How leaders lose their way

Keep your bearings.
Keep your bearings.
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I’ve always taken pride in relating to the underdog or little guy or gal. I grew up a skinny Asian kid who was often ignored or picked on. It stuck with me and branded my soul. As I grew up, I tried to stick up for whoever seemed excluded or marginalized. I became a Mets fan. I’d go to a party and find the person who seemed the most alone or uncomfortable and strike up a conversation. My zeal extended to my professional life. For the past sixteen years, I’ve worked at little companies trying to help them grow. Five years ago, I started an organization to recruit and channel young aspiring entrepreneurs to Detroit, New Orleans, Baltimore, Cleveland, St. Louis, Providence, San Antonio and other U.S. cities to make a positive difference. Young people + emerging cities + scrappy businesses = some of my favorite things.

As founder and CEO of Venture for America, I’ve found myself thrust into the role of ‘leader.’ I got invited to the White House (twice). I wrote a book. I won a couple awards and went on TV. I’ve traveled making the case for VFA in dozens of different cities and venues big and small. Our team has grown, our budget has expanded to $6 million, and we now have hundreds of talented, earnest young people building businesses across the country with more set to join them.

We are still a very small organization in the scheme of things. But to our audience–mostly 22 year olds who want to become entrepreneurs–we can loom increasingly large. And for the first time in my career, I’ve been experiencing life on the inside. When I show up to a party now, I often am trying to find the most prominent or powerful person instead of the opposite.

This might sound like a good time–it’s kind of what you want to happen starting out. But I’ve found it’s brought a different set of internal struggles that have made being a ‘leader’ difficult in ways that I would not have predicted. There have been times when I’ve feared that I’ve lost my way. I’m sharing some of these struggles because I think others might find them useful, either because they are facing similar issues or to understand how people in leadership positions can lose their bearings.

Here are some of the things that I didn’t see coming:

Time is your most important resource. When we were starting out, I’d take a meeting with absolutely anybody and respond as generously as possible. I was eager to share, and we had nowhere to go but up. VFA was about empowering a generation to make a positive difference in places that were often overlooked. I wanted to be as open and responsive as possible, particularly to young people.

Today, I still try to be responsive and accessible. But I have a company relying upon me to use my time efficiently and effectively. When I get outreach, I do my best to forward inquiries to the right team member. But I’ve started saying ‘No’ more and become more judicious.

This may be obvious, but the people and organizations I say ‘Yes’ to generally are able to drive value for VFA in some way. Sometimes, they have money. Thus, the trend is for a non-profit leader to become more responsive to people and companies who are rich and/or powerful and can help us achieve goals. This is resource-effective, and I love everyone who supports VFA, but it makes it natural to calculate a return on time spent.

One thing I disliked about being a lawyer was billing for my time. It’s not that bad in the non-profit context–people expect you to be close to your work and want to support you–but it can feel a bit like that at moments.

The team gets bigger. When there were only 3 of us, we would talk all the time. I knew what was going on both at work and with people’s personal lives. I often met colleagues’ families or loved ones.

Today, we’re bigger and more institutional by necessity and design. I’m on the road a lot and folks often need to make decisions without me in time-sensitive situations. People are hired that I haven’t worked closely with. Tension arises between personal connectivity and effective functioning of the organization. As you grow you let things go and hopefully empower others.

When things come up, I still think my experience from 2012 is the right one–so my instinct is to make a decision based on info that may or may not still apply. And my relationships are not as highly developed with the person on the frontline.

We’re not very big yet so this isn’t too major a problem. But I used to rail against people who made decisions without knowing what the heck was going on on the ground. Now I know how it happens.

People don’t tell you what’s on their mind. Several times in the past months I’ve had an extended conversation with someone and everything seemed great. And then a little while later I heard that I was getting the most rose-colored version of events and the situation.

People don’t like to tell the CEO bad news. There’s a pervasive instinct to emphasize the good and minimize the bad. I’ve seen this apply even to people who were not responsible to me – people have a natural desire to defer and keep it positive. When I hear something bad, it generally means that others have tried to solve it themselves for a while or it has risen to a certain level.

My CEO filter is now that I assume anything negative I hear is probably one or two degrees worse than is being conveyed, and half the good things I’m told are people just being polite. I have the feeling that even this doesn’t account for the full picture.

