Webinar Transcript
Anthony: hello, I’m Anthony, founder at Seed Legals, now launched in New York, uh, previously and still in the uk, uh, but launching in the US so that US founders can find a faster, better way to do their funding rounds. But apart from the legals in our platform, I love finding people that are solving problems that founders have quite apart from the legal problems. And so when I met Craig at an event and saw how he coaches founders on their founder journeys, I said, we’ve gotta get on a webinar together.
Anthony: So here’s the challenge, which is most founders are tech ish. You know, they’re INTJ or INTP. If you know your Myers Brigg profiles, they’re probably introverts. They love sitting and coding and doing emails and, uh, listening to German opera in, in my case. And, but now as you’ve got a growing company, you’ve got a whole lot of different pressures and problem spaces, and you have to reinvent yourself as the leader.
Craig: You have to make sure you’re spending your time on the right things. You have to create a scale up growth culture and so on. And I don’t claim to be an expert at any of these. In fact, I need to allow the couch and listen to Craig talk about all of this. So without further ado, let me hand over to Craig to introduce himself, and then we’ll talk about the topics we’re gonna cover, and, uh, hopefully help everyone here on their founder journey as you scale your business.
Anthony: So, Craig, take it away. Thank you so much, Anthony. And, um, we have to talk about that, uh, German opera at some point as well. Um, I, I just, uh, had the, the pleasure of, uh, attending, uh, lab OEM at the, uh, the Met Opera, uh, over the weekend. Um, hi everyone. I’m, I’m really excited to be here and be part of this conversation. And, um, I, I really see this as a collective learning, um, environment. Um, I’ve been in the coaching space for, uh, around 20 years.
Anthony: Um, this is really my life’s work. Um, I’ve been inside of orgs as head of, uh, head of culture, uh, both in startups and in the corporate setting. Um, and currently I am partner and executive coach with Newberg Go and Associates, which is a firm with all offices in New York City and San Francisco, um, specializing in helping startups and their founding teams, uh, gained the mindsets and the leadership skills in order to scale. Uh, we do that through teaching skill sets, frameworks, mental models and, and and such.
Anthony: Um, and we’ve been doing that for a larger part of 10 years. Um, our, our focus is, um, early stage Series A is a bit of a sweet spot for us, and we’ve coached over 1200 founders, uh, to date. Um, I think we’ve been a part of 52 exits, um, totaling in over 5 billion in in value. Um, personally, uh, my journey, um, just a little background, um, I was in the leadership space as an experiential educator, um, really, uh, task-based, um, leadership development, um, challenging experiences in the outdoors and helping people sort of learn through, uh, those challenging experiences that moved into psychotherapy.
Anthony: From there, um, started working with founders and leaders again, um, actually entrepreneurs and CEOs as, uh, psychotherapy clients. Um, and then got hooked up to Techstars, uh, which is an accelerator program.
Anthony: Uh, you all might, might know of building programs there and began to work with early stage and series series A, uh, specifically, um, startups from the, Okay, thank you. So I like the psychotherapy angle because, you know, founders think it’s all about the product and tech and, you know, SDR outreach and a whole lot of sort of transactional things, but there’s a whole mindset to be had. So, uh, broadly on this, we’re gonna cover, I think, divided roughly into four sections, and then we’re gonna take, uh, you know, questions and so on as we go along.
Anthony: So, thing one is moving from purpose to performance. I’ll get back to that in a second. Secondly is the CEO’s best use of time. Next is the evolution of a leader and the team. And lastly is creating a scaling and growth culture. So let me dive into the first topic and then hand over to you, which is a while back when we started Seed Legals, I noticed when we got about 20 people that our, uh, one of our key initial hires was getting not quite right for the company.
Anthony: They wanted a particular role, but the role had changed. And, uh, then I went to a, an event organized by Index Ventures, and I learned that when you get to 20 or 30 people, you often have the first pain point that founders see with the team, which is that the early team members previously were the only marketing or growth person, but now they’re part of a team.
Anthony: Maybe they don’t have access to the CEO anymore because there’s just not enough time. And the company is now switching from just a mission and a purpose of building something to selling it. And early team members might be focused on the mission, the purpose that the performance, KPIs, OKRs, targets, they see us kind of like almost a negative, right? But you can’t have a business without that.
Craig: And so I learned actually that the problem space that I saw with some of our earlier hires was not unique. In fact, everyone has that problem space. So take us through how, what I see is that first switching of gears from we’re a small team to actually, we’re a scaling business and have to organize accordingly. Over to you, Craig. Yeah, I I think that’s a really great, um, kind of, uh, journey you just took us on yourself.
Craig: And the way that I see about, uh, see this is, um, you know, we’re over, over the course of time, we’re, we’re really moving from, um, sort of that the founder mindset into a leadership mindset. Um, um, in invariably a lot of founders spend a little bit too much time doing the work or decoding the work. Um, those are the sweet spots. Um, they’re either down in there actually taking on what should be as we grow, uh, sort of leadership roles, um, like a, um, you know, it might be product person or something we actually need to hire.
Craig: But, um, as, as founders, we’re actually fulfilling those roles. Um, or they’re way too out in front, you know, continuing with too much of the, uh, visionary work and sort of driving the purpose forward. Um, instead of delegating the work, instead of, um, creating the systems and the processes, um, and or driving performance in the team by way of holding the team accountable by way of, um, you know, uh, sort of level setting in terms of what the priorities are and such, and having those tough conversations and, and really driving collaboration inside of what, uh, what, what, what should be the, the, the executive team.
