Dan Leahy | Crain's San Francisco

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Dan Leahy


MakerSights works with companies to evaluate concepts, styles and product attributes that enable management to focus on ways to keep customers happy, and run a profitable business.

The Mistake:

I never changed my mindset of being contribution-oriented.

When I was in my early 20s, I co-founded Savored, a digital marketing service for restaurants. At that point, the biggest thing I believed I brought to the table was that I was execution-oriented. I was very passionate about the business; I obsessed over the business.

In the early days, if something wasn’t done by myself or my business partner, it just didn’t happen. I measured my worth in terms of how much of an individual contributor I could be.

The mistake I made came as we grew. We hired one person, then two persons. All of a sudden, we had a 45-person team, and I was overseeing product marketing.

I found that I was not giving enough rope to the people that I was working with. I was micro-managing. I felt so passionately about the design of a product, I would often strongly suggest that we make particular changes, regardless of what others thought.

Being continually hands-on has some obvious short-term benefits. You have more information about the status of a product, you continue to feel really passionate about what you’re doing, and you’re always part of why a particular business decision is made. You realize that maybe there is a good reason, or maybe there isn’t, in doing something.

But the medium- and long-term implication of being over someone’s shoulder, always guiding them toward business decisions, is that it’s really disempowering to people. What I found was that people at Savored were starting to get frustrated. It’s no surprise: It’s not fun to have the boss always checking up on you, second-guessing you on major decisions.

I’ve realized that you need to relax on the pressure.

The Lesson:

As I’ve become more experienced, I’ve realized that you need to relax on the pressure. We work with some very large brands, and we are being entrusted with helping them support multimillion-dollar, sometimes even bigger investments. We provide the advisement that helps them make major decisions. So the temptation is there for me to be in the weeds, looking over the shoulders of team members who are working with those brands.

But if you hire the right people and let them do their jobs – and you have some short-term patience for people who make mistakes as they learn those jobs – it becomes a drastically different culture. It creates an environment where people are happily preparing things themselves, because they’re empowered.

When my co-founder and I launched MakerSights, one of the things we felt very strongly about was that we have a very strong feedback culture within the company. Every week we’re giving each other feedback about what we’ve noticed. We have an openness between peers, and between subordinates and their bosses.

This is something we really stress during our hiring process. We make people aware that they have a voice here. We really do believe in the space that we’re in, in our ability to recruit the absolute best and smartest people. But the only way the really smart, motivated people are going to stay is if we give them the opportunity to grow or take risks.

Follow MakerSights on Twitter at @MakerSights.

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