Skip to main content


You’re 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 strength.

It constantly amazes me how often I work with clients in smaller businesses with no support for themselves or their Executive team. Perhaps you can see there’s a project management gap, but you’re not sure what you need. Possibly an Executive Assistant? Or a Chief of Staff? Let’s get clear on the difference between them.

What is an Executive Assistant to a CEO?

An Executive Assistant will get in front of you every day, 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 the things that 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 was often in 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 the 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 was able to 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 was 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. 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. They are solely focused on your success.

    What is the difference between Executive Assistants and Chiefs of Staff?

    If you employ a Chief of Staff, you’re handing over a part of your role. A Chief of Staff will work alongside senior executives, attend executive meetings, organise strategic project information, pull together papers, and make sure all the OKRs and KPIs are on target. An Executive Assistant role is more likely to be backstopping 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 there’s another human being with your voice working 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.

    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 the unique set of geniuses in our clients’ teams. 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 how its formulated. In some of our clients, this comes from an MBA or similar qualification along with 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 who have the right capabilities and industry knowledge to move up 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. By exposure to the Executive team, a Chief of Staff can 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 talk through the issues our clients are facing and help them see the gaps in their teams. Once identified, we talk about how we’re going to fix them. Helpful to this is working through a job scorecard and success criteria for the job description that’s needed.

    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 inflection 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. 

    Author: Dominic Monkhouse

    Overcome the challenges stopping you from reaching your full potential. Learn more about...

    Written by business growth coach Dominic Monkhouse. Find out more about his work here. Read his book, ‘F**k Plan B’ here.

    Receive Dominic Monkhouse’s expertise in your inbox every week

    Sign up today and get your copy of F**K PLAN B: How to scale your technology business faster and achieve Plan A, the book that will change your business and your life.

      Receive Dominic Monkhouse’s expertise in your inbox every week

      Sign up today and get your copy of F**K PLAN B: How to scale your technology business faster and achieve Plan A, the book that will change your business and your life.

          Discovery Call | Business Growth Strategy Session

            Enquiry | Scaling Up Master Business Course