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Part 2 - Coaching, Delegation and Trust

with Darian Shimy

June 30, 2020
Part 2 - Coaching, Delegation and Trust
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Darian Shimy - Engineering Lead @ Square

As an engineering leader who scales teams and products, Darian Shimy is an industry veteran with over 25 years of experience. He is currently at Square with prior leadership positions at Weebly, Attensity, and He received an MS in Computer Science from The University of Southern California and continues to code as a hobby. Outside the professional setting, Darian is a softball coach for various age levels from the recreation to competitive level.

"When someone comes to you and says, 'is this okay? Can I do this?' They're implicitly removing the accountability and responsibility from that decision."

- Darian Shimy


  • How to scale leadership through effective delegation (1:40)
  • How to create environments of trust, ownership, and accountability (5:25)
  • The power of repetition in communication and how to get feedback on your message (13:11)
  • How trust saves you time and creates leverage to scale (15:26)
  • Improve communication by adjusting your style and asking more engaging questions (22:15)
  • How to reduce fear and increase team input in large meetings (27:37)
  • How to read the room: what cues and signals you need to pay attention to (33:11)
  • The leader who most inspired and impacted Darian (36:20)
  • The simple power of smiling (38:31)


How to scale leadership through effective delegation

Patrick Gallagher: I think in talking about scaling leadership, one of the things that leaders oftentimes say is that , we need to work ourselves out of a job. And, and you've shared a little bit about the intention of how to make that happen. So what do you do after you work yourself out of a job? Like, should you be worried about job security? Like what happens then?

Darian Shimy: Yeah. So that, that happens a lot because like , and I think it's just what people, you know, what yard stick they're using, what they use to measure their value to the organization. But you know, when you're an individual contributor, it's really easy to see your impact. Right? You'll get, you'll get a task, you'll write some code, it'll go out and production. You'll see customer usage, you'll see metrics and everything go up. And it's like super easy at that point. When you move over to a manager, You're not producing these artifacts like you were before. Right. And it's very different.

You're like, "well, I'm not making this stuff. Maybe my team doesn't need me. Maybe I should fill my day with things so I look busy. Right. But when they do that, they end up not delegating . And what they need to do is they need to understand so like from a delegation and value standpoint,

I tend to have like three levels of delegation. Like the first one is you're going to delegate work. You're going to delegate tasks. This was like year and a half, a mountain to climb and you're gonna have your team come in and you're going to give them the things they need to do to be successful. .

And then once you start managing managers, then it's, well, I'm now responsible for the project. And my goal is to make sure this project is successful. And I may be working with multiple teams to make that happen.

And then at the third level, your responsibility is a business objective . you have a metric that you need to drive to, and nobody cares about the projects that are happening.

They care about the metric. Right? So from, and what I tell my managers is like, what I'm going to measure you on is this task. This. Project or this metric. Like your goal may be to increase conversion by 25 basis points over the quarter. Do I care about how many projects you get out to get that done? I don't. I just want you to hit that target.

And once they start understanding that this is how they're measured, right. And I don't, I care less about their day to day. Then they can start focusing on getting people aligned to make that happen. And I say, you know, your value is , getting the projects done to achieve a result. And that, tends to remove the, I have to still be an IC as a manager.

More specifically a manager's goal is to , basically delegate their job away, right? When they do that, they help people grow as we already talked about, and also they need to be able to step back.

So for me, what I tell people is the sign of a great manager is one who can walk away and the ship can continue sailing. I said, if you had to leave today for six months, what would happen to your teams? Would they fall apart? Or will they continue to execute? It doesn't mean everything will go perfectly well because what managers tend to do is they tend to be the ones that work on problems when there are problems.

So I tell a lot of my teams, I say, I have about 12 teams that are underneath me. And I say, look, I have a lot of teams as if you don't see me. It's not that I don't care. It's that you don't need me. I said, I tend to spend my time where it provides the most value that organization. And it's usually when there's hotspots and problems or a very high profile project.

So I say, if I'm not there, it's okay. That probably means you're doing a great job. See if you see me a lot and I'm asking a lot of questions. There may be a problem, right? You may, I may be nervous about something.

So from my standpoint, you know, I say for a manager, like their goal should always be able to walk away, make sure who's going to pick it up when you're not there. Who's going to be able to continue with the culture, continue with the quality, continue with the motivation, kind of keep everybody going throughout the entire thing.

