David Cummings on Startups

Category: Leadership

  • Video of the Week: Simon Sinek – Why Leaders Eat Last

    Our video of the week is from Simon Sinek (author of the famous book Start With Why) on the topic Why Leaders Eat Last. Enjoy!

    From YouTube: In this in-depth talk, ethnographer and leadership expert Simon Sinek reveals the hidden dynamics that inspire leadership and trust. In biological terms, leaders get the first pick of food and other spoils, but at a cost. When danger is present, the group expects the leader to mitigate all threats even at the expense of their personal well-being. Understanding this deep-seated expectation is the key difference between someone who is just an “authority” versus a true “leader.”

  • The Ideal Team Player

    Patrick Lencioni is one of my favorite leadership authors writing books like The Advantage and The 5 Dysfunctions of a Team. His latest book, The Ideal Team Player, is focused on “how to recognize and cultivate the three essential virtues.” As always, he starts with a fable and then goes into more detail.

    Here are the three virtues and descriptions from the book:

    1. Humility – Humility isn’t thinking less of yourself, but thinking of yourself less.
    2. Hunger – Hungry people are always looking for more.
    3. People smarts – A person’s common sense about people…the ability to be interpersonally appropriate and aware.

    Looking to improve your leadership skills and build a better organization? Start by reading Lencioni’s books.

    What else? What are your thoughts on the book The Ideal Team Player?

  • An Executive vs a Manager

    Recently I was talking to an entrepreneur and we got into a discussion about the difference between an executive and a manager. Many people claim to be an executive, especially in the startup world, but they aren’t as common as claimed. While executives and managers both manage teams, there are several differences with an executive.

    Here are a few ways an executive is different from a manager:

    • Executives are more strategic and jump between long-term planning and short-term execution
    • Executives set the direction while managers run the day-to-day
    • Executives are more likely to push back and debate an idea
    • Executives often oversee multiple teams or departments while managers have one specific group

    An executive is different from a manager. Entrepreneurs would do well to recognize the difference, especially as the business starts to grow and scale (it becomes more apparent with time!).

    What else? What are some more thoughts on executives vs managers?

  • Get It, Want It, and Capacity to Do It

    In the book Traction: Get a Grip on Your Business, Gino Wickman talks about the people component of a business and shares several insights. One insight is how he assesses potential new hires or internal promotions against a simple framework called get it, want it, and capacity to do it:

    • Get It – Does the person understand the role and responsibilities? Does he or she “get” what’s expected of them?
    • Want It – Does the person have a desire for the position? Do they really want it or are they interested in it just because they feel it’s the next step in their career?
    • Capacity to Do It – Does the person have the ability to do a great job in the position? Or, is it likely to be a Peter principle case?

    The next time you’re interviewing someone for a position, go through the quick get it, want it, and capacity to do it exercise.

    What else? What are some more thoughts on the get it, want it, and capacity to do it idea?

  • 5 Next Steps After Raising a Series A

    After talking to, and working with, several entrepreneurs that raised a Series A round in the past year, I’ve come to better understand a few of the common next steps once the money is in the bank. For most entrepreneurs, raising a Series A is a full-time job such that once it’s done they want to dive back into the business. Only now, expectations and complexity have gone up.

    Here are five next steps after raising a Series A:

    1. Choose a System to Manage the Business – To get the business to the point that you were able to raise a Series A required a level of planning, communication, meetings, and more. Now, it’s time to choose, and institutionalize, a methodology to run the company as it scales to the next level.
    2. Build the Weekly Operating Metrics Spreadsheet – Everything in the business needs to be well instrumented with clear OKRs/goals and a strong weekly operating metrics spreadsheet covering every KPI in the business
    3. Hire an Internal Recruiter – 80 – 90% of the new capital is going to go towards hiring people. Bring on someone in-house to recruit directly as well as interface with external recruiters for the hard-to-find positions.
    4. Find a Venture Debt Provider – Venture debt is one of the most cost effective and least dilutive ways to grow a startup. After raising a Series A, banks like Silicon Valley Bank and Square 1 Bank will be eager to offer a line of credit or a term loan.
    5. Join a Peer Group Like YPO or EO – Growing a business is hard. Very hard. Join a group of like-minded leaders that are looking to learn from each other.

    Raising money is simply a milestone in a long journey, not the destination itself. Follow these five next steps after raising a Series A and set the foundation to achieve the next level.

    What else? What are some other next steps after raising a Series A?

  • Video of the Week: Meetings that don’t suck

    Our video of the week is from Google Ventures titled Startup Lab Workshop: Meetings that don’t suck. Learn a variety of best practices for different meeting types, the difference between deciders and reviewers, the power of agendas, and more. Enjoy!

    From YouTube: Google Ventures Startup Lab | This workshop focuses on what makes for a good meeting, what kinds to avoid, and how to run them effectively. Meetings can suck the life out of a startup, and can prevent teams from executing. When done correctly, meetings can keep everyone informed, help the company move more quickly, and identify and resolve obstacles.

