4 Keys to Leading Today.

Illustration by Lemmywinks via Midjourney

We have entered an age of de-Bossification.

In many industries, particularly “White-collar” ones, the era of “bosses” is in decline.

Less of a clamoring for boss like traits of controlling, managing, measuring, allocating, evaluating and checking in.

There is a rise in the need for leaders and their traits of being guides, coaches, mentors, role-models, creators, pioneers and builders.

This shift has been driven by changing demographics, the spread of technology, the rise of unbundled and distributed work, new behavior expectations, and a re-definition of what “work” is including the rise of fractionalized and free-agent talent who work for themselves or at multiple jobs and are expected to comprise most of the workforce in the US by the end of the decade.

Here are four core traits and how we can all build them.

1. A Passion for Excellence.

To be a leader in any field, at any level one must build proficiency.

One needs to learn a craft, hone skills, continuously improve, and remain relevant and up to date.

Experience while it will matter will matter less while expertise will matter more.

Too many “leaders” slip into irrelevance by letting their skills atrophy. Today due to the rapid change in demography and technology the half-life of whatever one has learned rapidly decays and the fuel tank of competence needs to be continuously filled.

Leaders set high standards for quality of product and service delivered, financial results and what they expect of people around them

Excellence is what attracts customers, talent and financial results.

And helps create world class cultures.

The best leaders never stop growing.

They are continuously learning and honing and upgrading their craft.

They do and do not just manage.

They seek not to blame but to understand, to learn versus believing they know it all.

They realize that only if they grow and the people around them grow in skills, reputation and knowledge will the company and its customers and clients grow.

They invest in learning, taking bets on the future, challenging existing business models, looking outside their categories for inspiration and potential disruption.

2. Face and Accept Reality.

A key to leadership is to solve challenges and address problems.

This requires confronting issues versus looking away or hoping some form of magical thinking will make them go away.

One cannot hope to get people to follow if they suspect one is not addressing real issues and challenges however difficult they may be.

Leaders embrace data and know math matters.

They accept that facts are stubborn things.

And while it may be forestalled for a while truth has a habit of breaking in.

Facing hard facts and addressing reality does not mean defeat or pessimism. But it is the first step in making things better.

To have a solution one must understand the problem.

This often requires creating an environment where people feel free to call out the problem and note that the brown moist thing that everybody is staring at around the conference table or on the Zoom screen is not a brownie but a turd.

Great leaders acknowledge mistakes. They know they do not have all the answers. This means they are open to criticism and correction, and they surround themselves with skill sets that offset and balance their areas of weakness.

3. Empathy combined with Vulnerability

Leaders bring about change and achieve goals by bringing other people along with them.

To do so it is key to understand where people are coming from. What their fears, concerns, challenges as well as hopes, desires and dreams are.

A simple way is to ask four questions.

a) What is on your mind?

b) What else?

c) If you were not doing this, what would you be doing or how could things be better?

d) How can I help?

Vulnerability is strength and not a weakness.

By speaking about things, one worries about, one reveals humanity and comes off as believable.

It makes other people step up to try to help and offset a person’s concerns or lack of competence with their or other people’s complimentary skills.

4. Continuous Improvement.

One improves leadership skills slowly over time and it is a constant effort.

Some days one improves and other days there are setbacks that one learns from. A practice of continuous improvement is what drives not just success for athletes but for all people.

The day we stop learning we stop growing and we begin dying.

By being accountable for our own feedback and by being comfortable helping others with feedback to unleash their growth is a sign of not just successful businesspeople but people who find success in every component of life.

Feedback is a key to growth and the journey forward.

1. Scan for signals: People are constantly providing feedback even if they are not vocalizing it. In some instances, you may gauge it in numerical signals from how well your writing is read, reacted to, or shared or whether you are invited to key meetings. Other times it is to watch facial and body language. You learn a lot by reading a room or a Zoom gallery.

2. Ask for feedback on a regular basis: One can do this with three simple questions which by the way they are framed ensure people are comfortable helping you since they are positive in tone:

a. What worked well?

b. If/when I do this next time what could be better?

c. Who do you think does what I need to do well and where can I learn more?

