I Was Wrong

The downside of being a “nice boss.”

For three years, Dan O’Malley tried to be the boss everyone loves—never criticizing, always smiling. Now, he says that was the wrong approach.

The co-founder and CEO of Bostonbased Numerated, which helps banks and credit unions automate their processes, went into crisis mode when, in March 2020, the Small Business Administration launched the Paycheck Protection Program. Numerated’s 55-person team worked 20-hour days for weeks to help banks process roughly $250 million in forgivable small-business loans per hour.

“I didn’t have the time to be worried about how people would take the feedback—I just had to give it,” O’Malley says. Brutal honesty can be jarring and can elicit defensive reactions, so the CEO made sure to start with a short warning: “This is probably going to come off rough, and I don’t mean it that way.” After detailing what went wrong, he’d ask: “How can I help?

What do you need to fix it?”

“It wasn’t a conscious decision,” O’Malley says of the shift—but his employees noticed the new tone immediately. “It freaked me out,” says Marianela Vazquez, SVP of professional services, who adds that her boss never previously got to the “nitty-gritty” of problems, leaving employees to address their own weak spots. O’Malley’s new hands-on approach meant encouraging Vazquez to make phone calls instead of sending ambiguous emails— and coaching her through conversations. Her team’s performance improved, and Vazquez now gives the same kind of feedback to her own direct reports.

Eliminating fluff while maintaining humanity has made Numerated more efficient—the company’s annual revenue grew to $28 million in 2020, up from approximately $1.8 million in 2019—and has almost doubled its head count. “Be super transparent,” O’Malley advises. “Just tell people how you’re thinking, as the leader. You don’t have to be right.”