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Answering Interview Question: Tell Me About a Time When You Convinced Your Boss to Agree with Your Proposal (Plus Sample Answer!)

By Bob McIntosh

Answering Interview Question: Tell Me About a Time When You Persuaded Your Boss (Plus Sample Answer!)Rarely will anyone say behavioral-based questions are easy to answer.

Behavioral questions require a job candidate to recall a time when they performed a skill successfully, or unsuccessfully, and then tell a story about performing that skill.

The story must be relevant, specific, and succinct.

Preparing for Behavioral Questions

Answering these questions well are challenges job candidates struggle with. Keep this thought in mind...

The employer's goal with behavioral interview questions is to understand how you have responded to certain situations in the past to predict how you would act in a similar situation if you worked for them.

Too many people I’ve interviewed try to deliver a generic, long-winded answer that doesn’t hit the mark. This is not what interviewers are looking for.

The four thoughts candidates need to take into consideration are:

  1. Interviewers want to see how you're going to respond to difficult questions.
  2. Interviewers want to see self-awareness/honesty.
  3. Understand why the interviewers are asking the question.
  4. Have your (short) example ready.

For details about how to successfully answer behavioral interview questions, read -- Tell Me About a Time When You Failed and Smart Strategies to Answer Behavioral Interview Questions.

How to Answer the Convinced-Your-Boss Question

Let’s look at a behavioral-based question that’s purpose is to determine a candidate’s ability to persuade her boss. The question may also be delivered as such: Tell us about a time when you convinced your boss to adopt an idea that he disagreed with” or "Tell us about a time when you and your boss disagreed, but you were able to get your boss to change her mind."

With your answer, demonstrate your knowledge and skills, your judgement, and your ability to negotiate successfully with someone senior to you.

Think back to your experiences and a boss -- or someone senior to you, if a story with a boss doesn't come to mind. Then, think of the elements necessary to effectively share the experience.

Sample Answer

In answering this question, give the interviewer a sense of the situation (S), the task (T), the actions you took (A), and the final result (R). [The acronym is STAR.] Then, for additional points, share what you learned as a result of the experience.

 The Situation: 

Our company was using Microsoft Excel to keep track of our customers' orders and appointments, but the process proved to be inefficient. It was becoming laborious to enter customer information and keep the orders up-to-date, and the sales department complained that accessing it was too difficult.

 The Task:

As the sales operations manager, it was my responsibility to maintain this antiquated process. I knew we needed a better process, so I approached my boss to explain that we needed a true CRM software. His reply was that we didn't have the money, nor the need for CRM software.

 The Actions: 

I knew this was going to be a challenge to persuade my boss that we needed an up-to-date CRM software, and I knew he wouldn't agree with my suggestion without solid proof.

First I called our main competitors to see what they were using to organize their customer transactions and appointments. At least nine out of ten were using CRM software. And most were willing to tell me the brand they were using.

Salesforce was being used by the five of our competitors. Hubspot was was second with two, and Zoho and Agile were the others.

I knew my boss wouldn't go with Salesforce just because it was the leader of the pack. He would want to know why it would be the best fit for our sales and marketing department.

I conducted thorough research on the four products, including one called Kintone, which was in the top ten for security. The others didn't list that information. I knew we needed a product that would store customer data, track customer interaction, track leads, and most importantly be user friendly for the sales team.

My last task before going to my boss with some hard data was to ask the sales team what they needed in a CRM software. They were helpful in confirming what I felt they needed. The one feature they wanted most was easy access and usability.

After two weeks of researching products and talking with salespeople, I narrowed the list to three software providers, based on reputation; overall customer interaction; ease of use; and, of course, price.

I asked my boss if I could have half an hour of his time to discuss my CRM proposal. He reluctantly agreed. When he entered the conference room, he was surprised to see a PowerPoint presentation I created shining on the screen.

At the conclusion of my presentation, he paused for what seem like hours and finally asked me which software I would suggest. I said Salesforce, but he liked Zoho better.

 The Result: 

We implemented Zoho CRM, which over two years improved efficiency by 50%. I know this because I tracked the hours the staff had used with Excel and later used with Zoho.

 Bonus - The Learning: 

I learned that the way to persuade my boss was to show him what I proposed, rather than get into a heated debate. This is how I have, and will continue. to persuade my bosses to agree with my suggestions.

Notice the Bonus - The Learning. Particularly if a situation is not a success, be sure to include your learning from the experience.

The Bottom Line:

Behavioral questions are becoming more common, so having a few STAR-L experiences to share in your job interview toolbox is a smart idea. Focus the story on answering the question, but don't spend more than 90 seconds on an answer. A long monologue is a big mistake.

More About Succeeding at Job Interviews


About the author...

Bob McIntosh, CPRW, is a career and LinkedIn trainer who leads more than 17 job search workshops at an urban career center. He also critiques LinkedIn profiles and conducts mock interviews. Bob has gained a reputation as a LinkedIn authority in the community. His greatest pleasure is helping people find rewarding careers in a competitive job market. Visit his blog at ThingsCareerRelated.com. Follow Bob on Twitter: @bob_mcintosh_1, and connect with him on LinkedIn.