a significant amount of time thinking about why you couldn’t have (or didn’t deserve) what you wanted, so you talked yourself out of even putting your desire on the table.

This was the case for me as a young executive working in a credit union. We had a new CEO who had a grand vision of elevating our organization to a new level. Our goal was to create a best place to work and to attract and retain the best talent in our metropolitan area. A lot of resources go into making a vision like that successful and, as the vice president of human resources, I was feeling the pressure to deliver.

There was one problem: My team was overwhelmed, and we couldn’t keep up with the new positions that were being added over the next six months. I felt that we needed to hire a manager over the talent acquisition area, but I was certain my boss wouldn’t go for it. We had added a position to the department the year before, and I knew we already had more employees than a typical HR department for a credit union of our size and assets.

Negative thoughts dominated my mind and kept me from asking. “My boss will think I’m greedy, incompetent, incapable and ballsy. He’ll think I’m not efficient with my time and not able to manage my team properly.”

I hesitated for weeks before I finally put together a plan and approached my boss. I went in prepared to make my case for why adding a high-level position was necessary for us to reach our strategic goals, as well as how the investment would pay off long term. I nervously brought it up one morning when we were meeting. His response baffled me. “I’ve actually been thinking the same thing,” he said. “I’d like to hear your plan of how you would use this position.” I was stunned. I had spent over a month ruminating on all the reasons I would be turned down, convincing myself of the worst-case scenario. All that wasted time and energy was unnecessary.

Why did I spend time overthinking and overanalyzing rather than asking for what I needed? According to Katty Kay and Claire Shipman, authors of The Confidence Code, women tend to avoid risks, underestimate their abilities and spend more time thinking about the consequences of failure. And women tend to strive for perfection, which is the enemy of confidence. Perfectionism is a fallacy, and if we hold ourselves to that standard, we will constantly fail and be generally less confident than men.

These tendencies cause most women to hesitate to take action and ask for what they want. It’s hard for me to put that on paper, yet I have seen this lack of confidence in many women I have worked with as an executive coach.

It’s important to note that companies that employ women in large numbers “outperform their competitors by every measure of profitability,” according to the authors of The Confidence Code and recent studies—proof that our actual performance is much better than our perception of our performance.

Kay and Shipman suggest that building confidence comes from taking action. We need to think less and act more. Professional success requires political savvy, a certain amount of scheming and jockeying, some self-promotion and not letting no stop you.

My mentor, Jack Canfield, said something that changed my perception of asking: “You reject yourself in advance by not asking in the first place.” By not asking, we don’t even have a chance of getting what we want or need in life.


Laurie Maddalena, MBA, CPCC, PHR
Executive Coach/Consultant
Envision Excellence
It’s important to note that companies that employ women in large numbers outperform their competitors by every measure of profitability—proof that our actual performance is much better than our perception of our performance.

Maybe you won’t always get a yes, but you will never get a yes if you don’t ask. Whether you want to ask for feedback, more resources, to work from home, more coaching, a raise or to attend a board meeting, below are six tips for increasing your chances of getting what you want.

  1. Overcome your hesitation. Before you talk yourself out of asking for what you want, get clear about the consequences of not asking. We often focus on how we will feel if we get a “no” rather than focusing on how we will feel if we don’t take action. Will your frustration continue to build and impact your performance? Will you miss out on a great opportunity? Most of our fears are created in our heads and aren’t reality. It’s highly unlikely that you will be fired for asking. Remember, you will rarely get what you don’t ask for.
  2. Don’t assume. If you are waiting for your manager to notice that you need more help or resources, that is not a good strategy. No one is a mind reader. People are busy and often focused on what is right in front of them. Although, ideally, managers are regularly talking with employees to understand their challenges, not every manager is trained to coach and connect with employees this way. Assume the best intent and be clear about your challenges and what you are asking for.
  3. Don’t complain. A surefire way to hear “no” is to approach your manager to complain about how much work you have or how your co-worker isn’t pulling her weight. When you approach your manager with only challenges, it puts the problem on her plate and leads to more frustration. It’s unlikely you will get what you want if your manager is frustrated. Brainstorm solutions before you broach the subject.
  4. Go in with a plan. Whether you are asking for more help or to work from home, think through your approach beforehand. What objections might your manager bring up? How will your request benefit or hinder her or the team? Think strategically about the impact of your request and come prepared with suggestions or a plan to overcome any challenges. You will also want to address why you want what you are asking for. Perhaps working from home two days a week will allow you to be more productive because you won’t be drained by your long commute. Or perhaps attending a board meeting will give you a higher-level perspective that will help you on an important project. Make sure you are focusing on how your request will benefit your boss and the team, not just you. If working from home is only beneficial for you but puts a lot of stress on your co-workers and your boss, your request may be seen as self-serving.

    Thinking through your approach will also help you to feel more confident in making your request. Go in with a positive expectation and be prepared to explain the benefits thoroughly. If you are timid in your request, your manager may not take you seriously.
  5. Be clear about what you are asking for. Vague requests are usually met with vague results. For example, if you would like more coaching to improve your skills, be specific about what you are looking for. Rather than saying, “I would like you to coach me more,” you could say, “I’d like to work toward a management role in the next year. Would you be open to meeting every two weeks for an hour to provide me feedback and suggestions on how I can get there?”

    I often hear from employees in my leadership program that they don’t get enough feedback from their managers, and they aren’t sure how to ask for feedback directly. I suggest avoiding broad requests like, “I’d like to get your feedback on my performance.” In my experience, most managers feel caught off guard by this and will give a not very helpful response. Instead, be specific in your request. You might say, “Can you share one of my best strengths from your perspective as well as one area I can work on?” Narrowing the scope of your question makes it easier for your manager to provide more actionable, meaningful feedback. And when you receive the feedback, respond with, “Thank you. I really appreciate you sharing that information with me.” Showing your appreciation will make it more likely that your manager will continue to provide feedback.

    As professionals, it’s in our best interest to get comfortable asking for feedback rather than waiting for someone to provide it. Although a great manager understands that providing regular, meaningful feedback is part of their responsibilities as a leader, most don’t provide it enough and others find doing so uncomfortable. By asking, you are really giving your manager permission to be open and honest with you, which takes off some of the pressure.
  6. Pick the right time. When you are prepared to ask for what you want, make sure you pick an appropriate time when your boss is likely to be receptive. Avoid first thing in the morning or typically busy times like just before a board meeting. You want your manager to be in the best frame of mind and the best mood to really consider your request. Allow ample time so you are not rushed.

While there’s no guarantee that you will get a favorable answer, to get anything you want in life, you have to be willing to step outside your comfort zone. Those who learn to confidently ask will immediately increase their chances of success and happiness.

Laurie Maddalena, MBA, CPCC, PHR, is a certified executive coach, leadership consultant and founder of Envision Excellence, LLC in the Washington, D.C., area. Her mission is to create exceptional cultures by teaching leaders how to be exceptional. Maddalena facilitates management and executive training programs and team-building sessions and speaks at leadership events. Prior to starting her business, she was an HR executive at a $450 million credit union. Contact her at 240.605.7940 or

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