How to create environments of trust, ownership, and accountability

Patrick Gallagher: if the goal is to, to be able to walk away for, for six months, some of the things I think about is there's a lot of trust in that, like , if you're helping empower people in a way where they can step away for six months and then the ship will run without them, there's a significant amount of trust involved with that. And I think part of that is then the ability to have real conversations and to tell exactly what's going on. So do you have any thoughts about how to make your team share their real thoughts or their real concerns or provide real feedback with you or to share that disagree, like thinking from a coach coaching perspective?

Like if you make a, if you make a call that they don't agree with and you've got player resentment?

Darian Shimy: Oh, absolutely. Yeah. Yeah. So, I mean, let me put it this way. Let's say you had an intern in a meeting with the CEO of a company, any company, and the CEO says, "this is what we're going to do."

Do you think the intern is going to go and say, "excuse me, that's a bad idea."

Probably not. You know, when I'm in my meetings with people. I try and get them well, there's two ways. So usually in a smaller, more intimate setting, I try and help them understand early on. And I say the same thing all the time, and I kind of say it in jest, but I truly mean it. And I say, I have a lot of bad ideas. It's your job to let me know what they are. Right. I immediately tell them I want them to criticize me. Like I want you to know when I'm off base. When I make a mistake, when I'm wrong. and I say, feedback is a gift and I value it deeply.

so I never, whenever anybody comes to me, some people come to me with anger. Some people come to me with frustrations. Like, I can't believe you said that? And sometimes I'll explain, like, this is what I was thinking. I'm like, I know you don't like the outcome, but this was my intent going into it. You know, other times I'm like, "wow, I didn't realize that would bother you so much. I apologize. I'm sorry. I just, I didn't see that happening." And I always thank them for the feedback that they give me.

Not everybody does that. Right. Everyone has a different type of personality. And what I found also is like, especially on a brainstorming session, you know, writing is a great equalizer. Sometimes in meetings, if we're just talking, I will throw out an intentionally bad idea to let people know in this brainstorming session I want any idea coming out, right? I'm like, well, if our lead just said, t at I can say anything, right? It doesn't have to be a well baked idea. And again, it gets to that emulation of behavior that's rewarded.

but it is super important to have that trust and that accountability. And, you know, one of the things that's like, how do you end up building that trust? And you know, a lot of times there, there's some subtle things that happen that I see and, you know, you'll, you'll have an IC come to manager say, "is it okay if I do this?"

You gotta be really careful how you answer.

So in California, when you get your driver's license, right? When you turn 16, they say, you know, state of California says "you can drive a car, but you can't really have anybody under the age of 21 in there with you" right? Unless you have a parent in the front. This is a law that may not be fully followed by everybody...

So my daughter called me after getting her license and this was a couple months in and she's in and we live in a fairly suburban area that, you know, traffic is not very big. I mean, the city of Pleasanton doesn't even have a single parking meter type of thing.

And we live about a mile from the school. So she asked me, you know, "Hey, is it okay if I drive my friend home today?"

And you know, I had my opinion on it and I thought about it and I said, "If I answered this question. Yes. I said, if I say you can drive and something bad happens. I own that outcome."

What I ended up telling her was I said, "state of California trusts you to drive. I trust you to drive. You're going to have to make decisions throughout your driving career. You're gonna have to decide whether you're going to speed or not. Whether you are going to park illegally while you'll come to a full stop or not?" I said, "I'm not always going to be there." I said, "you have to make the call, but when you make the call, you have to own the outcome. You're the one who's responsible for it, not me."

And I'm not going to tell you what she decided, but she did make a decision. And she did own it. And it's the same thing when someone comes to you from a management standpoint says, "is this okay? Can I do this?" They're implicitly removing the accountability and responsibility from that decision.

So what I will typically answer is I don't see anything wrong with it. Let me know how it goes ? I'm not giving them approval. I'm not giving them a stamp to say, "Hey, I don't have to worry about it anymore." They have to worry about it. They have to own it. and that's when you start building the trust.

And they say, I'm telling them, I trust you to make this decision. And it's empowering for them to feel that, and they'll tend to own the outcome. And then once you start building this trust over and over again, you hope that they won't be coming to you every time. My daughter has never come to me with a driving related question on the law since then, because she knows what the answer is going to be.

When someone comes to me with a design I'm like, "Hey, you need to go vet this with other people, get everyone else to sign off. and I'll probably be okay with it at that point." Right?

So it's like, it's like, what do they need to do to build consensus? What do they need to do to help understand the direction that they're going to go? Let them own the outcome, let them own what will come from their direct actions instead of delegating that responsibility to their lead.

