Leadership is hard. It’s a balancing act that demands a vivid understanding of the moment we’re in, while also keeping an eye on the horizon. As leaders, we need to know where we are and how to navigate through the immediate challenges we face. At the same time, we must stay true to where we’re headed, why it matters, and what it will take to bridge the gap between here and there.
The more focused we become on long-term objectives, the further removed we often become from the present reality. I’ve experienced it firsthand at various points in my career — so fixated on what’s next that I failed to notice the great white sharks circling or the storm clouds gathering behind me. Before I knew it, I found myself in hurricane-force winds — literally, at one point (a story for another day) — engulfed by circumstances I didn’t anticipate.
How do you avoid finding yourself adrift in a turbulent ocean, either stripped of your command or, worse, with your entire crew struggling to stay afloat in icy waters with no life jackets? The answer lies in building an organization that has everything covered from bow to stern. This means understanding your Stage of Development and surrounding yourself with damn good, if not great, talent.
Understanding the Moment You’re In
Great leaders understand success doesn't just come from having a compelling vision — you must also recognize the reality of the moment. Before you can steer the ship toward a distant destination, you need to understand your current coordinates, the conditions surrounding you, and the immediate dangers lurking in the water. Too often, leaders — especially those with a visionary mindset — become disconnected from the present, oblivious to the fact that the gap between where they are and where they aspire to be is widening.
Ignoring the current state can be disastrous. Market dynamics shift, unforeseen threats emerge, and internal weaknesses can go unnoticed until they erupt into crises. Staying grounded means regularly assessing the environment, having a pulse on what’s working and what isn’t, and recognizing that the path to the horizon may require course corrections. The further out your vision, the more you need to guard against losing touch with the day-to-day realities.
The Leadership Evolution: From Dinghy to Ocean Liner
No one becomes the captain of an Olympic-class ocean liner overnight. Leadership is a progression that starts with sitting on a dinghy — perhaps with a friend, sibling, or parent. Your boat is small, close to shore, and there isn’t much you need to prepare for. You’re all right there together, figuring things out as you go. If something bites the proverbial hook, you deal with it together.
As your business evolves, the stakes grow higher. Your ship gets larger and more complex, and you’re no longer right next to every challenge that arises. By Stage 5, you’re commanding a five-level ocean cruiser, with activity happening on multiple levels below deck while you’re busy navigating the open sea. To complicate matters, if you’re a visionary, you’re not just steering through familiar waters — you’re likely charting a course through cold, inhospitable regions, dodging icebergs and other lurking dangers.
At this point, the demands are no longer simple. The data you need is often either nonexistent or overwhelming or, more than likely, both. To keep moving forward, you need a crew who’s competent, committed, and capable — as well as 100% aligned with your purpose. You need coverage from top to bottom, from bow to stern, ensuring everyone is doing their jobs or getting the rest they need to be prepared for their watch (or for those hopefully very rare events when they need to go the extra mile to handle the unexpected).
The Importance of Surrounding Yourself with the Right Crew
As the ship grows, so does the need for exceptional talent. Surround yourself with individuals who not only excel at their roles but also care deeply about the company. They need to respect the boat and take pride in their own jobs as well as the safety and well-being of everyone on board. The leaders of damn good companies aren’t just “nice” — they’re confident, competent, and kind. They recognize the seriousness of their responsibilities, speak up when something is wrong, and are prepared for all-nighters when the situation demands.
It's worth noting that true kindness in this context doesn’t mean being agreeable. It means caring enough to challenge the status quo, to raise concerns when things feel off, and to do what it takes to first and foremost keep the ship safe and secure before getting it back on course. It’s the kind of care that goes beyond job descriptions and manifests in a genuine commitment to the collective journey.
Staying in Tune with the Moment
You’re at the helm of your ship, eyes fixed on the horizon, only to realize storm clouds and icebergs are dangerously close. Staying tuned in to the here and now means coming down from that high vantage point, mingling with the crew, and taking stock of the waters surrounding you. It’s about reassessing assumptions, making course corrections, and yes, sometimes even backtracking when the path ahead looks treacherous.
So, how do leaders navigate these waters? There are a few practices that can help keep the ship steady and on course:
- Monitoring gauges: Every complex system — whether a ship or a company — produces data that tells a story. A great captain keeps an eye on the horizon but doesn’t forget to glance at the instrument panel. Those gauges are crucial because they offer early warnings about the ship’s health, helping you spot potential issues before they escalate. In a business context, this means staying vigilant about key performance indicators and understanding what they’re telling you about the company’s state.