Craig: Um, and oftentimes there has to be sort of a forming of a, like a, a clarity around layers in the organization, um, in terms of, you know, we move from a flat organization early stage into, uh, some distinctive layers.
Craig: And I think that you mentioned a previous conversation, we might have less access to, you know, CEO and such. Um, boundaries is a big part of that. And so I often say one of the things that we need to be looking at is, um, we have to start limiting, um, unstructured jam sessions. Um, you know, in terms of, uh, who gets access to us as CEOs and or the executive team, That seems like the opposite of the culture that you want to create, which is, hey, come by visit, you know, stop by my desk, visit me.
Craig: And I think also the other thing is how do you recognize that you’re down in the weeds too much? Because the problem is when you started the company, you know, you were the first sales person, you were the first product person, so you actually know more than anyone else, and you’re probably better at most other people’s jobs other than the design team and the coders than than them maybe sometimes them. So how would you transform yourself outta that rather than continuing to do that?
Craig: I mean, it’s a problem, I’m sure my team tell me that I’ve got, and I’ve seen that in many others as well. Yeah, I, I think the, the first, the first bit is understanding that you have a problem and understanding that you are, you are actually spending too much time fulfilling, um, either a role that doesn’t exist or somebody else’s roles. And so feedback is a big part of that. Um, having a transparent culture inside of part, in particular your leadership team to, uh, sort of glean that feedback is, is often that’s a blind spot.
Craig: And so we, we really have to, um, we really have to encourage and create a, encourage our, our, um, our, our teams and create a, a culture of transparency for others to, to hopefully be giving that feedback. But I think from a self-awareness perspective, we can be looking at how and where are we spending our time. I think you mentioned earlier, best use of time. Um, we should be a startup founders, for example, focusing on things like strategy, focusing on things like hiring, focusing on things like, like fundraising, um, uh, you know, customer face time and, and such.
Craig: We’re spending too much time, you know, in the engineering space, um, which that might be our background. Um, and again, doing the work, those are all red flags to me. And so it’s one of my first questions to a founder, um, or, you know, just a, a, a founding, uh, exec is tell me what you’re spending your time on, because there’s definitely good use of executive time and bad use of executive time.
Craig: Okay. So for, uh, you know, if the numbers are different for let’s say a 50 and a one 50 person company, what would you think is the, if I were to look at my calendar or a founder were to look at their calendar for the week, what should be the split of time that they spent on different things? And then we’ll talk about what to do if there’s a serious imbalance. Yeah, I, I think, so we, we discussed one-to-ones.
Craig: Um, and this is a, this is a, a sort of a hot topic right now in inside of startups. I think, um, spending time in the right meetings with your, um, with, with your team is, is a good, is a good use of time. Um, are you having one-to-ones that are directive, um, that are spent prioritizing, uh, against the tasks, um, are set, um, you, you know, in terms of running accountability, um, I think that’s, that’s a good use of time.
Craig: Um, are you creating blocks for strategic thinking or deep thinking? Um, and absolutely know what your priorities are for that week in terms of what you are driving and what problems you’re solving, um, versus, um, your, your calendar is filled with, um, meetings that have been booked for you in terms of, um, you know, other people’s needs. Um, that’s always a flag for me.
Craig: Okay. So let’s talk about one-to-ones. I always thought that one-to-ones was super important. You know, particularly if people working remotely, because Slack conversations and email conversations quickly spiral out of control, whereas just talking to someone, you get in sync. And if you’re waiting on someone, it may turn out that your, all your outbound comes with somebody, you’re like, gimme this, gimme this. But, and actually when you talk to them, it’s different. So there has been a bit of a thread on the internet. I think some person said one-to-ones are a waste of time. I’ve canceled them all.
Craig: I think that policy’s a complete disaster because things will, it’s much better to talk to somebody than to not talk to somebody. Um, one issue is there’s this concept of maker time versus manager time. So if you’re a software developer or a lawyer or something, what you want is you want no disturbances in the day. So you can get on with some complicated thing that you’re doing, but just one meeting in the afternoon can have your entire day messed up while you prep for that.
Craig: And you’re not gonna start this, ’cause this one’s in an hour. I know the feeling myself, I’ve got an important presentation to do that, I’ve only got a little time, I’ll do it tomorrow. And then it never arrives. So there’s make a time where you want a lot of free space and there’s manager time where it’s like, dude, I’ve got eight hours in the day, half an hour, but thing that’s 16 meetings. You want a meeting, stick it in, find a slot, we are good. And I’ll context switch. So the argument with one-to-ones is that by putting time in someone’s di it can mess up their whole day.
Craig: Yeah. Let’s talk about quickly the one-to-ones, and then let’s talk about how to get the most value from those one-to-ones as opposed to nice weather we having. Yeah. And how are things going with you? Yeah, yeah. I, I think, so one-to-ones get a bad rap. Um, I think because they’re not, they’re not concise and they’re not structured and or they’re, they’re their, their sort of one offs. What I’m not talking about when I talk about one-to-ones is, is people just grabbing time on your, your calendar.
Craig: Um, I think if somebody’s grabbing time on your calendar, there should be a specific, uh, agenda item that’s very tactical. Um, or, or has, you know, some, some, some outcome associated with that. When I’m talking about one-to-ones, I’m talking about one-to-ones that are generally, if you have a team are structured at the beginning of the week and they’re about, um, aligning on priorities, they’re about, um, problem solving. They’re about, um, sort of flagging issues and or doing a little bit of solving and really position it for the rest of the week.
