How Trying to be a People Pleaser Could be Making You a Bad Boss


You can’t please everyone, so maybe it’s time to stop trying so hard.

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We get it; you want to cultivate a happy, harmonious company culture. You want to keep your clients on your good side while allowing your employees the freedom to manage their own work/life balance. There’s no reason why you can’t please everyone, right? Wrong, says Dan Dinsmore, the founder of Overit. “I’m naturally a people-pleaser and that will never change,” says Dan, who adds that his tendency to try to keep everyone happy has, at times, been detrimental to his marketing agency.

“I founded a marketing agency because I like the combination of working with people and experimenting with new technologies. Marketing, though, is a service-based industry and we have to provide clients with impeccable attention in order to reach their goals and maintain positive relationships,” Dan explains. “We’re up for this challenge, but when we combine this with my tendency to try and please everyone, it can lead to the agency over-servicing clients to the company’s detriment.”

While this might seem great from a client’s perspective, it actually doesn’t build healthy agency/customer relations, says Dan. “From the agency side of things, we end up burning out trying to meet the demands of clients and risk the job satisfaction of our top talent. From the client side of things, they’re not gaining a strategic partner but rather hiring gophers only good to simply complete tasks for them. That’s a lose-lose situation.”

But Dan’s people-pleasing antics weren’t only negatively impacting his relationships with clients; it was causing friction among his employees, too.

“I wanted to develop a work environment that fostered creativity and integration among co-workers, not like other agencies with rigid management that only had the bottom line in mind,” says Dan, who notes that Overit’s mentality of a healthy work/life balance started out as a great benefit. However, as time progressed, it became apparent that some employees took advantage of the ‘life’ side of the bargain, leaving their colleagues to pick up the ‘work.’ “Without clear expectations and direction from me as a leader, this ultimately demotivated staff and caused friction in the office,” Dan admits.

While Dan acknowledges that being a people pleaser is part of his identity as a leader, he has implemented some strategies to combat the negative side effects this can have:

Hold your employees accountable
In order to overcome the rift among his workforce, Dan has since set clearer expectations for deadline, job roles and overall team support.
“In addition, we’ve raised the bar for current and incoming employees,” he explains. “While we might have a laid-back environment, we have to set the standard that the success of the company is in the hands of each employee’s’ commitment and motivation to producing quality work on time.”

Stop avoiding the tricky conversations
Or hire someone to have them for you, like Dan has done.
“I recognise the pitfalls that [being a people pleaser] can have on the business and have had the foresight to hire strong executive and management teams to support decision making,” he explains. “With a variety of perspectives in the room when making large business choices, I can see the full picture and move in the direction that makes the most sense for the agency – not just who it will make happy in the moment. It also makes me more accountable to the decisions we make as a team.”

Foster positive relationships
Dan argues that if someone is comfortable taking advantage of you, they’re probably not a positive relationship to have in your personal or professional life. “Instead, foster the positive relationships and work on growing those. If a client treats you as a partner and listens to your input, then bend over backwards to exceed their expectations,” he says. “Otherwise, move on and don’t measure the value of your worth based on what other people think of you.”


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