Overcoming Second-Guessing in Decision Making

There’s a very specific moment when a founder starts doubting a new hire. It doesn’t happen on day one. It shows up a few weeks in, once the excitement has settled and reality starts arriving. The signals are small. They ask for more context than expected. They hesitate before making calls you assumed they’d own. Work moves, but it needs a bit more follow-up than feels comfortable. Nothing is clearly wrong, but nothing feels as easy as it should. And a thought starts forming, quietly but persistently: did I get this hire wrong? From that point, everything gets interpreted through that lens: the next delay reinforces it, the next hesitation confirms it, and you find yourself paying a bit more attention to their work than everyone else’s, trying to decide whether what you’re seeing is normal or a problem. What’s harder to see is what was already there before they arrived. Not obvious dysfunction. Just the kind of ambiguity people have learned to navigate over time, where things get done because certain people know how to move them forward, not because the path is actually clear. A new hire doesn’t have that map yet. So they slow down, ask more questions, and try to understand how things actually work. And that hesitation gets read as underperformance. Sometimes the hire isn’t right... but there are also cases where the doubt shows up before the company has made it possible for that role to work, and once that framing sets in, it becomes very hard to see anything else. By the time it gets questioned, the conversation is already about performance. What changed in your company the last time that doubt showed up? #Leadership #Scaling #Founder #Operations #OperatingModel

I lost 4 months in build mode by ignoring this ENTJ truth. If you've followed me, you know I talk about personality types. I may be a bit obsessed, but also, I've watched founders waste years building businesses that fight their wiring. Here's what most people miss: Your personality type isn't just about whether you’re introverted or extroverted. It's the invisible operating system running every business decision you make: How do you make decisions: data first or gut feeling first? What energizes you: collaboration or deep solo work? What drains you? Settings where you have to be extraverted or episodes of extreme solitude? Ignore this, and you'll build a business that looks successful on paper but feels impossible to sustain. I'm an ENTJ 8w7. That means: I make decisions fast. I'm energized by external input and impact. I need proof I'm making a dent. So when I spent 4 months in solo "build mode" with no team, no feedback, no external validation, I started to question everything. I had a vision, but isolation was killing me. ENTJs are wired to lead, strategize with others, and see measurable impact. That’s why consulting checks out, it works. But, building in isolation dosen’t. It isn't just hard for us. It's biologically draining. But I didn't realize that's what was happening. I just thought I wasn't working hard enough. So I did what high performers do when something feels off: I built more. Another pre-launch LinkedIn post. Another funnel. Another pivot. I convinced myself I was "almost ready.” Really? I was avoiding putting anything imperfect into the world. Here's what snapped me out of it: I stopped building and started researching. I got on calls with 50+ people. Asked questions. Heard what they actually needed vs. what I thought they needed. Suddenly: I had external feedback. I had proof people cared about what I was building. I had clarity on what to build next. That shift from isolation to interaction wasn't just a strategy change. It was me finally working with my wiring instead of against it. Here's why this matters for you: Most business advice assumes we all operate the same way. "Just build in public." "Just niche down." "Just post every day." But if you're an introvert, building in public might drain you so much you quit. If you're high in openness, "niching down" might feel like suffocation. If you need deep work to think clearly, daily posting might kill your creativity. Entrepreneurship has no rules, So why do many coaches try to inflict their systems on you without knowing who you are? The question isn't: "What's the best business model?" It's: "What business model can you actually sustain?" Here's what I'm curious about: What strategy are you forcing yourself to execute that completely drains you? Daily LinkedIn posts? Building in silence? Networking calls? Drop it in the comments. Let's see if it's a skill issue or a wiring issue.

