🚀 Breathe.



"As a general rule of thumb, if you want to empower your team to solve their problems, you want to delegate problems back to them. If you can do that over a period of time, then you can start to empower your team and allow them to build the skills they need."

In this episode

In episode #65, Dave Bailey explains how managers can use questions as a powerful tool.

Dave has co-founded multiple VC-backed tech businesses, including Ezlearn, Delivery Hero, and Spotnight. Now, as a Founder Coach, his goal is to provide other entrepreneurs with the practical skills that he wished he had. 

Dave tells us why staying curious a little bit longer can always get you to the root of the real issue… and why most problems aren’t what they initially seem! 

We also talk about goal-setting, OKRs, and how leaders can work backward with initiative.

Tune in for a conversation to learn how to get to the root of issues and set goals that inspire bold action.

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️ review and share the podcast with your colleagues.


Coaching versus Consulting


Agility as a turning point for teams


Delegating tasks, Delegating problems


Stay curious for longer


Self-improvement lies in self-awareness


The 6 meetings of a CEO



Aydin Mirzaee (Fellow.app)  00:00

 Dave, welcome to the show. 

Dave Bailey  02:10

Aydin, Thanks so much for having me. 

Aydin Mirzaee (Fellow.app)  02:12

So Dave, really glad to have you on the show. You’ve had an extensive career as a leader and a coach to tech CEOs. And you’re a sponsored medium author, you write about management, communication, psychology, the works, I have to ask you, how did medium get a hold of you? And how did you end up becoming a sponsored author there? 

Dave Bailey  02:34

You know, what I, after I bought, so I started my career as a venture-backed founder to three companies wide variety of assets. And then I found myself working in VC in London. And as I was working with the portfolio founders, I wanted a channel to kind of consolidate my ideas as I was looking over multiple companies, and I turned to medium to start blogging those ideas. And that’s how it started, I think the cache, you know, you get a little bit of a cache when you got an investor, investor title that helped me get my first few readers. But interestingly, one of the learnings that happened to me very quickly as I got into VC was that, you know, going into companies with a sort of consultant mindset with a kind of I’m here to help mindset doesn’t always work out. So one of the first lessons I learned was, it’s better to take a coaching approach than a consulting, consulting approach. I wrote an essay called why founders need coaches, not consultants. That essay ended up becoming the number one search result for the term founder coach globally for about three years. And that’s how I got into coaching because that generates a lot of CEOs who saw my background and were looking for a coach. And at the same time, got me a lot of, I guess, a lot of new readers, and then medium picks me up, too. You know, and gave me some incentives to keep writing which I gladly took, because you know, what, writing for me is, is a need. Not a strategy like I need, I find. You’ve caught me in writing weeks over the last three days. I’ve been locked away at my mom’s house where I can get some peace in order to crystallize my ideas, but that’s how I got into writing and how medium found me.

Aydin Mirzaee (Fellow.app)  04:16

Yeah, that’s amazing. So I have to ask, what is the difference between consulting and coaching? 

Dave Bailey  04:22

 I heard a great definition just the other day, which was that consultants give you great answers to your questions. And coaches give you great questions to your answers. And I like that because, for me, the art of coaching is really about understanding how questions work, which correct questions, provide the right space, for clients to think things through. And they’re a very empowering tool right in the kind of managers toolkit, and I know we’re gonna talk a lot about management later. Questions are a really powerful tools just because they help. They help provide that space that we all need. Sometimes think things through and find our answers.

Aydin Mirzaee (Fellow.app)  05:00

Yeah, I like that definition. I haven’t heard that before. So coaches provide questions to the answers that you already have within you. I like that. 

Dave Bailey  05:10

That’s right. Yeah. You know, the coaching toolkit is very broad, right? So it’s, this is very much a simplification. Coaches also provide feedback, they can, you know, one thing I learned very quickly is that often, you turn to a coach, not just for questions, but sometimes you need someone to tell you what they see and even give you some advice, too. So a very kind of broad view of coaching. But I think that definition does capture the essence where questions are at the core of what coaching is about.

Aydin Mirzaee (Fellow.app)  05:40

Yeah, I think that makes a lot of sense. So you were the founder of three venture-backed companies, I have to ask you, because you have managed a lot of teams, were you always good at it? Or did you make some mistakes early on?

Dave Bailey  05:55

Did I make some mistakes? The answer, of course, is yes. I don’t know if anyone could ever give a different answer. You know. I, so I, you know, my first job, I was a management consultant. So I got into entrepreneurship back in 2007. But before that, I was working in consulting, and in consulting, there’s a very specific management style, it tends to be very deadline-driven because you’ve got a client give you the deadline, you make move, well, you know, you move well, it’s not to meet the deadline, it has to be top-down. So you got partners in the project, they kind of define the high level, the analysis, the structure of the deck that you do. And the outputs are pretty known. Right? Like in consulting it’s a PowerPoint deck. It’s an Excel maybe a few analyses and interviews all the way. And so when I got into Intertek, you know, when I started managing teams, that my first thing that I managed was a product team, I took those same philosophies I learned in consulting into Intertek and you know, what? Didn’t work, right? Because tech is a very different environment. Firstly, there’s a lot more uncertainty, even when you’re designing interfaces, like anyone who’s designed an interface and felt so confident it was going to work out just fine. Or, you know, planned out how the code was going to go over the next two months. And, you know, you quickly realize that you can’t do that. There’s just so much uncertainty inherent to tech. So deadlines can often break down at least you don’t define them properly. And so yeah, I made a lot of mistakes, I think, in part, because I hadn’t yet learned how to translate the skills I learned in my, in my previous jobs into the tech environment,

Aydin Mirzaee (Fellow.app)  07:32

What was the key difference, so it was more top-down in the consulting world, but in tech, you couldn’t pull it off the same way? 