You talk a lot. I’ve historically thought of myself as an operator, not a talking head. But I started a non-profit trying to rekindle entrepreneurship throughout the US (down a ton by the way, we’re starting 100,000 fewer businesses a year than a decade ago, it’s a train wreck), and making the case is a key part of the job.

I’ve now spoken to gatherings of thousands of people in different places. And I’ve noticed that the more often I get asked to share what I think, the more I start feeling my thoughts are important.

I’ve always believed that talking about something is not the same as doing something about it. But if your job involves a lot of talking, it’s easy to get confused. I now see this confusion around me all of the time and occasionally get confused myself.

The people you deal with are fancy. I was the relatively anonymous CEO of a GMAT prep company prior to VFA. Now, I’m the CEO of an entrepreneurship non-profit that recruits college grads. One might think they’d be quite similar.

But as the CEO of Manhattan Prep I worked with 3 types of people–instructors, team members and students. All were pretty normal, though the Instructors were nerdier than most and just about everyone had a college degree (which isn’t the norm).

With VFA, I’ve met some of the most prominent people you can imagine, trying to get them to agree that channeling young builders to Detroit, Baltimore, New Orleans, and other cities is an awesome idea and we should do a lot more of it. Happily, supporters of Venture for America now include a couple billionaires and a sports team owner, CEOs of public companies, venture capitalists, major foundations and entrepreneurs. Many of them are tremendous human beings.

I’ve found myself in all sorts of unlikely situations and in some of the nicest buildings in the country. Humans are social animals – context is important. I’m reminded of politicians who wind up trading favors because they’re hanging out with friendly titans of business. The impulse to defer is strong. I almost feel glad that in my case I have nothing to offer but a worthy cause.

I will say that even the fanciest people I’ve met in Detroit, Baltimore, New Orleans, Providence, San Antonio etc. still tend to be pretty down to earth. Though I spend most of my time in Manhattan and Silicon Valley so my perspective on this is not the greatest.

I’m on a quest for growth. I see myself as a performance-oriented executive. I want to win. In a business context, that meant increasing revenues, profits, market share, and beating our competitors. In the non-profit context, it means increasing impact and training hundreds of aspiring entrepreneurs to revitalize communities around the country.

Increasing impact corresponds generally to growing our budget year-over-year. If put in a position to retrench and do the same thing for consecutive years to tighten up personnel and processes, I’d resist. My natural inclination is to be ambitious, stretch a little, put the organization in position to learn new things and maybe encounter a new problem or two.

Occasionally, someone asks about the right size for Venture for America and the need to maintain a strong culture. I agree that there’s a balance, and that there’s such a thing as getting too big too fast. But, perhaps because I’m a product of the American meritocracy in this era, I want to grow.

I feel bad for managers of public companies who have to report results to analysts every quarter and have their stock value constantly scrutinized. I’m sure that it sometimes leads to poor decision-making. Yet if I’m honest, I have a phantom VFA stock price in my head. And if I listen too closely to it, I’ll probably make a bad decision.

I was talking to a friend of mine, Fagan Harris, about Ta-Nehisi Coates’ book, Between the World and Me. And Fagan commented, “There’s a difference between being a truth teller and an organization builder. You can speak truth to power if you don’t have an institution you’re responsible for.”

He’s so right. Most leaders find themselves in position to be responsible to, and for, an organization. Incentives, efficacy, ego, social norms, context and a desire for success can lead to actions that wind up being counter to our dearest values. In a vacuum, you’d say, “How the heck could that person let that happen or take that position?” In practice, I’m finding it easier to understand.

I know that I say this from a position of rare privilege. I run a non-profit so if anyone has the opportunity to be a nice guy and stay true to a mission, it’d be me.

I started VFA in part because I was plagued by the sense that we weren’t producing enough builders and leaders of character in the U.S. The stats scared the heck out of me, and the legion of disaffected young people I encountered motivated me.

Now, I think our problems are born in part of institutions that make leadership all the more difficult. Going against the grain isn’t rewarded, as much as we might wish otherwise.

That is, to me the challenge. How do we reward and recognize the right kind of leaders, the quiet builders who lead by example and work outside of the spotlight? I’ve now met many of the people building businesses in Detroit, Baltimore, Providence, St. Louis, Cleveland, Pittsburgh, Birmingham and other cities without fanfare. They don’t have massive institutions beneath them. They’re short of social media followers. But it’s these quiet leaders who often reflect the best and truest values, who demonstrate character through sustained action and years-long commitment to unglamorous pursuits. I continue to admire them, in part because it’s even harder than I’d believed.