The CEO’s Weekly Checklist

As a first time CEO, there were times when I would sit at my desk and think, “What should I be doing today?” This feeling was especially strong after every financing round closed. After our seed round, we had defined the product and the engineers were coding it. I didn’t code. After I hired the executive team and started delegating, most of the bases were covered.

Of course, there is always plenty to do at a startup and the CEO is usually the head cook and dishwasher, but the question of where I should be productively spending my time continued to nag at me.

I was pretty aggressive about reaching out to other CEOs and mentors and this question was my biggest area of inquiry: “Hey, when you think back to when your company was my size, how did you spend your time?”

There were a number of suggestions that were specific to the company lifecycle stage like, “Get some alpha customers teed up” or “Get together a launch plan for Europe.” However, there were also some core, evergreen pieces of everyday advice that applied throughout the company’s growth:

Push the team

After you’ve hired rockstars in every essential VP role, it’s the CEO’s job to challenge them to do extraordinary things. Here are a few things I used to do:

  • Set aggressive goals. As a company we would set three goals every quarter and then I would individually negotiate three specific and measureable goals (such as “Hire a director of X” or “Meet with 20 customers”) for each of my direct reports that supported the company goals. Everybody needed to accomplish something more than just doing his or her job.
  • Give frequent feedback. In addition to giving extensive bi-annual performance reviews (see my previous post on the dysfunctional CEO), I would constantly pull VPs aside after meetings—“I like the way you handled that” or “Dude, that was a bit harsh”.  I’d keep in mind the “shit sandwich”, a piece of constructive feedback in between two specific, positive comments.
  • Hold weekly staff meetings. This was not a rote set of updates but a place where arguments were had and decisions made. After every meeting we’d send out a list of decisions and discussion points to all managers.
  • Schedule bi-monthly 1:1s. I’d usually spend an hour (no interruptions and paying attention!) going through progress on goals, how I could help, what’s going on within their teams, etc. The tone was positive, but I would constantly challenge them to do more with less.

Sell the vision

Shortly after our first round of funding, my co-founder, Scott Banister, turned to me and said, “I’ve heard you tell 100 different people a slightly different version of the same story. I had no idea you spend so much time selling!” He was right, I was constantly selling: soliciting investors and advisors, signing recruiters and PR firms, hiring employees, securing first customers, conducting company meetings, convincing reporters and sparring with industry analysts. They all demanded a compelling story, told with enthusiasm, and the CEO needs to be on the front line with these critical meetings that might turn into the tipping point between success and failure.

When I think about all the important things CEOs must do, succinctly and convincingly articulating “the story” is right up there. But there’s a catch: it must be told with both authenticity and passion—like it’s literally pouring out of them. We refer to the best of these entrepreneurs as “glow in the dark”.

Arbitrate disagreements

Half.com founder and CEO Josh Kopelman once told me that the thing he hated most about being CEO was when two of his smartest people would disagree and he would have to come down on one side: “These decisions were usually 51/49% and I was left having to console the ‘loser’.” He’s right. Arbitrating these disagreements is one of the hardest and most emotionally draining parts of the job, but many CEOs just avoid it and nothing breeds a horrible culture like a CEO who puts offs decisions or, worse yet, makes too many compromises.

I firmly believe that if the VPs aren’t periodically at odds with one another, then the company isn’t being nearly aggressive enough. Why can’t we get the customer feature in the next release? We should pre-announce new functionality and run under the ball! Great sales and marketing VPs constantly push the envelope with engineering, operations, finance and product.

Management By Walking Around (MBWA)

This is one of the few acronyms I retained from my undergraduate finance studies. I vividly remember reading it in some Management 101 textbook and thinking how simple and silly it seemed. Years later, I’ve come to believe that it’s a really important part of being a CEO. I probably spent three to five hours a week on MBWA and would put hour-long blocks in the calendar specifically for this purpose. Just a simple plopping down in an employee’s cube with a “Whatcha working on?” would yield so much valuable information. As the final decision-maker on so many difficult calls in a fast moving business, the CEO’s connection to the people that are actually writing code or talking to customers is critical. And you don’t get it from sitting in your office.

Talk to customers

A CEO should probably be spending about 30% of his or her time with customers, and this is especially true for an enterprise CEO. But this doesn’t mean talking with just the CIO or SVP, who most likely barely remembers signing the purchase order. However uncomfortable, I would insist on talking to the person actually using our product. I want to speak with the guy in the bowels of the datacenter, the one who probably comes into work without having showered and with bedhead. With just a slight prompting of, “Hey, I know you like the product but how can we improve it?”, he would unroll his manifesto of feature requests, bugs and other stuff to think about. Some of our best product ideas came on the plane ride home stitching together all the feedback.

Now, there are certainly a ton of other important activities—like raising money, setting a culture and hiring executives—that fall primarily on the CEO’s shoulders, but the aforementioned list includes the “responsibilities” I would hold myself to every single week.

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