I’ve made hundreds of mistakes as a leader over time. Here are my top 10 lessons from my epic fails 1. I hired a leader who had a great CV and rushed the interview process. Others were raising their hand to do the job. I didn't give them the chance. They quit. Look at what you've got first before looking to hire about. Internal progression often trumps the glitzy CV. 2. I told my team they could be vulnerable and tell me when they were struggling. I never told them when I was struggling. People thought I was being fake. I was. 3. Told people I care about their progression. I didn't have progression plans for any of them. They started looking for jobs in companies that took progression seriously. Following through is critical. 4. I said to my team that when they are off on PTO, they shouldn't answer emails or Slack messages and they need to recharge. When I was on PTO I did the opposite. People were confused and felt they needed to do the same. Leading by example is underestimated. 5. I used to use 1-1s as updates from direct reports. 1-1 time is not my time. It's your time. Always come prepared ask for help where you need it. My job is to unblock you and let you do your thing. 6. I once fired someone and they were shocked. I never gave them direct feedback and felt like they should know they were failing. They didn't know. I think about this almost every day. Direct, constructive feedback is critical. 7. I once took the credit for an entire rebrand. I barely had a part to play in it. Our entire Marketing team worked through the night for weeks to get it done. None of them were publicly praised for what they did. The effort dipped after that. Recognise people and show them how the work they do contributes to the business. 8. When we hit $10m ARR I didn't celebrate hitting such a big milestone. Instead I focused the team on getting to $100m ARR. We didn't even take a moment to appreciate what we'd achieved. Celebrate the wins. Particularly the big ones. You don't get that chance again. 9. I once witnessed someone make a homophobic comment in an internal meeting. I thought their boss would address it as I didn't manage them directly. They didn't. A Glassdoor review appeared from an employee who felt like leaders didn't care about protecting their people. Step in even when it's not your job. 10. As we got bigger I started to take more of a back seat. I expected others to bang the drum and set the pace. I didn't make this clear that this was an expectation. I also realised that if I took my foot off the pedal, others would do the same. Set clear expectations. Document them. And make sure you always "amp it up". This post is inspired by Nick Bennett

Most team performance problems aren't actually performance problems. When a team is underperforming, the instinct is to look at the people or find out where to place the 'blame'. Are they the right fit? Are they motivated? Do they even care or want to be here? But more often than not, the problem isn't the people. It's the environment they're operating in, and it almost always comes down to one of three things. 1. Nobody actually knows where they're going 🗺️ Not in a vision-board sense (although a north star in important too!), but just day to day. Things like, how do decisions get made? Who owns what? And what does 'good' looks like? When there's no clear ways of working, people fill the gaps with assumptions, with workarounds and then with a lot of wasted energy. The team looks misaligned because they are misaligned. So they may not be 'bad' at their job, it's just that no one shared the roadmap with them. 2. The founder is the bottleneck (sorry, not sorry) 🛑 This one's uncomfortable, but it needs to be said. If every decision, big or small, runs through you, your team simply can't grow, and then neither can your business. You end up drowning in performance conversations, quick fixes, and daily fires while the actual work of leading and growing the business sits untouched. The team isn't underperforming but they're waiting, and waiting, and waiting... 3. The wrong hire in the wrong structure 🚧 This is the expensive one. A founder recognises things are breaking, so they hire someone to fix it. A Head of People. A Senior Something. A GM. But the structure that caused the problem in the first place is still there, and now this new person is trying to build something on an already shaky foundation. It's not a hiring problem, it's a sequencing problem. So before you move the goal posts with a team restructure, a new hire, or launch into another performance conversation, ask yourself which of these three is really at play (and yes it could be more than one!). Because the 'fix' will look very different depending on the answer. If your team feels harder to run than it should, let's talk 👋 Chloe Field reworkau #teamperformance #founders #performancebeforeheadcount #farfromHR

