18 lessons CEOs learned the hard way

Taking over ultimate responsibility for a business as Chief Executive Officer is a big challenge, especially if you’ve never done it before. The CEO learning curve is going to be steep. So instead of learning everything the hard way, wouldn’t it be great if you could take some short cuts?

Imagine that, instead having to find out everything for yourself, you could anticipate what’s in store, and learn what other chief execs have discovered about the first couple of years in the new role. Imagine being able to speak with those CEOs directly, to get the inside track.

That’s exactly what I did in Season 8 of The Impact Multiplier CEO Podcast. I spoke with 15+ chief execs, of diverse businesses including small consulting firms, medium sized telecoms operators, hypergrowth tech businesses, and leading financial services players.

I was curious to find out what surprises they’d encountered as they made the transition from functional or business unit leader to CEO, and what their advice would be for others.


S8E01: The CEO Learning Curve
S8E02: Radical transparency & the CEO learning curve, with Thomas Zanzinger (CEO, inriver)
S8E03: Entrepreneurial surprises, with Julian Dixon (CEO, Napier)
S8E04: When half your leadership team leave, with Alex Shevchenko (CEO, Guavus)
S8E05 ‘Triangulating’ to find great ideas, with Michel Robert (CEO, Epsilon Telecommunications)
S8E06: Building a story for your future investors, with Christopher Traggio (CEO, VOO)
S8E07: Two challenges for every new CEO, with Miguel Giribet Giral (CEO, Cash Converters España)
S8E08: Managing your personal energy on the CEO learning curve, with Gurjodhpal Singh (CEO, Tide India)
S8E09: From Fortune 100 to a high-growth specialist, with John Maynard (CEO, Adarma Security)
S8E10: Difficult decisions on the CEO learning curve, with Thomas Crary, (CEO, Pond5)
S8E11: Bringing specific vision to a business, with Silke Zschweigert (CEO, Jonckers)
S8E12: Becoming co-CEO, with Matthias Berlit (CEO, Inform GmbH)
S8E13: Inspiring the team as you scale into 30 markets, with Timo Buetefisch (CEO, Cooltra)
S8E14: Maintaining agility in a 6000-person business, with Cahê Kuczera Toporowicz (EVP, Amaris Consulting)
S8E15: A hub that attracts top tech talent, with Jason Wojahn (CEO, Thirdera)
S8E16: The real job requirements for a CEO, with Kelly Schmitt (CEO, Benevity)
S8E17: Scaling back to scale up, with Elizabeth Cholawsky (CEO, HG Insights)
S8E18: Growing leadership across the organisation, with Stephen Foreshew-Cain (CEO, Scott Logic)
S8E19: From COO to CEO, and deciding to focus less on sales, with Rory McKeand (CEO, TSG)
S8E20: Leading a turnaround and sale in 20 months, with Enrique Sacau (CEO, Kneip)

There’s a wealth of information and insight in these discussions, but here are just a few ideas from the different guests - and a question to provoke your own thinking, whether you are CEO or not.

1 - Radical transparency pays off. Thomas Zanzinger, CEO of product information management firm Inriver, gave every employee board-level information, which gave everyone a much better understanding of the business and allowed his whole staff to make more informed and empowered decisions. How can you provide more context to your team, and thereby extract yourself from individual operating decisions?

2 - Be prepared for the long haul. Julian Dixon, who founded regulation tech provider Napier, discovered that the entrepreneurial journey of creating your own business required more stamina and resilience than he imagined, and talked about how he ‘made his own’ luck. Where do you need to push through short-term difficulties for the bigger goal?

3 - When key leaders leave, new opportunities arise. Alex Shevchenko, CEO of real-time network optimisation firm Guavus, woke up one morning to find that half the senior leadership team decided to leave the company. He turned it into a real source of energy and growth for the business. How can you flip your current challenges so that they actually become an opportunity?

4 - Get serious about validating, filtering and promoting the best ideas. Michel Robert, CEO of global network-as-a-service provider Epsilon Telecommunications, found that the transition from General Manager to CEO was significant. One of his success tips is "triangulating" to isolate and focus on the best ideas from the many that are generated within the business. How serious are you about bubbling up and acting on only the very best ideas from within your team?

5 - Sharpen your big vision AND deepen you operational insight. Christopher Traggio, CEO of Belgian cable operator VOO, arrived in the job to almost immediately discover a serious fraud, which resulted in the imminent sale of the business falling through. This forced him to get crystal clear about his ultimate vision and the story he would want to be able to tell future investors - AND it forced him to get extremely close to the business, spending a day a week in the call centre himself. Where do you need to clarify your vision, and where do you need to get further into the details?

