Leaders Share Their CEO Secrets

09/18/2016 02:38 pm ET Updated Sep 19, 2016

Three West Coast CEO’s involved in cloud solutions and a Former President of Sony Consumer Electronics. A millennial, two Gen X’ers and a boomer focused on innovation, leadership and a quest for being the best, share their secrets on how to excel in the C-suite.

Stepping into the C-Suite requires setting aside most of your assumptions about work. For many who have spent a good chunk of their careers honing expertise to keep up with the unprecedented technological leaps forward, it can feel off kilter to be told, “leave everything you know at the door and enter here.” Welcome to the C-Suite. You are now officially leading a team through it’s impossible future. The question I get from clients who seek me out to join this elite rank: How do I get there? In other words, what does it take to groom yourself to be part of the C-suite, or to become a successful CEO leading your own company?

In established companies, a well functioning HR program with a long-term succession plan will produce C-Suite candidates from within their own ranks rather than having to recruit from the outside. That traditional ladder route is good measure of the quality of your talent procurement and succession planning process. The ideal would be to internally groom talent from entry level up to the C-Suite. However, in today’s world of rapid shuffle and corporate lattice structure, it’s rare that companies manage to hold onto talent longer than five years. Most talent gets itchy and looks to greener pastures with more opportunity. The second factor coming into play are the rapid changes companies have to endure, which can result in major pivots eliminating entire departments overnight. As a result, great talent become collateral damage.

The World Economic Forum identified the critical skills most needed for effective leadership, and it shows up in recruiting at the C-suite levels as well as in coaching. We repeatedly hear about the skills gap epidemic. Many business schools have come under scrutiny for not developing the most needed leadership skills. Beyond the start-up cultures, business schools are often where the next generation of business leaders go to be groomed to ascend to the next level. There’s no doubt we live in exceptionally turbulent times where the rate of change is exasperating for most and few are able to keep pace with it. It’s resulted in a natural weeding out process for many companies.

We’ve identified four core traits that all CEOs from the mature transnational corporation to the garage start-up that leaders need to possess in order to be able to evolve the company into the forward.

Here are four examples:

The Boomer Corporate CEO

I asked Chris Deering, former President at Sony Europe, what it takes to be a CEO today. Chris’s experience started in marketing and sales, spanning from the delivery of traditional physical goods through to digital delivery today.

Deering believes effective communication is the crucial leadership skill to generate great results in technology and entertainment environments. Chris says “from a career perspective, you have to have an understanding of digital sales, revenue, marketing, operations and finance so you can be a complete manager across departments.”

“You’re only as good as your ability to motivate the people working for you. If they are not responding well to change, then you need to change the people. Neither can be fun. And it’s important to understand what motivates a finance person will be different to what motivates a marketer. You have to think about what your people want. They essentially want to be a hero on the path of their career.”

“Don’t just ask your direct reports what’s going on, you need to dig deeper. I would often take the teams out after work, put my credit card behind the bar and ask dumb questions. Everyone comes into the office every day wanting to do his or her best work. They all have a challenge that gets in their way of progress. For example, I’ll ask the sales guy, ‘Are the orders rolling in this month?’ and when they respond with an honest answer that something is getting in their way, that’s when you can see the company blockage and help solve it, so they can do their job’. Having worked with Chris, he was an excellent people leader. He would ask those dumb questions in a meeting, on the way to the pub, in a taxi to meet a client and just about any opportunity he got.

Deering first inspired the team in the lead up to the PlayStation launch with his mantra ‘the paranoid survive’, inspired by former Intel CEO Andrew Grove. Grove was famous for creating a company that was able to adapt and become the number one chip manufacture in the world. He believed that organizations were a living organism; it has to continue to shed its skin. Methods have to change. Focus has to change. Values have to change. The sum total of those changes is transformation.” Grove shaped not only Intel but also his philosophy and management style was widely adapted across Silicon Valley as the guiding principles and elevated to a cult like status that was hugely influential as a predecessor to Jobs. Chris echoes this philosophy. This attitude and thinking from the top formed the culture that contributed to Sega giving up their hardware business. This attitude and commitment to get rid of company blockages creates the momentum to succeed.

I asked Chris what he would want to share with emerging CEO’s. His advice was to “be sympathetic and aware of what other people are going through. Have your eyes open, be curious, and remember everyone comes to work to be a hero. It’s the CEO’s job to minimize friction points to ensure success.”

Gen-X C-Suite Exec and Start-up CEO

I asked Gen-X’er Don Parker, the founder and former CEO of Shotgun what it took for him to start a company from scratch to create an innovative product that served his clients. His company was acquired by Autodesk.

Two years after acquisition, he is still leading his company, a difficult accomplishment for any founder. His advice, “Build the best company you can. Solve as many problems as you can for your customers and partners. Build the best culture. When you create value, you will have options. Don’t become distracted on an exit. Just build the best possible product. Don’t chase acquisition. Don’t be desperate, or your priorities will be out of sync.”

