Inside leadership’s most underrated partnership

A show hit television screens in 2011 that has stuck in the cultural zeitgeist ever since. Harvey Specter quotes are still widely shared on social media for hustle inspiration, as the suave lawyer became revered in the legal drama Suits. However, for all Specter’s dapper three-piece outfits and slick comebacks, it was another character who stole the show and many viewers’ hearts: his legal secretary, Donna Paulsen.

She redefined what it means to be an assistant – acting not just as support but as Specter’s trusted adviser, strategist and moral compass. Paulsen joins a long line of assistants-turned-indispensable assets in pop culture, from Andy Sachs in The Devil Wears Prada to Waylon Smithers in The Simpsons.

Sidekicks have come a long way from being associated merely with making coffee and managing calls. Today’s executive assistants have the potential to be a powerful growth lever, connecting the organisation while protecting a leader’s time and focus. Key questions are when to hire an assistant, how to set up the relationship for success and how to use their expertise to boost productivity.

Lucy Brazier, author and CEO of Executive Support Media, cites Jeff Hoffman, the Booking.com co-founder, who said: “If you don’t have an assistant, you’re your own assistant.” Brazier has developed a skills matrix for the administrative profession now used by more than 13,000 global companies, work that earned her an OBE in 2021.

She believes that an executive assistant (or similar role) can be a gamechanger for a leader. But with 160 different job titles to pick from, choosing the right role and the right person isn’t simple. She challenges leaders not to think of the title, but the function.

This is echoed by Marianne Whitlock, co-founder of Strategic PA Recruitment. One of the biggest errors leaders make is hiring an assistant based on a checklist of skills. “It has to be more than a skills match,” says Whitlock. “It’s about honesty, transparency and chemistry. The leader and assistant must want to work with each other. Otherwise, it doesn’t work.”

Sir Richard Branson once described his assistant, Helen Clarke, as “his memory”. She attends his meetings, jotting down verbal commitments and noting items that would affect his calendar and productivity. But a deeper view shows her analysing the body language of participants and identifying where she could add value – from building relationships with those around the table to detecting problems before they arise. But this proactive approach only worked because Branson empowered her to act.

“Executives aren’t trained on how to use the assistant,” Brazier says. “When I train executives and leaders, the first thing that I say to them is, ‘Do you know why the organisation employs an assistant?’ They quite often look at me, blink and go, ‘Well, really, we haven't thought about it.’ I say, ‘They’re there to give you back time.’ Simple economics says that if both you and the assistant can do something, it should be the assistant doing it, because you are paid your big bucks to go and do other things.”

Her advice is to make an assistant your first hire. “The average executive spends around 58 per cent of their time on email. If you have an amazing assistant with a triage system, it’ll take that down to 12 per cent. You’re getting back 46 per cent of your time immediately. I think the question is not ‘Can you afford it?’ But rather, ‘Can you not afford it?’”

“The work that a leader can get done if they have the right person on their side is exponential,” says Sarah Howson, also of Strategic PA Recruitment. “It’s almost one person operating with two strands to them. But the leaders who value the position and understand how impactful an assistant can be often include them as part of the senior leadership team.”

There are number of pitfalls those hiring an EA often fall into. First is hiring for skills, rather than chemistry. A misaligned personality or working tempo can create tension and inefficiency.

Second is a lack of clear boundaries. Expectations around responsiveness, working hours and decision rights need to be established so confusion does not set in. Which leads to the third pitfall: when leaders try to bypass their assistant or override their decisions, or when others in the organisation do. Everyone has to respect an assistant’s decisions for the role to work.

Fourth is not giving assistants a stake in the outcomes, leaving them in a gatekeeper role that is ineffective. And fifth is failing to invest in the relationship through regular check-ins, feedback and shared reflection.

Leah Fitch is the executive assistant to Alex Stewart, the CEO of the frozen organic food producer Pack’d. She joined the scaling company in 2022, and her “number-one task was to identify what Alex was doing that I could take away from him, so he could focus on business-critical tasks”. Since then, her role has expanded to cover much more than the original job spec.

Outside of inbox and schedule management, she also plays the role of HR lead, office manager and operational problem-solver. She stepped in to manage systems and audits as the company grew, creating a buffer until someone could be hired to take over. She describes herself as the glue that keeps things running between leadership, staff and suppliers – at one point even driving to Heathrow Airport to intercept stock coming in.

Joanna Allen joined ice cream challenger Little Moons as CEO in 2024. She had assistants in her previous roles and notes that people drawn to this career recognise the importance of their contribution to a team’s culture, as much as its productivity. Her executive assistant at Little Moons is Amy Callaghan, who, she says, “has more than a singular impact” on her productivity – “rather the sum of a hundred little moments”.

“Whether it’s knowing that Amy’s got an eye on my inbox and Teams channels,” says Allen, “or that she’s managing my diary to ensure the most important connects are getting my time; grabbing me lunch so I stayed fuelled and productive for remainder of the day, or planning travel for an upcoming visit to one of our international markets – she creates capacity for me that I can use to drive our success.”

Winnie King had a number of roles within the House of Commons, including personal assistant to the director-general. She left in 2021 to become executive assistant to three directors at Mace Group, one of the contractors behind HS2’s redevelopment at Euston. She views herself as a bridge between departments and a protector of leadership time – helping her executives show up at their best. However, her role has also morphed.

