What is Leadership?

Recently Steve Wulchin (who has also been an investor in our funds at Techstars since the beginning) was asked by two of his nieces to talk to them about leadership. As part of his preparation for the session, Steve polled a number of people that are in leadership positions, including me. These are people that Steve has known for years, and their experiences cover a wide range of leadership roles in a variety of organizations.

The group that Steve polled had experience in startups, Fortune 500 companies, the highest levels in the military (in theatre), running venture funds, teaching at Stanford, running small organizations, and running large ones. Steve asked them 4 simple questions:

  • What are 3 traits of successful / effective leaders?
  • What are 3 traits of ineffective leaders?
  • Why do organizations succeed or fail?
  • What practical advice can you offer to 2 young leaders?

Steve shared the answers with me, and I thought they were interesting and asked if I could share them here on my blog. Those answers are below, largely unedited. Each set of answers is one person’s response. I won’t tell you which sets are my answers, but maybe you can guess.

3 traits of successful / effective leaders:

  1. Not afraid to fail
  2. Think and make decisions (on occasion) “outside the box”
  3. Confident

  1. Provided a vision for the future (doesn’t have to be detailed)
  2. Consistent in decision making – meaning they are quick to make a call, but reserve the right to change their mind later
  3. Provide opportunities for others to lead within the context of the vision

  1. They were quiet, mostly introspective, “coach-like” men with a well-articulated vision (consistent commander’s guidance).
  2. Allowed subordinates leeway and opportunity to succeed, on those occasions where they failed, provided low key counsel and more opportunities.
  3. Knew their men very well to include families and important life events.

  1. Honest
  2. Direct
  3. Clear communicators

  1. Build Trust
  2. Have a Compelling Vision
  3. Drive Results

  1. Have a compelling vision and are effective communicators. They are able to get people to buy into and contribute to their vision.
  2. Bring out the best in their people. They are able to fire people up, to get them to commit themselves, to provide more than they realized they were capable of.
  3. Are broad-minded. They see issues, opportunities and people in all their complexity.
  4. Surround themselves with people who complement their strengths. No human being is fantastic in every way. Business is a team sport. The best leaders find and retain people who possess strengths they do not.

  1. Ability to attract and retain top talent – not threatened, and, in fact, enthused about people who have differing points of views, approaches, and backgrounds.
  2. Willing to take responsibility and make the “tough calls” – in a straightforward and transparent way and realizing that they may not always be the “popular” choices.
  3. A rare mix of visionary ability and executional pragmatism – naturally comfortable, willing, and able to participate, interact, and assist at all levels

  1. Calm under pressure and in great success
  2. Driven by facts but motivated by possibilities
  3. Great story tellers

  1. They find a way to get people excited about what they’re doing, to do the impossible.
  2. They are secure and confident and surround themselves with people smarter than they are.
  3. They are never satisfied.

3 traits of ineffective leaders:

  1. Purely “ass kissers”
  2. Unfamiliar with market competition
  3. Afraid to ask for help from “others”

  1. Aren’t knowledgeable in the area they are trying to lead, but try and hide it
  2. Afraid or reluctant to delegate tasks or leadership
  3. Take credit for wins and blame others for losses

  1. Loud, often profane men who could be counted upon to belittle subordinates both privately and publicly
  2. They were aloof, above the fray
  3. Knew little of what was really happening in their unit

  1. Bossy
  2. Not leading by example
  3. Inconsistent

  1. Lack Humility; i.e. put yourself first
  2. Dishonesty
  3. Poor Listener

  1. Playing politics. My last boss at ABC Corp was one of the worst leaders I ever met.  Any time we had a conversation, the only angle from which he would look at it would be “Politically, how is this going to make me look?”  It got to the point where the only time I ever engaged him was to get my expense account approved.
  2. Disengagement. There is a fine line between letting your people do their job without interference and being disengaged completely. I had a boss at XYZ Corp who crossed that line and never looked back. I used to call him with about various topics and the phone always went to voice mail. I would leave a message, and about 5 minutes later, I would receive a terse, one line e-mail response which was not helpful at all. The guy had no interest in talking to me in person. In 18 months, I think I spoke live to him less than 10 times.
  3. Arrogance or Know it All. The opposite of disengagement. I guess this can also be called closed mindedness. This is the person who follows the 2 Rules of Business. Rule #1 – The boss is always right. Rule #2 – If the boss is wrong, see Rule #1.

