First Leadership Gig: Dream or Batsh!t Crazy?

In this edition, we're looking at new leaders, the reality they face, the expectations we pile on, and whether the game has actually changed over the last 30 years.

Leaders on training wheels

Stepping into your first people leadership role is a big deal. So when I first became one, I didn’t want to stuff it up. I looked for role model leaders to help inspire and guide me. Short on inspiration I turned to TV.

Now I grew up with Captain Kirk, who didn’t exactly preach vulnerability or self-doubt. He always had a plan, his team was expected to follow his lead and, well, had no problem sacrificing a few redshirts along the way. Not exactly a blueprint for modern leadership.

Choosing a poor role model was just the start of many bad decisions to follow. But I learnt from them and found my own style.

And this got me thinking about first time leaders.

So I reached out to Rob, my Corporate Therapy podcast co-host and over drinks and complaints about bad backs, we pondered “what would it be like to be a fresh people leader today?”.

And boy did we have questions:

• Are today’s challenges new leaders face more intense, or are they just a different flavour of chaos?
• With the talent shortages have we lowered the bar on what we want from leaders?
• Are we setting our new leaders up to succeed, or for an ambush?
• What can new leaders do to get a rock’n start.

Let’s talk about it.

What’s changed in the world of leading?

Almost 30 years ago Rob and I got our first people leadership gigs. Were either of us ready for it? Hell no, yet I doubt many new leaders of today are any better prepared.

So we did a quick and dirty comparison to get a feel of what has changed (or not) in the business world leaders operate in.

Funny thing is, when we look back, it didn’t actually feel slower. The challenges didn’t seem any smaller, either. Sure, the world wasn’t buzzing with 24/7 notifications, but stress and deadlines? Oh, they were alive and well.

Maybe that’s the thing. Each era comes with its own brand of chaos, and as humans we adapt to the challenges of our times. What felt intense back then was just… different. And today’s leaders? They’re just dealing with a new flavour of batsh!t crazy.

What kind of leaders are we after?

We were curious though, what kind of leaders are we looking for these days. However after a fair bit of googling, reading and chatting to folks, we’re no longer curious, we’re terrified. We don’t want leaders we want unstoppable #%$! unicorns:

1. Adaptable

Covid didn’t just change the office—it turned leadership into a high-speed obstacle course. Now, a real leader is expected to:

• Treat disruption like it’s an ‘opportunity‘. I say it’s still a turd, just rolled in glitter
• Make lightning-fast pivots ‘in the moment’
• Own experimentation and embrace the "fail fast, learn faster" mantra
• Build resilience in themselves and their teams because the rollercoaster isn’t slowing down

This drive for adaptability isn’t just a trend; it’s survival. With tech changing at warp speed and global events as unpredictable as ever, flexibility is no longer optional.

2. Empathetic

Leadership used to be all command and control, and do as I say, not how I do. These days your expected to have a soul and we want leaders who:

• Actually listen when their team talks
• Create trust-filled environments where ideas can breathe
• Foster a sense of belonging where every voice counts
• Celebrate the small wins that keep people motivated

This pivot to empathy-first leadership recognises a big truth: giving a damn about your team, means folks are more likely to care about the business.

3. Tech-Savvy

With tech moving faster than Usain bolt, leaders today need to know their way around not just the digital landscape, but this thing called AI. Here’s what that looks like:

• Keeping an eye on emerging tech, ready to pounce on the next game-changer
• Building a culture where innovation and learning are par for the course
• Leveraging data to steer strategy and make informed calls
• Harnessing tech to unlock new levels of productivity.

4. Purpose-Driven

In a world asking, “What do you stand for?” leaders are stepping up with purpose and integrity. The mission? To lead with meaning and do it right:

• Craft and share a vision that actually resonates
• Align the business with social and environmental good.
• Be a champion for diversity, equity, and inclusion—no lip service here
• Make decisions that aren’t just good for today but build a better tomorrow

We say we want this but do we really? Because I’m sure as hell not seeing this at the board level?

5. Hybrid Skills

With remote and hybrid work now a thing, leading a team isn’t confined to the office walls. A modern leader in the remote era will:

• Command virtual tools like a pro, making online feel as connected as in-person
• Keep the team vibe alive, no matter the time zone
• Respect work-life boundaries, because burning out your team doesn’t lead to breakthroughs
• Ensure that remote and office-based teammates get the same shot at success

In short today’s leaders need to wired for adaptability, empathy, tech savvy, purpose, and a whole new playbook for leading from afar. Holy crap, and we wonder why we are struggling to find these folks.

It also doesn't help we keep looking in the same places, with woman and leaders of colour remaining underrepresented in first management positions and beyond. I encourage you to read McKinseys Woman in the Workplace 2024 report

How can organisations support their new people leaders to succeed?

For organisations looking to help new leaders find their feet, here are some practical go to steps:

1. Structured Onboarding Programs: Forget the sink-or-swim method. Give new leaders the floaties they need—a solid onboarding program that covers the technical side and the human side of leadership.
2. Mentorship Opportunities: Pair them up with a mentor of someone who is just ahead of where they are at. This means you will need to be on the constant look out for mentors in your business.
3. Regular Check-ins: Check in. And not the "how's it going?" while-walking-away kind. Real, meaningful check-ins to see how they're doing, what they’re struggling with, and where they need a hand.
4. Leadership Training: Hit them with training that matters. Not the ‘death by PowerPoint’ kind. Were talking conflict resolution, communication skills, and empathy. The kind of skills they'll need when the office turns into a soap opera.
5. Create a Support Network: Encourage them to build a network of fellow newbies. A place where they can say, "I have no idea what I'm doing," and hear, "Oh thank God, me neither." It's like group therapy but with fewer couches.
6. Clear Expectations: Ambiguity is the confidence killer. Be clear about what success looks like. No mixed signals. No guessing games. Just straight-up guidance on what you expect.
7. Psychological Safety: Make it safe for them to screw up. Because guess what? They will. But every failure is a step closer to getting it right. If they're too scared to fail, they’ll never take the risks needed to grow.
8. Celebrate Small Wins: This doesn’t have to be a full blown parade, but recognise those little wins as they matter. Think back on the moments of encouragement you got, I’m sure they mean far more to you than perhaps the leader who gave them ever realised.

Getting a Solid Start: Your Playbook

If you’re stepping into your first leadership gig. Congrats here’s what we recommend you focus on:

• Build Relationships, Not Control: Get to know your people. Like, really know them. The faster you build trust, the easier everything gets.
• Be Comfortable Being Uncomfortable: Leadership is a giant unknown, so if you’re waiting for clarity, you’ll be waiting forever.
• Find Your Guiding Principles: What do you stand for? Authenticity and consistency are non-negotiables. This can take time to discover as you make decisions.
• Listen More Than You Talk: You’ll never know everything, but your team knows a lot—use that to your advantage. Unlike Captain Kirk modern leaders of today don’t need to know the answers, they need to know their team who have the answers.
• Seek Feedback Early and Often: It’s not a weakness; it’s how you grow.

Thats A Wrap

Leading people in 2024 isn’t about knowing all the answers. It’s about asking the right questions, embracing the learning curve, and being okay with the messiness of it all.

The best leaders today aren’t the ones who have it all figured out; they’re the ones who are willing to grow alongside their teams.

Let’s keep redefining what leadership looks like one real conversation at a time.