How Should You Ask for Something?
Asking for something big can be a daunting task, but it can also lead to life-changing experiences. We’ve gathered six personal stories from professionals like founders, CEOs, and community experts, sharing their experiences from a big business proposal to requesting a sabbatical for personal growth. Dive into these inspiring tales and learn how they approached these significant moments in their lives.
- Big Proposal Leads to Business Success
- Courageous Loan Request Strengthens Friendship
- Pursuing Benefits and Skills Pays Off
- Bold Blurb Request Wins Author’s Endorsement
- Setting Boundaries Reveals Boss’s True Colors
- Sabbatical Request Enables Personal Growth
Big Proposal Leads to Business Success
I recall a defining moment when I took the leap and sent a proposal to a potential client. The magnitude of the project was daunting, but I knew it had the potential to be a game-changer for my young company.
While nerves crept in, I mustered the courage to ask for a fair price that reflected the value we would deliver. The significance of the ask weighed on me, but I believed in the quality of our services.
To my delight, the client responded with a resounding, “Let’s do this.” It felt like an angel investment, propelling my business forward for years to come, especially during the challenging times caused by the global recession.
This experience taught me two valuable lessons. First, imposter syndrome is a natural part of the process, reminding us to push past our doubts. Second, being assertive in our requests can yield surprising positive outcomes. Even if a lead is lost, the potential upside, if it works, outweighs the risks by far.
Rafael Sarim Özdemir
Founder and CEO, Zendog Labs
Courageous Loan Request Strengthens Friendship
I asked a friend to lend me a large sum of money. I explained my situation and promised to pay them back with interest. They agreed, and I could get back on my feet. It takes courage to ask a friend for a loan, but if done correctly, it can be a successful way to get financial help.
It’s important to have a repayment plan in place and to offer interest as a gesture of appreciation. In my case, my friend was fortunate to help, and it strengthened our friendship knowing that we could rely on each other in both good and bad times.
Roy Lau
Co-founder, 28 Mortgage
Pursuing Benefits and Skills Pays Off
When the economy took a downturn, I was grateful for being able to remain employed throughout most of the pandemic. The wage compensation wasn’t very favorable given the wide range of work required of us to perform, which varied.
However, they provided a wide range of wonderful benefits, which were things I expressed an interest in during the onboarding process. After a lot of hard work, stress, conflict management, and endurance, I could attain all the interests I expressed during my hiring day, besides the skills I use today.
Today, I work for another large international corporation where the question was posed, “What could make the company better?” Although the benefits are by far the best, the majority agreed that increased wages and increases to wages are always the highest on the list of favorability next to having time off.
In the pursuit to establish a solid career path, access to a pension would also be favorable, but not the highest on the “majority” list of priorities.
Areale Hanks
Owner and Designer, Dont’e & Carmelo
Bold Blurb Request Wins Author’s Endorsement
I asked a famous author for a blurb for my upcoming book. After researching their work, I crafted an interesting pitch and reached out to them with my request. I emphasized how their endorsement would help my book reach a wider audience.
To my surprise, they agreed to write a blurb after being impressed with my book’s premise. This experience taught me the importance of networking and being bold in pursuing opportunities. It also highlighted the value of showcasing one’s work in a clear and concise manner when making big requests.
Jason Cheung
Operations Manager, Credit KO
Setting Boundaries Reveals Boss’s True Colors
It takes a lot of courage to demand something from a person in a position of power. A few years ago, I had to deal with a boss who mobbed me. I summoned up the courage to ask him to respect my boundaries.
Among many of his unacceptable behaviors, one made me reach the end of my rope.
Though it wasn’t included in my contract, he constantly contacted me after working hours. Raised voices, insults, and offensive remarks happened in our office every day. It escalated when a late-evening phone call remained unanswered.
The last straw was when my ex-boss called me on Saturday morning without apologizing. In return, I explicitly, yet politely, asked him not to call me on weekends.
On Monday, I was welcomed with a burst of rage and offensive accusations. In return, I gave him a notice, which triggered his fury even more.
I learned one crucial truth from this experience: sometimes observing the other party’s reaction to your requests gives you a chance to see through them.
Martyna Szczesniak
Community Expert, MyPerfectResume
Sabbatical Request Enables Personal Growth
I asked for a sabbatical from work by creating a proposal outlining my plans for personal growth and the benefits for the company. My boss approved, and I could take time off to travel and recharge. While it was a big ask, it showed a level of prioritizing self-care and personal growth, which is often overlooked in the workplace.
It required a lot of trust from the employer and a well-crafted proposal that was focused on a win-win scenario. This experience taught me the importance of advocating for oneself and the value of taking time off to recharge.
Ben Lau
Founder, Featured SEO Company
Submit Your Answer
Would you like to submit an alternate answer to the question, “Money. Marriage. Jobs. Asking for something is tough. Tell us about a time when you asked for something big. What happened? How did you ask? Share your story.”
