Douglas Squirrel

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About Douglas Squirrel
Squirrel has been coding for forty years and has led software teams for twenty. He uses the power of conversations to create dramatic productivity gains in technology organisations of all sizes. Squirrel's experience includes growing software teams as a CTO in startups from fintech to e-commerce; consulting on product improvement at over 70 organisations in the UK, US, and Europe; and coaching a wide variety of leaders in improving their conversations, aligning to business goals, and creating productive conflict. He lives in Frogholt, England, in a timber-framed cottage built in the year 1450.
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Blog postThe story of Stone Soup goes like this: you arrive in a village hungry and without any food in your backpack. The inhabitants are suspicous of strangers, so you start boiling water over an open fire. When passers-by inquire, you show them a stone that you’ve put in the pot, and announce that you are making delicious stone soup. This seems nuts at first, but you persist in singing the praises of this odd dish, and offer to share the meal once it’s ready. Then comes the kicker: you ask whether2 days ago Read more
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Blog postWhen I first began to lead tech teams at the turn of the century, I attempted to unify them against the “suits”. I’d describe myself as going in to battle for them against unreasonable deadlines and silly demands coming from “upstairs”, where the business leaders who paid our salaries and consulting fees lived. I painted us as merry rebels fighting for “best practises” like pairing and unit-testing, opposed senselessly by bean-counters who couldn’t understand our special tech wizardry. It was6 days ago Read more
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Blog postA client who is a recovering consultant marvelled when I introduced him to our methods for efficient, collaborative decisionmaking, joint design. “That sure isn’t how we did it at Bain,” he said.
I asked how they did do it at Bain, and learnt that their mantra is answer first. This is mostly wrong—but not completely!
The part that’s nuts is the idea that you can make an effective decision unilaterally first, and then rally others to help you implement it. There’s a problem wit1 week ago Read more -
Blog postThis is a transcript of episode 162 of the Troubleshooting Agile podcast with Jeffrey Fredrick and Douglas Squirrel.
We discuss two very different stories about leaders that communicate a cultural message pithily and clearly, and reflect on why these stories were effective and how all of us can communicate culture in this way.
Show links:
Steve Jobs aquarium story Listen to the episode on SoundCloud or Apple Podcasts.
Events Listen to this section at 00:14
1 month ago Read more -
Blog postThis is a transcript of episode 161 of the Troubleshooting Agile podcast with Jeffrey Fredrick and Douglas Squirrel.
If your boss isn’t helping like you think she should, maybe she’s not from Mars, but actually trying to give you more autonomy. We reflect on this in light of real-world coaching stories.
Show links:
Situational Leadership Listen to the episode on SoundCloud or Apple Podcasts.
Upcoming Events Listen to this section at 00:14
Squirrel: Welc1 month ago Read more -
Blog postThis is a transcript of episode 160 of the Troubleshooting Agile podcast with Jeffrey Fredrick and Douglas Squirrel.
A reader asks whether following the “bad idea” advice from last episode can lead to an unrecoverable local maximum, sentencing the team to endless patches and obscure bugs. Squirrel and Jeffrey have different takes on this based on their ancient greybeard stories.
Show links:
The Power of a Bad Idea episode Local maximum The Strangler Fig Application Lis2 months ago Read more -
Blog postThis is a transcript of episode 159 of the Troubleshooting Agile podcast with Jeffrey Fredrick and Douglas Squirrel.
Drawing lessons from Squirrel’s driving test experiences, we explore why making a cultural or process change that’s intentionally suboptimal can be surprisingly valuable.
Show links:
Driving Lessons episode Cynefin Kaizen Toyota Kata Listen to the episode on SoundCloud or Apple Podcasts.
Introduction Listen to this section at 00:14
Squirr2 months ago Read more -
Blog postThis is a transcript of episode 158 of the Troubleshooting Agile podcast with Jeffrey Fredrick and Douglas Squirrel.
We start with a listener question on roles in an agile team, but quickly divert to Squirrel’s “driftwood theory” of hiring and role specification, which turns out to be based on effective conversations and flexible problem solving (what a surprise!)
Show links:
We’re the Aliens episode Listen to the episode on SoundCloud or Apple Podcasts.
The Driftw2 months ago Read more -
Blog postIf you publish your roadmap, one of two good things will happen: your stakeholders will be happy and you can go forward, or you will learn that you got it wrong and you can correct it.
If you tell your team member that she’s not doing part of her job, one of two good things will happen: she’ll agree and work with you to improve, or she will disagree and you’ll learn she’s unwilling to improve.
If you tell your cofounder that your vision is different from his, one of two good t2 months ago Read more -
Blog postThis is a transcript of episode 157 of the Troubleshooting Agile podcast with Jeffrey Fredrick and Douglas Squirrel.
How giving work to your boss positions you as the driving force, not the bottleneck—and more methods and mindset shifts to change the perception “gee, that tech team sure is slow”.
Show links:
Squirrel’s workshop on “Decoding Tech Talk” Nudge book Radiate Intent, Elizabeth Ayer Art of Action, Stephen Bungay Listen to the episode on SoundCloud or Apple Po2 months ago Read more
Titles By Douglas Squirrel
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A successful digital transformation must start with a conversational transformation.
Today, software organizations are transforming the way work gets done through practices like Agile, Lean, and DevOps. But as commonly implemented as these methods are, many transformations still fail, largely because the organization misses a critical step: transforming their culture and the way people communicate.
Agile Conversations brings a practical, step-by-step guide to using the human power of conversation to build effective, high-performing teams to achieve truly Agile results. Consultants Douglas Squirrel and Jeffrey Fredrick show readers how to utilize the Five Conversations to help teams build trust, alleviate fear, answer the “whys,” define commitments, and hold everyone accountable.These five conversations give teams everything they need to reach peak performance, and they are exactly what’s missing from too many teams today.
Stop focusing on processes and practices that leave your organization stuck with culture-less rituals. Instead, unleash the unique human power of conversation.
Today, software organizations are transforming the way work gets done through practices like Agile, Lean, and DevOps. But as commonly implemented as these methods are, many transformations still fail, largely because the organization misses a critical step: transforming their culture and the way people communicate.
Agile Conversations brings a practical, step-by-step guide to using the human power of conversation to build effective, high-performing teams to achieve truly Agile results. Consultants Douglas Squirrel and Jeffrey Fredrick show readers how to utilize the Five Conversations to help teams build trust, alleviate fear, answer the “whys,” define commitments, and hold everyone accountable.These five conversations give teams everything they need to reach peak performance, and they are exactly what’s missing from too many teams today.
Stop focusing on processes and practices that leave your organization stuck with culture-less rituals. Instead, unleash the unique human power of conversation.
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