You’re a manager, and some days it just feels like you’re a supporting cast member on a lousy action movie shoot. The bullshit coming from the director has maxed out; the two lines you’ve got keep changing; and it’s dark, which means you’re late going home again. And it feels like you’re 100 miles from your dream of being CEO or anywhere else in the C-suite for that matter.

‘Making it’ clearly means finding a new job or setting up your own business, either before or after you resign in frustration. But before we go any further, just remember that generally speaking, you can only quit once.

But you badly want to be CEO of the corporation you work in now, another business or your own business. How? It’s a long way from manager to CEO, and I can say now from personal experience you’re standing at the edge of a chasm of volatility, uncertainty, complexity and ambiguity; and that’s before you’ve got to the C-suite!

The void you’re on the brink of has operations on your side and strategy on the other. Operations are mainly grounded in the here and now, while strategy is future-focused. Operations are about technical and functional expertise; occupancy of the corner office with the Sydney Harbour view requires a firm grasp of leadership skills and business fundamentals. And here’s the paradox, what gets you to the C-suite (technical and functional excellence) won’t suffice once you’re there; it’s a whole new world.

How do I know? I’ve stood at the edge and I’ve crossed the rubicon.


In leadership, top-notch technical skills are just the starting point, the bare essentials. The significant shift, the one that will help span the chasm is the demonstration or acquisition of business acumen and so-called ‘softer’ leadership skills (the latter of which are paradoxically challenging to acquire). Thriving as a CEO or indeed any member of the C-suite demands superior communication, teamwork and strategic thinking skills, with the latter as the non-negotiable core.

Communication is Conversation

Lots of writers conceive of communication purely as media; they’re wrong. Communication in the leadership space is about conversations; they’re the heart of social and work life. Through conversations, we learn to listen, develop empathy, experience and advance self-reflection. Conversations enable learning that changes us and alters our perception of the world.

Over many years as a manager in commercial and academic life, an incredible source of frustration for me is to watch competent colleagues fail to engage with others when both of them needed to, as did the organisation. I think it’s to do with fear of failure because conversations often don’t produce the results we want. As a consequence, our lives succeed or fail gradually, one conversation at a time. So, no single conversation is sure to change that path of your work or life, but that’s not to say that a single conversation can’t.

What leaders do is to engage in ‘difficult’ conversations more often others. In other words, they engage in challenges that need resolving; they don’t do what Susan Scott (the author of Fierce Conversations) calls the ‘accountability shuffle’; instead, they choose to interrogate reality courageously.

Leadership communication is about authentic conversation and

the conversation is the relationship and we effect change by engaging in robust conversations with ourselves and others.

Susan Scott

Teamwork Through Fierce Conversations

Teamwork is the second pillar of leadership. The old saying ‘it’s lonely at the top’ simply shouldn’t apply. Leaders can rarely effect strategic change without a team. But teams can’t be disorderly, and it’s through robust, fierce well-structured conversations that leaders negotiate order.

Bob Mnookin, an expert at the Harvard Programme on Negotiation reckons that most industrial disputes fail to get early resolutions because one or both parties involved don’t know how to negotiate in an orderly manner; they struggle to hold civil conversations. Indeed, I recall standing outside a room in the Fair Work Commission (Australia industrial umpire) and hearing an employers’ representative and the employees’ representative yell at other (the only thing that impressed me was their command of the vernacular). They couldn’t be civil; it seemed to me they didn’t know-how. Both had fixed positions; neither wanted to work on principles to solve the issues.

Leaders have to make tough decisions; it’s certainly not a popularity contest. But those decisions have to draw on advice from colleagues; that’s how we close the information gap that often exists when we try to make an informed choice. Usually, the ‘higher’ you get in an organisation, the more significant the gap between the information you have and the consequences of the decision you need to make. And that’s why you need teamwork based on conversations.

Strategic Thinking

Most discussion of the third pillar of leadership, strategic thinking, talk about rational, logical, evidence-based critical thinking. That’s a great start, but I don’t think it’s the whole story.

There’s an old meme that pops on social media once every couple of years. It’s a scientist at a chalkboard writing out a massively complex equation. Just before the solution there’s a big gap and in the middle of that gap are the words “and then a miracle happens”. For me, that’s the difference between strategic thinking and critical thinking.

Another example? My first business school Dean, Professor David Weir, recalled working for an entrepreneur in the 1970s. David took him folder after folder after folder of data and evidence about a purchase that interested the entrepreneur. After a couple of days, not nearly enough time to read everything presented to him, the entrepreneur said: “okay, let’s do it!” David was beside himself: “but what, how, when, why?” His employer came back: “It just feels right; let’s get on with it.” As David observed to me some 40 years later “the miracle had happened”.

Connecting the Dots

Let’s put a bit of science around what I think happens in strategic thinking. For me, people who think strategically see that well-known cliché: ‘the big picture’, also known as the ‘helicopter view’. Whatever you call it, the picture is one they build out of connecting the dots between different pieces of information; they’re subconsciously and sometimes consciously (if trained) employing systems thinking.

Strategic thinking focuses on systematically understanding the way that different parts of almost anything connect and how those connections work across time. You don’t need all of the information, just enough to enable you to make the connections. Strategic thinkers connect patterns and form associations between things where others don’t.

Strategic thinkers:

  1. Ask different sorts of questions;

  2. Spot signals that raise issues for them;

  3. Put structures into stories that identify standard processes;

  4. Start building mental models; and

  5. Leverage information, connecting the dots.


So, you want to be a CEO? Are you ready to cross the chasm? Are you? How?

To step off the edge, you need to communicate better, improve your capacity for teamworking, and build your capability to think strategically. There are six steps you need to take:

  1. understanding your business;

  2. mapping desired change;

  3. understanding your target market;

  4. creating stakeholder value;

  5. identifying constraints and opportunities; and

  6. creating impact.

You also need to learn to ask six ‘golden’ questions: what, how, where, who, why and when?

I’ve written on this previously, but one of the best ways to cross the chasm is to follow an appropriate and carefully designed programme of knowledge and skills development that is personalised to you and your challenges. That planned programme should include close networks of people tackling similar challenges or having similar desires or needs and led by an experienced mentor. The programme leader should have not just an in-depth knowledge of business and life but the experience of transforming leaders, business and life.

Programmes such as these often lack genuine connections to the real world. Many people who lead them don’t have the life experiences and will rarely walk through challenges with you. A few celebrate your achievements with an accredited award; many do not.

Seek out someone who invites you to ‘walk this way’ towards a personalised transformation that will work for you, celebrated appropriately.

Want to accelerate the move from manager to CEO? Click here for a look at our high-quality mentoring programme, Transforming Leaders. It offers two accredited qualification over 12-months, leading to a British university MBA in Transformational Leadership Strategy; better than that, it places a bridge across the chasm. Walking over the bridge is up to you.

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