Patrick Gallagher: This feels really relevant and personal to a lot of the conversations that Jerry and I have. I was hoping to get your thoughts on how do you distinguish between empowering people in that way and helping them own the outcome and then providing constructive feedback or direction on a project or outcome. Cause I think for Jerry and I, this is oftentimes where I think we get gray and, and confused ...

Darian Shimy: Yeah. So like as a lead, there... and again, I think it's, if you scale your team out, so don't think that you have five, I think you have 50 or even 500 people working for you. And it's like, what would be your level of involvement?

Your level of involvement at that high level is strategic. It's not tactical. So you want to push as much tactics down and let the team work on it. And this is, you know, Jerry and I have talked about process in the past and you know, I'm, I don't like dictating process. I like the team to find the inefficiency and come up with process themselves. They'll, it'll tend to be much lighter weight and they'll tend to own it and not resent the fact that I'm telling them, make them go through this bureaucratic tape to get something done.

Well, you guys came up with it. If you don't like it, you guys change it. It's not mine. Right. It's to make YOU more effective. Right. so, you know, when I look at something, I want to make sure it's in line with our strategy. Right? So someone if came to me and said, here's my design doc. And I'm like, well, this is using a whole set of technologies that were, we really don't want to adopt.

And here's why we can't go down that path. And that's where I'm going to put up a few... you know, I don't want to say roadblocks, but bumpers ... again, this is where you're trying to direct that energy and say like, you need to work within our frameworks. You need to work within our timelines. You need to work within our budgets. Right. That's what I have control over.

But how you actually go about implementing it? Like the team has to own that. You guys have to be the ones, you know, I'll put some constraints, just like driving. We put some constraints or some time there's a car is how far you can go and stuff like that. And it's the same thing on projects right? Here are your constraints. Here are your walls that you have to work in the parameters, but it's up to you to figure out how to get these things done.

And it may not be the way I would have done it, but it doesn't make it wrong. There's a lot of different ways to achieve a result. It may not even be the optimal way, but it might be good enough.

They say, that you should focus on the things that matter most. and if there's a lot of little details out there that I don't concern myself with it's okay. Right. I don't have to be in the nitty gritty of every little thing going on. You need to trust the team because this is when they have the safe space to make a mistake. And they have a mistake to grow.

Like maybe that library, wasn't a good idea. Maybe I didn't vet it properly enough. Or, you know, when I, when I actually started implementing it, had all these other issues, I didn't check the performance. There's a lot of things I can come up with. That you may not even be able to, to see in a design doc or when someone's communicating to you, but when they own it, the next time, they'll say, "well, I got bit by this. You know, now I have the experience to go forward."

The power of repetition in communication and how to get feedback on your message

Jerry Li: So there's a notion of, the WHAT and HOW so the manager controls the, WHAT you can provide a lot of guidance on that, but give the freedom to the team to decide the HOW.

Darian Shimy: Absolutely, absolutely. You know, the tricky part is when you disagree on the what?

Jerry Li: Yep.

Darian Shimy: Right. And that, that, that's where it takes, you know, maybe some salesmanship.. . To really present it in a way that resonates and, you know, like anything practice makes perfect. When I have a new direction or strategy, I don't go to an all hands meeting to say, this is what we're doing. I will tend to go to one person. You know, that I trust that I know will give me raw, honest feedback and say, let me run something by you.

And I, and I, I give my speech and they're like, "wow, that just didn't resonate..."

I'm like, okay! Let me try again and try again."

And you keep honing your message over and over and over again until you get it right.

I mean, communicating is a skill. Just like batting, pitching, throwing anything else. It's something that you have to continually exercise. You have to continually get better at and you have to continually home throughout your career. You're never going to be perfect at communicating. You don't know what people are going to respond to.

And especially when you're talking, when you're talking one on one, you get to read their feedback. Right. I can see their eyes. I can see their body temperature. I can see a lot of things going on right there. And as that starts to grow, it becomes harder and harder. If you're talking to you know 50, 500 people... you're looking out in the crowd, you can't even see everybody. You don't know if they're listening or not. People in the back are probably on their phones doing something entirely different. "Well, I'll, I'll watch a recording later, right. At twice the speed."

So, you know, it's one of those things that, you know, honing your message helps a lot, and it really helps, you know, you want to make sure that it resonates with, a variety of people.

