Three Things Successful CEOs Do Exceptionally Well


Over the years I have taken on the CEO mantle a number of times, I have coached many others and  I’ve enjoyed being Chairman and working together with CEOs and their Boards.

From my experience there are three core activities that great CEOs have become expert at:

1. The ability to see the business and the macro environment from a 40,000 foot level;
2. While simultaneously listening empathetically to staff and customers (or users); and
3. Surrounding themselves with great people who they consistently empower to give of their best.

Creating this winning CEO algorithm in either a large corporation or a highly volatile startup atmosphere requires nerves of steel, a strong sense of self and belief in your ability to lead your team.


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Should You Become an Angel or Venture Capitalist? Transitioning from Operational Executive to Portfolio Player


Leading executives can become totally focused on their operational role. Yet at some point, a trigger results in them losing their mojo for working in one business. What type of role is better suited to their next phase in life?

I posit that it is a meaningful transition for them to coach entrepreneurs and manage a portfolio of startup investments.

I’d like to illustrate my hypothesis by exploring two case studies.

Finding His Creative Mojo: From Ad Agency to Angel

David is a successful CEO of a world leading advertising agency. He has been focused for the last 12 years on growing the business, its reputation and its people. When he first approached me he felt that something wasn’t quite right. he had used an executive coach for many years, so understood the paradigm. Yet he realized that he needed to work more with a transformational coach. A coach who not only understood the business landscape, but also had firsthand knowledge and understanding of and empathy with people going through a transformational journey.

He loved to sing in the shower, especially on mornings before a big pitch, or when he was traveling on business. But he found himself no longer singing. This was the initial signpost for him to realize that it was time for him to go on a different journey. Many people ignore these early warning signals until it’s too late for them to change.

We spent our initial time together exploring what had excited him before. We delved into what areas he most feared. We explored if there were deep, unresolved issues that could stand in the way of him making a transformational shift. It is always best to work through such issues in the early phases of a transformation. They may cause blockages in your ability to perform. They could also act as blinkers to you discovering what you find purposeful.

We started the process of getting him to hear his inner voice. It had been suppressed for many years by his ego. This voice is always there in every one of us. We may suppress it to the point were it is so faint that we cannot hear it. What we were looking for from his inner voice was a deeper understanding of what resonated for David. What was his true soul work? In his 20s, he had worked with some start up companies on their market positioning. He had also been active in creating a technology spin out from his advertising agency.

He came to the realization that it was time for him to move on from running the operational, day-to-day side of his agency. It was time for him to get back into the world of creating. At his core he was a creative, which is why he had been so successful in the advertising arena. In particular, though, it was time for David to move deeper into the world of startups. Meaning and purpose for him was about building companies that were making a difference in the world.

This was never going to be a binary process, with him being an operational executive one day and a startup portfolio player the next. We had set that expectation early on. He knew it was a significant journey. It would have many moments: some positive, some negative.

A thought leadership position can benefit the move from operational CEO to Non Executive Chairman. David had no interest in writing books, but was keen to do outreach activities. He joined the board of a not-for-profit organization in the medical health arena. He was invited to be be a regular on a well-known, news-related television show. This significantly raised his profile. He took two further board seats of large companies. This positioning helped him make the mindset shift from single focus to portfolio player. It also ensured the right circles noticed when he made the announcement of his transition to Chairman and startups.

The next transition activity was a robust succession plan within the advertising agency. He identified two executives who had the skill set, drive and passion to step up into joint CEO roles. They were both positive about taking over the operational aspects of the agency. They began working with executive coaches to assist them in this process. David also began the discussion with his Chairman about his decision. They mapped out a plan for him to transition into the role of Non Executive Chairman within 24 months. The Chairman volunteered to take a less active board role.

We then began exploring the role that David should play within the start up space. He didn’t want to take on a CEO or other operational role in any one company. Instead he wanted to build a portfolio, working closely with startup CEOs as a coach. He wanted to ask the hard questions. He wanted to accelerate their growth and keep them on track as they scaled up. He preference was to invest into these companies, rather than consult to them. Their upside would be his upside.