Why Effort Isn’t Moving the Needle Most teams blame slow progress on a lack of hustle. That’s rarely the problem. The real issue is friction at the point of entry. If a customer lands on your product and gets confused, they leave. If a new hire joins and can’t find clarity, they stall. Not because they’re lazy, but because your system is. ✅ The Fix: Subtract Before You Add Stop shipping more features. Start removing confusion. 💥For CEOs: Make onboarding obvious, not "impressive." 💥For Creators: Lower the barrier to the first interaction. 💥For Teams: Design for a 60-second win. Effort doesn’t scale. Systems do! As you navigate this week, don't just work harder; architect better. ------------------------------ 👉 New here or looking to scale your tech career through mentorship? Follow us, Concreap, for more systems-led growth. We remain intentional about you and your journey! 🤔 What’s one “maze” in your process you can turn into a straight line today? Seeking to build systems that scale, Inosuft Technologies is a good fit. #systemsthinking #mondayvibes #growthmindset #efficiency #leadership #scale #successtips

The best hire I ever made cost me nothing. It was deciding to get out of my own way. Most founders I work with at Series A aren't failing because of their product, their market, or their team. They're failing because they're still doing the job they were brilliant at two years ago, just at twice the speed and three times the stress. Here's what that looks like in practice: 👉 You're still in every sales conversation because no one closes like you do. 👉 You're still rewriting the strategy deck because no one frames it like you do 👉 You're still the de facto head of product, engineering, people, and anything else that matters. You're not a CEO. You're an operator with a CEO title. The transition from founder to CEO isn't about working less. It's about working differently. The skills that got you to £5M, speed, instinct, personal execution, actively work against you on the way to £10M+. What changes: 👉 Your job becomes making decisions, not making things 👉 Your leverage comes from your team, not your output 👉 Your time on the business matters more than time in it The founders who make this transition well don't suddenly become different people. They develop a new set of habits: how they spend their first hour, how they run their leadership team, and what they say yes and no to. The ones who don't make the transition? They raise another round, hire more people, and wonder why it's still not working. If your business feels like it's running on you rather than running itself, that's not a team problem. That's a signal. What's the one thing you're still doing that someone else should own?

He knew he was the bottleneck. That part wasn't the problem. The self-awareness was there. What followed it wasn't. Instead of hiring for the competency that would have actually relieved the pressure, he hired for capacity. Warm, willing, earnest people who wanted to help and genuinely meant it. Good humans, every one of them. Wrong hire, every time. Because the bottleneck doesn't need more hands. It needs someone who can actually own something without being taught how first. What happened next was predictable in hindsight. Every task that got delegated came back with questions. Every question required his time. His time was already the scarcest thing in the building. So the small things got handed off and the real work stayed exactly where it had always been... on him. The org got wider but it never got lighter. He didn't have time to train properly. Couldn't yet afford to hire what he actually needed. And because execution was stalling, the revenue to close that gap wasn't coming either. The trap was elegant in its cruelty. Bootstrap thinking that built the business became the exact ceiling that stopped it from growing. Eventually the pivot was the only door left open. Hiring for capacity when you need competency doesn't solve the bottleneck. It just gives it an audience. #Operations #Founders #ExecutionFriction #DecisionMaking #RubberDuckOps

6 Powerful Ways to Turn Your Performance Review Into a Career Opportunity! April—the start of a new financial year. And for many, appraisal season is here. In a time where conversations around #layoffs, #restructuring, and cost-cutting are becoming more common, one thing is clear: Making your contribution count is no longer optional—it’s essential. Because here’s the truth: Hard work alone isn’t enough. Showcasing your value is an art—and like any art, it requires preparation. Recently, one of my coachees reached out to me. Her organization is in the middle of the increment cycle, and she had a performance review coming up. She asked me a simple but powerful question: “How do I make sure my manager truly understands the value I’ve created this year?” I shared 6 things with him—and I believe these apply to all of us, regardless of frameworks, roles, or review cycles 1. Move from effort to impact Don’t just say what you did—highlight what changed because of it. #Results speak louder than #effort. 2. Capture your story, don’t rely on memory Over a year, it’s easy to forget wins. #Document your contributions—projects, initiatives, and moments where you made a difference. 3. Connect your work to the bigger picture Managers value #alignment. Show how your work supported team or business goals. 4. Back your words with proof Numbers, feedback, outcomes—bring #evidence that makes your performance undeniable. 5. Talk about #growth, not just goals achieved What did you learn? How did you stretch yourself? Growth signals future potential. 6. Prepare for “what next” A great review isn’t just backward-looking. Be ready to discuss your #aspirations and #nextsteps. The conversation ended with her saying, “I never thought of it this way.” And that’s the shift we all need. Your performance review is not just a meeting. It’s your moment to shape perception, demonstrate value, and define your trajectory. So don’t leave it to chance—prepare for it. www.eduonn.com #Eduonn talent advisory services enables organizations to build a high-performance culture through a fact-based, quantifiable, and sustainable performance management framework—while empowering people managers with the skills to set clear goals, deliver impactful feedback, and inspire teams to consistently achieve higher levels of performance. #AppraisalSeason #CareerGrowth #PerformanceReview #Leadership #WorkplaceSuccess #fractionalchro #hradvisoryservices #hrconsultingservices #familyoffices #cxoadvisor #drhrofficial #globalchro #shrmmena #nhrdndubai #nhrdnindia #startupmentor #startupadvisor #uaecxo #uaefounders #uaechairman #tophrconsultingservices #iim #topuniversitiesofuae #performancemanagementconsulting

