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Rethink Failure: Talking About Failure 
How to start a conversation about failure in your community, group, team, or company. 
Dedicate an hour or meeting to rethink failure -- here are questions and formats to start! 
Why this is valuable 
The convo is the point. Together, you’ll provoke thought, challenge assumptions, 
strengthen beliefs, create a safe space, and explore underlying fears or expectations. 
The tangible value of continuing the conversation and cultivating this culture are… 
-- increased openness on projects progress/results, leading to deeper critical questions 
-- sharing of tools and past experiences to foster greater success 
-- mental space and time to reflect and learn from action, rather than constant busy-ness 
-- confidence and comfort in a community that shares the good, bad, and uncertain 
-- more effective innovation, risk-taking, smart iteration 
Here’s a script you can adapt, followed by a breakdown of the topics, format, issues to 
look out for, and key facilitator tips. Ready? Let’s go! 
Today, we’ll rethink failure -- we’ll start a conversation, share, and perhaps rethink 
success. Thank you for being open to this idea. I think it’s a conversation we don’t have 
often enough, but affects our day-to-day communication, ideation, teamwork, etc. 
We can do two things, one or both: (pick one yourself, or have the team pick) 
1) share a failure story or what’s not working, and get listeners and/or feedback 
2) start with a question, for example, what does failure mean? 
What do you think? 
1. Failure stories. I’ll start. Since this is a safe space, let’s keep a couple things in mind. 
Share if you feel comfortable. If it’s about the past, try bringing out the humor in it -- 
there’s no better way to let go than to laugh. 
Let the team know what you want after you speak -- 
a listen, nod, and thank you; 
b notes about what they learned or that they’ve had a similar experience; 
c feedback and advice from their perspective. 
Notice if you are angry, blaming others, complaining etc, and just let us know in 
advance -- “I’m angry and a lot of what I say will sound like complaints.” 
2. Great! Let’s start with a question. Please share what comes to mind. (Pick a question) 
(If time is short, have people write down their feedback, advice, etc and deliver it). 
My takeaways from today are ____________. What did you learn or notice? 
Toolkit by RethinkFailure.com 
Co-organisers: Angela Ognev, Amelie Tan, Adele Sim 
Special thanks on this tool to Christian Geissendoerfer 
Questions? Write to angela@redesignahppy.com
How to start a conversation 
Feel free to mix or focus our two conversation approaches: question- and story-based. 
--Question-based starts with a curious theoretical question, and peers will contribute 
opinions and their own experiences -- this is a good way to start if team members are not 
yet comfortable sharing. 
--Story-based focuses on what’s going on right now, or previous stories, and is a process 
of sharing and, sometimes, responding. This is more intimate, and often more effective in 
creating safe vulnerable spaces, trust, empathy, and getting useful feedback or advice. 
Story-based (And/Or) 
Story-based sharing relies a lot on a structure that creates a safe space. One way to do 
that is to share a story in a particular way, and ask listeners to respond in the categories 
asked: some sharers will want advice, while others seek sympathy. 
First, explain the format and why you like it. (See script above) 
Share a story -- tell the group about the time when you failed, in whichever way failure 
means to you. Share something that didn’t work or isn’t working, or when you felt 
discomfort, uncertainty, hesitation, frustration, anger, fear, etc. 
Bring out the humor in it. There’s nothing like laughter to get over something that was 
tough, to let go add lightness to the situation. This is better for past situations than 
current ones however. 
Notice where you are blaming, complaining, confused, emotional, etc and let your 
listeners know what is happening there. This sets expectations and keeps conversations 
from becoming a sob fest. ie “Heads up, this story angers me, and that will probably 
come out in my language.” 
Ask for what you’d like -- should people listen, nod and thank you? Are you looking to 
hear about what they learned, if they have similar experiences, or if they have advice or 
tools you could use? Sharing immediately or writing on post-its/connecting later are both 
great options. Make sure you specify one based on your time-limits. 
Monitor the responses -- as people respond, make sure they maintained a safe space 
for you. If they try to problem-solve when you didn’t ask for it, please stop them and let 
them know that you are ready to be listened to, and not more at the moment. This is 
good. 
Toolkit by RethinkFailure.com 
Co-organisers: Angela Ognev, Amelie Tan, Adele Sim 
Special thanks on this tool to Christian Geissendoerfer 
Questions? Write to angela@redesignahppy.com
Invite the group -- have someone share their story. If needed, add prompts to help 
them. 
-- what is not working? 
-- where do you have uncertainty, hesitation, or didn’t meet goals/expectations? 
-- what have you done so far? 
-- how did/do you feel? what was the process like? 
Be curious! Stories encourage moral support, future resources, and willingness to take 
risks or grow in courage. 
And/Or Question-based 
Pick a topic that is important to an audience member, yourself, a teammate, or 
cultural/recent news. Explore that topic by defining words, looking for personal values, 
uncovering the root of beliefs by asking more questions. Be curious. Personal examples 
often come up, and be encouraged! Ready to jump in? start with story-based instead. 
Example topics/questions: 
-- what does failure mean? 
-- what does success mean? 
