October 1


New CEO onboarding The ultimate guide

Been promoted to the CEO role? Congratulations. Now the journey begins!

The CEO role is a move out of the comfort zone of functional leadership or business unit management, and it opens up a whole new set of stakeholders, pressures, decisions and responsibilities.

No wonder that even the most accomplished leader can be hit with imposter syndrome, and even the most confident individual can start to question whether they have what it takes. 

Moreover, between 30-50% of new CEOs fail within their first 18 months, whether they're hired from outside or internally, according to Dan Ciampa in the HBR article, After the Handshake.


As a new CEO it’s easy to misread the political situation or overestimate the organisation’s willingness to abandon old behaviours. Furthermore, boards and key executives unwittingly undermine the new CEO’s chances of success by overlooking the cultural and political aspects of the company that the CEO will need to navigate in his/her early months, or by over-emphasising financial and operating goals over specific cultural and relational objectives.

The HBR researchers conclude:

“most new leaders fail not because their financial or operational abilities are inadequate but because their style or political skills render them unprepared to manage the organisation’s culture. Helping new leaders understand that culture and improve their “soft skills” to successfully navigate it may be the best way to increase their chances of success.”

As an advisor and coach to some of the most impressive CEOs on the planet, I wanted to share some tips, best practices, and strategies to help you build your onboarding playbook as a new CEO. So let's get started and explore your new CEO onboarding plan from a whole set of different angles.

The new CEO onboarding plan: your first 30-60-90 days and beyond

New CEO onboarding: Phases of your 30-60-90 day action plan

In a previous article, I examined a typical new leader 100-day plan and distilled it into 18 powerful questions that every executive should be asking themselves in their first three months.

These phases remain true for a new CEO building their 30-60-90 day plan. I summarise these phases below; for more details I recommend referring to the original article.

Before the 30-60-90 day plan starts

Due Diligence: You need to do your due diligence BEFORE you accept the role (which is a great reason to forward this article to anyone you know considering a job offer).

The motto for this phase is CHOOSE A WINNABLE GAME. Before you accept the offer, speak with a handful of stakeholders with varying perspectives, and validate that your 30-60-90 day plan has a good chance of succeeding.

Develop: Use the period between your acceptance of the position and the first day on the role. Many leaders ignore this period entirely with the excuse that they’re too busy wrapping up their previous role or taking a family break.

Big mistake. Contacting key stakeholders before you start will make a huge difference for your new CEO 30-60-90 day plan. It’s a game changer. Your motto for this phase is PREPARE FOR TAKEOFF.

Day 1 of your 30-60-90 day plan

Demonstrate: The motto for your first day is BE THE MANIFESTO. How you show up sends huge messages.

Days 2-30 of your 30-60-90 day plan

Discover: The motto for your first month is FIND THE RALLYING CRY. This phase of your new CEO 30-60-90 day plan is about understanding the people and the issues, and validating your #1 strategic objective.

Days 31-60 of your 30-60-90 day plan

Decide: The motto for your second month is MAKE YOUR MOVE. This phase of your new CEO 30-60-90 day plan is about is when you’re likely to make some major moves, in terms of people and projects.

Days 61-90 of your 30-60-90 day plan

Deliver: The motto for the third month is KEEP IT UP. This phase of your new CEO 30-60-90 day plan is about is a mixture of execution and preparation for the longer term.

Beyond the 30-60-90 day plan

In reality, the first 90 days is just the start. CEOs actually have more like twelve months to make their impact before the board typically starts asking questions, and a major risk is to try to do too much, too soon. 

So the counterintuitive advice is actually the advice given to racing car drivers: go slow to go smooth; go smooth to go fast.

New CEO onboarding plan: Board relationships

The CEO who thinks they can finally stop managing upward is in for a nasty surprise. Instead of reporting to a single boss, the new CEO has perhaps a dozen bosses, one of whom will be senior and who is meant to balance the CEO’s authority. 

So your boardroom relationships will take time and thought. They are neither friends nor confidants (though some may eventually play those roles), but they are superiors who will hold you personally accountable for the company’s success.

Design your strategy to communicate with and educate the board: one-on-one contacts, e-mail updates, distribution of background reading, for example. And architect board meetings to be participatory discussions rather than show-and-tell sessions.

New CEO onboarding plan: Executive team

People decisions are never easy, but they have to be made. “Explicit and sooner” is usually better than “implicit and later.” You will want to provide clarity as quickly as possible, since when clarity is absent, then the rumour mill kicks in, guessing games abound, and anxiousness and political manoeuvring take the place of delivering business results.

A newly-installed CEO at a financial services firm responded to this problem by privately assessing and classifying his senior team into three categories: keepers, watchers, and goners.

  • He reassured all the “keepers” within 30 days of his appointment.
  • He acted on all the “goners” within the first 60 days.
  • And he told all the “watchers” why he was undecided, and what they had to work on - and then asked them whether they were up for the challenge or would prefer to take an exit package instead.

