EP24 - Teamwork is harder than you think (Part 2 of a series)

Alex Hillman: All right my friends, we are back for part two of our series about the things that Amy wishes someone in the world would have warned her, put up a big flag or something, and said, “You’re about to start a business, a SaaS business – watch out! This stuff’s coming!”

Amy Hoy: Actually, there’s a reason I titled the blog post, “Things I Wish I Had Known”, because some of the stuff in my list is the kind of advice you’ll hear from people, and then you believe it won’t really apply to you – until it’s too late.

Alex Hillman: You know, it’s funny that’s something that I think we see a lot; there’s all kinds of things that we – on this very podcast, or in our class and our blogs, we write about it. People – it’s not that they don’t believe us – some cases they don’t believe us, but there’s a certain element you need to experience to go, “Oh, maybe that’s what that was”.

Amy Hoy: “Yeah, dude I can totally sell to restaurants and bars for my scheduling software.”

Alex Hillman: Yeah.

Amy Hoy: “What are these guys talking about? It’ll be easy. They really need it!” …Oh…

Alex Hillman: We’re not talking about restaurants and bars, or even technically scheduling software, but the second topic in this series of five is about teams. It is about people.

Amy Hoy: It is about people and why they suck!

Alex Hillman: Well, let’s hang on a second. No, no people don’t suck. There are people who suck – no doubt, but people are definitely difficult.

Amy Hoy: There are many individuals who are wonderful, but in the call to perform roles, they may not be so wonderful.

Alex Hillman: All right, let’s go so far as to say people are harder than you would think.

Amy Hoy: Yes, okay. We can agree with that.

Alex Hillman: More challenging. I think the title of the section of the blog post was “Teams are not ‘Just Add Water’”

Amy Hoy: Teams are sea-monkeys.

Alex Hillman: Go on.

Amy Hoy: Surely everyone of a certain age was mortally disappointed as a child by sea-monkeys?

Alex Hillman: It seemed like it was going to be a good time.

Amy Hoy: Yeah, they looked cool. They were wearing crowns. They had furniture in illustrations and in the magazines where you would buy the sea monkeys from looked they were going to be this really cool pets.

Alex Hillman: And there was even the cartoon. Did you ever watch the cartoon? The cartoon was creepy! As you can imagine a cartoon about sea-monkeys would be a family of sea-monkeys as you just described them, but as cartoon characters. It was sort of in that category of like Smurfs and Snorks, but not really. It was in that time period. It was not good.

Amy Hoy: I’m pro-Snork.

Alex Hillman: I’m also pro-Snork! Another day I want to find out why you’re anti-Smurf. Not today. We’re going to table that one.

Amy Hoy: Bottom line is they’re creepy. Anyway, sea-monkeys in the ads and on the box you’re like persuaded by the graphics. They’re going to be like really cool and interesting to watch, and they’ll be like doing stuff. And then you add the water and then they’re just fucking shrimp! They’re like water centipedes – too many legs! They don’t do anything.

Alex Hillman: So, disappointing. They certainly don’t sit in their furniture and like have little like shrimp family conversations.

Amy Hoy: No, they don’t even fight or anything. There’s literally nothing interesting about sea-monkeys except how they persuaded you, that brine shrimp, were like somehow going to be a cool pet. It’s a story about marketing and not substance.

Alex Hillman: You know, I never really thought about how weird the name sea-monkey was, and nothing they actually described is actually monkey-like. It’s very strange. So, we’re not actually here to talk about sea monkeys though…

Amy Hoy: You’re not…

Alex Hillman: We did want to talk about the fact that, maybe like sea-monkeys, a lot of people think of teams, collections of people, when you start introducing people to your business – we’re not talking about customers – that’s a whole other category. This is the teammates. This is the partners. This is the support staff.

Amy Hoy: Contractors, or service providers…

Alex Hillman: The human element of business outside of the customer business relationship is remarkably, remarkably challenging. Yes. And I don’t think people prepare themselves for that.

