You’re more than the Fucking Janitor: Thoughts on Startup Leadership

Last month, I had the honor of participating in the inaugural Foundry Group portfolio CEO summit where we had an enlightening discussion on leadership. To kick-off the conversation, one of the other CEOs volunteered the story of a time he felt he failed as a leader: he had a disagreement with some of the engineers on his team about the complexity of a given feature; and when their conversations reached an impasse, he took matters into his own hands and coded the feature himself.

I found the most interesting part of the ensuing discussion to be the disagreement over whether this CEO’s act of digging in and coding the feature himself was a leadership success or failure. We didn’t do a formal survey, but the group appeared to be divided into two camps: one that felt he should have focused on solving the communication and process (and possibly staffing) issues that prevented his team from executing as he desired; and the other that saw value in the example he set by showing he was capable of and prepared to do what he asked of others.

Earlier this week I read Zach Bruhnke’s excellent post You’re not the CEO – you’re the Fucking Janitor, and it took my mind back to that discussion about what good leadership looks like in a startup. My answer: it depends. It seemed to me that the folks at the summit who felt this CEO failed by doing instead of managing were leaders of more mature companies, while the ones who admired his leadership by example tended to be running earlier stage startups. As someone running a company that had recently raised our Series A and was growing from a team of 5 in January to 14 today, I found myself agreeing with both sides of the debate.

For a boot-strapped or even seed-funded startup, I think Zach’s post is spot on. The “CEO” in Zach’s story is a total douche, and my business cards say “Co-founder” precisely because calling myself the Chief Executive over 4 of my friends made me think of Yertle the Turtle. My dad always told me “the fish stinks from the head”, which is just his graphic way of saying great leaders lead by example. In my relatively short leadership career thus far, I’ve taken this to heart and always jump at the opportunity to do things myself.

In addition to the mutual respect and motivation Zach mentions in his post, one of the greatest advantages I’ve found in this approach is the intimate understanding a leader attains of how things are done within their team. Across the many failures of leadership I’ve observed (I was at Yahoo! for 4 years ;-) ), there’s a recurring theme of the leader being too removed from the actual doing. Especially in the technology world, the means of production can be just as important as the output. I can’t tell you the number of product and business leaders I’ve dealt with who treat engineering like a commodity instead of a potential competitive advantage. You only need to look to the world’s most valuable company to see what great supply chain management (i.e. caring how the sausage gets made) can do for your business. And when you’re a software company, every architectural decision your team makes has a bearing on essential business considerations like performance, reliability, time-to-market, and agility in responding to new threats and opportunities. That’s why awe.sm is, above all else, an engineering-driven organization (and looking for even more great engineers :-) ).

But in a later stage company, the leadership challenge is greater because you need to figure out more scalable ways of achieving these same goals. There was one particular line of Zach’s post that stuck out for me in this regard:

If you want to be a CEO in the sense that you dream of then you should remember to be the Fucking Janitor too.

A couple months after raising our Series A, I was washing dishes in the office and caught myself feeling self-satisfied because here I was, CEO of a company that had just raised millions of dollars, doing the dishes. I thought about my dad’s smelly fish saying and how he’d be proud of me. Then I thought about our investors and what they’d think of this…and it struck me they’d be pissed. Here I was, CEO of a company in which they’d just invested millions of dollars, doing the dishes instead of the dozens of other things only I could be doing to make their investment successful.

In the few months since then, my leadership focus has shifted. I still do the dishes when it’s my turn; when AWS shits the bed at some inhuman hour, I’m in our IRC room doing what little I can to help; and I always want to understand the gory details about why we made one architectural decision over another even if I wouldn’t know how to implement either of them myself. I am proud to continue to be a colleague to my team above all else. But leadership in a larger organization requires more than that. Our goal is to achieve on a scale bigger than what one person can achieve alone, and that means the leader needs to lead not just do. Doing is good, but when it turns you into a micro-manager or takes you away from leading, it can be counter-productive.