3. End of Day/Week Self Review: Most people know in their gut what worked or went well and what did not. Many successful individuals end the day or week with some variation of a quick review:

a. The Work: What went well with my work product that I feel proud signing it and what could have gone better.

b. The Team: What felt good and productive in the way I interacted with people and where could I have been better in some ways in handling my or someone else’s emotions.

c. The Improvement: What little improvement did I manage to make today or this week? A new habit. Learning a new approach. Strengthening a relationship.

Everyone can be a leader. We must sculpt at the block of marble we are to let the leader out just as Michelangelo did to let David emerge.

A new era of work requires a new era of leadership.

Rethinking Work: https://rethinking-work.io/

What Next? Fifty Year Careers.

Image by Sebdunedin using Midjourney

If we are lucky enough to live long lives, we all will age.

In 1900 life expectancy was 46 years.

Today in most countries the average life expectancy is around 78 years and with advances in technology this could soon be closer to 90 years.

Careers that lasted 30 years now could last 50 or even 60 years.

If one retires from a full-time job or primary career at 60 one still may have 30 years ahead of them which is why today many institutions and firms are rethinking careers and helping guide next acts.

Recently I had Seth Green who is the Dean at the University of Chicago Graham School on What Next? the podcast. The Graham School is a cognitive boot camp for continuing learning wherever you are in the world. The University of Chicago has also recently launched the Leadership in Society Initiative and the Imagine Pathways program for executives exploring their next chapter.

Seth Green’s insights and perspectives are not just for people in their fifties and sixties but for those in their twenties and thirties. Everybody who listens to my forty minute conversation will come away thinking very differently about their future and their careers.

After all, as Ann Dillard says ….how we spend our time is how we spend our lives.

Here are just a few of the discussion points to give you a flavor of the conversation.

1. Aging is a “prejudice against our future selves”. Avoiding thinking about or thinking negatively about aging or our future selves is a form of self-discrimination.

2. Many of us will “fail” retirement. A lot of retirement planning is about making sure one has the financial means to retire and how to remain healthy but that is not enough. Most people who can stop working soon find themselves without purpose or meaning or even identity since work is so central to identity, community, purpose and growth. The question of “Why am I waking up in the morning?” is rarely answered day after day after day with “To play golf” or “To travel”.

3. AI, Time and the rapidly declining half-life of Knowledge: Just as careers are getting longer the half-life of knowledge is declining faster and faster. Even if we are 30 our skills may lead to a forced retirement at 35 or 40 unless we upgrade and reinvent our skills.

The chart above is how AI has impacted the demand for software engineers. Remember how we were told to learn code and Mandarin was the future? Well AI enables software engineers to be far more productive than ever before and in many cases, replaces most of their tasks. And if you have the latest Samsung phone it does real time translation between languages.

Without continuous learning we are all becoming rapidly obsolete. Transformation no longer waits for retirement but is happening to us all the time.

4. To anticipate the future and to understand meaning we can learn from the past including when previous technology shifts happened.

Big ideas and approaches and insights are not only what we invent today but what have stood the test of time and trial. Too many of us believe we are discovering answers for the first time when they have been discovered and explained many times before.

Find what endures to endure.

Connect to what was to ensure one can connect to what will be.

It is important to learn what is important before it is too late.

5. Extrinsic Vs Intrinsic Purpose: In the first parts of our careers, we are driven by extrinsic goals such as money, fame, power, honing craft and seeking promotions. But later in our career or our second careers these extrinsic goals once achieved do not pull and tug or motivate as much as before and we need to know what drives us, what makes us happy and what is meaning. While the first mountain was driven by extrinsic purpose in later career one is driven by intrinsic meaning. Most successful people in their first careers find ways to discover their meaning and inner compass and align their careers to it and so easily make the shift to the second mountain.

What brought us and made us happy at the apex of our first careers are unlikely to carry over to our next act. How can we take what we are today and the best of yesterday but reinvent ourselves for the future? Often by revisiting vision, mission and purpose.

6. Cult vs Culture: If one does not know what one believes in and which way our compass points we can easily be magnetized in the direction of the crowd, the trend and to which ever our firm bends. Too many companies who believe “this is the way” and “our way or the highway” are not really cultures but cults.

7. Learning to travel lightly: Too many successful people cannot let go of the trappings of their first careers later in life. The retinue of handlers, the first-class flights, the genuflecting of minions and being the center of attention.