Dave Bailey  07:39

You know, it didn’t work for me, at least, and it will culminate. So, you know, we were like many studies, and this was back in 2008. First off, so we were kind of a lot of the, you know, the standard things that you learned in entrepreneurship. They just weren’t common knowledge at the time. So we were just making it up as we went along. And so it was a, you know, we our launch was was delayed. Firstly, you know, we had this big launch plan, that’s something that, you know, you get, that gets beaten out of you pretty quick. But everything was delayed, you know, the team was struggling, there’s a lot more early debt that seemed to rear its head. So we were just really, really struggling. And then, but I thought I was on it, right? Like, you know, set the deadlines, you manage, you keep forward-looking. And then one day, my, my best designer, a guy called Danilo who I just respected so much. And he was just performing extremely well came into my office and said, Dave, I’m leaving. And he was like, what really? Do we need you, man? Why are you leaving? And he said, Well, this is another company. We’re based in Rio de Janeiro in Brazil at the time, and he’s like, this is another company, and they’re doing this thing called agile. And I’m, like, agile, we’re super agile. I didn’t know what agile meant, at that point. I said He’s like, No, no, like, they’re doing this thing called Scrum. And I played rugby. And I was like, what the king rugby note. So anyway, I said, Look, stay. And what I’ll do is I commit to getting an agile trainer in to train the whole company, how to do agile, we’re about 30 people at the time. And that’s what we did, we found this amazing, agile trainer by the name of Rodrigo, who came in taught us all agile, and that, for me, was a massive, massive turning point. So actually, one of the reasons why I’m such a big advocate for training, not just because of the skill that it provides, but also that kind of something around like education, that that helps people form bonds gives people a shared language, they can communicate to each other better. And that for me, that was you know, I end up becoming agile, you know, agile certified. That was my introduction to kind of managing in tech environments. And for me, it’s like a fundamental skill if you want to be the manager of a tech team or product team, understanding the concepts of Agile management is very important.

Aydin Mirzaee (Fellow.app)  09:48

So when it comes to delegation then and you know, this whole, you know, moving from consulting and into tech, you write a lot about, you know how to delegate work, so gets done. What is the key to doing that? Because I do find that a lot of managers have especially, you know when you first get into the role it does it is difficult to delegate tasks. How would you say that you’ve coached CEOs and leaders to delegate more effectively?

Dave Bailey  10:19

Yeah. Well, I’m curious, like, what are some of the things that you have found difficult as it relates to delegation?

Aydin Mirzaee (Fellow.app)  10:26

I think the questions that I’ve heard posed to me most often are, how do you? You know, how do you not over micromanage this has been a concept show, for example, you know, basically not getting to the point where you’re not trusting employees fast enough to allow them to do things, or when you see that the work is produced, maybe it’s not to the level that you thought that it could be. This is one the other one is like, How do you know? When you can keep, I guess delegating more work. There’s always this like, this balance of like, what should I delegate versus what should I keep? How, when do you know when too much delegation is too much? These are some of the questions that I think we get asked often.

Dave Bailey  11:26

Yeah, I’ve never met anyone who finds delegation completely easy. Like, there’s just something inherently difficult around delegation, in part because I think, you know, our brains are sort of Pro, you know, what, when you start in, in your first job, you are a doer, right, you learn how to plan, you learn how to, to execute on tasks. And then very quickly, as you scale the ladder, you end up becoming, you know, managing people. And right at the top, you know, when I’m dealing with CEOs, they’re full-time people, managers, you know, when they get to fundraise, that’s one thing they can do, they can also lead strategy development, but they’re out there, they spend a lot of time in one on ones in meetings, managing other leaders, right. And, in some ways, that’s an easier position to be than if you’re on the frontline. Because at that point, you’re often you know, when you get promoted into becoming a manager, you’re also an Icee, as well, you’re also an individual contributor, as well. So you have to manage, work and manage other people, which becomes very, very difficult. So management is very, very challenging. When I wrote the piece around delegating problems, not tasks, it was speaking to the need that, you know, the first step is to really frame what the role, what your role is, as a manager in your head clear, and allow others to solve problems, but you don’t have to be the solver problem. Sometimes you need to solve problems, I get it. But as a general rule, if you want to empower your team to solve their problems, so you want to delegate problems back to them. And rather than sort of telling them what to do, and if you, it, you know, it’s messy, it’s a bit messy, and it’s I’m not saying there’s only one way to do it. But if you can do that over a period of time, then you can start to empower your team and Bill and allow them to build the skills they need. If you don’t do that, then we know what happens, right, they keep coming back for your decisions, you become the bottleneck more and more and more. And, you know, and it’s exhausting, right, like making decisions all the time is exhausting.