So I would say like, Also when, when you're working on your messaging, make sure that you're not just talking to the same people over and over again, not talking to the same seniority of people. Make sure that the person who may not have heard the full strategy earlier, here's it now.

And you know, being repetitive, you know, there's this thing in technologist says, don't repeat yourself, right? Where do you want to reuse code and everything like that. In management, that was the worst thing possible. You want to repeat yourself over and over again, over and over and over and over and over again. There's no end. You, you need to say the same message over and over again. So it sinks in. They need to be able to recite what you've said over and over again. And getting people to be able to basically replace you on the messaging should be the goal, right?

One of the things that I think Apple has done an amazing job of is they've made everyone who buys their product, a salesperson. They all say, Oh, look at the retina display. Okay, sure. I'm on the other, you know what that is? But she'll, she'll say it. She understands it. She knows it's valuable. And it's the same thing here. You get everyone to start... They all get the talking points from hearing you and they can start reciting these talking points. Right. And they can start, you know, telling other people.

And then once you have the organization that is able to do that, then they really understand the strategy. They really believe in it. And they're really going to help execute towards that. Even if it goes off the path a little bit, they'll stay within the bumpers. But you know, it's a path to get from point a to point B that really matters.

How trust saves you time and creates leverage to scale

Jerry Li: And going back to the process question, I remember in an earlier conversation, you shared a really interesting example of how you simplified the process of filing expenses. and that just gave a really good story people can emulate in the future. So, do you, do you mind if you...?

Darian Shimy: yeah, so I don't want to get myself in any trouble here, but there's certain things that, you know, will help instill trust in people.

And I remember, this was back at Weebly. We gave everybody a credit card. You got a company credit card with very little restrictions or policy on anything that what to do with that and have people come up, "Hey, I got this credit card. What am I supposed to do with it? I'm like, well, you need to make that call . And so you're welcome to ask me if you're not sure, but you need to make the decision. I'll say it's not for personal it's for business use, but beyond that, You're the one that needs to decide whether this business use is important or not."

I have people today come up to me, go, "I want to go to a conference..."

And it may not be perfectly fitting on. Like, if this is business related, it's approved. Don't worry about it. They don't have to justify it to me. They don't have to explain it to me. I said, "I'm trusting you that if you're going to go and say, this is business related, it's business related."

I haven't had anyone abuse that I haven't had anyone trying to take advantage of it. I think they... when you, when you put up a lot of process, that is... designed to prevent people from abusing something they're going to try and either push to the limit or figure out a way around it, find a loophole, something like that. But when you give this implicit trust, it's just an incredible amount of trust. It becomes almost a burden, at some point... they don't want to violate it. Like the company trusts me with X, Y, and Z. And I want to make sure that I don't violate that. And they're going to, they may even you know optimize farther away from it.

You know, it's like, well, a book, yes. I need a book to do my job. Nobody's going to argue with me buying a book, but do I really need it? Can I, is there a book on the shelf I can use? Is there an online resource? Like maybe they're going through this head, maybe it's not, I'm not sure... But I tell people make your decisions as if you own the company. and if you, if you need this to be successful, then you have to get it right. There shouldn't be any question about it.

But it's that understanding and trust and it's little things like that. There's other things like, even with travel policy, someone says, you know, I said, well, I'm going to give you implicit travel. You know, if you need to go to another office, you have to go to the other office. You don't have to ask me every time.

I tell people, don't tell me every time you take a day off ... take your day off! Don't worry about it. You don't need it. You shouldn't come to me for approval for something like that. Like I trust that if you need time off, you'll take time off. And that's the end of it. Even if we have something important going on, I'm going to assume that you really needed that day more than you needed to come in the office.

And I think where the trust really excels is when there's even a lack of accountability. When they know I'm not going to come up and go, "why did you take that day off? Or why did you go travel? Why did you go to that conference? Why did you buy that book? That book was on math?"

Maybe they're trying something new. I don't know. I don't know? But it's that trust to go? Hey, he's trusting me with all these things, right. And they don't want to violate that trust.

Jerry Li: That's a huge leverage. That by placing trust in other people, it just triggers a lot of really good behavior that you otherwise you possibly wouldn't be able to get. But that takes a risk of trusting people because people may abuse the trust you give them. Or they may have bad behaviors. But without trying it now you lose the opportunity for someone to really , doing the right thing. And, so there's a cost of every time you try to verify something saying, or like micromanage there's implicit costs and that's not a visible to you most of the time.

