Leadership Challenges In Startups

One of the most important skills that one needs as a founder, and surprisingly, no one talks about it enough, is emotional intelligence (EQ). While we focus on growing our business, we neglect the very thing that can make or break our success: our ability to understand and manage emotions, both our own and those of others. It allows you to: - Create a positive company culture - Communicate effectively - Lead with empathy and - Navigate conflicts Here are 5 ways that helped me improve my EQ: 1. I pay attention to my emotions and how they affect my behavior and decisions. Regularly check in with yourself and be honest about your strengths and weaknesses. 2. In conversations, I try to focus on understanding others rather than just waiting to speak. The key is to listen for the underlying nonverbal cues, not just the words one says. 3. When faced with conflicts or challenging situations, I step back before reacting. This way, I can respond constructively and not impulsively to resolve the challenge. 4. This one takes time. Put yourself in others' shoes and try to understand their POV and feelings. It builds trust, strengthens relationships, and helps you lead with compassion. 5. Start seeing critics as opportunities for growth and not personal attacks. Seek out feedback from your team, mentors, and friends to improve yourself. Building your EQ is the best thing you can do for yourself, your team, and your business in the long run. #leadership #emotionalintelligence #mindset #growth

How to hire the right leader? Why it is important to set clear expectations with the leader before hiring them? For founders, who are scaling their startup, hiring a leadership team who can take care of each facet of your business and help you achieve the desired outcome is the hardest part. I was in this place a few years back and it was really exhausting to find the leader who is right for your business. Every leader has a different style of working and they might create scenarios on how to grow your business when they join. That’s great. But as a founder, you know your business well, you have some goals set that nobody can define or change for you. So, it is crucial that when you are hiring them, give them freedom to work as per their style but make sure whatever they do, how they do it, should be clearly aligned with the business goals, vision, and values. Here’s how I set clear expectations with them before hiring that might help you too. I look for someone: 1. Who not only understands but passionately resonates with our vision 2. Who comes with the right blend of expertise and unyielding commitment  3. Leader who complements my company culture rather than cloning it 4. Who is adaptable, open to growth, ready to steer you through rapid changing market. By following this, the chances of hiring a leader who turns out to be ineffective has reduced significantly for me. Today, I have leaders in my team who have been with us for 3+ years and have contributed significantly and are still counting.