He was comfortable working as an independent agent, as a lone wolf. Although he could see the benefit of teaming up with other investors when it made sense. He was suited to becoming an angel investor. He had significant net wealth at that point. His financial investment portfolio was diversified and included properties and blue-chip stocks. He could afford to allocate a few million dollars towards his initial startup portfolio. He was also of the mind that this was risk capital. He wanted to deploy his capital into companies taking bigger risks that had above average goals. He was mentally prepared for the fact that he may not receive a positive return on investment from this activity. It was to be a learning experience.

We worked closely on how to place him within the entrepreneurial ecosystem. He began to get a feel for how he could determine whether a startup was worth looking at closer. He crystallized his Investment Charter. This set out his strategy for the kinds of companies, types of technologies, geographical preferences, stages of development and many other factors that assisted him make investment decisions. The aim was to ensure he was targeting the right kinds of businesses that could deliver him significant return on investment.

As he started doing meetings and due diligence on potential investee companies, we continued with his education in this area. The aim was to make sure that he was not making emotional investment decisions. It was also to ensure that he was able to draw on his significant business experience. He became comfortable that he could add significant value to the companies that he chose to invest in. He wasn’t keen to join a formal angel group. Nor did he want to become part of the herd that chased investments at pitch competitions.

Some of the companies that he was targeting already had angels circling them. In some cases he had a meeting of the minds with these investors. This was one way he was able to start growing a network of angels he was comfortable to invest with. He also reached out to senior executives were either already active, or wanted to get active, as angel investors. Within a matter of months he had four different informal networks that he was teaming up with.

David went on a three year journey from operational CEO to having a portfolio of board seats and angel investments. He has not only found his inner voice but is also singing in the shower again.

Adventure Capital: A Venture Guy’s Journey

Tom was the CEO of a large communications service provider. He had been in this role for six years, having worked his way there from inside the organization.

Similar to David, he reached a point where he no longer saw colors. Tom’s world became black and white. He approached me with the realization that he needed to make some significant changes in his life. He had worked with an executive coach for a number of years and so understood the power of coaching.

He wanted to explore how best he could get excitement back into his life. He had also become enamored with the entrepreneurial fervor that was sweeping the world. He initially sat on the investment committee of his company’s corporate venture capital group. He found that he enjoyed spending time with their investee companies.

His company had already created a succession plan and there was no need for us to revisit that. He was also well known in the business arena. He had a high profile thought leadership position that we could leverage. We could move forward at a fast pace.

Tom decided to make a clean break from his company. We explored the best positioning for him within the entrepreneurial ecosystem. He didn’t want to operate as a lone wolf. He was more comfortable being part of a formal group that had significant track record and a brand name. He preferred to work with a group of partners from whom he could learn the ropes.

Through his corporate venture capital exposure he realized that he didn’t want to work with very early stage companies. He found this time in a company’s development frustrating. He was well suited to work with companies that had already reached product market fit and were experiencing rocket ship growth. For example, startup companies that were about to receive a significant Series A investment.

It became evident that the best place for him to play would be as a partner in a venture capital firm. He had discussions with venture firms that his company had done deals with. He got on well with some partners of these firms. He started receiving offers from VC firms. He chose to join a well-known firm. They were raising a new fund. This meant he could both participate as a limited partner in the fund and as one of the general partners deploying the capital they raised.

I continue to coach him in his position as a VC. There are many VC nuances he is finding a deeper understanding of – for example,

* the healthy tension between being an individual VC and a partner within a partnership;

* the potential for conflict between a venture guy and their investment companies.

* how best to coach portfolio CEOs – what kinds of questions he should be asking, what signs he should be looking for that they are on target and on track both operationally and emotionally.

Both David and Tom have not only stepped up through their transformations. They have also proven the power of having a virtuous circle by referring some of their portfolio CEOs to me and some of their former colleagues have also expressed interest in coaching.


1. Be aware of trigger signs that a transition is imminent. You may miss the signs and find yourself in a trough – it is significantly harder to catalyse a transformation the deeper you fall into a trough. Heeding the signs earlier is better. This ensures there is no urgency to your transformation journey.

