How to Convince Your Boss Based on Your Personality

If you’re thinking about getting certified as a Product Manager, one of the factors you’ve undoubtedly considered is how to fund your studies. Which means you’ve thought of asking your boss for help. After all, they’re the ones who will benefit from having upskilled employees. When aiming to convince your boss that paying for your certification is a good idea, there are a few key things to keep in mind:

  • Most big companies will have a budget for employee training. Most of the time it goes unused as employees don’t think to ask for training.
  • It’s not out of the ordinary. You’re not going to shock and horrify your boss by asking for funding, as it’s a well-known phenomena. And remember, it’s not coming straight out of their personal bank account. The worst case scenario is that they’ll apologise, and say that it’s not in the budget. You’ve got nothing to lose by asking.
  • A big number to you is not a big number for your company. To the average person, $5,000 is not a small sum. When the average US startup is worth $4.2 million (in San Francisco and Silicon Valley this number goes up to $5.1 million) suddenly that number seems much smaller. Some companies can spend up to $11,000 just on a team building afternoon! Think about the fee from a company’s perspective, not a personal one.

Ok, so now you feel fully justified in asking your boss to help fund your education! Before we dive into how to tailor your approach to your personality, there’s a few basic do’s and don’ts that everyone should adhere to…

Convincing the Boss 101

Think about your Boss’ personality

What kind of things do they value? If they have a history of being a bit tight with resources that aren’t absolutely necessary, you’ll need a different tactic than if you’re dealing with a boss who values investing in employees. If they are the latter, you’ll need to bring extra data to back up your argument. With the former, you’ll need to tap into your soft skills like persuasion and communication. The trick will be not convincing them that funding employee training is valuable, but why you specifically should be that employee.

Communication methods

In either case, approach the topic via written communication first. Send them an email (not too long) briefly detailing what you’d like to discuss with them. Include the brochure for the certification you have chosen so they have something to refer to. If you’re lucky and have a good rapport with your boss, setting up something informal will take the pressure off slightly. “Could we possibly have lunch/coffee together today and go over this?”

Don’t lead with the cost

Starting your pitch with the price tag is not the way to go. Imagine walking into the Apple store, and being greeted by an employee saying “Hey there, can I help you spend $1,299 today?” You’d instantly be thinking about the cost rather than what you were planning to buy. If you lead with the benefits, you’ve already captured your targets attention and placed it firmly where you want it to be. By entering negotiations with the cost upfront, you’re automatically in a defensive position trying to justify the investment.

Don’t try to hide the cost (if they’re paying for it, they’ve got to find out eventually!) but try to slip in as many positives as possible before the price is revealed.

For Your Personality

Ok, so now you’ve got all the basics covered, it’s time to think about how your personality type will affect your pitch. Every student is different, which means there’s no One Size Fits All way to make your case. Use your strengths to your advantage by thinking about who you are…

The Mathematician

Who you are: You love playing with numbers. You have a very logical approach to everything. Perhaps you’re looking to transition into a Product role from a Data role, or you’re a data-focused PM looking to grow. You like seeing the evidence in black and white in front of you, and that’s going to be a great asset in convincing your boss.

How to convince your boss: Numbers are your business’ lifeblood, which means they’ll be your bosses’ best friend. Use them to your advantage. “According to research, a full stack product manager can increase company profits by 34.2%. You can apply this statistic to an area of product development which a certification would improve on. “By improving customer retention we can increase revenue by X%.”

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The Leader

Who you are: You’ve earned respect in your role by being a proven leader. You manage your teams with empathy and a firm-but-fair attitude. Your greatest strengths are your skills of communication, team management, and you run a meeting like a tight ship. You don’t want people to feel like they’re there just to finish tasks and go home. You value everyone’s input and want them to feel valued.

How to convince your boss: The strength of a team can make or break a product, and therefore make or break a company. And although many may not like to admit it, that involves some hardcore soft skills. You need to be your most persuasive self, adept at managing stakeholders and be able to lead effectively without formal authority. This is what you should put across to your boss.

