Illustration by Olenka Malarecka
Illustration by Olenka Malarecka

Work Culture

Stop trusting your gut and lead with intent


Published on November 15, 2019

After retiring from the professional arena, many sporting superstars end up sitting on the sidelines armed with a clipboard.

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Team owners reason that because superstars were great at throwing touchdowns, slugging home runs, or landing free throws, they’ll be great at engendering that performance in others. But it doesn’t always work.

Often, great players are just that—great players. Achieving sporting greatness requires athletic skills but it doesn’t necessarily need impressive leadership qualities. When a former player takes hold of the reins, it’s not unusual to see them crash and burn.

Look at Wayne Gretzky. He’s often praised as the best ice hockey player of all time but he never led the Phoenix Coyotes to the playoffs as a coach. Then there’s Diego Maradona, an Argentinian soccer legend, who won the World Cup in 1986 but won just three games as a coach—he lost eight and drew another 12. And that’s just the start. Lou Agnotti of the NHL, Bart Starr of the NFL, and the NBA’s Isiah Thomas all marred wonderful playing careers with calamitous coaching stints.

Earvin "Magic" Johnson’s is one of the most well known player-turned-coach stories. After winning five separate NBA championships, Magic led the Los Angeles Lakers to his last NBA Finals, in 1991. The Lakers lost and Johnson retired the next year. But he wouldn’t be out for long.

Because people view leadership as the natural extension of IC work, businesses constantly promote the wrong people into leadership positions.

Just two years after his retirement, Johnson found himself back in the The Forum arena, coaching his old team. He took over a middling Lakers team with a 28-38 record about halfway through the season. While they weren’t losing every single game, they were hardly setting the court on fire. Under Johnson, the Lakers initially rebounded, winning five of their six opening games. But the honeymoon period quickly waned. After the excitement of a new coach wore off, the Lakers went into freefall, losing 11 straight games. After the season ended, Johnson resigned. "I want to go home," he told the Associated Press. "It's never been my dream to coach.”

Narratives like Gretzky’s, Maradona’s, and Magic’s aren’t peculiar to sport. History is full of people who were great doers but poor leaders. And that’s because while we understand the enormous responsibility leaders shoulder, few managers ever receive any substantive training on how to lead. They’re left to fumble their way through one important decision after another, with only Michael Scott’s antics in The Office as a guide. But it doesn’t have to be this way.

If leaders begin thinking about leadership critically and selecting their leadership style carefully, they can bypass much of the trial and error, skipping straight to better decisions and more effective leadership.

Leadership is doing the right things

Most people are promoted to their first managerial position from an individual contributor (IC) role. While this seems intuitive, experts are quick to highlight the risks and challenges of this progression path. Promotion decisions are typically based on IC performance, rather than their managerial potential, says Amie Devero, a C-suite executive turned leadership coach. This often results in management positions being filled by people who are good at doing but not at leading.

Devero uses the example of a high-performing sales professional who is good at sniffing out business, shmoozing with leads, and talking prospects into a sale. While those are the ingredients of a superstar sales rep, few of those skills carry over into leadership. A great sales leader must be adept at setting strategy, delegating work, planning workloads, mentoring direct reports, and liaising with stakeholders. “There is fundamentally no overlap between the skills that make someone a sales rep and those that make someone a great sales team leader,” says Devero. In fact, the respective skill-sets of a sales rep and a sales manager are diametrically opposed to each other.

Increasingly, leaders are waking up to their skills deficit and are pursuing training on how to lead. 

But because people view leadership as the natural extension of IC work, businesses constantly promote the wrong people into leadership positions. Indeed, according to Gallup, companies fail to choose the candidate with the right talent for the job 82% of the time—and that’s a problem. 

New managers usually enter their role with a significant leadership-skills deficit and are typically left to fend for themselves. To compensate, these burgeoning leaders will often fall back on what feels natural—commonly an autocratic (do as I say) or democratic (do as we all agree) leadership style. Alternatively, they may mimic the behavior of their former managers. “If their early leaders were tyrannical, and they were high performers, they may mimic that,” Devero explains. “If they were tyrannized and found that style demeaning and they couldn’t perform in that setting, they will consciously avoid that.” Using these tactics, new managers could end up as fantastic leaders but they could just end up as a Michael Scott.

But increasingly, leaders are waking up to their skills deficit and are pursuing training on how to lead. Many have turned to existing leadership archetypes from organizational psychologists like Daniel Goleman. Goleman discovered that most effective leaders tended to fall into one of six categories, based on their style. What’s more, he studied each style and was able to identify the benefits, drawbacks, and risks associated with each approach.

