profileChris has been building web applications for over 16 years, successfully completing projects for business of every size, from Fortune 500s on down.

Day-to-day, he manages a custom web development consulting firm. He also authors a software industry blog and has been published in Software Development Magazine (now Dr. Dobbs).

Chris prides himself on having built a reputation as an expert in handling crisis projects and difficult clients.

What Your Favorite Motivation or Business Books?

1 – The Charisma Myth by Olivia Fox Cabane

2 – Looking Out For #1 by Robert Ringer

3 – Peopleware by Timothy Lister and Tom DeMarco

Can You List 3 to 5 Life Success or Leadership Principles?

1 – Ask lots of questions, and care about it answers.
2 – Follow the money.
3 – Be kind when you can afford to be, and hard-hearted when you must.

Have You Got Any Special Promotions or Offers At the Present Moment That Our Listeners?

The free “Conquering Client Conflict” e-mail course has now re-opened!

As freelancers we face a lot of challenges, even on a good day. But when it comes to our clients, these challenges – being slow-paid, chiseled, schedule-jumped or argued with – can be truly infuriating. But it doesn’t have to be that way.

Sign up for the free training at

To Find Out More About Chris

Cogeian Systems

Full Interview Transcript

Jonathan: Hi there, folks, this is WP-Tonic, episode #112. We’ve got a great guest here, folks. We’ve got Christopher Hawkins from Cogeian Systems and we’re going to be talking with Chris around a really interesting subject: how you deal with those difficult clients?

How are you doing, Chris?

Christoper: I’m doing good.

Jonathan: Thanks, Chris. And I’ve got my beloved and patient co-host John Locke. How are you doing, John?

John: I’m doing awesome.

Jonathan: He’s awesome today, folks. So Chris, you’ve got loads of experience in web development and design over the years. Can you give the audience a quick synopsis of your background and your experience?

Christoper: Sure. I started in the web business in the late 1990s doing Big Iron Fortune 500 HR apps for companies like Exxon-Mobil, The Gap, Goodyear — so on and so forth. Then I went out on my own. I started a consulting firm called Cogeian Systems back in 2003 and we’ve been banging out web apps and websites ever since.

Jonathan: Sounds great to me, folks. This guy’s got a lot of experience. You were doing a fantastic podcast [Chasing Product], but you’ve put that on the back burner for a while. Is that correct, isn’t it Chris?

Christoper: Yeah, you know, it’s not just back-burnered. It’s run its course.

Jonathan: I’m sure you’ll come back to it. It’s in the blood. When you would get in front of the mic, it’s hard to get off it, I can assure you.

So Chris, we’re going to be talking about — in whispers — how to deal with those difficult clients. I think all wars — all battles and wars are won before they are even fought, really. So is that the case with difficult clients? [They] will come up, won’t they?

Is it really your methodologies — your internal structures — that will help deal with these situations? I’m just surmising that. Please tell us. Let’s start off. Is the battle lost before it’s normally even begun? As they say?

Christopher: Sometimes. Sometimes as a consultant operating in this industry, I have sometimes heard people say things like, “There’s no such thing as a client from Hell.” But I’m here to assure you, clients from Hell do exist. But the tricky thing is that we often create them.

And the way we do that is by entering into a business relationship with someone who may or may not know how to interact with a consultant. Then we fail to set boundaries. We fail to set expectations. And then we become resentful when the client doesn’t behave in the way we wanted them to behave — even though we didn’t tell them we wanted them to.

Now that said, there’s the other kind of client. There are people out there that will enter into a relationship with you as a freelancer — and they’re transgressive. They’re predatory. They’re looking to take advantage [of you]. Those people have been with us since the beginning of time.

Once you’re in a relationship with someone like that, it’s really tough to get things back on track. Because they don’t want things to be on track. But the other kind of client — the one who comes by their difficulty honestly? They want the project to go smoothly. And so do we. So that gives us some common ground that we can work toward and work from.

Jonathan: I think that’s so well put, Chris. Actually I had a bit of communication with a client yesterday, and they were getting a little bit — let’s say — annoyed. But I considered most of the problems were being caused by them.

So maybe, they would come across this so sympathetic. Then they told me the truth. That they were actually getting a lot of — how shall I put it? They were getting a lot of grief from their supervisor. They were feeling a bit under pressure, to put it mildly.