He offered some advice on making the jump to CEO of a start-up “I didn’t think I was ready for CEO, and tried to get others to lead Shotgun. I received the best piece of advice from my mentor in Toronto when I was going to start Shotgun at the same time my partner became pregnant. He told me ‘You need to do it. You owe it to your child to take this risk now. Don’t be scared. Don’t feel trapped. There’s risk in every career scenario and if you can manage stress and risk, do it (of course, after due diligence).”

But what success indicators are there about C-level innovators like Don Parker? His advice, ‘you’ve got to have a constant and unquenchable thirst for learning. If you’re plateauing and not learning, that’s a problem because it curtails the company’s growth. Get used to getting in over your head and start learning like crazy so you can adapt to customer and market needs to lead teams to innovate”. Clearly a learner mindset is key, which echoes back to my first major aha when reading Peter Senge’s Fifth Discipline.

The transition from independent company to acquisition accelerated Don’s need to be able to adapt and learn even faster. The market requires constant problem solving, which demands coming up with untried solutions to challenges as they present themselves. I asked him what had changed in the past two years. He relayed the challenges he faces are the same - They range from ‘leadership and vision to aligning strategic partners, to managing internal investors, to building the culture, to working with the teams, to create a great product.” One of the big challenges that resulted from the transition from external to internal investors means leaders must constantly engage in lobbying to encourage investors to be willing to take the necessary risks to continue a path of productive growth. These dynamics require strong strategic, communication, presentation and relationship building abilities on the part of leaders. CEOs need to be able to steer an organization’s culture and product in an authentic and transparent way. The goal is achieving long-term sustainability and marketplace relevancy.

Millennial Founder

Mik Naayem, a 28 year old millennial start up CEO, joined forces with former Electronic Arts CTO, Alan Price to start a charity gaming company for students to cover school fees. The company pivoted to a live events engine for mobile game makers after 18 months and has created the holy grail to mobile games companies trying to retain and monetize their games customers. Based in San Francisco and Vancouver, Naayem has diligently focused on product development and the company’s vision with his co-founder in Vancouver.

“Being a start-up CEO is trial by fire, where you’re thrown in and told to swim. I figured out how to swim by surrounding myself with an experienced team and external mentors. I worked with an executive coach to learn interpersonal communication and EQi so I could work out how my interactions affected the team. I got very comfortable asking for help – but I had to be genuine, curious, honest and transparent to gain trust from investors and the internal team.” With Naayeem communication and strategy were the essential skills. Executing on a vision requires a game plan, being able to ask for help, learning about how to create the right solutions and a strategy to achieve the end goal. CEOs need to pull teams together to effectively execute on a shared vision and that requires great communication and EQ skills.

Gen X Serial start-up CEO

I asked Gen X’er Danny Robinson a serial start-up CEO what it takes to be a CEO today. He’s built four internet companies and an accelerator investing in start-ups and best known as CEO of Perch and is a member of the informal ‘Maple Syrup Mafia’, where the group is bound together under the idea that funding Canadian Start-ups raises the start-up tide for the entire ecosystem.

His advice to budding CEO’s, “As a younger CEO in a hot space with a hot start-up, a lot of VC’s, angels and investors will encourage the CEO to shoot for the moon to build a billion dollar company. The money is what people want to hear. They need to know that there’s an intention to build a billion dollar company or they won’t invest. What happens when you don’t build the billion-dollar company? There’s the chance of missing smaller exit opportunities of $100M that can help the start-up CEO at the beginning of their career."

The focus on a big exit can distract from the reality of what the company can really become and in the face of that delusion, the start-up can pass on exit opportunities that are more appropriate for the product that’s been developed. It’s always better to exit cleanly than fail big when you’re starting out. A successful exit creates a path to move forward. It takes humility on the part of the CEO/Founder to recognize an appropriate opportunity to exit that may be less than the ‘dream scenario.’ The reality is very few companies become billion dollar unicorns.

"My leadership mantra is to build, be able to be wrong, try new things to stay ahead of the competition. If you’re not creating something, then you are by definition a follower. The culture needs to be able to endure mistakes and learn from them. Creating the culture of trust is about celebrating the constant act of trying new things, and focusing energy on learning what worked and what didn’t work. Applauding the process of learning to move forward is key, as well as knowing more than most of our competition so we can effectively lead the innovation for our area of expertise."

Danny’s last piece of advice that he lives with daily, 'What am I doing today and who can I delegate it to? Having the right people, doing the right things, is critical.”

Start-ups fail when the CEO wants to do everything, isn’t learning, and can’t scale. If they can’t scale, they’ll need to hire an outside CEO. Investors and the board want a start-up founder who can scale the company while maintaining the organization’s leadership, vision and culture."