Craig: Um, and the manager or the CEO or whoever it is who’s in the leadership position, owns that meeting and drives that meeting, um, and comes with specific questions. And whoever’s coming to that meeting is expected to come with questions as, as well. And so I think really poor, um, meetings, um, are a result of the leader not setting expectations and being clear on what they expect. I expect you to come with questions. I expect you to come, you know, with issues that you’re flagging and such.
Craig: Um, and so I think having those well structured, uh, throughout the, um, the, the, the week is really important. In addition, um, you know, I think that to your maker mode bit, I think it’s extremely important for people to block, you know, space on calendar for that maker time for that creative time and, and protect that and understand where they need that. For example, for me, um, Wednesday mornings, I need that time.
Craig: Um, that’s my creative time. Um, I know when I’m most productive and such. And so I don’t take any meetings. I certainly don’t do any one-to-ones during that timeframe. So knowing when you’re most productive, um, and playing ahead of your, your development time is super key For me. I think that’s called the weekend, but maybe that’s the problem I need to talk about. Okay, sure. So, so let’s now focus on, as the founder, you want to extricate yourself from many things.
Craig: How do you motivate your team and put them on point? Because the reason the, the problem space arose, ’cause you were doing these quite effectively yourself, it was often more efficient for you to just do something yourself, then to pass it on to others. How do you, what would your counseling be for creating that structure? Is there a senior leadership team? You know, how are people on point? And, and also let’s talk about which people you can see that you want to promote. ’cause they naturally want to own things as opposed to people who are brilliant at doing things that don’t like to be given, you know, ownership.
Craig: Like, I, I just wanted to code. Please. Yeah. Yes. So the first, so I, I think it’s important to, and I, I’m working with a couple sort of seed stage orgs right now. And they’re at the beginning stages of podium, what, what I call their first team together. Um, we might not have all executive hires in a row and such, but there needs to be the formation of a core group of decision makers, um, a core group of folks who are sort of, um, uh, creating a cohesive sort of direction for the company that’s not just the founder or even the founders, um, and represents the, um, you know, sort of the, the, the most important functions in the business, whether that’s engineering, whether that’s, you know, finance people, et cetera.
Craig: Um, from, from there, I think that that notion of first team is important, whereas there’s those functions, but we have to be focusing on the, that team being the most important team and driving the business forward.
Craig: Um, and so first team principles is, is sort of this notion of the first team is, uh, is unlike the United Nations, where the United Nations, each nation has its own sort of agenda that’s driving how they’re showing up. Um, we’re actually thinking, uh, cohesively about the whole, uh, versus the sum of the parts.
Craig: And is that the senior leadership team, as it’s often called, that gets created to hunters a pack together? Yes. Yes, exactly. And with that said, um, you know, as we’re scaling, I think thinking about how we work, who, who we are, and who we need to be as a team, and really beginning to, and this is kind of the formation of culture, whereas culture is just sort of in, in the blood, um, likely of the founding team. We don’t need to literally talk about it, but I think as we scale, we need to begin to define who are we, who do we need to be, how do we get there?
Craig: Um, and what are our ways of working? How are decisions made? Um, how do we give each other feedback and such and really begin to create, um, a, a v one of a team charter, which is basically a set of agreements in which we sort of operate under. Okay. And so that senior leadership team is really important because each team, you know, if they are good, they’ll all go and like a hunter killer submarine, they’ll go achieve their goals themselves, but sometimes they’ll misalign, right?
Craig: The sales team will just want to sell stuff, but it might be the wrong stuff. Or maybe they’re waiting on the tech team, but the tech team is optimizing on something else and not helping the sales team with the things they need. So the sales team go off and use some third party, and now it’s all a mess. That’s right. But getting them together can set those common goals. So at what point in the company’s growth do, is it worthwhile creating that, uh, that kind of structure?
Craig: Yeah. Um, the, the point that I see it being most effective is usually at about the 20 to 30 ish, uh Okay. Sort of, sort of mark. Um, I, I, I think that’s where there’s generally enough complexity, um, where we, we all can’t fit around one table, you know, for example. Um, and there’s enough, enough, um, distinction in the functions. Um, comms are beginning to fall down, priorities are beginning to get muddled. Um, and there’s a, there’s a sort of a competed competing, um, uh, sort of a lane for or, or need for as much distinction as there is, um, continuity, right?
Craig: A distinction of, you know, finance and, and engineering. But it’s really about continuing to do that and drive those areas of expertise and such, and those functions while focusing on the relationships in between the functions, right? And that’s, that’s what, that’s what a first team does really well, by the way, is it, it creates excellence and it instead, you know, sort of function, but then also equally focuses on the parts in between the relationship between marketing and sales and such.
Craig: And that’s where really good CEOs are driving incredibly effective team meetings, and they’re consistent. I’m, I’m a, I’m a big, big, uh, fan of, of team meetings that are consistent and they focus on priorities, they focus on feedback, and they focus on alignment, feedback being really, really important.
Craig: A lot of studies, um, show that, uh, peer-to-peer feedback, um, uh, especially is, is what drives more performance than a CEO feedback, for example. And so creating a culture for sales, drop the sales, drop the ball, CEO can get feedback, that’s great. But if marketing has given feedback to sales, I mean, much more powerful. And in fact, if you can get feedback from multiple sources, ’cause many people are data-driven, right?
Craig: If one person gives them feedback, they go, dude, it’s just you four people are saying the same thing. They realize there’s, there’s a problem. So let’s, uh, talk about great question posted in the chat, which is, what are the tools for motivating teams? You know, there’s only so much the founder can do on a Monday morning with a rah rah speech. Um, at some point you run outta rah rah speeches, um, you know, often you’ll get wins, uh, you know, you’ve got a customer bought something, close the deal, there’s a good feel, good moment.
