Most organizations today want their employees to have the skills and experience they need to perform their best in the current role. Likewise, some organizations even give their employees an opportunity for training on a skill set they aren’t currently using in order to prepare them for future technology coming. However, there are organizations that just don’t put much weight into training or have much of a training budget. This may be because of a lack of incoming work, or large overhead expenses. Additionally, some training can be expensive with online courses costing up to $3,000, and live in person classes going up to more than $5,000! Smaller organizations can’t afford to send multiple employees to training due to those costs.

The cost barrier doesn’t need to discourage you from requesting training from your employer. Many training organizations offer flexible payment arrangements as well as corporate discounts. Don’t let cost deter you from asking. There are ways to convince your boss to pay for training, and here are a few strategies to try.  

Write a Letter, not an Email

Let’s face it, email is a terrible means of communication and easy to dismiss by the recipient. Yes, you can request a read receipt that puts them on the spot, but it isn’t well received. A formal letter that you hand deliver or send through the company mail channels is a powerful way to convince your boss that they should pay for your training.  Why? Simply because a handwritten letter is more personable and carries more weight in the eyes of the recipient. Feel free to include a pamphlet from the training company and a convincing letter detailing why they should pay for your training.  

Build a Quote and a Case for Training

Asking for your boss to pay for training is just not enough. The best means of getting an approval for training is by gathering all of the details, cost analysis and then building a case for why you should receive financial support for training. Start by working with a training company and gathering all of the pertinent details from them on cost, schedule and payment options. Next, build a case for why you need the training and why it would not only benefit you but the company, as well. Is the company planning on adopting hyperconvergence in the datacenter? Explain how getting training through Nutanix or any other HCI company would make the transition easier for them. It is much easier for a boss to approve a $3,500 training class when they can see what the cost of professional services and support would be through the vendor… spoiler alert, training your staff is cheaper.  

Present the Alternative Methods of Financing

Flexible payment terms can really go a long way in convincing your boss that they should pay for your training or for the team as a whole. Most training companies will work with organizations that want to purchase training on an enterprise wide level as opposed to just on an individual basis. Additionally, negotiate the rate on your own at first with the training company to get the best deal. If you are a veteran or government employee you may get special pricing that would make it easier to convince your boss to approve it. Additionally, you can agree to stay for 12 months after the training if they pay for it, otherwise you will reimburse them in full. Offering to reimburse them helps to lessen the blow of sticker shock that comes with some courses.  

Do Your Own Market Research

There is a ton of information online about training your IT staff and how the benefits far outweigh the cost.  According to, “Employees experience a ‘sticky’ feeling when a company invests in their success by shelling out hundreds or thousands of dollars for training courses designed to improve their skill sets. They feel appreciated and heard, that their employer has (at least some of) their best interests at heart.” Finding reports like this and others from industry leaders will help to convince your boss to pay for your training.

Lastly, a great quote from Zig Ziglar, an accomplished businessman and motivational speaker says, “The only thing worse than training employees and losing them is to not train them and keep them.” If that doesn’t convince them, I’m not sure what would. 

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Greg Stuart is the owner and editor of He's been a VMware vExpert every year since 2011. Greg enjoys spending time with his wife and 3 kids. He has 20 years of IT experience and currently works as an IT Consultant both in the private and public sector. Greg holds a BS in Information Technology and an MBA degree. He currently resides in Southeast Idaho. You can follow him on Twitter @vDestination, read his blog ( and listen to his podcast (