Aydin Mirzaee (Fellow.app)  13:32

You know, I had this one time, and it goes back to problems and not tasks, right. I had this, this one person that, you know, was asking me about, I have this employee, and you know, I’m trying to get them to do all this work. And so what I’ve done is I’ve made it as simple as possible, I’ve taken, you know, the thing that we’re trying to do, and I’ve broken it up literally into 25 different steps, like micro-steps, like there’s no way that you can, you can get this, you know, you can get this wrong. And I find that the productivity level is not as I would expect it to be. And this was, I guess, perplexing. But this is like a classical example of, you know, you’re delegating a whole bunch of little tasks. As opposed to, you know, here’s the, you know, the outcome that we want.

Dave Bailey  14:29

Yeah, well, look, let me make it even more nuanced and complex, right? Because as a business scales, roles tend to become more specialized. Right. So in the beginning, when you’re kind of a handful of people, everyone’s wearing multiple hats, everyone, you know, you need to be super-empowered, because they’re not even that much clarity of what your job is. And then as you grow, things get more specialized. Now, there’s some really interesting research into terms of when does empower, management work best, because it doesn’t work all the time. And it Turns out that when you have a task that’s fundamentally process-driven, actually, empowered management is not the right form of management. So if you have someone whose job is just to follow, you know, maybe got a finance administrator who’s going through, making sure the taxes paid, invoices are filed, and so forth, you know, really wide, you know, empowered approach probably isn’t, isn’t necessarily the best, at least not in every situation. And then you have other roles that are fundamentally creative. So, you know, going back to product management, and, and engineering, these are fundamentally creative activities in those in power management is a lot more effective if you’re working with people who seek empowerment and want to solve problems and move forward.

Aydin Mirzaee (Fellow.app)  15:47

Interesting. So in some cases, it does make sense to break it down into a bunch of different tasks and delegate tasks and not problems.

Dave Bailey  15:56

And you know, what it is, I think we all want that one bit of advice that if we just follow it, it’s gonna work every time. And you know, every essay I learn that I’ve written, you know, I’m promoting some idea, some framework, some concept, and it works some of the time, but it doesn’t work all the time. And so the way I think about the growth of a manager is, you know, you’re acquiring these new tactics, these new tactics, these new techniques, frameworks, and your job is to know which framework to use at the given moment in time, but I, you know, I haven’t found that one size fits all just yet, still waiting.

Aydin Mirzaee (Fellow.app)  16:34

So let’s talk about, you know, something more tactical on this front of like, deciding when to delegate and when to take something on. And this isn’t necessarily just like, frontline manager problem, I think it extends to, you know, senior leaders, even the CEO of a company, like when you’re coaching CEOs. And how do you get them to sort of like, differentiate what it is that they can delegate, and when they should, like, really get involved and roll up their sleeves? You know, like, even if you are at the point of delegating a problem, say, for example, you have, you know, basically like a customer renewal problem. And a certain number doesn’t look the way that it should, is that like, how would you like, how do you decide if that’s something that you delegate or something that you want to dig in on yourself? 

Dave Bailey  17:33

Yeah. Well, you know, why I, again, I don’t have a standard approach, it is gonna depend, you know, when we’re working on problems like that, when I’m working on problems like that with clients, you know, what I can do is start to ask questions that will give clarity over what, what is going to be right at that particular point in time. So it’s going to depend on, you know, who you’re delegating to, on your bandwidth. But you know, what, like, one of the big challenges, so I specialize in just working with scale-up CEOs. So I don’t work with any other leaders at this, at this point, just CEOs. And one of the big challenges is, you know, it was characterized as the journey from founder to CEO is going from being that sort of hustler, individual contributor to a people manager. So right around, you know, when you hit around 100 people, that’s the point where you realize the problems in the company, even if you wanted to tackle them, you couldn’t, because either you don’t know how, or you just get too far away from the actual details of the problem. And you have to rely on your leaders. And that’s a really weird experience for someone who I mean, you know, I can speak personally, I, I love doing stuff, you know, like, I get a lot of satisfaction to start a finisher, through and through. So I love that feeling that you get when you solve a problem, or you complete something. And so, the other you know, part of this, of this context of like when to delegate or not, is you also have this bias to probably want to step in and solve the problem. So, you know, we need to take this bias, make it visible, interrogate it, and then figure out what the right thing is for you for the business and your team.

Aydin Mirzaee (Fellow.app)  19:16

So at some point, it does seem like you do get forced into operating in this in this other way of not trying to solve everything yourself. because like you said, once you’re over 100 employees like even if you wanted to, you couldn’t get there. So I think the interesting question is, is it that you get there first and you’re forced into operating that way? Or do you start operating that way and that helps you scale? You get there so that’s, I guess, as a nuance there. One question that I will ask is like and this is something so you know, a person comes up to you, you know, on your team, you’re in a one on one and you know, They come in with a problem for you to address. How do you approach that? What is your advice on approaching that?

Dave Bailey  20:09

Oh, is this species in the context of one on ones?

Aydin Mirzaee (Fellow.app)  20:11

No, it’s not necessarily in this context of one on ones, but it’s more I’m trying to get at the, you know, how do you have restraint and not trying to, like, dive in and solve problems yourself?

