Can Sales And Delivery Teams Get Along?

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Galen Low: So you're walking the office halls with a few of your PM colleagues. Blake and Tas are shooting their mouths off about an impossible scope that the business development team sold through.

Suddenly the Business Development team rounds the corner ahead of you and everyone stops in their tracks and falls silent.

You overhear someone murmur, "Hey, there's that PM who shut down my AR idea on the telecom pitch."

There's a brief stand-off and exchange of glares. It's the Jets and the Sharks, the Montagues and the Capulets. The tension is palpable. 

It's only broken when you say, "Fuggedaboutit, they ain't worth it." And everyone walks away unscathed.

Okay, maybe that's a bit dramatic, but in many organizations there's still this misconception that the tension between the folks selling the work and the folks delivering the work needs to be adversarial instead of collaborative. 

If you've ever found yourself wondering whether it's possible to have a healthier tension between your business development team and your project managers, keep listening. We're gonna be giving you the tools you need to start building the bridges that help your organization grow.

Hey folks, thanks for tuning in. My name is Galen Low with the Digital Project Manager. We are a community of digital professionals on a mission to help each other get skilled, get confident, and get connected so that we can amplify the value of project management in a digital world. If you want to hear more about that, head over to thedigitalprojectmanager.com.

Okay. Today, we are talking about the tension between business development teams and project delivery teams, and how to make that a healthy tension that pushes your organization forward instead of creating drag. 

With me today is Nick Wilkinson, a long-time project manager and account manager who has worked on everything from native apps to mixed reality experiences—and who has now moved into a full-blown business development role with Steamclock.

Hello Nick!

Nick Wilkinson: Hi Galen! Thanks very much for having me here. 

Galen Low: Thanks for being on the show. I'm excited to dig into this. This is, for regular listeners, they will know that the crossover between project management and business development is exactly where my heart lies. You cut me, I bleed project management and business development.

So I'm really excited to dive into this today, a really important topic. But before we get into it, I thought maybe you could tell our listeners a bit about your background and kind of how you found your way into your current role. 

Nick Wilkinson: Yeah, absolutely. So I've been working as a project manager for about 20 years.

My background's in engineering. I studied mechanical and mining engineering at UBC. And then I found myself having a bunch of jobs where I thought I was doing one thing, but really I was doing project management. So that started with when I was working as an engineer, really I was a project manager. And then I went from manufacturing to logistics.

So I was very lucky to find myself in the position of working as a contractor on a projects related to NASA, the Canadian Space Program. And that was my first taste of like marshaling large groups of people towards a common goal over a long period of time. So I really feel like I cut my teeth as a PM just in general there, even though it wasn't really related to like the digital side of things.

And from there I worked, doing some consulting and then eventually made my way to actually working as a PM at a software development shop. And, again, as years went on, I started being able to build a team around project managers. And throughout all of that, there was always this really heavy business or account management component to it that was kind of weaving in and out of my day to day.

So whether that's working with a client to figure out like a phase two of a project or being a part of the original pitch proposal, or, you know, in the case of that other project, you know, working with the government, on a, you know RFPs and things like that, there's always kind of a sales component. So it wasn't just about the delivery of the value, but it was like figuring out, well, what is this value in the first place?

And then that is what lined up for me with Steamclock. I was very lucky to kind of be at a point in my career where I was thinking, you know, project management is great, but I'd like to kind of stretch myself in different ways and I have all of this experience working with clients to get them to where they want to go.

And at that time, Steamclock, which focuses on native mobile application development, predominantly. It's a company also I've had my eye on for years. When I announced my new role on LinkedIn I kind of admitted that Steamclock is, was my my secret crush for a long time. And it's absolutely true.

Just they've been doing really high quality work for such a long time, and there, there was just never like an entry point for me there. Until recently when they had this role open for a client partnerships manager. So I thought, well, I think this is the right move to kind of take what I've learned as a PM and then focus now on business development side of things.

And also gave me a chance to put into practice the things that I have been kind of shooting my mouth, mouth off about as a PM too, to the business development folks I have been working with, you know, over the course of my career. So, yeah I'm really excited about what's to come and also about this conversation here.

It's a really fascinating space. 

Galen Low: I love that progression. I love the progression of coming from a world where you were doing project management without, you know, formally being a project manager. You're like, Hey, maybe I should do this a little bit more formally. Got into a PM role, realized you were doing account management and business development kind of informally. And said, Hey, and then it ties back into something we talked about on an earlier episode, which was just that whole like finding a company that's gonna help you get to where you get to that you believe in. And I think that's amazing, so congratulations. 

And I am definitely going to exploit your perspective right now when you're just kind of at that crossover point between, like you said, being that project manager who's "Hey, sales team, this is what y'all have to do", to being the sales team now going, "Okay, here's what we need to do if we wanna make this thing something that can be delivered."

Nick Wilkinson: Yeah, Absolutely. 

Galen Low: Which, I mean, that's a really good segue into like, what is that tension? And actually, maybe the bigger question, why is there tension between business development teams and the sales teams and the account management teams, and then project managers?

Nick Wilkinson: Sure. So this is gonna be a wild overgeneralization, but the way I think about it is that on the PM side, you're off, like your default position is kind of figuring out creative ways to say "No". Like you're never, of course gonna just come out and say no to a client. We can't do that. Like you find ways around that, where you're still working towards a win-win.