Dropbox profiled six leaders, who identify with one of Goleman’s six leadership archetypes, to learn about the benefits and drawbacks of each style.


“I believe every team should be given an overall company vision,” Nenad Milanovic, CEO of time-tracking app, Clockify, tells Dropbox in an interview. “Combined with the right amount of freedom, that allows employees to work out the best solutions on their own.”

To get the most out of his small team, Milanovic removed himself as a decision maker, transferring authority onto his employees. But it didn’t just improve capacity—by granting his employees autonomy, Milanovic believes it has buoyed their confidence and overall self-belief. “It shows that you trust their expertise because you’re not micromanaging everything they do,” Milanovic says. 

“A [visionary] leader takes a “Come with me” approach: she states the overall goal but gives people the freedom to choose their own means of achieving it. This style works especially well when a business is adrift. It is less effective when the leader is working with a team of experts who are more experienced than he is.” [HBR]

Milanovic does admit that a visionary approach has its drawbacks. The visionary leadership style requires outstanding communication skills from the leader as they must explain your vision first if you want the team to be able to follow and actualize it.

Affiliative leaders must act as the servant of their employees, helping them get the most out of themselves and the team.


“It's natural to disagree and have conflict in the workplace,” says Ladan Davia, CEO of Beeya, a meta-search engine for jobs. Davia manages a diverse cross-functional team and says each employee has their own goals, challenges, and needs. While each individual employee thinks their specific requirements are most important, Davia knows that a healthy business needs all of its departments working in harmony. As an affiliative leader, Beeya thinks it’s her job to cultivate that harmony by solving disagreements, promoting cooperation, and soothing personal disagreements.

Within Beeya, Davia explains that friction is more common between certain departments than others. Marketing and product commonly clash, for example, because “their jobs are just really different.” In these cases, Davia knows there might be irreconcilable underlying differences. While she can’t do much to reconcile their work, she can smooth their personal interactions. “Instead of letting feelings fester amongst teams, I address them immediately and bring everyone together to discuss and fix the problem,” Davia says.

“The hallmark of the affiliative leader is a “People come first” attitude. This style is particularly useful for building team harmony or increasing morale. But its exclusive focus on praise can allow poor performance to go uncorrected. Also, affiliative leaders rarely offer advice, which often leaves employees in a quandary.” [HBR]

Affiliative leaders must act as the servant of their employees, helping them get the most out of themselves and the team—and this can dissolve a leader’s authority. For example, some of Davia’s employees have, on occasion, treated her more as a friend rather than a boss. When this happens, Davia is quick to take the individual employee aside and clarify their relationship.


“I'm good at helping others succeed individually and as part of a team,” Jarie Bolander, COO of Lab Sensor Solutions, a mobile sensor as a service startup, tells Dropbox. “I gravitate to the coaching style because I'm a natural helper and connector.” 

Bolander recalls a recent project his employees were working on. They had made some initial headway but progress had slowed as they got further into the intricacies of the work. Some leaders may have reacted immediately and passionately, slamming their fists on the table and demanding improvements—but not Bolander. “We know that the team is working hard and that they’re frustrated with the lack of progress, too,” Bolander says. Instead, Bolander and his management team looked at the people behind the work, identifying skill and knowledge gaps that were impeding work. Then he created individual training plans for each employee, bolstering their abilities and helping them accelerate progress in the project.

A coaching leadership style doesn’t just benefit the individual. Since everyone is learning all the time, Bolander says his team feels more egalitarian. The more senior members of the team rarely throw their weight around because they’re reminded each day that there’s more to learn. “By coaching [my team] through technical challenges, we build esprit de corp that we succeed and fail as a team,” explains Bolander.

“This style focuses more on personal development than on immediate work-related tasks. It works well when employees are already aware of their weaknesses and want to improve, but not when they are resistant to changing their ways.” [HBR]

One of the biggest challenges with a coaching mentality is selflessness. Becoming a successful coach is predicated on putting your own success second. As a coach, it’s Bolander’s job to make sure his team wins. This is a challenge for any leader but if you are able to look past personal plaudits, the coaching leadership style can be immensely effective.


“I rarely provide specific tasks,” Jessica Mendoza, founder and CEO of Monadd, an address management startup, tells Dropbox in an interview. Instead, she sets high quality standards and leaves her employees free to set their own direction. 

With her developers, for example, Mendoza insists that all product development proposals be based on thorough research but what those proposals are is entirely up to them.

“A leader who sets high performance standards and exemplifies them himself has a very positive impact on employees who are self-motivated and highly competent. But other employees tend to feel overwhelmed by such a leader’s demands for excellence—and to resent his tendency to take over a situation.” [HBR]

Since pacesetting leadership focuses on quality rather than direction, it has a unique set of challenges. Without clear direction, employees can feel rudderless or unmotivated. Pacesetting leaders must be cognizant of less confident employees and must step in when they lose focus.