-- reflect on the idea that success must come after failure, that is good to fail fast or early 
-- how does the team react to things that are not working? 
-- how does our culture affect failure? culture can be from team, local, age group etc 
-- what do you do when you fail? 
-- what have you learned from past mistakes? 
-- where do your beliefs about failure come from? 
-- think about something that has been difficult to share. Why? 
-- what do you worry about? 
Any question is good -- just pick something that resonates with you. 
To keep the conversation going ask… 
-- what is an alternative perspective? 
-- who would like to expand on that? 
-- what does ___(word or phrase they used)___ mean? 
-- I hear that __(repeat key phrase)__. One implication I personally hear is __ (opinion)__ 
-- what are your thoughts on __(repeat the opposite of what they said)__ 
Remember to thank each contributor! 
Toolkit by RethinkFailure.com 
Co-organisers: Angela Ognev, Amelie Tan, Adele Sim 
Special thanks on this tool to Christian Geissendoerfer 
Questions? Write to angela@redesignahppy.com
Thank you for facilitating! 
Here are some tips for fantastic facilitation. 
-- repeat what you heard. “I’m hearing that…” Use same words or new words, but note 
if you’re using your words. This confirms understanding and comforts the sharer. 
-- ask open questions. Ask about the think, do, feel, etc of an experience. Watch out for 
yes/no questions, unless you are confirming what you heard. 
-- look for values and beliefs. Does this story show the person has high expectations for 
themselves, or that the expectations come from elsewhere? How do they define their 
experiences or thoughts? These may be things to uncover in a safe space. 
-- be curious. Ask them what their words mean. Make them think. 
--notice. question the phrasing, intonation, body language, random laughter, etc. Name 
it. It seems like you’re less energetic when you bring that up. What do you think?” “I hear 
pauses which makes me think you’re self-censoring. What is that? 
Issues & red flags … here are some things to watch out for! 
-- comforting -- “it gets better, look at the bright side, etc” This is another instinct that can 
be hurtful to people struggling with something. It dismisses their issue or makes it seem 
easy and unimportant. It’s done with the best intentions, but stop them and explain why. 
-- problem-solving. People do this instinctively. If someone bravely shares and wants 
people to listen, or to say what they’ve learned from their experience, stop the 
commenter if they start to make suggestions or advice,acknowledge what’s happening. 
-- emotions and tears -- stories are often hard to share. Don’t break down or back out. 
Watch out for pity. Be strong with them. Ask if they’d like to continue, smile. Thank them 
at the end, and if you’d like acknowledge the strengths or values you see in them. 
We look forward to rethinking failure and redefining success with you. 
Look out for the Rethink Failure conference in May 2015! 
Toolkit by RethinkFailure.com 
Co-organisers: Angela Ognev, Amelie Tan, Adele Sim 
Special thanks on this tool to Christian Geissendoerfer 
Questions? Write to angela@redesignahppy.com

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Rethink Failure: Starting a Convo in your Event or Team

  • 1. Rethink Failure: Talking About Failure How to start a conversation about failure in your community, group, team, or company. Dedicate an hour or meeting to rethink failure -- here are questions and formats to start! Why this is valuable The convo is the point. Together, you’ll provoke thought, challenge assumptions, strengthen beliefs, create a safe space, and explore underlying fears or expectations. The tangible value of continuing the conversation and cultivating this culture are… -- increased openness on projects progress/results, leading to deeper critical questions -- sharing of tools and past experiences to foster greater success -- mental space and time to reflect and learn from action, rather than constant busy-ness -- confidence and comfort in a community that shares the good, bad, and uncertain -- more effective innovation, risk-taking, smart iteration Here’s a script you can adapt, followed by a breakdown of the topics, format, issues to look out for, and key facilitator tips. Ready? Let’s go! Today, we’ll rethink failure -- we’ll start a conversation, share, and perhaps rethink success. Thank you for being open to this idea. I think it’s a conversation we don’t have often enough, but affects our day-to-day communication, ideation, teamwork, etc. We can do two things, one or both: (pick one yourself, or have the team pick) 1) share a failure story or what’s not working, and get listeners and/or feedback 2) start with a question, for example, what does failure mean? What do you think? 1. Failure stories. I’ll start. Since this is a safe space, let’s keep a couple things in mind. Share if you feel comfortable. If it’s about the past, try bringing out the humor in it -- there’s no better way to let go than to laugh. Let the team know what you want after you speak -- a listen, nod, and thank you; b notes about what they learned or that they’ve had a similar experience; c feedback and advice from their perspective. Notice if you are angry, blaming others, complaining etc, and just let us know in advance -- “I’m angry and a lot of what I say will sound like complaints.” 2. Great! Let’s start with a question. Please share what comes to mind. (Pick a question) (If time is short, have people write down their feedback, advice, etc and deliver it). My takeaways from today are ____________. What did you learn or notice? Toolkit by RethinkFailure.com Co-organisers: Angela Ognev, Amelie Tan, Adele Sim Special thanks on this tool to Christian Geissendoerfer Questions? Write to angela@redesignahppy.com
