The hardest leadership skill I've had to develop is the ability to delegate the outcome rather than the method. Basically, I had to learn how to stop being a bottleneck. When I started flipping houses in Cleveland, I was a control freak. I thought that to ensure quality, I had to be on the job site every morning, watching over shoulders. I remember one specific project in Lakewood where I was literally standing there correcting how the crew was installing baseboards. I thought I was being helpful and ensuring high standards. The turning point came when my lead contractor pulled me aside. He told me bluntly that my constant hovering was slowing his team down and killing their morale. He said, "Nick, you can be the investor or the foreman, but you can't be both." That hit home. I realized my need for control was costing me money and damaging relationships with the people I needed most. I had to consciously force myself to step back. Now, I focus entirely on the front end: setting extremely clear scopes of work, defining the exact materials, and setting hard deadlines. Once we agree on that, I get out of the way. I forced myself to stop visiting sites daily and switched to weekly milestone inspections. It was uncomfortable at first to let go, but the result is that my projects move faster now. My contractors take more ownership of their work because they know I trust them to solve the problems, and I have the bandwidth to manage multiple projects instead of just obsessing over one.
The one leadership skill I've had to consciously develop is active listening with the intent to empower, not to immediately advise. When you start a business like Honeycomb Air, you're the expert technician who knows how to solve every single problem. The natural instinct is to jump in and fix things, which makes you a good mechanic but a terrible leader. I had to learn to shut up, let my team struggle slightly, and only then ask questions that guide them to their own solution. This was a huge shift because I had to move from being the company's best problem-solver to being the company's best coach. For example, we had a recurring issue with scheduling service calls across the far ends of San Antonio. My initial instinct was to write a new company policy outlining the routes myself. Instead, I forced myself to step back. I pulled the dispatch team and the lead technicians together and just listened to their frustrations and ideas for two hours straight. By actively listening and giving them ownership, they developed a far better, more streamlined zoning system than I ever could have come up with alone. My job wasn't to solve the problem; it was to provide the space, the data, and the support for them to solve it. That lesson—that leadership is about maximizing the capacity of the team, not displaying my own—has been the most valuable growth I've had as the owner of Honeycomb Air.
The leadership skill I've had to work on—consciously, repeatedly—is shifting from being driven by fear to being driven by intention. Sounds simple. It's not. My behavior used to be determined far more by what I wanted to avoid than what I wanted to create. A moment that cracked me open was losing my entire company in Chile. Overnight, 50 employees were out of work, my titles disappeared, and I was staring at a future I didn't choose. That experience forced me to look straight at the fear I'd been running from—fear of failing publicly, fear of not living up to my family's legacy, fear of letting people down. So I started doing the uncomfortable work: therapy, honest conversations, interrogating the difference between my goals and my fears. And the shift was subtle but powerful. Instead of running from failure, I began preparing for success. Instead of trying to avoid collapse, I started building for resilience. That's why today my wife and I live frugally, save aggressively, and build businesses that can withstand chaos. It's not fear—it's clarity. A concrete example? When I pitched one of my biggest contracts this year, I prepped harder than anyone else. But I also released my attachment to the outcome. My expectation wasn't "win the deal." It was "perform at my highest level." If I lost, I'd still sleep well. That mindset didn't just make me a better leader—it made me a calmer one.
Let me share my thoughts with you about the leadership skill that requires intentional development. The one leadership skill that I worked hard to build and develop consciously throughout the years has something to do with helping me and my team practice and learn to question our own assumptions. I realized early on that most of the disagreements among our team and the unproductive debates we've had weren't really about the facts at hand but more about the implicit assumptions that each of us holds individually. I first felt the urgency of rectifying this issue during our hyper-scaling phase when every project we undertook got caught up in conflicting "shoulds" and invisible expectations. Everyone ends up investing energy in defending one's position instead of looking for the needle in the haystack for the real culprit that's holding the project. We trained ourselves to pause and conduct an assumptions audit as a regular step in our workflow to break this vicious cycle. It sounds cliche but in practice, it's a very challenging exercise in discipline. So every time our postmortem or project planning runs into hurdles, instead of pushing through, we ask "What am I assuming to be true in this situation? Is its opposite statement at least as true as this one?" We stage our assumptions on trial and our defense of it made us realize that most of the time, our truths are just inherited assumptions that we're projecting. For me, one of the long-held assumptions I managed to dispel was the belief that rigidly codified processes are a non-negotiable requirement for consistent deliverables. In fact, when I challenged this assumption with the team and we tried giving more autonomy based on outcomes to people with a long tenure, our project completion delivery dates dropped significantly (14 days to 9.8 days) without increasing errors. We also experimented with using the opportunity to commit shared beliefs as a team, such as agreeing to promote candor over gossip, be more revealing than concealing, and choose curiosity over certainty to cultivate a reality-rich culture. I had to incorporate trust-building practices, such as the trust question prompt: "In order for me to trust you more, I need you to ___" in our retros, to ensure that our reality-rich culture doesn't devolve into a toxic environment. Now there's less drama and blame games and instead a reality-rich culture where calling people out is the norm and the only way for us to move forward.
