In this post, I share my biggest takeaways from my conversation with leadership coach Kelly Stuart on the Lead Smarter podcast. Use the links below to jump to any section:

• Why good individual contributors struggle as leaders

• The entrepreneurial "cheat code" and its trap

• Why middle managers are the most overlooked leaders

• Leading when you do not know the work

• Working with "old-school" leaders

• Curiosity: the most underrated leadership skill

• Books Kelly recommends for leaders

• Bringing this back to your own leadership

Most people do not step into leadership because they were coached, prepared, and ready. They step in because they were really good at the thing.

That pattern shows up in almost every company I talk to: top performers get promoted, then suddenly they are supposed to manage people, influence culture, and think strategically - all with zero actual leadership training.

On a recent episode of Lead Smarter, I sat down with leadership coach Kelly Stuart, Owner at Conversations Worth Having, who has spent more than two decades helping people navigate that exact gap between being good at the work and being good at leading.

We covered a lot: why the traditional path to leadership is problematic, how entrepreneurs both benefit from and get trapped by their own vision, why middle managers quietly carry more weight than they are given credit for, and why curiosity might be the most underrated leadership skill you can develop.

This post walks through the biggest ideas from that conversation and how you can apply them in your own leadership, whether you are a founder, a new manager, or someone suddenly responsible for a bigger team.

Why good individual contributors struggle as leaders

Kelly and I started with a simple but uncomfortable truth: the way many organizations pick their leaders sets those leaders up for a rough time.

Most leadership promotions are based on performance in an individual contributor role. You are the best salesperson, the most reliable project manager, the engineer who ships the most features, so you get promoted.

The problem Kelly sees again and again is that the skills that make someone an excellent individual contributor are not the same skills that make someone an effective leader.

As she framed it in our conversation, leading well requires a shift from:

• Doing the work yourself to creating the conditions for others to do their best work

• Measuring your value by your own output to measuring it by your team's success

• Controlling outcomes directly to influencing outcomes through people, systems, and culture

When that shift does not happen, you get patterns that probably look familiar:

• New managers who keep stepping in to "fix" things instead of coaching their team

• Micromanagement masked as "high standards"

• Burnout, because the leader is trying to hold on to their old job and do the new one at the same time

Kelly talked about how critical it is for new leaders to recognize that leadership is a different job, not just a more advanced version of their old one. That mindset shift alone can change how they approach their days.

Instead of asking, "How much did I personally get done today?" the better question becomes, "How much did I enable my team to get done today?"

The entrepreneurial "cheat code" and its trap

Entrepreneurs, in Kelly's experience, have a kind of "cheat code" when it comes to leadership: they usually have a deep, intuitive understanding of the vision.

They know where they want to take the business, what they want it to stand for, and what "good" looks like because, in a lot of cases, they built it from the ground up.

That clarity is an asset. It is easier to make decisions when you have a strong internal compass. It is easier to set direction when you have lived every piece of the journey.

But there is a trap that Kelly sees founders and entrepreneurs fall into: they can assume that because the vision is clear to them, it must be clear to everyone else.

In reality, the people they bring in later do not have the same context, history, or emotional connection to the business. They see a job, a set of responsibilities, and maybe a few high-level goals, but not the full picture swirling around in the founder's head.

That gap can show up as:

• Frustration when team members "do not get it" or make decisions that do not align with the founder's mental model

• Difficulty delegating important work because the founder does not fully trust others to carry the vision forward

• Over-reliance on the founder as the decision-making bottleneck

Kelly talked about how one of the most valuable shifts for entrepreneurs is moving from assuming alignment to actively creating it. That looks less like "I told them what we are doing once" and more like ongoing conversations about why the work matters and how each role connects to the bigger picture.

This is where curiosity also starts to show up as a leadership skill: instead of assuming your team understands the vision, you ask questions to uncover what they see, what they assume, and where the gaps are.

Why middle managers are the most overlooked leaders

One part of the conversation that I think a lot of leaders will recognize is Kelly's focus on middle managers.

On paper, they are just another layer in the org chart. In practice, they are often the people holding everything together in the middle.

Kelly pointed out that middle managers have a uniquely challenging seat:

• They are responsible for delivering results through their teams

• They are expected to translate leadership's strategy into day-to-day reality

• They are the ones fielding feedback and frustration from both above and below

She described them as the layer that influences up, down, and sideways. A strong middle manager can connect teams, smooth out communication breakdowns, and highlight risks and opportunities that executives may not see from a distance.

Yet, as Kelly sees in a lot of organizations, they are often the least supported when it comes to leadership development.

They are given goals, dashboards, and deadlines, but not always the coaching and tools they need to handle the people side of the work: conflict, motivation, performance conversations, and change management.

When middle managers are underdeveloped, the whole organization feels it. Strategies do not land the way executives expect, teams feel disconnected, and issues get stuck instead of escalated and resolved.

Investing in this group - with training, coaching, and clear expectations about their role as leaders, not just administrators - is one of the biggest leverage points Kelly sees for improving organizational alignment.