Craig: But many of the times, you know, later stage in business things go on. What, how do you keep people motivated both as a team and, you know, personally? Yeah, I think it, I, I think the question, you know, it, it depends on what’s, um, what’s demotivating the team, right? Uh, I’m, I’m initially curious about, well, why isn’t the team motivated in the first place? What, what’s what’s falling down? So there’s, there’s some diagnostic there, but the first thing that comes to mind is, um, for example, in engineering teams, um, a lot of engineers who are actually spending time just on the ground actioning on X, Y, and Z feel massively disconnected from the purpose of X.
Craig: Um, they feel more and more as a team, as the organization grows more and more disconnected from what we’re actually driving and why, uh, disconnected from the outcome, basically. Um, and so that’s, that’s one thing to, to really consider. Is our teams, our individuals being, or do they feel looped in on decisions?
Craig: Do they feel empowered? Is there feedback being incorporated? Whether we disagree or agree, people are committing more fullheartedly when they feel heard and they feel part of something. And That’s super important. So what’s the means to do that? ’cause the problem is, you know, you can have standups and you can, you know, it might be said, you should over communicate, but you might have the contrary view. Dude, I just want to code stop taking me in all these, uh, strange meetings.
Craig: So I’ve got some thoughts on what might be a way to make people feel more included and so on. What would you suggest to the top few things you should be doing? Yeah, I think, I mean, town halls, um, at, at a, at a basic level are a great way to help people. You, you know, just be informed on a macro scale in terms of key updates in the business, where the updates, where, when, where the business is going, you know, key wins and such, um, you know, once a month or something for 30 minutes.
Anthony: Um, I, I think, um, you know, inside of team meetings, um, gaining feedback or sort of extracting feedback on X, um, and then inside of projects, um, doing, doing the same, I think is really important and seems to really help people feel included on key decision making in terms of, you know, say an engagement or et cetera. Okay. How about you, Anthony? Right.
Anthony: And I, and I think what I found, uh, certainly, I mean, it’s, it’s different inclusion across parts of the business, but certainly on the software developer side. Mm-hmm. You know, often developers, you know, particularly backend developers get a set of requirements that involve the word SQL or ML or something and don’t involve the word customer. And so they are developing things without knowing really what the business requirements are. So what I like to do is, uh, start each new, at least significant piece of work with a workshop.
Anthony: And the workshop is where the business owners, the people who are asking for it, explain why they want it, what customers are looking for, uh, and the developers are on it so that they understand the purpose, uh, of it, and also make design decisions. So, for example, if there’s a request about, you know, update, share registrar or something, yeah, you would know what the person is thinking when they want to do this. But by explaining why this is important for the business, the purpose at the time the customer wants to do this, this is in their mind.
Anthony: They, you know, have just closed a funding round. They’ve got investors wanting something, they need to do this. They dunno this, they’re gonna push this button, this has to be done in 14 days, or they’re gonna get fined. And suddenly the whole thing is brought to life. And instead of, uh, you know, a workflow that might have some small links, suddenly it’s got a big, you need to do this for 13 days left or something, because they now understand, uh, what the customer wants.
Anthony: So to me, that’s important. And also it just makes life a lot more fun. ’cause you can see the outcome of all the work you’re doing is not just a great, another GitHub ticket ticked it is these people are going to be loving what you’re doing. I think that’s, that’s brilliant. Um, sort of connecting the work to the actual customer and the outcome there, um, brings it to life, particularly when you’re on the ground. Um, sort of just as a part, a part of the whole one fun thing that I do often with teams, um, and it’s not in particular related to motivation, but whenever we’re, um, sort of, uh, spending time on decisions or projects, um, I’ll bring in two extra chairs, and in that empty chair is the customer, and then this empty chair is the, the board.
Anthony: Um, and what would they say, uh, what would their feedback be in terms of our decision going this way or that way? And or just in general in regards to this project? I, I, I like, I like that.
Anthony: That’s very clever. Yeah. So the one represents, you know, obviously your customer, pragmatic what someone’s gonna want tomorrow. And the other one is, does it fit strategically with, uh, you know, the, the, the goals of your company? So, so let me switch to a a point you made, which is, uh, recycling and giving away the Legos. Talk about that. What does that mean? Yeah, yeah. Um, so, you know, naturally, um, whether it’s a, a very founder, uh, or sort of vision focused founder, um, or a tech driven founder, um, they’re gonna wanna stay very close to that, that work.
Anthony: And as, as we’ve discussed, you know, evolving as an organization, evolving as a, as a leader, we go, um, sort of entails, um, recycling the role and doing different things from where we might have started, given away. The Legos is really about, um, recycling parts of your role or your job as either an exec or a founder or whatever it is in order to serve the needs that are emerging today.
Anthony: Um, in startups, that’s usually at about the three to six mark, three to six month mark. I see, um, roles looking, uh, substantially different, um, in terms of what executives, CEOs, whatever are doing at each six month mark. And so, given the way the Legos is about, uh, delegating work to your new, um, you know, product hire or your new, um, financial officer, or your new, you know, CTO, and it’s about moving into more of a leadership space, I think founders, um, are are really doing great when they’re, again, you know, both decoding, but they’re also delegating, they’re creating systems and processing and such.
Anthony: Okay. And I think you call this updating your user manual. Yes. Tell me more about that. Yeah, so, well, so the, the user manual, I think this is a really neat thing to consider for a lot of executives inside of growing teams.
