The Leader's Kitbag

In this episode of The Leaders Kit Bag, we’re tackling one of the biggest challenges even the most self-aware leaders face: uncovering blind spots. 

Using a personal story from the development of Ben AI, I share a real-life example of how a name that seemed perfectly logical on paper almost became a serious misstep, simply because the people around me didn’t feel comfortable enough to challenge it early on. 

We explore the real reason why valuable insights often go unspoken: a lack of psychological safety. 

This episode unpacks what psychological safety really means, why it’s so crucial to your team's effectiveness, and the key things we can do to accelerate it in new working relationships. 

You’ll learn: 

• Why even confident teams may hesitate to speak up 
• The two root causes of low psychological safety 
• How to reinforce open communication by praising the right behaviour 
• A simple strategy to accelerate trust-building in your team 

…all in just six minutes! 

Ben AI – Free Leadership Support, 24/7 

Leadership can be tough. But getting high-quality support shouldn’t be. 

That’s why I’ve made Ben AI—my personal AI-powered leadership coach—completely free for everyone to use. 

Whether you're facing a tricky conversation, trying to motivate your team, or simply need a confidence boost before a big presentation, Ben AI is here to help—any time, day or night. 

This isn’t just tech for tech’s sake. 

It’s part of my mission to create a world where everyone can go to work feeling inspired to give their best, and return home feeling recognised and appreciated. 

Try Ben AI for yourself – no sign-up, no charge 

In this powerful and refreshingly candid conversation, Ben Morton welcomes back Tessa Clarke, co-founder of Olio, to reflect on the scale-up phase of building one of the UK’s leading sharing economy apps. 

From their $43 million Series B raise to restructuring through a turbulent 2023, Tessa takes us inside the mindset shifts, leadership lessons, and cultural priorities that have defined Olio 3.0. 

For leaders navigating the messy middle between startup energy and operational maturity, this episode is a masterclass in clarity, courage, and culture-first decision-making. 

Why this episode matters: 

Scaling a business often comes with the risk of losing what made it special in the first place. Tessa shares how Olio kept its startup spirit alive, even while hiring a C-suite and overhauling internal systems, without letting bureaucracy creep in or values drift. 

What You’ll Learn: 

• How to evolve from "scrappy startup" to a mature organisation without killing agility. 
• The importance of ‘mission obsession’ in hiring, onboarding, and performance. 
• The surprising downside of hiring too many “brilliant” people too quickly. 
• Why founders shouldn’t always let go of product ownership, and how to decide. 
• How gender bias affects female founders during fundraising, and how Tessa navigated it. 

Ben’s Standout Moments: 

• Tessa’s “Uniquely Me” document—a weekly discipline to focus on what only she could do as CEO. 
• Her approach to maintaining trust and culture in a growing team. 
• The candid admission of being “too idealistic for too long”—and what changed her thinking. 

Want to Assess Your Own Leadership Readiness? 

You might have an open-door policy, but if a metaphorical grizzly bear is sitting behind it, your team still won’t walk through. 

In this episode of The Leaders Kit Bag, I dig into a leadership truth that’s hard to hear but vital to address: just because you’ve got an “open door policy” doesn’t mean people feel safe enough to share everything you need to know. 

I explore why feedback often goes unspoken and why well-meaning leaders may be making decisions based on partial truths and assumptions, without even realising it. 

In this episode, you’ll learn: 

• Why teams hold back the feedback you most need to hear 
• Three common reasons people don’t speak up 
• The truth about your leadership brand, and how to improve it 
• A powerful, practical formula to help build genuine trust and psychological safety 

This one is all about creating a culture where people feel safe enough to tell you what you need to hear, not just what you want to hear. 

Ben AI – Your Free Leadership Coach, Anytime You Need It 

As you’ve now realised, you might have an open-door policy, but if there’s a metaphorical grizzly bear sitting behind it, your team still won’t walk through. 

The truth is, people won’t share honest feedback if they don’t feel safe. That’s where Ben AI comes in. 

Ben AI is your personal, AI-powered leadership coach, designed to help you create psychological safety, lead with impact, and get the unfiltered insights you need to grow. 

And the best bit? It’s completely free. 

Because access to great leadership support shouldn’t depend on budget, it should be there for everyone, whenever they need it. 

• Ben Ai is built on years of real coaching experience 
• It’s available 24/7, ask anything, anytime 
• It’s totally free, no login, no sales funnel 

Try Ben AI today and take the bear out of the room! 

In these ‘SHORTS’ episodes of my podcast, I select my favourite moments from previous episodes. This one comes from episode 177, with innovation strategist Frank Mattes, where he addresses how to identify and build the kind of teams that don’t just execute, but innovate.

Once you’ve listened to the ‘SHORT’, why not click the link below and tune in to the full episode? 

Enjoyed The Short? 

In today’s episode, I offer a fresh perspective on one of the concepts I’ve shared time and time again: leadership is not about having all the answers. 

Using the metaphor of a lighthouse versus a radar, I explore the subtle but powerful shift in mindset that enables great leaders to navigate with agility, listen deeply, and respond wisely. 

Where the lighthouse stands still and broadcasts in one direction, the radar constantly scans, listens, and adjusts. 

That’s what today’s most effective leaders do: they ask more than they tell. 

In this short episode, you’ll learn: 

• Why strong leaders don’t need to have all the answers 
• The power of asking questions over giving instructions 
• How this mindset shift can unlock new insights, ideas, and engagement 
• A memorable “brain tattoo” to guide your everyday leadership 

Ben AI – Your Free Leadership Coach, Anytime You Need It 

Leadership doesn’t always happen between 9 and 5, and support shouldn’t either. 

That’s why I created Ben AI, and more importantly, why I’ve made it completely free to use. 

Ben AI is your on-demand leadership coach. It is built to offer practical, grounded advice whenever you need it, whether it’s a quick tip before a difficult conversation or guidance on how to motivate a struggling team member. 

It’s the result of years of coaching, real-world experience, and a deep belief that great leadership support should be accessible to everyone, not just those with big training budgets. 

• Ask questions, get personalised advice in seconds 
• Available 24/7, because leadership isn’t always a 9-5 job 
• No cost, no catch—just support when you need it