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Online coaching: The ultimate CEO & entrepreneur guide

Online coaching helps solve the leadership problem of it being lonely at the topCEOs, entrepreneurs and founders have a lot in common and their common needs for support are often ignored or not articulated. Online coaching solves this problem.

They are expected to be resourceful and self reliant. To give support and leadership to others, but not to require any help themselves. Often they are expected to have all the answers, but frequently don’t have enough people they can trust – at their level – to be challenged in their thinking. If they do have internal people to challenge them, the need to strip out bias, internal think and the impact of the authority in the relationship means that objective clarity is sometimes hard to achieve.

Coaching helps address these problems. To receive coaching enables you to personally develop, set and keep to commitments, be challenged in your thinking and have someone outside of your business to provide you with a different perspective.

How is online coaching different to face-to-face?

The problem with face-to-face coaching, learning and development is time and attention. CEOs, entrepreneurs and founders are some of the most time constrained individuals. As the ultimately accountable in your business, urgent issues swamp your time and attention. Your ability to carve out time in your diary – let alone your headspace – for important thinking, learning or self-challenge is severely hindered. Your ability to emotionally justify this time often sends even the most emotionally controlled into a frenzy of personal conflict. Then the next urgent email comes into your inbox and the business as usual of no development/ learning and challenge resumes.

Online coaching is increasingly evolving to provide the answer. Past the stage where online coaching was still a time bound electronically enabled face to face medium, online coaching now encompasses a range of interventions, tools and techniques. These interventions, tools and techniques in some cases have evolved to fit the busy executive’s time and attention, and should balance mental challenge, learning and support whilst providing momentum to enable you to achieve the important – and not just urgent – goals.

Ten things you need to know about online coaching for CEOs & entrepreneurs:

Time flexibility – e-learning, coaching by Skype and in-house learning and development support all have their place. However, the busier you get, the more likely that all of these activities will be squeezed out of your diary to be replaced by  urgent, but relatively unimportant activities in relation to your long-term goals. You need to source online coaching that delivers interventions to you that fit into your time and attention gaps.

Attention engineering – if you’re not focused at the time of the online coaching or learning intervention, you are less likely to take on board the new thinking, and you’re then less likely to act differently and do better. Find a service that captures your attention via the channels it uses, the frequency of the interventions and how sticky the interventions are. When you’re paying good money, ensure it delivers good value by maximising your likelihood of change.

Interventions with implications – think different and do better needs to be the focus. Information for information’s sake is a nice to have until it’s converted into a ‘how-to’ do something better. Ultimately if you’re not changing your thinking and your actions as a result of the coaching you receive then it’s failing. It can’t just wash over you.

Challenge your mental ruts – you need to be challenged by your online coaching to bounce out of your cognitive ruts.

Your thoughts construct patterns like scaffolding in your mind. You are really etching chemical patterns. In most cases, people get stuck in those patterns, just like grooves in a record. And they never get out of them – Steve Jobs, Playboy Magazine

This is particularly important because, as the leader of your business, both your time and the seniority of your position mean that challenge is in short supply. This exacerbates your cognitive ruts to the detriment of the open and informed thinking that should drive your strategic decision-making.

One size doesn’t fit all, and your shape changes – your coaching programmes need to be customised to either your needs or focused areas for development. This changes over time as you learn and develop new skills and remove previous mental blockers that were stopping your progress. Your online coaching service needs to track your progress and then adapt the coaching interventions accordingly.

Skills and learning weren’t something for earlier in your career – too many leaders effectively start to atrophy because they stop learning and developing the skills vital for them to be the best leaders they can be. Whether this is because of lack of time, lack of willingness or a belief that they know all there is to know (get to the bottom of the class), all the reasons are unacceptable. Whether CEO, entrepreneur or founder, you’re leading a group of people to achieve a mission. You have the ultimate accountability to ensure that you’re as on top of your game as you could be – for them and you. Leading athletes don’t stop training just because of the medals they’ve won previously do they? Your online coaching programme needs to customise your skills development and wider learning based on the latest business thinking.

Benchmarking the best – throughout your career, from academia to your rise through the corporate ranks, you’ve been competing. As CEO, entrepreneur or founder this shouldn’t stop just because you’re ‘top of the pile’.  An executive coach will see strengths and weaknesses in a range of leaders. You need to use the benchmarking that your coaching service can provide to start to get personally competitive again: this time you’re competing on skills, learning and development.

It’s all about the goals and objectives – your online coaching cannot exist in a parallel universe to your personal ambitions and your corporate obligations. You have targets and milestones you want to achieve in both, and your coach should integrate them into your coaching programme. This ensures that as much as possible the investment in your online coaching is directed towards all your desired outcomes. If possible, your online coaching service will also provide you with regular prompts and challenges about whether you’re working on your goals or focusing on the unimportant.

Your online coach is not your lawyer – you shouldn’t be concerned about getting advice from your coach whenever you need it. Even though you know your lawyer won’t charge you for brief advice, there is a concern that repeated questions will lead to a sharp increase in billing. Your online coach should effectively be in the inner circle of your confidants, and you should expect to be able to ask anything at any time and get an answer as quickly as possible – without fear of extra bills.

Enabling your change – ultimately your investment in online coaching is for you you to change for the better. Real change is a long-term change, not a temporary set of behaviours you exhibit before returning to your old ways. Equally, your new skills and new learning and development must be embedded for them to be retained. Your online coaching service needs to factor this and provide ways in which information can be repeated, key learnings reinforced and neural pathways generally strengthened around the changed you.

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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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