Steve McLeod has spent years building Feature Upvote, a small bootstrapped software company, and along the way became fixated on a question most product literature ignores: how do founders with no product manager, no big budget and no army of researchers actually decide what to build next? He set out to write a book about prioritization frameworks — and discovered almost nobody uses one. This episode is the story of what he found instead, drawn from interviews with ten small, self-funded software companies (including Squadify's own Dan Hammond and Pia Lee) about how they really make product calls under pressure.

The conversation lands on the "Hippo" — Highest Paid Person's Opinion — and the reassuring discovery that it's rarer than founders fear: the companies that lasted were the ones who brought their whole team into the decision, even when the founder ultimately had to call it. Steve walks through the recurring traps (chasing every early customer request until the product buckles under its own clutter), the founders who held their nerve on vision anyway, and the practical habit — ruthlessly deleting your backlog — that keeps decision-making sane as you scale.

Key Themes & Takeaways

• Most software is built by small, bootstrapped teams, yet almost all published advice on feature prioritization assumes you have VC funding and a dedicated product management function.
• In companies under roughly 30 people, a dedicated product manager rarely exists — the founder is the de facto product manager whether or not they were ever trained for the role.
• The feared "Hippo" (highest paid person's opinion) showed up far less than expected: the founders who survived were the ones who genuinely brought their team into the decision before calling it.
• Early customer flattery is dangerous — saying yes to every request in the early days can quietly bury a product in clutter, technical debt and UX debt until the simplicity customers loved disappears.
• Some founders held firm to a narrow product vision under customer pressure and it paid off (Balsamiq's low-fidelity-only stance); others drifted toward enterprise features and had to consciously claw back to their original audience.
• Saying no needs a companion habit: regularly deleting (or archiving) your backlog, since an ever-growing "maybe later" list becomes its own source of stress and false hope
• Co-founder decision-making works best with clear domain ownership and transparency about disagreement — naming the tension openly beats either person quietly overriding the other.

Three Reasons to Listen

• Listen if you're a founder secretly doing product management without ever having the job title for it — Steve makes the case that this isn't a phase to survive, it's exactly where you're supposed to be right now.
• Listen if your backlog has quietly become a graveyard of ideas you'll never build — there's a blunt, freeing argument here for deleting almost all of it.
• Listen if you and a co-founder (or any two people sharing decisions) keep circling the same disagreement — Dan and Pia's own way of working through this at Squadify gets picked apart in detail, including what they actually do when they don't agree.

Notable Quotes

Steve McLeod's Bio
Steve McLeod is the co-author of "Kill the HiPPO: How small, bootstrapped software companies decide what feature to build next". The book is a collection of interviews with founders of stable, mature, profitable software companies, telling real stories about how founders make hard product decisions.

Steve is a three-time bootstrapped founder and currently CEO of Feature Upvote, a SaaS platform for managing customer feedback.

After experiencing near burnout in his first company, Steve intentionally keeps his running of Feature Upvote low-stress, aiming for modest, manageable growth, so that he can keep mentally healthy while running it.

Originally from New Zealand, Steve has worked in Australia, Germany, the UK, Spain, and more briefly, in Switzerland and France. He now lives in Barcelona, Spain.

Links

• Kill the Hippo
• Feature Upvote

Ian Turner has spent over two decades as a Chief People Officer watching the same slow collision happen inside organisations: brilliant performers get promoted into leadership roles, never get developed as leaders, and quietly become — in Ian's phrase — "overpaid doers." This episode asks what it actually takes to be a human-centric business leader, why that capability is in shorter supply than it should be, and what the real commercial cost is when organisations let it drift.

The conversation lands on a deceptively simple idea: sustainable performance comes from leaders who hold the commercial and the human in the same hand at the same time — not alternating between them, but integrating both as a single discipline. Ian reframes what that looks like in practice, from getting out of your furrow in the carpet to understanding that every tech transformation is actually a people transformation with a tech element.