But that's kind of, at least in my experience, has been kind of like the baseline is like, how do we get something done within the constraints of reality? And often that involves having to say, "Well, we can't do that, but we can do this thing."

Whereas on the business development side, at least from what I've seen, and again, in my experience, the default has been finding creative ways to say, "Yes, we can do whatever you want." Right? We're gonna promise you the moon, and absolutely we can deliver that. 

And I think, I mean, those are very extreme ends of that spectrum. But I think that's what the source of the tension is often in business development, you are not necessarily a part of the day to day of getting the work done.

You don't know what that lived experience is like of having distress through, you know, the daily standups and things aren't necessarily going right. And, you know, there's something that, know, we really made some assumptions as the development team and it turns out they're not correct.

And now we have to, you know, redo some work and just what that feels like, right? The PM will feel that acutely because they're with the execution team every step of the way. And I guess I should also mention, like from my experience, it's really coming from a point of view of services delivery, right?

So this isn't necessarily, you know, a product manager kind of perspective in a product company or selling, you know, licenses to a SaaS platform or something. It's really when you're delivering creative services or development services. So I think that's kind of the core, for me anyways, of that tension.

And the trick is to try to like reconcile that difference. Like how as a business development person do you develop the empathy for the team and show that you've got some skin in the game there and that what happens to the project is also happening to you and you're all in this together.

But then also on the PM side, realizing that, you know, this is a business and the point is in part, like not just to be really satisfied with the work that you're doing. But also, you know, you need to make money to stay in business. So reconciling that I think is a big part of this. 

Galen Low: I really look at framing because it also frames that this is a necessary tension. You know what I mean? Like, like you said, creative ways to say "yes" and creative ways to say "no". This sort of like fulcrum between, you know, being very bias guy, blue sky inspirational to, okay, well how are we actually going to execute this and let's make sure it's as realistic as possible and not make too many promises that, you know, we can't deliver on. 

But at the same time, like that is actually what makes it work is that you have these two different perspectives coming together to creatively say "yes" and creatively say "no" to find something that is actually business viable. 

Nick Wilkinson: Absolutely. I think that's a really great framing and it's sort of like this tug of war that is not supposed to end, right?

No one is supposed to win. You're supposed to basically be in this equilibrium, which is, sounds very exhausting and it, you know, it is. But that's really how you can pull things forward, right? Because on the one side you've got people saying "yes" to things that or maybe just right on the edge, or maybe for strategic reasons, it's important to, to move in that direction.

And on the execution side, you've got people saying no, because like, you know, this is the reality of the situation and here's what's possible and what's not possible. So it's a very exciting place to be, for sure. 

Galen Low: And I mean, when you were kind of both, when you're a project manager who was doing some account stuff, how did you find that balance?

Because that's a tug of war with yourself a little bit. I bet you found yourself saying, you know, creatively saying "yes", more than you were saying "no", which maybe led you down this path. 

Nick Wilkinson: Yeah. It was an interesting place to be because, I guess while it wasn't an account management role, it was sort of like the, like it was on easy mode. Because it was like, say for the continuation of a project that we knew we wanted anyways, right?

So the client's already been vetted and qualified. We know we've got a great relationship with them. How do we keep this train going? So that the internal tension there is a lot different than when it's a brand new lead. And I, I had also been in that situation before several times.

But there, it's clear that it's very easy to get swept away by the thrill of the sale, right? Because it, it's exciting and that's how you're defining success is like, well, I'm a salesperson. If I sell things, then I'm successful. But that's what I'm finding now about with this new role and also with the perspective of having been a PM is like the goal isn't necessarily a sale, the goal is the fit.

Like how do I make sure that the strength of the team that I'm working with is a really good match for the client and their particular ask? If it's not a fit, then this is probably not something that we should be pursuing. Like even if you know you're capable of convincing a client like, Yeah, this is gonna be awesome, like go with us, you know, this is gonna be the best thing ever.

Like, that's not gonna do anybody any favors cuz now you're hurting your team and also you're in a way, kind of hurting the client. So again, that the goal is that balance, like how do we know that we are the right fit for you and what you need? And the answer might not always be that we are a fit.

Right? And I think that's a way to help like dampen some of that inner turmoil. And especially the excitement is coming at it from that perspective of like, is this right or not? 

Galen Low: And I think that's like really apt. And I think a lot of folks who, you know, haven't been in business development roles, not everybody, but some folks, right?

In terms of sweeping generalizations, I would say that a lot of folks will be like, well, they get swept up in the thrill of the sale. That's how they're measured. They're measured by selling things and they really don't have to think about anything else. 

But to now that I've caught you at this moment where you're kind of crossing over, and you have a background in project management and delivery and actually, you know, seeing all these things through, like what has been your biggest shift in perspective and also like what stays the same? 

Nick Wilkinson: I think what stays the same, just starting there is that idea of protecting the team. I found that when I was a PM I was always very protective of the team and making sure that the environment was as conducive as possible to making sure the team could do their best work on whatever the project was.

So that sense of protectionism is still there. It's just coming at the process from a different angle. So now it's protecting in terms of like, who, as the gatekeeper, who do I let through? Who is gonna be a good fit? Who do I know we're gonna do a really great job for? And who do I know is, you know, not gonna be the best fit and is gonna end up in hurting the team in some way?

