What Kind of Leader Are You?

There are so many different kinds of leadership & leadership styles.  A broad categorization might include People leadership (management) and Subject Matter leadership (expertise).  Then there are various styles of leadership – inclusive, authoritarian, hands on/off, etc.

I would like to talk about People Leadership in this post, and specifically leadership in a startup or early stage organization where innovation, speed, energy and passionate engagement need to be the life blood of the organization.  My leadership style for direct reports is very much one of inclusion, collaboration, and support to enable people to perform at a high level.  But it all starts with the team composition and quality from both a skills and personality standpoint.  This will be an oversimplification, but I see the “process of people leadership” something like this:

  1. Ensure the individuals on your team are the most skilled at what they do.  I’m specifically talking about pure intellectual horsepower and subject matter expertise.  Every individual that works in my current organization goes through skills testing, both general intellect and functional specific.  There are homework assignments that are evaluated in a panel/presentation setting by a group of the prospective candidates peers and hiring manager.  This is an area I simply won’t compromise.  True story – I interviewed over 100 individuals for a critical VP Analytics/Statistician role I was trying to fill.  The skills test was nearly impossible, taking a consultant 3 months to solve.  Most candidates fell flat, some solved 10% of the problem.  My eventual hire solved the problem and recreated the statistical model, in its entirety, over a weekend.  Find the best no matter how long it takes.  The best team wins, always.
  2. Direct reports must have the right personality and cultural sensibilities to gel with your leadership style and culture you desire to create.  This is really important and I think often overlooked.  Team dynamics and how they operate as a team, not as individuals, will define the success of achieving organizational objectives.  I look for team members that share my philosophies on desired culture and management styles.  This does NOT mean, and this is important, finding “yes” people to agree with you all the time.  Quite the contrary, I explicitly encourage feedback and dissonance to create healthy debate.  The best idea should win, not the strongest personality or the person with the most authority in the room.
  3. Show up credible as a manager, leader and problem solver. I must inspire confidence in my team as a leader.  Have I provided a clear vision for where I am leading them (strategy)?  How do I treat people?  I often participate in even the most technical conversations outside of my experience, there is likely an angle to the problem that has not been considered.  My suggestion:  Inspire your team through your engagement in their work.
  4. Recognize what each individual needs – rewards, support, level of autonomy. Knowing this and responding to it on an individual level I have found will  maximize productivity, engagement and happiness.  I have also found that every individual can be widely different on these requirements.
  5. Become a master at conflict resolution and personality management.  All of us are different and respond differently to varying personalities.  It’s human nature.  I have also found that highly intelligent subject matter experts who are the best at what they do have a high degree of confidence that their way is the right way.  Getting different personalities to work together and facilitating the flow of information & communication in a way that creates a highly effective team environment is a lot of what I do on a daily basis.
  6. Encourage risk taking and let people fail. While I often hear this in organizations, I’ve rarely experienced a real commitment to it.  People may be given a second chance, but often the reputational damage discourages further risk taking.   A culture of innovation through a tolerance for mistakes and failures starts at the top of the organization, plain and simple.
  7. Make sure each individual knows clearly how success will be measured for the organization and for themselves.  This is an important point that I see too often misguided.  By setting rigid, documented objectives for individuals and tying compensation directly to these objectives can often result in undesired behavior, particularly in a startup or early stage organization where the continuous need for flexibility and adjustment for things as core as strategy and business model are paramount.  Don’t get me wrong, I see a need for written objectives and planning, but I also am explicit about how objectives can and will shift along the way and that there is no substitute for close and ongoing communication with direct reports.  I simply don’t get overly dogmatic on this point, especially since there is always a subjective nature to the review process.  A fully objective review process will undoubtedly lead to undesired behavior if there is even the slightest shift in objectives.
  8. When times get tough, real leadership begins.  I’ve been through some tough segments in organizations that I’ve run and you really learn about people when we go into “self-preservation” mode.  More than ever, I try to lead by example during tough times.  I over-communicate.  I really try to treat people with integrity and honesty through the challenging times and I’ve found by doing so it increases people’s tolerance for uncertainty, inspires confidence and increases loyalty.
  9. Don’t be a dick.  Seriously, this is a simple tenant but one I constantly review so as to not abuse the position of authority.  How are you perceived?  I have witnessed “dick” behavior destroy the culture of an organization almost overnight, morale sinks, motivation wanes, and at 6pm every night the place is a ghost town whereas before everyone was passionately working and collaborating long after the sun went down.

About Rob
I'm passionate about building businesses and have been doing so for 15 years. There's a few successes over the years in online community, transforming how cars are sold and pricing innovation for retail. Currently, I'm building a business helping companies manage their shipping and supply chain. I've made plenty of mistakes along the way but hopefully have learned from most of them. I am an avid angel investor, cyclist, Ironman, husband, father of 2 and traveler living in Austin, TX. More detail about my professional experience can be found on LinkedIn. You can also follow me on Facebook, Twitter, or pitch me for investment on AngelList.

One Response to What Kind of Leader Are You?

  1. Brian Reed says:

    I think you really bring up many of the keys points relative to leadership in a start up. In looking back on how i would rate myself on these leadership qualities, i would say i did some well and others not. One thing that a good leader has to have is passion and belief in the business that you are building. It is almost to the level that you commit to do whatever it takes. If you do not fully believe in the business you should not be the leader.
    Leadership at times is a little strange. To be a leader you often are ahead of what other people are thinking and ahead of the market. This requires the leader to have confidence in themselves, confidence in their business, and most importantly, thick skin. This all can result in a feeling of isolation for the leader and that is what a good leader has to prevent from happening relative to working with the team of people who are building the business. A leader of a start up has to be in total synch with thier team relative to the vision of the business.

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