Key Themes & Takeaways

• Leaders who succeed long-term care passionately about two things simultaneously: delivering results and the people delivering them — treating these as one system, not a trade-off.
• Organisations have created a generation of "overpaid doers" — people promoted for technical excellence who were never equipped, trained, or expected to actually lead.
• The "furrow in the carpet" is a powerful diagnostic: if your daily movement through an organisation never changes, your leadership reach probably doesn't either.
• Attrition, stagnation, and cultural echo chambers are not people problems — they're the commercial consequences of ignoring the human side of performance.
• Post-COVID, companies that genuinely cared about their people maintained flexible, human-aware cultures; those that did it out of necessity are now facing the cultural bill.
• The most powerful thing a leader can offer isn't advice — it's belief. Coaching someone to their own solution builds both the answer and the person.
• Every tech transformation is a people transformation with a tech element — and leaders who frame it the other way around will keep hitting the same wall.

Three Reasons to Listen

Listen if your organisation keeps hitting numbers in the short term but quietly haemorrhaging your best people — Ian names exactly why, and it's not what most senior leaders want to hear.

Listen if you've ever caught yourself thinking that leadership is "on the side of the desk" — this conversation will reframe that as a strategic and commercial error, not just a personal development gap.

Listen if you're trying to make the case internally that human-centric leadership isn't soft — Ian builds the business argument clearly, without ever making it fluffy.

Notable Quotes

"They don't become leaders because they're recruited into those more senior roles because they've been a great salesperson, a great product person, a great marketer — and they've not been recruited because they show true leadership traits."
— Ian Turner

"Every transformation is a people transformation with a tech element. It's not a tech transformation with a people element."
— Ian Turner

"One of the most powerful things you can offer another person isn't advice — it's belief."
— Ian Turner (referencing Jenny Rogers, Coaching Skills)

Ian's bio
Ian Turner, a Chief People Officer, talent strategist and leadership coach with over two decades of experience shaping people and culture across some of the UK's most recognised organisations. From leading transformation programmes and building high-performing teams to championing social mobility and developing future talent, Ian has built a reputation for combining commercial acumen with a genuinely human approach to leadership. He's passionate about helping people realise their potential and creating workplaces where both individuals and organisations can thrive.

Episode Summary

Joel Casse spent over two decades inside large global organisations — most recently as Nokia's Global Head of Leadership Development — watching senior teams up close. What he found wasn't a talent problem. It was a behaviour problem: packed agendas with no room for the team itself, leaders competing to showcase expertise rather than build on each other, and decisions perpetually kicked offline.

The conversation explores why this happens — egos, function-first loyalty, a bias for action that keeps teams stuck above what Roger Harrison calls the "waterline" — and what actually shifts things. Joel's tool is the balcony move: stepping out of the discussion to name what he observes. One quiet observation ("I've counted eight 'let's take it offline' in 20 minutes") became a two-hour conversation about how that team made decisions. Slow to go fast.

Key Themes & Takeaways

• Most senior teams debate (I'm right, you're wrong) rather than dialogue (let's understand each other) — and almost never ask genuine questions
• The waterline model: teams focus on task and content; relationships and process stay hidden until something breaks
• The SPQA framework: Situation → Problem → Question → Answer. The mistake is jumping straight from problem to answer
• "Let's take it offline" is a red flag — it means the conditions for real decisions don't exist in the room
• Irritating behaviours go unchallenged because peers won't hold each other accountable and leaders see it as babysitting
• The balcony move — stepping back to name what you observe — is the most underused act in senior team leadership
• When senior leaders change, it trickles down: their direct reports start doing check-ins, calling out patterns, working the same way

Three Reasons to Listen

• Listen if your leadership team meetings feel busy but never quite land anywhere. Joel names exactly what's happening — and why the smartest people in the room are often the ones causing it.
• Listen if you've ever sat in a meeting counting how many times someone said "let's take it offline." There's a two-hour conversation hiding in that habit.
• Listen if you want one thing to do differently as a leader or coach. The balcony-and-dance move is simple, and Joel has watched it ripple from the C-suite all the way down.