 So that, that's largely stayed the same. The difference now I think is whereas before I was able to kind of, you know, shoot my mouth off from the perspective of PM saying "no" to all these things, knowing that I was in this tug of war. Now realizing that I'm on the other side of that tug of war, it's like, yeah, your nose you know, point taken, but also we need to stay in business.

And how do we find that balance of projects that are maybe not always the thing that's gonna keep the development team at like maximum thrill, right? But also like is keeping a, you know you know, delivering satisfying work that people can be really proud of. That also helps to, you know, keep the business going.

So, yeah it's a different set of responsibilities and a different kind of mindset on the whole situation, for sure. 

Galen Low: It's actually really interesting, like that sort of guardianship and that gatekeeper mode, right? Like in a way you kind of, you know, as a project manager you are that gatekeeper of the, you know, all the changes or all that scope creep and you know, defending against that.

But actually now you're kind of out front. But what's interesting, and I think that some of our listeners might, you know, I hope they find that enlightening a little bit to be like, Oh yeah, like it's not just, so to say of closing it, like you're helping the business grow also by sometimes figuring out what's not the right fit. And guarding the team and protecting the team from having to do that project that's like, Hey, we got this $3 million deal.

It's impossible to deliver, but like good luck. You know, like it's not necessarily the best thing for the business. 

Nick Wilkinson: I've had some conversations recently around the incentives that salespeople often have. And I feel like in a situation like the one that I'm in where you're delivering on like creative or development services, like having some sort of financial incentive for a salesperson is not always the right move.

I mean, again, if you're selling, you know, seat licenses for some SaaS platform, sure, like that makes sense cuz you're looking for volume. But otherwise, like when you're in a situation like where I am, I feel like if I was incentivized to make sales, I'm kind of being incentivized to in some ways hurt the team. And that doesn't really sit right with me.

I'd rather, I mean another maybe, well I'm sure would be controversial opinion, and this is more of a thought experiment than something I think would work in practice. But like, it'd be interesting to incentivize turning work away, right? 

Like if you were actually incentivized to like say "no" to clients, I think that's an interesting way to think about that gatekeeper role is, the better you like, because then you're sharpening those skills on drilling down into, you know, what does this lead really need, and are we really the right group to fulfill that? Cuz if we're not ,well then, no. And then there would be some sort of incentive for getting good at that.

So, I mean, in practice obviously that's gonna have all kinds of challenges, right? You need to say in business, you can't just be saying "no" to everybody. But interesting to think about anyways, just getting good at the "no" part. 

Galen Low: No, absolutely. And I've seen businesses struggle with that. I've seen folks who went from a model where they're incentivizing the sale to incentivizing three months of retention to incentivizing successful delivery.

But then it gets beyond what that individual controls. But I do like that notion, the thing that I had cranking my head is like, sometimes as a project manager, but also anyone who deals with risk, you can bring that risk management into business development. And that's actually, you know, the reward is not introducing more risk than is already present.

And that could be over promising, right? That creates risk. Telling the client that you can do something that you can't, that introduces risk, that's bad for the business. There is a monetary value there in terms of like client walking away or going way over budget. It's an interesting model, you know, like, I think it's worth digging into, not just, I said no 16 times this week, but I reduced risk to the business because I said no to these 16 people this week.

That's a really, that's an interesting perspective. And I think a good tie in because I don't know, us project managers, we love risk management, right? Who are like, if this thing happens, then we're gonna be in the hole, but we can mitigate this risk by doing this or we can transfer this risk. I think that's a really interesting mindset.

And I think the other thing, not to dwell on it too long, but I also, I keep thinking about what you said about the tug of war game. The tug of war game that never ends isn't supposed to end. So you actually don't want to, even if you have the opportunity to, you don't wanna drag the other team over the line.

Because that will actually be the thing that, that makes it break. You have to find that balance. And I'm extrapolating a bit here, but one of the things I heard you say is, You'll look for those interesting projects that the team is gonna like to do. But you're also looking to keep the lights on.

So you're playing this tug of war with yourself as well to make sure that you are winning work that is enjoyable and that will help your team grow, but not by sacrificing, just that business sustainability or just that business health. 

Nick Wilkinson: That's exactly it. And I think a big way to help work towards that is by really getting to know your team, like who you're working with and what they're interested in and what they're not interested in. And folding that into your day to day in terms of when you're vetting and qualifying new leads. 

I've worked in environments in the past where like the sales function is kind of siloed from everybody who's responsible from, like there's that division line in the tug of war, right? But the more like exemplify how you're actually a part of the team. Like sure there's that tug of war, but you're actually still on the same team and that, that tug of war is really just a game to help make each other better.

The more you can, you know, stay with those projects all the way through to the end and be there, the, be like you know riding alongside the PM or producer on those projects and helping them with their struggles. And then to the extent that you can helping the team that's responsible for execution, like the developers and designers in QA and so forth.

The more you have an opportunity to build trust, right? And they know that when you're going out and trying to land new work, you're not just trying to sell at all costs. They know that you've got their back, right? So that, that's a big part of it is understanding who you're working with and how they work, what their interests are. And, yeah, it can go a long ways to making that better. 

Galen Low: Let's pop the hood on that, cause I like that empathetic angle and you know, I agree that, you know, being in there with the team delivering would be the best way to sort of build that trust to understand what you're selling, but not always possible, right?

