In the creative industry, pitching can often feel like a frustrating, draining process that yields little return on investment. Many creatives are tired of pouring time, energy, and resources into pitches only to walk away empty-handed. However, there’s a strategic way to approach pitching that can dramatically increase your chances of winning, while also protecting your time and resources.
This guide, based on insights from Joel Pilger's conversation with Chris Do on "How To Get High-Quality Clients," will offer actionable strategies and a fresh perspective on pitching. By applying these strategies, you can transform the way you approach client acquisition, improve your pitch success rate, and land higher-quality clients.
(This guide was inspired by this conversation between Joel Pilger and Chris Do)
The Big Misconception: It’s Not Pitching You Hate—It’s Losing
Before diving into specific strategies, it’s important to reframe how you think about pitching. As Joel highlights, many creatives say they hate pitching, but the real problem is that they hate losing. When you’re winning pitches, pitching doesn’t feel so bad. It’s the repeated failures that make the process exhausting.
Understanding this distinction is the first step in changing your approach. Rather than avoiding pitching altogether, the goal should be to approach it strategically so that you win more often—and lose less frequently.
Here are 10 Steps to Winning High-Quality Clients
By applying the strategies in this guide, you’ll be well on your way to transforming your pitch process—and your client base—for the better.
Step 1: Shift Your Mindset from “Order-Taker” to “Expert”
One of the most common mistakes creatives make in pitching is approaching it from an "order-taker" mentality. They view the pitch as a test they must pass to win the client, which puts them in a subservient position. This mindset gives the client all the power, and you’re left trying to meet their every demand—often at the expense of your own creative vision and business interests.
The alternative is to approach the pitch as an expert who understands the client’s needs even better than they do. Instead of simply fulfilling their requests, you guide the conversation, diagnose their problems, and offer tailored solutions. This subtle shift in mindset positions you as a leader and problem solver, making you more valuable to the client.
Actionable Insight:
When entering a pitch, don’t just take orders. Ask probing questions, challenge assumptions, and offer your expertise. For example, instead of simply delivering what the client asks for in an RFP (Request for Proposal), take the time to question their approach. Are they solving the right problem? Could there be a better way? By doing this, you demonstrate that you’re not just another vendor—they’ll start seeing you as a trusted advisor.
Step 2: Qualify Your Clients Early
Not every client is worth your time and effort. One of the most powerful strategies in successful pitching is knowing when to say no. By qualifying your clients early in the process, you can focus your energy on opportunities that have the highest chance of success, rather than wasting time on pitches that were never going to go your way.
Here are some key questions you should be asking early on in the conversation:
How many other agencies or studios are pitching? If the number is too high (e.g., more than five), it may not be worth your time.
Who are you competing against? If the client won’t tell you who the other contenders are, that’s a red flag. Transparency is key to a healthy pitch process.
Who is the decision-maker? Ensure that you’re pitching to the person with the authority to greenlight the project. Otherwise, you could be wasting your time on middle management who can’t make the final call.
What’s the budget? If the client can’t provide a clear budget, that’s another red flag. Vague answers here often indicate a lack of commitment or clear direction.
By asking these questions upfront, you can quickly determine if a pitch is worth pursuing. If the answers raise concerns, don’t be afraid to walk away.
Actionable Insight:
Create a qualification checklist to vet potential clients before committing to a pitch. If the client doesn’t meet your criteria (e.g., they’re asking for spec work without compensation or the budget isn’t clear), politely decline. This will help you conserve your resources for pitches that have a higher likelihood of success.
Step 3: Take Control by Raising Objections Early
Another way to shift the power dynamic in your favor is by raising objections early in the pitch process. This is a subtle but powerful strategy that forces the client to show their hand. When you raise objections, you’re signaling that you’re not desperate for the work and that you’re willing to walk away if the conditions aren’t right.
For example, when the client gives you a deadline for the pitch presentation, don’t immediately agree to it—even if you have the time. Instead, push back and ask for an extension. “Sorry, that deadline won’t work for us based on our current production schedule. Could we present a day or two later?”
This tactic serves two purposes. First, it allows you to test how flexible the client is and whether they’re truly invested in seeing your pitch. Second, it puts you in the driver’s seat, subtly shifting the power dynamic in your favor.
If the client agrees to the extension, it’s a good sign that you’re a strong contender. If they don’t, it may indicate that you’re just a “third bid,” included for the sake of comparison rather than a serious contender for the project.
Actionable Insight:
Practice raising objections early in the pitch process. This could be as simple as asking for more time, requesting clarification on deliverables, or proposing a different approach. If the client isn’t willing to accommodate your requests, that’s a signal that you may not be a priority for them.
Step 4: Never Stop Pitching
Many creatives make the mistake of treating the pitch presentation as the finish line. They deliver their ideas, cross their fingers, and wait for the client to get back to them. However, this is a passive approach that leaves too much to chance.
Instead, adopt a “never stop pitching” mentality. Even after you’ve delivered your initial pitch, continue to engage with the client. Send follow-up ideas, suggest additional approaches, or offer to clarify any aspects of your presentation. This keeps you top of mind and shows the client that you’re proactive and deeply invested in solving their problem.
For example, after your initial pitch, you might send an email saying, “We’ve been thinking more about your project and came up with an additional idea that we’d love to share with you before you make your final decision.”