You can backfill a role in six weeks. You cannot backfill trust. Every founder talks about "building a world-class team." Then they wonder why their best engineers leave the moment a recruiter calls. They treat retention like an HR problem instead of a leadership failure. 𝗬𝗼𝘂𝗿 𝗔-𝗽𝗹𝗮𝘆𝗲𝗿𝘀 𝗮𝗿𝗲 𝗮𝗹𝗿𝗲𝗮𝗱𝘆 𝗴𝗼𝗻𝗲. 𝗧𝗵𝗲𝘆 𝗷𝘂𝘀𝘁 𝗵𝗮𝘃𝗲 𝗻𝗼𝘁 𝘁𝗼𝗹𝗱 𝘆𝗼𝘂 𝘆𝗲𝘁. Here is what actually keeps top talent from walking: 1. 𝗚𝗶𝘃𝗲 𝘁𝗵𝗲𝗺 𝗽𝗿𝗼𝗯𝗹𝗲𝗺𝘀 𝘄𝗼𝗿𝘁𝗵 𝘀𝗼𝗹𝘃𝗶𝗻𝗴 → Not maintenance tickets. Not busy work. Real challenges that move the business forward. 2. 𝗔𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝗹𝗶𝘀𝘁𝗲𝗻 𝘄𝗵𝗲𝗻 𝘁𝗵𝗲𝘆 𝗿𝗮𝗶𝘀𝗲 𝗿𝗲𝗱 𝗳𝗹𝗮𝗴𝘀 → They see technical debt. They know what will break. Stop dismissing their warnings. 3. 𝗣𝗿𝗼𝘁𝗲𝗰𝘁 𝘁𝗵𝗲𝗶𝗿 𝘁𝗶𝗺𝗲 𝗹𝗶𝗸𝗲 𝗶𝘁 𝗮𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝗺𝗮𝘁𝘁𝗲𝗿𝘀 → Every "quick sync" is code for "I did not prepare and need you to solve my problem." 4. 𝗦𝗵𝗼𝘄 𝗿𝗲𝗮𝗹 𝗶𝗺𝗽𝗮𝗰𝘁, 𝗻𝗼𝘁 𝘃𝗮𝗻𝗶𝘁𝘆 𝗺𝗲𝘁𝗿𝗶𝗰𝘀 → "Your code shipped to 50K users this week" beats "Sprint velocity up 12%" every time. 5. 𝗦𝘁𝗼𝗽 𝗺𝗶𝗰𝗿𝗼𝗺𝗮𝗻𝗮𝗴𝗶𝗻𝗴 𝗲𝘅𝗽𝗲𝗿𝘁𝘀 → You hired them for their judgment. Let them use it or hire someone cheaper. 6. 𝗜𝗻𝘃𝗲𝘀𝘁 𝗶𝗻 𝘁𝗵𝗲𝗶𝗿 𝗴𝗿𝗼𝘄𝘁𝗵 𝗯𝗲𝗳𝗼𝗿𝗲 𝘁𝗵𝗲𝘆 𝗮𝘀𝗸 → Conference budget. Learning time. New tech. Growth is retention. 7. 𝗕𝗲 𝗯𝗿𝘂𝘁𝗮𝗹𝗹𝘆 𝗵𝗼𝗻𝗲𝘀𝘁 𝗮𝗯𝗼𝘂𝘁 𝘁𝗵𝗲 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀 → They can handle reality. They cannot handle being blindsided by layoffs. 8. 𝗖𝗿𝗲𝗱𝗶𝘁 𝘂𝗽, 𝗯𝗹𝗮𝗺𝗲 𝗱𝗼𝘄𝗻 → Most founders get this backwards. Then wonder why morale is broken. 9. 𝗠𝗮𝗸𝗲 𝗮𝗰𝘁𝘂𝗮𝗹 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻𝘀 → Nothing kills momentum like endless "alignment" meetings that align nothing. 10. 𝗙𝗶𝗴𝗵𝘁 𝗳𝗼𝗿 𝘁𝗵𝗲𝗺 𝘄𝗵𝗲𝗻 𝘁𝗵𝗲 𝘀𝘁𝗮𝗸𝗲𝘀 𝗮𝗿𝗲 𝗵𝗶𝗴𝗵 → Compensation. Promotion. Recognition. Show up when it actually counts. Your engineers will not remember your all-hands speeches. They will remember the Tuesday you threw them under the bus to save your face. 𝗣𝗲𝗼𝗽𝗹𝗲 𝗱𝗼 𝗻𝗼𝘁 𝗾𝘂𝗶𝘁 𝗷𝗼𝗯𝘀. 𝗧𝗵𝗲𝘆 𝗾𝘂𝗶𝘁 𝗹𝗲𝗮𝗱𝗲𝗿𝘀 𝘄𝗵𝗼 𝘁𝗿𝗲𝗮𝘁 𝘁𝗵𝗲𝗶𝗿 𝗰𝗼𝗻𝘁𝗿𝗶𝗯𝘂𝘁𝗶𝗼𝗻𝘀 𝗹𝗶𝗸𝗲 𝗮 𝗯𝘂𝗱𝗴𝗲𝘁 𝗹𝗶𝗻𝗲 𝗶𝘁𝗲𝗺. What retention mistake cost you your best engineer?