Have a think about recent conflicts either within your team or across multiple teams. Explain the negative effect this had and stress how you believe being trained in product leadership will help you avoid these setbacks in the future. If your boss is very numbers-focused, try to bring some data with you to back up your claims. Exactly how much time (hence money) was lost.

As you’re a team player, you can also emphasize how you’ll make your studies work around your responsibilities on the job. Let them know that your studies won’t impact your contributions while the course is underway, and keep the focus on the contributions you’ll be able to make once they’re done.

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The Adventurer

Who you are: Risk taker. Adventurer. Trailblazer. You’re the one in the office who loves to take on new challenges, an out-of the box thinker with proven results. It just doesn’t suit you to do things “just because that’s how they’ve always been done.” Your competitive nature drives you to try some really hair-brained schemes, just so you have the satisfaction of hearing your teammates say “oh wow that actually worked!”

How to convince your boss: You’ve taken leaps of faith before, and they’ve paid off. Use some examples from your past where you came up with a brilliant new idea and got results. As a visionary, you’re probably already full of ideas for how the company could move forwards, and what else your product could bring to the table. Now is the time to whip out the project or feature you’ve been mulling over. Show your boss what a valuable asset you are, and by investing in your education you’ll be able to realize these awesome visions. It’s going to take a great pitch and some persuasion…but since these are core PM skills, you’ll nail it!

You can use your competitive nature to your advantage here. Think about what your competitors are doing, and how (with the right training) you could lead your teams to do it even better!

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The Geek

Who you are: You’re fascinated by puzzles, love cracking codes, and possibly enjoy a sudoku once in a while. You either know a bit of coding, or watch what the engineers do over their shoulders and wish your job looked that cool. Maybe you know the basics and can tell <head> from <body>, but it’s not enough. You want to know more.

How to convince your boss: While it’s not usually a necessity for PMs to have a lot of tech knowledge, most are starting to realise that in a predominantly tech-industry role, a PM could do with knowing at least some HTML basics! Getting ahead of the others and getting trained things like Java and Python will make you one of the most competitive PMs in the business!

One of the most common pain points we see is different teams not being able to talk to each other, especially with engineering. Make the point that being more formally trained will help to solve these communication breakdowns. If you have any specific examples of times tech knowledge would have aided development, now is the time to bring them up. You could even ask members of engineering what they think about having a more techy PM. Their support could go a long way.

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The Mad Scientist

Who you are: In another world, you’d be building robots straight from a film. In this world, you’re a lover of machine learning, fascinated with where this next trend will take us. (Probably the safer career choice, if you’ve seen the ending of Ex Machina). Your heart and mind are set firmly in the future, and you want to be the person to take your company there too. You don’t care about being flash and presenting something with all the bells and whistles to your user, because you know that what goes on behind the scenes is more important.

How to convince your boss: Remember that just because it all makes perfect sense to you, doesn’t mean it makes sense to your boss. Sometimes AI can seem like a very abstract concept which is difficult for the lay person to get their head around. You’ll need to show some real world applications and evidence that this is the future. Start the convincing process by sending your boss some examples of great things being done with machine learning, to share your enthusiasm for it.

Once they have a better understanding of the practical applications of the technology, you’ll be in a much better position to negotiate. This is when you can make the point that you’re going to need formal instruction to get the best out of it! If you need to use your powers of persuasion, you’ve got plenty of evidence to back you up, like the fact that AI is the most rapidly advancing innovations this century.  Perhaps you’re already using machine learning, but your lack of technical knowledge has slowed you down. Use real examples from your role where improved knowledge of machine learning would benefit you, your team, and at the end of the day the company too.