Although this approach might seem tough, even those executives who were terminated appreciated the clarity of his “firm but fair” approach. And it has the benefit of making your requirements and expectations very clear and giving the ‘watchers’ a real opportunity to step up to the challenge.

New CEO onboarding plan: Communications

New CEOs do not generally realise the extent to which their every move, within and outside the organisation, will be scrutinised and interpreted. There is no room for noise and ambiguity, so keep these strategies top of mind:

  • Purge the Provisional. Once in the CEO job, you can no longer afford to have speculative discussions with employees, because any half-baked idea you put forth runs the risk of being latched onto as a good one. 
  • Simplify to 2-3 Themes. A simple, clear message (your ‘rallying cry’), repeated often and illustrated with memorable stories, is the best way to communicate effectively as CEO. Underneath that message, or as part of that message, you might have 2 or 3 sub-themes.
  • Get personal. Weave in why your core message is personally meaningful and exciting to you. As the saying goes, you can’t move others if you’re not moved yourself.

New CEO onboarding plan: Operational decisions

A CEO said that he initially felt like the company’s “most useless executive.” Indeed, as McKinsey conclude, “CEOs should wield direct power very selectively and deliberately.” This is for two reasons.

Firstly, on a very basic level you won’t have time to be close to the business and master all the details - shareholders, analysts, board members, industry groups, politicians, and other constituencies will all demand your attention.

Secondly, you will pay a great price if you use your newfound power to unilaterally issue orders or summarily reject proposals that have come up through the business. The more you intervene directly in operational issues, the less empowered and motivated the wider team will feel. And the greater the risk that you get lost in the weeds. 

As one CEO put it, the need to overrule something is a sure sign of either a broader organisational failure, or of your own failure to clearly communicate strategy and operating principles.

So, if a proposal reaches your table for final approval that you’re unable to ratify with enthusiasm, look carefully at what went wrong:

  • Were all the right people included in the discussions?
  • What was the system for identifying and resolving any potential show stoppers?
  • Were you brought in at key moments for your feedback and support?

Despite the direct power that would appear to come with the CEO job, your greatest influence is actually indirect, to create the conditions that will help others make the right choices:

  • articulating and communicating a clear strategy;
  • putting sound processes in place to guide, inform, and reward;
  • personally embodying the culture/values; and
  • selecting and mentoring key people, especially your management team

This is the “CEO cockpit”, and it takes most functional executives a while to master it.

“CEOs should wield direct power very selectively and deliberately." - McKinsey

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New CEO onboarding plan: Horizon of Focus

The tension for the CEO is this: there are many pressing operational concerns and short-term deliverables to achieve, but the bigger game is setting up the business for sustained success and the achievement of the longer-range vision.

Many new CEOs recall that their biggest mistake was immediately to turn the business upside-down based on incomplete knowledge, on the basis that there appeared to be so many opportunities to add value.

However, there are often significant short-term adjustments a business needs to make, and it’s easy for important long-term priorities to slip out of focus. 

People will be more enthusiastic about near-term sacrifices if they understand the industry trends that are impacting the business, that the company is planning to get ahead of those trends, and they know that a better future lies ahead.

This is “future-back and outside-in” communication. It creates context and motivation and pulls people towards the future.

Therefore, even if the urgent priority is cost-cutting or restructuring, it’s important to communicate as part of your 30-60-90 day plan, what that future might look like - even if only in the broadest terms:

  • What capabilities will be required in future?
  • What future-focused experiments are we undertaking, alongside the immediate action plan?

Building CEO focus, then, is clarifying how you’ll make best use of your limited time and attention, so that your short-term commitments are met whilst making progress on the strategic moves that set the organisation up for long-term success. 

15 recommendations for new CEOs

(source: Vistage)

  1. Take time beforehand for deep thinking and in-depth research.
  2. Start the job rested.
  3. Understand what you’re walking into.
  4. Lay out your game plan.
  5. Prioritise knowledge transfer.
  6. Communicate your intentions so people don’t speculate.
  7. Listen, listen, listen.
  8. Dig into talent issues instead of delegating them to HR.
  9. Build a cross-disciplinary sales team.
  10. Get to know your people just as well as your business.
  11. Find creative ways to connect with your employees.
  12. Resolve conflicts right away.
  13. Approach customers with three questions.
  14. Create a cross-functional sales playbook.
  15. Invite employees to ask you anything.

New CEO onboarding plan: Personal credibility

The first few months will set the tone for your leadership. You have the title, but you now need to establish the right to lead and earn the loyalty of the organisation.

As CEO, all eyes are on you. Is your vision clear and convincing? Are you demanding obedience, or eliciting commitment? Are you serving the organisation, or pleasing yourself? Is the business safe in your hands?

In such a visible role, building your “CEO presence” is key. CEO presence is a short hand for winning hearts and minds; for demonstrating the character, competency and charisma that befits such an elevated leadership role.

This doesn’t mean hiring spin doctors to manipulate your image. It doesn’t mean pretending to be a super-hero: omniscient, omnipotent. Instead, it means doing the deep work so you’re leading from a place of service rather than ambition, fear or people-pleasing. And it means paying real attention to how you conduct yourself in every interaction.