Amy Hoy: It really is. Well, everything out there that’s written about teams are like, “Oh, my awesome team did this” or, “Oh, my awesome team did that”, or like “Hire the right people and get out of their way”. It’s like, everything is a lie. It’s such a lie.

Alex Hillman: And there’s an entire, I mean think about the entire startup business parable. There is a main character in almost every startup story of the fabled co-founder or co-founders and how that match, that perfect match, led to success, or the perfect teammates led to the ideal success. I mean, it can happen. It CAN happen, in a world of things that can happen, but it doesn’t always go that way.

Amy Hoy: I think it almost never goes that way.

Alex Hillman: Why don’t we rather than speak in circles around something, a vague frustration or a lie, I think it would be useful for us, you know, I don’t think a lot of people talk about this because it’s kind of tough and we don’t want to come across as accusatory.

We don’t want to really shine a spotlight on somebody to be like that person screwed things up. But, I think there’s a lot of value in if you’re going through difficult interpersonal relationships with your team to realize that, you know, this isn’t just, you. This is tough and you might not be doing something wrong, but you’re in a situation that needs correcting.

Amy Hoy: So you’re a much more politic, shall we say, as in polite than I am. I’m not obviously going to name any names because you know, legal stuff, but I have a burn book in my mind!

Alex Hillman: A burn book, as in people who you would not…

Amy Hoy: You haven’t seen Mean Girls, have you?

Alex Hillman: I have, but I don’t remember that part!

Amy Hoy: Okay, a burn book is where you write shit about people.

Alex Hillman: Okay.

Amy Hoy: Not now that you’ve burned the bridges, but like literally write all the nasty things you can think of as this book. Anyway, I don’t actually have one. I just sort of think about it sometimes. I think that the best strategy with this podcast episode, if I can encourage you to do one thing, it is to shield yourself from other people in your business until the last possible moment, frankly.

Nothing will kill your motivation more than working with someone who makes your life hell. If you have an unequal partnership or you feel like you’re doing all the work or worse yet, they’re actually undoing your work and then you have these seething resentments or even arguments or yelling, or then there’s fights over who owns what – that will kill your business instantly. Very little will survive that.

Alex Hillman: I agree that people jump into these interpersonal relationships often too fast and too early. I think it maybe would be good to qualify what the last-minute sounds like because that sounds like somebody, maybe burden’s not having somebody around for a little bit too long or in the wrong situation.

Can you talk a little bit about when you have found is the right time to have somebody – whether they are a partner, or a team, or that contractor, support staff sort of thing. When do you actually decide, it’s not too late, it’s not too early, I think this is right?

Amy Hoy: So, I’m no expert on hiring at the right time, but I can tell you all the times when it’s not right. Do not start a partnership with someone when you don’t have a product.

You think, “Oh, well they have this skill and I have that skill. So therefore, it will be a perfect marriage.” Well, a marriage between somebody who works and somebody who does housework, or somebody who likes to vacuum and somebody else who likes to do the dishes, that’s not what a marriage is founded on and honestly, starting a business with someone is as serious as marriage and actually in a lot of ways, harder to dissolve if you’re over it.

Alex Hillman: Yeah. There are assets that are more difficult to untangle, in some cases, legally, but also financially. Undoing a business is as hard, if not harder, than undoing a marriage in a lot of ways.

Amy Hoy: Most people I know who’ve had partnerships that went south, ended up just dissolving the company entirely and no one got anything and the product was dead.

Alex Hillman: Right.

Amy Hoy: What a waste!

Alex Hillman: So, to try and crystallize that a little bit, partnership that starts from a, “we are going to come together and make a thing, but we haven’t really decided what that thing is even yet, or more importantly, a thing doesn’t exist yet.” The abstract idea of partnering to start a business…

Amy Hoy: Don’t partner to start a business. Bottom line.

Alex Hillman: Now what about when there is a preexisting relationship?

Amy Hoy: I think that relationships work best when someone is clearly the person who is the decision maker. I’ve seen partnership-partnerships work, but much rarer than a situation where one person is like the final decision maker.