  • Weekly Confidence Rating for OKRs

    Another topic from the book Radical Focus: Achieving Your Most Important Goals with Objectives and Key Results that stood out to me is the idea of a weekly confidence rating for the OKRs. The idea is that every week whomever owns a key result reports on their confidence that they’ll achieve it on a scale of 1 to 10 with 10 being 100% confident (e.g. a value of 5 / 10 would mean 50% confident that the key result will be met).

    Think about that for a minute: how often do you do a serious gut check as to whether or not you’re going to hit your current goals. Weekly? Monthly? Never? This idea of not only assessing the confidence that you’ll hit the key result but actually quantifying it on a weekly basis is great for team alignment and communication. How often have we heard someone give regular updates about their project or goal only to realize too late that they’re not going to hit it?

    The next time you really want to drive accountability and clarity in your organization, ask for a confidence rating for each goal’s metric or objective’s key result and track it on a weekly basis. Watch as things improve and people are more focused.

    What else? What are some more thoughts on weekly confidence ratings for OKRs?

  • You’re a Systems Guy

    Yesterday I was talking to an entrepreneur about different leadership methodologies and he looked at me and said, “you’re a systems guy.” Hmm, I thought about it for a second. Yes, I’m a systems guy. Then it just came out of me, “I love systems because I don’t have to think.” Of course, there’s a ton of research and thinking to come up with the system. But, once it’s in place, I know that it’s helping get things done and I don’t have to worry about it.

    Over time the systems have to be tweaked and enhanced, but just the fact that the system is in operation and working means that it’s better than before. Now, I’m not advocating for bureaucracy. What I am advocating is making sure that things run in a sustainable, repeatable manner thereby delivering the desired outcomes.

    Some systems that I like:

    My advice: pick a system and run with it. Don’t wait for the “perfect” system when there are plenty of good ones already out there.

    What else? What are some more thoughts on being a systems person?

  • The 4 Quadrant Weekly Alignment Doc from Radical Focus

    Continuing with Radical Focus: Achieving Your Most Important Goals with Objectives and Key Results, the author shared a really interesting approach centered around a simple document for weekly alignment and accountability. The document, called the Weekly Check-in, is composed of four quadrants on one single page that represent key items to track and/or discuss.

    Quadrant 1

    • This Week’s Priorities
      • Labeled P1 or P2 for top priorities and secondary priorities
      • Things that aren’t P1 or P2 aren’t included

    Quadrant 2

    • Objectives and Key Results
      • 2 – 3 Objectives
      • 3 Key Results per Objective
      • 1-10 likelihood of hitting each key result with 10 being the best (e.g. 5/10 would mean 50% confidence)

    Quadrant 3

    • Next 4 Weeks
      • Big items on the horizon
      • Things everyone needs to know are coming

    Quadrant 4

    • Health Metrics
      • Key performance indicators for the business
      • General metrics that might or might not tie into the OKRs

    This process is easily translatable into a Google Spreadsheet or a dynamic system that automates it. Regardless, leaders would do well to implement a system with a weekly review of both the near-term tasks and longer-term OKRs/goal.

    What else? What are some more thoughts on the four quadrant weekly alignment document from Radical Focus?

  • The 4 Disciplines of Execution: Achieving Your Wildly Important Goals

    After having several entrepreneurs recommend the book The 4 Disciplines of Execution: Achieving Your Wildly Important Goals (4DX) to me, I finally got around to reading it. Quick review: it’s awesome and every entrepreneur should spend the $11 to buy it on Amazon. Here are the four disciplines:

    1. Focus on the Wildly Important
    2. Act on the Lead Measures
    3. Keep a Compelling Scorecard
    4. Create a Cadence of Accountability

    Imagine taking the core execution elements of Mastering the Rockefeller Habits or Traction: Get a Grip on Your Business and distilling it down into four disciplines and you have the 4DX book. This is important because the disciplines are all attainable and there’s less touchy feely stuff that turns some people off from the other books (e.g. I love core values and culture stuff but some people see that as being beneath them).

    Here the four disciplines rephrased into simpler terms:

    1. Make no more than one or two very important goals with a clear metric and deadline
    2. Track two or three metrics that are leading indicators for the goals (e.g. if the goal is to sign 100 new customers, a leading indicator would be number of qualified opportunities in the pipeline)
    3. Develop a spreadsheet or report for everyone to see that has the leading indicators and goal metrics (real-time, if possible)
    4. Meet once a week for 20-30 minutes to talk about what was done the previous week and what will be done the next week to hit the targets (accountability!)

    Seriously, every entrepreneur should buy the book and run this process (a couple critical goals, leading indicator metrics, central dashboard with the metrics, and a short weekly meeting talking about actions to hit the metrics). I recommend The 4 Disciplines of Execution.

    What else? What are some more thoughts on the book and the four disciplines?