Hi,
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I asked 100 CEOs this question, and here are the top 5 answers:
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Hari Ravichandran, Founder and CEO of digital safety unicorn, Aura; investor, named on Forbes 40 Under 40 list in 2014 and 2015. |
“There was a point in my entrepreneurial career when my team said, “You usually just tell us what to do and we do it.” It came during an offsite with the executive team, they believed I had structured the culture to revolve around my direction and insights instead of empowering individual teams to independently problem-solve.
I was grateful for it. It forced me to confront the fact that what had gotten us here wasn’t going to get us to the next level. Stepping back doesn’t mean you’re failing; it means you’re creating space for your team to thrive.
By staying so closely involved, my team missed out on chances to grow. But when I started to step back, they surfaced new ideas, became more confident, and it strengthened our trust and communication.
I stopped jumping in with solutions and started asking better questions. Today, our meetings are more collaborative and conversational, and our customers experience the value of this shift every day.”
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Aimee Smale, Founder and Creative Director of Odd Muse, named on Forbes 30 Under 30 list in 2023. |
“In 2023, I was running Odd Muse with no senior management team. The brand was exploding, we had viral moments every other week, opened stores and debuted at London Fashion Week. From the outside, it looked like a dream, but behind the scenes, I was the default manager for every team and every decision - but I hadn’t built a leadership structure to support it.
My stress was constant. My silence, tension, and rushed decisions set the tone. The team began to hesitate and second-guess themselves, and the culture grew shaky because I was. I thought being “hands-on” was a strength, but I was becoming a bottleneck. Worse, burnout and emotional withdrawal stopped the team from being honest with me—they were trying to protect me.
The tipping point was hiring someone senior and stepping back too fast; they were wrong for the business, but no one wanted to be the first to say something negative. The team had seen me unravel, and I realised I couldn’t just delegate my way out - I needed to build trust, safety and structure.
Now, I’ve started handing over creative, shaping how I see myself as a Creative Leader. My hiring has improved; we’ve brought in roles like Head of Growth, Head of Creative, and Finance Director. I’m still taking time on the first C-suite hire.
If my team read this, I think they’d say I didn’t realise how much they looked to me for emotional permission. I unintentionally created a culture where no one felt senior enough to challenge my calls, even when they should have.”
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Phil Gilbert, Former transformation leader reshaping IBM with design thinking at scale, serial entrepreneur, and author.
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“In the early days of IBM’s 21st-century transformation, I kept hearing about “bottlenecks” — leaders blocking progress, slowing decisions, stalling innovation. The pattern was consistent: teams felt trapped between our ambitious goal of empowered problem solving and the outdated command-and-control processes favored by executives.
But closer inspection revealed something unexpected: our most effective teams all had a particular kind of middle manager — one who shielded them from the noise above. These leaders had the courage and skill to protect their teams from counterproductive demands, allowing them to focus on delivering value. The nickname they earned inside the program was crude but apt: “sh*t umbrellas.”
The truth was these managers weren’t resisting change — they simply didn’t have the tools to translate their teams’ new operational characteristics into the reporting their upline managers expected. Those who figured it out became the umbrellas. The rest needed help. It was like being asked to operate simultaneously at two speeds: a new fast one with new characteristics, and the older slow one for teams yet to be brought into the program.
Too often in change initiatives, we teach the new thing to everyone, instead of teaching middle management how to manage the new thing. These are very different tasks.
Once we recognized this, we built a lightweight program giving managers clarity on what the new way of working meant, what artifacts and behaviors to expect from teams, and how those connected to upline reporting, strategy and results.
The impact was immediate. Many “bottlenecks” became high-impact leaders once they were given the tools to manage the transformed teams.”
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Natalie Ellis, Founder and CEO of Bossbabe, a global digital community for women and entrepreneurs around the world. |
“When I returned from maternity leave, I realized I had built the business to be far too dependent on me. While I was away, things fell apart—team members called me in tears because launches weren’t going to plan. It was a wake-up call that my leadership hadn’t set the team up to thrive without me.
Back at work, I fell into old habits: intensity, quick decisions, saying yes to everything. But now I had a newborn, and the weight of everyone’s dependency was crushing. I felt I couldn’t do it anymore.
At first, I tried to step away. I asked my co-founder to buy me out, but after six months of negotiations, it became clear the business was too tied to me to make that feasible. Instead, I chose the harder path: I bought the company outright and committed to rebuilding it in a way that wasn’t reliant on me. That meant restructuring the team, rethinking how we worked, and essentially burning down what the business had been to create something new.
At the same time, AI was beginning to take off. I knew competing with it was a losing battle. AI can replicate information - but it can’t replicate human connection or lived experience.
So, I doubled down on what AI can’t replace: community and real-world tools. I curated about 60 templates we actually use - scorecards, briefs, meeting frameworks—practical resources grounded in experience, not theory. Combined with a tight community, this made our offer truly AI-proof.
For any founder feeling trapped by their own business, my advice is to strip things back to the essentials. Keep only what’s necessary to keep the lights on, and cut everything else. Give yourself three to six months to step outside the daily grind so you can be proactive, not reactive. Only from that place of space and clarity can you make the tough decisions, about team, finances, or structure, that will allow your business to grow without being built entirely on you.”
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Daniel Priestley, Founder of Dent Global, Co-founder of ScoreApp and BookMagic.ai, speaker, and best-selling author. |
“Recently, I felt I was failing as a leader. I had done the things I knew how to do, and they weren’t working like they used to. My strength is big ideas - the kind that get the business off the ground, but I was weak when it came to the hundreds of details and improvements. Now, we were at the stage that demanded exactly that.
For months, I felt pretty helpless and out of sync with the team. I was showing up, but I wasn’t the leader we needed. The business had evolved, but I hadn’t caught up.
Then we brought in a new Managing Director. In his first week, he did 30 1-1 meetings with our team. He spoke for hours with Customer Service, Development and Marketing teams. In week two, he shared a list of 100+ small improvements. By week three, he’d already begun making changes.
It felt like a complete change of season inside the business. It made me realise something simple but hard-earned: I didn’t need to become someone else - I just needed to hire someone great at the part I wasn’t.”
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Talk soon,
Steven