This tactic can keep the conversation going and potentially sway the client in your favor—even if they were leaning toward another vendor initially.
Actionable Insight:
Plan for multiple touchpoints with the client throughout the pitch process. Don’t stop engaging after the initial presentation. Follow up with additional ideas, suggestions, or clarifications to keep the conversation alive and demonstrate your commitment.
Step 5: Focus on Relationships, Not Just the Pitch
Winning a pitch isn’t just about having the best creative idea; it’s also about building relationships. Clients want to work with people they trust and feel comfortable with. Therefore, your pitch process should be as much about relationship-building as it is about showcasing your creative work.
Take the time to get to know the client on a personal level. Ask about their challenges, their goals, and what keeps them up at night. Show genuine interest in their success, beyond just the project at hand. By building rapport and trust, you position yourself as more than just a vendor—you become a valuable partner in their business.
Actionable Insight:
Before jumping into your pitch, spend time building rapport with the client. Understand their challenges, goals, and motivations. This will not only make your pitch more relevant but also help you establish a stronger relationship that goes beyond the project at hand.
Step 6: Own Your Intellectual Property
One of the most frustrating aspects of pitching is when a client takes your ideas and gives them to another vendor to execute. Unfortunately, this happens more often than it should, especially when you’re pitching for free.
To protect yourself, it’s important to be clear about who owns the intellectual property (IP) from the outset. If you’re pitching for free, make sure the client understands that you retain ownership of any ideas presented unless they compensate you for them.
Alternatively, if the client is paying for the pitch, be aware that they may claim ownership of the ideas you present. In this case, make sure the compensation reflects the value of the IP you’re handing over.
Actionable Insight:
Always clarify IP ownership before entering a pitch. If you’re pitching for free, retain ownership of your ideas. If the client is paying for the pitch, ensure that the compensation reflects the value of the ideas being presented.
Step 7: Learn When to Walk Away
One of the hardest lessons in pitching is knowing when to walk away. Not every pitch is worth pursuing, and sometimes the best decision you can make is to say no.
If you’ve followed the strategies in this guide—qualifying your clients, raising objections, and gauging their responsiveness—and the red flags are piling up, it’s time to consider walking away. Continuing to invest time and resources in a pitch you’re unlikely to win is a recipe for burnout and frustration.
Remember, walking away from a bad pitch frees you up to pursue better opportunities. It also sends a strong message to the client that you’re serious about your work and won’t compromise on your principles.
Actionable Insight:
Set clear criteria for when to walk away from a pitch. If the client isn’t meeting your standards or if the red flags are adding up, don’t be afraid to cut your losses and move on to better opportunities.
Step 8: Be Strategic About Spec Work
While spec work is a common part of the pitch process, it’s important to be strategic about when and how you engage in it. Spec work can be a significant investment of time and resources, so it’s crucial to ensure that it’s worth your while.
One approach is to limit the amount of spec work you’re willing to do and be clear with the client about what you will and won’t provide. For example, you might agree to present high-level concepts but not full-blown designs or prototypes.
Alternatively, if you’re confident that you’re a strong contender, you might decide to go all-in on the spec work to secure the project. The key is to make these decisions strategically, based on your assessment of the client’s commitment and the likelihood of winning the pitch.
Actionable Insight:
Set boundaries around spec work and communicate them clearly to the client. Be strategic about how much spec work you’re willing to do based on the potential return and your confidence in winning the project.
Step 9: Leverage the “Why Us?” Question
One of the most powerful questions you can ask during a pitch process is, “Why do you think we’re the right fit for this project?” This question forces the client to articulate why they chose to include you in the pitch process, and it gives you valuable insights into their decision-making.
If the client can provide a strong, specific answer—such as, “We were impressed by your previous work with X brand, and we think you’d bring a unique perspective to this project”—that’s a green flag. It indicates that the client sees real value in your expertise and isn’t just shopping around for the lowest bidder.
On the other hand, if the client struggles to answer the question or gives a vague response, that’s a red flag. It may indicate that you’re not a priority for them, and you should reconsider whether the pitch is worth your time.
Actionable Insight:
In your next pitch conversation, ask the client why they think you’re the right fit for the project. Use their response as a barometer for how serious they are about working with you.
Step 10: Build a Scalable Pitch Process
Finally, one of the keys to consistently winning pitches is to build a scalable pitch process. This means developing systems and templates that allow you to respond to pitches efficiently without reinventing the wheel every time.
Create a pitch template that you can customize for different clients, rather than starting from scratch for each new opportunity. Develop a qualification checklist to vet potential clients before committing to a pitch. Build a library of case studies, testimonials, and portfolio pieces that you can quickly pull from when preparing a presentation.
By systematizing your pitch process, you’ll be able to respond to more opportunities with less effort—and increase your chances of winning high-quality clients.
Actionable Insight:
Invest time in building a scalable pitch process that includes templates, checklists, and resources you can reuse. This will save you time and effort while allowing you to focus on the strategic elements of each pitch.
Conclusion: Pitch to Win, Not to Please
Pitching doesn’t have to be a soul-crushing experience. By approaching it strategically, qualifying your clients, and taking control of the process, you can dramatically increase your chances of winning high-quality clients.
Remember, it’s not about pleasing everyone or following every client’s instructions to the letter. It’s about positioning yourself as an expert, building strong relationships, and ensuring that the pitches you invest in are worth your time and effort.
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