How to Convince Your Boss to Say Yes

Getting buy-in from senior management on any idea is challenging. Even more difficult: convincing them to invest in something where the ROI cannot be easily calculated, like with employee perks.

You might understand how pool tables, tuition reimbursement, and office snacks can impact employee engagement, and how it fosters a happier workplace which, in turn, leads to happier customers. But how do you convince your boss of this? How can you persuade management to consider any of your ideas?

It requires more than simply presenting a series of facts. Thorough planning, the right timing, and understanding your audience are all key factors that go into successfully persuading your boss to say yes. 

How People Make Decisions – Start with Why

Decisions aren’t made based purely on rational thought. While it might seem that way, it’s the emotional side of our brains that creates an initial sense of desire for something, then rational thoughts help justify our decision. This is the concept behind Simon Sinek’s book Start With Why.

In the book, Sinek explains that people are motivated to take action by a sense of purpose, their “why”. This video aptly summarizes the concept. It explains that people don’t buy and make decisions based on what you do, rather it’s why you do it–because that’s where the emotional connection lies.

Persuade management by starting with Why

For example, if you’re buying a car and don’t get a good feeling about it, all the rational thought in the world won’t persuade you to purchase the vehicle. But if the car gives you a good feeling, rational thoughts such as “it’s safe” and “it gets good gas mileage” will help convince you to buy it.

You can use this same principle in any situation that requires persuasion, including getting buy-in from your boss. Other factors that impact decision-making include the circumstances, context, and timing. 

Convince Your Boss to Say Yes – 5 Tips from Expert Sources

1. Harvard Business Review – Get The Timing Right

In their article Get The Boss To Buy In, authors James Detert and Susan Ashford explain how the timing of your pitch can impact the final decision:

“It’s critical to find the right moment to raise your ideas. That moment might be when organizational priorities shift, when certain players leave or join the company, or when a boss’s preoccupations change […] The best sellers notice when more and more people are beginning to care about a larger topic or trend that’s related to their issue, and they position their idea to “catch the wave.”

2. Sharlyn Lauby – Find a Champion

Sharlyn Lauby is an experienced Human Resources professional and consultant who manages HR Bartender, a resource that covers any and all topics that relate to workplace management. As someone well-versed in tactics to help deal with management, she offers sound advice in this article, including:

“Identify who is the best champion for the project or initiative. Part of a project’s success is choosing the right champion or sponsor.”

3. Lolly Daskal – Know Your Audience

Understanding what makes the management team tick will help you tailor the delivery of your idea. Take it from Lolly Daskal, one of the top leadership coaches in the world, in this blog post of hers:

“Persuasive people make it a point to know the people they are speaking to. They learn who they are and study their preferences. They would never give a high-board vision to a person who likes details, and they wouldn’t speak in declarative statements to a person who values collaboration. The more you pay attention to the sweet spots of others, the more you can tailor your message to their preferences.”

4. Dan Rockwell – Plan Your Presentation

How well prepared you are when you present your idea to senior management will impact their perception of it. Dan Rockwell, also known as The Leadership Freak, emphasizes the need to plan your presentation:

1. Tell a brief story of how others are struggling, disappointed, or frustrated. Describe the problem or opportunity briefly, simply, clearly, and with compassion.

2. Describe a solution.

3. Define specific deliverables.

4. Explain timelines.

5. Request resources.

5. Deborah G. Reigel – Think of Unintended Consequences

In her article 3 Questions to Ask Yourself Before Pitching an Idea to Your Boss, Deborah G. Reigel, an expert in communication and leadership skills, emphasizes the need to think about all the ways it will impact the business. For example, if you want to implement a new employee perk, who will be responsible for managing it? How much time will that take away from their current responsibilities?

“Make sure you think about unintended impacts up, down and across the organization, as well as for key stakeholders outside the business, who may not experience your great idea as all that terrific.”

Your Boss Said No. Now What?

It’d be nice if your boss loved all of your ideas. But, as you know, the world doesn’t work that way. Sometimes, despite playing all your cards right, your boss will still say no to your idea.

