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Executive Coaching: A Step-by-Step Guide

Executive Coaching: a step by step guideExecutive coaching is becoming increasingly important for CEOs, entrepreneurs and founders of businesses as a wider acceptance of the emotional side of running a business grows.

“What’s the most difficult CEO skill? Managing your own psychology……very few people talk about it, and I have never read anything on the topic. It’s like the fight club of management: The first rule of the CEO psychological meltdown is don’t talk about the psychological meltdown…”

– Ben Horowitz, cofounder VC firm Andreessen Horowitz (sold Skype to Microsoft for $6.5B profit within 18mths of ownership)

Executive coaching is not yet a mainstream investment, and so how to buy and how to use executive coaching services most effectively is not immediately obvious.

The selection and engagement process is extremely important considering the levels of trust and expertise required for the relationship to work well. If you get it wrong, or approach the process with the wrong set of buying criteria, there is a good chance that the relationship will fail. If you get it right, you may establish an enduring relationship that enables you to get to places you never thought possible.

The relationship has separate stages and a clear framework that can be focused on to try and give it the greatest chances of success:


Ask yourself what you want out of executive coaching and then ask others what you need out of executive coaching. This can be as simple as taking a sheet of paper and listing what you feel is currently missing in terms of:

  • The support you need from others
  • Your learning/ knowledge gaps
  • Your skill gaps
  • How you are failing to achieve your longer-term goals and objectives

Then ask one or two people who know you well the same questions. Combine the two answers and you have your coaching objectives.


You can now take your coaching objectives – which are a combination of your learning/ knowledge and skills gaps plus longer-term goals and objectives from above – and identify the type of support you need to address them.

Business coaching, executive coaching, mentoring and learning & development tend to be provided by different suppliers – be they independent consultants, coaching organisations or large learning & development corporations.

The problem often is that the executive has a mix of needs coming from the evaluation stage. The best thing is to look at where the majority of your needs lie and then try and find a supplier that best fits your requirements and your budget.

Your coaching objectives are the best ways of selecting a supplier. Ask them how your personal and professional goals & objectives, learning/knowledge gaps and skills gaps would be captured in the coaching relationship and how progress would be prompted and tracked.

Operation & execution

When you have selected your executive coaching provider based on your coaching objectives, you now have to make the relationship operational. This means where possible going through an assessment process to understand where your learning/ knowledge and skills gaps actually are. Ideally this should involve a benchmarking against a high performance leadership skills framework. The results from this assessment process can then be combined with the detail of your coaching objectives to help create the basis of your coaching programme.

You then need to work with your coaching provider on clarifying your longer term goals and objectives – both personally and corporately. These need to be integrated into your coaching programme to avoid any diffusion of effort or conflicting activities.

When your interventions or sessions commence you need to look for a number of indications of a good coaching relationship. One of the most important of these is the challenge you receive. You’re paying to be challenged. For you to do better in business, you need to think and act differently, and this involves you shifting perspectives as well as values and beliefs in some circumstances. After all, if what you knew now was sufficient you wouldn’t need a coach. As in sport, you may have the raw ability, but you need someone to help you achieve your full potential.

An equally important indicator is your personal sense of learning and progress. Ask yourself what you’ve learned over the last month. What new business concepts do you now understand? What new skills are starting to develop? How on top of the latest reading relevant to your coaching objectives and learning needs are you? This indicator also captures the skills of the coach or coaching service: if they have nothing to teach you, you will not feel a personal sense of learning and progress.


One of the main reasons executive coaching fails is that the leader judges the coaching programme ineffective. Assuming you’ve been methodically through the steps above, any lack of effectiveness is most likely to be as a result of a lack of one of three things: time, attention and traction. The first two could be argued to be your fault. If you don’t invest the time (as well as the money) in the coaching relationship, and if you don’t give it your sufficient attention, then even the best designed programme will fail. Immediately thought you can see there is a fundamental point of tension here. Show us a CEO, entrepreneur or founder who doesn’t have limited time or attention. This is compounded by increasing levels of information overload. At MyNeuroCoach we believe that it is the accountability of the coaching provider to secure the leader’s time and attention. Online or remote coaching – particularly when using tailored SMS and email coaching cycles  – is particularly powerful to achieve this.

The third likely reason for the coaching ineffectiveness – traction – is definitely the fault of the coaching provider. You need to ensure that the interventions you receive or the sessions you have are intrinsically effective. How is information delivered? Is it clear? Do you engage with it? Is it impactful, and do you remember it sufficiently that it changes the way you think and behave?

Sense of support and progress

The next culprits in the failure of executive coaching are lack of support and lack of progress. Lack of progress often comes down to the challenge of measuring the impact of any coaching or learning and development. A personal sense of a lack of progress cannot be argued against. However, this should have been avoided with the leader’s benchmarking against a high performance leadership skills framework. If this is undertaken during the assessment stage and then regularly thereafter (ideally quarterly), there is the perfect basis in place for tracking progress.

As a CEO, entrepreneur or founder, the support you receive is of paramount importance. The executive coaching relationship is such a close one that it should feel at the level of close confidant. Whenever you feel blocked, have a concern or a question, you should be able to reach out and get a response as quickly as possible.

Act, embed & retain

This is the feedback loop point in our step-by-step guide to executive coaching. As well as developing new skills and benefiting from learning and development against identified needs to become a high performing leader, you need to ensure that all this ‘new’ is embedded and retained.

Actions, repetition and reminders are some of the best tools. Calls to action are one of the best ways to embed the newly changed thinking that is enabling you to do better in your business. Ensure that these are an integral part of your coaching programme. Layer repetition on to these calls to action. By making the same point in slightly different ways, at different intervals [spaced learning link here], you are most likely to embed & retain learning without having to try and study the material to commit it to memory.

Reminders of your goals and objectives should also play a big part in this action step. Interventions or sessions should challenge your progress, question how you are spending your time – if not on goal-related activities – and generally chip away at you to ensure you are always progressing the important and not just the urgent.

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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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