You can't spend 40 hours there and 40 hours doing your other job. But just for the folks who are selling through that work, right? Account teams, business development folks, sales teams, customer success to a certain extent. Like what is that core that these teams need to know about project management and how the product is actually made in order for them to sort of start having that empathy and be able to bring that into the role that they play?

Nick Wilkinson: I think a lot of it starts with understanding what everybody does and how they'll work together. You don't need to be, like especially in a software development context, you don't need to be like a professional developer yourself to understand those key points. But just understanding, like from the perspective of the PM, like what do you do?

Like, what's your job, right? If you don't have any PM experience. And learning about, you know, the phases of, you know, how do you onboard a client from the PM perspective, and how are you onboarding the team and what does the phasing of the project look like? Like, who starts getting involved and when do they leave? And why do they leave? 

And how do we ensure that what we're putting out there is a quality result, right? That the client's gonna be happy with. Like what are our checks and balances there? Like, really understanding process, and then finding out not just from the PM but doing that with everybody.

So speaking with, you know, the engineering team, like, why, you what are the things that, you know, keep you up at night about this project or projects in general? What are the things you're always looking for? And understanding also how, aside from the personalities and the skills fit together, but the, also the technologies at a high level.

How does this work together? Like what do I need to know about servers and like why is it important that, you know, APIs are documented and like, what is an API and like, who needs to know what this is and how does that work? Like, how is it different between say, a web and mobile and are there any concerns that maybe one has that the other doesn't?

Just the day to day doing business stuff I think is really important to understand that. Cuz the more you understand it, the more you have an opportunity, I think to build trust with your team because they know that, you know, this person taking active interest in what I do and that, that's always cool. Right?

But also you can speak more authoritatively with clients when they ask technical questions, cuz you'll understand things at a high level. You know, you still might not know the nitty gritty of whatever, but you have a team of experts you can ask. So that's okay, but at least you can speak to, you know, a certain level to help make clients feel comfortable that like, yeah, this team knows what they're talking about and they know what they're doing and they've been doing this a long time.

And it's, there, there's no downside to learning and finding out about people and how they work and what they're doing. 

Galen Low: One thing I like about that is that, you had mentioned right, in our tug of war analogy, there's this line and it represents a silo. Actually, what's really interesting about it is kind of what you framed in, you know, truly the core, especially if you're working with similar teams or maybe even the same team every time.

Just, even just getting yourself onboarded, right? It's almost like if you were new to the team, what would they walk you through? They'd be like, Oh, who in the zoo. Here's our process. You know, here's the technology stack that we like to use. And it's almost that same kit. It's the same conversation.

But it's just breaking down those walls that have siloed the business development team or the account team from the project management team and the delivery folks. And I just think that, yeah, like all those things, what I liked about it is not just, Oh, please tell me everything about what you do. But like, what are some of the things we do and why?

And like how at a high level is the sausage made, so that I can kind of take that with me into a conversation with a client?

Nick Wilkinson: And I think it's also, important to reflect that back to the team as well, so that the team understands what exactly it is that you're selling. Because that can happen over time as well, where a sales team can get all kinds of really fun, fancy, new ideas about like, Hey, let's position things this way, and over time there's this drift that happens between what's being sold and what is actually what can be delivered, or the way in which it's delivered. 

And so it's important, you know, just to have checked once every once in a while saying, Hey, like, you know, when you have some time, I wanna show you my pitch deck cuz this is what I'm presenting to clients or leads, like, how does this sit with you? Right? Should I change any of this? This, is this accurate or is any of this like super uncomfortable and I should not be saying these things? Like, it's an iterative process that just, it's ongoing. It never really ends. 

Galen Low: I really like that, I'm gonna pitch you. You, you tell me what's wrong with it.

And like when I think back, like I have informally done that in the past, but I actually really like that as a process to be like, here's what the pitch is. You know, tell me what's right or wrong about it before put it in front of a potential client or a client. I love that. One of the things that you mentioned was, you know, getting smart enough about a thing.

But also I've seen that slippery slope of like, okay, well when do you find yourself, either trying to know too much as like an account person or as a business development person? And, could that lead to a position where you're not looping in the right experts because you're like, I got this. I know, I know APIs inside and out now. I don't need to ask anybody any questions. 

What do you think is a good, best practice there in terms of making sure that you're looping in a subject matter expert at the right time, like at the limits of your knowledge? 

Nick Wilkinson: Absolutely. And it's, I think it's a little bit different for every person depending on where they're at in their particular journey of learning different kinds of skills.

So, I mean, it's important to understand like at a fundamental level, like the building blocks that are being used to put your projects together. And not just, I mean, we're talking a lot about development, but also this applies equally to, like designer creative side of things as well. Like why do you use wire frames and where does that come into the process and when do you move into say, you know, tappable prototype or the final UI or motion graphics or whatever? Like understanding that part of the process is equally important. 

So at a fundamental level, you need to understand the building blocks. But I think then what's maybe more important is understanding, like the mindset of the people who are doing the work. Cuz there's a very different mindset just in terms of how your day is organized, between a builder and a manager. And for like, lack of a, like better descriptor, sales people are a kind of manager, even if they're not necessarily managing people.

Like they don't really build things other than, I mean, you could, you're building relationships obviously, but you're not, it's a different kind of work, than somebody who was, you know, needing to code for, you know, the whole day or, you know, putting lots of heads down time on a particular design.