It can be a hard pill to swallow. When someone tells us no, we often take it personally. So where do you go from there?

First, try not to feel defeated. Once defeat sets in, we tend to reduce our efforts. Second, ask your boss questions:

  • Is there any aspect of the idea you do like?
  • Can we revisit the idea in the future?
  • Can I improve the idea and make it better?

No doesn’t necessarily mean never. Use the decline as an opportunity to get creative. What other perks could you offer employees that aren’t as costly? What can you do with the resources you have to improve engagement in the office? You very well could surprise yourself.

employees playing with dog at work

Dogs in the Workplace: A Quick Guide to Office Pet Policies

As companies look to offer employee perks that will attract and retain top talent, pet-friendly office policies have become popular. You don’t need to scroll too far in your social media news feed to see a picture of someone with their dog at work. But bringing your pet to the office is more than a marketing gimmick used to lure job candidates. There are some real advantages to be gained.

While you might want to jump on the bandwagon and adopt an office pet policy, it’s important you do so discreetly. A flippant approach will only result in problems. It’s important to stay informed of the benefits and procedures for allowing dogs at work to avoid any issues. The following blog post serves as a resource to help you make the best decision for your office. 

Dogs in the Workplace are Nothing New

Dogs have always had a place at work:

  • Fire Department Dogs
  • Dogs in garages/auto-shops
  • Search & rescue dogs

The circumstances and reasons for having dogs in these professions are obviously different. They help rescue people and save lives in ways humans simply can’t. That doesn’t mean bringing dogs into an office setting doesn’t have advantages. In fact, it’s quite the opposite.

Benefits of Dogs in the workplace

1. Make you take necessary breaks

Sometimes we get so busy at work and don’t even realize how much time has passed. That’s not good for your mind or body. The risk of heart disease, dementia, diabetes, and other health concerns increase as a result of sitting too much. If you bring a dog to work, you’re forced to get up and take them outside for a quick walk.

2. Reduces stress

Workplace stress is a real and constant issue for many people. Dogs offer comfort and companionship which, according to studies, can help reduce stress at work.

3. Brings People Together

Dogs in the workplace help foster healthy working relationships among employees. They present a common ground for people to connect, one that is positive and can help boost morale in the office.

Additionally, bringing dogs to work help increase productivity and employee retention. Not to mention it keeps dogs from being alone at home all day. Sounds great, right? Before you implement a new policy, however, consider these helpful tips for establishing one that fits your office.

5 Tips to Establish a Successful Pet-Friendly Office Policy

As mentioned above, you can’t just suddenly declare pets are allowed at work. It’s a surefire way to cause confusion and chaos among employees, which is the opposite of what you’re trying to achieve. Do your research and plan well enough so that when you do implement the policy it’s successful. Here are five tips to help:

1. Make sure everyone is on board.

Most people in your office might love pets. But it’s important to speak with everyone regarding their feelings about bringing dogs to work. Someone might be petrified of dogs. If that’s the case, moving forward with a policy would not serve in your best interests.

2. Know the risks.

What happens if someone gets bitten? Although it’s unlikely, it is a real possibility and one that should be considered seriously. Check your insurance plan.

3. Is your office pet proof?

Once you determine employees are onboard with bringing pets to work, you must make sure the office is pet proof.  Some things to consider include:

  • Space for introducing new dogs to each other
  • An outdoor space for dogs to relieve themselves
  • How can pets be contained if their owners need to step out?

4. Set up rules.

It’s important to establish a set of rules for how employees will manage their pets in the office. For example, pet owners should come prepared with their own food and bowls for water. Determine protocol for when a dog starts barking too much. Establishing these guidelines will keep everyone on the same page and make it easier to manage situations if they arise.

5. Have everyone sign the policy.

Once you’ve finalized the new pet policy for your office, print it up for everyone to sign and keep it on file.

Bringing dogs into work is a fantastic employee perk. The benefits are numerous and it can have a lasting positive impact on your office culture. But the execution of the policy must be acceptable for everyone to create a happier workplace.