#72: The Inside-Out Leadership Part 1

The shadow side of leadership (and no, it's not bad)

If I had one wish for all of my clients stepping into their first leadership roles, it’s this:

I wish someone had handed them a manual on what being a leader actually means, before they said, “Yeah! Let’s do this!” 😂

More often than not, people who get promoted to leadership aren’t ready… but through no fault of their own. The jump from IC to first-time manager is abrupt. Some get lucky and have great managers who guide them through it. But most don’t.

Their title changes on Workday, their boss announces it in an all-hands, and off they go… trying to lead while also trying to look like they already know how (because nobody can know they feel like a headless chicken).

The role can be incredibly fun and fulfilling. But it can also be an express lane to burnout-ville if you’re not careful.

There’s plenty of talk about what good leaders should or shouldn’t do.

But not many people talk about how:

1. You can be a great manager, hire only A players/rockstars/whatever the term of this era of the industry is, and never miss 1:1s, and still end the day feeling drained as hell?

2. You can learn all the frameworks, run the sessions/workshops, and create decks that get passed around the company, but people are still giving you feedback left and righ,t saying you’re not being strategic.

3. You can follow all the best practices, do the “good” stuff, and stop doing the “bad” stuff and still feel like you’re doing it all wrong.

And that feeling: of not knowing what you’re doing wrong, of second-guessing your every word, of ending the day joyless and tense — that’s actually where all the problems start

Ok ok, now that we have that clear... What does that mean?

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Optimizing for the visible side of leadership

The stuff people can see is what gets measured. So of course, we focus on it first.

It’s what gets recognized and eventually rewarded (because it’s what’s included in the Job Description). So it’s also what stakeholders and senior leadership watch out for to evaluate.

I’ve once talked about the 3 overlapping hats that leaders need to wear at any given time. There’s just so much to do. And for new leaders, all of it is new.

So naturally, we optimize what we can see. A bit hard to work on something you’re not even sure was there in the first place, right?

But not working on the shadow side makes for a weak leadership foundation. And eventually, cracks will start to show. Not always in one fell swoop, but slowly like having a hang nail that’s not so bad, but you can’t help but pick on it until the mild annoyance becomes a bleeding mess.

The impact of an underdeveloped shadow side is not always seen immediately. But they compound. Because most of the challenging moments are not just about the tasks alone — they’re also about how we respond under pressure, how we protect our energy, and how we manage our stories about ourselves:

• There’s always a Slack message asking for 5 minutes

• When we keep softening feedback because we don’t want to offend anybody but that only enables bad behaviors to continue

• The 10th company-wide email about how you’re all a family and everybody’s contribution is important. That’s followed by a 30-minute secret call that’s asking all managers to evaluate who gets to stay or go because AI is taking over the world, obviously.

And unfortunately, no amount of re-reading Radical Candor, Leaders Eat Last, or Empowered can help ease the inner conflict.

So now what?

Is the new leader just not good enough or not working hard enough?

You already know the answer — of course not. It’s just that the tools that they’ve been handed are the ones that are not enough.

We try to match what’s in the JD because that’s what people notice and promote. But that version of leadership has a shelf life.

The visible parts of leadership do not replenish. It only demands. It demands that your back is straight and your answers are polished. So you always look like you’re on top of things.

And that’s when new leaders start realizing that the job isn’t just about creating strategies to execute, hiring A-players and rockstars, or negotiating with nearly everybody in the organization about the priorities. That’s just one half of it.

The other half is about having the strength in your knees to keep standing when the storm is at its peak (or maybe even walk away if that’s what’s needed). And that’s hard work too.

✍️ What's the biggest challenge you're facing right now as a leader? 

Feel free to share in the comments. The more people share, the more we realize we're not alone. ❤️

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The “shadow” side of leadership

Underneath the tangible side of leadership is the actual job. And the actual job is layered and deeply human.

Leadership is a constant negotiation between what the business needs, what the team needs, and what you need — and when those 3 are misaligned, the work becomes harder than it already is.

It’s not that people are hiding this part of the job. Most of us just never had it modeled.
We’re taught how to lead others, but rarely how to lead ourselves. And yet, those two sides are always in motion together.

Leading others is the visible side of the work: the skill-based work that you can learn from books, trainings, and copying what others are doing. Like managing a budget, writing a performance review, aligning on team goals, or figuring out who to hire next. It’s the part that fills your calendar and your to-do list. The part that gets evaluated and tracked. This part we know so well.

Leading yourself is the internal side: the shadow work of understanding your values, regulating your energy, recognizing your defaults. It’s asking why certain feedback hits a nerve. Why you avoid hard conversations. Why you keep second-guessing your own decisions. It's the part that enables the execution of the external side of leadership.