So ideally, if you decide that you later need a partner after you’ve been running your business for a while, then you are in a position where the roles can be clear. The ownership can be clear who is in charge can be clear. That actually is much easier to manage. Lawyers and accountants will probably tell you that a 50/50 business is a big fat mess.

Alex Hillman: Yeah, and I’ve seen a handful of different configurations, whether it’s a 40/60, like you and I have, or my other business with Geoff is a 51/49, and that one’s an interesting one because it’s literally a 2% difference. In our operating agreement what we drew the line was, if I’m ever using my 51% to pull rank, we essentially use that as a clue that there are bigger problems afoot.

Amy Hoy: But Geoff’s like never around?

Alex Hillman: Well, that’s today. But back when we were making early decisions and even up until this point, the business partnership that we have works because Geoff and I understand and have made it clear how we’re going to make decisions, what the expectations are and all of that. When you try and set all of that up before a business is in motion, you’re sort of inventing what might be.

Amy Hoy: It’s play acting. It’s basically playing house. Now you said, if you don’t know what the product is, like no, back away! It doesn’t matter how clear you think you are about what the product will be, or what the roles will be. It’s not going to work basically 95 times out of 100 it’s not going to work. You’re just dooming yourself.

I say that as someone who actually has two separate businesses with business partners and we initially started Freckle with partners and that did not work.

Alex Hillman: Do you want to get into any specifics about what expectations did not play out the way you expected them to?

Amy Hoy: So when I wanted to start Freckle, which is obviously a Software as a Service business, software service businesses grow slowly in almost all cases, no matter what you do. A Software as a Service can only grow so fast. Right. So that was understood and stated and agreed upon with our development partners early on, when we started Freckle. I had a design, I had a plan, I had a marketing plan, all this stuff.

I had all this stuff and we agreed that they would have profit sharing of a certain amount, over a certain period time. When it didn’t grow fast enough, they just sort of stopped working on it and they got pulled away to do other consulting projects and then they kind of wanted to renegotiate the terms where they only worked on it, like every three weeks. I was like, no, that doesn’t work. Even though it wasn’t making money at that point – making much money anyway. That was like a year in and I bought them out. We’d always agreed that our friendship was more important than the business and they actually followed through with that. So, I offered to buy them out when I didn’t owe them anything and they accepted the buyout when they didn’t have to, essentially.

Alex Hillman: I think you just said something that is very, very easy to say, and very, very hard to execute, which is the friendship being more important than the business.

Amy Hoy: People will say anything, and they will even believe it and most of the time it’s a lie.

Alex Hillman: I think one of the hardest parts of any sort of partnership or collaboration – I think maybe the mistake that people make is you spend all of your time thinking about how you’re going to divvy things up when things are going right or even great, but it’s very hard to think about how you’re going to want to be or act towards each other when everything falls apart.

Maybe that’s one of the most important parallels between personal (whether we’re talking romantic or not) relationship’s and business relationships is that the defining moments often are how you act towards yourself and each other when things have fallen apart.

Amy Hoy: Most people are bad at this.

Alex Hillman: Especially because if you’ve never been through it before, back to what you’re saying about, it’s like role playing. It’s very hard to imagine how you would actually be towards someone when things go south. So I can speak from my perspective, having been in a similar situation, but on the other person’s side and also having the same relationship where the friendship mattered more than the business.

Amy Hoy: You’re talking about us, right?

Alex Hillman: I’m talking about you and I.

Amy Hoy: Yeah. So, having not sufficiently learned my lesson with our development partners on Freckle. I mean, I ended up crying a bunch, but it all worked out okay. Then when I wanted to create this class, the 30x500, the very first one called the Year of Hustle. I was super buds with Alex and I was like, we should do it together because we would mesh really well together. And so, you came out to Vienna and we white-boarded the whole thing. Then we started working on it, and you dropped off the face of the earth!

