My Leadership Resolutions
Mistakes made in ’15 and how I’ll move forward
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2015 was a challenging year for me professionally. I stepped away from Brigade, a company I not only co-founded but more importantly is working on the only problem I care about solving: getting people to vote and engage in American democracy. It wasn’t easy. My deficiency as a communicator and therefore a leader, and the realization that I wasn’t being effective in shaping the direction of the company were big parts of my decision. It caused anxiety, frustration, which begat more anxiety and frustration. I need to break that cycle.
When I graduated college, my first real job was a startup co-founder responsible for all technical and design aspects of the business. When we couldn’t raise a round in Pittsburgh, I ended up starting my own design agency. Never did I have a good manager to look up to and emulate. So my development as a leader was like a ship adrift. I proceeded on intertia alone with nothing to correct my course from whatever habits I developed growing up. When I first moved to Silicon Valley in 2007, I was given a piece of advice to join a startup before launching my own, which I did. However, I only took away the strategic and operational elements of the business and why we succeeded, and was never attuned to my managers and how they communicated with me or each other. Don’t make my mistake.
If I ever want to work successfully with other humans again, especially if I start another company, this is what I need to remember in 2016:
#1: Govern My Passions
In Star Trek, you can watch two sides of a coin. On one side you have McCoy, prone to cranky emotional outbursts, and on the other, Spock. Spock has hotter emotions than any human, but he relies on a philosophy of logic and the suppression of emotion through mental discipline.
“Really doctor, you must learn to govern your passions. They will be your undoing.” –Spock
I feel many learn growing up in my generation, at least I did, that wearing your heart on your sleeve and expressing yourself is a virtue. The 60’s Dad was strong, stoic, and never showed emotion or vulnerability. Emotion was buried deep. Boomer parents reacted to this by teaching the opposite, and rewarding emotional expression. In a position of leadership, every action you take can have a profound affect on people around you, especially those you manage. Leadership requires inspiration and motivation. Sometimes emotion is powerful, if applied properly and at the right time.
We celebrate those moments when being angry can stir a team to victory. If you’re unintentional about your emotions, you’ll have a hugely negative impact on your team and your organization. Displaying frustration, defeat, doubt doesn’t serve to motivate. Every startup has a mission. You’re the commander who’s trying to achieve the mission and get your troops to march through hell and take the beach.
#2: Ask For Help
In my opinion, this doesn’t mean hide reality from your team. I felt I was being transparent with my team by sharing not only the good, but also the bad and the ugly. Transparency is a virtue, or should be. However transparency alone isn’t enough. Often I expressed frustrations with executives, and either my powerlessness to do anything about it, or blind optimism that I’d handle it. It was selfishness shrouded in honesty and transparency. I was using my team as a shrink, expressing myself to them for the sole purpose of getting things off my chest. How did that affect them? Not well. If your manager, or general, is powerless to solve problems, then how motivated would you be? You can be transparent, but you either need a plan to move the company forward, or you need to ask your team for help. You don’t need to be the hero. Unlike Atlas, it does not need to all be on your shoulders, and it’s a mistake I made over and over again. Another was to feel overwhelmed by large problems, instead of breaking off smaller ones and attacking them as a team. I need to build empathy in a healthy way, empower others, and motivate at the same time as everyone has a stake in a common goal.
#3: Remember, “it’s not what you say, it’s how you say it.”
I love the old political maxim of talking only when it improves the silence. Churchill famously said nothing when Chamberlain, Lord Halifax, Churchill, and King George VI met to determine who would lead Britain into World War II, allowing Lord Halifax to make the case against himself. Kennedy famously ignored the hardline first cable from Khrushchev during the Cuban Missile Crisis, and responded to the more reasonable second. But then you need to be smart in how you speak. The ultimate form of persuasion is to guide the other person to come up with the idea, or come to the conclusion herself. The opposite of that is a frustrated outburst. No matter how good the substance is, the intent of you opening your mouth to speak is to get others to understand your idea. Defensiveness is the opposite of having an open mind, and it’s very easy to put someone on the defensive. You might as well not speak if this is the condition you’re going to create.