Darian Shimy: Yeah. I mean, for me, what I want to optimize on is what we deliver to our customers. Right. That that's, that that for me is why we're here. You know what we're trying to do. All these other little things around it are distractions. As much as I can, like push those away and just focus on delivery, that's where I think we're going to succeed in the long run.

And again, you're right. Like that, that trust is, when they, when you start trusting people with those fringe things and then start trusting them on the designs and the implementations and the code reviews, it goes a long way. It changes the mentality where they start thinking, as you would think. And they start thinking more from a strategic standpoint, making sure that they're making the best decision.

And I've had people where we've told them. I said, "this is how we want this feature to work"

and they've come back and said, "this isn't going to work. And this is why..."

and that's what I want. I want the pushback. , I want the friction in the process so we can come up with the best result for our customers.

It does no good... I remember I, this is a long time we had one engineer who I will say she did an outstanding job on the implementation. Tons of unit tests. Basically flew through QA, no problems at all. Customers hated it. And he came up to me and said, "Hey, I did a really good job on that project."

I said, "no, I don't think so. So customers didn't like it. So you don't get any points for like writing good code that is not ever going to be used."

I said, "I appreciate the effort there, but what we needed from you was some pushback saying, Hey, as I'm going through this, this doesn't make sense. This is going to be too confusing.' and put some pressure on them to make sure that, Hey, even when you're told something like this is the design is how it needs to go. It's not enough just to implement it blindly. Right? We need everybody thinking. We need everybody trying to figure out a way to make things better."

I remember that that time, that resonated really well with the engineer, of what his role should be. Because he had, he had a vision of his role was just to go ahead and do what he was told. And this is what really helped him open up and realize that it, his job was much more than he ever thought it would be.

Jerry Li: And that relates back to the thing you mentioned earlier, that you encourage people to think you're the owner of the company. And by taking that perspective, you can see things in the same lens as the owner of the company, like the CEO of a company, the founder of company that gives you infinitely amount of power to, to do the right thing. And, I think that's a really important perspective to have.

Darian Shimy: Absolutely.

Improve your communication by adjusting your communication style and asking more engaging questions

Jerry Li: And going back to the communication, challenge, you mentioned earlier... When you're communicating with either one person, especially a larger group of people and being able to find out how they received the message is really important. And also make adjustment in real time.

I remember in earlier conversations we had in the past, you have, quite a few examples of how you were able to apply that and drive the impact. And can you share some tips and examples should people can, can learn from that?

Darian Shimy: Yeah, absolutely. so. When you talk to someone, right?

It is super important to be able to read them, to be able to understand basically how they're feeling my goal. Whenever I, if I have a one on one with anyone or I'm talking to anybody in any capacity, my goal is to make them feel comfortable. That is my number one goal. If they're comfortable, we can have a conversation. If they have fear, anxiety or anything else, it's not going to work.

So when I first meet with somebody, you know, It's you know, understanding where their level is. So some people are gonna come in with high energy. There... or they may come in with pride. "Hey, I just did something let me share!"

You know, you look a little, little kid come up and look what I drew.

Right. Like "great job!" Right?

So when people come in with high energy, my goal is to exceed their energy level. Someone comes in... you wouldn't believe what just happened. Like tell me, tell me what it was it right. Let me help build it up even more.

If somebody comes in depressed. Angry. Anxiety. Fear. You'll see it they'll come in. They'll be quiet. Okay... I got some really bad news. You're like, gosh... What was it?

And I'm being genuine. Right. But you like, you need to, in those cases, you need to drop below them. Right. You need to help them open up. You need to make them feel comfortable where they can share with you. They have a safe place to share their experience with you.

And even during a talk, especially if we have to give some, some hard feedback, sometimes... you need to be able to read the person. And there's a little thing... like the little, little tricks that come up, right?

Like when they come in, are they making eye contact with you or not? If they don't want to be there, they'll tend to look down, look away.

it's a little like looking at blink rate. People who tend to blink fast... And this is a great thing - watch politicians talk. So ones that are very comfortable, their eyes are open the whole time and people joke, "they don't blink at all!"

People who are terrified, they're blinking like crazy. I look for people when they start fidgeting in their chair. If they start sweating, you know, sometimes, you know, I periodically I'd want to have a one on one with, you know, someone who doesn't report to me, right. Someone who's like, if you. There's a few managers in between me. Sometimes. I think they think I'm going to fire them. And I'm like, I'm like," I just wanted to chat!" And I'll tell them, like, I can see the life draining out of them as we're walking into the conference room... and I'm like, "it's nothing bad. Like I just want to say hi!"