Alex Hillman: Just to qualify what happened there, that was not for a lack of desire or lack of growth. I made a mistake in that I over committed myself and I had taken on a couple of other consulting projects at the same time, and they both sort of ballooned a little bit out of my own control and that was my own learning curve there. But when I found myself in this position where I was like, I’ve made a commitment to more things than I can reasonably do. Something’s gotta give, and I know the place where I’m doing the least version of what I know I’m capable, or what I’m expected to do is my work with Amy. I was just not following through.

Amy Hoy: As I was on the other side of the world actually, slowly working up the desire to throttle Alex, he actually came to me and said, “I’m being a shitty partner. Here’s your money back? Sorry.” Which made all the difference in the world because instead of being agro and expecting to work less for the same deal or a similar deal, he was just like, “I screwed up. I relinquish my claim on the money and let’s still be friends”, which would work for me. Clearly, because we work together now.

Alex Hillman: Another part of that from my side of the table, and perhaps it’s useful to somebody else is really, I’m always thinking about long term and it’s not just that I value the friendship – though I do. It was that if I ever wanted a snowball’s chance in hell of us working together on something again in the future, ever – if I could possibly imagine the desire for that to be the case I need to do right now, so I can keep that door open in the future.

Not that Amy would necessarily want to, although obviously we’ve made different decisions along the way, but that was my long view in that. It’s hard to do, and if I had brought in that money or already spent that money, I might’ve had to make different decisions. I might’ve, I don’t know. There’s no way to know in an alternate timeline, would I have taken some of my consulting money to pay it back? I like to believe that I have the integrity to have made right on it in the back way possible.

Amy Hoy: I believe you do.

Alex Hillman: But hard part of this, again, regardless of which side of the table you’re on, is looking at this and going, just because on paper, someone is my partner doesn’t mean I have the right to something.

It’s about what makes the situation equitable. Things change. Partnerships are drawn on paper, but reality changes. You have two options. You can either change the reality or you can change the agreement – and it’s that simple.

Amy Hoy: Most people won’t. Mt people won’t admit that they’re wrong. They won’t fix their mistakes. hey will get angry when you’ve pointed out that they’re doing something wrong, instead of

“sorry”, there’s a fancier word I’m looking for…

Alex Hillman: Apologize?

Amy Hoy: No, no, they will feel bad and then make amends. Most people won’t. The fact of the matter is a person can seem like a good friend or a decent human being until you get in a work situation with them, where they feel that they have ownership and then they become entitled and then they slack off and then they get aggravated when you point out that they’re not doing their job. I’ve seen this happen so many times, one partner is doing all the work and the other one still feels entitled to their share or their money because “I’m a partner”. It’s not a good situation. It really ruins relationships and it ruins products and it ruins businesses that would have otherwise had a great potential to succeed.

Alex Hillman: Yeah, I agree completely. I think at the heart of all of this, that sense of entitlement is really at the core. If you are going to put yourself in a situation where you have partnership, I think one of the best personal antidotes to that is to make sure there’s some form of gratitude in your own practice, in your relationship, stepping away from the work and sort of like appreciating each other, appreciating the work. That is hard.

If you’re getting into a partnership and expecting it to just work by working together, you’re fooling yourself. By making sure, I think if there’s a practice that you can introduce into partnership, it’s gratitude. That sounds a little woo woo and fluffy for us in our conversation, but it’s something that you and I have talked about a fair bit, Amy.

Amy Hoy: But I think that there’s no amount of gratitude that will fix most people because of their shitty partners. So, I’m like, just don’t do it! Don’t do it until you have the money and legal resources and everything, to be sure that everything will be fine, no matter what happens.

I suggest not doing it. Don’t form a partnership, especially don’t form a partnership because you think this other person will fill some role that I need. That is a terrible reason.

Alex Hillman: I agree with that completely.

Amy Hoy: Terrible reasons are a partnership and that’s why almost a hundred percent of partnerships form.

It’s that we’re like, “it’s fun. It’ll be fun to do something together”. That’s also terrible.

Alex Hillman: It’s like marrying from money or looks, right? It’s like you complete me. And I’m like, “ah, that’s probably the wrong reason. That’s not partnership.”

Amy Hoy: Right, it’s using someone. Fail. That actually brings us to hiring people I think.

