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0 for 3: Edtech Startup Lessons Learned

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0 for 3: Edtech Startup Lessons Learned

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Andrew Gassen, CEO | Pivotal Software

0 for 3: Edtech Startup Lessons Learned

I’ve been a part of 3 different education technology companies, all focused on the K-12 market. Each of these companies failed, but each for different reasons and in spectacularly different ways. This talk is a bit of a public post-mortem that focuses on 3 key lessons from each company, including a brief discussion on how we might have done things a different way if I knew then what I know now.


Presented by the
Serious Play Conference
seriousplayconf.com
at
Orlando,
University of Central Florida,
UCF,
July 24-26, 2019

Andrew Gassen, CEO | Pivotal Software

0 for 3: Edtech Startup Lessons Learned

I’ve been a part of 3 different education technology companies, all focused on the K-12 market. Each of these companies failed, but each for different reasons and in spectacularly different ways. This talk is a bit of a public post-mortem that focuses on 3 key lessons from each company, including a brief discussion on how we might have done things a different way if I knew then what I know now.


Presented by the
Serious Play Conference
seriousplayconf.com
at
Orlando,
University of Central Florida,
UCF,
July 24-26, 2019

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0 for 3: Edtech Startup Lessons Learned

  1. 1. This is not a talk about failure. ANDREWGASSEN.IO
  2. 2. This is a talk to equip you for your journey. ANDREWGASSEN.IO
  3. 3. Hi! I’m Andrew Gassen. I teach at 2 startup accelerators in the DC metro area. I pair with Fortune 500 C-Suite executives and guide them on their journey to transform into modern software organizations. I’ve worked at 4 startups. Three no longer exist, one is in “zombie mode.” ANDREWGASSEN.IO
  4. 4. I teach people, teams, and companies how to build better software AND better software companies. ANDREWGASSEN.IO
  5. 5. I can only do this because of the mistakes I’ve made, the struggles I’ve experienced, and the successes in which I’ve been a part. ANDREWGASSEN.IO
  6. 6. Along my journey, I’ve encountered a number of forces capable of derailing a group of people on a mission. ANDREWGASSEN.IO
  7. 7. I want to provide you with my battle-tested playbook for identifying and eradicating these Agents of Chaos. ANDREWGASSEN.IO
  8. 8. In Today’s Session... 1. ✅ Set the Stage 2. Agents of Chaos a. What are they? b. How did they manifest? c. How’d we tackle them? d. How’d that work out? e. How to eliminate 3. Questions ANDREWGASSEN.IO
  9. 9. Agent Know It All ANDREWGASSEN.IO
  10. 10. Agent Know It All “You’re really smart, you can solve all these tough education problems despite having no industry experience or expertise.” ANDREWGASSEN.IO
  11. 11. Agent Know It All Infiltration Strategy ANDREWGASSEN.IO - Previous successes by key team members - Anecdotal experience by key team members - Poor customer research techniques - Find the Reality Distortion Field
  12. 12. Agent Know It All Impact on the Team ANDREWGASSEN.IO - Greenshifting - Skip customer discovery and validation - Built software “Because I said so” - Our direction ran counter to the market - Knowledge silos
  13. 13. Agent Know It All What’d I Do About It? ANDREWGASSEN.IO - “Think Harder” - Try to convince the customer that they’re wrong - Fire people who disagreed
  14. 14. Agent Know It All How’d That Work? ANDREWGASSEN.IO - Lack of customer adoption (aka no sales) - Competitors overtook us - Time and money wasted - Our reputation was being built in the market
  15. 15. How to Tackle Agent Know It All ANDREWGASSEN.IO