And then we come in the room. They're like, It's just stonewalled... and is, it's kind of making them comfortable opening up. I like to share a lot of my personal experiences, things I do outside of the office with people. And a lot of people think I'm just being chatty and wasting time, but I'm trying to help them open up. I'm trying to open my kimono a little bit and say, this is what I did. These are the mistakes I've made. Let me share some struggles I'm having, you know? And then that hopefully that will let them open up a little bit. Especially with... and a lot of engineers are introverted. They don't like sharing, you know?

And I think , from a, from a question standpoint and a lot of parents may understand this is that... when you're sitting down at dinner, your kids come in, they sit down from a long day at school. There's one question you never asked. It's like, you never say, how was your day? Because the answer is always going to be. Fine.

And then where do you go from there?!

So you ask a more engaging question: hat was the best part of your day to day? What did you learn that you didn't think you were going to learn? Who'd you eat lunch with, you know, what's going on with so and so? Right. Were all your teachers here today ? These are the questions that provoke thought. Usually the questions that will evoke an answer from people.

If you don't want to have a conversation, cause something that you go is everything. How's everything going? That's okay, great. I'll see you later... You provided no value. That was a polite way to exit.

Asking either an IC or a manager like "who's performing really well on your team right now. Who surprised you in the past two weeks?"

These are hard questions for anyone to answer. It requires some thought, cause they're not prepared, right? They may not know the answer. Who's struggling that you wouldn't have expected to struggle. what keeps you up at night? These are all things that can have like two hour discussions with, with just that one question. And this is how you start pulling information out of people.

I think from a manager standpoint, your goal is to get people to open up. As you get people to share, share their experiences. And some people it's tough and they'll, they'll avoid it at all costs. And you have to keep trying to find the angle and you have to learn that every single person is different and that when you find a solution that works for one person, it may not work on somebody else and you need to change gears and you need needed change your behavior, your tone, your body language, to make them feel comfortable so they can open up eventually.

How to reduce fear and increase team input in large meetings

Jerry Li: You talk a lot about, about the one on one, scenario. What do you do at a group meeting? So you have a group of people that you want to have a effective communication. You want them to provide inputs and probably, even make decisions. But as a leader, a lot of people just feel so natural to come in and share, like, "this is what I think... This is what we should do."

And they can tend to talk a lot. So, what's your take on that?

Darian Shimy: So I've had meetings where I've asked people above me not to come. And I've told them. I said, "if you're in this meeting, my team is not going to talk..."

This happens a lot with retrospectives... If the CEO's in the room during a retrospective, you're not going to get any feedback. People aren't going to open up. They're not going to be critical. You're not going to get the raw meat that you want. And there is even times where I tell 'em, I ask people, "should I be in this meeting?"

And my leads know. when I ask that question, I want to make sure if I'm present, I'm not changing the flow. So just even being there... ignoring what the manager will say. My lips can be sealed in a meeting. The fact that I'm physically present will change the discussion that has taken place. That's problem. Number one, problem.

Number two is if you express your opinion too early, you're going to get a lot of, "Oh yeah. Yeah. I agree with that. I agree with that..." or are you going to help shape their minds. So it's super important that early on that you hear from everybody.

And it's, you know, I would say. When you're in a meeting, even if you're not the one leading it, it's your responsibility to be a good host, right. And a good host is one where everybody knows their place. Everybody feels comfortable and you need to make sure that everyone has an opportunity to speak.

You're always going to, if you have a, let's say a room of like 15 or 20 people, you're going to have, you know, a small minority, they're going to do a lot of the talking and you're going to have a small minority that won't say anything. And it's your job to make sure that everybody has a voice and To call on people.

You know, look, if someone is there and shakes her head, it doesn't say anything. Hey, you know, what were you thinking? Like, I don't know if you're, I don't know if you're on board with us, like it's okay. Like, help me understand what I'm missing? Tell me where I'm not seeing how this is going to work. And that's when they start opening up. Right.

And it's the question of, if you went to them and said, do you agree with this? Yes, I do. Okay. That's a safe answer, right?

I think when you're having a meeting, When people speak, they're putting something at risk. And the risk could be, you know, somebody is shooting down their idea. It could be the risk of making a mistake could be a risk of embarrassment.

The best people are in meetings who have no fear, they don't care. In some sense, not caring is a great asset, right? Cause you can leave it all out. I don't care what people are going to think. I'm going to speak my mind... respectfully... but I'm going to speak my mind. And I want them to hear what I have to say. And I could be wrong and I'll learn from that and be better the next time."

