How Mistakes Can Improve Your Job Search

Over the last few years, I’ve switched jobs, given many interviews, and spent hundreds of hours optimizing my resume and profile. During this journey, I made plenty of mistakes that cost me time and opportunities. So today, I want to share these genuine mistakes—and more importantly, how you can avoid them: Applying Randomly & Everywhere: In the early stages, I thought applying to as many jobs as possible was the key. Big mistake! Quality always beats quantity. Lesson: Tailor each application to the job role. Research the company and make sure your resume aligns with their requirements. Ignoring LinkedIn & Online Presence: Initially, my LinkedIn profile was incomplete and poorly optimized. I underestimated the power of LinkedIn visibility. Lesson: Your online presence matters. A complete, active LinkedIn profile attracts opportunities you’d never find by traditional methods alone. Sending Generic Cold Messages: I used to send cold messages like "Hi, can you refer me?" which rarely received replies. Lesson: Craft a concise, clear message. Always include the specific role, job link/ID, your resume, and a short summary of your skills. Poor Resume Formatting: My resume had too many graphics, complicated formatting, and lacked the right keywords. This reduced my ATS compatibility. Lesson: Keep your resume simple, structured, and ATS-friendly. Use clear headings, bullet points, and keywords from the job description. Not Preparing for the "Tell Me About Yourself" Question: I used to treat this question lightly and gave long, vague answers. The interviewer would lose interest quickly. Lesson: Prepare a structured 1-minute summary focusing on your experience, skills, and how you match the job you're interviewing for. Underestimating the Job Description: I didn't closely analyze the job description and often missed key details required by employers. Lesson: Job descriptions are gold. Analyze them carefully and reflect their highlighted skills and requirements in your application and interviews. Overlooking Company Research: During interviews, I would have limited knowledge about the company's products or mission. This made my answers generic. Lesson: Always research the company’s recent activities, products, and news. It helps you answer questions meaningfully and shows genuine interest. Getting Demotivated by Rejections: Early rejections made me question my capabilities, negatively impacting future interviews. Lesson: Every rejection is a lesson. Ask for feedback, reflect, and improve. Rejection means redirection—not the end of the road. Negotiation Mistakes: I used to accept offers quickly without proper negotiation due to the fear of losing the offer. Lesson: Negotiate politely but confidently. Companies expect this. Always understand your market worth, and clearly communicate your value. Have you made similar mistakes or learned something valuable from your own job search? Share your experiences in the comments—let's help each other grow!

Your job search spreadsheet shouldn’t just track jobs, It should track mistakes. Most spreadsheets look the same: → Company, role, date applied, status. But the real value? It's in the column that almost nobody has A reflection column. Every rejection, ghosting, or failed interview is data. Not personal. Not shameful. Just valuable data you can learn from. So track it: → What went wrong? → What could’ve been better? → One thing you’ll do differently next time? I started doing this after a streak of rejections. Patterns became clear. Adjustments became obvious. Progress became measurable. And suddenly, each rejection wasn't a loss. It was clarity. Don't just track your attempts. Track your lessons. Because your next job isn’t found in your wins It's found in how you handle and adapt from your misses.

A few weeks ago, I made a post about a mistake I made at work and how I owned it in a public slack channel. I got more DMs about that post than anything I’ve ever shared. Turns out, people respond well when you own up to making a mistake and share your learnings. And accountability is still pretty refreshing. Every time I’ve been honest about a mistake or weakness in an interview, it’s worked out for the right company. So in the spirit of sharing mistakes in public, here are two examples I’ve shared in the interview process as a candidate: 🎯 Attention to detail. At Zapier, I opened a role incorrectly in our ATS that didn’t align with our headcount plan. It caused a mess in our headcount tool and created massive confusion for finance, my manager, and the department lead. It felt like a painful mistake at the time. But I owned it and apologized. After that, I followed our process documentation for every role I opened, and it never happened again. 🎯 Prioritization. When I worked at HubSpot, I was on a 30-person engineering recruiting team interviewing 60 candidates a month. I kept moving candidates to teammates’ roles, trying to fill anything that needed filling. But my own roles were going cold. My manager gave me direct feedback: focus on your own pipeline. Make sure your hiring managers are supported. He was right. I started saying no more often and tightened my focus. When interviewers ask about weaknesses or mistakes, they’re not looking for a weakness that's actually a strength. They’re looking for self-awareness. They want to know: • Can you reflect on your work honestly? • Can you take feedback without spinning it? • Do you learn and adapt? The takeaway I’ve learned as both a recruiter and a candidate: Don’t hide your mistakes. Show what you’ve done since. What's an honest mistake or weakness you've shared in an interview?