  16. 16. ANDREWGASSEN.IO 1. Get the team aligned on the desired outcomes 2. Reframe “knowledge” as bite-sized testable hypotheses 3. Agree on the indicators of success and progress 4. Do work, measure progress, as quickly as possible 5. Revisit, reflect, reframe, refocus Eradicating Agent Know It All
  17. 17. Sound familiar? ANDREWGASSEN.IO
  18. 18. ANDREWGASSEN.IO
  19. 19. Example ANDREWGASSEN.IO The Know-It-All We need a playlist creator tool that totally redefines lesson plans. Success Indicators ● All our requirements are done by start of school Getting it Built ● Wireframes + Mockups ● Debate, change, and internal sign-off ● Write all the code ● Make sure the code works ● Release it to production
  20. 20. Example, Reframed ANDREWGASSEN.IO Desired Outcome Provide a more efficient way for teachers to create lesson plans. Success Indicators ● >50% of teachers with access use our tool to build lesson plans ● Time spent building lesson plans in our tool is less than the observed baseline Potential Experiments ● Clickable prototype of our new playlist creator idea ● Provide starting templates ● Allow teachers to share lesson plans ● Made it easier to find vetted content ● Auto-filled a lesson plan based on a questionnaire
  21. 21. Agent Feature Factory ANDREWGASSEN.IO
  22. 22. Agent Feature Factory “It’s not ready yet, but once you build that next thing, THEN it’ll be ready.” Repeat forever. ANDREWGASSEN.IO
  23. 23. Agent Feature Factory Infiltration Strategy ANDREWGASSEN.IO - Lack of traction in the market - Inexperienced team - Fear - Poor development methodology
  24. 24. Agent Feature Factory Impact on the Team ANDREWGASSEN.IO - Mindset that more stuff = better - Constantly chasing, never driving - Lost sight of the actual outcomes we wanted to deliver
  25. 25. Agent Feature Factory What’d I Do About It? ANDREWGASSEN.IO - Set arbitrary milestones...that moved - Just continued planning and building
  26. 26. Agent Feature Factory How’d That Work? ANDREWGASSEN.IO - Products never got in the hands of real users - Super large set of unvalidated solutions - Sales expectations became unrealistic as R+D spend increased
  27. 27. How to Tackle Agent Feature Factory ANDREWGASSEN.IO
  28. 28. Don’t Pop the Bunny! ANDREWGASSEN.IO
  29. 29. ANDREWGASSEN.IO 1. Practice continuous delivery a. This is a huge, huge topic. 2. Build an outcomes-based roadmap a. But, like, actually use it 3. Understand where your value is 4. Adopt Lean Startup principles Eradicating Agent Feature Factory
  30. 30. Table Stakes Performers Delighters Lower Quality Higher Quality Happy User Unhappy User
  31. 31. App Metrics Utterance Support Codeless Builder Lower Quality Higher Quality Happy User Unhappy User
  32. 32. Agent Old School ANDREWGASSEN.IO
  33. 33. Agent Old School “If it worked 30 years ago, it will work now.” ANDREWGASSEN.IO
  34. 34. Agent Old School Infiltration Strategy ANDREWGASSEN.IO - Previous successes by key team members - Outdated education - Being “out of the game” for a while - Lack of real-world experience
  35. 35. Agent Old School Impact on the Team ANDREWGASSEN.IO - Doing things that contradict modern best practices - Unjustified confidence - Juuuuust enough progress to keep going
  36. 36. Agent Old School What’d I Do About It? ANDREWGASSEN.IO - ...nothing - Mutiny! New School vs Old School - Beat the drum of a wholesale transformation effort
  37. 37. Agent Old School How’d That Work? ANDREWGASSEN.IO - Everybody dug their heels in, as a matter of principle - Team trust eroded - Folks left - Decisions made based on allegiance, not value
  38. 38. How to Tackle Agent Old School ANDREWGASSEN.IO