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The Gamechanger

Who you are: You’re a believer in disruption. A Chaotic Good on The Alignment System. You laugh in the face of silos and your number one goal is to do something that has never been done before. Spatial computing and Web 3.0 give you goosebumps when you think about the possibilities, and fills you with the desire to build something now. You want to pursue a certification to be prepared for when the next big thing hits. Maybe you’re already planning what it is…

How to convince your boss: A sensible, forward-thinking company is one that knows it has to adapt to the times. Thanks to technology, so many sectors have been disrupted and continue to grow in massively rapid ways. Let’s actually take the tech industry as an example. Touchscreen phones feel so natural to us now, and have been a game changer for communication. But they first made their truly mainstream appearance with the iPhone in 2007. 12 short years to change the face of communication, and since then we’ve seen innovation after innovation. Voice user interfaces, AI, augmented reality…how can companies expect employees to keep up on their own?

To convince your boss, you can think about disruption in your own sector. What happens when The Next Big Thing hits, and your teams aren’t equipped to handle it? Being as well-educated in Product Management as possible would give you a running start when the next inevitable innovation comes.

Hopefully, your boss is a person of vision, who understands that disruption is inevitable and it’s vital that employees be prepared for it. This will make your job of convincing them to pay for your training that much easier. If they are unfortunately a little old fashioned, you’ll need hard evidence to convince them that the investment is worth it. Look for instances within your teams where a cool feature wasn’t used, or an opportunity was missed. The key is to really drive home the benefits of investing in new technologies.

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The Introvert

Who you are: You get the job done, but you get it done quietly, without making too much noise. The thought of asking your boss to invest in you fills you with just a little bit of existential dread. Asking for “special treatment” feels utterly foreign to you, even though deep down you feel you deserve it.

How to convince your boss: This is going to take some pre-planning. Start out with written communication, like an email you can make a draft of and mull over for a while. You can tinker with it for a few hours and make sure you’re saying exactly what you want to. Your personality type will benefit the most from setting up something more informal. If you have a good rapport with your boss, you could send them a message like “Hi, I was wondering if I could borrow a few minutes of your time this week to discuss something. Will you have some time after lunch?” This is of course entirely dependent on your relationship and also what you think the boss will respond to. If you don’t know them very well on a personal level, maybe try asking someone who works with them more closely for their insights.

We’ve also provided a letter template if you want to skip the face-to-face, or you don’t really know the person who plays gatekeeper to the funds you need.

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The People Pleaser

Who you are: Sometimes you think you’d have made a fabulous psychologist. You love getting into the minds of your users, knowing what makes them tick and how you can solve their problems. Your job satisfaction doesn’t come from seeing the bottom line, but from knowing that you’ve created something that people need, and had an impact.

How to convince your boss: The point you need to make, is that as PM you are the bridge between the customers and the product. You are the one who makes sure that the product aligns with what the user needs not what the buyer wants. If you level up as a PM, that bridge becomes stronger, and at the end of the day filling a need is the most important thing a product can do.

You can also leverage your ability to know what people want by knowing what your boss wants. Figure out what the weaknesses are within the company and see if you learning new skills could be the solution. Maybe there’s a gap for a product manager trained in coding, or there’s a desperate need for cohesive leadership.

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The Completionist

Who you are: You crave perfection, not just in work but in your personal life. You know there are a few gaps in your knowledge, or that there are areas you could upskill, and the thought of being a certified product manager with all the bells and whistles sounds like a dream. You know you’re good, but you want to be better. The best.

How to convince your boss: The important thing is to have a solid list of reasons why this training will benefit your company, otherwise it’ll sound too much like a vanity project. It’s good to be keen, but it has to be for the right reasons to get your boss to open their wallet.

Prepare yourself by making a list of your day-to-day responsibilities, and the things you oversee across all teams involved in product development. Then compare them to the things you’d learn with a certification, and make direct links to how each thing you do would be upskilled with a certification.

Then look at what else you’d receive training in, and create a list of possibilities. For example, Machine Learning could open up doors to new features. Learning about scaling your product and leading through growth could be the starting point for the next phase of your product.

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