An open letter to the new Managing Director – my leadership lessons 2016-2020

An open letter to the new Managing Director – my leadership lessons 2016-2020

Dear Sarah,

Earlier this month when we announced the news that you’d be taking over as Managing Director at Deeson, I started writing this open letter. I wanted to share with you some of what I’ve learnt over the past four years leading the agency.

I write this not in an attempt to tell you how to do your job – you need to be your kind of leader, not try to emulate the way I chose to do things – but in a genuine attempt at personal reflection on what it takes to be an agency leader in 2020.

Deeson, Canterbury

Less than four weeks have passed since I wrote the content for this letter, yet so much seems to have changed. We’re now locked down in our homes in the midst of a global pandemic. The economic future that lies ahead is uncertain yet undoubtedly more challenging than any of us can remember

As I thought about whether my reflections might still have value for you now, I realised that, over the next few months, the agency will need your leadership more than ever.

You’ll face challenges unlike any that I experienced in the role, so if any of what I learnt in the last four years is useful, then this letter will have helped you just a little bit in your own leadership journey.

After much reflection, writing and editing, I’ve think there are ten lessons that I take away from my time in the role and that I hope you’ll find useful as you settle into your new role:

Lesson 1: The context for leadership.

I realise now that the contextual nature of leadership styles is more important than I realised four years ago. Different phases of the agency’s transformation and growth over the past four years have required different types of leadership.

At times, an enabling and facilitating servant leadership style has been the best way to help our journey – indeed early on I wanted to make this the default mode in which I operated.

But there have also been other times when a more directional style was needed. Sometimes these have been time critical interventions – where I felt we weren’t properly addressing a challenge we faced – while at other times a more hands-on approach was needed to radically refocus and pivot our direction.

There have been moments when I needed to be a transformational leader, driving through major and rapid change. While in other situations I’ve tried to be a coaching leader, helping others grow and develop, building capacity for the agency’s future and enabling others to fulfil their own personal development goals.

I came to realise that being able to recognise and adopt the most suitable mode of leadership for a particular time, challenge of context was a skill in itself. I learnt to do this deliberately and thought often about how to manage myself to be a contextually relevant leader.

Lesson 2: The influence of leadership.

Influence is a tool that I learnt to use wisely in business leadership. I learnt to think about the different ways that I influenced what happened in the agency and be deliberate about the choices I made about how to use them.

While having a job title like Managing Director gives a degree of legitimate influence, I’ve tried to minimise my use of this. But I also realised that it’s very easy to think you’re not deliberately using the influence that your role has, yet my words and actions carried influence with team members even when I was trying to minimise this influence.

I tried to reduce the direct influence I had on the business through reward and coercion – the ability to encourage behaviours through positive incentives alongside negative consequences for undesirable actions. I did this as I wanted to create a transparent system that used behavioural psychology to help people take their own decisions that aligned with the interests of the business.

This was an important part of creating a self-organising culture that was focussed on individual and collective success. I also felt strongly that my own hidden biases could risk the unfair use of reward and coercion, so I should minimise the times I had to use this influence directly.

Later in my tenure in the role, I realised about the expert influence I had. This source of influence was based on the knowledge I had of the agency Tim and I developed and from the work I’d done with our clients. You may not realise it but you go into the role with a unique expert influence based on your career to date and I encourage you to continue to develop that influence for the benefit of the agency and you professionally.

The influence through the information I had and shared as Managing Director was often an interesting conundrum. My instinct has always been to be as transparent as possible – that’s why we share so much information as openly as possible at Deeson. I wanted this as I felt that our team members could take the best decisions possible with the most information possible. I also recognised that what and how I personally communicated information had a significant impact on the way people in the agency felt and acted.

But on the margins, there were sometimes things that I chose to share that didn’t have the influence I expected. The consequences were unintended and sometimes damaging. I realised that information is only useful with the right prior understanding and if it affects choices that people can make.

For example my initial instinct on sharing information about how the agency was performing financially was to share full management accounts. Yet I soon realised that most people don’t know how to read a set of accounts (and nor should I have expected them to).

Instead it was better to present a summary of the monthly financial accounts, alongside a narrative that sets the numbers in context and suggests what those numbers mean for the decisions we want people to make in their day-to-day roles. Information without understanding and interpretation can have unintended consequences.

The last type of influence that I felt I achieved after a while in the role was referent. I realised that through careful and thoughtful use of interpersonal skills, I could shape the work if the agency without obvious and directional intervention. In a service business that’s so dependent on the team members for its success, this is the form of influence I wish I’d worked harder earlier to develop given the impact it had.

Lesson 3: Personal vulnerability is a good thing.

When I started the job I put myself under pressure to always know enough to have the answer to every question that came up. But it was mentally exhausting and, I realised after a while, doomed to failure as I could never expect to know everything about the agency.

It’s OK to not have all the answers and be open about that. I hope doing that made me more human and approachable as a leader in the team.

As my confidence in the role grew, I started to be more open about some of the challenges I faced in the role and drew more visibly on experiences I have had in previous roles and in life more widely. I hope this helped shape a more open and contributive culture that showed other people it was a good thing to share things that in the past we may not have previously talked about at work.

Lesson 4: Build and iterate “the system”.

I ended up looking at the job of running an agency in two ways. We needed to find a system for getting stuff done to achieve our goals and then we needed to help people be effective fulfilling their accountabilities within this system.