Dave Bailey  20:26

Yeah. Well, let me share a couple of things that have helped me a lot with that. Because of course, you’re right, the temptation is someone comes to the problem. Because, you know, you’re a quick mind, I’m pretty sure you you have you have a point of view very, very quickly, right. And it would just be so easy to give it away. So, you know, a piece of advice that, you know, fellow coach passed on, to me, it’s just his name is Michael. And he said, just stay curious a little bit longer. Because when someone comes to you with a problem, particularly a problem that is very well, firstly, let’s distinguish between a couple of different types of problems. There’s, there’s one problem, which is I’m looking for the bathroom? Can you let me know where it is? Now? The answer to that isn’t? Well, what are you trying to achieve? Like, you know, how do you feel about going to the bathroom? What would you do when you get there? Right? No, the answer to that question is the bathrooms just over there. So you know, some informational questions should be met very quickly. Or if this is something they could just Google, you know, you might direct them to Google and say, like, you know, it, etc. So but some of that sometimes coaching can be the right approach. And so I would just advise you, to have the mindset I do this all the time with my clients, that the problem that they come in, they come to you with, isn’t the real problem. So a question you could ask at that point is, you could say, what’s the real challenge here for you? And that’s a question that will force some level of introspection. And you know, they maybe they came about some, you know, the problem with the spreadsheet or something like this was a problem with the code. And they might come in who knows what they get how they’re going to answer that question. Right. But flipping it back to disambiguate what the real problem is because often the problem people come to you with is not the problem. That is the real problem.

Aydin Mirzaee (Fellow.app)  22:11

Yeah, sure. I think that makes a lot of sense. And it’s almost also I know, you said, You came from product management, it also comes from a, you know, sometimes a customer comes to you with a problem. And they suggest a solution. But, you know, you should probably figure out what the problem is, in a bit more detail and stay curious for a bit longer. I love that piece of advice of just stay curious for a little bit longer to make it. Yeah, to get to the root of the issue. And sometimes Yeah, what you first hear is not the problem that you’re looking to solve.

Dave Bailey  22:47

Yeah. Well, you know, if it was, it’d be too easy, wouldn’t it? So, I mean, you know, I got an interesting story. And I was working with a company, this is we’re talking, we’re going back quite a long way now because I was doing some was helping on in a production capacity. And we got the whole leadership team in the car included, and there was a real crisis between sales and between, between product. And what was happening as customers were saying to sales, like one of the key issues we have with this dashboard is that we can’t move the elements around, like we need the ability to move out and around so we can customize it. And the sales team were like, we can’t sell this, we’re you know, we’re going to lose customers. Because of this problem. So I organized the customer interview where the customer agreed to be interviewed in the presence of all of these, all these senior leaders. And so one of the questions I asked, well, if you had the ability, and sure enough, that same problem came up, customers said, we need to be able to move stuff around. So I said, Oh, well, imagine you had that feature right now, what would you do with it? And they said, Well, what we need at the top is a banner, so that we can promote, but you know, the most important thing to the people who are using the system? I said, Oh, great. What else? What else would you do with it? They’re like, No, no, but that’s why we need it. We just need this banner at the top. And there’s this big moment that happened in the product team where they’re like, oh, okay, so they say they want to move stuff around. But what they need is a banner at the top. And that’s much easier to implement than having these movable segments and stuff. The sales Team didn’t get it like see, they need to move stuff around. And so you know, there is this moment when you realize a lot of times will come with a particular strategy to help us meet a particular you know, a particular need. But just a little bit of curiosity, and those few extra questions can help you arrive at something that’s often far easier to help someone with than what they originally wanted.

Aydin Mirzaee (Fellow.app)  24:39

Yeah, I think that’s really good advice. Always stay curious for just a little bit longer. Let’s talk about goal setting. So goal setting, you know, is obviously a core part of leading teams. One of the questions that I wanted to ask you about is, you know, setting ambitious goals. So you set an ambitious goal. And you’re now a few months into that. And it doesn’t look like you’re progressing, you know, towards that goal? It doesn’t look like you’re going to hit it. And you have, you have an opportunity where the team comes to you and says, you know, like, I think we should revise the goal and revise it down. How do you react to that? Yeah. Have you been in a situation where that’s happened? Actually? Yes. Quite recently. Yeah. Well, tell us what happened. So without going into too much detail, yeah, we had this have this ambitious target. On on something we’re working on. And we are not necessarily tracking Well, according to it. And I think like the, you know, the first approach was, the first suggestion from the team was let’s, let’s change the, let’s change the target and make it something more realistic. And my view on it was no, I think like the target is a good target. And I think we can do it, we just haven’t figured out the right approach to get us there. And so the question is, so I think like, what we realized is maybe the approach that we’re taking isn’t going to get us to that target. But maybe we need to revise the approach. Or maybe we need to think about the problem differently. So that’s, that’s basically how we approached this particular situation. But I do think it is it is a fine balance, right? When it comes to OKRs. In general, I know that at least, how these used to be run at Google. It’s about, you know, set ambitious goals and only meet 70% of the target. So I’m just curious, like how you think about, you know, making ultra achievable goals or setting more ambitious targets? And yeah, how do you think about that, in general?