Notable Quotes

"When a leader is doing 80% of the talking, there's a fair chance that the team isn't doing well. They're not learning." — Joel Casse

"Teams tend to be a collection of people — not necessarily having a common goal with interdependency and a common fate. If you fail, well, that's your problem." — Joel Casse

"Leadership is your main course. It hass become the side dish — or a tiny pot of condiment you don't even have to have." — Dan Hammond

Joel's bio

Joel Casse is an executive coach and leadership architect with over 20 years of experience developing leaders and teams in global, matrixed organisations. Based in Munich, he has spent the majority of his career at Nokia, where he coaches executive teams and directs high-potential programs. Before Nokia, he worked at Novartis. He has worked with CEOs, Presidents, and VPs and their leadership teams on topics ranging from succession discussions to strategic off-sites to cross-team collaborations. He has led company-wide leadership frameworks, overseen flagship executive programs, and guided multiple leaders to C-suite promotions. Joel also teaches at Duke CE and Emeritus Business School, delivering executive interventions for companies in retail, banking, insurance, and IT. He holds an ILM 7 Executive Coaching accreditation and co-authored the book “Leadership for a New World.”

🎧 Three reasons to listen

• Make feedback less scary and more useful – learn why most feedback triggers defensiveness and how to avoid it
• Get a practical framework you can use immediately – mindset, relationship, and delivery
• Handle difficult conversations with confidence – be honest and direct without damaging trust

Episode overview

In this episode, Dan and Pia are joined by Katie O’Brien Ceccarini, leadership coach and author of Fearless Feedback, to tackle one of the most challenging aspects of leadership: feedback.

They explore why feedback often creates fear and resistance—and how to reframe it as a constructive, human conversation.

Katie shares her Fearless Feedback framework, focusing on mindset, trust, and practical delivery, helping leaders move from awkward, avoided conversations to clear, confident, and growth-oriented dialogue.

Memorable moments

• “No, I’m not.” – Katie’s honest story of being labelled defensive (while feeling embarrassed internally)
• The finding that 90% of people don’t want to hear “Can I give you feedback?”
• The “food in your teeth” analogy for why feedback should be timely
• A powerful reframe: “Feedback without action is criticism.”
• The shift from analysing the past to co-creating what happens next

Practical takeaways

• Start with mindset:
  Go in believing you are helping the person succeed
• Ditch the word “feedback” in the opener:
  Lead with what’s in it for them
• Use the three-part framework:
  • Mindset → why you’re saying it
  • Relationship → trust and safety
  • Delivery → clarity and structure
• Make it a conversation, not a monologue:
  Ask questions and co-create next steps
• Focus forward:
  Spend less time analysing what went wrong, more time on what to do next
• Create accountability:
  Agree follow-ups and shared responsibility
• Act quickly:
  Don’t wait—feedback loses value when delayed

Katie's’s media recommendation

• 📖 Still Human: How to Build Organizations Where Leaders and Teams Thrive with AI
  A timely exploration of how to maintain humanity, connection, and leadership impact in an AI-driven world

Bio
Katie O'Brien Ceccarini is the Founder of Endurance Management Coaching, a Certified Executive Coach, and author of Fearless Feedback: Everything Managers Have Never Been Taught About Feedback.

At 22, she began managing her first team with no handbook, no roadmap — just botched conversations and stretched-thin moments every leader knows too well. That experience is exactly why she wrote this book: not to give theory, but to give managers what actually works.

Over 20 years, she's managed, trained, and developed thousands of people — from scaling Customer Success at Yelp to leading Learning & Development at Opendoor. She's taught her Fearless Feedback Mastery course on Maven since 2022, earning a 4.8 out of 5 rating.

Today she works with organizations like eBay, LinkedIn, and AllState to build high-performing teams with the power of feedback.

