Convince Your Boss: 11 Tips to Make Them Say “Yes!”

Convince your bossImplementing new ideas in an organisation is challenging for many reasons.

From internal politics to bureaucracy to lack of time, there are many obstacles to face…

Yet, every company needs leaders like you to make sure the organisation constantly evolves and continues to innovate.

Here are my 11 most effective tips to persuade your boss.

People who’ve used these tips got their boss to implement new ideas, to buy new ideas, and to get more flexible work schedules.

Warning: you are NOT going to find anything about being a bootlicker (dull) or working hard (boring) here.

Now that you’re ready:

Let’s go more in depth and explore each of these 11 means that will make it easier to convince your boss to try new things.


1. Frame your suggestion to match their goals

If you get this first tip right, you’ve got 80% of the job done.

We all think about what we want first—e.g. a new coffee machine, attending a training session, or working from home. But this is not how your convince someone.

Take this approach instead:

Frame your suggestions in terms of how it might help your boss. Here’s what matters to your boss: improving how your team performs, generating more revenue, or simply making your boss look good.

Your boss wants to know how your idea can help him achieve his goals. For this you need two things:

  1. Understand where your boss wants to be—his goals;
  2. Find how your suggestion can help your boss get there.

Here’s an example about remote working:

What you should say if you want to start working remotely once a week? Don’t explain that it will save you the commute time. Highlight that you can start working one hour earlier. Show the benefit. It means that you can get all your tasks done one hour earlier. This benefit alone may be enough to get your boss to agree on giving it a try.

Putting yourself in your boss’s shoes may help you discover that there are actually better ideas to suggest.

Frame your solution from your boss’s perspective, not yours.

I’m using the term ‘boss’ for the sake of simplification. I should say: ‘decision-maker’. In a flat organization—like most small and medium businesses—the person you need to convince is often not your boss but a colleague who has some higher responsibility on a project or an activity. So you need to solve their problems first.

What are their goals? What will get them promoted? What do they need to do to succeed?


2. Pay extra attention to your boss’s problems

It is natural to start thinking about how to solve your own problems. “If I could automate this task, it would make my life so much easier.”

New ideas often arise from problems you’re having in your daily job.

So it’s easy to focus too much on your own problems.

Your boss does not really care about making your life easier—well, to a certain degree he does, but there are limits. Instead of presenting an idea as a way to make your life easier, frame it as a way to make yourself more productive.

This is an example of empathy.

The more you understand what your boss wants, the more chances you have to persuade him. (To know why, read this article about the power of empathy.)

Instead of considering your problems first, look at the world from the perspective of your boss. What is bothering them? Why can’t they get what they want? How can you solve their problems?


3. Build the reputation to be a great performer

Decision-makers have more trust in great performers than with average employees. That is natural. Heroes get praise and attention.

In an organization, what I call the ‘hero effect’ is similar to how brands impact consumers. The more you see and hear about it, the more you trust it.

Even though performance is a factor of how people perceive your personal brand, the hero effect also depends on other factors.

Jeffrey Pfeffer, in his amazing book Power, highlights with sarcasm that, as long as you keep your boss happy, performance doesn’t matter that much:

“Make sure that those in power notice the good work that you do, remember you, and think well of you because you make them feel good about themselves. It is performance, coupled with political skill, that will help you to rise.”

Getting noticed is primordial. The best way to get your boss’s attention is to pay particular attention to what your boss cares about.

If you are looking for inspiration, besides reading Power, I recommend that you read Tribes. In this book about leadership, Seth Godin explores many stories of people who leveraged the Internet economy to have a significant impact within and beyond their organization.

Keep in mind that bosses are more likely to consider ideas from those they see as the highest performing people on the team. It not only depends on your efficiency but also on how your boss sees your result.

Building a good reputation takes time. Be patient and start progressively. Match the size of your suggestion to the quality of your reputation.


4. Take advantage of the FOMO

Most organisations are (very) conservative… You know that.

People don’t want to risk their reputation. And they avoid any bold decisions. What they love to do is killing new ideas—it’s so easy to do.

Here’s what you can do:

Create a sense of urgency. Comparison is a great tool for that. Mentioning the competition triggers a fear of missing out (FOMO).

FOMO is a scientifically proven phenomenon. Dr Andrew K. Przybylski, research fellow at Oxford University, defines it this way:

“A pervasive apprehension that others might be having rewarding experiences from which one is absent.”

You can make a strong case by establishing that some competitors have implemented a similar idea with success. Nobody wants to stand behind the competition.

On the other hand, success stories are reassuring. Using a simple syllogism is helpful. As we are constantly dealing with uncertainty, we need to make shortcuts in our reasoning. Coming up with sound logic is enough to convince someone that your idea is good.

Look at organizations in an other industry that are using your idea. It does not mean that implementing your idea will be for sure successful in your own company, but it is reassuring for the decision-maker.

Saying: “A friend at Amazon has done that for six months and his team has been able to increase their performance by x%” sounds like a compelling case.

Referring to respected organizations will support your ideas. Bonus if you find companies your boss respects that already use the idea you have in mind.


5. Look for ideas in business books

Business books are full of new ideas and illustrations. This has led me to become a business-book freak.

If you explore the business section of a library or a book shop, chances are that you can spot books that can help support your case.