  39. 39. ANDREWGASSEN.IO 1. Get a baseline of the current operations 2. Identify the top 1-3 areas to start tweaking 3. Collaborate and align on shared success indicators 4. Get little wins, one by one Eradicating Agent Old School
  40. 40. Agent Value Line ANDREWGASSEN.IO
  41. 41. Servers + Infrastructure Game Engine Project Management Tooling Programming Languages / Frameworks Version and Source Control Code quality improvement Development Methodology Availability New features Bug fixes Performance gains Release frequency Stability
  42. 42. Servers + Infrastructure Game Engine Project Management Tooling Programming Languages / Frameworks Version and Source Control Code quality improvement Development Methodology Availability New features Bug fixes Performance gains Release frequency Stability
  43. 43. Servers + Infrastructure Game Engine Project Management Tooling Programming Languages / Frameworks Version and Source Control Code quality improvement Development Methodology Availability New features Bug fixes Performance gains Release frequency Stability USERS CARE ABOUT THIS STUFF USERS DON’T CARE ABOUT THIS STUFF
  44. 44. Agent Value Line “Sure, A, B, and C are the most important, but it doesn’t matter unless you also do X, Y, and Z.” ANDREWGASSEN.IO
  45. 45. Agent Value Line Infiltration Strategy ANDREWGASSEN.IO - Made decisions based on technology, not product - Buzzword Bingo
  46. 46. Agent Value Line Impact on the Team ANDREWGASSEN.IO - Everybody was extremely busy, working very, very hard - Really neat (?) internal technology demonstrations - Progress seemed really slow
  47. 47. Agent Value Line What’d I Do About It? ANDREWGASSEN.IO - Honestly, nobody in our entire organization (myself included) viewed this as a problem. It was just business as usual.
  48. 48. Agent Value Line How’d That Work? ANDREWGASSEN.IO - Technical complexity went through the roof - New hires took a long time to ramp up and wanted to join the resume-driven development - So much output, so few outcomes
  49. 49. How to Tackle Agent Value Line ANDREWGASSEN.IO
  50. 50. ANDREWGASSEN.IO ● Use User Stories ○ As a teacher, I want ________ so that ___________. ● Use Job Stories ○ When ______, teachers want ________ so that _______. ● Prioritize that backlog ruthlessly ○ “How does this get us to our desired outcome?” Eradicating Agent Value Line
  51. 51. ANDREWGASSEN.IO 1. Align on why we exist and the key outcomes we need to drive 2. Map out the activities the team, not individuals, engages in 3. Estimate the time each activity takes 4. Prioritize areas where that time can be reduced 5. Empower people to make the changes Eradicating Agent Value Line
  52. 52. Story Time: Agent Fail Whale ANDREWGASSEN.IO
  53. 53. How to Tackle Agent Fail Whale ANDREWGASSEN.IO
  54. 54. Eradicating the Fail Whale Code Freeze isn’t the answer! Adopt modern processes! Come talk to me! ANDREWGASSEN.IO
  55. 55. The Double Agent ANDREWGASSEN.IO
  56. 56. The Double Agent “Look, this is how we do it over HERE, so you need to make your software like this, too.” ANDREWGASSEN.IO
  57. 57. The Double Agent Infiltration Strategy ANDREWGASSEN.IO - Partnership agreements with an imbalance of power and trust - Provide something we need and can’t get elsewhere
  58. 58. The Double Agent Impact on the Team ANDREWGASSEN.IO - Spent time doing things that ran counter to our perspective - Loss of morale; devaluation of expertise - Unintentional “stealth” mode - Turning down user feedback
  59. 59. The Double Agent What’d I Do About It? ANDREWGASSEN.IO - Technical shortcuts to get sign off - Compromises between businesses that impacted end-user experience - Anything they asked us to
  60. 60. The Double Agent How’d That Work? ANDREWGASSEN.IO - Never launched - Competitors blew by us - Partnership dissolved - Tremendous value left undelivered
  61. 61. How to Tackle the Double Agent ANDREWGASSEN.IO
