In the world of marketing, the path to mastery begins with studying the masters. Just as artists study the great painters and musicians learn from the maestros, marketers can gain invaluable insights by examining the strategies of industry leaders. These trailblazers have honed their craft over years of practice, experimentation, and success, providing a treasure trove of lessons for anyone eager to improve their marketing skills.

One such master is Ann Handley, a luminary in the fields of marketing and content creation. Known for her engaging voice and practical wisdom, Handley has earned a reputation as one of the most respected figures in modern marketing. She is the author of two Wall Street Journal bestsellers: Everybody Writes: Your Go-To Guide to Creating Ridiculously Good Content and Content Rules (co-authored with C.C. Chapman).

Ann is also the Chief Content Officer at MarketingProfs, a leading online resource for marketers, where she provides guidance to businesses worldwide. Her expertise has been recognised globally, earning her a place on Forbes’ list of “Top Influencers in Social Media” and LinkedIn’s list of “Top Voices in Marketing.” With decades of experience in storytelling, strategy, and content creation, Ann Handley’s insights empower us to write better, connect more deeply with our audiences, and create content that truly resonates.

By delving into her work and advice, we can uncover actionable strategies to use in our marketing efforts and sharpen our writing skills, one word at a time. I’m sure there are hundreds of tips that Ann Handley has bestowed upon us over the years, but here are my top ten.

This is quite a long article, so if you want a TL;DR, click here.

1. Start with a goal

Ann highlights the importance of writing with a clear purpose. Every piece of content should align with a broader objective, such as increasing brand awareness, driving engagement, or converting leads into customers.

Key insight

Content without a goal is like a ship without a rudder, it may be well-crafted but lacks direction. Knowing your goal helps you tailor your tone, structure, and messaging to achieve a tangible outcome. It also keeps your writing concise and on-track, avoiding unnecessary detours that might confuse or bore your audience.

How to apply

• Before you begin, ask yourself, what action do I want my audience to take after reading this? Is it subscribing, sharing, purchasing, or simply gaining knowledge?
• Write your goal at the top of your outline and use it to shape your content. For example, if your goal is to increase newsletter sign-ups, make sure your CTA (call-to-action) is clear and repeated at key points.
• Measure success by aligning your goal with metrics. For instance, track click-through rates or engagement for social media posts.

2. Put the reader first by asking “So What?”

Ann insists that great writing centres on the reader’s needs, not the writer’s agenda. By asking “so what?” repeatedly, you ensure that every point provides value or solves a problem for the audience.

Key insight

Many writers fall into the trap of assuming their audience will care about their content just because they wrote it. Asking “so what?” forces you to dig deeper into the real value behind your message. It sharpens your focus on how your writing benefits your readers.

How to apply

• After drafting a section, interrogate its relevance by asking, “Why should my reader care about this?” If you can’t answer, revise it.
• Replace feature-driven statements with benefit-driven ones. For example, instead of saying, “We have 24/7 customer support,” say, “You’ll always have peace of mind knowing help is available anytime you need it.”
• Create an empathy map for your audience to clarify their challenges and tailor your writing to address them.

3. Embrace the “Ugly First Draft”

Ann encourages writers to prioritise getting ideas onto the page, no matter how messy. Perfectionism can kill creativity, but the editing process can transform a rough draft into polished brilliance.

Key insight

First drafts are never final drafts. By allowing yourself to write freely, you bypass the inner critic and unlock new ideas. The true craft of writing happens during the revision phase, not the initial one.

How to apply

• Set a timer for 15–30 minutes and write without pausing or self-editing. Treat it as a brain-dump.
• Use placeholders for missing ideas (e.g., “[Insert statistic here]”) to maintain momentum.
• Give yourself permission to write badly—it’s part of the process. The aim is progress, not perfection.

4. Organise your writing with clear structure

Ann believes structure is essential for guiding readers through your content in a logical and engaging way. Without structure, even the most insightful writing can feel chaotic.

Key insight

A clear structure allows readers to quickly understand your message and follow your argument. It also makes your writing more visually appealing, especially for online content where attention spans are short.

How to apply

• Choose a format that best suits your content, such as a list, how-to guide, or case study.
• Use an outline to map out your main points before you start writing.
• Break your text into smaller sections with subheadings and bullet points to make it easier to scan. Aim for one key idea per paragraph.