One leadership skill I've had to consciously develop over time is learning to not jump into every problem myself. As a founder, especially in the early days of Eprezto, my instinct was to fix everything, every bug, every customer complaint, every small operational issue. It felt like that was my job, but all it really did was slow the team down and create a bottleneck around me. A clear example was when we kept getting requests from users who didn't match our ideal self-serve customer profile. My instinct was to redesign parts of the flow to "help everyone," but the data showed those users weren't the ones driving growth. Fixing edge cases would've been a distraction. So I made myself step back and let the team focus on the 20% of issues that actually moved our north-star metric. It wasn't easy, it feels uncomfortable to deliberately "ignore" certain fires, but it forced me to trust the team and trust the strategy. And once I stopped trying to solve everything, the team stepped into more ownership. They didn't wait for me to make every decision, and our velocity increased dramatically. It's a skill you build slowly: choosing which problems truly matter, and letting the rest burn a little. But once you learn it, you become a far more effective, and calmer, leader.
One leadership skill I've had to consciously develop is communication that builds trust beyond my team. In a hyperlocal business model like mine, you're not just leading employees, you're leading a community relationship. I used to think reliability would be clear on its own. But I learned to explain constraints, timelines, and options clearly. This way, local builders and farmers can plan their work without surprises. I improved this by speeding up our update rhythm. Each message focused on the local job context. "We'll try" feels vague and stressful, but "here's what we can do next" builds confidence. The result is fewer fire drills, calmer days for the team, and customers who treat you like a partner, not a vendor.
One leadership skill I've had to consciously develop over time is humility. Coming from a product and startup background, I was used to trusting my instincts and moving quickly. In the nonprofit fundraising space, that approach only works if it's paired with real listening. As RallyUp grew, I learned that slowing down and staying open mattered more than being right. Nonprofits were living these challenges every day, and their feedback often surfaced needs I hadn't considered. Getting comfortable with that shift changed how I showed up as a leader. A concrete example was how product decisions started being made. Instead of fitting ideas into what I thought the platform should be, we created more intentional feedback loops and let nonprofit experiences guide priorities. That adjustment made me a better leader and made RallyUp a stronger partner to mission-driven organizations. It reinforced that leadership isn't about having all the answers. It's about learning alongside the people doing the work.
The leadership skill I've had to consciously develop is asking questions instead of giving answers. This doesn't come naturally to many high-achievers, and I'm no exception. Early in my career, my value came from having solutions. Clients hired me to fix problems, so I showed up with expertise and recommendations. But that approach has serious limits: it creates dependency, not capability. Organizations don't transform when the consultant is the hero. I had a partner who listened for "pain points" and always jumped to the same solution to fixing everything. His solution was often not what the client needed of was looking for. I always listen for the the "why is that happening? and how can we get to the root cause of the why. The turning point came when I started teaching coaching methodologies at Transformance Advisors. We teach how great coaches focus on the problem-solver's growth, not their own ego. The coach's job is asking powerful, open questions that spark critical thinking, questions like "What have you tried?" "What's holding you back?" or simply "What else?" This requires genuine presence and the discipline to stay curious rather than jumping to solutions. Better questions created improved results. Students in our programs started completing more successful projects, one client trained 37 employees who launched 11 projects valued at $1.9 million. Multiple graduates earned promotions directly tied to the project work completed as part of their training class. Students don't get promoted when I'm the one solving the problems. It happens when I ask the right questions and create space for others to discover their own capabilities. This skill continues to require conscious effort, but it's transformed how I lead.
