How to Convince Your Boss You Need a Software Upgrade

We’ve all been there. The software you use at work is at the end of its life. You know it, your co-workers know it, and your entire department knows it.

Unfortunately, there’s still the issue of making your boss see the light.

The main issue with corporate software, right or wrong, is your boss likely has more pressing issues on which to spend money.

While this isn’t what those of us struggling with outdated software on the job want to hear, your boss has to worry about priorities such as making the payroll and increasing profit margins.

It can be downright daunting to approach your boss with a request for new software, even if it’s completely necessary.

According to a Harvard Business Review article, the inability or unwillingness of employees to speak freely to their bosses is one of the biggest problems workplaces face.

All this means is your boss really needs to be persuaded in a way he or she can’t say no.

In other words, you have to pull out all the stops to make the best case possible why a software upgrade should be at the top of the list of business priorities.

Here’s how to do exactly that.

Let Numbers Do the Talking for You

Many bosses are bare-bones numbers people.

They want to quantify the specific reason behind decisions such as spending a lot of money on a software modernization project.

So give your boss what he or she is looking for: tangible numbers that can’t be ignored.

After all, your boss spends time on the job analyzing problems, looking at potential cost savings, and quantifying the return on investment for any project.

Speak to him or her in their work language.

For instance, if one of your biggest reasons is that a software upgrade will increase workplace productivity, then get specific with actual calculations.

Present projections of how much will be saved if you modernize your software.

If outdated software is causing inefficiencies, talk about how much money your department is actually losing because you can’t video-conference as quickly or because your email keeps crashing.

As the HubSpot blog puts it:

“Clear, specific, goal-oriented reports serve as one of the most effective ways to communicate your progress and prove to your boss that you’re capable of taking on more.”

If you feel strongly about the need for a software upgrade then focus on the numbers that really matter to your boss, like ROI.

Enlist Support

When more than one voice advocates for a software upgrade, the pitch will be better received by your boss.

Strength in numbers helps your credibility and your cause.

No matter what department you’re in — IT, sales, accounting, etc. — having others voice similar concerns about your inefficient software is a unified voice that’s hard to ignore.

Instead of going to battle alone, enlist a supervisor, a manager or even a VP from your department to help make the case.

Not only does this present a unified front, but it adds the gravitas of a senior position to boost your credibility.

If just one employee asks for a software upgrade — no matter how well-reasoned — it still won’t carry as much weight as an employee joined by others.

Create a Presentation for Implementation

This goes back to how your boss likes accuracy and facts.

Asking for a software upgrade will be easier if you can outline the what, why and how.

When requesting to modernize your software, include the following points in your presentation:

• Reasons for the upgrade
• Potential options and solutions
• The process and cost implications of each possible solution
• Suggestions on how to handle and mitigate potential risks during the upgrade

Give Yourself and Your Company Plenty of Time

Don’t let your software completely fall into disrepair before making your request.

While your boss can’t argue with an upgrade when the existing software’s on the fritz, it reflects poorly on you for waiting until it’s already too late.

Anticipate how much longer your quality of work can be maintained before your outdated software dramatically impacts your efficiency.

Look for warning signs of software not being able to perform as it should or becoming obsolete, such as:

• An inability to scale along with the growth of your business or department
• Failure to easily integrate with other company systems like accounting or email
• Difficulty in being able to centrally track and manage your customer data

Any of these problems is already reason enough to realize your software isn’t in the best shape and to begin to brainstorm how to approach your boss about the necessary software upgrade request.

Make a Comparative Argument

Make your request for a software upgrade an analogy to another recent business investment.

Embedded in this context, it will be more palatable to your boss, especially if he or she looks at software as a necessary evil.

If this is the case, then compare the software upgrade to a business investment like a new machine for the factory or a new fleet of vehicles for transportation.

Framed this way, it may help your boss see its value better than ever.

Focus on the Benefits

By stressing the direct benefits of a software modernization project, you can turn a potentially hard sell and into something welcomed with open arms.

For example, if your current software is so outdated your IT team is fully enveloped just maintaining it, then stress the potential value from an upgrade.

With less stress on your IT team, they may be able to focus their attention on what your business really needs.

Another situation relates to time.

How many businesses would kill to speed up operations and without increasing the payroll?

Old and outdated software slows down your organization by forcing needless manual repetition or by taking excessively long to perform basic functions.

Since time is money, losing time means an organization also loses money when old software performs poorly.

Focus on the software upgrade increasing business efficiency as another key selling point.

Look Into Government Grants

It may be possible to use grants from the federal government to cover the costs of your software modernization, which makes for an even easier sell to your boss.

The federal government currently offers grants through a program called the Small Business Innovation Research Program.

In short, this opportunity funds small businesses looking to bring high-tech products to market, thereby helping them compete with bigger businesses on a more level playing field.

If you can demonstrate to the federal government that your organization meets the criteria to receive this seed money, then you can use a portion of it to pay for the software upgrade.

Vital to Your Business

Your software is vital to your company.

Unfortunately, it can sometimes be an uphill battle to convince higher ups that don’t necessarily use it on a daily basis.

Some bosses may not appreciate the true value of software to your organization.

Sometimes, it’s just the industry you’re in, but other times, it can really be that your boss just doesn’t value or understand how critical efficiently working software is to the business’ bottom line and employee morale.

That’s why it’s up to you to make this happen.

With these seven winning strategies, you’ll have an easier go at making even the most difficult boss appreciate the value behind a software upgrade.

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