Why many founders get the wrong advice (insights from 20 years with c-suites)

A mentoring conversation this week with a former colleague who's founded a successful company got to 'coach crashes and mentor messes', we called it; when traditional coaching or mentoring fail. I'd mentioned I would be at Web Summit Lisbon next week, and we talked about how its success theatre hides the anguish of struggling founders who might benefit from coaching or mentoring from experienced c-suite leaders in big corporates. I have tried to summarise it here.

The known truth is that starting a company or building a team is always hard than you think. I'm lucky: I regularly meet founders and start-up CEOs through my work. They are pushing boundaries in complex fields. They are often technically magnificent. Their innovations and drive inspire me. Their challenges remind me of my own - both as a leader who's benefited from great coaches and mentors, and as someone who's spent 20 years learning the hard way how to seed, shape, change and build resilient teams.

Successes and failures leave clues, but they're rarely found in the standard startup playbook. This is why we both said we like to learn from both founders and those with years of experience in big corporates.

Three critical blind spots founders can face:

1. The Fire-Fighting Paradox

Most founders live in a constant state of reaction. It's exhausting and it's dangerous. From leading through global crises and major transformations, I've learned that sustainable success isn't about fighting fires faster - it's about building systems that prevent fires in the first place, or extinguish them quickly. The skill is creating simple frameworks that help you think clearly when everything feels like chaos and making time to breath. And yes, we get it wrong. A lot. That's how we learn.

2. The Trust Orchestra

A company isn't just a collection of stakeholder relationships - it's an ecosystem of trust. I've learned (often painfully) that success comes from getting internal and external stakeholders and partners all moving in the same direction, even when their immediate interests conflict. Like conducting an orchestra, the magic isn't in how well each section plays alone - it's in how they come together to create something bigger.

3. The Scale-Ready Mindset

Here's the uncomfortable truth: many fail not because of what they're doing wrong today, but because of what they're doing right. The hero culture that powers early success becomes the biggest liability as you grow. The passionate collegiate fun in a team that got you to 10 people will kill you at 100 or 1000. Having scaled global teams through multiple transformations, I've learned that building for scale is about more than processes - it's about mindset and intentional culture building.

Why Coached Experience Matters More Than Ever

Startups face well-documented challenges: funding is down, markets are volatile, customer needs are poorly defined and even worse, shift faster than ever. In this environment, you need more than theories - you need battle-tested experience.

We agreed that the value of working with people who have led at scale isn't just about their successes and what they have learned from their failures. It's about:

• Making tough calls with incomplete information

• Building cultures that survive change and turbulence

• Turning strategy into execution across growing teams

• Learning how to fail fast without failing fatally

• Using introspective techniques to work through mental blocks

• Stepping back from the daily struggle and taking a calm look from other angles

This goes beyond traditional coaching or mentoring. We've both found standard coaching valuable, but founders need more than frameworks and reflection. They need that combined with someone who can say: "I've seen this movie before. What are we not seeing, and what are the options we haven't considered?"

These are some of the triggers we talked about that make people consider experienced coaches as mentors, or vice versa:

- You're feeling lonely at the top with no one to really talk to

- Your challenges feel more complex than your current tools can handle

- You're hitting scaling barriers that seem more cultural than operational

- The standard startup advice isn't matching your reality

- You need to build systems that can grow beyond your personal capacity to lead

What I've learned from both leading and supporting leaders is this: sustainable success isn't about avoiding mistakes - it's about making and learning from them systematically and systematically applying that learning. Like c-suite leadership, the journey from innovative idea to successful company doesn't have to be a solo expedition. The right mentor or coach, depending on what you need, is someone who brings both battle scars and strategic insight, can help you see around corners and build for the future while managing today.

While mentors and coaches traditionally serve different purposes, seasoned corporate leaders need to master both. A mentor shares battle-tested solutions from their own experience, while a coach helps others find their own answers through questioning and accountability. Effective senior leaders flex between these roles. Sometimes your people need your hard-won experience to avoid costly mistakes. Other times, they need you to step back and help them develop their own problem-solving muscles. It's not about choosing one approach - it's about knowing when to deploy each for maximum impact.