Always concede on principle was a favorite tactic of the great communicator, Ronald Reagan.
“The conventional view is that politicians like to argue and that they like to win arguments. Actually, they often have other priorities. The smart ones focus less on the principle than on the objective, the tangible result at issue. When sitting down to deal, they always separate the principle at stake from the actual stakes. Then, with the air thick with melodrama, they concede on the principle — and rake in the chips.” –Chris Matthews
I remember meetings where I would sit and listen, but then let so much pile up that I would deliver emotionally, which served no purpose, again other than to vent frustration. There’s a time and place for getting things off your chest, and a setting where you want to influence others isn’t one of them. Communicate with intent. Listen. Understand what others need to advance their goals. Help guide them to the right conclusion.
#4: Remember, “the fault lies not in our stars but in ourselves.”
Blaming other people and circumstances is really easy. Rare, or maybe never, did I take a step back and think strategically as to how I was going to create the outcome I wanted given the conditions I was facing. In a small startup, you just do things yourself, or work with a very small number of people. In a company larger than 10, you need friends, you need to influence others, and you need patience. As a designer, you’d think I’d know to use design thinking to solve problems, but my impatience and denial of the conditions of my organization was my undoing. “Why is it so hard to get things done here,” I asked. All the answers I came up with were things out of my hands, and never did I develop a sustainable strategy for achieving success from project to project, and steering the business in the right direction. I need to know the things I can control, who can help, and not to try the same approaches over and over if they’re not working.
#5: Fight the Next Battle, Not the Last One
Far too often in 2015, I brought up frustration over past battles, disagreements, or decisions made. “I told you so,” can be satisfying but it achieves the opposite of what you need when leading or communicating with others. I was accused once of hiring the wrong team to fit the needs of the company. To a head of design, that means you had one job. My defense: the product organization was changed after I hired my team. I was forced to go from an agency model (all work comes into design, we delegate and collaborate based on skill) to a pod model (each designer needs to operate mostly independently within a feature team). I did voice my opposition to the change, but was outvoted. Additionally, I was told I didn’t have budget for even a summer intern, let alone more full-time designers. I didn’t handle the change properly and move quickly to adapt. A more seasoned executive asks for the budget. I grew up in startups without that option. As a leader, and as an executive, it’s your job to anticipate the needs of the business six months from now, not react or re-litigate decisions from months past. I need to be flexible, see where the puck is going, and not be afraid to make changes or take risks.
#6: Do the Highest Leveraged Work
Being used to working in small companies, I was used to doing a lot of different tasks. At Votizen I designed and wrote the markup for the website and apps, did our PR, did growth and marketing work, business development, and helped with anything that had to be done. Managing a team and being a full-time individual contributor seemed pretty easy in comparison. But, much like talking and eating at the same time, this didn’t work so well. Design management is not only ensuring your direct reports are growing on their career path, but making their lives easier by taking everything off their plate that isn’t designing a great product. By designing myself full-time, I made that impossible. I had a laundry list of things in my head that I’d, “get to when I had the time,” and those things are still waiting. At Bessemer I know I have a limited window of time with a company, and I need to make it count by attacking the highest leveraged problems first: making sure our portfolio companies know the customers and their needs, goals, and pain; are properly positioned in the market and communicating well; and their products are solving the real problems. I need to work with and coach the designers that are there, not move the button 4 pixels to the left.
In summary, communicating with intent is my theme for 2016. The same way design is the rendering of intent, if you’re not thinking of your goals and moving forward, then you’re communicating without intent. Who knows where you’ll end up. Help me, yourself, and whoever reads this after you by responding with your own leadership mistake and resolution for 2016. Thanks for reading, and have a happy and productive new year.
