Transitioning from manual to AI-assisted cover letter writing can be challenging. We've gathered insights, tips, and best practices to make the process more efficient and effective.
Cover Letter Structure
Employ personalized greetings: Start with a standard greeting to add a personal touch and to make the recipient feel acknowledged.
✅ [[Start with a personal greeting using the client's first name or the company name.]]
Keep it simple: The AI responds best to succinct, clear instructions. Overly complicated or too detailed instructions can confuse the AI, leading to suboptimal results.
✅ [[Make a whole proposal with less than X symbols. Use short sentences. Do not include any information associated with Y.]]
Specify your expectations: Be specific about what you want to achieve with the cover letter. This could include analyzing the job requirements, selecting relevant projects from your portfolio, and highlighting your experience in a particular field.
If you want the AI to use a specific project from your portfolio, provide detailed guidelines. For instance, define what makes a project relevant or outline the specific criteria or triggers the AI should consider. Leaving it up to the AI to "choose the most relevant project" without any parameters can lead to less effective results.✅ [[If the job description mentions keyword 1, keyword 2, keyword 3 or it was built on either one of Frontend: React; Backend: NestJS; describe how I helped Company 1 and Company 2.]]
Highlight Success Stories: Include these details if a project led to a company receiving investment or achieving a higher customer retention rate. These success stories serve as excellent selling points.
✅ [[If the job description mentions technology 1 or technology 2, mention how I helped Client X and Client Z to improve 5x platform performance and brought on 29% faster time-to-market.]]
Ask Relevant Questions: While questions can be engaging, they must be purposeful and related to the job. For example, inquiring about the project's goals or the desired outcomes can help tailor the cover letter more effectively.
✅ [[Briefly analyze the project details and pose a question that could strengthen our bid.]]
Call to Action: Use a call to action at the end of your Cover Letter. The last paragraphs tend to work better for client conversion.
✅ [[End with a straightforward call to action, asking for details about the client’s desired outcomes and extra details for the project in one sentence.]]
General Guidelines
You Better Do!
Use Relevant Keywords: Including relevant keywords in your prompts can help the AI generate more targeted and applicable cover letters.
Provide detailed instructions: For the AI to generate relevant content, provide detailed instructions about your needs and the expected outcomes. If you don’t have any quantitative data, consider referencing logos, significant projects, industry, tech stack, and the results of completed projects.
Configure Temperature: The instructions' style and 'temperature' can impact the AI's performance. A higher 'temperature' allows the AI to deviate from the instructions more, providing a broader scope for creativity and informal language. A lower 'temperature' will result in more precise instruction adherence and a more formal writing style.
Use broad terminology: AI doesn’t recognize synonyms. Instead of just mentioning HR, be specific by using detailed terms like recruiting, HR, sourcing talents, data management, etc.
Keep it relevant: Always tie your cover letter to the job description. Highlight specific points, such as how you plan to solve a client's problem or meet their goals.
Focus on the freelancer, not the agency: When writing prompts for cover letters, ensure that the instructions are specific to the freelancer profile and not the agency. This is important because the cover letter bids are usually submitted using different freelancers’ profiles. The context should be strictly about the freelancer, not the agency.
You Better Don’t 😶
Use generic greetings: While it might seem polite to address your potential employer with a generic "Good morning" or "Good afternoon", try to personalize your greeting. Use the client's name or the company's name to create a more personal connection.
✅ [[Start with a personal greeting using the client’s first name or the company name (omit "LTD", "LLC", "Limited", "International" "Corporation" or "Corp" from the company name).]]
Give too detailed instructions: Overcomplicated prompts can confuse the AI and result in less effective cover letters. Keep things simple and clear, use short, simple sentences, providing only the necessary information. E.g.:
✅ [[Create a proposal highlighting my experience in React and NestJS.]]
🚫 [[Please create a comprehensive proposal covering all aspects of my career, including every job and project I've worked on.]]
Focus on irrelevant details: Ensure that the AI focuses on the crucial aspects of the job description and the candidate's suitability for the role. Don't focus too much on aspects that don't directly contribute to showcasing your skills or achievements.
✅ [[If the job description mentions AI-driven solutions or machine learning - mention that I’ve recently completed a project for a fintech startup that implemented AI algorithms for fraud detection and achieved a 40% reduction in fraudulent transactions.]]
Be too informative: Writing in a more engaging and question-oriented style is better than overly informative. Proven to be more effective in stimulating the clients' interest.