So after that, everything came into place. We agreed, and now everything’s going sweet and they are entirely happy. I would say a lot of this gets down to understanding the client and direct and honest communication. What do you think, Chris?

Christopher: Sure, I agree it always boils down to the boundaries, and in order to create good boundaries, you’ve got to have good communication. We very often don’t tell clients what we want. And when I say “what we want”, I don’t just mean, like, “In my heart of hearts, I want a pony”.

Who cares. What I mean when I say “what we want” — is square dealing. We want things to be nice and explicit. We want the client to provide their end and hold up their end of the deal, as we provide services to hold up our end of the deal. But a lot of the time, we don’t tell them this.

And to be honest, a lot of the time we shouldn’t need to say things like, “Gee, could you please not call me at 6am on a Sunday.” But when the need arises — instead of resenting it, we need to speak up. When our boundaries are pushed back against at a certain point, we need to be professionals and just say no. “No” is a complete sentence.

There’s nothing wrong with telling a client, “No”. As a matter of fact, I’ll argue that there are a number of scenarios in which you do your project a whole lot of good by telling your client no.

Jonathan: Well, it is not encouraged in most things you read on the internet. You know, you read a lot [that says] “The customer is always right.” Don’t you, Chris?

Where do you think that comes from?

Christopher: Gosh. You know, I think that comes from pandering, to be perfectly frank. I think that comes from people trying to present a politically palatable face to their client. And you know, sometimes you’ve got to do that.

But the bottom line is, we get brought into a project to bring about some sort of an end product or some sort of result that wouldn’t happen on its own. We are brought in because of our expertise. If our expertise later gets questioned or undermined, we absolutely must say, “No — we need to do X, because Y.”

If we don’t have a Y to point to — if we can’t say “Because Y [will happen]” — well then, we’re just guessing. We’re not employing our expertise, anyway.

And that’s fine. Many times, we can and should try to use our clients as a resource. They’re the domain expert on their business. We’re the niche expert on the aspect of their business that we’re trying to improve — or fix, or streamline, or automate — or what have you.

So there definitely needs to be some collaboration. But when boundaries are being pushed — [such as] “I want you to work for free”, [we have to say] “No.” [If a client says] “I want you to be on call on weekends,” [we have to say] “No.” [If they say,] “I want you to cut the price in half,” [We must say] “No.” [Or if they say] “I want you to let my nephew be part of the development team.”

[We must say] “No.”

Jonathan: [laughs] Definitely no.

Christopher: I mean, we’ve got to make sure that the project gets done in a professional manner, and according to the best practices that we know how — according to the best practices that we’ve been brought in for.

So, sometimes we’ve got to say no.

There’s a catch, though. You want to hear about the catch?

Jonathan: Of course, Chris.

Christopher: There’s a catch in that when we tell a client, “No”, if it’s at all possible to do so, we have to kind of find the “Yes” that’s hiding in the “No.”

For example, [let’s say] we’ve contracted to build an app. It’s got certain set of features. The client wants a whole new feature, and they want it for free. [Our reply would be] “No — but yes, we can absolutely build that feature for you. Let’s talk about scope and budgeting. But no we’re not doing it for free.”

So there’s always some kind of a way where you can find a path to giving the client what it is they want, and what they need. But it doesn’t necessarily have to be at the expense of sacrificing a professional boundary.

Jonathan: Yeah, it kind of occurred to me [with someone] I was talking to recently. I had done a proposal and he’s got a friend that hosts the existing site. And [the hosting], it’s one of these — I’ve never heard of them. I don’t know what their setup is. Been there, done that. I’ve had my ass burnt [before in similar situations].

I said to him, “I’m quite happy to have a chat with him. But I’ll make it absolutely clear, if I’m doing this job for you, and I don’t think the hosting is good enough — we’re hosting with somebody else.”

Christopher: Right.

Jonathan: There will be no ifs, [ands or buts]. As soon as I feel that they are not capable of hosting the site proficiently, I will give you a list of hosting providers that I think are reasonable, and you can choose from those or somebody else. But I must have the last say their ability [to host the site]. And I said, “If that isn’t acceptable, well I’m afraid we can’t do business together.”

And he looked at me and he just accepted it.