So. When you're in there, the first thing is decide whether you should go or not. The second thing is definitely don't offer your opinion too early in the conversation. The third thing is, make sure everybody has a chance to speak before you start, because the best thing for a manager is to go in a meeting. Sit back and listen and have them make a decision that you would have made or that one that you agree with. That's like the perfect scenario you don't have. You didn't have to do any work. You basically went there, you listened. And they came out with the same outcome without your input. That should be the goal.

It shouldn't be you going in and go, "Hey, this is the direction we're going to go..."

Now, there are some times when you need to frame it with a strategic. So you may go in and say, "Hey guys, we need to focus on quality. What ideas do you have?"

Right? You're setting the stage. You're setting some boundaries, but it's up to them to figure out what it is. And no manager ever goes into a meeting like that. Without ideas. I guarantee you. They've thought about it either. If they're walking, taking a shower before they go to sleep, they'd have all these ideas already. But if they go out and say, "We're gonna take care of quality by doing one, two, three, and four..."

well, okay... now they're not thinking about it now. They're going to just, they don't own the outcome. Now, now it's me. So these four things I suggested don't achieve the goal. I own that. It's my failure . Whereas if I said our goal is quality, the team says, I only care about you figuring out how to improve quality and here's the metrics we're going to use. I don't even like coming up with metrics! Let them come up with the metrics.

You know, the first thing on something like that would be "tell me where we are today."

Let them go off. And when they come back, you look at it and say, "Hey, did you think of this? Did you think of that?"

Again it's one of those things to make sure that they've thought about everything, not necessarily where you're trying to micromanage, right. You're trying to kind of help there, help them explore the space a little bit more, but then it's up to them to execute and it's up to them to com... Like, so they've said they've agreed on what the metric is. They've agreed on what the tactics are and they've done the execution. They own the ownership. No other way around it.

And then they can come back and say, "Hey, we've exceeded our goal, or we fall, we fell short, but this is what we learned. This is what we're going to do to make up for it." And a manager in that whole scenario, I did very little. Right.? I'm there at every stage to make sure things are going well, and I can help course correct along the way.

Someone may say, "Hey, we need to get this software."

And I'm like, "well, that's a hundred thousand dollars a year. I'm like, it's not in our budget and this is why we can't do it."

Right. And that's where I'm going to kind of again, put the boundaries in, but then they own everything else.

Jerry Li: A lot of what you've said so far is the realization that being a manager, actually, you can have very easy life by doing the right thing. Otherwise you can take on a lot and make yourself miserable and the team miserable too.

How to "read the room" - The cues and signals you need to pay attention to

One last question about communication. So when you're in a group setting for communication, like a meeting, H ow do you collect information about like body language or facial expressions how do you read the room?

Darian Shimy: So I remember, I took play production, like in high school or something, and I was doing a play. And I remember I was so nervous when I went up there. I was terrified. Like I did not like public speaking at all. And I remember when I got up there and I looked out and into the entire stage. And this is well before cell phones or anything else like that. We used to pass notes on paper...

And I looked down the stage and there wasn't a single person looking at me. And I'm like, "wow, they don't really care? I have nothing to lose!"

And ever since then, I've been very comfortable speaking in a large group.

so going in, I like to have some confidence in what I'm saying to make sure the message resonates, right. Number one. So I've previewed it with a few people. So I kind of know talking points and things and I could kind of pair it myself over and over again.

But you know, it is super important. It's one of those things where... when I'm delivering a message in a large setting, right? Looking in the eyes of people, not talking over them, but talking to them.. . Helping explain to them...

Seeing this is why... lately with a lot of the Slack communication when the cameras are off, its really hard to see , if they're listening and , if it's resonating with them and you know, you look for little things, like I just said something, I got a head nod. Right. Makes me feel good. These are like the unconscious cues and I'm going a smile goes a long way, right? A head nod. you know, these are all like little things in a group that you can kind of pick up and start building on. So, you know, when I started giving a message. If I am not getting the feedback I want and I start changing a little.

And then it's, I think the best way to explain it is when you, as a kid, you have to blindfold yourself, you have to go find something, you start walking and they're like hot, hot, warm, cold, cold, cold. And they're trying to direct you through like using some words. And it's the same thing I'm trying to get from point a to point B in a conversation.