The Leadership Identity Architect at Jim Carlough Author, Leadership Consultant, Speaker
Answered 3 months ago
Empathy is one characteristic that took a long time to develop, especially heart felt empathy. Early in my career i sort of tuned out the noise in the background, but actively listening to the discussions of employees around you will open your eyes when someone is troubled or struggling. I also integrated in every 1:1 or check-in sessions routinely asking, how the individual was doing, as well as asking about their family as well. One real example came up in one of my regular 1:1 meetings with a manager who happened to be a single Mom, with an absent ex-husband/father, why she hadn't taken time off this summer to be with her son (12 years old). Her response was she was too busy. I stopped her and said we need to make the time, your son deserves that much. Our routine meeting was on Wednesday's early in the morning. I told her that by noon that day she was to shut down her computer and not turn it on until Monday morning. I also said I would not charge her PTO time either. I knew she wasn't expecting that by the emotional reaction, but to this day I stand by that decision. I was her manager, her back up, and remembering that my role is not only to manage the business, but to manage and ensure our team and family members are cared for. Had this been in the early years of my management career, I would not have known to even ask those questions.
I believe that every leader has a "thread" that runs through their career. The thread is the cluster of behaviours that they need to keep working on throughout their career. It's their journey of self-mastery and it extends beyond a leadership competency. It is a life long pursuit about how they become more skilled at relating to others. For me, my thread has always been having faith in positive outcomes. I have had to retrain my mind to see positive possibilities, expand ideas, and believe that the best case scenario could indeed come true. I have a picture of a leader on my white board with the word "faith" written across it, so I am reminded every day how important this is. I have always been optimistic and goal oriented, but faith is different. It's looking in the mirror and saying: "Why not me?" When leading a team: "Why not us?" Here, I am referencing achieving extraordinary things. Of course, it is in the realm of possibility that I / we can be part of the success team. This self-inquiry helps me to sign up for things that others might not. It has led me to coaching and leading peer groups for CEOs, Ambassadors and Ultra HIgh Net Worth Leaders. It has prompted me to write books, run international retreats with CEOs and shamans, lead Social Change initiatives, make that phone call to a celebrity judge for national contests, and learn new technologies that feel overwhelming. Faith helps me tackle big challenges and it invites presence. When I support my clients I do so with heart. I don't try to prove myself, but rather try to bring my full presence and care to their issue or opportunity. This has been an intentional journey that has taken practice and commitment. This relationship with my inner-self is my most important leadership quality. And, it benefits vision, strategy, influence, presence and well being.
Letting go, and it isn't even particularly close. I don't think I'm alone in saying that early in my career, I felt responsible for everything, which often meant hovering more than helping. Your scope of responsibilities is still narrow at that point, but as you gain more responsibilities it can become crippling. To fix this, I've worked hard on shifting away from that mindset by setting clear expectations and then genuinely trusting people to own their work. Sounds easier than it actually was, but a good example of this was handing off a full content initiative to a team member and then just letting them do it, aside from a final sign off. Unthinkable in my early days, but a necessity as I've gone beyond the point where doing things myself is time and cost-effective. It worked well in any case, as they brought fresh ideas and executed beautifully. That experience reminded me that leadership isn't about control, but more about creating the right space for others to do their best work.
I used to think leadership began once someone gave you permission. A title. A team. A meeting invite. It does not. It starts the moment decisions slow down and you choose to step in. The skill I had to learn was assertive communication. Not being louder, just being clearer. Early on, I softened every sentence to keep everyone comfortable. It felt polite, but it slowed everything down. Over time, I learned to make the call, explain the reasoning, and accept responsibility if it went wrong. I practiced this by running client reviews and giving direct feedback even when it felt uncomfortable. Repetition helped. You say the thing plainly, own the outcome, and keep moving. Leadership, for me, is mostly about absorbing friction so others do not have to. It does not require a title. It only requires someone willing to decide.
One leadership skill I've had to consciously develop over time is empowerment. I've learned that empowering others not only helps them grow but also strengthens the overall team dynamic. A specific example of this is when I was leading a team meeting and noticed that some team members hesitated to share their ideas. To improve in this area, I actively worked on creating an environment where everyone felt valued and confident to contribute. I encouraged open dialogue, asked for input directly, and recognized individual contributions. Over time, this approach fostered a culture of empowerment, leading to more innovative solutions and a more engaged team. Developing this skill has taught me the importance of trust and support in effective leadership.
Learning to Listen Before Solving One leadership skill I have worked hard to develop is active listening. I learned the importance of not jumping straight into problem-solving. In the past, I thought being a leader meant having all the answers. This often led me to respond too quickly, sometimes addressing the wrong issue or missing important context. To improve, I made a conscious effort to slow down my responses in discussions. During reviews or one-on-ones, I began by asking clarifying questions and summarizing what I heard before sharing my thoughts. This habit helped me see the issue from the other person's perspective instead of relying on my assumptions. A specific example occurred during a disagreement about how to present data versus the depth of the narrative. Rather than making a quick decision, I asked each side to share their main concerns. This revealed worries about user confusion on one side and loss of trust on the other. Once those fears came to light, the solution became clear. Over time, this approach improved the quality of decisions and built trust. People felt heard, and discussions became more productive. For me, leadership shifted from being about control to creating space for better ideas.