Anthony: A user manual is, um, so for example, if I was your leader, Anthony, and you were onboarding, I would get you my user manual. And it’s basically a manual in terms of how to use me as a leader, um, how I like to be communicated with, um, what are my pet peeves, what, what, what to not do with me, um, how to work with me, what, uh, what are my values as a leader? Um, what, what do I expect out of those who report to me and or who are a part of this organization?
Anthony: Say one to two pages at max. And you can kind of emphasize, let’s say, three to five core components. But what this does is it accelerates the understanding and the relational aspect of our relationship. So I, I don’t have to, I don’t have to guess as much. Super interesting. So, you know, I, uh, insist on doing the final interviews at Seed Legals, even though we’re 160 people, I still want to do the final interview.
Anthony: And I start by explaining, um, that the call is as much for them to ask me questions as, as me, to ask them questions. And, uh, actually, I’m, I’m, uh, one of the key markers, I shouldn’t say this, is, the questions that people ask me are probably more important than the ones, the answers to the ones that I ask them. And usually they’ll ask, you know, like, how is the company gonna grow? And they’ll ask about culture, and they’ll ask about, yeah, what, what sort of attributes you’re looking for?
Anthony: And I always joke by, uh, saying, you know, when I hire people, I, you should never do what people tell you to do, particularly if it’s me telling you what to do, you should always think about why somebody’s asking, and then I explain you, I’m delighted, you tell me I’m wrong, much better you do that, then blindly do something. So, you know, and then, then that sort of explains the, oh, I mean, there’s more to, to, to explain the culture, but to, to show that everyone should be a mini entrepreneur. They should think like a product person.
Anthony: You know, there’s a slack channel for having product ideas. Now that creates one culture, of course, that, but then the CEO’s gonna be spending a lot of his or time hopping in and, and, and helping that. You might find the CEO wants to play golf. It’d just be much more hands off. So, um, now let, let’s, let’s, uh, I dunno if you’ve got any points on, on that. Yeah, yeah. I, I think that, uh, you know, as part of what, what we wanted to discuss here was, was how do we scale culture? How do we build culture?
Anthony: Exactly. Um, I, I think we’re building culture in every interaction we have on a daily basis. Um, in particular, it’s important for us to polarize culture in as many, um, you know, sort of conversation points as we can, what we are and what we’re not, um, how we behave and how we solve problems and how we don’t. Now of course there’s room for, you know, space for creativity and such there, but I think in the user manual, you fast track that in terms of, if you think of yourself, you know, whenever you sort of onboarded to any sort of org, particularly as an executive, um, one of the first things you are looking to do is to decode and understand what’s expected of you, what does good look like.
Anthony: Um, of course you want to go above and beyond that and sort of push, you know, what you see fit or what your agenda is. Um, but understanding the expectations, understanding how the culture works, which is essentially the mind of the founding team at first, um, that, that just gets us there faster. You’re smiling. Does that ring a bell?
Anthony: Yeah, no, Um, I’m, I’m smiling ’cause actually you remind me of, uh, something from a while back, which is, you know, where as you’re talking about culture and so on, I think people pick up all sorts of cues rightly or wrongly. And, uh, yeah, I used to work at the BBC, uh, quite a few years ago now. And when I arrived for like my interviews, I’d, uh, flown from Australia to London, got to the BBC’s, impressive big building, and was waiting for to view. And then I went to connect to wifi.
Anthony: And the, one of the wifi, uh, you know, channels was called, not With My Camel. And I thought any organization that would let somebody name the wifi network, not with my camel, would have to be an interesting one and would allow a lot of freedom of self-expression. So I thought that was kind of good. No one would’ve ever thought that a sort of a key, I wouldn’t say a key decision, but a point to, to hire or not would be made on that. And the other thing is, lots of people came from the tube station, the subway to the building.
Anthony: So actually I stood outside the subway and just looked at all the people coming in in the morning, and if they looked really miserable, I probably didn’t want to work there. And if they looked kind of happy, then, uh, then I did. And actually they looked pretty happy and excited to come to work, so I took that as a good cue. So they were all sorts of interesting cues that your team are gonna pick up on, you know, one way or or the other. So let’s, let’s wrap up on this. Oh, so let me actually hop in with a couple of questions, which is for the CEEO themselves.
Anthony: And then by the way, everyone listening, please put some, uh, you know, questions in the, the chat and we’ll get to those in a few moments. So I’m gonna talk about two things, which is chief of staff and, uh, ex you know, executive assistant, ea. So sometimes you come across a chief of staff role. I’m never quite sure about that. Is it this magic role where the CEO offloads a ton of stuff to somebody, or is it indicating some kind of failure on the CEO’s part to not be able to handle things and wants to play more golf and be outside of the company?
Anthony: Let’s talk about when and where and why a chief of staff might be useful. Yeah. Um, so I, I love a chief of staff role. Um, and I think it’s a very, uh, it, it’s a, it’s a tough hire first of all, uh, because I think it’s a lot about chemistry and it’s a lot about fit. Um, and, and let me say more, um, I think, I think a chief of staff, um, takes sort of the traditional EA responsibilities that an exec might have, which I think is pivotal.
Anthony: If you don’t have one, um, you get one as soon as possible. Um, as they’re gatekeepers, I think to sort of protecting your time and helping you prioritize. I think a chief of staff takes that, um, several steps forward and is really, um, when a good fit, um, your right hand person to, um, sort of, uh, you know, I mean they, what do they focus on?
Anthony: Operations? Um, they’re partnering heavily with the people team often. Um, they’re understanding the, the macro of the organization and help sort of advise you, um, as the company and the org grows in terms of, um, you know, they’re often observers in meetings. Um, they’re often there, um, you know, picking up on say what, you know, the relationship and, and how it’s falling down between marketing and sales and such, um, without really having an agenda because they’re not on either team.