Christopher: That’s beautiful. That’s kind of how it should go. You were brought in to provide your best expertise, and you did, and your client accepted it. [*claps*]

Jonathan: Well, he hasn’t given me a check yet. He probably went to every other web designer in Reno, Nevada — or whoever. But that’s his business isn’t it?

So before our live [stream], we had a bit of a chat, and you were going to give us [some insight]. I think that we all hate being placed in a stereotype, don’t we?

But we all do it ourselves. We are all a bit hypocritical. But in some ways, it is educational and helpful to give some scenarios about personality types. Based on your many years of experience, could you give us some kind of [client] persona types, and maybe different ways that you should treat them?

Christopher: Yeah absolutely. With pretty much all of these, setting and holding boundaries is key. A lot of us don’t have that skill. We’re not taught that skill, but we can get into that a bit more later.

The big one — and the one that I hear the most about — from both the freelancers that I mentor — from the people that share my articles on — from the people to reach out to me on Twitter — the biggest one here is either the Slow-Pay or the No-Pay.

Right? This is a very — see? You’re already laughing. This is a very special type of client, who for whatever reason, feels entitled to simply not pay you on time, if at all.

[They may say things like] “I didn’t like the work; I’m not going to pay you.”

[Or] “I like the work just fine, and I know we agreed to 30-day terms, but gosh, company policy says a hundred and twenty days.”

Things like that. “The check is in the mail.”

“My boss hasn’t approved your payment yet.”

Things like that. These often boil down to value issues. Again, sometimes you end up dealing with that transgressive person who went into it looking to take advantage of you. Those are a rarity, thank heaven for that. But very often, these are value issues. Very often, they’re not bowled over by the work — and to be fair, a lot of these projects aren’t really the kind where you can bowl somebody over.

“Oh look, another five-page brochure site.”

But we should always shoot for that. [Stellar work]. We should always shoot for doing the very best work we can. We should always shoot for absolutely satisfying the contract. We should always shoot for hitting our deadlines, and doing everything to the absolute best of our professional ability. And if we have done that, then we’ve done our part. Their part is to pay us.

So the No-Pay, the Slow-Pay? That’s the big one. Another one that I hear a lot of complaints about — and it’s almost the polar opposite of this — is the Radio Silence [client persona]. You’ve got this client, and it’s always an urgent project, right? It’s got to get done in three weeks, and they paid your deposit, and everything looks okay — until you need some feedback. Until you need approvals to move on to the next phase of the work, right? And then you hear nothing.

Jonathan: Crickets.

Christopher: You email them again, and you call them and leave a voicemail and one more time. Sometimes this is also a Slow-Pay scenario. But very often it just randomly happens in the middle of a project phase. And I get why it happens.

Very often, what might be our biggest client — our most important project — is just one of 25 things that this poor person at the client site is dealing with. So sometimes, the priority of our project falls down a little bit. But as professionals, it’s up to us to be an advocate for the project. As business owners, it’s up to us to be an advocate for our own business. So if it’s driving the project off track, it can’t stand, and we need to stay after it.

Then another one — this one is my personal favorite — is the Art Director.

I am not a designer, but I do employ designers. John, I believe does more a lot more design than I do. He’s probably smirking right now. The Art Director is that client where either they, or somebody in their department, or the fabled nephew wants to micromanage the design of the site. Everything from color choice, to layout, to font size.

What was that meme years and years ago — “Can you make the logo bigger?” There’s a reason those things are funny. It’s because they’re true. They happen.

We all know people who have had these things happen, and they’ve happened to me.

Generally speaking, although these clients are well-intentioned, and in some cases, they may have valuable things to contribute. But in some cases, the way that personality type is executed — the way it’s injected into the project — it just serves to muck up the works and make the project more difficult for everybody.

Jonathan: You know, I think you’ve upset John because he’s left the room, Chris. But once he’s recovered, I think he’ll come back.

Christopher: I think he’s shedding a tear about all the Art Director talk.

Jonathan: I think another one I’ve come across is death by committee.

Christopher: Oh, yes.

Jonathan: If you’ve come across it, would you like to talk about that?

Christopher: Yeah, there are always indecisive clients out there. I totally understand why it all comes down to risk. They hire us to build, let’s say an HR app, to manage their human resources operations. They hire us to build whatever kind of an app they want to sell to consumers, or to build a website or two to streamline their internal services. These things represent risk. They’re putting in a certain amount of money and time and effort, and in return, they’re looking to see some sort of a benefit.