“I thought this would be easier.” I’ve heard that more times than I can count. And to be fair… I’ve thought it too. At the start, it feels pretty straightforward. You have the vision. You know what looks good. You understand your customer, your style, your point of view. You just need someone to help you “build it.” So you get a tech pack done, hand it over to a factory, and think… okay, I’ve got this from here. And technically, you can get pretty far like that. But this is where things start to get expensive. Samples come back and something feels off… but you can’t quite explain why. The factory asks questions you don’t fully understand. Your designer suggests one thing, the factory suggests another, and you’re stuck in the middle trying to make the call. So you do what most founders do. You stay in it. You make the decisions. You keep things moving. Another sample. A few changes. One more round, just to be sure. Because the assumption is: “If I stay close to it, I can control the outcome.” And in the early days, that works. But businesses built around the founder being the sole decision-maker aren’t built to scale. Because everything still routes through you. You become the filter. The approver. The problem solver. And even if you hire, if those hires are junior or unsupported, the decisions still come back to you anyway. You control the cashflow. So now you have more people… but no more clarity. That’s when it shifts from building a business to building yourself a job. Growth doesn’t come from doing more yourself. It comes from building a system that can function without you at the center of every decision. Because if you can’t step away without everything slowing down… you’re not running a company. You’re the best employee in it. And most of the time, this doesn’t start as a factory problem or a sampling problem. It starts much earlier. In how decisions are made, how direction is set, and how clearly that thinking is translated into the process. That’s the part most founders don’t see coming.