Alex Hillman: It does.

Amy Hoy: You think that you’re hiring for a role. You’re like,” Oh, I don’t want to do email support anymore. I’m going to hire somebody for that”. That doesn’t actually work out well either.

Alex Hillman: Why is that?

Amy Hoy: So for starters, people tend to look at employees as simplifying or reducing their workload and unless you hit a gold mine, that’s actually not what happens. Even if you do hit a gold mine, you first have to dig the mine before you can get the gold, which means more work before you have less work.

Alex Hillman: Right. It’s not as simple as outsourcing, tasks are not fungible. Even when you know, you’ve got good documentation and a training process and things like that.

Amy Hoy: I think we’ve all gone through the experience, specifically with support, of using a company and everything works great when the founders are doing the support and they start adding staff and the staff are terrible. It’s because the founders thought that they could just plug in employees and not put them through rigorous training and monitoring their work and checking it and reworking it as necessary, and training them. Then support gets really bad and then people get really angry. That’s all because the founders didn’t understand what it meant to have an employee.

Alex Hillman: So, in this particular case, the mistake here in a lot of cases is hiring for a particular skill. You said for a role, whether that’s support or something technical or really whatever it is when you’re bringing somebody in, you think you’re bringing them in to do a job. to a degree you are, but how do you turn that around? Having now hired and had to learn what it is that you’re looking for, do you have a sense of what makes a good hire?

Amy Hoy: Sort of! I don’t have great people sense for hiring, which is why I’ve been asking Alex to double check my choices. I don’t like people; I think is what it comes down to. Actually what it comes down to is I’m very optimistic because I look at a person and what they’ve been doing, and think you’re more than capable of doing this thing I asked you to do and I’ll help you, but you can do it. Most people really don’t react well to that.

Most people do not actually want to learn or stretch or grow at all. So I have to learn to not be at all helpful and to see what people do if I basically ignore them.

Alex Hillman: So it’s the capacity when you see someone and regardless of where you’re hiring them from, whether they have the capacity to do the work is not the same as the momentum, the desire, the drive to sit down with a task and actually see it all the way through, or even to hit a roadblock and then ask for help?

Amy Hoy: In my experience, the average person who was an employee at other companies and might apply for your job, is used to being told exactly what to do. Not really monitored, because they work at a larger company and then their mistakes and stuff go unnoticed and they are not used to proactively looking at their own work. They’re not used to finding something to do. They’re not used to making processes more efficient or any of these things, all of which you can teach, but which are extremely intensive to teach because you’re essentially trying to turn them into a new person.

A person can work really well at a role in a large company and work terribly as an early employee in a small company because they’re actually made to be a cog. It’s not that that is all they’re capable of being, but it’s all they’re capable of being now. So, you don’t want to take on a remodeling project.

It’s really hard because if you look at someone and you see their potential, it doesn’t matter what you seek at all. It only matters what they see.

Alex Hillman: So the flip side of that and what I’ve been trying to do, what I’ve done in my own hiring and what we’re now working on together is looking for, it’s a nuanced shift. It’s seeing people for their potential, but it’s more about their potential momentum, their desire, their drive, their curiosity. Technical skills, unlike those professional skills are teachable. I think that’s what we’re talking about is the delineation between technical skill and a professional skill.

Do you know Dan Mall? It’s a designer here in Philadelphia. So, Dan’s been running an apprenticeship program sort of quietly for the last three or four years out of his design studio.

Amy Hoy: Never heard of it, so it is quiet.

Alex Hillman: Yeah. And he really just started talking about this in the last couple of months and one of the really interesting things is he specifically hires people who do not have any design background or skills whatsoever. From the technical side of things, he says, “If you’ve ever picked up Photoshop, you are less likely to be a candidate for this. I don’t want to have to unteach you bad habits.”

Amy Hoy: Give me a child of seven type-situation. Nice.