Anthony: Um, I, I think that it, it’s a very, very key hire oftentimes at about the 20 to 60 person mark, depending on the organization. Okay. Index Ventures has a fantastic, uh, manual data driven manual that it’s created by surveying lots of, uh, top companies, um, uh, you know, between, you know, series A and unicorns to find out when they had certain key roles.
Anthony: You know, CTO basically by the time you three people, you kind of got A-C-T-O-C-F-O often arrives at, uh, sort of like 30 people. Two 50 people may be sometimes even later, a hundred people. Uh, chief of staff might typically arise, you know, at 150 plus sometimes more. Mm. So it’s interesting if you, uh, go and look at the, the Index Ventures manual, uh, That’s super interesting For, for, for growth and scale ups.
Anthony: There’s, there’s some actual data there. Alright, so, uh, can we, uh, wrap up by top tips from you on how to create a growth culture and what the CO and, you know, and, and top team should and should not be doing, and how to recognize if you’ve got a small slash medium slash large problem to solve? That’s great. Yeah. You know, I was thinking about this and instead of give a sort of a bunch of small tips which kind of might come out in the wash, one thing that I love to do with teams, so all sites are really, really important.
Anthony: I think as there are opportunities to, you know, we wanna be working as much on the business as we are in the business, or at least balance that. And oftentimes smaller organizations, um, exorbitantly spend too much time in the business. And so offsites a big fan, um, in offsites when I’m facilitating those. And this is what I would recommend.
Anthony: This is what, what I, what I, if there’s one thing I I think every, everyone here on this call should do is ask your team, your leadership team this question, who are we and who do we need to be? Don’t answer that question by yourself. You could also ask them three adjectives that describe this team. Three adjectives that describe who this team needs to be in six months time that we cannot use today. This helps us create a distinction between where we are and where we need to go.
Anthony: Um, and digging in on this with the team helps us sort of define the culture today, the operating behaviors today and what, and how they need to change and evolve because it’s different in every organization. I, I could, I could give you you all tips and, and sort of examples, but I, I think this is a better sort of, um, thing to think about for everyone on this call. Um, what you focus on in that conversation is not just those two things on either side, but the how do we get there that’s in the middle.
Anthony: What do we actually need to do? What is this saying about how we need to behave? Because leadership is essentially about what you do. It’s about what you think in your mindset, but essentially it’s about what you do. How do we need to behave? How do we need to, uh, interact? What do we need to do more of and less of to get here? Okay. Uh, that’s super interesting, the, the, the three words.
Anthony: Uh, but now and later that can’t include the word now. I think that’s sort of amplifying the difference between, you know, where, where you’d like to get to. Alright, thank you. So now we, so thanks for that. Now we’re gonna dive into some questions and I’ll, I’ll probably take the first shot at the first question, which is, is it a good idea to have separate workspaces for tech and business teams? Great question. Here’s my take. The closer the, the business works together, I think the better it’s gonna be.
Anthony: If tech is over here and business over here, you’re gonna set yourself up for a situation where the business keeps having feature requests and the tech team keep doing other stuff ’cause they’re just not interested in what the business is doing. But if they see the sales team and they’re playing soccer with them on a Wednesday night or whatever, and they’re mingling with them, when the person says, dude, you know, I can’t reach my targets ’cause too, too many customers are saying this feature’s not working, whatever, then they’re gonna be super motivated to want to fix it or help them.
Anthony: So bringing together is important, but one problem is tech team like to be quiet and work and business team is usually talking to customers between themselves. So you may need some physical separation, otherwise nobody’s gonna get any work done. ’cause they, they talk too much. And that’s kind of what we do at Seed Legals. The teams can work out wherever they want to sit.
Craig: And generally the tech team sit over there, the, the, the folks who do customer calls sit over there or encourage them to use phone booths and then they’ll all go play soccer together or whatever that they want to do as a team thing. Craig, your thoughts? I, I like everything that you said. I think, um, you know, the thing we have to be careful is, is uh, sort of a style of work. I think we call that out in terms of, uh, you know, business is all, you know, sort of, uh, you know, on calls maybe whether it’s tech or creative, right? There’s sort of more focus and such.
Craig: But I think, listen, one, one phrase that I love is, is this notion of, um, marketing isn’t killing it if the organization isn’t killing it. And what that means is we have to understand more about our different functions in the business. Um, and in doing that we understand how all the parts fit together and that’s where a lot of the magic happens in scale, right? Uh, from a leadership perspective, but also functionally. Um, and so spending time, spending ample amounts of time in proximity to and conversation with, um, in particular lines of the business that you normally would not, um, or unsuspecting lines of the business or, you know, functions that you normally would not, I think it’s extremely valuable and organizations don’t do it often enough.
Craig: And I think setting ourselves up in proximity to literally, um, is, is an important bit there. Okay, great. Thank you. So now next question, which is, um, should we consider the character in forming a team like aggressive guys for sales?
Craig: So do you wanna take that one first and then I’ll take that? Yeah, Yeah, sure. I, I think, I mean, it depends on your, um, you know, what, what are you selling? Um, and would would an aggressive person be a good fit for, for that particular product? Maybe, maybe it’s like, you know, in intense workout gear. I, I, I, I think it, I think that’s just one thing we have to consider. Um, I, I like to, to think about hiring for traits more so than skill sets. Skills are things we can easily sort of teach, um, although they have to have skills enough, but oftentimes what I see is that people over-index on hiring for skills versus hiring for traits.
