4 Key Traits of a Successful Business Person

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I think empathy is a super important quality in business, and in every layer of business. So in other words, the front-line employee needs to have empathy for the customer, and so does the person who’s in the back office, whether that’s a developer or a manager or whatever. And then there’s empathy within the team. It’s obvious in my mind to say empathy is important there. I think empathy is a word that has really risen into our business vocabulary in the last five years. But there’s a tricky part, which is that if I’m empathetic to my team such that I actually lower the goals that they can achieve, then in a funny way I’ve done them a disservice. Who am I to say what this person can or can’t achieve? A place that I find really fascinating/tricky is to hit the right balance of setting goals that are challenging but achievable. While I want my employees to be the best they can be and to continue to learn and grow, I also want to have empathy for where they are and for the context of where each individual employee is coming from. That’s a balance that I find I’m constantly tinkering with.


There is a key thing that has to happen in the team dynamic, which is the creation of trust and the nurturing of trust. So if you and I are on a team together and I’m going to push you harder than maybe you think I should, as long as we trust each other and we can look each other in the eye and say, “Hey, if we break the system, we’ll fix it together” or, “If this doesn’t work, we’ll figure out why it didn’t work and then we’ll be closer to making it work at this level the next time,” then we’ve created a safe space where we can push ourselves to our limits and push the system to its limits. And if we break it, we know how to fix it. If, on the other hand, one takes a leadership style of just cracking a whip, then it’s harder to come back from breaking the system or breaking the relationship.

Communicating Performance Expectations

I think there’s an element to this that really goes back to culture and having performance expectations be part of that culture, even before you hire the person. You’re sort of saying, “We’re signing on here together to challenge ourselves and perform at an extraordinary level, both for the sake of the company and for the mission, and also for our own personal growth and challenge.”


I don’t know how many years ago it is that Jim Collins wrote Good to Great, but the idea that was so compelling in that book for me was that there are these level five leaders. These people are the most incredibly successful leaders, judged by the performance of their business not just to achieve certain heights but then to endure at those heights. And the attribute that was present in those level five leaders versus the level four leaders, who achieved amazing success but maybe didn’t maintain that over time, was humility. Collins wrote this beautiful narrative about how counterintuitive that felt for many people, that the most effective CEOs had this deep humility.

I think there are a few reasons for that finding. One is because it builds greater trust with the team and it allows you to push the team harder and challenge the team, because they’re signed on to do that shoulder to shoulder with you. I also think that humility is really important because you hear what the market is telling you. The faster the world changes, the faster we have to keep up with new cycles of innovation and disruption, and the more we need to be able to hear the contrary point of view.

It’s an interesting balance, and it’s a real challenge to find enough conviction to leap into the unknown and try to lead a market or a business and at the same time have enough humility that you hear the feedback that helps you evolve your approach and stay on that leading edge.

About Dave McLaughlin

Dave McLaughlin serves as WeWork’s General Manager for the Eastern US ; Canada, where he is responsible for the company’s performance in several cities including Boston, Chicago and Montreal. Prior to joining WeWork, Davewas CEO & Co-Founder of Vsnap, which built video messaging tools for sales teams. Previously,Dave was Co-Founder and VP Business Development at Fig Card, a mobile payments startup (acquired by PayPal). Dave is also an award-winning filmmaker. He is a graduate of Boston College and lives in the Boston area.