𝗟𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 𝗶𝗻 𝗧𝗶𝗺𝗲𝘀 𝗼𝗳 𝗘𝗰𝗼𝗻𝗼𝗺𝗶𝗰 𝗨𝗻𝗰𝗲𝗿𝘁𝗮𝗶𝗻𝘁𝘆: 𝗣𝗿𝗮𝗰𝘁𝗶𝗰𝗮𝗹 𝗧𝗶𝗽𝘀 𝗳𝗼𝗿 𝗥𝗲𝘀𝗶𝗹𝗶𝗲𝗻𝗰𝗲 In today’s fast-evolving world, uncertainty is the only constant. From global trade tensions to rapidly shifting markets, CEOs—especially in financial services-are navigating a complex intersection of challenges. It is not just about managing internal changes; it is about responding to customer needs, adapting to disruptions, and leading teams through unpredictability. In my experience, leadership in these times isn’t automatic, it demands deliberate action, clear vision, and a purposeful approach. I’d like to share some strategies that I have used in my leadership journey to navigate uncertainty, build resilience, and drive success: •𝗟𝗲𝗮𝗱 𝘄𝗶𝘁𝗵 𝗧𝗿𝗮𝗻𝘀𝗽𝗮𝗿𝗲𝗻𝗰𝘆, 𝗖𝗮𝗹𝗺, 𝗮𝗻𝗱 𝗩𝘂𝗹𝗻𝗲𝗿𝗮𝗯𝗶𝗹𝗶𝘁𝘆: Leaders often feel pressured to have all the answers. However, acknowledging challenges and being transparent about what you know—and what you don’t—builds trust with your leadership team. By leading with calm and vulnerability, you create an environment where innovation and adaptation can flourish. •𝗘𝗺𝗽𝗼𝘄𝗲𝗿 𝗬𝗼𝘂𝗿 𝗟𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 𝗧𝗲𝗮𝗺: Ensure the C-Suite has the authority, resources, and support to drive their areas of the business. When your leadership team has autonomy, they are better equipped to make decisions that guide the organization through uncertainty. •𝗘𝗺𝗽𝗮𝘁𝗵𝘆 𝗮𝗻𝗱 𝗔𝗰𝘁𝗶𝘃𝗲 𝗦𝘂𝗽𝗽𝗼𝗿𝘁: Leadership isn’t just about strategy; it’s about understanding the pressures your team faces. Regular check-ins and support help your leadership team feel valued and equipped to perform with resilience. •𝗕𝗮𝗹𝗮𝗻𝗰𝗲 𝗦𝗵𝗼𝗿𝘁-𝗧𝗲𝗿𝗺 𝗔𝗰𝘁𝗶𝗼𝗻 𝘄𝗶𝘁𝗵 𝗟𝗼𝗻𝗴-𝗧𝗲𝗿𝗺 𝗩𝗶𝘀𝗶𝗼𝗻: addressing immediate challenges is important, great leaders keep the long-term vision in sight. Align your decisions today with the future goals to ensure your leadership team is always working towards broader objectives. •𝗘𝗻𝗰𝗼𝘂𝗿𝗮𝗴𝗲 𝗜𝗻𝗻𝗼𝘃𝗮𝘁𝗶𝗼𝗻 𝗮𝗻𝗱 𝗔𝗱𝗮𝗽𝘁𝗮𝘁𝗶𝗼𝗻: Uncertainty brings both challenges and opportunities. As a CEO, you must foster a culture where your leadership team feels empowered to innovate, take risks, and adapt to changing circumstances. Businesses that embrace change will thrive. •𝗕𝘂𝗶𝗹𝗱 𝗖𝗼𝗹𝗹𝗲𝗰𝘁𝗶𝘃𝗲 𝗥𝗲𝘀𝗶𝗹𝗶𝗲𝗻𝗰𝗲: Resilience thrives when teams work together. When your leadership team is aligned and resilient, the entire organization becomes better equipped to weather challenges and seize opportunities.  Leadership is about empowering teams, navigating uncertainty with clarity, and building resilience for long-term success. By embracing these values, we can shape a future defined by trust, innovation, and strength. How are you empowering your teams to rise above the challenges of today? Let’s continue the conversation-share your thoughts on leading through uncertainty and how we can all adapt and thrive.

After 20+ years of coaching over 1,000 founders backed by all the major VC funds, I've boiled down my philosophy to 8 core principles: 1) You can't fix scale-up problems with start-up leadership Most founders double down on what made them successful in the start-up phase. Wrong approach. The scrappy, do-everything energy that got you to product-market fit becomes toxic when you need to manage 50 people. What got you here won't get you there. 2) Every founder needs three different leadership styles, not one Visionary leadership gets you started. Operational leadership scales the business. Strategic leadership builds lasting value. Most founders are stuck in one style. The survivors learn to switch between all three based on what the business needs. 3) Your biggest strength becomes your biggest liability I've seen brilliant entrepreneurs destroy their scale-ups because they couldn't stop micromanaging when they needed to delegate. Your superpower got you this far, but you need a full toolkit to go the distance. 4) Most "people problems" are communication problems Founders complain constantly about their teams, investors, and boards. But when you dig deeper, it's usually because they can't give feedback effectively or inspire followership. You need both management communication and influence skills. Most founders only have one. 5) Your emotional baggage is running your business, not you Your need for control, approval, or freedom that developed in childhood is making decisions for your company. That insecurity you've carried since you were 7? It's sabotaging your board meetings. Self-awareness isn't optional for leaders. 6) Physical and mental stamina is a competitive advantage Founding a company is a marathon, not a sprint. The founders who crash out aren't less talented - they're less disciplined about managing their stress, sleep, and emotional health. Taking care of yourself isn't selfish, it's strategic. 7) What you permit, you promote as a leader Every interaction is building your reputation. The late-night email you send while stressed, the way you walk into the office, how you handle conflict - it's all communicating to your team what you expect. Leadership is always "on." 8) The best founders treat themselves like their most important hire You wouldn't hire a CEO who had zero self-awareness, couldn't manage their emotions, or burned out every six months. Yet most founders never invest in developing themselves. Your business can only grow as much as you do. TAKEAWAY: Most founders think success is about product-market fit, fundraising, and hiring. Those are table stakes. Real success is about scaling yourself as you scale your business. The founders who master these 8 principles don't just survive the scale-up journey. They thrive through it.