Links

• Fearless Feedback
• Still human

🎧 Three reasons to listen

1. Rethink performance problems – Learn why most performance issues aren’t people problems at all, but symptoms of unclear systems, roles, and ways of working.
2. Lead for impact, not burnout – Discover how leaders unintentionally drive burnout by asking individuals to compensate for broken systems—and what to do instead.
3. Practical ways to create momentum – Take away simple, team‑level actions that improve clarity, decision‑making, and execution without needing enterprise‑wide change.

Episode overview

In this episode, Pia and Dan are joined in person by Squad coach Brooke Lewis to challenge one of the most common assumptions in organisations: that underperformance means someone needs fixing.

Drawing on Brooke’s experience in organisational development, the conversation explores how organisations often default to coaching individuals, running workshops, or “upskilling” leaders—while overlooking the system those people are working within. From unclear decision rights and complex matrices to ineffective meetings and post‑Covid ways of working, the episode reframes leadership as creating the conditions for performance, not simply demanding more effort.

This is a practical, grounded discussion for leaders who want to improve performance without pushing their people towards burnout.

Key themes & insights

• Why organisations instinctively blame individuals instead of examining systems
• The three layers of performance: system, team, individual
• How invisible architecture (strategy clarity, roles, decision rights, rhythms) shapes behaviour
• Why leaders end up compensating for broken systems—and the cost of that
• The limits of individual development in poorly designed environments
• How teams can regain agency by improving their own ways of working
• Meetings as a powerful (and often overlooked) leverage point

Memorable moments

• “When the system lacks clarity, people compensate with effort—and effort without clarity leads to burnout.”
• “Great performance should be easier, not harder.”
• “Leadership is creating the conditions for other people’s success.”

Practical takeaways

• Before investing in coaching or training, ask: What in our system is making performance harder than it needs to be?
• Zoom out one level when diagnosing issues—look first at clarity, structure, and ways of working.
• Start at team level: improve meeting purpose, decision flow, and operating rhythms to build momentum.
• Assume positive intent and competence; if people are struggling, the environment is usually the issue.

Brooke’s media recommendation

Shrinking (Apple TV+) - a smart, witty series starring Harrison Ford that explores ageing, relationships, therapy, and humour—with surprising depth.

About the guest

Brooke Lewis is a qualified coach and experienced executive with more than 20 years in organizational development and leadership across industries including technology, financial services, manufacturing, and non-profit. Throughout her career, she has been most energized by helping people grow — coaching, mentoring, and creating the conditions for others to thrive.

An in-demand certified SquadifyPro team coach, Brooke works with leaders and teams to unlock their potential, elevate performance, and lead with authenticity and impact. She believes true leadership isn’t about titles or hierarchy — it’s about creating the conditions for others to thrive and building environments where people and business succeed together.

In an increasingly complex, polarised, and fast‑moving world, the ability to have high‑quality conversations may be one of the most important leadership skills we have.

In this episode of We Not Me, Dan Hammond and Pia Lee are joined by Dianna Anderson, founding member of the International Coaching Federation and a pioneer of coaching-based leadership. Together, they explore why conversations are the hidden engine of change — and how curiosity, presence, and shared language can help teams and societies move forward together.

Dianna introduces her framework “Untying the Knot”, offering a practical way to understand what really blocks progress in conversations — and how to shift from argument and polarity to connection, trust, and hope.

🎯 Three Reasons to Listen

1. Learn a simple framework for navigating difficult conversations
   Diana’s Untying the Knot model helps you quickly identify what’s really getting in the way — whether it’s awareness, fear, or skills.
2. Build confidence to engage across difference
   Discover how to stay grounded, curious, and connected — even when values, worldviews, or emotions run high.
3. Reconnect with hope in a complex world
   This episode reframes today’s uncertainty not as collapse, but as fertile ground for meaningful change — starting with how we talk to one another.