So something that I've seen in the past as well is like where when you don't have an appreciation for how other people on your team work, then it's too easy just to kind of steamroll through and cause of a lot of chaos when you do need to reach out to that subject matter expert.

Like, kind of the last situation that you wanna find yourself in is, you know, you're talking with a lead, you're very excited. This seems like it might be a good project, but they had a bunch of questions for you that you couldn't answer. Maybe technical questions. And then your instinct is gonna be, Hey, I'm gonna like fire off an @ channel message to everybody, you know, on Slack in my company.

And like, see who can answer this question. And you're interrupting, you know, the day of a bunch of people. And when you're doing that on a recurring basis, that really can get annoying. And it's counterproductive beyond just being annoying. And if you're doing that a lot or scheduling like, hey, you know, like, do you have 15 minutes quick? I just need to touch base with you about lead conversation that I just had. 

Well, no, like people who build things need deep time, like deep focused work time in order to do the work that they do. And you need to be mindful and respective of that or respectful of that. So, I mean, a lot of the solution might come down to process, right?

So if you find that you're having to bug like 12 people every time you have a question, maybe figure out like, well, who are the one or two people who are gonna be go-tos and then work on an arrangement with them around, like, is it all right if I, you know, reach out to you every once in a while with these questions because these questions need to be answered by somebody?

And if it's not you, then can you gimme some ideas on who, cause I'm a little bit out of my depth, maybe, right? Or come up with, you know, just some rules of the game of what's gonna lead to a fair, kind of work environment where you need to ask these questions, somebody has to answer them.

But to minimize that disruption at the same time. So that's a part of it. I think also another part of it is making sure that you're leveling up all the time. So when a, when the team is asking you questions to ask a lead, take note of that and then make sure that you ask that again the next time you're in a similar situation.

Like, don't force the team to have to keep asking the same questions over and over again. Like, have your list of questions that you know you need to ask that you know the team is gonna be really interested in knowing about. And over time you grow your own expertise and your own kind of familiarity with all these different technical concepts.

And you might not be able to build them, but you understand, you know, from kind of a high level how they work and why the team would want to know that. And why it's important to, to try to get that information from a lead. Going the level beyond that, which makes it even more complicated is like, what do we need to know right now?

Like, what do we need in order to actually vet or qualify this client versus something that we can get into once we've actually got into our, say, kickoff sprint or discovery or envisioning session, whatever you wanna call that initial kind of engagement with a client. A lot of the nitty gritty details come out in that.

So there's, that's another kind of gray area is what do we need to know before we get into that engagement and what do I need to know to make sure that I think this is gonna be a good relationship where we can really deliver a lot of value for this particular client. So, I said a lot of words there. I don't think I actually answered your question.

Because it's complicated. 

Galen Low: I think you did even more than that. That was a empathy epiphany for me. That whole, you know, we talk a lot about, okay, like figure out how a person likes to work, especially as project managers we're like, Okay, how do you like to work? You know, how can I best communicate with you?

And then that example you gave, I know I can name some people I won't, but I can name some people in my past who were those people who were like, hey everybody, I have this deal I'm gonna close, like, what's the answer to this question? I need the answer in four minutes. 

You know, and then also the mechanism of going, Okay, got the answer. I'm gonna give it to the client now prospect now, but not actually taking the time to learn the thing that you just answered, right? Like I've seen so many people do it. And even just building that knowledge. And then the other thing I like that you woven was, very PM of you, is the process side of things, right?

Which is like, you can be building this process as you go and saying, Okay, well at these moments I've had to ask these questions. And this is what the team's interested in. And I don't wanna bug 'em all the time. Or maybe I have my, like informant, like informant, right? That person who's just, you know, I have a relationship with them, you know, I give 'em a chocolate bar and I only answer, I only ask them to answer questions after 3:00 PM and not on Fridays, but I can still do it. And that's my trusted person. 

And also gathering those questions and making a process out of it so that, you know, like we started this section out being like, well, you can't do both jobs, right? You can't be the salesperson or the account manager and also be working with the team through the whole thing that you just sold through.

You'd be doubling up on your hours. But you can, sort of make a system where you are getting informed and by staying informed, whatever you do independently is still connected with the reality of actually delivering the project. 

Nick Wilkinson: It's something I feel like I should say too, just to kind of provide context to all of the conversation really is, I'm a big advocate for like, workplaces being pretty calm. Like should be fun and it should be calm, and it should be a place where you go and do some satisfying work that you can feel proud of.

And a lot of what I'm saying is not really applicable to those environments that are not calm. Cuz sometimes it's expected just culturally that if, like sales is at like the top of the heap and if they have a question, everything is in service of lending that new project, right? And, I think that's a much more difficult problem to solve where like, systemically, that's what's expected.

I guess in my experience I've been very lucky to work in environments that have not been so much like that, or there's been at least opportunities to push back against that kind of burgeoning culture and an advocate for something that is a little bit more relaxed. I mean, I'm just of the opinion that when people are relaxed and happy, they tend to do better work.

And yeah, so that's where I'm coming from. And if anybody's listening and thinking, Well, that wouldn't work in my organization. It's like, well, probably not. If it's more like that other type that I, I gave an example of. 

Galen Low: I mean, even it's even just it would be insightful to be like, actually not every organization is like that.

