Rookie Leaders

A silent plea for help.

By Matthew Laffer
September 29, 2019

“I have no idea what I am doing, and I can’t say
anything to anyone because they think I have the answers.”  

After coaching hundreds of young, bright, overachieving leaders of successful startups, it's surprising how often I heard this plea for help. But each time, we worked through it together. It's been an extraordinary honor and privilege to have been a part of their individual journeys – from early-stage, quirky startup to some of the most notable company acquisitions in history, including Flatiron Health (acquired by Roche for $1.9B), New York City’s largest, private transaction ever.

We’ve analyzed thousands of coaching sessions in an effort to identify the biggest challenges rookie leaders face and to help accelerate their learning and development to meet these challenges head-on. The research shows that only about half of new managers ask for help (Harvard Business Review / Becoming the Boss). They believe they are supposed to have all of the answers and they fear that asking for help signals that their promotion was a mistake.

In 2013, I founded Goalspriing, a modern coaching company supporting private, venture-backed businesses and their people at all levels of the company. Leadership coaching is a priority for many of these companies given the pace at which individual contributors are becoming first-time managers. Promoting from within provides the career advancement opportunities that people are seeking from their companies and helps to engage and retain high-potential employees. Over the past five-years, Goalspriing has been an integral part of the Learning & Development (L&D) strategy at some of the world’s most innovative startups.

The purpose for writing this piece is an attempt to examine the inherent challenges of promoting independent contributors to first-time leaders, particularly in startup environments. Startups are places where we want today what we dream about tomorrow and this domain represents a special and unique context for new leaders. Startups by nature are fast-paced, action-oriented, and much of the learning is on the job.

Knowing has become obsolete. Not to know is the natural order of our times,
and how we behave when not knowing has become the new currency.

Many first-time leaders show up for work blind and groping in the dark. This is compounded by the high-stakes of a startup where work can either make us or break us. And while the workplace of a startup is typically more people-focused than the mass corporate market, it still has too little humanity and too little poetry. Emily Dickinson often says more in one line about the invisible structures of leadership than an entire shelf of contemporary business books. Leading successfully in a startup requires the ability to see what’s possible but not yet realized.

Leadership is seldom performed in ideal circumstances and the transition from independent contributor to first-time leader is one of the most challenging in business. This transition can seem like a lonely voyage into the unknown. It brings new roles and responsibilities, new ways of looking at organizations, and new ways of relating to peers and multiple constituencies. Ensuring a new leader’s success is critically important to their career and to the success of the entire organization. Organizations suffer considerable human and financial costs when an individual contributor who has been promoted for strong performance fails to adjust successfully to their new leadership role. So why do we spend so much time and so many resources developing senior leaders and so little time developing rookie leaders? ¯\_(ツ)_/¯

One of the tragedies of many startups is that the people placed into positions of leadership come from technical backgrounds in which their previous success bears little resemblance to the qualities they need in their new roles. New managers are often surprised to learn that the skills and methods required to succeed as individual contributors are starkly different than those required for success as leaders. We can no longer ignore the gap that exists between their current capabilities and the requirements of their new position. Successful leaders need to be human beings engaging other human beings in a conversation about the future.

The big challenges of the future aren’t technical – they are human.

Technologies change. Businesses change. Markets change. But human nature is a constant. What really matters is understanding people – it’s one of the greatest predictors of success in leadership and in life. And there is no algorithm for completely understanding people. At least not yet.

These five areas provide a glimpse into some of the more important aspects of my conversations with first-time leaders. While it’s not a complete list, I hope it can serve as inspiration for deeper exploration.

Authentic Leadership. 

Authenticity surfaces early on during a rookie leader’s journey to discover their leadership style, and with good reason. One of the crucial tasks of a leader is to find their own voice. Discovering one’s leadership style comes to those who know themselves – their strengths, their values, and how they best perform. They must have a deep understanding of not only their strengths, but also their weaknesses, how they learn, how they work with others, and where they can make the greatest contribution.

Most people think they know their strengths. They are usually wrong. More often, people know what they are not good at – and even then, many people are mistaken. First-time leaders should waste as little effort as possible on improving areas of weakness. It takes far more energy and work to improve from weakness to mediocrity than it takes to improve a strength to excellence. When people operate from their strengths they are more likely to achieve true excellence.

Strategy.  