✨ Episode Highlights

• Why change today is fundamentally different — and why linear conversations no longer work
• How our worldviews shape every interaction (often without us realising)
• The three types of “knots” that block progress in teams and relationships
• Why curiosity is more powerful than persuasion
• How to regulate yourself before entering high‑stakes conversations
• The link between psychological safety, leadership, and behavioural change
• Why hope is not naïve — but a leadership choice
• How better questions can completely transform everyday conversations

🔓 The Three Knots That Block Change

Diana explains that when conversations stall, there’s always a knot — and it’s usually one of these:

• Do‑Not‑See Knots
  Someone isn’t aware of a possibility, assumption, or perspective.
• Do‑Not‑Want Knots
  Fear, risk, or emotional resistance is holding someone back.
• Do‑Not‑Know Knots
  A genuine skills or capability gap is creating friction.

Identifying the right knot helps focus the conversation where change can actually happen.

💡 Practical Takeaways

• Enter conversations with curiosity, not certainty
• Ask open questions like “How does this make sense to you?”
• Don’t aim to win — aim to understand
• Regulate yourself before engaging others
• Start small: connection is success

📚 Recommended by Dianna

📖 Maybe You Should Talk to Someone — Lori Gottlieb
A warm, thoughtful exploration of different human worldviews through the lens of therapy — and a powerful way to build empathy and curiosity.

🔗 Links Mentioned

• We Not Me podcast:
  👉 https://www.squadify.net
• Squadify (podcast supporter):
  👉 https://www.squadify.net
• Book recommendation:
  Maybe You Should Talk to Someone by Lori Gottlieb
  (Available via major book retailers and libraries)
• International Coaching Federation (ICF):
  👉 https://coachingfederation.org

🎙 About the Guest

Dianna Anderson is a founding member of the International Coaching Federation and a global thought leader in coaching-based leadership and change. With over 30 years of experience, she helps leaders and organisations build shared language for navigating the human side of complexity, transformation, and collaboration.

In this episode, Dan and Pia are joined by Danielle DeMarco and Greg Neufeld to explore a powerful idea: the family is the first and most important team we ever belong to. Drawing on their backgrounds in venture capital, startups, and leadership, Danielle and Greg share how they intentionally design family culture using the same principles that underpin high‑performing teams — clarity, shared identity, rituals, and psychological safety.

The conversation spans family values, collective purpose, rites of passage, co‑leadership, and why modern parenting often creates more anxiety than clarity. Along the way, the group surfaces lessons that apply not just at home, but directly to enterprise teams, co‑leaders, and organisations navigating complexity.

Three Reasons to Listen

1. Reframe family as a team — not a series of individuals
   Learn how shared identity, collective incentives, and simple rituals can dramatically strengthen connection and reduce fragmentation at home and at work.
2. Practical leadership ideas you can apply immediately
   From family meetings to co‑leader alignment rituals, this episode offers concrete practices that translate directly into enterprise teams and leadership partnerships.
3. A refreshing antidote to “perfect parenting” culture
   Danielle and Greg challenge fear‑based parenting narratives, replacing them with a zoom‑out, long‑game approach grounded in culture, intention, and compassion.

Show Highlights

• Family as the first team: Why the earliest lessons about teamwork, expectations, and belonging are learned at home.
• Shared identity in action: The Neufeld family cheer — and how rituals instantly shift five individuals into one collective.
• Incentives that unite, not divide: How a shared “super ding ding ding” reward reinforces team behaviour rather than individual competition.
• High standards + high support: Lessons from elite investment cultures (including Ken Griffin’s Citadel) applied to family leadership.
• Culture lives in the present: Why great culture isn’t built for a distant future — but day by day, moment by moment.
• Family meetings done right: Moving beyond logistics and correction toward appreciation, learning, and connection.
• Rites of passage and individuation: Helping children climb their own mountains while keeping family as base camp.
• Co‑leadership under pressure: How to surface fear beneath non‑negotiables and stay on the same side.
• Why things going wrong is not failure: A powerful reframing of mistakes, hit rates, and “winning enough” in families and teams.
• Media recommendations with a twist: From the Founders podcast to Real Housewives as an unexpected masterclass in group dynamics.