Leading when you do not know the work

One of the most interesting parts of our conversation was Kelly's own experience leading teams where she did not fully understand the technical details of the work.

For a lot of new leaders, that situation can feel like a weakness. You cannot jump in and "do it yourself," so you might feel like you have less credibility or control.

Kelly had a different take. In her case, not knowing the work forced her into healthier leadership behaviors: she had to ask more questions, listen more carefully, and rely on her team to be the experts in their own domains.

Instead of leading by expertise, she led by curiosity and empowerment.

She shared how that approach helped her:

• Build trust with her team by showing she valued their knowledge

• Encourage ownership, because people were not waiting for her to swoop in with the answers

• Avoid micromanaging tasks she did not fully understand anyway

For leaders who feel like they need to know every detail before they can lead effectively, Kelly's story is a useful counterpoint. There are real advantages to being the person who asks good questions instead of the person who has all the answers.

It does not mean you abdicate responsibility. It means you focus on setting clear outcomes, creating psychological safety, and helping your team remove roadblocks, instead of trying to be the most technically skilled person in the room.

Working with "old-school" leaders

Kelly has coached a lot of leaders who came up in more traditional, top-down environments. The kind where authority flows one way, decisions are centralized, and leaders are expected to direct rather than collaborate.

Those leaders are often not trying to be difficult; they are applying the playbook that worked for them earlier in their careers. The challenge is that the expectations of employees today, and the complexity of modern organizations, look very different.

In our discussion, Kelly walked through how she approaches working with these "old-school" leaders.

Instead of confronting them head-on with "You are doing it wrong," she focuses on small, practical shifts that create visible wins. That might look like experimenting with a new way of running meetings, trying a different approach to feedback, or involving their team in a decision where they would normally decide alone.

Once those changes start to show positive results, those leaders become more open to exploring different ways of leading.

Kelly emphasized the importance of using objective examples and outcomes in these conversations, rather than abstract theory. If a leader can see that a small change leads to better engagement or smoother execution, they are more likely to keep going.

She also highlighted the need for patience. Deeply ingrained leadership habits, especially ones that were rewarded for years, do not shift overnight. Coaching in those situations often means walking alongside someone through a series of incremental adjustments rather than trying to trigger a single big transformation.

Curiosity: the most underrated leadership skill

If there was one theme that kept resurfacing during my conversation with Kelly, it was curiosity.

We often talk about strategic thinking, communication, or decisiveness as core leadership traits. Kelly argued that curiosity sits underneath all of those.

When leaders are not curious, they fill in the gaps with assumptions: what they think their team is feeling, why they believe someone is underperforming, what they imagine a client wants.

Curiosity interrupts that pattern. Instead of assuming, you ask.

In practical terms, that can look like:

• Asking, "What do you need from me to be successful here?" instead of guessing what support your team wants

• Asking, "How do you see this situation?" before jumping in with your solution

• Asking, "What am I missing?" when a project is not moving the way you expected

Kelly connected curiosity directly to trust. When people feel like you are genuinely interested in their perspective, they are more willing to share what is really going on, not just what they think you want to hear.

That kind of honest information flow is critical for good decision-making, especially in fast-moving environments where leaders cannot see everything themselves.

Curiosity also helps leaders manage their own reactions. Instead of immediately labeling a behavior as "lazy" or "disengaged," you can ask questions and often uncover obstacles, misunderstandings, or misaligned expectations that are actually solvable.

Books Kelly recommends for leaders

Later in the episode, I asked Kelly about the books she finds herself recommending most often to leaders she works with.

She shared a few that have had a real impact on how people think about their leadership:

• Strengths Based Leadership - a book that encourages leaders to lean into strengths rather than obsessing over fixing every weakness

• Start With Why - which helps leaders articulate and communicate the deeper purpose behind their work

• How to Win Friends and Influence People - a classic that she has read multiple times and still finds relevant for building relationships and influence

These are not theoretical picks for her. They are books she returns to and points her clients toward because they offer practical shifts in how you relate to yourself and others as a leader.

Bringing this back to your own leadership

Conversations like the one I had with Kelly are a good reminder that leadership is less about having a certain title and more about how you show up day to day.

If you recognize yourself in any of the patterns we talked about - promoted because you were good at the job, feeling stuck between old-school norms and new expectations, or struggling to translate your vision into clear direction - you are not alone.

A few questions you might sit with after reflecting on Kelly's perspective:

• Where am I still trying to be the best "doer" instead of the best leader for my team?

• What assumptions am I making about what my team understands about our vision, goals, or priorities?

• How often do I ask curious questions before giving direction or feedback?

• Which middle managers in my world are carrying a lot of weight without much support, and what could I do differently there?

Leadership is not a one-time promotion; it is an ongoing practice. Kelly's work, and the stories she shared on the podcast, underline how much room there is for growth when we treat it that way.

If you want to go deeper on any of these topics, I would encourage you to listen to the full episode with Kelly and sit with which parts hit closest to home. That is usually where the most useful work starts.