Craig: And so if aggressive is a trait that you’re after, if you feel like that’s gonna be advantageous to the actual sales process or even team, it’s probably, you know, what does aggressive mean to you, by the way? I’m not sure we all have def different definitions of that, but if that’s a quality that’s a trait you’re after, then by all means. I think that’s, that’s great.
Craig: And go for it. Um, I think I’d be asking myself, um, what are the traits that would make this particular role successful? Um, and think, think about that a bit more in your hiring process and how to extract for those, um, balanced by of course the skillsets, which generally are, are what we, we sort of emphasize, uh, already. Okay. Alright. So thank you. And so what I find is that, you know, since I do the final interviews, I’ve got a nice data driven over quite a few people and you see the difference in the particular ones.
Craig: Uh, you know, software developers generally don’t want to talk to other human beings, which is just great. Uh, I’m obviously being slightly facetious, uh, when people join, uh, seed Legal’s customer support, it turns out lots of people study law at prestigious law schools and then don’t want to work for a law firm and then call seed legals and the characteristics of customer support. They, uh, you know, often technically, uh, detailed having studied law, but they just as a character trait, they want to be helpful.
Craig: They’re not tick counting the minutes that go by. They just want to be helpful. Whereas sales teams are the hunter killer submarines. They’ve got targets to make, you know, you don’t want someone who’s aggressive ’cause that just plays out badly. But you want someone who’s gonna be focused on making targets because otherwise the business will be great. We’re doing cool stuff and you’re never going to turn it into a growth business. So to me, those are the different characteristics I see in the roles.
Craig: And when I see somebody, you know, maybe are applying for a sales role who’s just thoroughly nice and wants to be helpful, maybe they a great person but may not be right, uh, for your sales ’cause they’re not going to be, you know, doing the calls necessary to make the quotas and or targets or whatever it, it might be that, uh, you know, depending how your company runs. All right. Next question. Great question. Important question. How do I retain staff?
Craig: I think you’ve sort of alluded to it in several different ways. Any top takeaway points there and, and how do, yeah. How do you recognize when you’ve got a problem with staff leaving? Yeah, yeah. Well, I think, so the the first thing that, the first thing that comes up for me is, uh, re retention is something we should be playing ahead of. Um, and, and so how do we create an environment that’s inspirational? How do we create clarity around career paths?
Craig: How do we create an environment where, um, you know, our the people working in our business have shots at, um, you know, bigger, bigger projects and such. What, what, what motivates them? What are they there to learn? That’s, that’s a key question I encourage everyone to ask when they’re hiring. For example, what do you, what are you here to learn? What would you be coming to this organization to learn and ensure that that is part of what you’re getting in front of them? I think that’s a very, very cool part of how we can retain people is understanding what their career trajectory is.
Craig: What are they after, uh, in terms of not just skill sets, but there might be other motivations. What are their motivations? Um, what are they hungry for? And ensure you’re engaging conversations around getting them to that. I think, I think sending moti se sending a, a message not just of of your motivation or your intention, but showing them that as well through your actions. Those are some core pieces, um, that come to mind when I think about retention.
Craig: Okay. So let me ask then, um, one of the characteristics is, is being nice, important as a CEO. So, you know, you read about some who are, you know, basically a******s and, uh, but they super motivated, they super focused, but you know, they’ll trample egos, time personalities, whatever to get there. And maybe that is an attribute of success or maybe you don’t want to work for them, whereas others, you know, maybe yourself, you’re like, you’re super nice, you don’t wanna be confrontational, you didn’t make your targets.
Craig: It’s, you know, uh, life’s okay. You know? Um, should you as A-C-E-O-C being liked as important or respected or feared, uh, take us through that quickly. Yeah. Well I think that, I think being nice is a, is a great attribute. Um, I think we all, um, hopefully aspire to be a kind and empathetic person.
Craig: The problem is when is, when that goes too far and we’ve over empathized with our, our employees or our, our organization. And what I mean by over empathize is, is we’ve, we’ve sort of enmeshed with their experience. We’ve, we’ve over identified with their emotional experience. We want them to like, to like us. And so we’re more attached to, um, you know, their emotional experience and having them feel good then, um, attached to what is best for the business. And so I, I think, um, you know, the, the focus has to be on what’s best for the business.
Craig: Um, and, and if your behaviors that are driven from there, um, have an impact on somebody that’s, uh, less than desirable or hurtful, um, I think as long as you are being skillful about whatever message that you’re delivering or feedback and such, um, people not liking you as a result of that is, is just a part of what you signed up for.
Craig: Um, and so I think, I think sort of en engaging in a stance of, of I have to be liked as a CEO is extremely, extremely dangerous. And developing a tolerance for not being liked as soon as possible is, is really advantageous. But that doesn’t mean we have to be not nice per se. It’s just, it just means we have to make good business decisions and be compassionate about that, but not be overly involved in the emotions of other people.
Anthony: I think self-awareness really comes into play here in terms of what are your motivations and where, where does this sort of, uh, get in the way? I have a hard time setting boundaries with you, Anthony, because I am afraid of you not liking me. Um, I mean, that’s a great thing to take up with a coach. Um, right. Or, or whatever it is. Um, that’s a, that’s, that’s, that’s a real problem. Um, whenever CEOs especially can’t have challenging conversations, um, particularly around performance and accountability.
Anthony: Okay, interesting. I think you sort of indexed slightly further away from niceness than I was quite expecting and more on, you know, the performance and, you know, the mission I I, which I, I think is, uh, super interesting ’cause obviously, you know, you want to balance, uh, you know, having a great team and great culture and you want your interaction with each team member in general to be positive un unless you want the team members shortly to be exiting the business.