Years ago, I flubbed an interview with Stripe's cofounder John Collison. I was fresh off a tough job. The things I was still processing in that conversation killed any chance I had: At the time, Stripe wasn’t even sure they wanted product management. I made it easy for them to pass. Looking back, I wouldn’t have hired that version of me either. After interviewing thousands of people across functions, I often see the same patterns. They make me cringe at the obvious ways I was shooting myself in the foot. 1. Showing up wounded. We're all human and have been through things. Sure you can use that to be real and show you’ve learned. But more often it looks like you’re still processing. Why draft a player who’s still injured over one at full health? 2. Lack of (grounded) confidence. If you don't know you're good, why will someone else? Don’t mistake this for hubris. That loses too. Instead, be clear about what you bring, based on real results. 3. Energy is contagious. People mirror what they see. If you’re curious and excited, you’re more likely to get the same back and they’ll like you more. 4. The biggest mistake: not letting them know you want the job. Candidates think playing hard to get is strategic. Of course you’re evaluating them too. Good people have options. But everyone wants to be chosen. Literally saying "I want this job" increases your odds of getting it. Share what excites you about the role. Be enthusiastic about the parts you love. Nobody wants to work with someone who doesn't want to work with them. You already know all of this. You've probably given the same advice to someone else. But if you’re not landing your dream job, you’re still making these mistakes yourself. Getting out of your own way is harder than it sounds. Trust me, I’ve been there.

10 common job search mistakes – and how to fix them: Job searching can feel like throwing spaghetti at the wall—hoping something sticks. But often, it’s not the job market holding you back—it’s the habits you’ve picked up along the way. Let’s dive into the most common missteps and how to fix them. 1. Applying to Every Job You See Spraying and praying doesn’t work. Hiring managers can sense a generic application a mile away. 🔄 Fix: Be intentional. Focus on roles that align with your skills and goals. Tailor your application to each job. Quality beats quantity. 2. Skipping Networking Relying solely on job boards? Big mistake. 🔄 Fix: Reach out to people in your desired field. Connect on LinkedIn, and ask for informational interviews. 3. Using a Cookie-Cutter LinkedIn Profile Your LinkedIn should be more than a digital resume. If it’s dry or outdated, you’re missing opportunities. 🔄 Fix: Showcase your personality and accomplishments. Post about your expertise, engage with others, and keep your profile optimized with keywords. 4. Not Following Up Submitting an application and waiting in silence? That’s like sending a text and staring at your phone. 🔄 Fix: Send a polite follow-up email after applying or interviewing. Express your interest and remind them why you’re the perfect fit. 5. Relying Too Much on Job Boards Job boards are great, but they’re not the only way to land a job. 🔄 Fix: Diversify your approach. Tap into your network, research companies directly, and leverage recruiters. 6. Not Practicing for Interviews Thinking you can just “wing it” in an interview is a recipe for disaster. 🔄 Fix: Prepare answers to common questions, rehearse your elevator pitch, and research the company. Confidence comes from preparation. 7. Ignoring Company Research Applying without understanding the company’s mission and values? That’s a surefire way to miss the mark. 🔄 Fix: Spend time on their website, LinkedIn, and recent news. Use that knowledge to tailor your application and interview responses. 8. Focusing Too Much on Job Titles Titles can be deceiving. What one company calls “Manager,” another might call “Specialist.” 🔄 Fix: Read the job description carefully. Focus on responsibilities and qualifications rather than the title. 9. Not Asking for Feedback Rejected after an interview and moving on without learning why? You’re missing a growth opportunity. 🔄 Fix: Politely ask for feedback. It can give you valuable insights to improve for your next opportunity. 10. Getting Discouraged Too Quickly Job searching is tough—it’s easy to feel defeated after a few rejections. 🔄 Fix: Remember, it’s a numbers game. Reframe rejection as redirection and keep pushing forward. Your persistence will pay off. The Bottom Line A successful job search is part strategy, part mindset. Evaluate your habits, refine your approach, and don’t forget to lean on your network. What’s been the most challenging part of your job search?

"I've sent out dozens of applications, and it's so frustrating not hearing back from recruiters." The problem might not be your experience. It might be your CV. After reviewing hundreds of CVs, I see the same five mistakes blocking great people from great opportunities. 1. The "Responsible For" Syndrome ❌ Old Way: "Responsible for managing the social media calendar." ✅ Fix: "Grew social media engagement by 45% in 6 months by implementing a new content strategy." 👉🏾 Swap duties for achievements. Use numbers to show your impact. 2. The Wall of Text Recruiters spend seconds on a CV. A dense, paragraph-heavy document is daunting and gets skipped. 👉🏾 Use bullet points, white space, and clear headings. Make your wins easy to find. 3. The Generic Objective Statement "I am a hard-working professional seeking a challenging role that utilizes my skills..." This says nothing and wastes prime real estate. 👉🏾 Replace it with a punchy Professional Summary — 2-3 lines that sell your unique value. 4. Keyword Mismatch If your CV doesn't include the keywords from the job description, the Applicant Tracking System (ATS) might auto-reject it. 👉🏾 Mirror the language used in the job ad for key skills and tools. 5. Typos & Grammatical Errors A single typo signals a lack of attention to detail. It's an easy excuse for a recruiter to move to the next candidate. 👉🏾 Read it aloud or use a text-to-speech tool. Then, have a friend proofread it. Small tweaks make big difference. All the best in your search.