Learning From Mistakes

Life Hack #7 | Learning from strategic mistakes By 1995, my first startup Comnet was ready to take off. That is when I made four big mistakes. My first big mistake was around people. Desperate to start, I invited people I had worked with before, realizing a little that familiarity with people is not the same as creating a high-impact team. It took me months and years of painful learning that hunger, desire, and competence should far outweigh the comfort of knowing people. My second big mistake was around markets. While my people strategy was clear, I was still unclear about the markets. The Internet had just come in and was changing everything around us, and the opportunity size looked big. Thus I was like a child in a candy store wanting to do it all. Soon we ran out of resources and had made little progress. Once again, I learnt the hard way to sharply focus on a micro-segment of the market and become most significant in that segment before looking outwards. That led to the birth of VSATs and the NSE order, and only then did we set our eyes on global opportunities. My third and most embarrassing mistake was around money. Every start-up is bootstrapped, and so were we. However, I was high on possibilities and invested in winning instead of investing to show we CAN win. There is a big difference between these two statements. I realised this difference too late, shifted gears, onboarded a big global bank as an equity partner and then took off. However, this mistake caused a delay of 2 years and a near certainty of a shutdown. My fourth big mistake was around innovation. Innovation comes with an end date, and you have to find a new one. High on the success of VSAT, we almost forgot that we need another ten times bigger idea, and we need to find it before VSAT growth tapers off. We stretched it out, believing that we had a few more years. The Remote Infrastructure Management idea was a big idea that changed Comnet forever; however, I had always wondered if we could or should have launched it a year or two before we did. Life always allows you to make mistakes and correct them before it’s too late. It would help if you had an attitude of humility, openness and a third eye that warns you when you start hearing what you want and not the truth. Have you learnt from your mistakes? Is it right to be open about these mistakes and resultant learnings? What was your biggest mistake-based learning? #stayinspired #startup #innovation #opportunity #learning #strategy

The strongest leaders I know have one thing in common… They’re not afraid to say these three words: “I screwed up.” One of my bosses once stopped a high-stakes meeting cold with those exact words. No excuses. No deflection. Just: “I screwed up. Here’s what happened. Here’s how we’ll fix it.” In that moment, he didn’t lose the room. He earned its respect. We started bringing forward problems earlier. Solving them faster. Owning our work more fully. Because vulnerability…real, humble accountability… is a leadership multiplier. Here’s what it does: → It breaks down walls between “leadership” and “the team” → It gives others permission to own their mistakes, too → It shifts people from fear-based compliance to trust-based commitment The irony? Leaders who try to look bulletproof often come off as insecure. Want to lead like that? No! Try this instead: 1. Admit when you mess up. Accountability builds trust faster than perfection ever could. 2. Share what you’re learning… not just what you’ve mastered. 3. Ask real questions like: “What am I missing?” or “How could I have handled that better?” 4. Normalize “smart mistakes.” Teams that can discuss failure without fear are the ones that grow. The best teams I’ve worked with weren’t led by perfect people… They were led by real ones… honest ones. Psychological safety isn’t soft. It’s how high-performing teams are built. What would shift if you led with that kind of strength today? ⸻ Follow me (Jon Macaskill) for leadership insights, wellness tools, and real stories about humans being good humans. And yeah… feel free to repost if someone in your life needs to hear this. 📩 Subscribe to my newsletter here → https://lnkd.in/g9ZFxDJG You’ll get FREE access to my 21-Day Mindfulness & Meditation Course—packed with actionable tools to lead with clarity and resilience.