“One director is a morning person,” she says, “so I’ll cram everything in the morning and not put any meetings after four. Others aren’t great in the morning, so I leave them to it. You only learn these things as they come up… sitting down and asking, ‘What comes into your inbox? What can I take control of?’ And then building up trust.”

Brazier says when the partnership clicks, one of you breathes in and the other one breathes out. But this doesn’t come without taking the time to build that trust. King says that in her experience, it takes between three and six months really to get to know each other.

Simone White coaches assistants and executives on creating mutual trust and clear expectations. She likens it to a trip to the doctor. If you have an issue, but they seem unsure and pull up Google to check, you immediately lose trust in that individual. “That trust element starts from having the skillset and but also being able to articulate it. When I go into a new relationship, I find out from the leader or executive: what do you want the outcome to be? What are the goals? What are you looking to do? Then after that, it’s consistency of application.”

Without explicitly communicating expectations, you may be missing out on vital productivity gains. Back at Little Moons, Allen has utilised the “trust equation” in her relationship with Callaghan, which is the theory that trust is built through a combination of credibility, reliability and psychological safety.

This was built through small actions, such as agreeing on whether or not Callaghan was alright with being referred to as her assistant, confirming if she was happy to talk business outside of working hours, and empowering her as the gatekeeper of her time and focus to the rest of the company.

Once trust is built, an assistant’s role can expand and come to life. Callaghan says that it’s like becoming an extension of the leader, which has supercharged Allen’s productivity. “I know that she has full trust in me,” she says. “I always jump on emails as soon as I can and clear out all the clutter, while highlighting anything that's super crucial. This allows her to hit the ground running.”

While trust can be built over time, ensuring there’s a chemistry and character match is vital for the relationship. “You’re spending a lot of time with this person,” says Howson. “During intense periods in business, you see everyone’s true colours. You need someone who can operate on your good days and bad days. A personality match is really key, as well as making sure the values align from both sides.”

The right hire is essential. Chemistry is as important as capability, with alignment in pace, communication style and emotional bandwidth also vital. The role has to be strategic from day one, with the assistant embedded in decision-making and introduced to key stakeholders and business rhythms.

Make sure you communicate pain points, not just what needs to be done. The best assistants design systems that solve problems leaders didn’t know they had. Finally, build a trust plan, not a task list, and be transparent about priorities, style and feedback preferences.

Howson and Whitlock set up the boutique agency Strategic PA Recruitment after decades of experience. They’ve provided search services and placed assistants in well-known brands ranging from food and beverage companies to wealth management organisations. The pair spend time getting to know the leader looking for an assistant to ensure a match. They say niche agencies can achieve more successful results than the broad focus and remit of an internal team.

“We deal with this like an executive search because it is a role which directly impacts the bottom line,” says Whitlock. “When we partner with a client and an organisation, we become an extension of them. We’ve become an extension of their brand and their values. But we really understand the role, its nuances and the ins and outs.”

“When an assistant can challenge a leader, ask if a meeting is really worth it, help prioritise and even push back, this shows maturity and confidence,” Howson says. “That’s when you know you have someone strategic on board.”

Setting up an assistant for success can begin even before they’ve officially joined the company. Strategic PA encourage assistants, before onboarding, to immerse themselves in the leader’s world by shadowing, sitting in on meetings and getting to know how they talk and think.

Brazier says that she’s horrified by stories of leaders hiring assistants when they’ve never met. “It’s such a symbiotic relationship,” she says. “If you really don’t get on, it’s as horrific for the assistant as it is for the exec, because so many of them are hugely skilled but they turn up at an organisation and find that it’s stuck in the Middle Ages and they only want tea and typing. That’s soul-destroying for an assistant who is used to pretty much running the office of the CEO. Find a recruiter that really knows what they’re doing.”

Remember the example of Clarke, Branson’s assistant? That’s an example of the all-too-often underused power, says Brazier. “I think most assistants want to be involved. If they sit in those meetings, they very quickly get what’s going on by osmosis. But if they’re not included, they ask if there’s anything for them when the exec comes out of the meeting and they say, ‘I’ll talk to you later.’

“If they were in the meeting, there are probably a hundred things that they could be doing for you. Embed them, and if they understand your goals, then the two of you can work on those goals together. If they don’t understand your goals, how can they possibly work with you to make sure that you achieve them?”

Transparent goals also provide a way to track the impact of a great assistant. Howson recommends identifying North Star goals early. “Is it replying to emails in your voice? Is it increasing the amount of uninterrupted time you have for strategic work? These need to be agreed upfront.”

Measuring success is also important. Metrics include time returned to the leader, decision speed, calendar and meeting efficiency, organisational flow and impact, and leader wellbeing and focus.

Break these metrics down further if needed. For example, time returned to leader can be measured in hours of deep work created, admin time reduced and meetings shortened or removed, while decision speed can be seen in faster responses, fewer bottlenecks and reduced back and forth.

Long gone are the days of assistants being a perk or status symbol wrapped up in a high-powered job. They’re a strategic lever. When an assistant removes friction, filters noise and structures time, they don’t just support a leader. They scale them.

Yet too many executives still underestimate the role, confusing proximity with importance. The question isn’t whether you have someone managing your diary, it’s whether you can, or have, built a partnership powerful enough to change how you lead.