Alex Hillman: But here’s the thing. The way Dan has structured the teaching of the design skills is it’s all wrapped around skills of professionalism, things like estimating time and effort, things like breaking big things down into smaller things. Things like communicating, progress, updates and it’s brilliant. It’s absolutely brilliant. Part of the reason I know it’s brilliant is because when we were talking about the outcomes of, well, what happens then on the other side of this apprenticeship model, is a lot of those people come in because they want to get a job in the industry. They want to get a job, being a designer at an agency, some of them want to be freelancers and Dan then uses his network to help connect people with potential jobs.

Amy Hoy: That’s really cool. That is really cool.

Alex Hillman: Here’s the cool part.

Amy Hoy: That’s not the cool part?

Alex Hillman: When Dan places one of his apprentices and six weeks later gets a phone call, not even six weeks, like two or three weeks later, he gets a phone call from the person who runs that agency and says “How did you make this person billable on day one? I’ve never hired somebody who was billable on day one”, and you maybe as an employee, know what it’s like to not be billable on day one and if you’ve ever hired somebody, you know exactly what I’m talking about.

There’s a handful of days at the very least and I think the common theme between what Dan is producing, the person that is coming out of Dan’s mentorship and the people that I actively seek when I’m trying to hire, is someone with those professionalism skills in place, because on day one, they can be billable if they have the capacity to be professional, they have the drive, they have the motivation, they have the momentum, they have the skills – that’s built in, that is habit. If I have to teach that, that’s why you’re not billable until day five or 15 or 50 or never. Right?

Amy Hoy: Absolutely.

Alex Hillman:. So, looking for those professionalism skills, and you mentioned before, you know, a trial period.

Amy Hoy: Yes. We only do trial periods now, I’ve learned my lesson.

Alex Hillman: So what does that look like?

Amy Hoy: So a trial period is usually three months with a specific project, so it can be a contracting gig. There’s a specific scope. And there’s a specific project and there’s a specific price. So it’s structured exactly like a consulting engagement. Then at the end of that, if everybody’s happy, then make a job offer.

Alex Hillman: And that’s if everybody’s happy?

Amy Hoy: If everybody’s happy.

Alex Hillman: That’s the other thing is, is we often look at this as a, “I have a job and you get the job.” But even when there is a positional delineation, if both people aren’t getting something out of it and I’m going to go so far as to say, if all there is exchange of money for work, it’s not gonna last.

Amy Hoy: No. I personally find interpersonal stress to be extremely draining. I know how woo-woo special-snowflake that sounds. But with my health issues, it literally makes me sick to my stomach to deal with people who are not pulling their weight and I’m sure vice versa. If I can’t provide what they need, then I feel bad. So, it’s really important to see how a person does if they’re kind of pushed off in the deep end, how do they actually manage a project. Of course, there’s going to be unknowns. You don’t ever just hire a support person and all they ever do is email support, unless you’re a big company with money to burn.

Alex Hillman: Yeah. One of the things that I think has worked best for me and having learned throughout all these stages and attempts and phases is to be as clear as possible, upfront about the expectations, not about the expectations of what they’re going to do, but that you expect them to be in dialogue and improving it.

Something you said very, very quickly before is looking for things that need doing, a lot of what I try and remind people of – and this is not attractive to everybody - and maybe one of the fastest dividing lines between someone I’ll hire and someone I won’t, is the person who their eyes light up at the notion of part of your job is to make this job better.

Part of your job is to design your own job, to look for things to do that need doing, come to me and say, “Hey, I think this thing needs doing”, in the best of scenarios even have a little bit of a game plan of here’s how I want to approach it. For me – and I’m totally comfortable saying this up front to somebody – if that’s interesting to you, then this job might be great for you. And if it’s not, that needs to be okay as well.

Amy Hoy: So I have said all of that type of thing to people when we have been preparing to hire someone, like there’s no grotwork in this business, we all do it. Then I have still managed to hire people who say the right things at that time, and then get bitchy when we expect them to do the dishes once, when obviously Thomas and I own the business, and we do that kind of crap all the time.

