Convincing the Boss

Does this sound familiar?

You’ve come to the realization that your current operation is getting increasingly disorganized. So much so that you can no longer track all of the pieces of information you need to in order to manage your job.

But does the boss know this?  Does he/she really appreciate all the moving parts you handle, and how frazzled you feel trying to keep the business machine running?

So how do you communicate your needs to the person who makes the decisions?

When speaking with customers about Tailwind’s transportation software I often encounter the scenario where employees are just overwhelmed trying to use the ‘tried and true’ pen and paper based system. Done with a never-ending series and ever-expanding batch of Excel work sheets to track all of their operations and administration activities.

They just need help. An investment in a tool that alleviates the burden of managing orders, dispatches, quotes, driver pay, and accounts payables/receivables. Clearly, using your computer, instead of your brain, is the natural answer in today’s modern work world.

But before we can sell you a SaaS solution for your truck carrier or freight brokerage business, you need to sell it to your boss.

Here are some considerations to make before you speak to your superior about why they need to invest in Tailwind’s trucking software or freight broker software.

• Believe in yourself – If you are maxed out…you are maxed out.  There are legitimate reasons why your work load is too much for you to manage – it isn’t your personal shortcoming that you can’t remember or manage everything.

• Ask for what you need – Speak and be heard.  Know the message you want to deliver.  Map out your goals BEFORE you start the conversation. Be clear in what you want to communicate and then focus on how you say it later

• Get to the point – do this fast and increase the volume of your voice (ever so slightly). Minimize the fillers we often deploy – “um”  “ya know” “well”

• Avoid devaluing language – “This is just an idea”, “I could be wrong”, “This might be crazy”

• Make a Declarative statement – avoid making your sentences end with question marks

• Believe in yourself – I know this is #1, but I can’t emphasize enough the importance of advocating for what you need at work.  You are the best resource for telling your boss how you do your job and what you need to do it better.

Here’s a sample script:

“We need to track our shipments, so I know where they are, and when they are delivered. We need to improve the time of delivery and reduce our transportation costs. We should streamline our business decisions, improve our efficiency and satisfy our customers. Let’s do more with our resources, scale our processes and grow our company without adding huge overhead. The least expensive option is one that is quick to deploy and has training available. Let’s try Tailwind’s Transportation Software for a month.  The first month is free, we can take a look at the system and see if it fits our business. They have free training and a customer support team that will help us with our technical needs. In this situation we have everything to gain and nothing to lose. I need this and so does our team.”

And if that doesn’t work you can always start to cry.

(Just kidding).

Angelena Helten
Customer Success Manager 
Tailwind Transportation Software