The system is never perfect and never finished – as the agency is always adjusting to the world around it. But we kept iterating and improving, building on our learnings about what worked and what didn’t.

This approach led me to recognise when I was working on improving “the system” and when my work was to help people do their best work within the system. I became deliberate in my separation of these two domains of work as a Managing Director.

This way of thinking helped me be clear what problems I was trying to fix or what I was trying to make better – and therefore the best ways to approach that.

Lesson 5: Break big problems into smaller ones.

Early on, I had a habit of getting stuck on how to solve big problems.

The interconnected nature of the agency system meant that it was all too easy for me to end up unsure how to address an issue. They seemed intractably complex. Or I found myself coming up with potential solutions that were disproportionately large compared to the problem I was trying to solve.

My learning here was that once I thought I had a decent understanding of a problem and its root causes, I then needed to break it down into the smallest constituent parts before I attempted to solve the problem.

This helped make sure that the solutions were more likely to be practical and achievable. It also helped decouple solutions, reduce dependencies and increase the pace of improvements.

I learnt lots of small improvements was better than large monolithic improvements that never quite got fully implemented and ran out of steam as the next big challenge inevitably came along.

Lesson 6: You end up with the trickiest problems.

The way the agency system at Deeson works gives people in every role ownership of a lot of how they do their work. That’s by design because I believe it increases engagement and allows people to thrive professionally.

What it means for the Managing Director is that when an issue lands with you, it’s usually because it’s not like one that anyone’s seen before. Your to-do list will end up being filled with the trickiest, most complex problems.

Earlier on I used to worry that this was because there were lots of problems going on across the business, but then I worked out that it was simply a logical result of the way we have empowered teams that can solve the vast majority of problems very capably themselves.

Lesson 7: Being MD can be a lonely mission.

This one affected me a lot in the early days.

As Deeson was my first role as a Managing Director, it’s the first time I’ve really been fully accountable for the ultimate performance of a business. Previously there’s always been someone else above me who held that accountability.

I welcomed the responsibility, but hadn’t realised how when things were hard, I was the only person who had the overview of the whole business and had to come up with solutions.

That said, I was extremely well supported by Tim, my predecessor in the role and the previous agency owner, my leadership team and the informal network of agency peers I’ve been lucky enough to get to know.

You have my commitment that while I’m moving to a non-executive director role at Deeson in due course, I’ll always be available for you for advice, guidance or just someone to have a chat with.

That last one is something I really valued in my relationship with Tim. Moving into the MD role your relationship with your previous peers changes. However much you try to avoid losing valued relationships with team members, the fact you’re the Managing Director means relationships will change.

Lesson 8: Evaluating the future, three moves ahead.

I’ve spent a lot of time looking forward.

Time spent thinking about scenarios, permutations, possibilities and curved balls is time well spent. That goes for growth and transformation as much as it does for more negative scenarios too.

In particular I’ve focussed on trying to think ahead beyond the immediate obvious next step. Like in a game of chess, what might the options be in two or three moves time? What options might the decisions that the Managing Director makes now open up in the next year or two?

None of us can predict the future at the best of times, let alone now. But I tried hard to develop scenario planning skills so that at least I was prepared for the range of options that might present in the future, rather than being blindsided by an unexpected situation.

I won’t pretend I always called it right, but the analytical thinking about the future helped me deal with those unexpected twists and turns when they happened.

Lesson 9: Always have a plan B.

Linked to thinking about future scenarios, I always tried to make sure I had a fallback plan or an exit scenario for any big call I had to make.

It’s inevitable that we’ll all make mistakes in big decisions and I learnt to accept that reality. But I found it’s how we recognise and deal with those mistakes that makes the difference.

I found that thinking about what a flawed decision might look like and thinking about what I’d do if things didn’t work out well helped me a lot. It helped me make better decisions and helped me pivot rapidly if I got the first decision wrong.

Lesson 10: Be yourself, not a stereotype.

When I took on the role in 2016, I had a mental image – a stereotype I guess – of what a Managing Director did. My image of how the role should be done was shaped by my predecessor, by the good and bad leaders I’ve worked for previously and by a whole bunch of other external influences too.

But I soon learnt that trying to be that stereotype was a mistake. I learnt that authentic leadership could only come from me and the way I wanted to be as a leader. So please never try to be me in the Managing Director. Be you. That’s who we want you to be.

Be kind to yourself and recognise it’ll take time for that authentic leadership style to emerge and for you to be comfortable with that. Looking back I think it took me at least a year in the role before I felt confident with the role and my interpretation of it.

So having reflected a lot about my experiences over the past four years as Managing Director at Deeson, those are the ten lessons I’ll take away from the experience. I sincerely hope they help you in your journey over the coming months.

While moving on for me is inevitably a mix of sadness and excitement, it’s the right time for me to take on new challenges and I’m really proud that you’ll be taking on the role. You’ve already been part of the agency’s ongoing transformation since you joined us two years ago and I’m very confident you’ll be a success leading the next phase too.

I’m sure there will be some challenges ahead that neither you nor I expected us to be facing in 2020, but I’m looking forward to working with you and my fellow board member Tim Deeson to help the agency through the next chapter in its long history.

With my best wishes,


I work with technology-centric businesses as an interim Chief Operating Officer (COO), consultant and advisor. I created the B3 framework® for scaling technology businesses and I write a newsletter called Build for leaders who are building brilliant companies.