Seldom does the conversation start with the need to develop a strategy. It usually starts with a desire to get better at “time management”. Strategy is frequently concealed behind the facade of time management. Rarely is time management the real problem to be solved, and the same can be said for moving faster. Rapidity is a force causing massive stress in the workplace. When things are moving too quickly, balance, quality, and growth are compromised. The “move fast and break things” startup culture is now breaking us.

Paradoxically, the wisdom to manage time requires that you slow down or, better yet, stand still. For in the stillness is where clarity is born. And as a leader, strategic clarity should lead the way. The essence of strategy is being clear on what you are and are not going to do.

The fastest code is no code at all. In other words, the fastest way to get something done – whether it is writing a line of code or crossing a task off your to-do list – is to eliminate the task in the first place. There is no faster way to do something than not doing it at all. Most leaders waste time on tasks that don’t matter. Successful leaders focus on just a few priorities and hone in on their successful execution.

Having a framework for thinking strategically, maximizing your focus, and mastering your priorities solves the, often misdiagnosed, time management problem.

Leading a Team.

New leaders mistakenly liken the management of their team with managing individuals separately. Simply focusing on one-to-one relationships with members of the team can undermine a culture that will enable the team to reach its full potential. Many first-time leaders spend too much time with a small number of direct reports, often those who are most supportive, rather than harnessing the collective power of the team. 

Leading a team goes beyond direct reports and also requires managing the context within which the team operates. Building relationships with key people that the team relies on will ensure the team has the resources necessary to do its job.

It’s also worth emphasizing the old adage “actions speak louder than words”. What leaders say matter a lot, but their actions matter most of all.

Given the magnitude of hiring and growing a team, I will write a separate piece for identifying and vetting team players.

Work-Life Balance.

We’re so busy asking people about their OKRs (Objectives and Key Results) we forget to ask, “R U OK?”. Leaders need to check in with their direct reports about more than their work and connect with the whole person. Leadership is a continuous conversation, and an opportunity to get to know a person – to genuinely create and nurture a relationship.

And then there’s “hustle porn” which has ruled startup culture for too long. People are working harder and longer hours than ever before with the belief that it’s the necessary route to happiness. But hundreds of studies show this is plain wrong. Happiness leads to success, not the other way around (Lyubormirsky, S. / Benefits of Frequent Positive Affect).

The mystery of time has always been unsettling, stirring deep emotions. So deep as to have nourished philosophies and religions. The key to better results is not more time spent working. In fact, the research shows that if you reduce work hours people are able to focus their attention more effectively, they produce just as much, often with higher quality and creativity. Engagement and retention are also higher in companies that give people the flexibility to flourish in their lives outside of work.

Those who boast how many hours they work are inadvertently revealing their devotion to a tired and erroneous belief system.

We have traveled too far and too fast over false ground.
Our souls have come to work to take us back.

Career Advancement.

Successful careers in a startup are planned. Said no one ever. Careers advance when people are prepared for opportunities because they know their strengths, their method of work, and their values. Or because there are many jobs-to-be-done in a startup and the opportunity to jump in and roll up your sleeves is attractive for all parties. Either way, career advancement and career development are not the same, and the order in which they occur matter a lot. A development-first approach increases your likelihood of advancement and optimizes your likelihood of success when you reach that next level.

The lure of working in a startup is real. But beware if you are making the leap after a couple of years at an investment bank or a consulting firm. Visibility into advancement at a startup is low and the development programs are not [yet] built for people coming from more traditional, professional backgrounds.

After thousands of coaching sessions with hundreds of first-time leaders, I’ve come to three key conclusions.

First, being an experienced leader, let alone a rookie leader, is a highly challenging role. First-time leadership is a true adventure of growth, but it shouldn’t be done alone. Startups are great at developing the customer experience. But when it comes to developing people, they are flying blind. Startups and their people stand to benefit greatly from working with coaches external to the organization in ways that can’t be replicated internally.

Second, leadership training is important, but most training programs fail because the information remains theoretical until it’s brought home into one’s self and into daily practice. Coaching is a highly effective method of converting information into knowledge by taking action. It is knowledge, not information, that is key to successful leadership.

Third, it’s not business, it’s deeply personal. Of all the leaders I’ve worked with and observed, the best leaders approach their work as a calling, which means the work is an extension of who they are. Leadership is something more essential, it’s heart and soul, and it’s relationships. And good relationships make us happier and healthier, and have a multiplicative effect, building and spreading further than we’d ever imagine.

What if the real KPIs (Key Performance Indicators) are the friends we make along the way?

Matthew Laffer is a 3x entrepreneur and the Founder and CEO at Goalspriing.