You know, the aggressive hyper growth, you know, sales leads the way and whatever comes from that funnel, we do it, right? We find a way to do it. But, yeah. And that's for some people, and it's not for others, but it's also good to know that other organizations with different cultures exist. And there can be calm, right? Doesn't have to be madness at work. 

Nick Wilkinson: And actually as you were, just going back a few questions ago, kind of a hot tip that came up for me in terms of like, how do you get more like acumen I guess as a business development person or sales person from your execution team? 

Often when the team has questions for the lead, you know, they'll give you, you know, they'll kind of vomit up this list of like 20 questions. You can't actually ask 20 questions to the lead, right? Like, some of these questions don't need to be asked. Some of them might get way into the weeds and really just some of those are what's important. Something that I've always found that helps me a lot in terms of kind of upping my game to learn what the main concerns are of the team is rewriting those questions in my own words as opposed to just passing those along to the client.

So, I guess that comes from the experience as a PM, like you know that, I mean, the reason in part why we have a PM is because they can be a filter between the team and the client. And the PM knows how to talk to clients and like, what's gonna be important and a priority for a client versus stuff that they're just not gonna care about or not be paying attention to.

So in rewriting those questions and putting them on your own words, it helps you first of all understand what's even being asked as opposed to just passing along something that might be hyper technical. And if you get an answer to it, like the answer's not gonna even mean anything, and then you're just this middle person, like passing answers and questions back and forth, and it's just kind of wasting people's time.

So the more you can internalize those questions and put them in your own words, the faster you can scale up and also the more effective the conversation is gonna be with the lead as well. So just, yeah, hot tip for how to level up a little bit there. That's worked really well for me in the past.

Galen Low: I love that. I mean, you know, we are filters, in both roles, right? Project managers like you said, but also, you know, anything on the sales side, business development side, you know, accounts, client facing, anything. You are a filter, not a messenger, so to speak. And that's part of the value that you deliver.

Your job is not to pass notes back and forth, to your point, right? Your point is to engage with it and take a bit of more of an active role. I wonder if we could flip it a little bit just quickly. We talked about, you know, what can sales people, business development folks, account folks learn about project management and the way things are delivered?

What about the opposite? Like what should project managers seek to know about how the account team is doing their job, how the business development team is doing their job?

Nick Wilkinson: Yeah, absolutely. I think as a PM it's really easy to get bogged down in that, that "no mentality", right? Like, again, not just saying "no" outright, but finding those creative ways to say "no" at the point where it can actually be detrimental to a relationship in some cases.

And I know that's happened to me in some cases, in some projects in the past. So understanding that, I mean, the project is certainly important, but there's like a wider relationship if you zoom out and then zooming out even further, there's like, just the overall health of the company. And understanding that you play a really integral role in that at all those levels of zoom as a PM is really important.

So, also understanding that some things that you might be inclined to say "no" to, might be a good thing to say "yes" to, even if it is a little bit uncomfortable sometimes, because there is maybe a strategic reason for that. And there should be certainly a conversation around that if that's the case.

Like it shouldn't be just accepting at face value, like the people who are suggesting that you say "yes" to say something, that you say "yes" to something when your instinct is to say "no". Like that should be investigated more, right? There should be a conversation around that. But sometimes it's okay to be a little bit uncomfortable and go with it.

As long as it's clear that like your team is not adamant that this is a bad idea. So, and that's a skill that takes time to develop. And sometimes you're gonna make the wrong call and sometimes you'll agree to something and it is really, should not have been something that you should have said "yes" to.

And that's you know, building up your spidey-sense for next time, right? So that's, I think, a big part of it. And I think also, and this again may not be applicable to every organization out there, but the more PMs can be brought into the fold when it comes to the financial health of the company, that can be a really big thing as well.

Cause when you see okay, week to week, month to month, what the books look like, then that can really help to recontextualize your opinion about what we should take on and what we should not take on. 

Again, you know, there may be some things that we don't wanna take on because, oh, well, the team just did, you know, seven projects that were just like this and they need something new. Oh, but like, also we need to, you know, bring in some more revenue because, you know, we just hired seven new people and like whatever the reason is. So having that understanding of the financial health of the company is really critical.

And maybe not every PM in every organization is gonna be given that, but if you can advocate for that, and if you think it's a, if it's a possibility, then certainly you should try to insert yourself into situations like that, cuz it can be eye opening and really helpful. 

Galen Low: I like that. I even like just the literacy of, you know, if you have access to the information or if getting to that zoom out point where you're looking at the overall organization and how it functions.

It's actually empowering as well, right? Knowing the kind of impact you are having and can have on the organization, maybe just by being a bit uncomfortable and saying "yes" sometimes. And to your point, maybe not always being right about it, but that's how you kind of build up that instinct and practice that understanding of the broader business.

Because sometimes we can get very, you know, just myopic about our project, right? And that the impact we have is guarding it and making sure that, you know, it goes to plan and doesn't really change that much versus wait a minute, this is an opportunity for us to do way more, build a whole new practice, you know, with this request from a client.

That alone could help us, you know, grow the business and just having that eye for opportunity, I guess. 

Nick Wilkinson: Yeah. Exactly. And I think to help develop that eye for opportunity, it's sort of the flip of the advice that I gave earlier where I was talking about the business development person learning about the day to day reality of the PM. Likewise, the PM should be learning everything they can about what it is to be in business development and sales and learn about that process. How are you vetting leads? How are you qualifying them? What's that list of, you know, that checklist that we're looking for? And maybe you as a PM can actually provide some insight there.