This is frightening. It’s very frightening, and I think sometimes we forget that we’re sitting here at our desk. We’ve got our little pipeline of leads. We’re thinking, “Gosh, just sign the deal and send the check already and we’ll get to work. Let’s do this.”

Forgetting that, to these folks, if they roll the dice on us and we screw up, they get fired. Or their business craters. Or at the very least, they lose their investment. Now, if everything goes well — fantastic. Everybody’s eating lobster. So these clients will sometimes get bogged down in endless levels of management, and endless levels of approval, endless levels of maybe this — or maybe that. That’s very tough to do.

If you disconnected it from the process — if your point of contact is not the person who has ultimate authority over greenlighting the project — that can leave a freelancer in a really weak position. We just can’t exert a lot of influence over the process that way. That’s why I started using paid discovery projects, and discovery engagements at the beginning of the project.

It helps to get in the room with the actual stakeholders. It helps to hear their actual concerns. It helps to hear the things that they’re actually worried about, so that we can address them directly and be part of the process — rather than just being some disconnected entity on the other side of a phone that isn’t being picked up.

Jonathan: I think that’s great. Obviously, you’ve been in this business for a long time. Chris, can you quickly talk about one project you did quite a while ago when you were learning the ropes — [when you didn’t know business] to the extent that you know now — that on reflection, you made mistakes. Maybe something comes to mind, that on reflection you learned from it.

Christopher: Probably my first 20 projects as a consultant, I made some form of an error or another. Let me go down the list.

Letting somebody beat me down on my rates for fear of losing the work. Let’s see, comping work. [Where] we contract to do X amount of work, and I give them x times 2 — and the rest of it’s not for any kind of a charge. Which is a really weird thing [when you think about it]. Nobody would ever think of going to the grocery store and wait until all their items have been rung up, and then say “Oh wait, I want to add this head of lettuce — but I don’t want to pay for it.”


But for whatever reason, they don’t think much of asking us to.

Jonathan: You could do that, but you’d get a big boot up your backside wouldn’t you?

Christopher: They would say no! Because they have boundaries. They’re professionals.

Gosh — the Art Director thing. You know that thing about the nephew being part of the dev team? That actually happened to me, and I actually went along with it, to my eternal chagrin and my infinite embarrassment. That was bad news.

There’s another one. That was on me, though. That wasn’t the client.

I mean you name it, and I’ve made the mistake. I put up with the Radio Silent people. I put up with the No-Pay and the Slow-Pay. I put up with the Blackmailer. You know — “I’m not going to give you your payment for the first phase until you get started on the second phase.”

I mean, I’ve dealt with it all. It’s embarrassing, really. It’s embarrassing. Probably the first three years of my consulting career — an absolute embarrassment. I’m amazed that I managed to take home a single dime.

Jonathan: Actually, that is not unusual. That’s why I feel a lot of freelancers get out of freelancing after two to three years. Because that is not that untypical. Well that was great, folks.

We’re pitching a really dark and dismal [scene]. Very English isn’t it, folks? But when we come back from the break my co-host will be taking over the interview. Then I’m sure it will become sunshine, unicorns, and light. Not the dismal darkness that I’ve been discussing with a very cheerful Chris. I’m going to be back in a minute, folks.

We’re coming back, folks, and my beloved co-host John, who has been waiting patiently will take over. Go on then, John. Take over. Be light and unicornish.

John: Well, we’ll see. Chris, you mentioned the first three years you were consulting, you made all the mistakes. I think a lot of freelancers make those same mistakes. Is there a way for them to — is there a way for freelancers and consultants to avoid making those missteps early in their career? Or is it typical for them to just have to learn those things the hard way?

Christopher: I think both of those things are true. Actually, I think it’s extremely typical to have to learn those lessons the hard way. But I also think that it’s possible to avoid the worst of it as a first timer.

The big thing — and again I keep coming back to the boundaries and expectations — that’s all fine. But I can think of more than one occasion when I was just starting out, where it came down to: I have a project in front of me with a client whose behavior is already problematic before we even started.

I’ve set out expectations. They’re clearly not willing to meet them.

