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  • Dana Ferrante

Pitch Perfect: How to Convince Your Boss to Make a Change

Sponsored Content Disclosure: I'm happy to have had the chance to work with our sponsor Bevi to share these helpful tips with you!

Pitching a new idea to team members

No matter what type of support role you are in, speaking up is always a challenge.

It’s true: your primary responsibilities as an assistant are to give support, provide aid, and be the trusted gatekeeper. This, however, does not mean you have to blindly back every decision or keep any informed opinions to yourself.

Here are four common scenarios and the tactics you can use to effectively convince your boss to try something new.

Laptop with new software

Scenario 1: You want new or upgraded software

Automation is a beautiful thing.

In today’s world, there are many ways to automate repetitive clerical tasks such as inputting business cards into your boss’ contact list or generating reimbursement reports. Just because these types of tasks are a large part of your responsibilities in the office doesn’t mean they have to take up the majority of your time.

Don’t waste your valuable time and expertise on repetitive tasks - make time for projects that will help you grow! Here are a few tactics you can use to prepare, pitch, and prosper:

  • Do your research. Before broaching the subject, do an in-depth survey of the type of software, app, or program you’re interested in. Create a spreadsheet or chart that compares pricing and capabilities (you might even find a pre-made comparison chart online). Brainstorm questions or concerns your boss may have and have the answers on hand.

  • Be logical, not emotional. Your boss is familiar with your workload and your skills, so it’s not enough to say that the new software will make you “happier” or “more productive.” Provide your manager with quantitative data. For example, “If I do these reports with the new software, I will have 8 more hours each week to devote to another project that is a higher priority.” Be transparent about the price and use your knowledge of the office budget to find a place where you can potentially decrease spending.

Pitching a health and wellness initiative

Scenario 2: You think the company should invest in a health and wellness initiative

From lowering overall healthcare costs to reducing absenteeism, there are numerous ways an employee wellness initiative can have a positive impact across the company.

While the initiative will undoubtedly boost employee morale, your boss might see your proposed initiative as an additional cost, and therefore, a loss for the company. Here’s how to convince them otherwise:

  • Use emotional appeals and share relatable anecdotes. Unlike time-saving software, a health and wellness initiative is a bit tougher to correlate numerically with things such as performance or costs. Before pitching what you would like to add to the office, share some relatable stories to get your boss in a more emotional mindset. For example, if you’re interested in addressing dehydration in the office, start by talking about a time when you forgot your water bottle - and didn’t want to spend money on water at the cafe down the street - so you ended up with a massive headache by the end of the day. We’ve all been there!

  • Give them options. Do some research into what other companies have implemented and draft a comprehensive proposal. Separate your proposed items or programs into different pricing tiers, or divide everything into a separate list of ‘must-haves’ and ‘wish list’ items.

  • Try creating a 3-month, 6-month, and 1-year plan or forecast. Not every office has the budget to launch a full-blown wellness initiative on the first try. Be sure to include details regarding how the program can expand over time and how you will measure its success.

Gather your anecdotes, draft some potential rollout plans, and make a great case for a health and wellness initiative in your office!


Scenario 3: You want a promotion or raise

You’ll likely need to advocate for yourself and ask for a promotion or raise at various points in your career. If you’re making this request at a company you’ve been with for several years, it might feel especially nerve-wracking to ask for something new and different. Even if you’re not currently thinking about asking for a raise, the best thing you can do is pretend like you are:

  • Keep an accomplishments document. Outline the major responsibilities and projects you’ve worked on since starting your job. It’s good to get in the habit of recording what you’ve accomplished at the end of each project so you’re not left trying to remember everything six months down the road.

  • Lead with logical arguments and numeric data. In addition to your accomplishments document, you should also keep a savings spreadsheet that outlines how you have saved the company money. While your boss may be familiar with your day-to-day tasks, they might not recognize what quantifiable improvements you have made to your role, or the office budget, over time.

  • Be prepared for a “no.” Rather than get upset or spend time wondering why your boss said no, ask your boss directly what you would need to accomplish in order to earn a raise or promotion. This is a time in which you should keep your emotions and opinions separate and take notes. Find out what they’re looking for, and go out there and do it! If after a few months you feel their expectations are unrealistic given your current resources at the company, it might make sense to make a career move!

Hiring a new employee

Scenario 4: You think the company should hire more staff

These days, one assistant is often not enough. If you’re constantly crunched for time or feeling like you’re doing the work of three people, here’s how you can make a case for hiring additional support staff for your executive team:

  • Conduct an audit and crunch the numbers. Meet with each member of your current team - or do a detailed survey of your own responsibilities - and make a spreadsheet that represents how much time and resources goes into each task. Use this breakdown to quantitatively demonstrate how much time you need (versus how much time you have); an astute boss will quickly realize how overworking employees can negatively affect ROI.

  • Identify the ideal skills, experience, and job duties of a potential new hire. Once you identify the needs and costs, take some time to write a description of your ideal hire and their potential responsibilities. Not only will this evidence your commitment to hiring someone new, but will also help jumpstart the recruiting process.

  • Make the case for full-time staff over temporary hires. Be prepared: your boss may reject your proposal from a strictly financial prospect. If they mention the prospect of temporary staff, make sure to have numbers on hand that show just how long it would take to interview, hire, and onboard these folks. (In fact, the entire process will likely add more to your plate in the long run!) While temporary staff members are useful for clearly defined projects, ultimately full-time staff are a more valuable, long-term investment in the success of the company.

If any changes need to be made in the office, you’re likely the first one to notice - and undeniably the right person to propose a solution. Never doubt your own ability and insight: outline the major points, do your research, and pitch your boss with confidence!

Dana Ferrante

Dana Ferrante is a Content Marketer at Bevi, the all-in-one hydration solution providing offices across the US and Canada with customizable refills of still, sparkling, and flavored water that never run out. She spends most of her time crafting useful guides for Executive Assistants, Office Managers, and Admin Pros of any sort, and is an avid lover of sparkling grapefruit water.

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