Coaching and mentoring

Excelling as a Chief of Staff

I help Chiefs of Staff at every stage through coaching and mentoring.

Wherever you are in your Chief of Staff journey…

Whether you're about to start your first Chief of Staff role, navigating the complexity of the first few months, or feeling a bit stuck after being in the position for a while, you're not alone. The Chief of Staff role is unlike any other – managing competing priorities and high-stakes decisions with limited authority but unlimited accountability.

Perhaps you've just landed the position and want to hit the ground running and navigate the politics, the ambiguity, and the volume of expectations. Maybe you’re struggling with impostor syndrome. Or perhaps you've been in the role for months or years, but feel like you've hit a plateau, questioning your impact and wondering how to elevate your influence.

… I understand because I’ve been one.

Having served as a Chief of Staff myself, I understand each of these stages. I know what it feels like to navigate the delicate balance of influence without authority, to be the person everyone turns to when things get complicated, and to quickly develop cross-functional expertise and credibility - all while working for a demanding CEO and battling my own impostor syndrome

Through our work together, you'll gain clarity on where you add most value, develop the resilience to handle high-pressure situations, and build the authentic leadership presence that makes you indispensable to your CEO and organisation - as well as to set yourself up for your next move post-COS role.

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Invest in your growth through Chiefly coaching and mentoring programmes that can be arranged privately or covered by your organisation.

Programmes go beyond the screen: live sessions are paired with reflective prompts, and tangible tools you can see, use, and act on — all designed to slot naturally into a busy life.

Accelerate

For new Chiefs of Staff who want to land well and make early impact.

Address any limiting beliefs before they surface in a new setting
Navigate any early challenges and avoid missteps
Build authority with senior stakeholders in your first 100 days
Accelerate ramp-up time via COS-specific mentoring
Establish systems and relationships

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If you’re an aspiring Chief of Staff, the readiness report is for you! It’s a browser-based guided assessment across core Chief of Staff competency areas. You get immediate personalised results and a tailored set of resources you can use to close any gaps.

Check it out

Refine

For experienced Chiefs of Staff seeking renewed clarity and impact.

Step back from day-to-day pressures and gain fresh perspective on your scope and future opportunities
Reflect on highs, lows, challenges and wins
Jointly note any evolution in aspirations and preferences
Proactively craft action plan for eventual transition to an increased remit or a new role

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I leave my coaching with Poppy with three things: knowledge, confidence and insight. Poppy clearly knows her stuff, having "been there, done that" as a Chief of Staff before. She has a natural, empathetic and encouraging style which worked well for me. We unpacked multiple different topics during our coaching and these were always supported with helpful follow up resources. I feel much better prepared to continue in this role having done the coaching.

Chief of Staff, scaling fintech
I started our mentoring unsure about the role I was playing at my company, with an idea about what I wanted to become, but unclear on how to get there. By the end of sessions, I now have the role I wanted, which is a serious upgrade! I'm grateful to have had the chance to speak to someone about being a CoS, especially the vagueness and sometimes isolated nature of the role. It's an uncommon experience that most of my peers don't really understand - I'm sure any Chiefs of Staff out there can relate to this! It's certainly grounding to have had someone with that shared experience that I can discuss things with.

Chief of Staff, edtech
Poppy was a brilliant sounding board and helped me understand the nuance of the role and how my experience thus far fed into the key strengths I could bring to the role. She really helped build my confidence, and helped me structure my thinking. I would highly recommend Poppy. She's super smart, calm and a very steady presence who really helped me navigate my strategy.

Senior manager, FAANG
I really liked Poppy's approach of combining coaching and mentorship, meaning we could have more structured coaching-style conversations which could also pivot into direct advice and reflections from her time as a CoS - which was exactly what I had been hoping to achieve. Our sessions have given me a much stronger foundation of self-belief and a practical framework for reflection, learning, and celebrating wins. These changes have become part of my day-to-day routine and have had a noticeable impact on both my output and the quality of my headspace. More broadly, the coaching has helped me approach CoS challenges with greater confidence, which has positively influenced how I work and lead.

Chief of Staff, medtech
I saw value in getting coaching because I knew there was more to achieve than the tasks set for me by my principal. I enjoyed that when Poppy gave advice it was powerfully quiet. Through our sessions I discovered listening not only as a skill but as a superpower that I have the privilege to wield whenever and however I want. So much was gained when I identified that confidence and power is just as attainable when I sit back and let others have the floor. I also found it helpful to work towards a picture for what I want next, even if that means leaving the role of CoS.

Chief of Staff, strategy consulting
I would say to current and past Chief of Staffs that this is a unique opportunity to work with a coach who really deeply understands this odd role, its upsides, its challenges and how it can play out within a professional career. I found that Poppy's questions and our discussions were thought-provoking and allowed me to explore in some detail how my past experience in the Chief of Staff role could inform my future decisions. This series of coaching sessions was basically a gift to myself at a time of significant transition both personally and professionally. I landed on some solid decisions I was comfortable with regarding my immediate career, and also took away some impactful work we did on the details of how I present my experience - for example, the tension of presenting a role that is by its very nature a 'backstage' role in a world that expects one to claim individual credit in job applications. We also worked through some important tensions between career and lifestyle that had emerged due to my family circumstances; she gave equal weight to my professional ambition and my other desires for my life.

Chief of Staff, higher education institution

Here’s where Chiefs of Staff get to through our work together:

Clarity on your role and how you want to show up in it.
Clarity about yourself. This is the foundation that everything else builds on.
Gravitas isn’t just for CEOs and statesmen. It’s a superpower that will help you influence, communicate and lead.
And it can be learned! Whether you want to excel in your first few weeks as a COS, or as you transition out of the role, executive presence will be your superpower.
This role isn’t just about the soft skills - you need to hone your strategic analysis and synthesis muscle too.
We’ll make sure you’re confident in all the key areas, and that you know how to make AI work for you.
This one is ultra important. I appreciate it’s hard to make time for your own ‘self care’, but we’ll talk about why it matters and equip you to prioritise it.

Sound good? Let’s chat about how coaching could help you unlock your potential in a way that feels authentic.

Let’s Chat!

I support Chiefs of Staff at every stage in their journey.

Book a free introduction call