2. Be prepared for significant change. Transformation is never linear and this organic journey may take you places you didn’t initially imagine. Go with that flow.

3. Be prepared to listen to your inner voice. You may have a tussle with your ego not wanting to let go. Eventually your inner voice will win out.

4. The world of startups is not for everyone. Nor is being an entrepreneurial investor. Go there for the right reasons – it resonates deeply with you, you enjoy creativity, you have the right risk appetite and profile. Don’t go there because you’ve read in a business or in-flight magazine how hot startups are or how much money you could make in the space.

5. Don’t burn bridges. Once you’ve made your mind up to transition, do so gracefully. Ensure the right succession plan is in place. Leverage your current position to create your thought leadership position. This will ensure you optimize your transformation trajectory. You already have a solid network in place, they want to help.

[Note: Names and situations have been altered for confidentiality reasons]


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Boardroom Disruption: How Silicon Valley and the Fear of Missing Out Can Reinvent Your Business


The Silicon Valley tech-mythology-machine, replete as it is with unicorns and trolls, is a wondrous device designed as much to assist in reality distortion and suspension as it is in self-paving its streets with digital gold.

We all know the story of how the Valley has reinvented itself through various technology phases. Currently it is awash with apps and social media. Even though they helped create this social flow, a few of the tech pundits are swimming against this tide, reinventing themselves as mindfulness gurus, but that’s a fairy tale for another time.

There is a new tide washing into the Valley: autonomy – artificial intelligence, self-driving everything, asset-rich services on demand and cognitive systems that know us to the point where they are 2-3 moves ahead of us in our own personal game of thrones. Their aim is to be 6 moves ahead, and they are rapidly progressing to this point.

But this is all backdrop.

The real foundation of Silicon Valley, the grease in its gears is FEAR. In particular, the FEAR of MISSING OUT (FOMO) is driving the Valley’s sense of urgency.

FOMO is the ultimate reality distortion field creator. This is best explained through examining the fluidity between viewing a new venture in terms of its friction points versus how much it could scale with limitless fuel. Take Uber as an example. Donning friction-tainted lenses restricted many from seeing it as anything more than yet another taxi service, operating in a highly regulated market with well entrenched incumbents. However, for those who looked at Uber through fuel-filled lenses, they saw its true potential, namely to revolutionise transport. They were able to suspend reality long enough to understand the ultimate promise of Uber.  Those who then went on to invest early enough into the company may be rewarded handsomely.

In a low FOMO environment, i.e. most other places on the planet than Silicon Valley, there is little incentive for people to don fuel-filled lenses. They have the luxury of sitting back and waiting for a venture to achieve sufficient traction, they wait for the entrepreneurs to derisk the business. However in a high FOMO environment, those who hesitate: miss out.

Nowhere else on the planet is the FOMO-meter so high. In fact, it is off the charts in comparison to many other geographies. The same can be said for the boardrooms of so many companies. Does your company have a FOMO culture at executive level? For most organisations the answer is a resounding “no”. How then can incumbents compete against agile Silicon Valley startups? The short answer is that they cannot.

Ask the former Kodak board if they understood FOMO. Apparently not.

I’d like to advocate that every board, every senior executive needs to up their FOMO ante. How high you might ask? Not to hysterical levels, but high enough to palpably increase the urgency around tackling disruptive innovation. High enough to also burn the boats and chart new courses if necessary. Definitely higher than the dual path some would advocate of keeping business as usual turning over while exploring new paths on the side.

How do you instill FOMO into the boardroom?

1. In the short term, have your board do a tour of the Valley. Not the bells and whistles version with champagne on the tour bus, but the grungy start up tour where they get exposed to the highest levels of FOMO.

2. In the mid term, look to bring Silicon Valley into the boardroom. Place at least one FOMO expert on the board. Their experience and skills will prove invaluable to you in dealing with the status quo.