Anthony: Um, and, but then that is difficult if things aren’t working out or there are challenging conversations, right? So I think that’s one of the, the key day-to-day things that might be concerning you, where you position yourself in that steam roller that’s gonna run over everything versus you’re super nice and, uh, open the door for everyone, but, you know, uh, things Are not Aligned and performing. And, and, and I, and I wanna be clear, I think it’s, I think it’s important to, um, you know, as a CEO to allow access to yourself to be involved in the business, to be curious about and, and, and sort of understand the world of others.
Anthony: Um, I’m, I’m definitely not saying don’t do those things. Um, I’m, I’m simply saying, um, as, as a coach who, you know, last year alone, I think I worked with 30, 40 plus CEOs, um, buy and by what I see is, is the, the opposite.
Anthony: People are struggling to say the hard thing to have the, the challenging conversation. They retain low performers for way too long, um, and focus way too much on relationships versus the business. I think there’s a balance there, right? And, and we have to look at ourselves, um, and, and practice some self-awareness in terms of are we over indexing on relationships or are we overindexing on business? Um, my, my experience has been, um, the vast majority of founders spend way too much time over indexing on the business, or I’m sorry, on relationships.
Anthony: Interesting. Okay. So it’s a wrap. Top five things you think that you’d offer for anyone watching these things to do things not to do. These are the top five things, if I can put you on point for five things. Yes. Uh, let’s see. Top five things. Um, I, I think, I think considering your, your communi, so as your team grows, considering your communications across the team, um, and setting up systems in a process for getting the right updates to the rest of the team in time, I think is a huge, a huge win.
Anthony: Um, setting up a proper one-to-one structure I think is another huge win. Um, really considering how are you sort of setting and aligning around priorities in the business with your team members, I think is, is a key bit. Um, let’s see.
Anthony: Um, yeah, I think tho those are, uh, five, I’m, I’m kind of like swinging here. Um, yeah, that, that’s, that, those are the, the ones that stand out for me. Okay, good. And then we’ll just wrap with a really fun question, uh, which is, is being a thought lead on LinkedIn a requirement for CEO to have a successful startup these days? Because the jury’s out, right? I mean, the LinkedIn feed is filled with self izing posts and so on, but on the other end, you, you both despise and wish you could do the same.
Anthony: So what are your thoughts? You know, I, I think, um, I, I don’t think it’s necessary. I, I think, um, I’m all about zone of genius and if it’s, if it’s something that can be valuable to the business and it suits your strengths and it’s energizing to you, um, I, I I think do it. If it, if it does not suit your strengths and it is draining, um, and there’s just not enough like evidence for an ROI on the business, why would you do that?
Anthony: Why would you spend time doing that? It really seems like a, a bad choice to me. So I, I don’t, I don’t think it’s necessary. I, I, I don’t, um, I think that there’s a lot of, um, pressure to do so. Um, but I think, and, and I, and I think that there’s an incredible amount of, um, upside to those who do. Um, I don’t think that it’s necessary to build a solid business, however. Okay. And I think my answer to that is, uh, you know, uh, is to be genuine in all things ’cause people spot fake so easily.
Anthony: And if you genuinely can find something that you’re passionate about, you may have to prod yourself. ’cause you might be that INTJ that you know, um, would just focus on writing documents, but you have to put yourself out there. But if you can be the thought leader on something and might need a bit of a push, but it really, you found that sweet spot. You’re not tweeting or the LinkedIning about random stuff and so on, but there’s something that you going to become known for, um, yes.
Anthony: That you’re the champion of, that you’re the thought leader on, um, and that people see your words. It’s not just promoting the company, but some valuable thing to help your reader. Then I think it’s something, certainly I have grown to love. It does take some effort, you know, at midnight when you prep what’s gonna go out on LinkedIn in the morning or something like that. But you hope with each post that it is something that, you know, where you to meet someone in the street after it’s going, Anthony, I saw your post.
Anthony: They, you hope they would say it’s helpful, rather, dude, stop putting rubbish out my way. So Yes, e exactly. And that, that’s kind of what I meant by, um, you know, if it, if it suits you, um, we, we have to sort of, uh, come from an authentic place. Um, and sometimes, you know, we, we have to use our voice to find our voice. And so sometimes that’s the process, right? We, we, we sort of, maybe we’re not energized by it, but we can get too energized by it because we find our voice through used in our voice.
Anthony: And so that’s something. Um, but I, I think that there’s, uh, and, and you do great with that, Anthony. It, it seems to really suit you. Um, I enjoy all of your, your content and, and just kind of what you’re doing, um, by the way, you know, in terms of, I, I think it’s there, there’s a bigger purpose to it and it’s about serving the community and getting value in the front of your community. Um, and, and I think that’s, that’s just great. But doing something such as, you know, sort of focusing on your individual brand just because you should, that’s suspicious to me.
Craig: And, and I, I, I wouldn’t buy that at face value. Alright, so thank you so much Craig. Now what should people reach out to you for and where can they find you? So yeah, they can find me. Uh, boy, I mean I imagine my, uh, credentials are, you know, somewhere attached to this, this podcast. But you can find me at, uh, Craig, at new bo newburg gore.com. You can find me on LinkedIn.
Craig: Um, and I, I think consider or consider contacting me or calling me if you are looking to drive performance inside of your team, build solid relationships and, uh, really understand what’s necessary and scaling your organization. Alright, Craig, thank you so much everyone on the call. Thank you so much. I hope this has been helpful and, uh, reach out to me or Craig if there’s anything that we can help
