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.”