1:10 Raymond recounts his first real experience in entrepreneurship, telling about the “driveway car wash’ he owned with his friends.
1:33 [On lessons learned from this early venture] – “One of the lessons was the operating costs are always higher than you think they are.”
1:50 “Any industry worth being in is crowded.”
2:15 How law school taught Raymond to show up in the world in a professional way.
2:53 “My education in law school really helped me write with some structure, rather than just stream of consciousness, but to actually put one idea after the next in a way where something builds.”
3:05 “A lawyer is able to string a series of good ideas together and build an argument, right? Which is what a good book or a good blog post is: it’s a good argument for advocating a a piece of change.”
3:45 Raymond describes what it was like working 3 jobs out of law school, and still barely being able to cover rent.
4:04 [Paraphrasing Andy Warhol] – “You know you’re on track in your life when you’re using the best and the worst of what’s happened to you over the course of your journey.”
4:26 “If I want to have an impact in the world, I’m going to have to take some steps, and there’s going to be some painful moments along the way.”
4:52 [On Raymond’s Clients at Refound] – “I think the biggest problem we help people with, I would say, is overwhelm and ambiguity.”
4:55 “In most modern organizations, there’s a lot of thought being put into ‘How do we create a people first culture? How do we engage with employees? How do we create the conditions where people feel like they’re coming to work not just to create profit for owners and shareholders, but a sense of personal meaning.”
5:27 “What we’ve been able to do is offer a real tactical approach for how to do, in particular, feedback and accountability in an organization that really grounds the way people operate on a day to day basis.”
5:53 “Where organizations go sideways, and where things start to degrade, is in the actual conversations between managers and employees, between managers and one another, and, very importantly, between managers and senior executives.”
7:39 [Case Study Software Company in south bay, CA] – “There was this big aha moment, which is fairly common, where all of the managers in the organization [realized] how they were sort of playing a level down or two levels down from their title.”
8:26 “It’s incremental. Nothing changes overnight. Nothing worth doing changes overnight.”
9:09 “And that’s really the best part of this work for me. I get to see people take these tools and apply them in ways that I never would’ve thought, and have conversations that are meaningful to them.”
9:44 [On Raymond’s inspiration for writing the book] – “I bumped up against my own capacity as a leader, and I realized that I didn’t know what I was doing.”
10:23 How Raymond’s experience with cold, unfeeling training programs led him to create a work that was truly human.
10:26 “It’s not about being authentic, because “being authentic,” well, what does that mean? But, you know, how do you show up in a way that’s both professional and personal, that’s warm and kind and compassionate, but that also drives results?”
11:15 The type of feedback that makes people uncomfortable, and the scourge of the “Millennials boogeyman.”
11:57 [On the reluctance to new processes and change] – “People have been burned before.”
12:31 “This points to the tragedy of what’s happening right now in otherwise really interesting space in time, is that we’re radically over investing in technology to solve this problem, and radically underinvesting in training.”
12:59 [The mistake organizations make again and again] – “Buying tools and technology to solve human problems.”
13:39 Why managers are so hesitant to give feedback.
14:24 “To be able to embrace a communications methodology that says, ‘Actually, you know what, uncertainty is your best friend.’”
14:40 “If your feedback provides a solution, it’s not feedback, it’s micromanagement.”
15:12 “When we get a solution, when we get a ‘Here’s what you should do next,’ it’s quite disempowering.”
16:15 Raymond reveals some tips for managers.
16:25 “There are very few things we can do that will give us more value than not going into feedback situations cold.”
17:26 [On Accountability] – “We have to reframe what we think of when we say accountability. We can use the word, but if we don’t understand the meaning behind the word, we’re on the wrong track.”
18:07 “Accountability, all it means is responsibility for one’s actions.”
18:35 Why accountability without consequences is ineffective.
19:14 “Accountability is a gift.”
19:50 Raymond shares the layers of developing accountability in an organization.
20:25 [The key to accountability] – “The key is communication where people say, ‘You know what? I’m holding myself accountable for this, and you, Sir or Ms. Manager, I want your help.”
21:13 “We’re not very mindful as a species, we tend to be kind of reactive.”
21:35 How to “name what we feel” when giving constructive feedback.
21:58 “We can’t change behavior if we don’t know what the behavior is.”
22:33 “People will surprise you.”
22:47 “Oftentimes that’s what we need, we need boundaries. We need structure for what does excellent work look like.”
23:25 “If you get to do whatever you want, whenever you want with no consequences and no structure, you’re not really helping your teammates, you’re not really helping the organization in any directed, vision oriented way.”
23:44 “A good sales conversation has structure, it has flow – you have pieces that you want to cover; but it also has substance – it’s how you show up, and how you relate, and how you listen.”
24:49 How structure, communication, and substance go hand in hand.
25:37 “What unifies the organizations that are doing this well is participation from executives in a very specific way.”
26:10 [On the importance of recognizing where we are.] – “We’re very good at making big pronouncements of how it’s going to be in the future.”
27:14 “You actually have a lot more latitude, a lot more leeway with the people in your organization than you think.”
27:25 “You don’t have to fix the organization this afternoon. You just have to own that there are problems.”
27:49 “The frustration comes from when management and leadership tries to whitewash [problems].”
28:26 “I think it’s interesting that organizations have found themselves in this position of having to apologize for holding people accountable for being jerks.”
29:49 The problem with taking half measures.
31:12 “Don’t boast about what you’re going to do, let actions speak for themselves.”
32:05 What Raymond reads to stay on top of current trends.
33:02 The tools Raymond uses to stay productive.