We all have habits and tendencies that tend to undermine our influence and impact. As CEO, these “influence leaks” that didn’t matter so much at lower levels can become more detrimental.

For example, one recently promoted tech CEO I worked with was inadvertently undermining his influence by repeat signalling to his employees that he wasn’t a tech expert. This wasn’t a conscious act; these were just throw-away comments, and the reality was that he had a perfectly strong industry understanding. However, these comments were starting to undermine his credibility in his heavily engineer-led organisation.

Another client, Kirsten, was appreciated for being a collaborative and facilitative leader, but her unwillingness to step in to unresolved management team debates and make and stick to a decision was undermining her influence as CEO. It was draining the organisation’s belief and momentum around the core transformation project that she was championing. We fixed it; but if we’d left that longer it would have become a real problem.

Developing CEO presence, then, is how you establish credibility and build trust and loyalty across the business.

New CEO onboarding plan: Critical conversations

As CEO, you have a complex and interdependent system of stakeholders to manage, and there will be real tensions and competing demands upon you made by these groups.

The weak CEO will people-please, over-promise, and over-rotate to the stakeholders who are screaming the loudest (often investors). Whilst investors are a key constituency, defining one’s goal as shareholder approval may not be in the company’s best interest. As Michael Porter pointed out, actions and strategies favoured by shareholders may not benefit the ultimate competitive position of the company. 

No one said it would be easy! At the end of the day, the board—not the CEO—is in charge, despite the fact that many members will have limited knowledge of the company’s industry.

However, your job is to be a leader, not a people-pleaser, and so your job is to win the hearts and minds of all your different stakeholders and enrol them into a shared understanding of the way forward for the best interest of the firm.

How do you do this? One critical conversation at a time.

Your “new CEO’s world” is filled with critical stakeholder discussions to secure support for your vision and plans. The danger is these conversations aren’t given enough preparation, or the discussions are actually postponed, simply because there’s plenty of other (easier) tasks to be getting on with. 

These ‘CEO conversations’ is a make-or-break activity, as you influence and secure support across the stakeholder ecosystem.

New CEO onboarding plan: Sensing apparatus

CEOs are flooded with information, but reliable information is surprisingly scarce. All information coming to the top is filtered, sometimes with good intentions, sometimes with not such good intentions.

Unbiased information is available from external channels—for instance, through contact with customers, conversations with other CEOs, and affiliations with industry associations.

These might not feel urgent, but do allocate time for such external discussions through a systematic process. They will provide you with perspective and insights that may fundamentally change your plans.

As a new division president of a paper company told McKinsey, “You never find out where all the skeletons are from the inside. I often get more insights into the culture and politics of an organisation by talking to customers and suppliers.” 

In a McKinsey survey, several CEOs also pointed to productive relationships they had with independent advisers who could tell the unabashed truth and had license to criticise the CEO’s thinking.

New CEO onboarding plan: Peer support

As CEO, it can be hard to find peers who can challenge your thinking and provide fresh input into your toughest problems.

And the unique challenge you have as a CEO is there’s only one of you - unlike most other people in the organisation (from account managers to C-Suite leaders) you don’t have an internal peer group to compare notes with and be inspired and challenged by.

Your family and friends may not operate at the level you do, and in any case you don’t want to overburden them repeatedly with your professional challenges. Your board, colleagues, customers & partners all have valuable input, but they are all part of the system and they all have their own agenda.

So, who are you surrounding yourself with to challenge and inspire you, to help you play a bigger game as CEO, and to raise the quality of your thinking and your leadership?

How do you find a room where you’re not the most accomplished leader present? Our article about CEO peer community is worth reading, or you might want to check out Xquadrant’s very own elite CEO mastermind for top tech/digital CEOs.

New CEO onboarding plan: The legacy question

Research shows that executives that make the transition to CEO successfully often focus right from the start on the legacy they want to leave behind. This goes well beyond financial aspirations; it’s the impact you’ll have created amongst all your different stakeholders.

To start thinking about legacy, ask yourself:

  • In what condition do I want to leave this business?
  • What will employees be focused on?
  • What will I have personally stood for?
  • What organisational culture grew out of my leadership?

Sharpening this up, you can ask:

  • What would be my #1 regret if I had to leave without achieving it?
  • What’s the #1 thing that could derail what I hope to achieve?
  • What are my personal, health and relationship aspirations for this period, and how will they interact with all the other elements of my hoped-for legacy?

Conclusion: Thinking deeply about your CEO onboarding

This is a long article, and it’s a lot to digest.

To go deeper, and think about these topics in ‘bite sized chunks’, we’ve written a short email series that goes into more detail on the transition to CEO.  It explores how you can practically sharpen your CEO focus, solidify your CEO presence and master your CEO conversations.

We hope it will help you transform the first few quarters in the CEO role.

If you’re interested, sign up for our free email series: “Mastering the CEO Learning Curve” by using the form below.


Mastering The CEO Learning Curve

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