44: Nick Notes – Leadership Lessons

Boost Your Career with Executive Leadership Coaching

You’ve climbed the ladder and hit a new level. But something feels different. The skills that made you a star contributor feel like they’re holding you back now.

What got you here won’t get you there. This is a common wall that many rising stars hit, and it’s where authentic executive leadership coaching comes in. It’s not about learning a new technical skill; it’s about a fundamental shift in your approach to leadership and your own professional development.

Getting to the top is one thing, but staying there and being effective is a different challenge. After nearly 4,000 coaching sessions, I’ve seen the same patterns emerge repeatedly. You can have all the smarts in the world, but it won’t be enough for long-term success without a strong foundation in leadership skills.

Today, I’m opening up my playbook from working with top executives to help you understand the core shifts that separate the good from the great. A quality leadership development plan is built on these principles. This is the unvarnished truth about what it really takes.

Table of Contents:

• The Two Biggest Hurdles for New Leaders
  • Are You Busy, or Are You Just Doing Two Jobs?
  • The Thin Air at the Top
• Executive Leadership Coaching: Learning to Speak a New Language
  • From Asking Permission to Informing Your Plan
• Why Yellow Lights Mean “Go”
• Hustle and Humility: The Winning Combo
  • The 360-Degree Review: Scary but Necessary
  • Hunting for Your Distinct Value
• Building a High-Performing Team Isn’t an Accident
  • Don’t “Set It and Forget It”
  • The Social Contract
• Conclusion

The Two Biggest Hurdles for New Leaders

When I start a new coaching engagement, two issues pop up almost immediately. The first one is being “busy,” a state that often masks deeper problems. The second is figuring out how to manage the people above them, a critical but frequently overlooked skill.

Are You Busy, or Are You Just Doing Two Jobs?

You just got a promotion, which is great news. But now you feel buried under a mountain of work. You’re likely still doing your old job on top of your new one.

It’s a classic trap for high performers. As an individual contributor, your instinct is to take on every task and say “yes” to everything because that’s what got you noticed. But that same instinct will bury you as a leader and stunt your team’s human development.

This approach leaves no room for strategic thought, which is your new primary function. This “busy” trap keeps you from truly leading. Your shadow looms over your team, preventing them from stepping up, and you fail to expand leadership capacity within your group.

An executive coach can be invaluable here, helping you see the pattern and develop new habits. Shedding that old skin is the first, and hardest, step. Learning what to say “no” to becomes even more important than what you say “yes” to, as that “no” could be a respectful delegation or simply dropping a low-priority task to improve performance overall.

The Thin Air at the Top

As you move up, you’ll find there are fewer people to turn to for answers. When you’re a mid-level manager, there’s a network of people and committees you can lean on for support. At the executive level, that network shrinks, and sometimes it’s just you and the CEO.

If you don’t get the right answer from them, there’s often nowhere else to go. This makes getting their attention and buy-in absolutely critical. Yet, many new leaders struggle to even get on their boss’s calendar, feeling like they’re a bother or unsure how to present their ideas effectively.

This is the challenge of “managing up,” a skillset distinct from managing a team. It’s a key area where external coaches provide a confidential sounding board. They can help you strategize these conversations and build the confidence to engage with senior leaders effectively.

Executive Leadership Coaching: Learning to Speak a New Language

Managing up is less about authority and more about influence. It often comes down to changing your language and improving your emotional intelligence. A subtle shift in how you communicate can completely alter how your bosses perceive you and your readiness for more responsibility.

From Asking Permission to Informing Your Plan

At lower levels, you are trained to ask for permission. You present a problem and ask your boss, “What should I do?” This approach shows you respect the hierarchy and established processes.

But for a busy executive, this just sounds like you’re giving them more work. They promoted you to solve problems, not bring them more. This is where a language shift during a coaching conversation can be powerful.

Instead of asking for permission, start informing your boss of your intentions. A simple phrase can make all the difference. Try saying, “Hearing no objections, this is what I plan to do.”

This single change accomplishes a few important things. It shows you’ve thought through the issue and have a solution. It respects their time by giving them a clear plan to approve or amend, and it demonstrates confidence, a key executive trait.

As the Harvard Business Review notes, managing up involves consciously working with your superior to get the best possible results for you, your boss, and the company. You are simply showing you’re ready to take the lead. This is a core competency taught in many an executive education program.

Why Yellow Lights Mean “Go”

Busy leaders often give signals, not detailed instructions. You need to learn how to read them. When you get green lights and positive feedback, you know you’re on the right track.

But what about yellow lights? Many people see a yellow light as a reason to pause and wait for more clarity. This is often a mistake.

