Advanced Startup Management Techniques

Posted on May 2, 2015
Filed Under Business | Leave a Comment

Yesterday I spoke at an event and some of the stories I told about how I managed the team at Backupify got a good response - so much that I thought I should write about them. What follows is 3 management ideas that I wouldn’t suggest you use if you are just starting out, but might be useful to add to your toolkit if you are already competent at basic management tactics. The ideas are useful in specific situations that may occur as you build a startup, but probably don’t have the broad applicability of other management ideas.

Before I outline them though, I should let you know how I think about management at startups. I think most managers spend time coordinating work, checking up on work, and trying to motivate each individual. But the individual is part of a team and you have to constantly think about the team dynamic. Most people don’t.

I once read a comment by Gina Bianchini, and subsequently met her at a First Round Capital event where I got to discuss it with her for 5 minutes. Her comment changed the way I looked at management forever. What she said was “world class team chemistry trumps world class individual talent every time.” It’s brilliant. And it’s true. If you have a rockstar who isn’t a good fit with your team, pass on her.

As a manager, I always thought about team chemistry, how to get people to work better together, and communicate better. I felt it was a waste of time to try to teach them detailed things about their areas of work, because tech companies change so fast that even if you are an expert in marketing (or sales, or programming, or whatever) today, in 5 years the world will be different. So instead I tried to teach them new frameworks for thinking about things.

I wrote that so that you understand that if your view of management is dramatically different, these ideas may not work for you.

1. Create alignment by being the bad guy, or causing a commotion.
There is a great book called Us And Them: Understanding Your Tribal Mind. The book looks at many of the psychological studies that underpin group dynamics. At startups, there are lots of tribes, even though we don’t always realize it. There is the “speed wins, get it out the door, fix it later” tribe. They fight the “don’t release it until it is ready, even if that means missing the date” tribe. There is the “all press is good press (even if its bad press)” tribe. They fight the “what people say about you on social is your destiny” tribe, who believe that a few bad reviews sink a ship.

There are also workflow tribes. The “meetings suck and are a waste of time” tribe is always battling the “meetings are efficient if done right” tribe. There is the “plan the work and work the plan” tribe, who always battle with the “companies are made by last minute heroics” tribe.

Even though this book is mostly about ethnic, religious, and political tribes, I found the principles to be very adaptable to all the different philosophical tribes I encountered in the startup world. What’s great about “Us and Them” is it teaches you how to get tribes to work together. And one of the best ways to get tribes to work together is to have them align around a common enemy. That enemy could be an event, or a person, but either way, when they have to do it, they forget about their differences.

On multiple occasions at Backupify, I decided the team wasn’t working well together for some reason, and made myself the bad guy so that they could align against me on something. For example, there was a time when people were battling about budgets and couldn’t agree where we should cut. I announced that since they couldn’t agree, I was going to cut an area of the budget that none of them wanted cut. Soon enough they have fixed the budget on their own.

2. Force people to take another perspective.
The number one thing I look for in executive hires is the ability to see the world through someone else’s eyes, and engage on that level. It’s that corporate empathy that makes teams work well together. But in startups people tend to get territorial, and committed to their ways of doing things, and it is important that you break down those behaviors.

I once had two people who had very different ideas about how work should flow. They weren’t getting along and didn’t like each other despite both doing great work. I made them have lunch together, once a week, and gave them a series of topics to discuss each week. The rule was that they each had to take 10 minutes just listening to the other person’s point of view on that topic, and couldn’t speak. The first item to discuss on the list (which ties back to point #1 above) was for them to discuss how angry they were at me for making them do this. Their working relationship improved.

3. Gain support for ideas by making teams pitch both cases.
Startups face a lot of tough decisions. Sometimes people grumble, or even worse, leave the company, when a major decision doesn’t go their way. This is usually preventable if they have an understanding of how the decision was made, and feel like they had some input into it. Some CEOs try to do this by just meeting with everyone and listening to their ideas. I used a different process.

I like to take my top execs and individual contributors, split them into two teams, and give them each 2 hours to discuss a topic and come up with a presentation to justify their point of view. It’s important that you don’t let people pick which team they join - just assign them to a point of view to defend. This process has 3 major benefits.

First of all, each team will have some people who inevitably disagree with the point of view they are asked to defend. Those people actually make the team better by providing good counter points for the analysis, but more importantly, their resistance to the point of view tends to soften when they hear the analysis of others who support it.

Secondly, each team has to do a really good job of their analysis, because no one wants to be criticized by the CEO in public for having done a shoddy job. Teams have to be thorough even with they disagree with the point of view they are defending, or else they look stupid.

The third benefit is that by having each team present, everyone is forced to listen to detailed reasons, counterpoints, and counter-counterpoints, before a decision is made. Plus, when you get to the end and make a decision, you have all your top execs and key players aligned on all the issues, and why the decision was made. It is soooo much more effective than making a decision yourself and trying to communicate it down the chain of command where it will become misinterpreted and misunderstood.

The other nice thing about this process is, you can usually control it to get the outcome that you want, by asking the right questions and laying out the right ground rules. In the end, if you define the situation correctly, the team will usually all agree on the outcome you were hoping for.

There you have it. I used all three of these techniques multiple times at Backupify, and found them to be very useful. If you have questions, or want to buy me a beer and talk more, reach out to me on twitter.

Why I Still Love Print Media

Posted on June 21, 2014
Filed Under Critical Thinking | Leave a Comment

Reading this article about why print journalism still mattered inspired me to give my own take on this issue. Since this is a digital format, let me be short: digital media promotes breadth over depth, is less efficient to consume, and lacks the serendipitous aspects of print..

