How to Get a Yes From Your Boss

It can be challenging to get your boss to sign off on new technology needs for internal communications. Here are some tips & tricks to get the tools you need.

Hands up if you find it easy to ask your boss for something that you need, and feel confident that you’re going to get it.

If you raised your hand, this article isn’t for you. You may also live in an ideal world, and if so, let us know what it’s like!

For the rest of us, limited budgets and the wrong tools in the workplace tend to be something that people are unwilling – or even afraid – to change.

So if you’ve ever wondered how to convince your leadership to say yes to the tools that you need, then read on for our insider’s guide on how.

That Sweet MoSCoW Method

Say you’re interested in pitching your boss on the idea of a new communications technology.

Inherently, the question that your boss is going to want to know the main answer to is how does the technology you’re asking for help you to meet the business’ needs?

This is where composing your proposal using the MoSCoW method can help clarify your points.

The MoSCoW method allows you to break down a project into:

M – Must have this requirement to meet the business needs

S – Should have this requirement if possible, but project success does not rely on it

C – Could have this requirement if it does not affect anything else on the project

W – Would like to have this requirement later, but delivery won’t be this time

Rather than offering an uncompromising take – we must have this or everything will fail, it helps to present to your boss these four points.

Your aim is to show your boss how this is going to make life easier for employees, and in return, help employees save time (and as we all know, time is money.)

Make sure you’re asking the right questions of the technology you’re proposing – these answers should be clear in your mind before you even pitch your idea to your management.

Find Your Allies

Before you even consider starting your sales pitch to management, it helps to raise the issue with other people who work around you.

These don’t necessarily need to be people based in your department – in fact, reaching out to people in other departments can actually help you to improve your proposal. In the case of new software, ask how they are running their systems, and whether or not they could they benefit from the software that you’re interested in. Would they be interested in endorsing the change too? It also helps to have people across departments helping you lead the way to change, and increases the likelihood of your managers approving it.

Make sure you listen to any questions they have that you hadn’t thought of. It’s likely that they might come up with a concern or a difficulty that you hadn’t considered, and will allow you to pre-empt any of your boss’ concerns.

Finally, take a look at the vendor’s website, or on social media, in order to see what other users have said. Have they noticed a particularly strong point of the software that hadn’t occurred to you?

Make It Easy To Say Yes

Your boss is a busy person, so when you’re making the case for your proposal, you want to make it as easy as possible for them to say yes. You can’t expect to send in a 60-page report with appendices and expect them to necessarily be able to slog through it.

Instead, use the power of the introduction or executive summary.

Your executive summary should be around 100 words, little more than a paragraph, which explores how it is that your proposal is going to make life better within the company.

Take again the idea of a new internal communications system.

You want to show your boss that the platform is going to improve employee engagement, reduce time spent, and therefore reduce costs to the company. Don’t get bogged down in doing too much of a hard sell or explaining the minutiae of the software.

Provide them with a context: here is the problem, and here is the solution.

Show Them The Money

It’s important to show your leadership that you understand that things cost money. They may be reluctant to take on a new idea on the back of prohibitive costs.

So show that you understand that new technology may have a cost to it, but that this is something which is easy to mitigate.

Find out the budget that your department has from your sales department. Then see what it is that the vendor is willing to offer you in order to make a deal – is it free training? Or perhaps they will give you a reduction if you’re willing to be a case study. Negotiation is an important key to handling the financials, and in showing that you know how to get the best quality for the lowest amount.

Remember the allies you made in asking for information and providing a context? See if their departments would be interested in cost sharing so that they can have the programme for themselves.

Failure Is Not The Be All And End All

If your boss is concerned that your project might fail, it’s important to concede that yes, it might.

However, show that this is something you have factored into your planning. Suggest, if the costs seem prohibitively high, that you pilot a scheme in a department rather than running your idea company-wide. This will show that you are interested in getting the running of the project right before it becomes widely used.

This will also allow you to show evidence that is tailored to your company and your company’s needs and will allow you to present an even more powerful case to leadership.

Wow With ROI

Your boss cares about tangible benefits in terms of time. A great way to show this is to highlight the tangible benefits in terms of time and money.

Present your boss with a specific ballpark figure.

One way to really bring this home is to use an analogy of something you’ve seen in industry trends. Say you’re interested in a service like Cerkl, which uses AI to find more relevant content for users. Your boss may not understand what this means.

Tell them it’s like Amazon for Data, and they’ll start to get it. Show that the AI will decrease the time staff spend looking for content, which increases their productivity, and improves over time in order to save them money. This is something they’re far more likely to understand.

Next time you enter that meeting with your boss remember to present the problem with your solutions, show an understanding of cost, and how this provides ROI. Good luck!


This article was inspired by a webinar called Building the Case to Drive Change hosted by our sponsor, Cerkl. It was featured John Twombly from St. Louis Children’s Hospital and Reagan Stafford-Tarin, former Internal Comms Pro & current Account Executive at Cerkl.