You wouldn’t run your laptop for a year without updates. You’d get slower performance, security vulnerabilities, and eventually something would crash at the worst possible moment. Yet many leaders operate on the same mental models, habits, and approaches year after year, wondering why they’re getting diminishing returns.

So how do you know when it’s time for an upgrade? And what needs your attention most?

Think of this as your annual system check — a way to step back and assess what’s working in your leadership, what’s starting to show cracks, and where you need to develop next. I typically recommend leaders do this process near the beginning or end of the year, when you naturally have a bit more space for reflection. But honestly, any time you find yourself feeling stuck, overwhelmed, or like you’re running harder just to stay in place, that’s your signal.

1. Run Your Attention Audit

Start with the most fundamental question: where is your time actually going versus where it should be going?

Pull up your calendar for the last month. Don’t rely on memory here — actually look at where you spent your hours. What percentage went to strategic work? To developing your team? To managing crises that someone else should have handled? To meetings that added little value?

Now ask yourself: what am I still doing that someone else should own? This is where leaders often get stuck. You were promoted because you were excellent at certain things, and it feels risky to hand them off. But if you’re spending significant time on work that’s below your pay grade, you’re not just wasting your potential — you’re also blocking someone else from growing into that responsibility.

Here’s the flip side: what strategic work keeps getting pushed aside? The project that would actually move the needle, the relationship you need to build with a key stakeholder, the time to think through that org design challenge — if these keep landing on next week’s to-do list, something in your system needs to change.

2. Can your Team do More?

Here’s something leaders often miss in this audit: what resources and talent do you already have that you’re underutilizing?

I see this all the time in coaching conversations. A leader is convinced they need to hire someone new or outsource a project, when they actually have someone on their team who’s been waiting for exactly this kind of opportunity. Maybe you have a team member with financial modeling skills you didn’t know about. Or someone who’s expressed interest in taking on more strategic work but keeps getting assigned tactical execution.

Take a hard look: who on your team has capabilities you’re not fully leveraging? Are you defaulting to the same two or three people for everything instead of developing the full bench? Have team members shared strengths or interests that you haven’t activated yet? This isn’t just about delegation — it’s about seeing the full capacity already available to you.

3. How Well Are You Leveraging Your Unique Strengths?

Here’s where most leadership development goes wrong. It focuses on fixing weaknesses instead of amplifying what makes you exceptional.

A strength isn’t just something you’re good at. It’s an activity where you’re naturally talented AND it energizes you. This is where you create disproportionate value. This is your point of unique brilliance that will set you apart. Our strengths are so innate to us that we tend to take them for granted.

So what work makes you lose track of time? What conversations leave you energized rather than drained? What challenges do people specifically come to you for?

Now the hard question: how much of your week is actually spent in those areas? If it’s less than 30%, your operating system needs a major upgrade.

Most leaders spend their time shoring up weaknesses or doing work that someone else could do adequately. Meanwhile, the work that only they can do at a truly exceptional level — the work that leverages their unique combination of talents and energy — gets squeezed into the margins.

What if you flipped that? What if you organized your role, your team, and your calendar around maximizing time in your strengths? You’d deliver more impact with less effort. You’d develop faster because you’re working in areas where you have natural aptitude. And you’d stop burning out trying to be mediocre at everything.

4. What’s Your Next Area of Learning: Assess Your Skill Gaps

Here’s the question that makes leaders uncomfortable: what capability do you need next that you don’t have today?

Notice I’m not asking what you’re bad at. I’m asking what the next level demands of you that you haven’t had to do much of before. Because here’s what I’ve learned from working with hundreds of executives: the skills that made you effective at your current level are rarely the same skills that will make you effective at the next level.

When you moved from individual contributor to manager, you had to learn to work through others. When you moved from manager to director, you had to learn to think in systems and solve problems you couldn’t personally touch. Moving from director to VP often demands a shift to influencing without authority and thinking in longer time horizons. And moving into the C-suite typically requires a completely different relationship with ambiguity and organizational politics.

Here’s the thing: you can’t fix everything at once. And honestly, you shouldn’t try. So given everything you’ve learned in this audit, what’s the one area where development would be most leveraged?

Not what you’re worst at. Not what your boss mentioned in passing six months ago. What development would unlock the most value for you and your team right now?

Maybe it’s

– finally learning to delegate at a higher level so you can step out of the tactical work.

– developing your executive presence so you’re more influential in the C-suite.

– building deeper strategic thinking capabilities so you can shape direction instead of just execute on it.

– getting better at navigating organizational politics so you can get things done more effectively.

Pick one. Get clear on what success looks like. And then figure out how you’re going to develop it — whether that’s through coaching, a specific project that stretches you, regular practice, or learning from someone who’s excellent at it.

So what does your next level require? And where are the gaps?

One way to figure this out: look at the leaders you admire who are one level above you. What do they do that you don’t do much of yet? What conversations are they part of that you’re not? What decisions do they make that stretch you?

Another approach: think about the last time you really struggled or felt out of your depth. What was missing? Technical knowledge? A certain type of stakeholder management? The ability to make decisions with incomplete information? That struggle is data about what you need to develop.

5. Take a Relationship Inventory

Leadership doesn’t happen in a vacuum. It happens through relationships. So who are you investing in, learning from, and possibly neglecting?

Start with your stakeholders. Who needs more of your attention? I’m not talking about the squeaky wheels who already get plenty of your time. I’m talking about the key leaders whose support you need but haven’t cultivated, or the peer relationship that’s cooled and is starting to cost you.

Then look at your team. Who needs more of you right now? And just as important — who needs less? Sometimes the most generous thing you can do for a high-performing team member is to get out of their way. Are you over-managing someone who’s ready for more autonomy? Or under-supporting someone who’s struggling but hasn’t asked for help?

Don’t skip this part: who are you learning from? Do you have mentors, coaches, or peers who challenge your thinking? Or have you gotten so busy that you’ve stopped investing in your own growth and perspective? The leaders I see stagnate are often the ones who stopped being curious and stopped surrounding themselves with people who push them.

6. Check Your Energy and Sustainability

Here’s what no one tells you about leadership: it’s a long game. And if your operating system is burning you out, it doesn’t matter how effective you are in the short term.

What’s draining you? And I don’t mean “what’s hard” — leadership is supposed to be hard. I mean what’s taking your energy without adding value? The report you write that no one reads. The meeting that should be an email. The decision-making process that involves too many people and moves too slowly. The relationship that’s become toxic.

What’s energizing you? What work makes you lose track of time? What conversations leave you feeling more alive and creative? These aren’t just nice-to-haves — they’re signals about where you create the most value and where you should be spending more time.

And here’s where I often have leaders do a “More/Less” exercise: What do you want to do more of in the coming year? What do you want to do less of? Don’t be vague here. “More strategic thinking” isn’t actionable. “More time actually drafting the three-year vision” is. “Less time in meetings” isn’t helpful. “Less time in weekly status meetings that could be async updates” gives you something to work with.

The Point of All This

Look, you’re not going score 100% on this audit. And you’re not going to fix everything that’s broken. But if you invest even a few hours in this process, you’ll get clarity on what deserves your attention and what doesn’t. You’ll stop running the same plays that aren’t working anymore. And you’ll start developing the capabilities that will actually serve you at your next level.

Your leadership operating system deserves the same kind of maintenance you give your technology. Because unlike your laptop, you can’t just buy a new one when this version stops working. Thanks for reading.