Describe a time in your career when you were frustrated or disappointed. What did you learn from that experience?

Sample One

While working as a Sales Representative for DTR, my job was to distribute group insurance products through various brokers. The industry's close ratio was around 5%, thus there were many sales I did not win; however one lost sale in particular was quite memorable.

After receiving a request for a proposal from a broker in Manhattan, my underwriters and I rated the risk, and I subVMIted an aggressively priced proposal. I was extremely confident in the sale, especially after the broker informed me that my bid was the most competitively priced out of all he had received. I was shocked and disappointed when I found out the broker renewed the incumbent's contract.

Once I overcame my initial disappointment, I reflected on what caused me to lose the sale, despite having a competitive bid. One of the primary reasons was that I did not effectively use the resources at my disposal. Prior to losing that sale, I had quite a bit of success, which made me somewhat overconfident, believing I did not need help or advice from more tenured colleagues. The lost sale humbled me, and I realized I had tremendous resources around me with an office full of senior salespeople, each with decades of experience. Afterward, I connected with my senior colleagues and identified different styles and techniques that I could utilize in future relationship building. Now, I always seek out mentoring to help me grow as a professional, which has proven to be so beneficial, that I have partnered with junior colleagues to share my experiences and advice. Aiding the development of junior employees has been a rewarding experience for me, and a very positive result of losing that sale.

Another reason for losing the sale was the lack of a strong relationship with the broker. My previous relationship-building efforts focused on presenting the technical merits of my product, without necessarily taking into account the client’s needs. My primary concern was with winning business, not with the clients as individuals. My new approach connected with the brokers as individuals, by demonstrating my interest in their lives beyond professional duties. The other half of my new approach was to use consultative selling techniques, using effective questioning and listening to uncover the needs of the broker, and any deeper needs behind the more immediate ones.

While a consultant, I applied these lessons during a series of meetings to pitch a new project to a large client. I established a personal rapport with key personnel, and used effective questions to demonstrate technical proficiency. With some senior mentoring, I was able to significantly help my team win the project, and have enjoyed becoming the client’s trusted advisor.


Although the experience of losing a seemingly promising sale was disappointing and shocking, this initial shock and disappointment led me to explore my behavior, and begin a course of self-correction, which has been extremely beneficial from a personal and professional sense. I effectively partnered with senior mentors for different aspects of my career, and formed long-lasting relationships across my industry.

Sample Two

I experienced a frustrating situation while serving as project manager for LOCO’s conversion to a new currency trading system. While my team successfully completed the conversion on schedule, the project’s final step, coordinating a global network of users to operate the new system, turned out to be a frustrating and disappointing experience.

I began the coordination component by sending mass communications to all interested parties outlining the conversion plan. Then, I created and sent standard operating procedures, a troubleshooting guide, and PowerPoint presentations covering both general and specific topics. Later, as the launch date neared, I conducted a host of conference calls and live web trainings aimed at resolving any last minute problems. Confident all users had sufficient opportunities to learn the new system, I moved forward with the launch.

Once the new system was up and running, it became clear there was a small but significant population of users who hadn’t kept pace with the training, resulting in less than ideal success. This was frustrating and disappointing on a number of fronts.

First, it was difficult to play catch-up on the already live system. I had to scramble to contact and train the users who were lagging behind, which required working well into the night and early morning hours on short notice for colleagues in Asia, Europe, and the Middle East. My frustration grew as I learned the importance my client, LOCO, placed on successful usage of the new system wasn’t shared with each of their international trade partners. This forced me to spend even more time and energy persuading operations teams at a number of foreign broker-dealers to learn and utilize the new system.

The experience taught me valuable lessons about project management. First, I could have taken a different approach to the training/messaging aspect. While the steps I took were important, I could have been more thorough in establishing expectations with managerial contacts at the foreign offices much earlier in the process. In projects I’ve managed since this experience, I’ve been keen to take this important step early and often.

Second, when we planned the logistics of the launch, my team failed to consider ”going live” in waves, firm by firm, rather than all at once. This would have slowed to project down to an extent, and added a few layers of complication, but in retrospect, it would have allowed us to monitor and train firms individually until they were completely up and running on the new system. This could have made for a smoother and more efficient transition.

Lastly, I’ve developed a new perspective about managing risk. Throughout the project, I focused my energy on the steps that contained the highest concentrations of risk rather than managing risk from a holistic perspective by carefully analyzing it at each step. In work I perform today, I now make sure to measure and mitigate risk at each stage of a project, continually highlighting those risks with all interested parties.