But if I don’t take this job, I don’t make my mortgage. It’s as simple as that.

I will never tell a freelancer that if it comes down to survival — just flat survival — [between] food on your plate and your own professional boundaries — I will never tell a freelance to choose their boundaries — if it’s truly a scenario like that.

The trick is figuring out when it is, and when it isn’t. I think when we’re starting out, we’re prone to fear. We’re in completely uncharted territory.

So we think that every deal could be the last deal. I think the first step is to understand that there’s always another deal. I know that sounds glib. I know that sounds glib, and somewhere there’s a freelancer who is struggling.

And they’re watching this, and they probably resent the hell out of me for saying that. But that is the truth of it. That’s a hard one truth [to accept]. Because there were many times when I found myself mired in the middle of a nightmare project, only to have another lead pop up. A lead who was happy, and had a budget, and was cooperative, and was really excited about working with me — and I couldn’t take it.

And that just killed me. So I think the first thing is to just realize whatever you’re in the middle of — this too shall pass. The sun will rise tomorrow and whatever you’re doing, if you got this job, you can probably get another one.

John: So do you think that the Universe tests you to see if you’re going to enforce those boundaries that you’re setting out to set with your prospects? Do you think that is maybe where people run into trouble? Is that they cave too easily [to client demands]?

Christopher: I don’t know if the Universe is testing us, but I know that human nature [is that way]. Human nature is testing us.

John: *laughs*

Christopher: If somebody thinks they can get more from you for the same amount of money — just by browbeating you a little bit — or maybe [with a] little bit of manipulative wording in an email — of course they’re going to do that!

It’s incumbent upon us to be adults, and to be professionals, and just operate the same way we would expect our auto mechanic or our doctor or attorney to operate. These are the parameters in which I do business.

The thing you’re asking for is outside those parameters — judgment call — am I willing to do it for a little extra money, or am I not? And if not, then am I willing to just not do business with this person. That’s a tough one. That’s a really tough one.

It took me probably 6 to 8 years of freelancing before I came to a place where I truly made peace with the idea that not every client was suited to me — and maybe I wasn’t suited to every client. My ego doesn’t like that idea. But it’s absolutely true.

So I had to decide what kind of a life I wanted to have. Not just what kind of a business do I want to have? The kind of life where people treat me like I’m at their beck and call for low wages and they only pay if they feel like it? If they’re in the mood? On every other alternating Tuesday of the month?

And you know, just all the other nightmare scenarios you find yourself in.

The answer was No. So I simply began saying No when people would step over whatever boundaries I had set in the first place. I would educate them, and I would elucidate — “Look. This is the terms of the agreement that we agree to work in. We need to do it this way, because doing it this way makes for a better project.”

Then ultimately, when people weren’t willing to do that, I had to become willing to cut them loose, and that was tough. It took a lot of work. But I definitely think that if I were starting out now, with the wealth of freelancer tools that are out there — I’d probably be able to get savvy to this a lot faster — a lot faster.

John: One last question before we go into the end here. Something I want to get back with what you said before. When you said that a lot of we give up a lot of power when we try and pander, and we try to please people, trying to get in their good graces.

Give me your thoughts on this — I think a lot of freelancers are used to being employees of other places. And I think a lot of that “the customer’s always right” [mentality] and trying to please people to the point of harming ourselves comes from that [mindset]. I think making the transition from going from being an employee to a business owner is kind of a tangential shift in mindset.

What are your thoughts on that?

Christopher: I think you hit it on the head. We’re very accustomed to [that thought process].

For example, I mentioned earlier that I worked for a big HR software company. We have a big Fortune 500 [as a client]. My job was to sit at my desk, and my boss would shovel work in my inbox, and I would execute on that work, and I would wait for praise.

“Gee, boss. Did I do a good job?” I would wait for the accolades to come in from the client. Then some more work would be shoveled into my inbox. And I would dutifully go about shoveling it back out.

This does not work as a consultant. If you want to be a contractor — fine. Because that’s effectively the same thing. The only thing that changes is your tax form, your W-2 or 1099.

If you want to be a freelancer, the key word here is “free”. A freelancer has agency — not an agency — but agency as an individual. A consultant has agency as an individual.

Our clients want us to stand tall and behave like professionals, because that benefits their projects. They get a better return on investment when we do that.

