Entrepreneurs can take management lessons from Masai Ujiri and the Toronto Raptors

Now that the dust has settled on the Toronto Raptors’ incredible NBA Championship run—four series of excitement that saw our city’s basketball team net its first ever Larry O’Brien Trophy— the sport’s top pundits are analyzing how the denizens of The North managed to achieve that seemingly elusive goal.

Many entrepreneurs are taking a similar look, but for different reasons.

The Raptors didn’t just win an NBA title, they delivered lessons in business management that can be applied across industries. They showed us that an also-ran could become a going concern in just a few years with the right combination of vision and managerial mettle. The most important management team member responsible for bringing glory to the franchise was team president Masai Ujiri, an executive who, if he chose to take a career turn, would surely be in high demand both on the inspirational speaking circuit and in MBA classes across the globe.

That’s because Ujiri managed to pull off a corporate turnaround of epic proportions. Recency bias may cause us to forget that the Raptors were the laughingstock of the league for much of their history. They cycled endlessly through executives, coaches, players who wanted to play elsewhere and, generally, put their fans through years of heartache, recently posting strong regular season records only to be summarily dispatched in the first or second round of the playoffs. Even if those losses happened to come at the hands of LeBron James—one of the game’s greats—and his former team the Cleveland Cavaliers, they still stung.

Here’s what changed—and the lessons owners of small and medium-sized businesses take from the Raptors’ win.

Don’t just talk about creating a long-term strategy. Envision and execute

Ujiri wasn’t satisfied playing second fiddle in the Eastern Conference, or in the league, for that matter. He was determined to win at all costs. Furthermore, he sized up the competition and realized that overcoming not just the Eastern Conference competition, but eventually beating the league powerhouse Golden State Warriors, was the ultimate hurdle that needed to be overcome.

Many business owners have a vision for the kind of business they want to build, or the revenue they hope to achieve. Only a handful will reach the promised land because they can’t—or don’t—execute. Ujiri reminded us that with the right strategy, an effective analysis of the competitive landscape and a determination of the personnel needed to succeed, anything is possible.

Sometimes you have to fire the boss—and your top player

Making counterintuitive managerial manoeuvres is a hallmark of leading entrepreneurs. But such moves can be extraordinarily difficult to execute because doing so requires that aforementioned combination of analytical ability, industry insights and chutzpah. Taking a risk is one thing; taking a series of smart, informed risks that offer a reasonable chance of success is something else altogether.

Ujiri seemed to lose the plot when, after the 2017/18 season, he fired head coach Dwayne Casey—who would go on to be named coach of the year—and traded away DeMar DeRozan, the team’s best player. They also traded away several role players and brought in new faces in moves that largely reshaped the team. It was an enormous gamble, and it paid off.

Ujiri, like many executives, understood that just because you have a mix of good players doesn’t mean you have the right mix. There are times when CEOs are forced to make personnel changes not because the people they have on staff aren’t doing their jobs well, it’s that they need different people who can deliver services in a different way, often to achieve a very distinct business objective. It takes both brains and guts to know when bold moves are needed.

It takes the right culture to succeed

The Raptors were summarily dismissed by leading NBA commentators, from the verbose Stephen A. Smith to legend Charles Barkley, during previous playoff runs. While one could argue a certain anti-Toronto bias, they also made clear that, in their view, the Raptors weren’t winners. They choked when the going was tough. They looked soft. Worse, they lacked a winning culture.

Ujiri changed all of that when he made those key personnel changes. In doing so, he underscored the need to build a winning culture that can attract, retain and engage the right employees to suit the organization’s long-term strategic goals. He stopped being willing to accept the Raptors as a sad-sack franchise.

When analyzing your organization’s needs, it’s worth asking the same questions he did: Do we have the right mix of talent and the right attitude to succeed? If the answer is ‘no,’ then it’s time to make changes.

Know your best assets, and use them wisely

The acquisition of Kawhi Leonard in the DeRozan trade was a wild card move for the Raptors. The now two-time Finals MVP was nursing major injuries while with the Spurs, and his ability to perform to his own lofty standards was in doubt. Ujiri opted for what has since come to be known as ‘load management.’ He would give his star forward ample rest throughout the season to ensure his body was saved for the playoffs. What seemed like insanity—why would anyone give their top player that much time off?—now looks like a stroke of asset-management genius.

While few CEOs will ever need to load-manage their top staffers, they will need to deploy them properly. Utilizing employees’ skill sets in the most effective way, and allowing them to maximize their own professional potential, is a challenge for many leaders. That’s particularly true when it comes to promoting employees into management roles for which they may not have the proper training, or even the right demeanour. Understanding your people, their aspirations, talents and limitations goes a long way to ensuring peak productivity and performance.

Management and staff won’t always get along—and that’s OK

Ujiri and long-time Raptors star Kyle Lowry were locked in a rift for much of the season stemming from DeRozan’s trade to San Antonio. Lowry and his former teammate were best friends and the former didn’t appreciate his pal being unceremoniously shipped out of town.

As any CEO knows, leaders and staff will sometimes disagree. While there’s nothing wrong with differing points of view—disagreements often lead to the sharing of different perspectives, compromise, new ideas and even better outcomes—squabbles can’t be allowed to grow into disengagement and dysfunction. Ujiri let Lowry simmer for much of the season before the two reportedly patched up their differences and agreed to disagree. They’ll now forever be linked as NBA champions.

The lesson: Sometimes it takes time to gloss over differences with top talent. If that divide can’t be bridged, it might be time to part ways. Thankfully for Raptors fans—in this case at least—manager and employee found a way to work together.

Marshall Egelnick, Managing Partner

Marshall Egelnick

905-946-1300, x. 226