What I Learned from Coaching 100 Senior Leaders By Ivan Schofield, Leadership Coach & Advisor, via All Together’s Business Community

At All Together, we’re lucky to count Ivan Schofield as a longtime Volunteer Advisor and supporter. Ivan, after a long career of which 16 years as a CEO and 7 as a NED / Chair, has coached many prominent and successful business people – from founders to CEOs in the private and publicly owned companies – and has a rare gift for helping business leaders adjust rapidly to greater responsibility or a changing context .

We asked Ivan to share some of his reflections on the most common themes that come up in his work. As ever, his insights are practical, honest, and immediately useful to anyone building a business.

Over the last seven years I have had the privilege of supporting 100 senior executives as a coach. In different ways, they are all ordinary people but with a combination of ambition, talent and experience which led them to be in senior leadership roles in a period of extraordinary disruption between 2017 and 2024.

Each individual was, of course, unique with their own blend of early life experiences, character traits, education and professional experience combined with the uniqueness of the particular organisational and stakeholder context at the time of the assignment. And, moreover, the range of roles was great… from NHS consultants and healthcare professionals, to Founders and CEOs of significant organisations

But notwithstanding the uniqueness of everybody’s situation, were there common themes? The answer is “yes” and I am delighted to share these themes with you… because if you are on a leadership journey, or working with somebody who is, then the chances are that at least some of these issues will be familiar to you. So if you do recognise these issues then, firstly, you are in good company and, secondly, rest assured… solutions are available!

Here are the five themes that come up most often in my coaching sessions—and why they matter.

1. Effective communication

Across the whole cohort the most significant issue that people face related to communication.

Conveying confidence with senior stakeholders was the top issue, particularly for board level executives. Senior leadership entails demonstrating confidence with senior stakeholders (board members or shareholders) and this can be unnerving and require a certain style of communication, the key being to learn to “look straight ahead” and not “up” when dealing with them … shifting the dialogue from potentially awkward “child-adult” or “parent-adult” transactions to “adult-adult” ones.

Other communication issues related to handling conflict effectively; communicating effectively under stress and creating accountability in appropriate ways … all relating to the challenges that we face when communicating in challenging situations and also recognising that, as we get more senior, our words carry more weight and impact on others.

2. Building capability

It was very common for leaders to hesitate to make tough decisions around people and structure. This is understandable because this involves making difficult decisions about people who are perhaps solid performers but not able to keep up with the pace of change or organisational development. However, delaying making such decisions comes at a price in terms of progress and, very often, stress and workload for the senior leader.

As a CXO very wisely said to me very recently… “60% of my role is ELT and board-related so I have to build an effective structure for this to work”. It is relatively uncommon for new leaders to spontaneously recognise this.

3. Compelling Articulation of vision and strategy

Problems relating to unclear articulation of vision and strategy were actually the most common coaching topic and importantly, this was also common for CEOs and MDs who, of course, had a clear idea about their strategy but needed some help and encouragement to simplify it and articulate it in a compelling way that works up to the board and right the way down the organisation

Also, newly promoted senior leaders tended not to spontaneously grasp the importance of articulating the strategy for their part of the business. A common consequence of this was that they found themselves “on the back foot”, pursuing someone else’s agenda, often driven by short term performance imperatives.

4. Stakeholder Management

Stakeholder management was one of the most common areas and particularly challenging for CEOs and people new to senior functional leadership roles. As a backdrop to this it’s important to bear in mind that the period of 2017 to 2024 was a particularly challenging one … Maintaining board confidence in such situations is challenging, but somehow executives need to find a balance between being realistic and optimistic, remaining close to the detail whilst also demonstrating command of the overview.

Also, many people new to senior leadership roles were surprised at the efforts that they needed to go to build and manage stakeholder relationships. I have many times heard people say “I don’t do politics” which is unfortunately a very limiting mindset. The key is to recognise that managing the stakeholder environment is an integral, not optional, part of the job of senior management so therefore has to be embraced… proactively and, of course, with integrity.

5. Confidence & Letting Go

Finally, helping people with the emotional journey is an important part of the work.

The theme of self-doubt was common and this is commonly referred to as impostor syndrome. Self-doubt is very common amongst senior leaders particularly when faced with significant change in responsibility. Self-doubt can lead to feelings of inadequacy and worthlessness which can impact

confidence and performance. This is a complex area which I explore in this recent article (https://www.and-become.com/insights/the-great-pretender).

Another common key theme was to do with letting go. Sometimes senior leaders struggle to delegate/let go because they want to protect others or because it makes them feel safer… clinging on to approaches which served them well earlier in their career (and got them promoted). See my recent article (https://www.and-become.com/insights/how-to-stop-doing-your-teams-work-for-them) for more about this.

What This All Means

Whether you’re navigating your first funding round or preparing to step back from day-to-day operations, leadership is a journey that demands constant adjustment and a great deal of self-reflection. The best leaders stay curious, open, and humble and are avid learners.

If nothing else, I hope this piece helps you feel a little less alone in the process.

If you’d like to read my full reflections on coaching over 100 senior leaders, please contact me on ivan@and-become.com for an extended version of this article.

And if you’re a founder or CEO looking for practical, human advice from people like Ivan who have “been there and got the t-shirt”— All Together offers access to experienced Volunteer Advisors from businesses like Innocent, Yo! Sushi, Octopus Energy and more. Learn more at www.alltogether.company