- Reality checks: Even the best leaders can fall into the trap of seeing what they want to see. It’s human nature. But exceptional captains make it a point to surround themselves with people who challenge their perceptions and help them see things as they truly are. Routine reassessments of the ship and the seas (your company and the market) help your plans to stay grounded in reality.
- Feedback mechanisms: No sailor wants to be thrown overboard, and no employee wants to be left in the dark. Great captains create an environment where the crew feels safe to communicate openly. The crew often has a better grasp of immediate issues, and their insights can bring challenges to the surface early. Encouraging this dialogue means building a culture where feedback is not just accepted but actively sought.
- Training and development: Entropy doesn’t only affect the ship — it also affects the crew’s skills and cohesiveness, especially during tough times. Great captains are disciplined about regular training and safety drills. These exercises ensure the crew can work together seamlessly when it matters most. Continuous development keeps everyone sharp and ready for anything that might come their way.
- Communication protocols: Clear communication is vital to the success of every organization, so it’s important to establish solid protocols around when, where, and how to communicate. To start, set up a disciplined meeting cadence for all-hands, department, team, and 1-on-1 meetings (consider annual, quarterly, weekly, and even daily check-ins). Also, determine how other forms of communication, such as Slack or email, should be used and when. Having clear protocols built in becomes key to managing unexpected and urgent issues well. With this in place, you’ll eliminate confusion and enable faster, more coordinated responses, helping everyone to confidently know their roles and how to reach out to others when a storm is approaching.
- Responsive structures: Responsive structures are about having systems in place that quickly highlight issues and challenges, allowing for timely adjustments. This involves designing workflows and processes that prioritize transparency and responsiveness. When your protocols are firmly established, including communications, high-priority "fire" moments are managed more effectively. That way, the captain (and the company) can steer away from danger at the earliest sign of trouble.
- Resilience building: The best captains prepare their crew for adversity, not just calm seas. Building resilience means fostering a culture of problem-solving and adaptability. It’s about learning from setbacks and creating an environment where the crew can take calculated risks, recover quickly from mistakes, and continuously improve. This resilience ensures the ship can withstand unexpected challenges and emerge stronger from storms.
No matter how skilled you are as a captain, there will be times when storm clouds and icebergs are just beyond your line of sight. Staying attuned to the present means regularly coming down from the bridge, engaging with the crew, and examining the waters around
you. It means being willing to reassess assumptions, make course corrections, and even backtrack if the path forward becomes treacherous.
It’s easy to become too absorbed in a distant horizon, but the best captains are those who balance a visionary outlook with an unwavering awareness of the present.
Leadership as a Continuous Journey
Becoming a damn good, if not great, captain is not a single achievement. It’s a continuous journey that involves learning, adapting, and growing through various stages of complexity. The process is not about reaching a point where you have it all figured out — it’s about building the skills to navigate the ups and downs, finding joy in the moments of calm, and persevering through the inevitable storms. It’s about understanding that while you may not have all the answers, you can rely on your crew, your experiences, and your capacity to learn from each situation.
A great captain doesn’t just steer the ship. They also inspire confidence in the crew and foster an environment where everyone feels responsible for the ship’s success. They take pride in the journey itself, knowing the trials they endure are part of what makes the destination meaningful.
The Beauty and Burden of Command
To be the captain of a five-level ocean liner is to carry both the beauty and the burden of command. It’s a role that goes beyond setting the course — it’s about ensuring the health and safety of the entire crew, even when the waters get rough. It’s about recognizing that no matter how far off the horizon lies, there will always be present-day challenges to address.
Ultimately, leadership is hard. It’s about finding the balance between a compelling vision for the future and a deep understanding of the present. It’s about making the tough choices, enduring the setbacks, and taking responsibility for every aspect of the journey. And for those who embrace it, there’s nothing quite like the feeling of being at the helm, surrounded by a crew that truly cares, and appreciating the beauty of life.
Great leadership isn’t achieved by accident. It’s earned through experience, dedication, and a willingness to confront the gap between vision and reality. And in that gap, the real work of reconciling the future with the present is done.
In this journey, remember that the vision is your destination, the moment you’re in is your guide, and the people you’re surrounded by are the only things you can depend on between you and the cold and unforgiving waters below. Keep these ideas in mind, and you’ll find that the path, while challenging, is also profoundly rewarding.