Delegation is hard. I’m finding delegating well to be much more challenging than doing things myself. Leading purely by example just requires effort and a willingness to do things that aren’t fun or glamorous, and as the leader you’re usually the most incentivized to get those things done. But effective delegation requires much more than mere will, it is a skill set developed with patience and learning and painful trial and error. It requires finding great people, training them in the skills you need them to have, motivating them to share your goals, empowering them with the resources and information to be successful, trusting them to do their jobs, and then giving them feedback on how to improve. I have come to believe my primary job as a leader is to enable the members of our team to deliver what the company needs from them, and that’s a lot harder and even less glamorous than being the Fucking Janitor.

15 thoughts on “You’re more than the Fucking Janitor: Thoughts on Startup Leadership

  1. Excellent article and description of the trial and tribulations of the startup dilemma! Having been in a couple startups myself from the team standpoint, I can appreciate your take on doing the dishes and also having the primary job of leading the team. You sound like the type of person we all would like to work for!
    J

  2. I heard yesterday, on the radion ( bbc world service) a panel discussin inequality, in that one member ( billionaire investor etc etc) says that a true leader ( and he quoted Bill Clinton) has the ability to take on board all concerns, make all people feel important, and mediate in a way that I productive.
    Now – am I am sure a lot of people may agree/ disagree sometimes , there is no other way to roll up your sleeves and just go and do it yourself.
    I don’t advocate having a mad dog/ bullish ” I will go and fix this myself” attitude, but I feel a CEO #must have the skills, determination to do things himself, but do it as a way of showing leadership with humility, not ” I don’t need any one of you – you are fired”
    A start up stops being a start up once a product/service is successful. ALmost always it needs more than one to make it happen – SEOmoz – from 5 to 14 – is a good example. You can use contractors of course now and then, but ultimately its your team, and its your leadership which will build or destroy the team.

    I once read a fab quote – its not how you you talk with your superiors, but your inferiors that truly shows the kind of person you are.

  3. It scares the crap out of me when CEOs don’t know their product or their numbers. I almost don’t want to do their SEO…almost…

  4. Jonathan,

    Thanks for the shout out and for reading my post in general. As a whole I completely agree with you on this subject. I think one of my main points was that most of the time when your employees know you are willing to sweep the floor do the dishes etc. the right ones don’t let you.

    All of the employees in my office (including me) were willing to do anything to make the office a better place. Whether that meant staying late, coming in early or sweeping the floor before they left.

    They did not all start out that way, they got it from me and from each subsequent hire learning from the ones before them. My employees were always what most people would call “Overpaid” and they were all on salary, they never minded staying late but I did my best to send them home early when I could as well.

    I think being the kind of CEO I talked about in my post is what leads to work environments where you can be the exact kind of CEO your investors would want you to be.

    All in all excellent post! Keep up the good work.

    Stay humble and stay hungry
    Zach

  5. In case you feel better by degrading people below you, for example janitors, you are not a leader at all but a tyrant. There are many tyrants among entrepreneurs because in companies there is no democracy. The person who has the money has the power. Leadership is about motivating people to follow you not about establishing yourself as the top dog and subjugating others.

  6. There’s a lot to like about this post, but most of all it makes me want to invest in your company. However, I do not have 4 million dollars. Let me know if there’s a way to get in on the Strauss machine for $20 at a time, or if you need a jingle length theme song.

  7. I am not sure why it’s less glamorous than the you-know-what janitor. At the end of the day, you can see a lot more of the effect of this work than just a shiny toilet.

  8. Great post! Would love to hear how this changed for you over time compared to your most recent post about stepping down. That’s incredibly hard to do and not enough people are talking about the role from Founder to CEO. It’s hard.

    1. Basically the last paragraph of this post sums up what led me to the decision to change my role: delegation is hard.

      In the case of where we’re at with awe.sm, we ultimately decided that it was more valuable to have me continue to work directly on product and engineering than to have me learn how to be a better delegator this time around. I still think delegation is a very valuable skillset, and I look forward to learning from Fred’s (our new CEO) example.

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