Useful Links & References

• The Most Important Thing Podcast — Danielle DeMarco & Greg Neufeld
  Focused on intentional family culture, leadership at home, and raising capable, connected humans.
• Bruce Feiler – Happy Families
  Referenced for its research on family meetings as a cornerstone of strong family culture.
• The Founders Podcast
  Recommended by Greg for studying timeless leadership and entrepreneurial mental models.
• Real Housewives (Franchise)
  Danielle’s unconventional but insightful recommendation for observing group dynamics, power, rupture, and repair.

Maintaining relevance and purpose as we age requires letting go of entitlement based on experience, embracing genuine curiosity about new things, and focusing our energy on meaningful connections and contributions within our immediate sphere of influence rather than consuming anxiety-inducing information we cannot control.

Three reasons to listen

• Explore how to maintain relevance and purpose as you age without falling into entitlement or becoming disconnected from younger generations.
• Understand the balance between bringing wisdom from experience and staying curious about new developments in a rapidly changing world.
• Rethink what legacy means beyond career achievements, focusing on love, connection, and positive impact on the people directly around you.

Episode highlights

• [00:00] Introduction: A Special Episode in New York
• [01:35] Hitting the Big 6-0: Expectations vs. Reality
• [03:15] Life 6.0 and Finding Comfort in Your Own Skin
• [04:45] Navigating Age Discrimination and Bias in Tech
• [06:50] The Duty of Curiosity and Learning AI
• [08:10] Combating the Fear of Irrelevance at 3:00 AM
• [10:20] Neolithic Floods: The Evolutionary Value of Elders
• [12:35] Defining Legacy: Family, Capitalism, and Spirit
• [15:45] The Power of Love and Connection in Teams
• [17:15] Managing Stress: Moving from Global News to Local Influence
• [19:30] Closing: Celebrating in New York

Links

• Track and improve your team performance with Squadify
• Leave us a voice note

AI transformation is fundamentally a human transformation, not a technology project. Success depends on taking deliberate steps to build AI literacy across your entire organisation while managing fear and maintaining team cohesion.

Most companies are still at the beginning of their AI journey. The key is to start with a clear plan that's reviewed regularly, ensure everyone from board level to front desk has basic AI literacy, and create psychological safety by addressing fears about job loss.

Stephen Hunt is serial entrepreneur whose AI journey dates back to 2011, when he used machine learning and neural networks to for ad targeting. He founded the Square Wave initially as a hobby project to help him understand AI, and he now works with clients on AI transformation, providing training and helping organisations develop AI strategies.

Three reasons to listen

• Understand the leadership, rather than the technical challenges posed by AI transformation
• Start building AI literacy immediately through research, prompting, and training
• Reframe AI as an opportunity for humans to be amplified rather than replaced

Episode highlights

• [00:12:53] What opportunities is AI presenting right now?
• [00:19:46] How to start taking advantage of AI
• [00:22:12] Three core AI literacy skills
• [00:26:40] Start with clarity
• [00:31:12] Where to start
• [00:35:52] Steve's media recommendation
• [00:38:12] Takeaways from Pia and Dan

Links

• Connect with Steve via LinkedIn
• The Square Wave
• Startups Decoded – Steve’s podcast recommendation
• Track and improve your team performance with Squadify
• Leave us a voice note

Many groups calling themselves teams are actually "TINOs" (Teams In Name Only) — collections of individuals focused on their own functional KPIs rather than collective goals. Transforming them into real teams needs three critical elements: a shared goal that transcends individual targets, genuine interdependence through cross-functional strategies, and executing together on making work visible and collaborative.

Three reasons to listen

• Identify the telltale signs you’re in a Team in Name Only
• Transform TINO behaviour into genuine teamwork
• Build psychological safety and interdependence amongst team members so they feel supported rather than isolated

Episode highlights

• [00:01:58] What is a TINO?
• [00:05:31] Defining a clear team
• [00:10:27] The challenges of increased visibility
• [00:12:53] You don't need to wait for a crisis

Links

• Track and improve your team performance with Squadify
• Leave us a voice note