Seth shares the case of a legendary marketing professor and dean, Harry Davis who at the end of his deanship had to move to a smaller office and could only take a section of his library. He decided to leave behind all the marketing books even though he had built his career in the craft of marketing and only take the leadership books because that is what his career was going to be.

One must learn to travel lightly and let go parts of the luggage of the past every new stage of a career.

8. Do not live in other people’s minds: Too often we select careers and jobs because of what other people think vs what we are good at or find meaning in. We live in other people’s minds and give them the remote control of our lives.

9. The numbers that matter are not the numbers one thinks matter: For the lucky and privileged the size of the 401K beyond a certain point matter less and less. Adding resources has significantly declining returns. What matters are the numbers in the medical chart (health), the numbers of friends, the numbers of healthy relationships and the number of people one has helped. If one knew early on when we rightly focus on financial goals and building wealth that there were far more important goals, we would manage our careers and relationships differently earlier in our careers.

10. We should not price ourselves out of our dreams: Too many people find themselves doing a job they do not truly enjoy or love, much longer than they need to because the job creates the ability to fund a certain lifestyle. One’s lifestyle is rarely the dream. Funding the lifestyle often prices us out of the careers and vocations that truly resonate with us, but we now cannot afford to pursue.

Listen to Seth and dozens of the world’s most amazing leaders on What Next? This week we have Kass and Michael Lazerow who sold their company to Salesforce for 850 million dollars and are investors in companies like Liquid Death talk about the coming era of Entrepreneur, other recent episodes include Andrew Essex now of TCS and formerly a leader at Tribeca and the founding CEO of Droga 5 on AI and creativity and Peter Naylor of Snap, Netflix and NBC pedigree speak of the future of sports and much more. Wide ranging topics, global perspectives, amazingly distinguished and diverse guests sharing their best thinking and distilled insights on what next to help us all grow and transform…

For more about how to understand and navigate the future of work check out Rethinkingwork.io

Soft is the New Hard.

The Walk through Life Howard Walker

These days everywhere the mood seems to be war like and belligerent.

We hear about getting into “Founder Mode”, committing to “ Hardcore” and the need for more “Masculine Energy”.

We are told its time to go to battle, get into the trenches, defeat and crush all that comes in the way.

The end justifies the means.

Outcome is all.

Too bad any collateral damage that may result.

Maybe.

Or maybe not.

When two rocks hit each other both rocks lose parts of themselves in the battle. Its loud and hard but even the winning rock is bruised and chipped.

But water flows over rock.

In time it erodes the rock to nothing and keeps flowing.

Maybe soft overcomes hard by understanding the importance of grace, flow and connection.

Reflection Jiabin Zhu

Grace.

Grace is a fusion of demeanor and deportment.

The graceful combine a generosity of spirit, a sense of respect for others and a humility regardless of their level of excellence and skill.

Generosity of spirit in understanding that much of what is meaningful is not a zero-sum game.

Respecting others by being aware of them and their needs and backgrounds.

Humble in not losing one’s sense of perspective that everybody’s achievement while significant are due to a combination of many factors including luck, opportunity, inheritance, and the specific time and not just due to skill and hard work.

I Climbed a Mountain Steve Walls

Flow.

When in a state of flow an individual is inside and outside time.

Deeply immersed in something while extracted from the ordinary.

It can come in many ways including working on something which is challenging to stretch one but not so difficult that one cannot achieve positive outcomes.

It can come from being immersed in making things, building things, and creating things.

And from helping people grow, learn and flourish.

And it comes from learning and seeking wisdom.

In being able to connect the dots and see and understand things in ways that give one joy.

A Ganges Tale Thibault Gerbaldi

Connection.

Successful and happy people seems to have strong relationships to other people and to a higher cause or purpose.

Humans are social beings and most need some form of connection. The ability to invest and grow connections tends to be associated with joy.

We are living in an inter-connected and multi-polar world of 8 billion people with countries proud of their history and hopeful for tomorrow that all want a place and voice in the future.

Connection turns data into intelligence in AI, a series of words into stories that move us and connection works via genetics into progress across centuries.

Generosity. Respect. Humility engender Grace.

Creating, Learning, Building enable Flow.

Relationships. Purpose. Spirituality elicit Connection.

Intriguingly these are human and not specific to an industry, a gender, a race or a country.

They sometimes result in fame, power, and money but they are rewards in themselves.

Wherever you go, wherever you are and across the time they will give you strength and joy and often bring joy to those around you.