When I first became an entrepreneur, one of my biggest challenges was learning how to lead a team. I quickly realized that scaling a team is about much more than just hiring talented people. Here are some of the steps I've found essential to growing a team: 1. Alignment Everyone has to be aligned on the company's mission and goals so that they're moving in the same direction. For leaders, this involves constantly repeating the company's roadmap and being transparent about goals and objectives. 2. The "mind melding" phase This approach may be more relevant for senior hires. Rather than granting complete autonomy from the start, I’ve found that a phased transition works better. I typically spend the first few months deeply involved in their work. During this period, I gain insight into their thought process, and they, in turn, understand my expectations and approach. Once we’ve established a mutual understanding, I gradually step back, confident that we’re aligned. 3. Independence and autonomy From there, I think one of the most important things you can do as a leader is get out of the way. If you want to attract and retain people who are self-starters and proactive, you have to give them autonomy. 4. Accountability and measurability The last step is to create accountability by checking in at regular intervals. Clear, measurable KPIs have to be part of the equation. In other words, independence is important, but it goes along with the expectation of producing concrete results. Building a strong team is an ongoing process that requires intentional effort, clear communication, and a balance between guidance and autonomy. You're not just scaling a company—you're building a culture where innovation isn't limited to just one person or their ideas.

Leading in uncertain times is a hot topic today in business as we face a compounding set of unknowns: tariffs, inflation, volatility in our financial markets, the ongoing climate crisis, supply chain disruptions, global conflicts, and the advent of AI to name just a few. Whether you are an operator, investor or board member, I wanted to share a few of my approaches to dealing with the reality we are facing, and I would love your thoughts in response: 1. First, for me, is to remain consistent and committed to our company values. At PSP Partners, we express ours as IDEALS--Integrity, Diversity, Excellence, Alignment, Leadership and Service. Your teams want to know that during uncertainty you will make hard decisions that are grounded in your core values. 2. Radical honesty is critical. Bringing your leadership team to a point of embracing the reality of the landscape that your organization is facing is an essential foundation to then figuring out the vulnerabilities. 3. Ensuring that your balance sheet is strong to weather the difficult periods as well as to have the opportunity to play offense is more essential than ever. 4. Regular scenario planning and pressure testing various outcomes is essential to manage and mitigate risk; it is all the more important right now. This is also known as “red teaming” and it’s a critical thing to do. 5. Being curious about your blind spots and institutional biases will help create an environment where you and your team can safely challenge assumptions. 6. Overcommunicating with your management team and to your company as a whole have never been more needed. Remember it takes about 7 times for a message to break through. Don’t be afraid to repeat it over and over. 7. Embracing the idea that challenges also create unique and unexpected opportunities is so important. During uncertainty the best companies create extraordinary opportunity and returns for the long term. 8. A strong, innovative and resilient culture is always foundational and especially essential to navigating the current challenges. The CEO and your leadership team have to set the example.  