With a busy executive who trusts you, a yellow light almost always means “go.” They expect you to handle the details and move forward. In the absence of a hard stop sign, they want you to take action, so don’t wait around for someone to give you explicit permission for every single step.

Hustle and Humility: The Winning Combo

No matter how much technology changes business, some old-school principles never fade. Hustle still wins. You still have to outwork the field to truly stand out and prove your commitment.

But hustle without humility is just arrogance, and that will only get you so far. Humility is the real dividing line between a good leader and a great one. It’s not enough to be smart; you must be wise enough to know you don’t have all the answers.

True humility is being confident enough to admit you need to learn more. It’s what drives you to seek out honest feedback and continue your adult development journey. This brings us to one of the most powerful tools for a leader’s growth.

The 360-Degree Review: Scary but Necessary

Imagine asking every single person who works for you what they honestly think. You ask them what you’re good at and, more importantly, what you need to improve. It sounds terrifying, doesn’t it?

But it’s also one of the most impressive things a leader can do. It shows a deep commitment to growth and is a cornerstone of evidence-based coaching. Most leaders get tons of positive reinforcement because their direct reports want to please them.

You might get ten “great jobs” for every one piece of real, constructive criticism. A formal 360-degree process, often facilitated by human resources or an international coach, breaks through that noise. It gives you an unvarnished look at how you are perceived by everyone, providing a complete learning experience.

This kind of raw feedback is a goldmine. It might sting, but it’s what helps you identify the blind spots that could derail your career. Working through this feedback is a major part of successful coaching.

Hunting for Your Distinct Value

What makes you truly valuable to your organization? It’s probably not the technical skill listed on your job description. Everyone at your level has that core competency.

Your distinct value is the specific way you contribute that nobody else can. Are you the person who can calm a furious client? Or maybe you have a knack for seeing a market trend before anyone else.

This specific value proposition is what makes you essential. A great leader is always looking for this quality in their people. They aren’t afraid to reach down a few levels in the organization and pull someone up who has a special talent or operates in their sweet spot.

As you grow, you need to be just as intentional about finding and marketing your own specific value. If you’re just layering your skills on top of what everyone else does, you’ll stay employed. But if you can pair your skills with a contribution that is clearly yours, you become irreplaceable.

Building a High-Performing Team Isn’t an Accident

Great leaders don’t just assemble a group of talented people. They actively build a cohesive team, a process that requires ongoing effort and attention. This means looking beyond skillsets and focusing on the underlying dynamics of how people work together to foster effective leadership.

Don’t “Set It and Forget It”

A common mistake is building a team and then treating it like it’s finished. You distribute portfolios and create a structure that makes sense at the time. Then you forget about it for the next two years.

The business world doesn’t stand still. What worked last year might be broken today, especially in times of intense change management. A team structure needs to be fluid, and coaching professionals can help you see when adjustments are needed.

You have to be willing to reshuffle roles and responsibilities as facts on the ground change. Don’t be afraid to adjust things. Sometimes the same people just need to be in different seats on the bus.

Your best people should be working on your best opportunities, not your biggest problems. This might seem counterintuitive. But putting your stars on problem-solving often just burns them out, while putting them on growth areas multiplies their impact.

According to Gallup’s research on strengths, people who use their strengths every day are six times more likely to be engaged on the job. A good coaching practice helps leaders identify and leverage these strengths across their team.

The Social Contract

Every team operates under an unspoken set of rules. This is their social contract. It covers things like how you deliver bad news or what happens when someone disagrees.

Often, this contract is messy and undefined, which leads to conflict and erodes trust. You can fix this by having an open conversation. A certified executive coach can facilitate this process to re-engineer the social contract so everyone is clear on the rules of engagement.

For example, a team might agree: “I promise to tell you what I really think, even when it’s not easy.” This simple agreement can prevent festering issues. The International Coaching Federation emphasizes clear agreements as a foundation for productive relationships.

When a conflict does arise, you can go back to the contract. It creates a framework for healthy debate and keeps things from getting personal. A strong social contract is the foundation for building trust, making it safe for people to bring you bad news without fearing they’ll be shot as the messenger.

Conclusion

The journey of a leader is one of continuous change. What makes you successful at one stage of your career often becomes an obstacle at the next. Moving from a doer to a leader requires new skills, new language, and a new mindset.

Getting the right kind of executive leadership coaching can help you make these shifts. A strong training program or coaching program provides the outside perspective needed to see your blind spots. It challenges you to develop the humility to ask for help and gives you tools from an expert with deep coaching experience.

Ultimately, a successful coaching partnership gives you the tools to build a team that can thrive with or without you in the room. This is how you stop just being busy and start truly leading. It’s the path to becoming one of the senior leaders who makes a lasting impact on an organization.