  1. Display arrogance or lack of respect. People do not perform well if they feel undervalued.
  2. Stifle dissent. Leaders who cannot hear opposing points of view are bound to be unpleasantly surprised when reality contradicts their expectations.
  3. Feel threatened by people who are smarter or more effective than they are. A’s hire A’s. B’s hire C’s.
  4. Are lazy. They don’t make the effort to learn, to understand other points of view, to make the tough choices, to make sure the team is effectively executing.

  1. Self-absorbed – obviously “in the game” purely for their own personal gains at whatever costs.
  2. Aloof and irreproachable – convinced they “know it all” and actively avoid/suppress any dissension or questioning of approach.
  3. Unwilling to personally accept responsibility and unable to actively seek resolution to failures/problems.

  1. Too focused on numbers vs. quality product
  2. Recluse – don’t lead by example
  3. Fearful of competition

  1. All about them
  2. Talk the talk but don’t walk the walk
  3. Insecure, they do the opposite of surrounding themselves with good people

Why organizations succeed or fail:

  • Poor vs. good financial preparations
  • Good vs. bad business plans (or being inflexible when that plan needs to be modified)
  • Ego at multiple levels of the business

  • Fail – Aren’t close enough to the customer and/or market to understand it fully
  • Succeed – Focus on the 1 or 2 things that make them special (don’t get distracted with side projects)
  • Succeed – Hire the right people with the skillset and work ethic to accomplish the mission (across functions)


  • Clear vision
  • Resource to accomplish
  • Leader involvement
  • Reward subordinates who contribute. counsel those who do not
  • Eliminate those who, after efforts to teach and coach, still don’t contribute


  • All about the “leader”
  • Little about those down the tape
  • No clear vision
  • No leader involvement
  • Lead by threatening “leaders”
  • No achievable goals


  • Clear shared purpose and vision of the future (common goal)
  • Clear values that are never compromised
  • They continually re-invent themselves, completely understand their customers, and treat their employees and other stakeholders fairly and with respect.

Why organizations fail:  The three C’s creep in–they become Complacent, Conservative and Conceited (know more than their customers).

  • NIH – Not Invented Here
  • Provincialism.  This is the same as closed mindedness and is the hesitation or refusal to consider new stuff.  We’ve been doing it that way for years!  Why should we change?
  • Punishment of Failure.  If people are afraid of reprisal, they won’t try new things.


  • Empower their people – People perform much better when they feel they feel valued and respected, and have the ability to take initiative to accomplish their goals.
  • Promulgate a culture of action and accountability – Organizations that do not move fast enough or allow “dropped balls” will get killed by those who do not.
  • Embrace challenges and change – Change is a part of the human condition. An organization’s ability to identify where, when and what to change is critical. Its reaction to changes in the market, industry and society will determine its ability to survive and thrive.


  • Recruitment, motivation, and retention of a strong and diverse Team – if you have that, you can pretty much do anything.
  • A vibrant culture of always internally challenging and proactively questioning one’s assumptions, approaches, and directions.
  • Willingness to pivot and course-correct as necessary–accelerate through change.


  • lack of funding [Note: I strongly disagree with this one! I think that’s a symptom of another problem.]
  • wrong product for the market
  • product designed for the ego of the founders vs. the market needs


  • Have the right team
  • Have a plan
  • Ruthless focus on execution


  • They execute poorly
  • They don’t hold people accountable

Practical advice for leaders:

  • Make your bed every morning.
  • Pray regularly.
  • Know your competition.
  • Don’t be afraid to change your business plan. Adapt.
  • Make time for yourself and loved ones outside of work.