None of the things that I’ve advocated so far — just in case anybody construed in this way — should indicate that we need to be belligerent or combative with our client. We just need to be firm about what it is we’re here to do, and the terms under which were here to do it. Doing so is going to make things much better for everybody.

So yeah John, absolutely. Bringing an employee mindset into the freelancing and consulting world — it’s really going to limit you. In a lot of cases, when somebody ends up washing out of that world after a year or two, it’s because they never were able to let go of that mindset. So effectively, they were trying to function as an employee doing consulting and freelancing work. It just doesn’t work.

John: Definitely. So, we like to close out these segments by asking about some of your favorite motivational or business books.

You listed The Charisma Myth, Looking Out For Number One, and Peopleware. Tell us a little bit about each of those.

Christopher: Okay, The Charisma Myth is — I’m not sure how new the book is, but it’s new to me. It’s by Olivia Fox Cabane. Apologies if I’m not pronouncing that right, Olivia. The title sounds very glib. The Charisma Myth.

Anything having to do with charisma, that sounds like some smarmy sales stuff. But the book is really interesting. It’s basically a way to break down charisma as a set of psychological and mental hygiene skills.

It’s a mindset. It’s a perspective. It’s an attitude backed up by behaviors. It’s not just some magical pheromonal, born-with-it thing that oozes out of you. It’s actually a set of habits.

As a dyed-in-the-wool geek, I found it really interesting to think, “Oh well, wait a minute. So you mean I can actually hack my psychology for greater charisma — to be more influential? Or to be more commanding when I’m dealing with clients to engender more trust — when I’m trying to close the deal? That sounds fantastic.”

This sounds so goofy, I almost hesitate to say it. That book is almost life-changing. It’s almost life changing. If you’ve ever suffered with this feeling of disconnectedness or isolation — if you’ve ever suffered from the sense that you’re not able to impart a sense of power, a sense of trust, a sense of authority, or competence with clients —with your friends —with whoever — read this book.

[There are] goofy little habits and mindset shifts and stuff, and it’s just fantastic. It’s not magic, it’s just work. It’s a skill just like development. Definitely check it out.

What’s the second one?

John: Looking Out For Number One.

Christopher: Thank you, my diabetes medication messes with my memory a bit, so bear with me. Looking Out For Number One is a very old book by Robert Ringer. I believe it was originally written in the late 1970s. And the title — God, it just sounds so eighties doesn’t it? Looking Out For Number One. And in some ways it is very, “Go Go” — very “me me.”

But if you boil the book away, again, it’s a mental game book. It comes down to mental hygiene. It comes down to the idea of accepting that I am the most important person in my life, and I need to treat myself as though I’m important. Because that acts as a signaling factor, which then gets other people to treat me as though I am the most important person in my life. I’m a person worthy of respect.

Boundaries with clients, boundaries with friends — anything that’s going on in your life. Looking Out For Number One is just kind of a mindset that keeps you focused on the fact that “this is my life”. This is the only life I get.

So if I want it to go the way that I want it to go, I need to behave in a certain way, that’s going to help me interact with people in such a way that they’ll go along with that. You know, we all have to make deals on a daily basis with each other to make our way through life.

Fantastic book. It’s maybe a little bit on the hard-nosed side for some people, but I dig that. So what are you going to do? Then the last one is Peopleware.

Peopleware — I’m sure you’ve read Peopleware, right?

John: I have not.

Christopher: Oh you’re killing me, John. You’re killing me.

Okay, Peopleware is kind of the — I hate to use the word seminal — but it’s just THE book if you want to understand how developers work best. The kind of conditions under which they work best, the way they communicate best, the way to run a project among software developers best.

Peopleware is the book that some number of years ago Joe Sapolsky famously used to back up his case for building individual offices for every single developer at Fog Creek. [This was] at a time when an open-plan framework was kind of [popular] — that kind of bull pen model. That unfortunately still persists to this day. It delves into developer psychology and productivity.

Anybody who’s working in any kind of a capacity where they write any kind of code [should read this]. If you’re a DBA, if you’re one of those weirdos that use Angular, if you’re doing you know WP dev or Big Iron UNIX — you know, Oracle systems — read this book. If you haven’t, it’s one of those ones that’s almost foundational in a lot of things that we do these days. But it’s kind of been lost to time a little bit.

