I am not sure I ever thought of running a digital business payments service in my 20's. Back then I was a consultant and product manager, and while I had ideas that I might someday follow the family entrepreneurial spirit, I had no idea what I didn't know. Looking back, I feel very fortunate for the journey to where I am today. That said, I do wish that I could have learned a few things the easy way instead of the hard way. If I could do a little Bill and Ted Excellent adventure (or hot tub time machine), I would have a few words of wisdom to pass along especially when it comes to running an organization.

So what is it that I would say to my 20 year old self and any other entrepreneur who asked? Focus on the organization. In hindsight, there are 4 critical things when building an organization that matter most that I wished I had learned long ago.

It Is Not Me, But We
Thinking about the organization separate from the people is critical to developing a healthy organization. It is tempting to think about the people first, as they are the ones who are affected by decisions. This is especially true when you're a "people person." However, it is important to establish this separation because it allows for non-biased decision making.

I first learned this lesson when I stepped out of the day-to-day management of my first startup, PayCycle, but remained active on the board. It became clear to me then that organization serves the leaders and the leaders serve the shareholders. There are times when tough decisions must be made that will adversely affect people within an organization, but are also absolutely necessary to its future. The ability to separate what's good for people and the health of an organization in the long run actually makes those decisions easier. It even makes communicating to those impacted easier. Organizational design that serves the leaders is key to success.

A Culture Divided
Culture should be divided into values and behaviors. Values will remain constant. They are the fundamental underpinning to all that your organization does; the reason why you do what you do. Defining organizational values is defining your true north when it comes to who you are, the people you work with and the customers you serve. True north shouldn't change.

Behaviors, however, can vary from year to year, person to person. It is important to evaluate these quarterly. I think of behaviors as attributes that you want to focus on for the organization. These can even be skills for the organization. The interesting thing about behaviors is that they are not static; they should change, especially as the company grows. I have found that they have an effect on the short and medium term results. Having both has become an important tool for me as I mange the growth of our company.

Being a great salesman can be a bad thing
I don't think I ever thought I would say that, but overselling is possible and is very dangerous. It isn't good to oversell a customer and it is disastrous to oversell an employee (whether you are recruiting them or enticing them to stay). When it comes to people, you must make sure folks want to come or stay for the right reasons and not just for a polished sales pitch. The most obvious example here is if folks are only coming for the money they make or might make. When that happens, you have failed to align on your values, your true north. The result is a disenfranchised employee that is difficult to mange. I learned the hard way a few times that the most important person to do the selling on working at your company is the employee themselves, not you. When you get that right, you'll have an easy time focusing on what makes the talent you already have happy and that in turn attracts and leads to more great talent.

C-O-M-M-U-N-I-C-A-T-E
It is not possible to over communicate. Again, it is not possible to over communicate. With all the channels of communication we have in our pocket alone, communication still remains one of the most fundamental issues within organizations. Communication is a basic tenant of building trust and leadership, and even though a leader may feel they have said something many times, my learning is that you can never say it enough.

There is a reason lessons are learned. For all the mistakes I have made in the past, I know I would do it all over the same. You cannot forgo failure and the wonderful process that is learning. For an organization to succeed it requires purpose, a belief in values, and the trust between those around you. It requires trusting yourself in the process to learn from the failures to make the journey better going forward. So while I have lots of things I wished I had learned, I wonder if I would have been able to learn them back then. So much for Bill and Ted, now back to my Excellent adventure.

Published on: Mar 26, 2015
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