Shadowing Executives: Top 10 Lessons

In this article, we discuss the top 10 lessons learnt during Executive Assistant (EA) roles. The EA role involves working closely with one or more executives, supporting them in fulfilling their responsibilities. It can also be titled as Business Manager or Chief of Staff, and our previous article “Executive Assistant: a worthwhile seat at the executive table?” discussed the attraction of such roles and their drawbacks. It was intended as an introduction for those of you considering a role like this. 

In contrast, this article focuses on learnings from the experience – while a far cry from actually doing the role, we hope these lessons will prove helpful to those who want a crash course.

Lesson 1: Executives are people too
Working closely with executives lets you observe them in their natural habitat, being part of the territory which they are responsible for. And, rather than seeing executives as rulers of the jungle that need to be feared or revered, many executive assistants talk of the personal relationships they form. This regular personal contact underscores that executives are “only human after all” and helps those starting out in their careers see executive positions as indeed attainable – the role model effect in action. Darryn, for example, described his realisation as “[I] stopped idolising management, and started having more open conversations with them. I realised that they rarely have all the answers, and also value input and challenge from others in the organisation”. Another summarised it as “people are people no matter what level you [are] at”.

Lesson 2: Grow who you know
As discussed in our original article, many people who choose Executive Assistant roles do so to gain more exposure in their organisations, and catapult their career. Marcé described this internal networking with this statement: “Relationships with people and how people perceive you are two of the most important aspects of your career” and Jikku shared his learning that “being an effective CEO is not just about internal relationships but also about [your] outside network”. Another described his role as a “great opportunity to build wide relationships in the business”. Being an Executive Assistant has an exponential impact on the breadth of your network, across multiple levels of your organisation, and also with external parties your executive team interfaces with – the key is to keep building and nurturing this cross-profession network once your EA role is over.

Lesson 3: Making decisions
Another lesson past EAs reference is the opportunity to watch decision-making in action. One described this as “how to get things done in a big organisation and how decisions actually get made”. Their collective learnings in this area include:

• the degree and complexity of tough decisions senior management have to make
• the importance of focusing on the support of the overall business strategy when assessing any individual business project, product or initiative
• decisions usually have to be made on imperfect information (even at the very top level of an organisation), so don't waste time obsessing too much about getting the perfect supporting analysis. It needs to be fit for purpose, not perfect.
• the importance of being decisive and making decisions fast in order to keep up with the pace of change

Lesson 4: Leading people
Unsurprisingly, leadership lessons from executives who have years of experience in managing and inspiring others came up regularly too. Shadowing different executives can teach you a lot about different leadership styles, when they work best and when they don’t. Elaine shared her experience of working with a range of executives, reiterating the impact of leaders on culture: “Everyone is different and senior executives must be able to adjust their leadership styles to achieve the desired culture of the business (not as easy as it sounds)”. 

Nimol reflected as follows: “Stay true to who you are, especially when the going gets tough. As you get more senior, your behaviours and attitude will tend to matter more relative to technical competence. You are more likely to make an impact if you remain true to who you are because you will then be authentic and those around you will recognise this, creating trust. This was something I observed as a difference between leaders who inspired me and those who didn't”.

Another commented that he saw firsthand “the power [you have] to make someone feel valued by paying attention to the attention that you give them”. Carl learnt that “to be effective at leading, you need to truly believe in the values of the business and actually express that in everything that you do (no matter how trying the situation). Others will follow”.

Lesson 5: Communication
This lesson was particularly helpful for Executive Assistants who had previously only done technical roles. To underline the importance of communication skills and diplomacy, they gave these tips:

• Know your different stakeholders/audience when presenting an idea or business issues and make the positioning relevant to the specific group e.g. regulators, advisers, financial director etc
• Put effort into telling your story to maximise your impact
• Use verbal hooks to get attention and use “fast framing” to present your conclusions and thinking: when speaking with executives, summarise the outcome to start, and then provide more background if requested

Lesson 6: Adaptability
Nimol shared another lesson he learnt, and described the circumstances as follows: “Things can change in the blink of an eye. I happened to be in this [EA] role during the financial crisis. The company's balance sheet was healthy one month, then had a huge hole the next. The share price tumbled and my boss and many of the exco members resigned in quick succession. So never get too comfortable and keep alert!”

Lesson 7: Getting stuck in
While an Executive Assistant role definitely helps in giving you a birds-eye view of the whole organisation (and its key value drivers), a number of those we asked stressed the value of leaders staying aware of, and involved in, the details. One said “From a broader business leadership perspective I noticed that there are many inefficiencies and that many leaders and their strategy development teams are not close enough to the details of their customers’ journeys. So I guess I learnt that I admired people who got their hands dirty and that is what I have aspired to ever since.” 

Another commented: “Keeping a finger on the pulse in every part of the business can be done, but requires dedicated and succinct lines of communication and excellent time management.”

One summarised his experience as: “Leaders have the responsibility to get involved in the detailed aspects of [the customer experience like] products, including marketing materials and advertising campaigns.”

Lesson 8: Keep asking questions
Those with EA experience also refer to the value of continuing to learn and question, both while in the role, and in your career afterwards. This covers “ask[ing] as many questions as you can even if you feel that it might be a stupid question” of your direct manager, other executives you interact with, and the broader teams you work with as you fulfil the responsibilities of the role. Another echoed this advice with: “Always ask as many questions as you can. It was a great opportunity and I learnt tons, but you only learn if you are not afraid to ask questions and make mistakes.”

​Lesson 9: Self-awareness & -insight
While every role in your career offers the opportunity to learn more about yourself, your strengths and what you are capable of, an Executive Assistant role offers a fast-track way to self-discovery. This is particularly true if the executive you support mentors you, encourages you to reflect and gives you regular feedback on your progress. Specific examples of these insights include:

• I learnt a lot about myself – mainly that I did not want to be a storyteller of other people’s activities
• I realised that I value a team environment more than a solo role
• Always be prepared
• I come across as uninterested and need to speak up more in meetings
• I was able to decide which of the different leadership styles I observed best fit with me so that I could adopt them for myself
• Don't be too big for your boots… Everyone is fallible and everyone is ultimately dispensable to an organisation so be humble and make the most of the opportunity!

Lesson 10: Where to next?
The final lesson from your time as Executive Assistants is the value in reflecting on what you want from your career, often inspired by the big picture perspective on your business and industry, and exposure to new ideas and ways of working. Jikku for example refers to the value for him in “connecting the dots between where I was in my career and where I wanted to be.”

Elaine spoke of the self-insight (Lesson 9) being “particularly useful if [you are] at a career cross-roads and want to explore a range of future options”. 

All in all, the experience can be extremely constructive in empowering you to make a conscious decision about your future career direction, even if you take a series of steps along the way. Combined with the networks you’ve built (Lesson 2), this proactivity can help to get you to where you want to be.

If you’d like support with reflecting on your career goals, and help to take positive steps towards them, please contact us. 

Many thanks again to Elaine Thomson, Willem van Rooy, Nimol Rajkumar, Darryn Padayachee, Jikku Joseph, Abu Addae, Marcé Marx, Carl Blom (and others who asked to remain anonymous) who kindly shared their thoughts and experiences with us as part of our research for this article. All errors are ours.