Navigating Midlife career shifts (Part -II)

8 min readJul 10, 2020

Part II — Spending a day in the Wonderland

This blog is a continuation from my last story on this topic which can be read here. In this story, I will try to go a little deeper into the execution details of this role.

Day in the life of Alice — The Responsibilities

First things First, understand “Why you are Hired”. Time is the most precious resource for an executive you are serving. Contribute such that executive can scale. The following can be some key reasons why executives hire an assistant.

• Get execution done on various strategic, tactical, and operational initiatives & objectives.

• Help the executive to keep a track of initiatives spawned, by making sure that weekly, monthly, and quarterly reviews & planning exercises are conducted on-time.

Substitute the executive in meetings which he can skip but would like to be updated about
Acting as the sounding board for new ideas and initiatives
Understand that each executive has a “Style of working”
Executives are visionaries, they have larger and long-term goals in mind
Every executive has his/her unique style of working. Discover, Understand and then adapt to those
My boss says, “I don’t care where you work and when you work, what matters is the results” What and when you deliver is important
Executives mostly do not like a PowerPoint presentation for a meeting — what they prefer is a story a context and more time to discuss the next steps. Be Crisp, jargon-free, and use tools like mind-maps to keep conversations short and productive.

• Executives like to work on collaborative ideas that are energetic and rechargers. This means it takes sometimes offline to streamline by working behind the scenes.

We can summarize the type of work by two methods which can give a high-level idea of what needs to be done. One needs to keep juggling around these often by wearing different hats.

The Buckets of Contribution

The contributions you make day to day are very unstructured in this role. It’s hard to compartmentalize those. However broadly you will find yourself juggling around in these three buckets.

People: Understand the pulse of internal teams across the software delivery business units and departments (sales, marketing, finance, IT, etc.). Check where they need help, approvals, or assistance from the executive you are serving and act as an interface between the teams and your manager. Ease up and speed up the value chain by being the face for the leader.

Processes: Understand the key processes and policies in the organization and contribute to corporate processes. Some of these can be the planning process, budgeting process, finance reviews, board meetings, internal communications, marketing processes, IT processes, and similar cross-functional routine initiatives.

Portfolio: The executive you are serving would be leading several projects — both internal and customer-facing. Expect these projects and programs to be cross-functional, cross-domain in nature. Contribute towards tracking those to ensure trains run on time and the objective for your leader is rightly taken care of.

The Buckets of Execution

This can be looked up as following three key areas of contribution

In terms of the execution of your role, expect to work in the following key areas. The amount of time you put in each bucket will vary depending on which leader you are serving and the nature of his current role. For example, in my case, Dr. Anand was more focused on the Strategic part of it during my tenure.

Strategic: A true visionary leader will be always focused on the Company’s forward-looking strategy. This can be a new business idea or a technology roadmap and prediction. These initiatives are complex and long term. Our job as a TA is to:

· complement leaders’ vision by providing required resources

· research on a given topic and providing a summarized understanding

· act as a sounding board to the ideas of your leader

· providing the ability to make decisions through data gathering, information analyzing and presenting considerations from other stakeholders

· offer an independent point of view that challenges and offers different perspectives, offer appropriate reasoning as required to validate the strategy

· attend key meetings with sales, marketing, delivery, and board to understand the company vision

· contribute to growth and solutions, CTO and strategy teams

Tactical: Some initiatives would be tactical, medium-term in nature. These can be technology projects that the leader is driving to create new offerings, projects where the sales team would require help from the leader to make connections to prospects, projects where the marketing team would like to validate a branding or digital strategy initiative, etc. The TA needs to:

· keep track of each initiative and ensure that teams are free of bottlenecks

· aid teams in decision making and prioritization

· orchestrate across functions

· project manage the initiatives — make things happen

· writing first drafts of communications — mostly internal

· contribute to company quarterly and yearly activities like annual reports, annual general meetings, investor meet

· working behind the scenes

· contribute to RFP’s and proposal presentations preparations

· contribute to drafting the solution offering for a new idea

· assist in budget, sales and marketing planning meetings

· contribute to data gathering, drafting, reviews for the annual report of the company

· serving as the primary communicator between the executive and other staff, clients or key partners and stakeholders, and facilitating communications.

· articulating the executive’s objectives, ideas, concerns, ideas in an effective and efficient way

In addition to this, the executive is constantly getting requests for their time, money, approvals, guidance. We need someone who can first vet the ask and respond to these requests appropriately. Protect the leader’s time, taking unnecessary conversations off their plate. Such kind of gatekeeping activities falls under the tactical bucket. This requires a high degree of understanding and trust between the TA and the executive.

Operational: Certain activities can be repetitive and mundane. One needs to understand the company processes and timelines to help the leader fulfill these. The weightage and nature of this will vary depending on which executive you are assisting. We may find more of this for the CEO and COO executives and comparatively less for strategic executives.

Example the TA can contribute to projects and meetings in the following way:

· prepare the agenda for the meetings

· act as a proxy when required in meetings

· take notes and keeping track of action items

· create presentations and consolidate case studies

· organize and represent in business review meetings

One needs to be constantly aware of the fact that our presence does not introduce the addition of inefficacies, hierarchies, redundancies, or create a lack of clarity. Rather your strong communication skills, operational excellence, and strategic thinking should help the executive navigate the complexities and maximize his bandwidth.

Beyond these buckets, there is one type of work that deserves separate attention. Technology conferences, investor meets, interviews, panel discussions, and talks form a large part of what your leader does.

The TA works with the executive on defining the presentation outline, gathering key data points, and graphics that the executive wants to present. They coordinate with the conference organizers both in advance of the conference and on the day-of to make sure everything is properly set up. They also coordinate with the executive assistant to make sure travel goes smoothly, and they have a backup copy of the reservations along with all relevant contact information. The TA helps arrange for the executive to hold a few key meetings at the conference and has prepared a pre-read brief on each meeting for the executive. Most of these talks end up spawning a project or initiative that needs to be worked upon with the conference stakeholders. TA later needs to carry forward these initiatives to completion.

Attending these conferences gives an amazing opportunity to network with the stalwarts as well as learn the point of views and trends for a given domain.

Skills Required

The relation between you and the executive is strongly based on mutual trust. An individual should have the core values of integrity, loyalty, and respect for the leader to play this role effectively.

This role may be rotational depending on how your organization and the leader have defined it. It’s good to possess the following attributes and capabilities if you are thinking of taking up a similar role. This is above and beyond the deep technical skills, sales, and business acumen that one must have gained in the industry experience so far.

Organization skills. These types of positions demand invariable planners. At the same time do remember that people we support are visionaries. They are usually not management or administrative professionals. Hence have a plan, but don’t expect things to go by the plans. Expect last-minute changes and have the flexibility to accommodate those.

Communication skills: People who are hired for this position need to be skilled at networking because landing one of these jobs often involves having very powerful people around you. Leaders should respect your talent and professionalism. Having good writing skills with different styles will be helpful.

Performance under pressure: Works well under pressure and can handle stress well

Work flexibility: Maintains a flexible schedule and meets the executive schedule requirements

Interpersonal skills: Maintains a good working relationship with the executive, staff, and constituents

Decision-making ability: Maturity to decide and differentiate between strategic and tactical decisions on behalf of the executive. Ability to distinguish when to seek help and when not take the control

Above all being deeply passionate about the work, having a learning mindset, and being respectful for the leader you work with is the key.

Some Misconceptions

The role is often confused with the Executive Assistant Role. The nomenclature of this role may vary across organizations. Also, no two TA roles can be the same. Few differences to highlight that can help give a perspective.