They thought that it wasn’t in their job description. Someone once told me, “It’s not in my job description”. Needless to say that person didn’t have a job for very long. I am an up-front communicator, but if you go and you set expectations, you talk about this stuff, people will say, “That’s fine. Works for me”. And they’re lying.

Alex Hillman: What people say and what people do are very different things, which is the reason for this trial period and letting people have an opportunity to show that they will look for things to do.

Amy Hoy: Some people really like to tell you that, “Oh, the key to a good relationship is communicating.” No, the key to a good relationship is being in relationship with a good person. You can communicate all you want, but if they’re not the right person, it won’t matter.

Alex Hillman: Maybe to unpack that just a little bit more, without drawing a line in the sand between good and bad, because I think there are even good people who aren’t consistent.

Amy Hoy: I’m not saying this person with the dishes was a bad person, but she was a bad employee.

Alex Hillman: So we’ve talked about partners, we’ve talked about employees, what about, and maybe this one is something that doesn’t come right away, but at a certain point, you do need to “outsource”, at a certain point, you’ll be doing your own bookkeeping, but then you really need to hire somebody else to do the bookkeeping and file your taxes…

Amy Hoy: Fly your taxes?

Alex Hillman: Did I say fly? File your taxes, all this, like ancillary very support operations things. Things that at a small business size, you probably don’t have a full time CFO.

Amy Hoy: No, but that would be lovely!

Alex Hillman: It would be lovely!

Amy Hoy: So I think that actually the rule for hiring employees and hiring contractors is exactly the same.

It took me two or three times before I learned that I can’t just hire an accountant and then trust that they’ll do their job. It really took me way too many turns around that particular awful merry-go-round before I figured that out, that the core problem, they did a bad job, but the core problem was that I trusted them to do their job without oversight. Contractors actually generate more work. They do. That’s just a matter of fact,

It’s like, is it better for me to outsource my task operation? Yes, because I literally lose 50 IQ points when faced with a form. I can program, but I cannot fill out a tax form. My brain will explode, so I must outsource it and it’s a matter of learning that I have to oversee the process and I have to keep checklists and dates in mind and check. And I now have an accountant that’s proactive and does everything that they’re supposed to do and more and reminds me to do stuff.

If I hadn’t had a better management of the process before, we would have had a lot fewer problems. The same thing goes for designers, developers, writers, support people, video editors, whatever. You think it’s really tempting to believe that you could just slot somebody in and they’ll spit out work an be done, and that does happen very rarely. But most people have to be managed, even if they’re contractors.

Alex Hillman: I heard you say something in the description there that you give someone work and trust them to do their job. I talk a lot about trust and I think the thing to think about is you can trust someone to do their job once they’ve earned that trust, and the title, the “ability to do the job”, maybe that’s the theme through all of these things is trust is slow to earn and fast to burn. Not to intentionally be a poet there!

Amy Hoy: You’ve just coined!

Alex Hillman: No, I didn’t coin anything.

Amy Hoy: You’re not supposed to coin in public, Alex.

Alex Hillman: Sorry, but that’s true! It doesn’t take a lot to earn trust, but it does take effort. And if you can do something in your partnerships, in your hiring of employees and you’re seeking of contractors, sort of creating an opportunity for that trust to be built before you rely on that person. It’s very hard; I would argue impossible to make a decision about whether or not you should rely on a person. Sight unseen. Trust needs to be earned. I think you can maybe move forward a little bit faster when you have a referral, a recommendation, but that doesn’t always work either.

Amy Hoy: I find referrals, I mean, a person who refers someone often is a friend or someone who knows them from a user group, something like that. You have no idea how that person acts behind closed doors.

Alex Hillman: You have to actually base it on how they work. I have lots of friends and potentially even friends who are listening, so I’m not going to call you out by name. People that I adore, people whose work I admire, but I also know better than to work with. And not because they’re a bad worker and I’m a good worker, but because our work expectations are not the same. I think that is, we can paint it as black and white, as good and bad. All of this comes down to, if you are not working with the same expectations and you maybe come into things with the belief that the other person will be more like you, or that you can be more like them, that’s where things come apart.