6 - Be careful about your assumptions about the business. Miguel Giribet Giral (CEO of Cash Converters España) had to master two very different businesses - a bricks-and-mortar retail arm AND an online business. He was comfortable with one; unfamiliar with the other. What’s the area of your business that you’re least familiar with, where your incorrect assumptions might be getting in your way?

7- Manage your personal energy at all costs. Gurjodhpal Singh (CEO of top SME-focused challenger bank Tide India) is overseeing a 3-4X growth plan over just a couple of years. He discusses the need to establish clear boundaries to manage personal energy despite incredible demands on your time. What’s one change to your rhythm that will increase your personal energy?

8 - Be prepared for a whole new set of success criteria. John Maynard, CEO of fast-growing cybersecurity specialist Adarma Security, moved from senior roles in large corporations to the top job in a 300 person business. The needs are completely different, and there were a couple of things he overlooked at first. Where do you need external support to nail your next leadership challenge?

9 - Don’t delay the difficult decisions. Thomas Crary of video content marketplace Pond5 came into the business just as a downturn meant that the business model was unsustainable. He had to make difficult decisions fast, and saved the business as a result. What decision are you putting off right now?

10 - Don’t be afraid to be bold. Silke Zschweigert, Chief Exec at translation solutions provider Jonckers, realised it was time to leave a corporate job she loved in order to reinvent herself and start the next phase of her career. She secured the CEO role with a compelling vision for where the business could go next. Where do you need lay out a bolder vision, for yourself and for your business?

"Some fantastic advice for new-in-role CEOs, from people just been through the learning curve themselves..."

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11 - It might not be what you expect. Matthias Berlit is a co-CEO of Inform GmbH, a provider of advanced decision-making solutions. Being one of four CEO peers brings unique challenges and unique advantages, and there was no readily available guide book for him to follow. Where do you need to let go of standard models and forge something new?

12 - You might not want to scale quite yet. Timo Buetefisch is founder and CEO of Cooltra, the largest provider of sustainable mobility solutions on two wheels in Europe. When he looks back on his journey, he realises that he scaled too soon and multiplied losses - because the business wasn’t quite ready. Where do you need to slow down on expansion, and strengthen the foundations instead?

13 - Don’t write people off too early. Cahê Kuczera Toporowicz of Amaris Consulting started as an Intern and now runs the entire 900+ person Asia region of the business. As well as sharing fascinating insights into how to scale a service business, he opens up about his early failure to hit goals, and why it doesn't predict future potential. Who have you written off due to underperformance, and how can you turn that around?

14 - Win in your core market by winning in the talent market. Jason Wojahn (CEO of Thirdera, a global expert in ServiceNow) built a business from zero to a 600+ people in just one year! Part of his success was creating a 'lighthouse effect' to attract rare tech talent. If you were able to become a magnet for top talent, how would that change your growth trajectory? And what would it take?

15 - You don’t want to be CEO? You might be wrong. Kelly Schmitt is CEO of corporate purpose software provider Benevity, and she never wanted to be Chief Exec. But when two CEOs with “perfect resumés” failed to onboard successfully, she stepped up and realised that she didn’t have to fit in the mould she imagined. What don’t you WANT to do, or don’t think you CAN do? And what if you’re wrong about that?

16 - Scale back to scale up. Elizabeth Cholawsky, CEO of HG Insights, found that scaling back helped her to scale up. She cut 75% of her channel partners - and 4Xed revenues as a result. What do you need to cut so you can focus on what will really differentiate you?

17 - You can't run the company. Stephen Foreshew-Cain (CEO of IT services provider Scott Logic) was surprised when he realised that he couldn't run the company directly! Instead, the levers available to him were mostly indirect. How much focus are you truly putting on the indirect levers of culture, mindset and decision-making processes?

18 - The CEO role is a surprisingly big jump. Rory McKeand (CEO of TSG) was already COO and managing 80% of the business when he moved up to CEO, and yet he discovered it was a surprisingly big jump, with a new level of responsibility and complexity. Do you have the support and community you need to absolutely nail your next-level role?

This has been a great series and I’ll continue to add extra episodes to it over time. For now, if you’re interested in further insights about onboarding in the CEO role, why not check out this article about the CEO Learning Curve?

Next up on the podcast we’re turning our attention to a new season, Mission-Driven CEOs, where we look at what gets top leaders out of bed in the morning and what leadership legacy they want to create.

PLUS, whenever you're ready, why not hit the accelerator on your journey of exponential impact by working with us, or by picking up a copy of Making TIME For Strategy?

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