Maybe there are things that the salesperson is not seeing that they should see that you can bring up. And also just understanding their struggles, because it's a very difficult thing - sales. And, you know, learning more about what are the different channels where either leaders come to us or where we're, you know, looking to do outbound sales and how does that work?

And, I think again, coming down to empathy, the more a PM can understand that being a salesperson isn't all like martinis and handshakes, you know, it helps you to get some empathy for what those real challenges are and to be supportive of those challenges. So then when you see opportunities as a PM to add more value for a client, then right away either you're able to jump on it in a way that's in line with the processes that business development is set up, or you can pull people in from business development and sales, who can help you with that.

And again, it's, you know, working towards cohesive team across the whole, the whole process. 

Galen Low: I like the sort of empathy lens, and I wonder if we can dive a bit deeper into some of the tougher stuff. Because one of the things that that you mentioned is, not every organization is going to have just even the culture or the context to begin that conversation. And I've worked in some places where, you know, there's quite a ferocious adversarial relationship between, for example, the sales team or the accounts team and the project team, and they're not even talking. 

Well, what are some ways that you would recommend starting to build that bridge when, you know, for the most parts they are actually enemies within that organization?

Nick Wilkinson: That's a really great question. And I think that's made so much more difficult through remote work as well. Cuz it's not like you can just bump into somebody on the other side of that fence at the water cooler and, you know, try to strike up a conversation or a friendship or whatever. Often it has to be a lot more intentional where you're actually then taking out people's time with scheduling something.

So that it's super hard. But despite that, I think that's kind of where things need to go is if you find that you are in that kind of adversarial environment, what's the lowest hanging fruit that you can find in terms of who you think is gonna be aligned with the way that you see things on the other side.

And then trying to make opportunities to get to know them more. And the more we know each other as people and knowing what our concerns are and where we're coming from, hopefully over time you can kind of leverage that into more of a relationship. So I think, I mean, that's where I would start.

And I mean, if that means having to go into the office a little bit more than you would like, if you're in a hybrid environment, then that's, you know, something that I would recommend that you do. But even if it's just like, you know, you have a few interactions with, as a PM with a salesperson.

And there's those handoff conversations between projects and you just, you know, you like your style, you think that you could get along with that person. Well, reach out, have a one on one, find out more about them. Learn more about, you know, just their, what's their origin story, right? And you can share yours.

And that helps to breakdown those barriers. Cuz I think I've been in situations before where there is a very strong 'us versus them' kind of mentality in sales contexts and also other contexts. And it's just too easy to dig in on the differences and complaining, Oh, they don't understand my concerns.

They don't understand what I do or how important I am, or whatever the situation is. But as soon as you start like learning about the person, that all just starts to crumble. And, even to an extreme, I can think of examples where the cliche of killing with kindness actually works. Where there's people, and again, I won't name names, but going back years and years ago in my own career, people that I really absolutely could not stand.

But the thing is, it was getting in the way of getting the work, right? And I realized that like there needs to be a way around this. And if it's not gonna come from the other person, like it's gonna have to come from me. And so I just started being super nice and not disingenuous, but just like pleasant because that doesn't cost me nothing.

Like I can just be nice to this person whenever I have a call with them or whenever I see them, and then maybe ask them a few questions about themselves. Cuz again, that's gonna cost me nothing. And like, what's the worst that's gonna happen? And over time, we actually were able to build up a very solid working relationship where then that person would reach out to me for things and asking for help and I would help them and they would help me with things.

And it was great. So, I mean, I'm not gonna take this one data point and expect that's gonna work at every situation, but it is possible. And I think that's really the key is learning of what each other as people and seeing what you can do. 

And if you are in that kind of environment that is very hyper aggressive and very sales oriented, maybe, you know, learning about each other is that first way to help bring that sort of system down and realize that there's other ways of doing work that can be a lot more satisfying and a lot more enjoyable. 

Galen Low: I really like that approach. I like how targeted and individually approach is because, you know, there's a way to look at it and say like, Oh, I'll set up a process where these two teams all get together and meet, you know, every quarter to talk about what they're doing.

But just like any adversarial relationship, like you said, right, as you start to connect as humans, some of that just falls away because, you know, the actual, you know, reasons why we are combatants is somewhat artificial in a way versus, you know, who we are as humans. I really like that. I like that approach.

Nick Wilkinson: Having said that, there are just some jerks out there too, that no matter how nice you are to them, they're not gonna change. And like that's, you know, then at least you have that data, right? You understand where you stand with that person and you can like move on and try something else. So, yeah, it's good to be adaptive to whatever's going on.

Galen Low: I like the strategic angle there, right? Like, and I think that people have that, you know, they have this false impression, I think. Okay, my opinion is that, there is a false impression that being kind, you know, is this sort of, sort of like vulnerability or it's like a weak way of like approaching a problem when somebody's a jerk.

But to your point, it costs you nothing and then you can plan, right? It's actually a strategic thing to be like, Cool, I'm gonna like shower you with kindness, and maybe it gets somewhere. And if it doesn't, it tells me more about what I need to know to sort of navigate this relationship. 

Nick Wilkinson: Yeah. And I think you struck on something really important there is that vulnerability, showing vulnerability is incredibly powerful.