Conflict gets a bad rap in the workplace. Early in my career, I believed conflict had no place in a healthy workplace. As I progressed, I realized that it was quite the contrary. The lack of conflict isn't a sign of a healthy work culture, rather it is an indication that important debates, discussions and differing viewpoints are being disregarded or suppressed. This insight revealed another key aspect: high-performing teams do not shy away from conflict. They embrace it, leveraging diverse opinions to drive optimal outcomes for customers. What sets these teams apart is their ability to handle conflict constructively. So how can this be achieved? I reached out to my friend Andrea Stone, Leadership Coach and Founder of Stone Leadership, for some tips on effectively managing conflict in the workplace. Here's the valuable guidance she provided: 1. Pause: Take a moment to assess your feelings in the heat of the moment. Be curious about your emotions, resist immediate reactions, and take the time to understand the why behind your feelings. 2. Seek the Other Perspective: Engage genuinely, listen intently, show real interest, and ask pertinent questions. Remember to leave your preconceived judgments at the door. 3. Acknowledge Their Perspective: Express your understanding of their viewpoint. If their arguments have altered your perspective, don't hesitate to share this with them. 4. Express Your Viewpoint: If your opinion remains unswayed, seek permission to explain your perspective and experiences. Remember to speak from your viewpoint using "I" statements. 5. Discuss the Bigger Objective: Identify common grounds and goals. Understand that each person might have a different, bigger picture in mind. This process can be taxing, so prepare beforehand. In prolonged conflict situations, don't hesitate to suggest breaks to refresh and refuel mentally, physically, and emotionally. 6. Know Your Limits: If the issue is of significant importance to you, be aware of your boundaries. For those familiar with negotiation tactics, know your BATNA (Best Alternative to a Negotiated Agreement). 7. Finalize Agreements: Once an agreement has been reached, continue the engagement to agree on responsibilities and timeframes. This ensures clarity on the outcome and commitments made. PS: Approach such situations with curiosity and assume others are trying to do the right thing. 🔁 Useful? I would appreciate a repost. Image Credit: Hari Haralambiev ----- Follow me, tap the (🔔) Omar Halabieh for daily Leadership and Career posts.

One of the biggest transitions in any career is going from manager to leader. It sounds simple—but it’s a powerful shift, and it doesn’t happen overnight. When you’re managing, your focus is execution: making sure the work gets done, hitting deadlines, solving the immediate problems. But leading? Leadership is about vision. It’s about stepping back to see the big picture—and helping others see it, too. Here are a few shifts I’ve seen (and lived) over the years: ✔️ From taskmaster to culture shaper: Leaders connect the work to something bigger. They help people understand why their work matters—and how it ladders up to a shared mission. It’s not just about getting things done. It’s about creating an environment where people feel energized and encouraged. Where they can grow, feel heard, and want to show up and contribute. Culture doesn’t just happen—it’s shaped every day by what leaders choose to emphasize and how they show up. ✔️ From solving problems to asking better questions. You don’t need to have all the answers. In fact, you shouldn’t. Leaders create space for new ideas and unexpected solutions. That means asking better questions, being curious, and letting new information shift your thinking. When you lead with curiosity instead of certainty, you get better outcomes—and better relationships. ✔️ From managing outcomes to investing in people. The best leaders I know care about performance—and they care just as much about potential. They give people opportunities to build on their strengths. They invest in development. They make space for mistakes, because they know that’s how learning happens. Leadership isn’t about perfection—it’s about helping others grow into their own leadership, too. So if you’re in the middle of this shift, here’s what I’ll say: trust the process. Let go of control. Listen more than you speak. Support more than you direct. Because at the end of the day, people don’t follow job titles—they follow clarity, trust, and purpose. Anyone who has made this transition, what are other shifts and advice you would give?

I realized this during a team meeting when a team member shared how their development led to impressive results. It struck me that investing in our people is the true measure of success. Many organizations overlook this crucial shift: They chase metrics but neglect the very heart of their business— their people. Think about it. Are you focusing on: → Employee engagement → Skill development → Mentorship opportunities → Team collaboration → Creating a culture of trust Neglecting these elements stunts growth and innovation. The good news is that fostering people-first leadership is a choice. You can make it part of your organization's culture. Here’s how to get started: 1. Prioritize personal development for your team. 2. Encourage open communication and feedback. 3. Celebrate individual and team successes. 4. Invest in training and mentorship programs. 5. Create an environment where everyone feels valued. Remember, leading by growing people means nurturing their potential while driving your organization forward. So, what steps will you take today to invest in your team's growth?