Dave Bailey  27:06

Yeah, well, look, first I relate to I mean, I remember my first company, we had incredibly, we had an amazing spreadsheet that told you exactly how much revenue we’re going to be making in year five, that was back in the time when you needed like a five-year model. And boy, if I, if we to hit those targets, I wouldn’t be here now, I’d be on an island somewhere in the Caribbean. So look, you know, targets. And target targets are tricky. But let me answer this and, you know, maybe take a stab at it from a different angle, which is, I think the root of all performance improvement, lies in self-awareness, and mindset. Okay, so if you think about any performance management system, which is what, which is kind of maybe going to set some goals, review them at the end of the, at the end of the quarter, or the end of the month, and then set some new goals, right. The reason why that system would lead to improving performance oversee not measuring the goals is it provides a moment in time to reflect, to look backward, say, Okay, this is what we thought would happen, this is what happened. And then to look forwards and say, Well, actually, next time, here’s what we’ve learned, here’s what we can do differently. Again, what’s going on is that self-reflection is increasing your self-awareness. And, I mentioned this to a client may rightly push back I said, well, it’s also mindset too, because you can do a lot of people who have the awareness, but they just don’t want to improve, they just don’t want to change. So when you got that magic, magic power, we have the mindset and the self-awareness, that’s when performance can happen. So the target is just a tool. In my point of view, this is I know, getting a bit messy, but it’s just a tool to drive accountability, by which I mean, you know, real review of how things are going, what decisions were made, why they were taking the way they were taken, what can we learn from the past, and to, you know, if we’re, you know, no point learning this stuff, we don’t put it into practice, so to figure out what to do in the next cycle. So if you don’t miss your targets, and when one cycle, what I think needs to happen is a reflection, like the sketching and the cycle reflect, I mean, you push the red button and stop a cycle midway if you want to, but get to the end of a cycle, say we didn’t meet the target, why, what what what was what, what was our role in this? was it? Was it the wrong target? Was it the right target? Could we paint behave differently is this and then really agree on a new target, which can still be ambitious, but it needs to be achievable? Because, you know, in that mindset piece, if people don’t believe they can achieve it, then well, you know, they’re not going to try, right, that’s we need, we need to have some belief that it’s tangible, that it’s achievable. And so that’s, I don’t it’s not, it’s not a direct answer, maybe a bit indirect, but I think, you know, the point of the target is to inspire you to know, bold action and provide the moment in time where you can review and then get better.

Aydin Mirzaee (Fellow.app)  30:02

Yeah, I think that when it comes to a lot of these sorts of things, the timeline is also important, right? So is this a, you know, is this a goal that we are maybe three days away from, and, you know, now we’re not there. And you know, then, or you know, we’re a month away from it, it becomes harder to do things, when you’re very, very close to that, you know, timeline. But if the timeline is a little bit further out like you said, if you have cycles of reflection, and multiple cycles are leading up to, to that end state, then you have the opportunity to reflect and change the course of that, you know, there’s so the opportunity to be able to hit the target. So I think what you said about reflection, is very good. And the goal should probably be reviewed, right? And so that you have the opportunity to reflect course, correct. And then like, strategize, and then hit the target.

Dave Bailey  31:05

Yeah, and, you know, I have a very, what I think is a pretty differentiated way of thinking about objectives and key results as well, which, which may be useful. So one thing that I, I learned, you can’t avoid it when you’re a coach, because what you quickly learn is that the root of pretty much all meaning comes from helping others, right. So, you know, ultimately, we get a lot of meaning in our work from helping others. And so one of the, you know, I guess tips, if you like a framing objective is clarifying who you’re serving, and what you’re helping, how you know, how you’re helping this person. And in a startup, there’s only two people that you’re serving, you’re either serving customers directly, or you’re serving teammates who are serving customers, right? Maybe there’s a third one, which is salts, you know, maybe serving the community or serving other stakeholders, but really, it comes down to, you know, you serving customers here, or you serving teammates, and that level of clarity of objectives can be very, very helpful. Right? So maybe that’s part one. Part two is what happens is memory, I told you, you know, we’re all kind of, from very early on, we’re designed to think in terms of outcomes and tasks and, and initiatives. So what happens typically, with OKRs, you know, probably implemented or coached CEOs implement OKRs, maybe 40 different companies, and it takes multiple iterations. But one of the learnings seems to be, it’s so tempting to try and jam initiatives into the OKRs framework because that’s just how our mind works. Right? For example, as I might use it like, we need to get their website done. Right. So is that an objective? Is that a key result? I’d argue that’s an initiative, right? Maybe the objective, the objective is to help prospects to understand the product and sign up. Maybe it’s something else. But I think it’s a great conversation, what is the objective here, and the key result, maybe a conversion rate or some kind of quantitative or qualitative, maybe you ask, you know, your last 10 customers, what they think of the website afterward, and you want to get a good score, maybe do an NPS or operate the product market, Product Market Fit survey as examples of qualitative metrics, but having clarity over the how you will measure success, that’s the key results, and who you’re serving. That’s the objective, that can tee up a conversation around initiatives, what initiatives do we think are going to help prospects, you know, understand the product and sign up. And it also really helps when you’re making decisions, particularly on that website, it’s gonna get a very detailed understanding of why you were doing that website. That’s the power of what works can offer. But you don’t get that if the website becomes your, your, your Okay. Now, the reason I bring that up is that you said, you know, it depends on the timeline. These objectives are typically around helping people. They typically live in a space where there is kind of no absolute done, there are only degrees of done. And then what you’re looking at is what initiatives are possible and desirable, and valuable in the period. And then you’re managing differently. Right, you’re managing initiatives. And ideally, they’re managing their initiatives, with the flexibility of swapping them out if they aren’t meeting the objective, right? So I would just kind of just volunteer that as A way to think about ours that helps you preserve people’s autonomy to swap out their plans and tasks when they realize they’re not working out.