✅ [[Mention my extensive experience with over 223 projects, including work for well-known brands like X1, X2, X3.]]
🚫 [[I have completed numerous projects in SaaS development]]
Rely on generic phrases: Phrases like [[ask the engaging question related to the project]] or [[I have experience in SaaS development projects]] can be too vague. Instead, focus on asking specific, targeted questions about the project's goals or desired outcomes.
✅ [[If the job description mentions cloud infrastructure or AWS, mention how I optimized cloud infrastructure for a leading e-commerce company, resulting in a 30% cost reduction and 50% performance improvement.]]
✅ [[If the job description highlights data analysis or Python, share how I developed a data analysis tool in Python that helped a retail client increase sales by 20% through better customer insights.]]
🚫 [[Mention one pain point from the job posting and explain how solve it, while keeping it engaging and relatable.
Don’t limit repetitive information in your portfolio description: If all the projects are based on the same technology, there's no need to repeat this information for each project. Instead, focus on what makes each project unique.
✅ [[In Project A that involved machine learning and AI, I managed a cross-functional team to deliver a complex software project 2 months ahead of schedule, resulting in a 15% increase in client satisfaction.]]
✅ [[In Project B that involved machine learning and AI, I implemented machine learning algorithms for a healthcare startup, improving diagnostic accuracy by 25% and securing a $2M investment.]]
Over-Americanize: People often believe that if a text sounds too Americanized, it must be either from a non-native speaker or someone who has recently moved from the U.S. This can impact conversion rates, as it sets different expectations from the freelancer. Therefore, avoid phrases that sound too Americanized.
✅ [[Avoid phrases like "no problem," "sure thing," or "got it." Instead, use more neutral terms like "certainly," "absolutely," or "understood."]]
Use "we" in the instructions: The use of "we" prompts the AI to write from an agency's perspective instead of a freelancer's perspective. This could decrease the effectiveness of the bids and lower the chances of proposal acceptance.
✅ [[I have extensive experience in React and NestJS, having completed numerous projects that required front-end and back-end development.]]
🚫 [[We recently completed a machine learning project for a healthcare startup that improved diagnostic accuracy by 25%.]]
Overuse formal or fancy English: While it might seem like a good idea, this can actually decrease the conversion rate. The text should engage the reader in a conversation rather than overwhelm them with descriptive words or formalities. Use a conversational style. This is especially relevant if your company is primarily based in a non-English-speaking country.
✅ [[Use conversational language like “I'm excited to apply for the position of...”]]
🚫 [[Write in formal language like “It is with great pleasure that I submit my application for the esteemed position of...”]]
Use too many adjectives: Based on experience, using too many adjectives doesn't lead to the desired conversion. Keeping the language simple in cold outreach is important. While they can add flavor to a piece, too many adjectives make the text seem less serious or businesslike.
✅ [[Avoid phrases like “I possess an extraordinary ability to lead, an unparalleled attention to detail, and an exceptional work ethic.” Instead, use “I have a strong ability to lead, attention to detail, and a solid work ethic.“]]
Give unnecessary restrictions: Restricting the AI, for example, by specifying a list of words not to be used in the cover letter, can limit its effectiveness. Especially if you set the 'temperature' to zero, the AI will strictly adhere to the instructions and may not use any of the words you've listed, even if they could enhance the letter.
✅ [[Use clear and straightforward language to describe my skills and achievements.“]]
🚫 [[Don’t use the following words: realm, holistic, tailored, tailor, tailoring, robust, stay tuned, seamless, cornerstone, testament, paramount, diving into, delve into, pivotal.]]
Use of local language: Stick to English for the best results; local language does not necessarily add value to your cover letter. It might confuse your potential employer or give the impression that you're uncomfortable with English.
🚫 [[Include an expression of enthusiasm using the client's name in the local language of their country.]]
Keep using links to external sources: Including links to sources other than your Upwork portfolio and GitHub is not recommended due to certain Upwork guidelines that might flag your proposal. Avoid including links to external sources, and instead, structure your Upwork portfolio based on projects and successful cases.
✅ [[If the project mentions e-commerce, beauty or online shop, then say we improved X client’s lead to user conversion by 23% and attach this link to it]]
ℹ️ Note: You can still use links to platforms like Dribbble or Behance when filling out the Clients Questions section.
Crafting the perfect cover letter prompt might take a bit of practice. AI can help create more compelling and engaging cover letters by focusing on the most relevant experiences and tailoring the letter to the specific requirements of the job description.