Soft is the new Hard.

My new book Rethinking Work is out this Tuesday (4 February 2025). Writing and ideas that will lift you, your company and your career. More here: Rethinkingwork.io

The Future of Work.

Next week (Feb 4) my second book Rethinking Work on which I have worked for two years will be published by HarperCollins in the US and India and then the rest of the world very soon after. It will be available as a hardcover, an ebook that can be read on any platform on any device, an audio book and on Kindle.

If you order it today you will have it on Feb 4. Here are all the places to order from including Amazon, Walmart, Barnes and Noble, Target, Independent Book Stores and more. For those ordering in India here is the link

The photograph above with me and stacks of the book before publication date is because HarperCollins shipped them early to a Wine Industry Conference in Monterey California that I was speaking at . HarperCollins has also agreed to ship books for events at American Express in New York, Bain Capital and their Portfolio CEO’s in Boston, the IAB Annual Leadership Meeting in Palm Springs and Nielsen’s leadership conference in Georgia all occurring this coming week before book launch.

I am now a traveling salesman!

Rethinking Work illustrates how every individual whether one is a CEO, a team leader, a middle manager or a new employee of any type and size of company in any country or industry can thrive during a period where work will transform more than it has in five decades!

If you find the writing in this thought letter worth your time, you might find the book a great resource, a tool, and a guide filled with new ideas, approaches, frameworks as well as perspectives, provocations , points of view and most importantly plans of action.

And like my first book each chapter is a book of its own versus the same chapter repeated a dozen times. There are chapters on developing reimagining strategies, recalculating financials, retraining the work force and how best machines and humans can align and what it will take to lead in the new era.

The book is likely to change not just how you think about your work and career but every aspect of your firm from strategy, to financial measurement, to talent development and organizational structure.

The book will be supported by a multi-media site, a You-Tube channel, a series of workshops, many other resources and partner as the Rethinking Work platform. You can already watch videos, listen to conversations and access research in the first baby step iteration of the platform here.

Below is a 90 second overview of the book followed by some perspectives on how work and industry will change in the next five years or less.

Some thoughts on the Future of Work.

1. Most companies will have significantly fewer full time employees than they have now because of in addition to AI, companies will leverage marketplaces and the growth of fractional employment.

2. There will be far more companies in the future. This year there will be a record 6 million new firms launched in the US alone and this is likely to grow exponentially as a combination of distributed work, new technology, market places and side hustles, low code and no code solutions make it easier than ever to create and scale new firms.

3. The least important challenge in the future of work is where one works. Companies who are focussed on getting everybody back to the office are asking the wrong question. The question should be how to maximize the impact of in person interaction in ways that are personalized and customized to Client needs, type of job, seniority, personal situation and market place dynamics for any particular expertise.

How can a company talk about personalization, agility, flexibility, cost competitiveness and being future forward and then enforce a one size for all model that insists everybody return to a container of the past and be expected to be taken seriously as a company of tomorrow and hope to compete with new competitors starting today that start with a blank sheet of paper that reflect new mindsets, new marketplaces and new technology?

4. We have entered an age of de-bossification as people are rejecting “boss- like” behavior and are looking for leaders. Bosses spend almost all their time measuring, monitoring, overseeing, allocating, nitpicking and “checking-in” while Leaders spend most of their time creating, selling, guiding, building, mentoring and growing.

The modern leader will not be just full stack but wide spectrum.

They will focus not on zone of control but zone of influence.

They will combine a growth mindset, an ability to connect dots in creative ways, and communicate and inspire with data driven story telling.

The crisis that many companies face is that of leadership. Of moving forward and reimagining what it is to lead a company, understanding what a company of the future is and reimagining one’s career versus returning to the status quo.

5. Three criteria will be key to the the future of work both for the individual and company.

a) Investments in learning and training across all levels.

b) The ability to connect people, data, interfaces and opportunities inside and outside the firm in flexible and cost effective ways. We are living in a connected age and connection is the key.

c) Trust and distinctiveness. Trust will be critical in a world of algorithms, agents, and AI for companies, for brands and individuals. Distinctiveness which can be defined as differentiation through excellence in key criteria that matter will will be a key to compete.