Really valuable stuff.

John: I’ll check it out.

Christopher: Oh yeah.

John: So lastly, your three success and leadership principles. You listed “ask lots of questions and care about answers”, “Follow the money” and “Be kind when you can afford to be, and hard-hearted when you must.”

Tell me a little bit about asking a lot of questions.

Christopher: Asking a lot of questions — especially in business — but even just making friends with people — getting along with human beings in life in general, is a really important skill for getting by. And in business, asking a lot of questions gives you two things.

Number one, it gives you a sense of connectedness, and it gives you a frame of reference. For example, in my early example, when I was an employee, they would shovel the work in my inbox, I would build my widget, I set my widget on the conveyor belt, and then I watch it go out of sight.

Well as a consultant, it suddenly became incumbent upon me to say, “Wait, where did the raw materials from this widget come from? What kind of contractual terms were negotiated for those raw materials? Why is this person constructing the widget? Where does the widget go when it goes down the conveyor belt? To whom does it gets sold? What is it used for?”

So the idea behind asking lots of questions is just to have a more expansive worldview. If you want to boil that down to micro, it’s to have a more expansive project view. It’s to have a more expansive view of how our clients do business — to understand why they make money, and how and where it comes from. And what that money is in aid of, and how their operations work.

Understanding the relationship between all the different pieces that go into making — not just a development project — but the client of a development project — what goes into making a business model — the more we know about these things —and I know this is a little unnatural for a developer — but the more we know about these things, absolutely the more effectively we can behave as freelancers, consultants, and people who provide value to the entire business process.

The second one was?

John: “Follow the money”.

Christopher: Right.

That’s just good sense, man. There’s a reason why there are so many people out there selling marketing information. That’s got a direct correlation to someone’s ability to make money.

I think it was Rob Walling — don’t quote me on this — but I once heard somebody kind of classified things as, “There are vitamin products. There are aspirin products. There are steroid products.” I think the same thing applies to services.

If I’m just selling websites, what is that in aid of? Well, I’m selling websites that specialize in lead generation. Oh, that’s a little more interesting. I sell websites that are optimized for, converting opt-ins into sales. That’s even more interesting. I’m selling a subscription service that does X.

Whatever we’re doing, we need to find a way to tie it back to revenue. Even if you’re doing something boring like a maintenance program — even if you’re doing something like the aforementioned HR application for keeping track of OSHA violations in the workplace — somehow, somewhere, our projects have a relationship to money as an outlay — as a savings, as a cost, as a revenue driver — something.

If we can’t figure out how our projects relate to the flow of money within a client organization, we’re going to have a really tough time pitching budgets. We will have a really hard time closing deals. We’re going to have a really hard time upselling additional work when it becomes available.

So being aware of that — seeing where the money flows from, and where it flows to, and how it interacts with our project is really, really vital.

Then the last one, about being kind when you can afford to be, and being hard when you must — that all comes back down to the boundaries. I like my clients. I have great clients. Ask me why — ask me why.

John: Why do you have great clients?

Christopher: Because I fired all the wrong ones!

I like the people that I work with on a daily basis. I really do. I’m happy to be kind to them. I’m happy to help them out. I do comp an hour here and there when I can, or help somebody out with something. I’ll gladly take a look at something if it’s acting weird — no charge. It’s the little things. You’ve got to be human with people.

This is a business of human beings, human interactions, and human relationships. But when someone’s being transgressive, or when somebody stepping over lines — when somebody’s pushing boundaries — that’s when it’s time to be hard-hearted and just say, “No, that is not okay. It’s not okay, because these are the parameters in which we’re doing business.”

It’s really tough sometimes to find the path between the two. It’s a narrow path, and it’s not lit very rightly. It’s difficult to find, and sometimes we stumble around in the dark. We bang our shins up until we find that balance of understanding. “Where I can afford to be kind? Where I can afford to be human? And [then] where I have to drop the hammer and say “No, that’s not acceptable.”

It’s very difficult. But if it’s a skill that you can master, it’s absolutely worth its weight in gold.

Jonathan: I think that has been fantastic, Chris.

I’ve actually got one quick ending question. I think the second half was really fascinating. But what do you think is the importance of mentorship? Especially for a developer becoming a freelancer for the first time? Do you think finding somebody that can mentor them is going to make a big difference?

