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The Essential Cheat Sheet for CEO Coaching

CEO coaching can be one of the most difficult coaching relationships to establish. There are a number of reasons for this, but the very nature of the CEO’s role at the head of an organisation is one of the main problems.

The coaching relationship with a CEO is a privileged position, but one that can cause potential conflict with other members of the executive team or Board. They can view the CEO coach as being a threat or, if not as overt as this, a challenge to their relationship with the CEO. The more challenging the CEO coaching relationship becomes, the more likely that the CEO will start to re-evaluate her colleagues against a challenged set of priorities.

It is a generalisation to say that all CEOs share certain personality characteristics, however face

to face coaching doesn’t work for some CEOs if they  find it hard to be challenged or questioned. This is understandable when they are expected to be so self-reliant and resilient. Often they have little experience of directly asking for or receiving support from others – let alone inviting challenge or the questioning of their own skills and decisions. It takes a strong executive team to directly challenge their CEO in the same way that an executive coach would.

So, how to ensure the best chances for a CEO coaching relationship? The answer lies in you being clear about what good CEO coaching looks like, and ensuring that this is what you buy.

  1. Challenge is everything: even arguably more so than other forms of executive coaching, a challenging and questioning relationship is vital to truly get the most out of CEO coaching. This can’t just be ‘invited’ questioning and challenge; the CEO coach should constantly be getting you to think different.
  2. Constant evaluation of your needs: your coach needs to be set up to be constantly evolving the support provided to what you need
  3. Efficient and effective: a coach to a CEO needs to be a peak performer themselves. Long-winded or overly indirect has no place in an efficient and effective coaching relationship. Don’t hesitate to challenge your supplier to provide better quality and value for the time and money you’re investing
  4. Directed learning: as a CEO, your coach should identify opportunities to point you to further reading or sources of insight that will further your personal and professional development. A word of caution here: this isn’t about long reading lists – it’s about distilling out core messages and meaning so that you can use and act on the information and insight
  5. Restless momentum: CEOs are subject to the most time theft by urgent issues that require their attention. Even ultra-efficient CEOs who are able to well manage the commitments and accountabilities of their senior team in running their business can sometimes fail to keep the same discipline over their own progress. Your coach should provide the momentum to keep you to your own commitments. Action prompts, chases and calls to action should constantly nudge your progress
  6. Long-term change: the embedding of personal and professional change at the same time as running a business is a definite challenge. You know that change doesn’t just happen magically: persistent, focused repetition and prompting over time makes change stick and your coach should drive this
  7. Time and attention: CEO coaching is an exercise in advanced communications. Getting messages to stick with you is a huge part of the value that a good coaching relationship delivers. This is not just about getting your attention and getting you to make time to receive the message. This is also about ensuring that all messages are delivered in the ‘stickiest’ ways possible to make sure they impact you long term in the way that you need them to
  8. Always-on support: the reality is that the most committed CEOs love their business, their sector and their job. Their problems, blockers and questions can arise at any time – whether in a break from an executive Board, or on the morning school run. The CEO coach needs to be set up to receive any requests for help and respond to them as soon as possible.

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About Si Conroy

Family man, founder/CEO, investor & CrossFitting ultra runner. Businesses apply cognitive science to goal setting & goal achievement for leaders. Love life.

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