It’s the part most people skip because it wasn’t explicit in the JD. Fair! Because how do you write in the JD that your ideal leader should know their values to let them shape their decisions???

Leading yourself means noticing your defaults and being honest about whether they still serve you so you can decide when to hold your ground and when to adjust. It doesn't mean being 100% unshakeable (that requires shaolin training more than coaching). It’s about knowing what’s shaking you, and responding with intention instead of instinct.

And how does it look like when we don’t lead ourselves? This is when the internal patterns start leaking into the external execution:

• When we keep saying yes to every "do you have 5 minutes?” that we leave no time for the work we actually do, rendering all those tools and frameworks useless

• When we keep softening feedback because we don’t want to offend anybody, but that only enables bad behaviors to continue

• When we keep getting into spats with our stakeholders and senior leaders, simplify the situation as them being difficult because we also don’t want to back down.

These examples just go to show that the two sides aren’t separate. They flow with each other. Your internal patterns will always shape your external performance, whether you’re aware of them or not. And your external performance can influence your external patterns (whether that’s a good thing or a bad thing depends on you).

⛑️ If you're a new leader finding the day-to-day of your new leadership life challenging, I'd love to support you. I have a few slots open from September. 

🔗 Click here to book a discovery call with me and let’s chat about how I might be able to help you.

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Leading Yourself: Shedding light on the Shadow side of Leadership

There’s no such thing as perfect leadership. But when we know how to lead ourselves, putting in place the tools we have to lead others will come with less struggle or even less cost (especially to ourselves so we can keep going).

What does leading ourselves mean?

It starts with this: Noticing your internal patterns before they become the driver for your reactions.

How does one start with leading one’s self?

• Starting with curiosity. Examining the feelings and thoughts that come up, noticing when we’re reacting on autopilot, and asking ourselves where that reaction is coming from — and whether it still serves the kind of leader we’re trying to become.

  Examples: 
  
  1. Why are we feeling the pressure to have all the answers out right and why are we afraid to admit that maybe we don't know? 
  
  2. Why do we feel icky when we need to talk about the work we've done to more people? 
  
  3. Why is it that when we find something easy, it doesn't feel real? 

• Having awareness of what we already bring to the table. Most people are quick to identify what they’re lacking. And that’s great, personal development should be a life-long experience. But from my experience, people usually have a very hard time identifying their strengths and talents. And we’re quick to believe that progress and success should come with struggle. But what if it could come with ease, too? Leaning into our strengths can have a higher ROI than constantly trying to fill in our gaps.

• Embracing failure. Failure is inevitable. And that’s a good thing! It’s the gateway to learning, if we let it. If we set our egos aside and don’t see failure as a challenge to our identity. We might even enjoy the process.

And when things feel political or messy, it helps to pause before writing the whole situation off as toxic. Sometimes that’s true, but sometimes it’s just a mismatch of incentives, context, or trust that hasn’t been built yet.

There are moree and this is a much simplified version, but there are a lot of things to start with here already.

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Integrating the Inside and the Outside

So how does this all work together?

What do you actually do with this awareness of internal patterns, defaults, and shadow work — especially when you're still expected to show up, make decisions, and hit goals every week?

That’s where we’re headed next.

We’ll get into that next.

Part 2 is where we start connecting the dots between the internal work and the day-to-day stuff: meetings, decisions, tension, feedback, and all the messy human bits in between.

But for now, I’ll pause here before this turns into an ebook😂

If you’re not subscribed yet, this is your sign! So you don’t miss the next chapter of Integrating the Shadow 🌚

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TL;DR

Most new leaders get handed a role, not a roadmap. So they pour their energy into what’s visible because that’s what gets rewarded. But over time, that version of leadership starts to fray. Because no one told them the internal side matters just as much.

And when that internal foundation, your values, your patterns, your energy, is ignored, it starts leaking into how you lead. That’s when things get murky. You say yes too much. You soften when you should hold the line. You react instead of responding.

Leading others is half the job. The other half is learning how to lead yourself. And no, it doesn’t make it easier. But it does make it more sustainable.

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📌 Coaching Bulletin Board:

📌 I’m doing a 90-minute leadership reset for new leaders who are feeling bogged down while navigating the murky and messy life of being a middle manager. It’s a few weeks from now. Join me!

📌 1:1 Coaching for the new Product, UX, and Tech Leaders going through career dilemmas. If this is you, I’d love to help you define your strategies to set yourself and your team up for success. Book a free call and let’s discuss how we can work together.

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If you got to this part of this newsletter, thanks for staying with me until the end. And thank you for sharing with me topics that you’d like for me to share my thoughts, feelings, and violent reactions on.

💙
Kax