Amy Hoy: I have literally complained to you repeatedly about people not doing simple things that I think are obvious and you’re like, “Amy”, it’s like I do them and I did them when I was like 19, working as a consultant. And you’ve told me, “Amy. You’re an outlier”. I’m like, damn it. I am an outlier. Assuming people are going to understand you or have your work ethic or be as devoted to the project as you are. Even if they say they are, basically you’re just dancing out on a limb and hoping it doesn’t break.

Alex Hillman: Right. It’s hopeful. It’s hopeful.

Amy Hoy: Yeah. It’s hopeful. I feel like when you feel hopeful about a person or a project, that’s a sign you should stop whatever it is you’re doing, because you’re about to make a mistake.

Alex Hillman: Yeah. Really take some time to find out , you know, it’s hard and potentially not even possible to have a conversation about how somebody acts when something went wrong, in the same way that you would have that conversation before you maybe get married. You have to spend time with people finding out who they really are before you enter into a term business relationship with them. I think that’s massively overlooked.

Amy Hoy: It’s so, so overlooked.

Alex Hillman: I’m curious, I think about this in terms of like a cultural context as well, where different parts of the world – and I see this through my coworking work – different parts of the world prioritize relationships and transactions differently. I think it’s a very North American/American point of view. I don’t care whether or not I trust you if the business deal is good enough, I’ll deal with the repercussions later, versus other cultures where the trust is so massively overvalued that people will walk away from great deal terms because of a single under – not even un, but under-trusted person has entered into the picture. I think a lot of Asian cultures.

Amy Hoy: I was going to say, we’ve probably listened to the same podcast about Japanese business deals or something!

Alex Hillman: I’ve read at length about it.

Amy Hoy: Maybe it wasn’t a podcast. Maybe it was just you talking to me, sometimes it’s hard to tell the difference.

Alex Hillman: So I think this all comes down to context and knowing who you’re dealing with, whether it’s a single individual, and understanding their background, their experience, and someone who is new to all of this has no context – which makes you even harder.

Amy Hoy: So I know it sounds like we’re totally hating on the whole situation. Okay, maybe me, not so much, Alex. Alex loves people. I don’t.

Alex Hillman: That’s part of why we work so well together.

Amy Hoy: I’m a wounded optimist, that’s why.

Alex Hillman: And I’m a cautious optimist. That is our difference. I mean, we have other differences.

Amy Hoy: We have other differences too! I’m not saying don’t hire people. I’m not saying don’t have business partners. I’m not saying don’t hire consultants or whatever, but you have to do it at a point where if it goes wrong, it won’t break you. You have to be the one in charge by starting a business, you’re the boss, the buck stops with you.

If you hire someone and they steal from you – that’s your fault. If you hire someone and they need your help to do their job, that’s also your fault, or rather your responsibility. You have to be the one to protect your interests and I feel like if you’ve only ever been an employee, you are not prepared to deal with the boss stuff, so put it off until you can do it from a position of strength. Don’t make yourself vulnerable for no reason. It’s not like romantic relationships where you have to be vulnerable to have one at all.

Alex Hillman: Yeah, I think that’s a great spot to wrap that up and I agree a hundred thousand percent that you being the boss, you taking responsibility and maybe that’s one of the hardest lessons in business, being in business for yourself is that you are responsible for everything. Like you don’t get to point the finger at the employer of the contract and say, it’s their fault. Even when it is, it comes back to you because you made that decision.

Amy Hoy: You made that decision, you trusted that person, you didn’t consult a lawyer or whatever it is. If you don’t take responsibility, you can’t be the boss. You’ve created a job for yourself that no one is in control of.

Alex Hillman: So next time we get together, we have yet another bullet point in your list of five things to talk about. Marketing. Everybody’s favorite, everybody loves, everybody dances every time he says, “let’s talk about marketing!”

No, and this is the expectation of how much marketing really goes into running a product business.

Amy Hoy: Yes. For example, the idea that if your product is good enough, it will sell itself – it’s surprisingly not true.

Alex Hillman: Until next time…

Amy Hoy: Until next time!