Aydin Mirzaee (Fellow.app)  34:34

Yeah, so this is very interesting. Like because, you know, no company today doesn’t have a website that should be refreshed every so often. And, you know, how do you know that you’ve done a successful refresh, you know, and like you said, there’s no done there are just different stages of doing. So this is a very important point and, and yeah, how do you basically like turn initiatives into Objectives. So I think as the concept of like tying it to a specific result to a specific number conversion rate, you know, communication bounce rate, you know, something numeric or something measurable in some way, even if it’s a qualitative way, but as long as it’s measurable, it’ll, it’ll form a lot more clarity around what you’re you’re doing so that when you have achieved it, you know, that you are done for, you know, the work that you’re doing. And like you said, that gives you the ability to swap out different initiatives. So that just in case one isn’t working, you can bring in another one that maybe gets you to the same place.

Dave Bailey  35:42

Yeah, absolutely. And, I mean, I’ll tell you a secret, right?  The secret is, when I’m working with clients, we, you know, when you look at someone’s OKRs, you can very quickly see the tasks, right? Either the reader posing as an objective, or the person is a key result. And the way I do it, is I work backward, because if the brain is going to, you know, force, it’s going to think in terms of initiatives, let it and then work back backward, who am I trying to serve with this initiative? And how would I know if the initiative is successful or not? Other than it just being done, right, because I know, we all love DOD, and we want to get to done and working backward, there is something quite magical. So if you do this in your planning period, you know, you’ve got a planning cycle and maybe do some sort of strategy review, and he replans for the next cycle. When you do this, what you find is by clarifying who you’re serving, and what you’re trying to help them to do, you often find new initiatives that achieve the same thing that takes half the time, they let you know, I kind of think of this as like a metrics-driven approach to planning. Because once you identify how you’re going to measure success, all of a sudden, this bout of creativity comes and can be very, can be very cool, like to see that creativity emerge. And to realize, Wow, we didn’t need to do that website. After all, we just needed to do this other thing, which is much quicker, but it’s gonna have the same result.

Aydin Mirzaee (Fellow.app)  37:08

Or maybe all we needed is we needed to put a banner at the top. Or just put a banner at the top. By here. Exactly. I mean, I like that, because it does look back to what we were talking about earlier, right, just this concept of, you know, stay curious for a little bit longer. Even on the initiatives, we need to do this. Okay, why do we need to do this? What is the objective? Are there other ways to do it? So I think that that makes a lot of sense. [AD BREAK BEGINS] Hey, there. Just a quick note, before we move on to the next part, if you’re listening to this podcast, you’re probably already doing one on one meetings. But here’s the thing, we all know that one on one meetings are the most powerful, but at the same time, the most misunderstood concept in practice and management. That’s why we’ve spent over a year compiling the best information, the best expert advice into this beautifully designed 90 Plus page ebook. Now, don’t worry, it’s not a single spaced font, you know, lots of text. There’s a lot of pictures. It’s nice, easily consumable information, we spent so much time building it. And the great news is that it’s completely free. So head on over to fellow dot app slash blog to download the definitive guide on one on ones. It’s there for you. We hope you enjoy it. And let us know what you think. And with that said, let’s go back to the interview.[AD BREAK ENDS] Dave, one thing that we should talk about is meetings. Since the pandemic, people have been meeting more, not less, and the world has really changed. I think it’s a topic that you know, we think a lot about, you’ve written about, you have this methodology that you call designing the Alliance, he has a cool title. What does that mean? It sounds a lot more fun than just having a meeting, designing an alliance. So what is that?

Dave Bailey  39:09

Yeah, okay. So this is, you know when you become a coach, and you take your coach training, this is one of the techniques I teach you early on, which is that when you’re in a coaching relationship, taking a few minutes at the beginning of any session, just to make sure that your people are going to get what they need out of them out of the session is worth it’s worth taking the time. So you can apply the same approach in any meeting really where you’re asking essentially, three questions. One is, what do we need to commit to getting the most out of this meeting? the open question, this group around the table, you know that we need to stay present. Okay, great. We need to put our mobile phones away. We need to listen whatever it might be. Next question is, are we going to give each other permit permission to hold those commitments? Now when you offer permission, nine times out of 10 you get Yes, yes, of course. A third question is: How would you like us to do that? And people are like, Oh, just call me out, just put your hand up, maybe you could inject some humor and, you know, find a different way to, to set that up. But those three questions, what are we going to commit to doing have permission to hold those commandments? And how would we like to, you know, uphold those commitments? they can, they can provide everybody with the tools needed to uphold those commitments, right. So if you see someone in the meeting, and that they’re maybe taking steering away from the agenda, right, maybe we want to commit to the to staying to the agenda and parking things in the parking lot for later, then it gives everyone not just the permission to uphold them, but also how right we’re going to do that by raising our hand, or we’re going to do that by calling it out or reminding people. So that’s really what designing the lanes can do. And it’s particularly useful in meetings that, you know, where you, you can predict it’ll be difficult to manage later on. And you can use that tactically to, you know, to set up the right rules of the game, the ground rules.

Aydin Mirzaee (Fellow.app)  41:08

Yeah, so I guess a lot about a lot of it is the ground rules. But too guess the other thing that you’re doing maybe subtly, is you’re also defining a purpose for everybody getting together. And so if you started by reiterating what the purpose is, I mean, that just the, like, the workflow of defining a purpose, stating the purpose probably just builds a lot more Alliance, every everybody’s on the same page. And in a world where you’re going from, you know, meeting to meeting to meeting, sometimes being reminded of the purpose of, you know, a meeting that you’re having is probably not a bad thing.

