If you’ve ever outsourced a task to a freelancer and ended up disappointed with the result, you’re not alone. The problem often isn’t the freelancer’s skill level—it’s the lack of clarity in what you asked them to do.
In his book Who Not How, Dan Sullivan introduced a powerful idea: stop asking “How do I do this?” and start asking “Who can do this for me?” That shift in thinking can be transformative. But there’s a missing piece, Dan only briefly touched on: how to clearly define what you want your “Who” to accomplish.
Dan created a tool called the Impact Filter™ (a trademark of his Strategic Coach® system) to solve this problem. It’s a fantastic concept. However, I found that many of my clients struggled to apply it effectively—the instructions were too succinct, and the name wasn’t intuitive for freelancers or practical for use in project-based environments.
So, I built on Dan’s idea and created something more actionable: the Project Clarity Brief. It’s a plain English version of the Impact Filter™ designed specifically for entrepreneurs and small business owners who regularly work with freelancers on platforms like Upwork, Freelancer, or Toptal. If you’d like to use the same template I use with my own contractors, you can download it here and follow along as you read.
For a more complete list of Freelancer platforms, click here.
Why You Need a Project Clarity Brief
Hiring a freelancer isn’t the same as onboarding a full-time employee. You have limited time to communicate your vision, and the freelancer often has limited time to ask follow-up questions. This challenge is amplified when your freelancers are working in time zones far removed from yours, which can lead to delays and misunderstandings if instructions aren’t crystal clear.
Misalignment is common, and it’s expensive. That’s why the Project Clarity Brief is so essential: your goal is to provide the framework for the “what” and the “why” while allowing the freelancer the autonomy and ownership of the “how.” This approach not only leverages their expertise but also empowers them to bring their best thinking and creativity to the solution. When freelancers feel trusted to deliver outcomes rather than follow step-by-step instructions, they’re more motivated to build something exceptional.
The Project Clarity Brief eliminates confusion before it begins. It forces you to slow down, think clearly, and define:
- What do you actually want done
- Why it matters
- What success looks like
- What failure looks like
- What criteria must be met for the project to be considered complete
When your freelancer has this information upfront, they can:
- Work more independently
- Deliver faster
- Hit the mark on the first try
Most importantly, they can own the “how” while you stay focused on the big picture.
Why This Matters More Than Ever
Freelancers today often work across time zones, cultures, and communication styles. Even the best freelancers can’t read your mind. The clearer your brief, the higher the quality of the outcome.
Many of my clients come to me feeling overwhelmed. They’re working 60+ hours a week, wearing every hat in their business, and falling behind. They need help but they don’t have time to train someone from scratch.
By using a Project Clarity Brief, they can:
- Reclaim dozens of hours per month
- Handoff technical tasks with confidence
- Focus on adaptive work (like strategy, leadership, and decision-making)
Anatomy of the Project Clarity Brief
Here are the core components of the Project Clarity Brief, along with robust guidance for completing each section. To make it practical, I’ll use my own AI chatbot project as an example to provide context for each section. If you want to follow along or use this with your next freelancer, download the Project Clarity Brief template here.
1. Project Purpose
What do you want to accomplish, and why does it matter?
Explain the intention behind the project. What problem are you solving, or what opportunity are you acting on? This helps your freelancer understand the “why” behind the task, not just the “what.”
Example: I want to create an AI chatbot using my blog content to help entrepreneurs get instant business advice, even when I’m not available. The idea is to make my knowledge base searchable and conversational, offering ongoing guidance, with my voice and style. This supports my goal of scaling mentorship without increasing my hours and also helps prospective sponsors see the value in AI-enhanced tools for small business support.
2. Why Now?
Why is this important at this moment? What happens if it’s delayed?
Describe any urgency, timing considerations, or strategic opportunities. This helps your freelancer prioritize your project.
Example: Community banks have not traditionally offered small business advisory services, but to compete with the Big Five institutional banks and fast-moving fintechs, there’s a growing need to start. Especially as SCORE and other federally funded mentoring programs become less available, my AI chatbot—built from years of blog content and designed to deliver personalized small business guidance—could be a turnkey solution they can sponsor. It provides 24/7 access to actionable insights for entrepreneurs, making it a scalable and cost-effective complement to human mentorship. It also serves as a clear differentiator, showcasing how AI support systems are beginning to replace static search or FAQ-based help models. Being ahead of this curve positions me—and my partners—as forward-thinking leaders embracing the future of small business support.
3. Ideal Outcome
What does success look like to you?
Be as clear and vivid as possible. Describe both the functionality and the experience you want the end user to have.
Example: The chatbot should give accurate, relevant answers in a conversational tone that mirrors my blog’s voice. It should recognize typos, business lingo, and related terms. Users should feel like they’re speaking with a helpful business advisor, not a robotic search engine. It should surface relevant insights, even when the user’s question is slightly vague or uses terminology unique to entrepreneurs.
4. Best-Case Scenario
What’s the best thing that could happen if this project goes really well?
Describe how this project supports your broader goals or business strategy. Share how exceeding expectations could open doors to new markets, partnerships, or innovations. This context helps your freelancer understand the bigger picture and motivates them to go beyond the basic deliverable.
Example: The chatbot becomes a featured tool on bank websites, attracting more traffic and building credibility for my brand. It serves as a visible demonstration of how community banks, through a strategic partnership with our team, can modernize their small business support offerings through AI. This positions them to compete more effectively with both traditional institutions and digital-first fintechs. The tool not only provides real value to small business customers but also acts as a tangible differentiator in a crowded marketplace. This exposure could lead to more sponsorship opportunities, reinforce long-term bank-client relationships, and position our partnership as a forward-thinking model for AI-enabled community banking.
5. Worst-Case Scenario
What are the key failure modes you want to avoid?
Calling out risks helps your freelancer steer clear of major pitfalls. It also signals what really matters to you.
Example: The chatbot gives irrelevant, inaccurate, or confusing answers, which erodes user trust and makes the tool feel unreliable. This not only undermines my professional credibility but also weakens the perceived value of the AI support system—especially in the eyes of potential partners like community banks who are evaluating the strength of our offering. If users walk away frustrated or misinformed, we miss the opportunity to demonstrate how our partnership can provide innovative, trustworthy small business guidance at scale. Worse, it can damage relationships with stakeholders who expect seamless experiences. If broken or outdated links show up in the chatbot’s responses, for instance, it can make the system feel unfinished and unprofessional, further diminishing its perceived value.
6. Success Criteria (Checklist)
What criteria must be met for this project to be considered a success?
This is your acceptance checklist. Use clear, objective criteria that leave no room for interpretation. Describe what deliverables need to be completed, how they should perform, and any qualitative standards that must be met to ensure success. This helps the freelancer know exactly what “done” looks like and gives you a confident basis for final approval.
Example:
- Live chatbot integrated into the site
- Pulls answers from my Pinecone vector database
- Handles synonyms and typos
- Matches my tone and mentoring style
- Launch-ready within 2 weeks
Final Thought
As an entrepreneur, your job isn’t to do everything yourself. Your job is to define what needs doing and find the best person to do it. That’s the essence of Who Not How. But to make that strategy work, your freelancer needs a map.
The ProjectClarity Brief is that map.
It’s not a formality. It’s a shortcut to clarity, consistency, and momentum.
What project could you move forward with right now if you just took 15 minutes to define it clearly?