And I'm trying to see what is resonating. And when I start getting that positive feedback, I will start. You know, going deeper on that and spending more time on that when, I'm getting questions, it's a great feedback tool. And a lot of times, if I can't read the room, I will ask I'm like, this is making sense.

Anybody have any questions? Let me see if I can start getting some conversation going. You know, I always tell people like, this is a conversation we're having. I need you to contribute as well. It's not just me up here cooking. Right. And getting that feedback is one of the things that, you know, a, when you get a question, you understand what points were missed, you understand what they want to hear.

And you also know that they were paying attention. Everybody has questions. And I put the fear in people saying, we're going to start saying, I'm saying. And are there any questions I said, if you don't have any questions, I'll ask you some questions. And I typically start in the back of the room, people in the back of the room or in the back of the room for a reason, they don't want to be called on never calling the person right in front.

They have it too easy. So, you know, those are a lot of those, the little clues that we have, coming up.

What leader has most inspired and impacted Darian?

Jerry Li: Great. Closing question. What are the leaders that inspired you in the past? That have made a huge impact on you?

Darian Shimy: So when I was at an E-harmony was founded, by a clinical psychologist named Neil Clark Warren. And you know, when I started at eharmony we were 20 plus people and, you know, everybody kind of knew everybody.

And when Neil talked to you, he had this ability to make you feel like you are THE most important person in the world. There is nothing else that could... you could be at a huge party, and when he came up and talked to you, when he shook your hand, when he looked in your eyes... When he asked you, "how's the family doing?"

It just made your heart feel warm. I've never met anybody to make me feel so comfortable. So good about myself when I was talking to somebody than him. And anytime I talk to somebody, I try and be like him. I'm like, "I want people to feel that way when they talk to me. I want people to feel that comfortable, that open."

I felt I could have told him anything. I mean, he's a clinical psychologist. That's his job. I get it... But still it wasn't in a professional setting. It could have been at a social hour and I'm like... how does he do this? And it wasn't just me. That felt that way. My wife felt that WAY, everybody that talked to him, like he's the greatest conversation I had in my life!

And he just left feeling so good. It's like a Mr. Rogers just feel good. I felt good about me. I felt good about the world. I feel good about my work. I feel good about everything. I felt, no matter how bad something was in my life. If I talked to him, I feel great.

To this day, I don't know what magic he had that made it happen, but it's something I feel I've been chasing ever since. And it's one of those things that I'm grateful and it may sound silly. I'm grateful. I was able to experience what that was like. And I know if anybody experienced it, they would want to be like that. To be able to make someone feel like that. Complete strangers. It was amazing.

Jerry Li: Wow. Let us know when you do find out the magic! We can do entirely episode for that, for that.

I mean, super important. and then it also, indicates that as a leader, every interaction you have with people... how small that is, is an opportunity to make a real impact, like the, just how he approaches in any conversation with the team and with any stranger that's, that's really inspiring.

The Simple Power of "Smiling"

Darian Shimy: Yeah, they're there, there, I mean, I will leave you with one story.

So there was, so I had somebody a couple of years ago come up to me and said, you know, there, they were doing... this gets back to reading the room a little bit... they come up to me and say, "Hey, you know, I'm doing these phone screens for engineers during the interview process. I'm having a really hard time connecting. I can't see them. They're temps, they're nervous. We only have 45 minutes. I have to get through all this stuff. We just, we just aren't getting off on the right foot."

I said, "Hmm. Try this". I said, "when you get on the phone with them and you say hello", I said, SMILE."

That was all I said. say hi, it comes out different. It's a different feel. I'm like give it a shot.

And a lot of times people would come up to me, ask me a question and I never really hear the feedback afterwards... he actually came up to me six months later, he said "that was the greatest piece of advice I ever heard. He goes, every single call I have right now is getting off on the right foot. We're much more open. And I think it makes the person who's doing the high smiling feel better as well. And it's just setting the tone for how this conversation is going to go. It's going to be upbeat. It's going to be positive. They don't have to be nervous. They don't have to be scared. Right. A smile goes a long way.

Jerry Li: Yep. And that's also an example that how you change the behavior and you change how people think. Yourself and other people. So starting with the behavior, that's a, perspective that can help us a lot too.

Darian Shimy: Absolutely.

Jerry Li: Well, thanks so much for spending time with us. I like the stories you shared. It's really inspiring and insightful and actionable. People can relate and be able to apply back to their, their own teams.

Darian Shimy: Well, thank you for inviting me. It's been a lot of fun and, it's been a joy as well.

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