Now for the longer version. I still get a paper version of the Wall Street Journal and the Financial Times every day. I also get paper versions of Economist, Businessweek, FastCompany, Inc, MIT Tech Review, Forbes, Fortune, and a bunch of other less popular periodicals. The question is - why?

My answer has several parts. Let’s start with the most surprising part. Print media is more efficient to consume. In 20 seconds I can flip through a periodical, skim all the headlines, and tag all the stuff I want to read by just bending the ear of that page. Try doing that on the web. You can’t. There are delays and redirects and interstitials. Surveys and ads sometimes pop up, depending on what cycle we are in for the war between ads and ad blockers. Headlines are constantly rewritten and A/B tested for what gets people to click, not what is intellectually the most nourishing and rewarding, so if you don’t like linkbait, you can’t find all the really deep good stuff. Contrast that with the paper WSJ. I can unfold it on a table and quickly read multiple articles. No clicks, no annoyances, no loss of focus, no comments or video or other crap.

The second reason is serendipity. Sometimes I find great stuff in print. The best stuff is that unique article that you didn’t even know you would like but for some strange reason it caught your eye. You know what you find online? 1) The popular stuff that everyone is reading. 2) Stuff that is just like the other stuff you are reading. That’s fine. I’m not criticizing popular articles. But I am one of those people who likes to read certain topics that maybe aren’t that popular. Sometimes that small 2 paragraph article in a small box, deep within a paper periodical - the article that would never be popular online, and thus difficult to ever find, catches my eye. Some of those articles have taken me on interesting intellectual tangents I may never have found otherwise.

The final reason is, sometimes you need depth. A headline can only tell you so much. In a world where we have to be continually stimulated, not many people can focus long enough to read a 4-5 page magazine article. But some concepts just can’t be explained in 2 paragraphs. Many of the good print articles are online, but judging from my discussions with my own social circle, if you are the kind of person getting all of your news online, you probably aren’t the kind of person who takes the time to read the whole thing. Training your mind to focus, take a step back, and consume some depth has advantages.

So, economics aside, I believe print journalism still has a place. It’s more efficient, more in depth, and more serendipitous. If you feel like your news consumption is shallow, try going old school for a while. You may really like it.

Will Talking About Tradeoffs Save Our Economy?

Posted on March 3, 2014
Filed Under Critical Thinking, Economics | Leave a Comment

We live in a world of soundbites, which is unfortunate because it means the deep, rich, nuanced view that accurately reflects most significant issues in the world has been lost. Why read an in-depth analysis that requires 12 minutes of your time when you can just retweet a couple 140 character zingers on the same topic and feel like you’ve won a political battle? Our short attention spans, our neomania, and the media’s monetization of our hypernovelty seeking have discouraged us from reading any in-depth analysis on anything, and discouraged the media from reporting on anything in a deep, rich, and nuanced manner.

As a CEO, I had to get up in front of my company at the beginning of the year and talk about our 4 big goals. These are “the only 4 things we care about this year.” It’s a lie, unfortunately. There are really about 400 things I care about this year, but most people aren’t ready to have an ongoing discussion about the relevance, priorities, and dependencies involved in a whole bunch of subgoals. I have to keep things simple, just like the media. So, I have to admit, it isn’t just a problem with the media. It’s a problem with humans, with society, and with the way we think. We crave clarity and simplicity. Unfortunately, it’s killing us.

You know the straw man caricatures of each party as well as I do. The liberals believe that if we just made the rich pay their fair share and took care of the people at the bottom, that the economy would thrive. The conservatives believe that if we just kept tax rates low and let the market take care of things, the country would be fine. But it’s all wrong.

The truth is actually very complex, and what has been hidden from us, in our soundbite world, is the nuanced understanding of these issues. But there is hope. The CBO analysis of a minimum wage hike last month was the first time I ever remember a national discussion about tradeoffs. The analysis basically showed that such a hike would do two things:

  • 1. Lift 900,000 people out of poverty.
  • 2. Kill 500,000 jobs.

Wait, you mean we can’t get our economic cake and eat it too? Of course we can’t, but that didn’t stop each party from jumping on the point that most resonated with their ideology.

In my mind though, this was a huge step forward for the United States. For the first time, we are looking at an issue not as a panacea, but as something rich and deep and nuanced. Which would we prefer… 1.4 million people who are employed but under the poverty level, or 900,000 people employed above the poverty level but 500,000 people not working as a result? Employment is important because it builds skills and lets people eventually move to higher paying jobs. But working at a level that doesn’t make ends meet can also make things seem hopeless for the people in those positions. It is a difficult decision.

Government issues, particularly those that affect the economy, are actually full of tradeoffs that we don’t usually discuss. Studies show that unions destroy jobs, yet get higher pay for those who are employed. An article about North Carolina’s unemployment benefit experiment shows that killing benefits did encourage more people to seek work, but many of those people are employed in jobs way below their skill level just to make ends meet. A recent study showed that inequality, which is supposed to be the main topic of the next election, might more to do with changes in mating patterns in the U.S. rather that the traditional rich get richer rhetoric. Love vs. Money tradeoffs.

The truth is that these issues, and most interesting issues really, are very complex and difficult to understand in a 140 characters, or even a 700 word editorial. As a nation, I’m hopeful that this CBO discussion of economic tradeoffs will encourage people to talk about politics and economics in this way going forward. It’s all about nuance and tradeoffs, and unless we understand and embrace that, we can’t be successful at solving the problems we face.

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