  • Be straight with your people – good or bad, give them the truth in a timely manner.
  • Invite others to be part of the team…give team members the opportunity to succeed or fail.
  • Find out what makes the company special and repeat, repeat, repeat.
  • Get through the decision making process as quickly as possible (without sacrificing good quality data) and move to execution – you can always tweak the approach later.

  • Know your team, key leaders, followers and worker bees.
  • Have a clearly stated vision/mission/objectives.
  • Provide the resources to accomplish the mission.
  • Be involved….care!
  • Follow up and reward success.

  • Lead by example, not by marching orders.
  • Communicate clearly and consistently.
  • Set the culture and enforce it. (Fire high performers that are not culturally aligned.)
  • Make sure you don’t run out of money.
  • Hire great people.

  • Great leaders do the following:  They build trust in their followers by being Competent and Credible, by always being Reliable so they can be counted upon, and by having high Integrity (consistently honest in their words and actions). But most importantly they build trust by putting everyone else before themselves. These leaders also seem to have a passionate and compelling vision as to where they want the organization to go in the future and are able to articulate this vision clearly and simply. Finally, they have a track record for getting RESULTS.
  • Never underestimate the importance of establishing the right corporate culture and ensuring it is aligned with your strategy! This is key to success!

  • Do not surround yourself with yes men or yes women. The best atmosphere to create is one in which the subordinates, no matter how junior, are not afraid to tell the boss he is full of shit.
  • Lead by example. You shouldn’t ask any of your subordinates to do anything that you wouldn’t do.
  • Hold your people accountable. Any time I set a deadline or let one of my people set their own deadline (or a target), I let them know that I was writing that down and that I would be holding them accountable to deliver. People respect what the boss inspects.
  • Make people get out of their comfort zone. This is especially true with salespeople. The best way to grow and learn is to be a little afraid (or a lot). The same old thing will probably deliver the same old results.

  • Think broadly and ahead. Always be looking over the next hill. Seek to be informed about the broader environment. Anticipate and make realistic judgments about opportunities and threats.
  • Focus, focus, focus. Flying in the face of my previous comment a bit, focus where you can win. “Boiling the ocean” is a plan for disaster.
  • Communicate, communicate, communicate. You can never communicate with your people enough, and by “communicate,” I mean both ways – imparting information and listening.
  • Always look for help, and offer it. No one does it alone. No major accomplishment happens through the efforts of a single individual. Actively cultivate a community of people who can offer you advice and support, and to whom you can offer the same.
  • Execute. A mediocre plan executed flawlessly will trump a brilliant plan executed poorly every time.
  • Always be learning, always be questioning. What you do not know will kill you.

  • Be honest and transparent (as much as practically possible). Customers, partners, peers, employees, investors, etc will always respect this, even if they don’t like the actual news/situation.
  • Be willing to accept that you can never “know it all” and constantly challenge your own thinking and biases.
  • Listen to all advice, criticism, inputs, etc from whatever sources — but then make your own decisions and ultimately own the responsibility of the outcomes involved.
  • Be a constant learner/student for your entire life – stretch/challenge yourself into new areas both vocationally and avocationally to broaden your perspectives in all that you do.
  • Make sure you are actually having fun and enjoying what you do. If you are not genuinely enthused, people will know it and will not follow you, support you, or be inspired to perform in the way that you desire. Also, you will eventually burn out.

  • Lead by example – be the best employee of your company.
  • Be passionate about your customer experience.
  • Believe in yourself.
  • Surround yourself with people truly smarter than you.
  • Seek mentors. You can’t be a leader without the sage support of others who have been there before you.

  • Learn what your individual strengths are as a leader. Play to those strengths, and build a team to address the weaknesses. Beyond that:
    • Build the team
    • Set the plan
    • Execute

Thanks to Steve for sharing the input he received from so many great people!

file under: Startups