Show vulnerability. Build trust. Navigating the fear of mistakes is tough. 1. Sharing own mistakes openly ↳ Shows errors are opportunities for growth ↳ Creates an authentic space for others 2. Shifting focus from blaming to understanding ↳ Learns from what went wrong ↳ Builds a culture of continuous improvement 3. Normalizing continuous learning ↳ Promotes resilience ↳ Encourages a growth mindset When the CEO I worked with embraced these actions, her leadership style transformed. Her team became more resilient and open to learning. Why? Because showing vulnerability is powerful. It creates a safe space for everyone to express their challenges. And in a high-pressure environment, that’s invaluable. Remember: Mistakes aren't failures. They’re steps to success. It’s about learning, growing, and moving forward. --- Considering working with a coach? https://lnkd.in/dC4tYDSS

Leadership is Tested in Moments of Anger It was a busy Monday morning when Sarah, a team lead, received an urgent email from her manager, Mark. "The presentation slides are a mess," Mark wrote. "Fix them immediately!" Sarah had spent the weekend perfecting the slides, ensuring every detail was aligned with the brief. Confused and frustrated by the criticism, she responded, "Mark, could you specify what needs fixing? I’ve followed all the guidelines provided." Mark, still fuming after a stressful client call, didn’t bother to explain. His frustration spilled over, and he fired off more curt responses, blaming Sarah for what he thought was a poorly prepared presentation. Hours later, after calming down, Mark finally reviewed the slides again. To his surprise, they were flawless. The issue wasn’t Sarah’s work—it was his own stress clouding his judgment. Realizing his mistake, Mark walked over to Sarah’s desk. "I owe you an apology," he admitted. "Your work was excellent. My frustration earlier was misplaced." Sarah accepted the apology, but the incident left her thinking: Could this have been avoided? Mark learned an important leadership lesson that day: Anger is short-lived, but its impact can last far longer. Here’s what leaders can take away from this: 1/ Pause Before Reacting: When emotions run high, step away. A moment of calm can prevent a lifetime of regret. 2/ Seek Understanding Instead of Blaming: Before pointing fingers, ask questions. Often, frustrations stem from misunderstandings, not mistakes. 3/ Apologize and Correct: Mistakes happen—even for leaders. Owning up to them strengthens trust and respect within the team. 4/ Lead with Clarity: Leadership isn’t about being right all the time; it’s about navigating challenges with composure and fairness. In leadership, the true test isn’t avoiding mistakes—it’s about how you handle them when they arise. Anger might feel justified in the moment, but clarity and understanding always leave a stronger impact. What’s one moment where a pause or a second thought helped you avoid a mistake? How did it shape you as a leader?

AI models like ChatGPT and Claude are powerful, but they aren’t perfect. They can sometimes produce inaccurate, biased, or misleading answers due to issues related to data quality, training methods, prompt handling, context management, and system deployment. These problems arise from the complex interaction between model design, user input, and infrastructure. Here are the main factors that explain why incorrect outputs occur: 1. Model Training Limitations AI relies on the data it is trained on. Gaps, outdated information, or insufficient coverage of niche topics lead to shallow reasoning, overfitting to common patterns, and poor handling of rare scenarios. 2. Bias & Hallucination Issues Models can reflect social biases or create “hallucinations,” which are confident but false details. This leads to made-up facts, skewed statistics, or misleading narratives. 3. External Integration & Tooling Issues When AI connects to APIs, tools, or data pipelines, miscommunication, outdated integrations, or parsing errors can result in incorrect outputs or failed workflows. 4. Prompt Engineering Mistakes Ambiguous, vague, or overloaded prompts confuse the model. Without clear, refined instructions, outputs may drift off-task or omit key details. 5. Context Window Constraints AI has a limited memory span. Long inputs can cause it to forget earlier details, compress context poorly, or misinterpret references, resulting in incomplete responses. 6. Lack of Domain Adaptation General-purpose models struggle in specialized fields. Without fine-tuning, they provide generic insights, misuse terminology, or overlook expert-level knowledge. 7. Infrastructure & Deployment Challenges Performance relies on reliable infrastructure. Problems with GPU allocation, latency, scaling, or compliance can lower accuracy and system stability. Wrong outputs don’t mean AI is "broken." They show the challenge of balancing data quality, engineering, context management, and infrastructure. Tackling these issues makes AI systems stronger, more dependable, and ready for businesses. #LLM