Leaders must also be careful to communicate the standards they set. Mendoza recommends values are seen and felt, in a manifesto, company values statement, or everyday decision-making. This is especially true in remote teams where employees don’t actually see their manager at work on a daily basis.


“I manage an exceptionally busy healthcare law firm,” says Erin Jackson, founding partner of Jackson LLP. “So our clients' needs are in a continuous state of flux.” With her work changing on a minute-by-minute basis, Jackson says she needs to rely on her whole team to get things done, which is why she adopted a democratic leadership style.

To facilitate her democratic leadership, Jackson has her staff work in a single open-plan office, which allows information to flow freely between colleagues. “We all work together in one room,” Jackson says. “This means we hear each others' calls, offer feedback on others' projects, and keep up with new issues being tackled by various members of the firm.” 

But it’s not just the firm’s work that is performed collaboratively. Jackson says she relies on her team to make business decisions, too—should they take on this client? Should they move into a different office? Should they hire?

It’s not just the firm’s work that is performed collaboratively. Jackson says she relies on her team to make business decisions, too.

Jackson says this leadership style is exceedingly effective. Unlike traditional law firms, which rely on hierarchical decision making, Jackson can delegate decisions to the most qualified or knowledgeable member of staff. That, she says, leads to better, more informed decisions.

“This style’s impact on organizational climate is not as high as you might imagine. By giving workers a voice in decisions, democratic leaders build organizational flexibility and responsibility and help generate fresh ideas. But sometimes the price is endless meetings and confused employees who feel leaderless.” [HBR]

While a democratic leadership style worked for Jackson, she is careful to temper expectations. Democratic leadership can seriously slow down decision making if you focus too much on soliciting the opinions of others. While she recognizes that her employees’ opinions are valuable, Jackson admits that not every decision needs varied input. Some day-to-day decisions just need to be made quickly and decisively. 


“There are no problems we cannot solve together, and very few that we can solve by ourselves,” U.S. President Lyndon B. Johnson famously said in 1964. Johnson entered the White House in turbulent circumstances, following the assassination of John F. Kennedy. Yet, in terms of legislation, he was one of the most active presidents of all time and he owes much of that success to his coercive leadership style.

There is a well-circulated photo of Johnson, taken in 1965, that shows him towering over Supreme Court Justice Abe Fortas, leaning forward and invading Fortas’ personal space. It’s emblematic of Johnson’s forceful leadership style, described by journalist Mary McGrory as “an incredible, potent mixture of persuasion, badgering, flattery, threats, reminders of past favors and future advantages.” Under Johnson, he was the sole authority. Johnson, and Johnson alone, set the agenda and made the decisions.

“This “Do what I say” approach can be very effective in a turnaround situation, a natural disaster, or when working with problem employees. But in most situations, coercive leadership inhibits the organization’s flexibility and dampens employees’ motivation.” [HBR]

While Johnson’s coercive leadership style produced quick and consistent results, the decision-making process was univocal and often alienating. This is the risk with coercive leadership styles as it treats employees and colleagues as mechanical cogs rather than human resources. That’s why coercive leadership is generally deemed inappropriate for all but extreme circumstances.

Leading with intent

Which brings us back to Magic Johnson and the Lakers. After the legendary point guard stepped back from coaching in 1993, the Lakers began looking for a replacement and they found one in Del Harris. Harris had played basketball in college but never made it in the pros. Harris loved the sport, though, and began coaching a local junior high team. He honed his craft, learned how to lead, and steadily progressed up the coaching ladder. Throughout his 20s, he coached three different high schools and was eventually recruited to the basketball program at Earlham College in Richmond, Indiana. In 1975, Harris landed his first NBA coaching job with the Utah Stars. By the time Harris arrived at the Lakers, he had been coaching for decades. Under his steady leadership, the Lakers made the playoffs each of the next two seasons. 

The collapse of the Lakers under its franchise icon—and the extraordinary revival under his unassuming and unheralded successor—illustrates just how important effective leadership is. The right approach can buoy the performance of an organization but the wrong approach—assuming that an expert doer will excel as a leader, for instance—can doom it to ignominious decline.

Finding the right approach isn’t always easy but it starts with intent. To become a great leader, you must think about the actions you take and why you take them. While leading with intent won’t make you a world-class leader overnight, it does put you on the right track. As leadership expert Scott Asai says, “If you're leading with intent, you'll still make mistakes, but you are, at least, growing towards being the leader you're capable of.“