  62. 62. ANDREWGASSEN.IO 1. Align on outcomes, not features or outputs 2. Be explicit about who owns what in the relationship 3. Be the expert in the areas of your expertise 4. Regularly check-in on progress toward key success indicators Eradicating the Double Agent
  63. 63. DROP ADD KEEP IMPROVE
  64. 64. Agent Hollywood ANDREWGASSEN.IO
  65. 65. Agent Hollywood “Who cares if you don’t have customers, look at how great those numbers are!” ANDREWGASSEN.IO
  66. 66. Agent Hollywood Infiltration Strategy ANDREWGASSEN.IO - Internal competition for resources - Output-based cultures - Low trust within the team
  67. 67. Agent Hollywood Impact on the Team ANDREWGASSEN.IO - Incentivized to stretch the truth to the stretchiest point - Wasted time and effort on vanity indicators - People chose sides - False sense of security
  68. 68. Agent Hollywood What’d I Do About It? ANDREWGASSEN.IO - Try to “catch” the “other side” - Be the better one-upper - Try win as many “awards” as possible
  69. 69. Agent Hollywood How’d That Work? ANDREWGASSEN.IO - Won awards! - Leaders (and entire teams!) left the company - All of our internal metrics were meaningless - Zero new customers
  70. 70. How to Tackle Agent Hollywood ANDREWGASSEN.IO
  71. 71. ANDREWGASSEN.IO Align 👏 on 👏 Outcomes 👏 Eradicating Agent Hollywood
  72. 72. ANDREWGASSEN.IO Measure 👏 What 👏 Matters 👏 Eradicating Agent Hollywood
  73. 73. Agent Tug-o-War ANDREWGASSEN.IO
  74. 74. Agent Tug-o-War “They’re wrong, you’re right, just go do your thing over there.” ANDREWGASSEN.IO
  75. 75. Agent Tug-o-War Infiltration Strategy ANDREWGASSEN.IO - Lack a common purpose - Poor prioritization - Low trust
  76. 76. Agent Tug-o-War Impact on the Team ANDREWGASSEN.IO - Teammates disappear for pet projects - “Us vs Them” mentality - Progress on core product grinded to a halt - Team spread too thin to do good work
  77. 77. Agent Tug-o-War What’d I Do About It? ANDREWGASSEN.IO - Pass it off as being a startup - Accuse people of not being team players - Accuse people of not being cut out for startup life - Recruit as many people to “my side” as possible
  78. 78. Agent Tug-o-War How’d That Work? ANDREWGASSEN.IO - Several incomplete, half-@$$ products - Cliques left all at once - Unhappy, or nonexistent, customers
  79. 79. How to Tackle Agent Tug-o-War ANDREWGASSEN.IO
  80. 80. An Unhealthy Team An unhappy prospect that isn’t a customer
  81. 81. A Healthy Team A Happy Customer
  82. 82. Agent Viability ANDREWGASSEN.IO
  83. 83. Agent Viability “Real startups have an office in Silicon Valley and specialized lighting and snack walls.” ANDREWGASSEN.IO
  84. 84. Agent Viability Infiltration Strategy ANDREWGASSEN.IO - Perceived peer pressure - Hubris - Ignorance (or lack) of key indicators - Silly expenses - Time to market is too long - No sales
  85. 85. Agent Viability Impact on the Team ANDREWGASSEN.IO - Visible stress on the executives - Product ADD / Spaghetti-at-the-wall - Focus on fundraising, not delivering user value
  86. 86. Agent Viability ANDREWGASSEN.IO
  87. 87. Agent Viability What I’ve Seen ANDREWGASSEN.IO - Say “yes” to anything with dollars associated - Layoffs - Constant pivots - Shut the business down
  88. 88. How to Tackle Agent Viability ANDREWGASSEN.IO
  89. 89. ANDREWGASSEN.IO 1. What metric matters most for the success of your company? 2. What’s your cost model? 3. How will you actually make money? 4. What are your unfair advantages? 5. What’s the shortest path to revenue? Eradicating Agent Viability
  90. 90. This was a talk to equip you for success on your journey. Questions? Connect with me...I love to talk! andrewgassen@gmail.com | www.andrewgassen.io | @andrewgassen | 407-307-6049

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