Because chances are that whatever you're feeling in a situation, other people are too. And if you open up about that and share legitimately what you're feeling and you're, I mean, there, there's a kind of a safe and, you know, like better way to do this. But if you really share and be open with how you're feeling about something, chances are that's gonna resonate with people and it's gonna disarm them.

And, you know, they might not necessarily agree with you, but at least it gets things back to the point where you can have like a civil and productive conversation about things. So again that's a whole other topic that, you know, requires a lot of like mastery and or practice to get to the point where you have mastery at that.

But, yeah, being vulnerable isn't necessarily a bad thing and it shouldn't be seen as a bad thing. 

Galen Low: I love that. I'm gonna close out with a curve ball, which is, you know, we talked about zooming out and different levels. We've zoomed in to the point where we're talking about individuals and their dynamic.

But for organizations where they don't have that culture, where they do have a bit of an adversarial tension that isn't that productive between their, you know, business development teams and their delivery teams. And they're also not willing to invest in it. When you wrap all these things together, like what is the upside for a leader of a business to really sell this through, to say, this is gonna be worth it. It's worth you investing the time to make sure that you have a healthy tension between these two teams because this is the thing that you'll benefit from.

Nick Wilkinson: Yeah, that's a really good question. And I think it really comes down to what the values are. Like the real values of that organization and the people at the top of the organization. For some organizations the value is profit. And if that's the case then, and if you found that you were profitable running our organization that has that kind of hyper competitive and aggressive environment, well then, you know, do what works for you, right?

And people will either gravitate towards that or they won't. But that's kind of where things are at. But I think what's really important is for kinda those people at the top of an organization to be honest about what their values are. Because often organizations can say that, Oh yeah, we really value, you know, your mental health and that you're doing satisfying work and you know that you wake up loving what you do.

But in terms of like, well, what does that mean in terms of like, the follow through, right? Like how are you doing that? How are you creating that environment as a leader, as a manager? So easy to say, but you know, more difficult to do. And it could be that people say that, but their values are still profit.

In which case, you know, keep moving on, you know, if that's what's working for you and you enjoy that, well great. But I think for those organizations, I really do care. And are always looking for the ways to ensure that their team is set up to do the best possible work that they can do.

It's really important to make sure that those teams are all working together really well, right? It's like you're building a machine and you can't have an engine where some part of the engine thinks it's more important than the others. Everything is equally critical and if any part fails, the whole thing fails.

Or at least doesn't perform as well as it could otherwise. So I think it really does pay to, you know, to look deeply at this and how everyone's working together and making sure that people aren't just saying, Oh yeah, no, this is fine. And know, we're all hugging it out and enjoying working together. But like, is that actually true? And I mean, I think there's multiple layers to your question here. 

The thing is, I think for people at the top of an organization, it's super hard to even figure that out, right? Because people are gonna response to you differently than they would, say somebody who they perceive as a peer or somebody who is, you know, somewhere else in the organization as opposed to a boss. But, I guess to bring this back to your main question, like what is the value of that?

I think the value is that you, it affects every part of your business. It affects retention. It affects just your like day to day work satisfaction across the whole organization. I think it ultimately affects bottom line cuz the people are happier and doing better work, the quality of that work goes up.

 The level of pride that people have goes up and clients are ultimately gonna be more, finding more value in the work that is coming out of a team that operates like that. Also, people are gonna gravitate towards wanting to work at a company like that. 

And again, just like shameless plug for Steamclock, that's why I had my eye on the company for as many years as I did, is because there's this fierce commitment to quality. And really zeroing in on doing a few things exceptionally well, and their marketing worked on me. I applied for a job there. And then I was happy to see that was not just marketing once I actually got into the company, that it's a real thing. So I think when companies focus on that, there are benefits all across the board.

And, including the bottom line. But it's important to remember that like if you're an organization that's moving towards this, those benefits aren't gonna be seen on day one. Like this is a long term investment that carries on forever. It doesn't ever end. You can't stop, you know, caring about your people or investing in your people or fostering that kind of environment. It's something that you do every day.

So yeah, here's to hoping that there are more organizations out there that are, you know, leaning more towards that side as opposed to the more aggressive or competitive side of things. 

Galen Low: What I like that you did there is actually, and I can see you've probably giving that pitch if you were in an organization that sort of needed a bit of this transformation, but actually it is still profit. Because in a way, if you have a well running machine, you know, it's not, you know, leaking talent out of the bottom. People aren't burning out. People are, you know, feeling good about the work and they're all working as one machine, instead of a machine that thinks it's more important than you know, this other machine. 

Then it actually does lead to better retention of your clients, better profit, or it can lead to. And I like that even though we kind of started that out being like, Okay, well maybe if you're just profit hungry, this isn't for you. But actually the rest of it is, that is the upside. The upside of all of these things is that, you know, profit as a measure of how relevant and successful this business is, it does actually impact that, and there should be this synergy. There should be this empathy being built between these two teams because that's the upset.

Nick Wilkinson: Yeah, absolutely. 

Galen Low: Awesome. Nick, this was great. I really enjoyed our conversation. So many insights here. We came here to talk about the tension between BD teams and project managers, and I think we did, my gosh, so much more in there. I'm gonna have to have you back in that whole trust building side of things as well.

Nick Wilkinson: For sure. This is a huge amount of fun. Thanks so much for having me and yeah, I'd love to come back. This is great.

Galen Low: So what do you think? 

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