Christopher: You know, I do. I really do. Back in the early 2000s, my mentors were people that I just read their blogs. There really wasn’t a whole lot of that going on [back then]. Nowadays — ooh — now you’re really talking. We’ve got all sorts of membership sites. We’ve got email courses, we’ve got blogs. We’ve got — you name it. I mean, hell, you can probably learn something useful just from following all the memes we have these days. People are hungry for this kind of stuff.

If I were a freelancer starting out, I would absolutely be drinking from the firehose, in terms of pulling all this great freelancing info off the internet.

There’s an important way to look at it.

A long time ago in another life, I studied martial arts, and there’s this whole thing about the black belt never washes his belt.

Because over the time of training and being just kind of worn down, the belt eventually turns white again. Signifying the whole closed loop between becoming a master, and then returning to being a student. The idea being is constantly teachable.

I think that’s really important for a new freelancer to keep, especially since there’s so much to learn, and there are so many ways to learn.

I mentor some freelancers. I’m pretty sure John mentors some freelancers. I know that we’ve exchanged tips from time to time. He’s mentored me on stuff. I’ve mentored him on stuff.

John: Yup.

Christopher: I’ve got a couple of hundred students who have signed up for my Conquering Client Conflict email course, and I’ve had a couple of them email me and say, “Hey Chris, what about this?” Well, wait a minute, I thought you were learning from me, and yet you just emailed me and dropped a great tip on me.

You never know where you’re going to find a piece of gold that you can plug into your business and make hay with it.

So yeah, absolutely. It’s a huge thing. If somebody can get a one-on-one relationship with somebody slightly ahead of them, great. If you can join a mastermind, fine. If you can’t do any of that, read. We’re geeks. We love to read. I know, we do read. It’s really that simple, sometimes. But yes, it’s absolutely important to get some kind of mentoring from somewhere.

Jonathan: That’s fantastic, Chris. We’re going to end the show now. I think it’s been fascinating, and thank you so much for coming on, Chris.

So how can people [find you]? What’s the best way for people to contact you? And are there any kind of products that you would like to plug and tell our audience about?

Christopher: Well, your best bet, if you just want to keep up with me and what I’m doing on a daily basis, you can find me on Twitter, @chris_hawk.

If you want to follow my blog, I send out articles regularly to my mailing list, along with other tidbits,like appearances on fine podcasts like this. You can find me at

Then finally, if for whatever reason you’re a freelancer, and you find yourself dealing with the kind of difficult clients we’ve been talking about in this episode, and you’re not quite sure how to deal with them — you can join my free email course called Conquering Client Conflict. It’s a ten-part course. I’ll send you one email for 10 days, and I’ll probably hit you up at the end to buy my book.

Feel free to pass on it, if you want to, but for God’s sake, sign up for the course. It’s at I guarantee you won’t regret signing up.

Jonathan: I think I’m going to be signing up.

John, how can people get a hold of you, and learn more about John Locke?

John: Well first off, I want to say to you [listeners], definitely take that email course that Christopher is putting out there. It will teach you a lot. But if you want to get a hold of me, you can find me at my website, which is, and if you want to follow my exploits on Twitter, you can follow me at @Lockedown_.

Jonathan, how do the fine people get a hold of you?

Jonathan: Fundamentally, the quickest way is either on Twitter — and my Twitter handle is @JonathanDenwood.

Professionally, I’m on LinkedIn. If you send me a LinkedIn message, I will reply. Or you can email me at . And do remember, folks, we are a WordPress maintenance service.

We do all the work, so you can concentrate on building your online business. There’s only so many balls that you can juggle effectively, so we become your web maintenance, design, or development people, that are always there to help you.

So Chris, thank you so much. I think it’s been a great show, and we’ll be doing our live panel tomorrow.

On Saturday, we’ve got a fantastic panel, and we’re going to be talking about how to write effective proposals that will get the work and the projects that you really are looking for. It kind of fits into what we’ll be discussing today, folks. We do that each Saturday on at 10am Pacific Standard Time.

So you can join us, ask us questions — we help people in the second hour. We do that every Saturday. So please join us, and we will see you next time on WP-Tonic.

All: Bye.

112 WP Tonic: How Best To Deal With Difficult Client Situations! was last modified: by