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Dominic Monkhouse Resource ProfileAuthor: Dominic Monkhouse

You’re the CEO of a fast-growing business. You’ve assembled a high-performing leadership team with energy, ideas and vision, but you’re finding it hard to hold them to account. That’s not unusual. Many of our clients are great at strategy, but execution and attention to detail aren’t their strengths.

Many of our CEO clients have dyslexia and or ADHD. I am dyslexic. This neurodiversity might be why they are in the 5% of the population that starts companies as entrepreneurs. It’s a feature, not a bug.

CEOs face the dual challenge of executing strategies effectively and managing a high-performing team in business management. This necessitates proven success in business management roles that emphasise executive-level advising and interdepartmental collaboration.

In many smaller businesses, executives often lack adequate support for themselves or their teams. Are you wondering how to bridge the project management gap? You might be considering hiring an Executive Assistant or a Chief of Staff. Let’s differentiate between these roles to provide clarity.

What is an Executive Assistant to a CEO?

An Executive Assistant will get in front of you daily, managing your diary, coordinating appointments, taking messages, arranging travel and fielding your inbox. You may think this sounds like a PA. But there’s a difference between Executive Assistants and Personal Assistants. PAs will mainly stick with repetitive tasks and take inputs to generate an output. An EA will provide high-level administrative support, doing things you’re not good at. As such, they can help you be more rounded in your role. They’ll give you more reach.

When I had an Executive Assistant working for me, I often attended back-to-back meetings eight hours a day. Sometimes, things would arrive in my inbox that needed to be sent on or actioned. My EA acted like an extension of me—they knew what I was likely to say or do. This is a step up from the PA. They were thinking for themselves, using their initiative and, rather than waiting to be told what to do, finding the things that would add the most value.

    At Peer 1, our CEO and CFO shared the same Executive Assistant, Linda. It really helped with coordination. Diaries were in sync, and Linda could keep both parties informed on the others’ activities. And if Linda had any spare capacity, she offered it to the rest of the leadership team. She was great at working out the relative priorities of things. If it were urgent, she’d find a sliver of time in the right diary, moving things around so that you got the time you needed. Our time was well-optimised by Linda!

    What is a Chief of Staff?

    A Chief of Staff will act as your right-hand, strategic partner, collaborating closely with executive team members. They’ll use your authority for project management, create strategic plans for special projects, and oversee operational aspects such as finance, human resources, and risk management.

    Crucially, a Chief of Staff can act as your eyes and ears in the business and industry, playing a pivotal role in developing and implementing operational strategies alongside the CEO to promote company culture and success. They are solely focused on your success.

    What is the difference between Executive Assistant and Chief of Staff?

    If you employ a Chief of Staff, you’re handing over part of your role. A Chief of Staff will work alongside senior executives, attend executive meetings, organise strategic project information, pull together papers, and ensure all the OKRs and KPIs are on target. An Executive Assistant role is more likely to backstop you from your desk.

    A Chief of Staff will speak with your authority and act as an extension of you. You’ve effectively doubled your capacity by taking them on because another human being with your voice works eight hours a day in your business and industry. Your Chief of Staff is not a competitor and the strategy will be left to you. Instead, they can act as a sounding board and they’ll focus on execution and deliverables, keeping everyone else in the Executive team on track.

    The key skills necessary for a Chief of Staff include a blend of hard and soft skills such as advanced communication, organizational abilities, administration, leadership, and a strong sense of diplomacy, distinguishing their role from an Executive Assistant.

    What qualifications do a Chief of Staff or Executive Assistant need?

    This is all about playing to your strengths as CEO. And recognising where you have gaps. We use a nifty tool called Working Genius, designed by Patrick Lencioni, to help us recognise our clients’ teams’ unique set of geniuses. If you’re a typical CEO, your qualities are likely to be on the left-hand side of this chart, firmly in the strategic area. These working geniuses are Invention and Discernment.