Leaders create other leaders, and Danny has been instrumental in creating innovative leaders. His former employees are the founders of Barracuda Networks (Bn$ company), also the number two at Broadband TV, and countless other entrepreneurs that have successfully started start-ups.

We talked about the Maple Syrup Mafia, yes the legend is real, which Danny is involved. The Maple Syrup Mafia strongly believes in the start-up scene, which includes Ryan Holmes, founder of Hootsuite.

One thing I know for sure, is that emotional intelligence is critical. And it’s clear that it’s still the case when speaking with Chris, Don and Mik who work through challenging and constantly shifting market environments. Emotional intelligence remains the lynchpin of all the skills to thrive in the C-Suite.

Here are the four core soft skills demonstrated by these three generations of CEOs:


Joining the C-Suite is about being a strategist who can steer the organization, and ultimately the company on course toward achieving its bigger objectives and vision. In the C-Suite, you are part of a team shaping the company and molding its future position. It’s less about what you know and more about your ability to learn and remain teachable. To be an effective strategist, you have to be possess emotional intelligence, be able to integrate new information and anticipate what’s coming. C-Suite executives needs to be able to figure out the big picture and hold in their minds an understanding of how several different forces at play can impact an outcome. Here it’s about being good at chess. For the C-Suite you are better off taken a MOOC on strategy than learning Java Script.

Change Management

You need to be able to innovate and manage change in an organization at this level. The rapid advancement we are experiencing as a society due in large part driven by technology means that organizational leaders need to be really effective at leading change and innovation in order to thrive and succeed in their ultimate objectives. Change management is a big weakness in many corporations. The ability to be able to finesse a transition and effectively facilitate change has never been more critical.

Relationship Building

You can manage across divisions as well as down. The ability to develop and maintain relationships across departments and form allegiances is vital today. It requires building trust and being trustworthy. Business at the end of the day is very much about human connection be it in a business development context or an internal department context. We are our relationships. Joining the C-Suite requires the ability to really excel at managing relationships and maintaining positive momentum. Avoiding unnecessary conflicts and being able to steer conversations and re-direct actions to achieve the end goal is critical. It may be one of the reasons the people who end up in the C-Suite tend to be the “C” students who were popular in college rather than the straight “A” students who spent all their time in the library. The ability to master relationships and be artfully social is key here.

Communication and Presentation Skills

Polish, an ability to be articulate and effectively communicate ideas is becoming increasingly important for today’s leaders. In today’s media saturated world where a company’s public image is largely impacted by both social and traditional media, leaders must be presentable in terms of poise, how the hold themselves and both verbal and written communication. It’s one of the reasons some companies have banned employees from Facebook. It’s too much to manage from a corporate level. It’s also why etiquette courses are being taught inside corporations.

Going Forward

For HR and succession planners, the question becomes how to pick, retain and subsequently groom talent for the C-Suite. It’s not to say that technical skills aren’t important, but they matter less in today’s rapidly evolving world. As McKinsey recently reported, “When the time comes to appoint a new CEO, corporate boards face a difficult question: promote an executive from within or choose an outsider? We turned our own lens to this issue and found that the performance of outsiders and insiders differed significantly. Externally appointed CEOs have a greater propensity to act: they were more likely to make six out of the nine strategic moves we examined.” The C-Suite becomes about steering an organization, having good judgment, a calmness and knack for leadership. Often replacing a founder is the best decision for an organization.

At the end of the day, CEOs serve the interests of boards, shareholders and investors. While driving the vision of a company, they are tasked with the delicate charge of balancing the financial goals with product goals and customer needs. Most start-up CEOs are driven by a product vision and the inclination toward innovation but weak on the management side, which leads many start-ups to having their founders be replaced by new CEOs. It’s a challenge to grow in this area. With a few exceptions, we’ve observed that the balancing act between the managerial bottom line needs and stretching toward achieving the never been done before requires a team approach and fluid communication among all parties.

There are many interests that have to be met in an organization and the CEO serves the function of making sure all those interests get met. He’s the chief in command and essentially his management ability will make or break his ability to succeed. If he doesn’t deliver for his shareholders and investors, he will be replaced. Many visionaries compensate by surrounding themselves with effective managers.

There’s the management CEO and the Founder driven by a vision to create something. They tend to be different career paths. It’s not that people don’t jump from one side to the other. They do,, but generally the resumes are radically different, and the path to landing in the C-suite varies depends on the chosen track. All that said, there are core characteristics that must be possessed by both management types as well as visionaries in order to successfully obtain and maintain the title of Founder/CEO. These abilities often have less to do with technical competency and everything to do with strategic thinking, vision making and ability to lead, emotional intelligence and insatiable curiosity. Both the c-suite exec in the transnational corporation and the garage start-up founder need to continually develop these areas to move themselves and their companies FORWARD.

Caroline Stokes is founder of FORWARD, a human capital solutions company for global innovation leaders.

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