  • 2. How to start a conversation Feel free to mix or focus our two conversation approaches: question- and story-based. --Question-based starts with a curious theoretical question, and peers will contribute opinions and their own experiences -- this is a good way to start if team members are not yet comfortable sharing. --Story-based focuses on what’s going on right now, or previous stories, and is a process of sharing and, sometimes, responding. This is more intimate, and often more effective in creating safe vulnerable spaces, trust, empathy, and getting useful feedback or advice. Story-based (And/Or) Story-based sharing relies a lot on a structure that creates a safe space. One way to do that is to share a story in a particular way, and ask listeners to respond in the categories asked: some sharers will want advice, while others seek sympathy. First, explain the format and why you like it. (See script above) Share a story -- tell the group about the time when you failed, in whichever way failure means to you. Share something that didn’t work or isn’t working, or when you felt discomfort, uncertainty, hesitation, frustration, anger, fear, etc. Bring out the humor in it. There’s nothing like laughter to get over something that was tough, to let go add lightness to the situation. This is better for past situations than current ones however. Notice where you are blaming, complaining, confused, emotional, etc and let your listeners know what is happening there. This sets expectations and keeps conversations from becoming a sob fest. ie “Heads up, this story angers me, and that will probably come out in my language.” Ask for what you’d like -- should people listen, nod and thank you? Are you looking to hear about what they learned, if they have similar experiences, or if they have advice or tools you could use? Sharing immediately or writing on post-its/connecting later are both great options. Make sure you specify one based on your time-limits. Monitor the responses -- as people respond, make sure they maintained a safe space for you. If they try to problem-solve when you didn’t ask for it, please stop them and let them know that you are ready to be listened to, and not more at the moment. This is good. Toolkit by RethinkFailure.com Co-organisers: Angela Ognev, Amelie Tan, Adele Sim Special thanks on this tool to Christian Geissendoerfer Questions? Write to angela@redesignahppy.com
  • 3. Invite the group -- have someone share their story. If needed, add prompts to help them. -- what is not working? -- where do you have uncertainty, hesitation, or didn’t meet goals/expectations? -- what have you done so far? -- how did/do you feel? what was the process like? Be curious! Stories encourage moral support, future resources, and willingness to take risks or grow in courage. And/Or Question-based Pick a topic that is important to an audience member, yourself, a teammate, or cultural/recent news. Explore that topic by defining words, looking for personal values, uncovering the root of beliefs by asking more questions. Be curious. Personal examples often come up, and be encouraged! Ready to jump in? start with story-based instead. Example topics/questions: -- what does failure mean? -- what does success mean? -- reflect on the idea that success must come after failure, that is good to fail fast or early -- how does the team react to things that are not working? -- how does our culture affect failure? culture can be from team, local, age group etc -- what do you do when you fail? -- what have you learned from past mistakes? -- where do your beliefs about failure come from? -- think about something that has been difficult to share. Why? -- what do you worry about? Any question is good -- just pick something that resonates with you. To keep the conversation going ask… -- what is an alternative perspective? -- who would like to expand on that? -- what does ___(word or phrase they used)___ mean? -- I hear that __(repeat key phrase)__. One implication I personally hear is __ (opinion)__ -- what are your thoughts on __(repeat the opposite of what they said)__ Remember to thank each contributor! Toolkit by RethinkFailure.com Co-organisers: Angela Ognev, Amelie Tan, Adele Sim Special thanks on this tool to Christian Geissendoerfer Questions? Write to angela@redesignahppy.com
  • 4. Thank you for facilitating! Here are some tips for fantastic facilitation. -- repeat what you heard. “I’m hearing that…” Use same words or new words, but note if you’re using your words. This confirms understanding and comforts the sharer. -- ask open questions. Ask about the think, do, feel, etc of an experience. Watch out for yes/no questions, unless you are confirming what you heard. -- look for values and beliefs. Does this story show the person has high expectations for themselves, or that the expectations come from elsewhere? How do they define their experiences or thoughts? These may be things to uncover in a safe space. -- be curious. Ask them what their words mean. Make them think. --notice. question the phrasing, intonation, body language, random laughter, etc. Name it. It seems like you’re less energetic when you bring that up. What do you think?” “I hear pauses which makes me think you’re self-censoring. What is that? Issues & red flags … here are some things to watch out for! -- comforting -- “it gets better, look at the bright side, etc” This is another instinct that can be hurtful to people struggling with something. It dismisses their issue or makes it seem easy and unimportant. It’s done with the best intentions, but stop them and explain why. -- problem-solving. People do this instinctively. If someone bravely shares and wants people to listen, or to say what they’ve learned from their experience, stop the commenter if they start to make suggestions or advice,acknowledge what’s happening. -- emotions and tears -- stories are often hard to share. Don’t break down or back out. Watch out for pity. Be strong with them. Ask if they’d like to continue, smile. Thank them at the end, and if you’d like acknowledge the strengths or values you see in them. We look forward to rethinking failure and redefining success with you. Look out for the Rethink Failure conference in May 2015! Toolkit by RethinkFailure.com Co-organisers: Angela Ognev, Amelie Tan, Adele Sim Special thanks on this tool to Christian Geissendoerfer Questions? Write to angela@redesignahppy.com