Dave Bailey  41:48

Yeah, well, I let me speak to coaching sessions, which are probably most analogous to one on ones in a company, then, because you design the Alliance was very quick set up making sure ground rules are in place, you go into the kind of setting up the agenda. So in a one-on-one, then people run in many different ways. Sometimes people send topics before the one on ones and people will arrive and just get into it. But what will happen is you might ask him, so let’s expand, maybe this is a group session, right? You could ask the question, what would each of you like to get out of this meeting? So that’s a little bit like coming back to purpose, when, of course, people are going to bring different objectives differently, everyone has their purpose, right for the meeting. So clarifying that at the beginning, the beginning can be helpful. But one of the interesting features of particularly one on ones coaching is that people will say, Well, at the end of this session, this is what I want to get out of it. And you might take them at face value, like oh, okay, cool. Well, let’s move towards that. But often just providing, again, is that staying curious, a little bit longer, but just providing a little bit more space? How do we create space, you ask a few more questions that can often allow, help us refine the agenda, and often what people think they want coming into the meeting isn’t actually what they want. And so, so agendas, you know, I’m sort of learned to be a little bit fluid with agendas, because it’s nice to, you know, have a firm starting point. But actually, sometimes what people take from the meeting isn’t even what they came to the meeting for. And so is a being a bit open to that and allowing people to get what they need from the meeting, which they may or may not know, again, I’m talking in the coaching space, right? Not necessarily if this was a sales review or something like this. Yeah, right. Exactly. Yeah. So some meetings. I mean, that’s it. I mean, the other essay that I wrote on meetings is called the five meetings of a CEO. Which actually, I wrote that maybe a couple of years ago, I now I think I want to say the six meetings now.

Aydin Mirzaee (Fellow.app)  43:48

Oh, what’s a six meeting?

Dave Bailey  43:50

Well, okay, so the five meetings are you got the status update? Okay, your status update is for accountability. Right? You got 1:1s for you know, for coaching and empowerment, you’ve got the getting completely out of order. You’ve got the retro right that’s for allowing people to kind of give their feedback and Be Heard you got Friday wins. That’s to block in time to celebrate. Because as we know, right, like, the job is never done. If you don’t block in time to celebrate, you probably won’t. And then what am I missing now? Did I say one on ones? Yes. Yes. Friday wins, status updates, iis one more than a missing? Well, anyway, I’ll tell you the sixth one.

Aydin Mirzaee (Fellow.app)  44:39

The sixth one is. And by the way, like I’m either putting you on the spot and getting you to recite something like this, which is always like a challenge when you’re on this fight. But what’s the sixth one? Because this is the new one.

Dave Bailey  44:52

Now I remember the other one, the other ones? The All hands. 

Aydin Mirzaee (Fellow.app)  44:55

Oh, okay. So that’s different than the Friday Wins.

Dave Bailey  44:58

Yeah. I will tell you I I think you can separate them like it’s a bit depends on what you want from all hands. But all hands for me is a point in time where the CEO can communicate to the entire company and leadership can communicate to the entire company. Maybe even you know, there are different ways to run one or hand, some people have more of a town hall approach. Whereas Friday wins. And again, you can combine these meetings, there’s more about the concepts. By doing this is really about ending the week on a high, looking at what we’ve achieved. And having the mandate to look at the positives, look at what we’ve done, celebrate the wins, and end on high. Now the sixth meeting. So I you know, one of the things that comes up a lot in when I’m working with CEOs is the leadership team meeting, it’s a difficult meeting, for a number of different reasons. And tthere are lots of things written about it already. One of the things I realized is happening in a leadership team meeting is that the agenda is typically pretty packed. And it’s pretty diverse. So on the one hand, you have like a status element of this agenda, like what’s going on, like, tell us what’s happening. But on the other, you have this sort of interior space, maybe in any other business or in topics to discuss, where, in particular, you want to create a space for discussion without necessarily getting to a resolution? And I say that because of course, we want to get to a resolution, but is it? Is it realistic to get to a resolution on each one of the topics at every single meeting? Probably not, what happens is you leave the meeting feeling a little bit like half did, or you know, this kind of open space, right? Anyway, I was researching offset offsites as a matter of fact, and in the research, I realized that two processes happen in a creative problem-solving process. One is a divergent process. This is where ideas are formed, possibilities are explored, through open-ended. And then the other is a convergent process. This is where you make analyses you make decisions. And you know, you plan the path forward. And the big insight is that these two processes do not work well in the same part of the meeting. Right? So if you’ve got someone who’s trying to be like thinking of new ideas, new possibilities, maybe discussing controversial topics, then you got someone else who’s like analyzing them straight away. Now we tried that didn’t work. Well, that just shuts it down. And similarly, if you’re trying to get convergence over something trying to, you know, finalize the plan, someone’s coming up with new ideas, maybe you’re in a stand-up meeting, right, it’s a very convergent meeting. So I was like, oh, Aiden, have you done this? Based on the other? Have you thought about that? And everyone’s listening, and you’re like, ah, let’s get the, let’s get the standard done first, and then we can open this up. Right, so so I now think it’s worth separating ohe kind of convergence side of leadership at status, the updates, and so forth into one meeting and have a separate meeting, which I’m calling forum, Leadership Forum, just to talk about topics where there’s no need necessarily to come out with a very specific outcome. So that’s the sixth meeting.