One skill I've had to develop over time is leading by example. If you want others to follow, you have to do as you ask. If you want your team to be mindful, take breaks and recharge to be at their best, their leader needs to do the same. By doing so, they know that their leader supports these values without having to verbally remind or ask them.
Leaders should have a vision, self belief, and charisma to achieve their goal. These are the ideals everyone talks about, but most people underestimate the importance of staying focused on strategy while not dwindling into the abyss of tactics. Being a small business leader, I have seen myself losing focus and balance in between strategy and tactics. I have been developing this extremely important leadership skill by synergizing risk-taking, team building, relationship building, managing business finances, being customer-centric, and above all believing in myself. Recently, in my company, we had to decide on launching new products and improving the existing ones during this period of AI chaos. The first thing I did was to spend most of my energies on making key decisions instead of trying to go deep into execution part. I believe, this approach has changed our perspective and our team is now aligned, motivated, and delivering better products to the customers.
We were able to scale our business very quickly. We hired employees as we needed more help, but we fell short on delegating some responsibilities. We kept the reins to the company close, a bit too close maybe. Being the president of the company, this was my fault and my problem to fix. Once I recognized this issue in my leadership approach I made a conscious effort to change it. But I kept finding myself slipping back into my old ways. Just wanting to change wasn't working, it wasn't enough of an effort on my part. Most of the issue was my deep-routed fear that "if I didn't do it myself, it wouldn't get done correctly." This fear prevented me from delegating responsibilities. Even though I wanted to delegate more of my work load, my fears kept me from implementing a solid plan. I decided to work this new effort into my daily schedule. The first thing I do every morning at 8am is to go through my work load and see what I can hand off to an employee. At first I felt like I hoarder parting with my prize possessions, but after time it became more normal to me. What helped me significantly was I make sure I spend the time to train people on each task, and make sure it gets done the way I want it done. I discuss the pitfalls of taking shortcuts to prevent an employee from making the same mistakes I already made and learned from. This has subsided my fears of it not getting done correctly, made me more likely to hand off responsibilities, and freed up my schedule so I can focus more on the tasks that remain in my work load.
I needed to master the art of delayed response as a crucial leadership skill. I tackled issues by taking swift action, which resolved immediate concerns but encouraged my teams to escalate every matter to their superiors. I addressed this by enforcing a moment of pause before stepping in. I asked team leaders to propose their solutions along with potential trade-offs before I began my evaluation. This shift in ownership empowered lower levels of the organization, leading to improved decision-making. The results reduced bottlenecks and fostered leadership skills, allowing employees to thrive independently without requiring constant oversight. Albert Richer, Founder WhatAreTheBest.com
I pride myself on being a good problem solver, but I've learned that I can just jump in to solve a problem as soon as I hear about it. Early on in my career I thought that a leader needed to be quick to solve problems. But the problem with that is it didn't let anyone else offer up ideas that might've been better than mine. So I've had to work on active listening first before acting to problem solve. The way that I've worked on this is to ask questions instead of just offering up solutions. This has been really effective when the problem has been presented in a meeting or group. I just ask what's been tried to solve the problem that didn't work, which leads to others asking good questions. And that ends up in us coming to better solutions as a team. Of course, this means giving up a little control, which was a bit uncomfortable at first but I think in the end it's made me a better leader.
I've had to work at learning to pause before reacting. In my younger days in the career, I was always leaping in with a solution when a project got behind schedule, before I even stopped to think. It wasn't until later I started to realize that my sense of urgency often ended up putting the team under entirely too much pressure. So I made a conscious effort to slow down a bit by always asking myself 2 basic questions whenever things started getting tense, what's really the problem, and what do I need to do right now to help this out? A few months back, we were in the middle of a product launch and hit a snag, rollout was delayed. And you know what, instead of just pushing the team to get it done faster I took a step back and had a sit down with them to figure out what was going on. That simple 20-minute conversation with the team ended up revealing a tiny but pretty big workflow gap, and fixing it saved us a bunch of time later on. By learning to pause and take a breath I think I've become a lot more down to earth and my team trust me a whole lot more.