6. The individuals and companies that will win in the future will rethink the strategy of their firm for a world of a) declining and aging populations, b) shifts of power from scale of size, resources and spending to that of data, networks and talent, c) for a world where knowledge will be free ( but not wisdom, insights and ideas) , and d) where the ability to charge for hours of input and FTE’s (Full Time Equivalents) will be destroyed by Generative, Agentic and Physical AI.

Everything and more about the book at Rethinkingwork.io

Video by Ria Tobaccowala

Photograph by Rekha Tobaccowala

3 Ways to Thrive.

Successful leaders, teams and companies that endure over the long run seek to find balance, unity, and integration.

They work to balance opposing dynamics and points of view from how they invest for today versus tomorrow and how they compose leadership teams with differing points of view.

They strive to unite their organizations to work collaboratively to achieve common goals.

They recognize that in diversity there is strength, and it is important to integrate several perspectives and skill sets to succeed in an increasingly fast moving and complex world.

To balance, to unite and to integrate is difficult because it requires nuance, trade-offs, empathy, and communication skills.

It is recognizing that there is rarely a silver bullet answer or simple and easy solution.

Balance: The Mandalorian and Lawrence of Arabia.

Between 1962’s Lawrence of Arabia and 2020’s The Mandalorian there is much in common including each being an innovative use of a new film technology. It was 70 MM wide screen for Lawrence of Arabia and high-definition streaming for The Mandalorian which brought Disney into the future.

But in world view they are completely different.

In Mandalorian we sense a force and a code best captured in the line “This is the way” repeated throughout the series. There is a code of conduct almost religious. A way of doing things handed down over time. A deterministic march forward.

In Lawrence of Arabia a key theme is of old ways and traditions being challenged best captured by the line “ Nothing is written”. The desert is empty, and the sands are wiped clean with the winds of change. The past is not an anchor, and one must write, sculpt, and invent the future.

Most individuals and firms must balance both the roots (history, legacy, anchored costs, reputation, provenance, rule of law and expectations) of “this is the way” with the wings (leaps of faith, casting of on a new journey, challenging the status quo) of “nothing is written”. We must balance roots and wings.

Portfolio managers need to balance safety with risk to reach for returns while working to preserve capital.

Balancing is difficult but a focus on one extreme versus the other rarely allows for long term success.

Unite: The lessons of sports teams.

Regardless of the sport, the teams that win titles tend to share two characteristics.

1) Talent: they have a disproportionate share of great talent

2) Unity: they are passionately aligned and united to achieve a common goal

Often it is not the team with the best talent that wins but the one where the talent are passionately aligned and united either due to culture or great management.

Teams are not collected they are built and forged.

It takes time but once finished in the furnace and foundry of time and experience they operate at levels of performance and delivery that create a unique competitive advantage.

Similarly, companies win contracts and retain clients and take on external challenges where there is a glue of culture, purpose and values that ensure a gestalt (1+1=3) which sets them apart. People choose with their hearts while they use numbers to justify their choice.

A leader can get elected or selected by dividing and conquering for a short while, but sustained legacy and success is usually forged through uniting and uplifting.

Unity is hard and harder still in polarizing times, but a divided house will most likely fall.

Integration: Judicious surrender to the force of opposing tendencies.

If balance is often about allocating between today and tomorrow and unity about aligning different perspectives and people, integration is blending these opposing forces and personalities in a way that works and delivers.

While it may seem difficult, we all do so as individuals since each of us integrate many identities.

F Scott Fitzgerald wrote that “the test of a first-rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function”. When applied to companies we could write that first-rate companies are able to operate two business models at the same time, one optimized for today and one focused on creating tomorrow even if it eats today.

Today the big luxury brands are seeking to integrate aspiration ( specialness, history, limited quality, high price, cathedral like retail spaces) with access ( bringing in tomorrow’s buyers, reflect unique cultures, be available online) and integrating them so the brand can combine these different product portfolios and go to market strategies without the underlying story and brand falling apart from its internal dichotomies.

The best always balance, unite and integrate.

Balance roots and wings.

Unite diverse talents and voices into a common culture.

Integrate multiple and often opposing approaches.

These are the three keys to thriving.

Rishad Tobaccowala helps people see, think and feel differently about how to grow themselves, their teams and their business via the Rethinking Work Platform, The Athena Project and the Future Does Not Fit in the Containers of the Past Initiatives. More here: https://www.linkedin.com/in/rishadtobaccowala/