    A good Chief of Staff or Executive Assistant will have the geniuses of Enablement and Tenacity, which are firmly on the right-hand side of Working Genius. They’ll be born organisers and facilitators, good at following through and galvanising others to stay on task.

    To be an effective Chief of Staff, you also need a higher-level understanding of strategy and its formulation. In some of our clients, this comes from an MBA or similar qualification and industry knowledge.

    Can you move from Executive Assistant to Chief of Staff?

    In a word, yes. A tour of duty as a Chief of Staff can be a great career path for an Executive Assistant. It’s an opportunity for career growth and for bright talented people to move up to C-suite level. In some organisations, Chief of Staff is a career path for mid-level managers with the right capabilities and industry knowledge to advance into a leadership position. They can see how strategy gets made, how it’s executed and what the view is like from the top.

    It’s a great way to dismantle silo thinking. Exposure to the Executive team lets a Chief of Staff see how things get done and what makes the organisation tick. Ensuring the quarterly strategic reviews and weekly team meetings happen, the career growth of a Chief of Staff is pivotal in the successful execution of strategy.

    What does your leadership team need – a Senior Executive Assistant or a Chief of Staff?

    So what do you think you need? It depends. What size is your business? And what complexity of change is it facing? If you’re a business that’s standing still and is broadly the same as it was 10 years ago, do you really need support?

    Most of the organisations that we coach are on a fast-growing trajectory. So there’s lots of change and moving parts. Sometimes they need both an Executive Assistant and a Chief of Staff. Someone to backstop the CEO’s diary/email and then someone to support the strategic initiatives, OKRs and tracking.

    You might need some due diligence to be done. Perhaps there’s more detail than you can cover in a daily huddle or weekly meeting. 1:1s need to happen around OKRs, and resource allocation needs sorting. Here, a Chief of Staff is worth their weight in gold.

    Because of the geography of your business, you might be travelling for long periods. A CEO’s role can involve speaking to partners and customers in different time zones. Business development, demand generation or customer loyalty can swallow up time leaving very little capacity. So employ a Chief of Staff to stay back at the office all day, every day. They’ll make a huge difference to any conflict management, ensuring your Executive team are on top of the things they said they would do for the quarter. Your time can be focused on where it’s needed most.

    Identifying gaps in your Executive Team

    Maybe your leadership team is more execution focused. If that’s the case, then a Chief of Staff or Executive Assistant are not what you’re looking for. Because your team is devoid of strategic skills, your problem is innovation and staying close to your market. This is common in tech firms and you’re going to need to go out and find a Chief Product Officer to deliberately engage with customers and go looking for problems to solve.

    We discuss our clients’ issues and help them identify gaps in their teams. Once identified, we discuss how we’ll fix them. Helpful to this is working through a job scorecard and success criteria for the needed job description.

    Planning for the inflection points of growth

    There’s a contextual thing to add here – something I say to CEOs all the time. As they grow, businesses hit inflection points or growth traps where, without proper planning, they can get stuck. In smaller businesses, that first valley of death is at roughly £1.5 million. A solo entrepreneur gets to 12 employees and reaches the limit of their span of control. They hire a person. They lose a person. They win a client. They lose a client. On it goes. It’s a cash/execution spiral.

    So they start to need executive support – perhaps in the form of an Executive Assistant. They hit the next inflexion point at 30 staff when people stop putting their cups in the dishwasher and defining culture becomes more important. To get past this, they need a fully functioning Executive Team. Once they reach 100 staff – bam, they hit the next growth trap where a new management layer is needed below the Executive team. A Chief of Staff can help enormously with the running of this new team.

    My advice to clients, whichever point they’re at in their business, is to look at the things that only they can do, define those things, and then work out the other stuff that can be delegated. Maybe that’s when you decide to take on an EA role or Chief of Staff (or even a Chief Operating Officer). It could be the best decision you ever make.

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    Written by business coach and CEO mentor Dominic Monkhouse. Read his new book, Mind Your F**king Business here.

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