Getting a “YES” from Your Boss for More Resources: A How-To Guide

We need another staff member.

We need more advertising dollars.

We need a new website.

We need updated collateral.

We need another software platform.

Sound familiar?

The marketing landscape evolves quickly, and leadership expects results. It’s no wonder needs pile up quickly — during budget season and all throughout the year.

The challenge isn’t recognizing the need; it’s convincing someone else to invest in it.

I’ve been there. 

Earlier in my career, I served on — and later led — marketing teams, passionately explaining why our department needed more people, more dollars and more tools. 

Today, as a vice president, I’m evaluating those same requests before deciding which ones move forward to our CFO and college president. 

Every budget season, I review requests that all have merit, but only a handful can move forward. 

Here’s what I’ve learned: Getting a “yes” rarely depends on how important your request feels to you. It depends on how well you help leadership solve a larger institutional problem.

So, where to start?

Here are the four steps I’d recommend every marketing professional take to improve their chances of hearing “yes.”

Step 1: Before You Ask for More, Evaluate What You Already Have.

I know what you’re thinking. This article is about securing more resources, not cutting costs. But hear me out.

The first thing I ask my leaders in my division to do before making a new request is to evaluate their current state of operations. 

People. 

Capacity. 

Software.

Budget. 

Projects. 

Efficiencies. 

In my experience, this type of reflective exercise often uncovers creative solutions that move the needle toward higher priorities. Higher education operates with finite resources. Being a good steward of these resources isn’t just good leadership; it’s an expectation.

For example:

• Can an existing position be restructured to better align with evolving institutional priorities?
• Are there products and software that no longer serve the department, or a similar one with a better price tag?
• Are there projects that your department is still carrying that can be sunset in favor of higher priorities?

By doing a similar analysis, my Director of Marketing recently transitioned to another news monitoring service and saved more than $10,000 in her upcoming budget. She was able to then use those savings to augment her digital advertising budget for targeted mini enrollment campaigns. The request for additional advertising dollars didn’t disappear; it simply became smaller because existing resources had been optimized first.

Through reflection, she also restructured a vacant position into an assistant director role for added leadership support, and the restructuring equated to a near net-neutral budget change.

As an executive, these are the kinds of discussions that immediately capture my attention. Leaders who demonstrate they’ve exhausted existing resources before requesting new ones establish credibility. Their future requests carry more weight because they’ve already proven that they are responsibly stewarding the resources they’ve been entrusted with.

Step 2. Align Your Request with Institutional Priorities.

I always tell my team, “If we cannot tie it back to our college’s strategic plan, why are we doing it?”

What institutional problem are you trying to solve?

In the case of a new website, it’s not about an aesthetically pleasing landing page or a slick photo carousel. Think like an executive. Rather, state your case with a clear line of understanding of the bigger picture:

Weak pitch:

“We need a new website because ours is outdated.”

Strong pitch:

“Our current website creates ADA compliance risk, negatively impacts enrollment conversion, increases maintenance costs and limits our ability to support strategic enrollment initiatives.” 

See the difference? The conversation is no longer about spending money on a website. It’s about reducing institutional risk, improving enrollment outcomes and advancing strategic priorities. That’s how executives evaluate investments.

Step 3. Show Me the Data.

A good idea may start the conversation, but data is what moves a request toward the finish line. 

By this point, my marketing director has already demonstrated that she’s been a responsible steward of existing resources and aligned her request with institutional priorities. Now I want to see the evidence. Can she prove the investment is likely to produce meaningful results?

• Can you connect advertising click-through and conversion rates to enrollment? 
• Can you demonstrate that your media strategy outperformed industry benchmarks? 
• Can you show that investments in SEO and keyword search increased inquiries or even produced a waitlist for a program?

Think like an executive. Every investment competes with dozens of other worthy requests. What is the return on yours?

The stronger your data, the less your ask feels like a gamble and the more it feels like a sound investment.

Step 4. Make Saying “Yes” Easy.

Your goal isn’t simply to make a request. It’s to make it easy for your boss to champion your request.

My marketing director has completed all three steps, and I’m certain that she’s bringing it home with the fourth step: Make it hard for me and my boss to say no.

What I mean is—be impressively prepared. Provide your boss with a toolkit that they can confidently walk into the president’s office with tomorrow. The easier you make it for them to advocate on your behalf, the more likely your request is to gain traction.

• Have a timeline prepared.
• Gather vendor quotes.
• Bring data on peer institutions and other benchmarks.
• Articulate implications on staffing.
• Draft a metric-driven implementation plan.
• Anticipate objections.
• Identify consequences for delaying the decision.

This last step will separate your ask from many others. This is where good requests become compelling business cases. You are proving that you are ready, the plans are laid, and you only need a “yes” to begin the work.

Think like an executive. Every request is evaluated through three lenses: risk, return and strategic alignment.

The next time you’re preparing to ask for another position to hire, a larger advertising budget, or a new technology investment, remember these four steps. Demonstrate you’ve been a responsible steward of existing resources. Align your request with institutional priorities. Support it with data. Then make it incredibly easy for your leadership to advocate for it.

Executives don’t fund good ideas. They fund well-prepared, strategically aligned institutional investments. The more you learn to think like an executive, the more likely your executive will think “yes.”