Repair. It's a skill every leader needs. But it's hardly ever talked about. I wish someone had told me in my first leadership gig that I'd need to learn the art of repair. Turns out, my biggest mistake wasn't double paying 16ish people in one pay cycle [yep was a bad time, and 'ish' doesn't go down well in payroll]. My most painful mistakes have been when I’d damaged a relationship. The times when I needed to say sorry for losing my cool. Or, I needed to rebuild trust after letting someone down. Or I needed to take personal accountability for behaviour that didn’t help the team. As much as leadership failures are painful, they're also inevitable. It's the cost of the role. Welcome to leadership, you're going to fail in really painful and public ways (feel free to write this leadership affirmation down). No one gets it right all the time. And we shouldn't expect to. What we should expect is that we'll need to learn the art of repair. Instead of trying to 'be right’ all the time, we need to know how to repair things when they're not right. A few simple things that help: 1)Seeking to understand different perspectives. Actively listen. Ask curious questions. Sit with the mess of the situation for a bit. Don’t try to gloss over it. 2) Take personal ownership. No 'apologies' emails. Fully own it. Pick up the phone, or meet IN PERSON and say 'I'm really sorry. I stuffed that up, it's not ok.' Be vulnerable. No one expects you to be perfect. But they do expect you to take ownership. 3) Take action. Get clear on what needs to change. And then commit to it. Don't just talk about what you're going to do, do the thing. #leadership #management #HR #peopleandculture

I used to think I always had to look confident as a leader. Even when I wasn’t. Showing any kind of vulnerability felt like losing control. I thought that if I admitted mistakes or asked for help, my team wouldn’t respect me anymore. But here’s the thing: admitting mistakes or asking for help doesn’t make you weak. It makes you stronger. ▶️ It builds trust and respect ▶️ helps you learn faster ▶️ shows your team it’s okay to be human. When I started doing this, my team: ▶️ trusted me more ▶️ stepped up to support me ▶️ we solved problems faster, together. This is just one of 5 people skills to develop as a techie if you want to level up your career. 🔗 Discover the other 4 skills and more strategies in this article I co-wrote with Caleb Mellas: https://lnkd.in/dWcWtkHQ

"Why 'Done' Beats 'Perfect' Every Time in Startups 🚀" In startups resources are scarce, adopting the mindset of "done is better than perfect" can be transformative. ✂️ This isn’t about cutting corners; it’s about building momentum, learning fast, and iterating smarter. Every moment spent crafting the "perfect" plan is time lost that could have been spent learning directly from users and clients. Waiting until you have 95% of the data before making a decision often results in missed opportunities. A product or feature in the hands of users—no matter how raw—provides insights that endless polishing never will. Execution, even if imperfect, builds trust with stakeholders and ensures consistent progress. 🐎 Your ultimate goal is to "Optimise for Speed of Learning, not being "right." every time. Still, many founders and operators struggle to adopt this mindset. Here are three common blockers—and practical ways to overcome them: 1️⃣ Fear of Judgment ↳The Problem: Worrying about how others will perceive your imperfect work. ↳The Solution: Shift your team’s focus to learning. Use a framework like "Learning First": commit to shipping a minimum viable version to gather user insights, no matter how rough. Frame every launch or decision as an experiment. Hold weekly reviews to discuss "What did we learn this week?" This creates a culture that values trying new things over obsessing about perfection. 2️⃣ Overengineering Mindset ↳The Problem: Teams prioritise extra features or backend perfection instead of delivering value quickly. ↳The Solution: Use strict deadlines to force progress. Allocate a fixed period for development and commit to releasing the product or feature at the end—regardless of its state. Emphasise the experimental nature of the work and acknowledge the potential for failure. This builds confidence in focusing on what truly matters rather than perfection. 3️⃣ Lack of Clear Goals ↳The Problem: Without clear priorities, perfectionism creeps in. ↳The Solution: Define a single clear goal for each team or department. Encourage everyone to consistently ask, "Does this task align with our objectives?" If it doesn’t, deprioritise it. This ensures focus and eliminates unnecessary tinkering. 💡 Over the years, I’ve frequently asked my teams: “Is this a Done vs. Perfect dilemma?” It became such a mantra that they started asking it themselves—and even back to me. That’s when I knew the mindset had truly taken hold. ❓ What about you? How do you balance done vs. perfect in your work? ___________________________________________________ 👉 After 25 years in startups and VC, I now dedicate my time to helping startup founders thrive! 📌 Share this post and follow me for practical startup-building tips that work.