Aydin Mirzaee (Fellow.app)  48:02

Yeah, I 100% agree, it’s so interesting. So my co-founders, and I have, we meet twice, twice a week, you know, once on a Wednesday, and then once on a day in the weekend switches from Saturday to Sunday, depending on you know, life and other things. But we have specifically we found that we can’t we call like Wednesday whirlwind, what Wednesday because it’s just the all the things that we just need to discuss that are like more operational, what’s going on, it’s much more like the, you know, immediate problem-solving type mode. And then the weekend session is much more about let’s like, take a topic and spend the time and like, really think about and problem solves, and it’s more like a mini ooff-site And so what we found is that, before we used to do these things, you know, whenever they came up, but then there is this clash, right, which is like, oh, like, are we brainstorming too much, this is taking too long, we’ve got this other stuff to get to like you said the list is too long. And so by separating it, it does give us the freedom on the day where we’re like, you know, very purposely doing blue-sky type stuff. It does, it does help them run a lot better. I wish we had started that a long time ago. And this is a more recent discovery.

Dave Bailey  49:28

Oh, and it’s very subtle. I mean, it took me a long time, my finger on what’s going on. Because you know, it’s funny, if you ask, if you ask, you know, any number of CEOs, how what they think about the leadership team meeting and you ask it in private, okay, you ask it in private, most of the time, they’re going to say three to a five out of 10. Like there’s this level of dissatisfaction that happens with the leadership. You know, the first, you know, where your mind goes is, oh, well, maybe there’s like clashes in the leadership. Maybe it’s a people thing. But I started reading to realize it’s partly an agenda thing too. And so You know, just following on from that kind of convergence and divergence, because they don’t work well together, it’s really good to deliberately and distinctly separate them to do the current, you know, the divergent thing, let and then take a break a long break, maybe you want to sleep on it, maybe you want to take a week to think about it, and then come back once the dust is, you know, metaphorically settled, and then look to converge, you know, analyze, plan, decide whatever it might be, but this bit, spitting them out has a lot of aenefits. So glad. Glad to hear you doing it.

Aydin Mirzaee (Fellow.app)  50:34

Yeah. Now, this is super helpful. The six types of meetings like this. Dave, this has been super insightful. I know, we’re getting close to time. We’ve talked about, you know, so many different things. We talked about OKRs, staying curious for longer. You know, we talked about all the different types of meetings. So one question that we like to always end with is for all the managers and leaders looking to constantly get better at their craft of leading teams. What tips, tricks, resources, or parting words of wisdom? Would you leave them with? Obviously, we’re going to link to all of your articles and the many, many, many things that you have written. So that aside, what else? What else? Would you leave them?

Dave Bailey  51:21

Yeah. Okay, well, look. Um, so I was a venture-backed founder for about 10 years, before, you know, getting into investing and into coaching. And when I learned to coach, I was like, I wish I learned this sooner. Because as the deeper you go into every field, whether you’re working sales, whether you work in marketing product like it doesn’t matter. The deeper you go into every field, you realize the power of questions. And I think there’s something that like, everything seems to converge at some level, to the same basic insights. And for me, coaching was a very quick way to get that because coaching is, by its nature, a little bit agnostic. And it kind of helps you jump straight to that sort of know why he’s question asker. Right. And if you want to sell you got to know the right questions to ask you want to build great products, you got to know the right questions to ask if you want to make a meaningful message, land with prospects, you got to know the right questions to ask. So I would say my parting words of advice would be to just learn a few basic coaching techniques. There are some great books out there, I’m a big fan of Michael Hani, a Stanley who wrote the coaching habit and he’s got a new book called taming the coaching monster, I believe. What are the good books out there? And then there’s a bunch of courses too, you know, I’m in the process of building a business that’s designed specifically to help founders and their teams learn and apply coaching skills in their businesses, but I do believe that I you know, it’s kind of the skill that as a leader, as a manager, I wish I’d learned a little bit sooner. So if you are curious about that. And I’ve also written a bunch about different coaching models that you can apply as a manager. Just give it a go, right? It’s definitely experiential, you learn by practicing it, but what I have noticed is, you know, I did, I did Chris Voss’s mastermind on negotiation.

Aydin Mirzaee (Fellow.app)  53:22

Oh, yeah, the masterclass, right?

Dave Bailey  53:27

The masterclass, yeah, It’s amazing, right, applied empathy, and sort of the art of the question, the question asking, you know, when to when to use why we’re not using. So he but you, but honestly, from the lens of a coach, I’m like, Oh, my God, this is, this is what coaches do, like, Oh, you know, and similarly, like, when you take advanced sales training, right, you realize it’s not just about, you know, framing the benefits and so forth. It’s about building relationships by building trust. That’s what coaches do. Right? And then, you know, talked about products, like what would you do if, if you got there right? What would you classic coaching question, right? And when that is identified, the banner is the answer. So there’s a lot of insight that coaching brings to each of the disciplines and it’s not that complicated. So if your crew you’re curious, you know, go and find some resources. And, and, and just try it, see what you get.

Aydin Mirzaee (Fellow.app)  54:20

And a great place to end it. Dave, thanks so much for doing this. 

Dave Bailey  54:23

Oh, Aydin, thanks for having me.

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