If you want to modify some practice in HR, there are a few books written by Googlers about how Google has shaped a unique culture. I’m not saying they are sharing an easy path to success, but these examples are helpful to support your suggestions.

Getting your boss to read these books is another issue. It is unlikely that she will have time to read it. In such a case, I will read the book, make a one-page summary, and share it with my team.

Reading the relevant books will help you be better informed. You’ll be prepared to answer some tough questions and have examples to support your suggestion.

Some other good books are negotiation books. They teach you how to persuade other people. Pitch Anything by Oren Klaff will teach you the nuts and bolts of persuasion.

You might even realize that perhaps it was not such a great idea after all. And you can come up with different ways of solving the problem you have in mind.

Find educational content (blog article from a reputable source, books, or scientific articles).

Learn more: Explore this reading list full of insightful non-fiction books


6. Build a community

Bottom up rather than top down.

If your suggestion is really beneficial to your company, you shouldn’t find it too hard to convince some of your team members to endorse it.

Provided that your boss respects their opinion, their interest should support your ideas.

Build an internal network. If you’re not alone to suggest an idea, it will have a larger impact. Think about how it can help your coworker. How it can be useful to them. If possible, try the idea at a low cost to them. Invite them to use the software you want your organization to adopt. Talk about it in an informal discussion over a cup of coffee.

In some cases, it might even be better if someone other than you makes the pitch. If you have a good relationship with the peers of your boss, especially peers they respect, consider trying to get them involved.


7. Know how to pitch it to your boss

Pitching is the key moment when you want to persuade someone to try new things. It is similar to conveying a new project. You are putting your idea and yourself in front of other people. It sounds scary but that is the only way to make it real.

The format matters. You need to know what your boss likes. Should you discuss it informally during a coffee break? Should you organize a meeting with other stakeholders? Should you first write the idea in your internal collaboration tool?

Remember… people respond differently to pitches when they are in front of a group than when they are alone. So you need to find the situation that provides the best opportunity, based on what your boss likes.

You can observe how other people pitch your boss and what tactics seem to work best.


8. Leverage objective data

Data doesn’t lie. But it’s sometimes difficult to understand.

Here’s how you can convince using data:

Using data to tell stories. I’m a big believer of the art of data visualisation. And the reason is that smart marketers use it all the time to make people see the world in a different way.

In a large organisation, finding the data is super easy.

You can find lots of data in your company’s online analytics and CRM. Have a chat with the accounting department and use financial reports. These two sources give you precious info on how your customers behave and how your company performs.

If you’re still in an exploration phase, there are tons of things you can do. For example, you can leverage user research. Interview several users to understand objectively in what context your idea will take place. Record their reaction in audio or video.

9. Derisk the decision for your boss

Low risk, high reward. These are the perfect attributes of an easy decision to make.

The reward is how helpful your idea is to your boss: To what extent does it help him achieve his goals? Or solve one of his problems?

The risk involves cost, likelihood of failure, and effect of failing.

The lower the risk, the more convincing your idea will be.


10. Do a low-cost experiment

Low-cost experiments are a great way to minimise risks and lower the cost to a minimum.

Here’s an example:

If you want to start using a new software application, start with a free trial. We are recording new videos to show what the new version of a software can do for your team. David Plath is in charge of that. He felt that he did not have the proper tools to produce the videos, so he started a free trial of Adobe Premiere Elements. When the free trial is over, it will be easy for David to ask us to buy the software. He will just have to show the result.

Free trials are awesome. That’s also a reason why you can Evernote adopted a freemium model.

You need to find a way to measure the experience. Monitor the difference of using it or not. Highlight promising results when you are using this new software. Define a list of criteria in order to evaluate if the trial was successful.

As a marketer, if you want to use a new segmenting tool compare similar campaigns you did with and without the tool. That’s what I did to show how useful Moz can be to design our content marketing strategy.

Adopting a new method of doing certain tasks is not so different. It does not cost money, but rather people’s time and willingness to change—and with this comes a sense of risk.

Choose the safest way to test your idea. Limit the risks.


11. If your boss agrees to give it a try, do everything you can to make it work

Implementing a new idea requires extra effort, especially at the beginning. It takes a lot of time before something becomes habit in an organization. You can’t just assume that because your boss said yes, everyone will follow her recommendation, especially if she was skeptical and you had to make an extra-commitment to make it happen.

I know of some instances in which the boss herself wanted to implement a new idea, everyone gave it a try because the boss asked. Yet, it did not work. Habits are so powerful.

Once your boss has agreed to give it a try, you need to do everything your power to make sure that it will work. Otherwise, it will be tough to convince your boss the next time. Your future reputation is on the line.

This might require to do some of your colleagues’ work for a while. You want to make it easy for them to adopt the new idea. Send a weekly summary showing showing them the results and encourage them to use them to use the new method. Ask often if they need help. Do everything in your power to make sure that everyone likes it.


Takeaway on How to Persuade Your Boss To Try New Ideas

I hope you’ll use these tips to make stuff happen in your company.

Keep in mind:

Focus first on what you want to achieve and why. Once you have an answer to these two questions, find out how this can help your boss and the rest of the organisation.

This will help you convince your boss to try new ideas.