5. Add your voice to your writing

Ann advises writers to inject personality and authenticity into their content. A unique voice builds trust and engagement, making your writing more relatable.

Key insight

In a sea of generic content, your voice is your differentiator. People connect with content that feels human, and your tone and style can make even technical subjects engaging.

How to apply

• Identify your brand’s tone of voice. Are you playful, professional, empathetic, or witty? Be consistent across all platforms.
• Avoid overly formal or stiff language. Write conversationally, as if speaking directly to a reader.
• Use anecdotes, humour, or personal insights to make your writing more approachable and memorable.

6. Be specific, not vague

Ann argues that specific details are what make writing impactful. Vague statements feel hollow and uninspiring, while concrete examples and precise language create trust and resonance.

Key insight

Specificity not only makes your writing more engaging but also more credible. It helps your audience visualise your message and builds a stronger emotional connection.

How to apply

• Replace generic phrases with precise ones. For instance, instead of saying, “Our product helps businesses grow,” say, “Our tool helped 200 SMEs increase revenue by an average of 30% in six months.”
• Use examples, data, and testimonials to add weight to your claims.
• Paint a picture with sensory details when describing experiences or scenarios.

7. Write quickly without overthinking

Ann encourages writers to draft quickly, bypassing the paralysis of overthinking. This approach helps overcome writer’s block and fosters creativity.

Key insight

Speed-writing forces you to focus on the big picture rather than obsessing over small details too early. It’s easier to edit a rough draft than to face a blank page.

How to apply

• Set a timer and aim to finish a rough draft in one session, even if it’s imperfect.
• Avoid editing as you go—reserve polishing for later.
• Use tools like speech-to-text to capture ideas rapidly if typing feels slow.

8. Make implicit ideas explicit

Ann warns against assuming your readers will connect the dots themselves. Clarity is key, and it’s better to over-explain than risk being misunderstood.

Key insight

Readers appreciate when content is direct and unambiguous. Explicit communication ensures your audience fully grasps your message and avoids confusion.

How to apply

• Spell out acronyms, technical terms, or industry jargon if your audience may not know them.
• Use examples and analogies to clarify complex ideas.
• Ask someone unfamiliar with the topic to read your work and highlight anything unclear.

9. Read your writing aloud

Ann champions this technique as a way to catch awkward phrasing, poor rhythm, or overly complicated sentences.

Key insight

Reading aloud forces you to experience your writing as your audience would. It helps you identify problems that might otherwise go unnoticed.

How to apply

• After drafting, read every sentence aloud slowly. Pay attention to flow and tone.
• Mark any sections that feel clunky, confusing, or overly formal, then rewrite them.
• Use this method to test email subject lines or headlines for impact and brevity.

10. Pay attention to readability

Ann emphasises the importance of making content scannable and easy to digest, especially in digital formats where readers skim rather than read in-depth.

Key insight

Dense, jargon-heavy writing turns readers away. Simplicity, brevity, and visual breaks make your content more inviting and effective.

How to apply

• Break up large blocks of text with headings, line breaks, and bullet points.
• Use short sentences and paragraphs (no more than three sentences each).
• Test readability with online tools like Hemingway or Grammarly, and aim for a score that matches your audience’s reading level.

Let’s learn from Ann!

Ann Handley is a trailblazer in content marketing, known for her ability to turn writing into a powerful business tool. Her philosophy revolves around prioritising the reader, crafting authentic and engaging stories, and embracing the art (and science) of clear, purposeful communication.

Which of Ann’s tips speaks to you the most? Share your thoughts in the comments below!

Stay tuned for more insights in our Marketing Masters series, where we dive into the wisdom of the industry’s most visionary thinkers.

Other sources

Follow Ann Handley on YouTube, X (@annhandley) and LinkedIn.

Content Marketing and Blogging with Ann Handleyy – Brand on Brands

10 Unmissable lessons from Ann Handley’s new “Everybody Writes” book – Mark Schaefer

Mastering the Art of the Cold Open in Storytelling – Ann Handley

How to Write Sales Copy that Doesn’t Sound Like You’re Pitching on QVC – Ann Handley

The One Email Metric You Need to Track – Ann Handley

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