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How to Ensure Chief Technology Officers Present to the Board Impactfully

DCIM100GOPROGOPR0857.Within the next six months as many as 75% of CEOs will institute regular Board of Director briefings by their senior executive team. CEOs will tap *CTOs to do such briefings. How can they ensure their presentation achieves impact with the Board? We run through a tried and tested slide pack template for Board presentations.

Let’s assume your CEO has asked you to do a presentation to the Board on your technology office and its impact on the business. What does the Board want from you? How can you ensure your presentation delivers the right level of impact? This deck provides brevity, cogency and focus to grab the attention of busy Non-Executive Directors.

 Executive Summary

Slide 1:  Treat your first slide as an Executive Summary. It needs to include items that ensure a director tunes in –  grab their attention immediately.

Provide a summary of the purpose of the presentation. This sets expectations upfront. It also accords with the wisdom of

tell them what you’re going to tell them, tell them and then remind them what you’ve told them.

 Core Slides

Slide 2: The Money Shot
This is the first of your core slides. It must cover the contribution of technology to the business success of your company.

This slide should include:

  •  How your company will win as a business – make sure you list the top three things you need to do as a business to succeed.
  •  What business capabilities do you need to build? Set out the capabilities needed in the business to support that position.
  •  Competitive use of technology – detail how technology is playing out in your industry. Include your views on whether your company is ahead or behind with cost and capability. Note that the Board wants your views, not those of some research firm.
  •  How the technology office will contribute – qualitatively (what will your team do to make the business win) and quantitatively (what will your team do to costs/competitiveness/revenues/risks). Also focus on what you will do to close the gap or increase the lead with technology capability.

Slide 3: Technology by the Numbers
Your third slide is also part of the core set of slides and should be in table format.
In the rows you should include business outcomes (BO), technology performance levels (TPL) and technology costs (TC).

Set out a five year time line across the columns – last year, this year, year  +1, year +2 and year +3.

Wherever possible, you should include benchmark measures relative to competitors or similar organizations.

Slide 4:  Risk and its Mitigation
The fourth slide is your last core slide and it should set out the five biggest risks represented by your strategy and how you plan to mitigate them.

Use a quadrant that maps Impact on the vertical (low, medium and high) and Likelihood on the horizontal (also low, medium and high). Chart all your risks, but only include on the slide the five that feature in the top right corner.

Also include a table that itemizes each risk and summarizes how you will mitigate that risk.

Slide 5:  Appendix
Your fifth and final slide is an appendix. It should include items for drill-down with the Board.

What items do you expect to drill down on? Examples include a detailed cost breakdown or skills inventory.

And that’s it – three-core slides is all you should need with a cover slide and an appendix.

Pro Tip:
Make sure you get a copy of the template that your company uses for Board presentations. If there isn’t one, keep your slides clean and uncluttered.

A Director has no interest in fancy pictures or whizbang PowerPoint animations. Don’t subject them to Prezi-induced motion sickness.

 White space, large font and clear messages rule the day.

* This piece is directed at the Chief Technology Officer by name, but applies equally to the Chief Digital Officer and the Chief Information Officer.


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Does Your Business Have the Capabilities for Achieving Exponential Growth?

As CEOs and Boards you are faced with an unprecedented level of pressure to achieve growth. Your company needs to stay ahead of increasingly aggressive competition, from other companies in your industry, from outside your industry and even from scrappy startups who define their own playbook.

Growth is not a lever you turn on or off at will. It requires focus, it requires a set of core capabilities that work together as a well-honed scalable operating system. Does your company have such an operating system in place? To achieve the nirvana of hyper-growth, this operating system needs to be working at peak performance capacity. How close is your business to operating at optimal capacity?


We’ve designed a set of questions that help you uncover whether your business has scale in its DNA, whether it will be constrained by limitations and frictions and whether it has the capability to easily add fuel into its mix.

You can access the quiz via or directly here.


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Live Board: The World’s First Digital Real Estate Signboard

I’ve recently joined the board of an innovative company operating in the real estate signage arena: Live Board.

Here’s a video of their product and the company’s CEO, Costa Koulis, talking about the market and his vision:


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