Progress isn't always linear. I recently read an article by Eugenie Rives, a former Moonshot Catalyst at Alphabet’s X, the moonshot factory, and it struck a chord with me. She shared the story of shutting down her robotics project, “Move,” and the immense difficulty of telling her team the news. But what stood out was her perspective on what came next. Rives described something she called 𝗠𝗼𝗼𝗻𝘀𝗵𝗼𝘁 𝗖𝗼𝗺𝗽𝗼𝘀𝘁—the idea that even failed projects nourish future breakthroughs. The tools, prototypes, and lessons from “Move” didn’t disappear; they became the foundation for new innovations. It made me reflect on how often we hold onto projects or ideas simply because of the time and energy we’ve invested. But sometimes, the greatest value we can create is letting go and repurposing what we’ve learned for something bigger. Here’s what I’m taking away from this: 1️⃣ 𝗙𝗮𝗶𝗹𝘂𝗿𝗲 𝗶𝘀𝗻’𝘁 𝘄𝗮𝘀𝘁𝗲𝗳𝘂𝗹; 𝗶𝘁’𝘀 𝗶𝗻𝘀𝗶𝗴𝗵𝘁𝗳𝘂𝗹. Every setback is an opportunity to ask, “What did we discover, and how can it guide us forward?” 2️⃣ 𝗦𝘆𝘀𝘁𝗲𝗺𝘀 𝗺𝗮𝘁𝘁𝗲𝗿. 𝗜𝗻𝗻𝗼𝘃𝗮𝘁𝗶𝗼𝗻 𝗱𝗼𝗲𝘀𝗻’𝘁 𝘁𝗵𝗿𝗶𝘃𝗲 𝗶𝗻 𝘀𝗶𝗹𝗼𝘀. It grows when we capture and share the lessons from every effort, even those we end. 3️⃣ 𝗪𝗲 𝗻𝗲𝗲𝗱 𝘁𝗵𝗲 𝗰𝗼𝘂𝗿𝗮𝗴𝗲 𝘁𝗼 𝗲𝗻𝗱 𝗳𝗮𝗶𝗹𝗶𝗻𝗴 𝗽𝗿𝗼𝗷𝗲𝗰𝘁𝘀. Courage to admit when something isn’t working and courage to trust that ending one thing can open doors to something better. Reading Rives’ story reminded me that progress isn’t always linear. Sometimes, it’s about creating fertile ground for what comes next. What’s one project, idea, or initiative you’ve let go of that helped you grow? I’d love to hear your thoughts. #chiefmarketingofficer  #Leadership #Innovation #Growth

The Rejection Email That Changed My (and the candidate’s) Career I just helped a candidate secure a job offer after he'd been rejected by the same company just three months earlier. How? The candidate did something most job seekers never consider. When he received the initial rejection, instead of quietly moving on, he sent a thoughtful response thanking the hiring manager for the opportunity and asking for one specific piece of feedback. That email sparked a conversation which eventually led to him being considered for a different role. This story highlights something I've observed repeatedly in my years as a headhunter: your response to rejection can be as important as your application. Here's what successful candidates do differently: 1. They view rejections as pauses, not stops. The hiring world is fluid—budgets change, requirements shift, and new positions open up. Maintaining positive connections keeps you in the loop. 2. They ask for targeted feedback. Don't request general improvement areas. Ask: "Could you share one skill I could develop that would make me a stronger candidate for similar roles?" This is specific and actionable. 3. They show growth between applications. If you reapply, highlight what you've learned or improved since your last application. This demonstrates commitment and adaptability. 4. They stay visible professionally. Comment thoughtfully on the hiring manager's LinkedIn posts or share relevant industry articles. This keeps you on their radar without being pushy. 5. They treat recruiters as long-term connections. A good recruiter remembers candidates who communicate professionally, even when things don't work out. We often come back to people who left positive impressions. I've seen too many qualified candidates vanish after a rejection, missing future opportunities. The job search isn't just about finding vacancies—it's about building relationships that last beyond a single application. #JobSearch #CareerAdvice #Recruitment