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Career DevelopmentDPM PodcastLeadership & Team Management

How To Find And Develop DPMs Who Can Own Technical Complexity (with Matthew O’Bryant from Oomph Inc.)

By 08/02/2021 April 28th, 2021 No Comments

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Learn to hire and grow DPMs who are technical enough to own complex projects with VP, Professional Services at Oomph, Matthew O’Bryant.

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Audio Transcription:

Galen Low

So you’re interviewing a candidate who is vying to become the next digital project manager on your team. They’re ticking a lot of the boxes, but they’re stumbling a bit when you ask about the technologies they’ve worked within the past. Was it built in PHP or an ASP? Can’t remember. What it host on the cloud or was it on-prem? Not sure. Was it caching that helped the speed issues or was it the CDN that made all the difference in the end? Uhhhh…

Last week you interviewed someone who could probably write a whole statement of work in Python, but they kind of lacked that bedside manner required to ever let you put them in front of your clients. Are you being too picky? Does the person you hire even need to be all that technical? How can it be so hard to find someone for such an in-demand role? If this is something you can relate to — if hiring a DPM is starting to feel a little bit more like catching a fly with a pair of chopsticks, well, riding backward on a horse blindfolded — then keep listening. We’re going to break down the must-have ingredients to look for in a good DPM and how to sculpt your team into your A-players.

Galen Low

Hey, thanks for tuning in. My name is Galen Low with thedigitalprojectmanager.com. 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 deliver projects better. If you want to hear more about that, head over to thedigitalprojectmanager.com.

Galen Low

All right. Hey, everyone, thanks for hanging out with us on the DPM podcast. My guest today is a longtime digital project manager who has spent over 20 years working in digital agency contexts, as well as just technology in general. From humble beginnings as a Microsoft Certified Systems Engineer to building large scale ecommerce and marketing websites for large national brands, he has run the gamut of the digital world. Today, he is the VP of Professional Services at Oomph, located in Providence, Rhode Island. In his spare time, he is a disciple of the culinary arts who is currently hell-bent on mastering his barbecue brisket recipe and is also one of the organizers of the Boston Digital Project Manager Meetup Group.

Galen Low

Folks, Please welcome Matthew O’Bryant. Hi, Matt.

Matthew O’Bryant

Hey. Hello. Hello. Thanks for having me. It’s really good to be with you.

Galen Low

It’s great to have you on the show. Yeah, I’m looking forward to chatting.

Matthew O’Bryant

It’s good to talk project management with another fellow PM geek.

Galen Low

Absolutely. We’re going to nerd out today. First, let’s let the folks know about yourself. So you’ve made an impressive ascent from Digital Project Manager to becoming a member of the leadership team at Oomph. And I imagine it’s been a lot of blood, sweat, and tears.

Galen Low

So I thought I’d ask you, where do you get your inspiration from? What inspires you to keep plugging away at it?

Matthew O’Bryant

Yeah, that’s a great question. You know, definitely blood, sweat, probably too few, many tears for me. It’s a drive to just understand things.

Matthew O’Bryant

I really like to understand how things are made and how they’re built, you know, the how and the why. And it’s not just in technology like, you know, on the side. Everybody’s got their hobbies right. I’m way into right now woodworking. It’s super interesting to see how things are physically built. I’m super motivated when I learn more about the kind of the under the hood, the tech, the you know, the how, the why and just, you know, being able to see the great things that, you know, the teams that I’m working with and have worked with in the past that we’re able to build and to create together. It’s awesome. It’s awesome. I’m really inspired by other people.

Galen Low

So we’re going to get you to make some chairs for us eventually. Maybe some nice rocking chairs. One thing I wanted to ask inside or outside of work, is there anything that you’ve stumbled upon recently that’s just making your life super awesome?

Matthew O’Bryant

So, yes. And it is the Mr. Chicken covers of pop songs on YouTube. It’s a some person with a rubber chicken that is just squeezing that thing in and out and like, you know, it’s chicken singing along with the music. It’s completely hilarious.

Galen Low

Is it in pitch, the rubber chicken?

Matthew O’Bryant

Pretty close, I would say.

Galen Low

Pretty impressive.

Matthew O’Bryant

Pretty close. Yeah. And you have to check out Bohemian Rhapsody. It’s hands down. I think it’s the funniest one. Although I would I will the take on me. A-ha, take on me, it’s pretty good too.

Galen Low

All right. So why don’t we get into it?

Galen Low

Let’s, let’s talk about hiring and nurturing digital project managers that are or can become in some way, shape, or form technical. So just to clarify, not necessarily a technical paper, say that’s a bit of a different thing, but we’re going to be talking about how you find folks who are willing to become technical enough?

Galen Low

I guess the folks who are willing to immerse themselves in technology and in the process, own things, get things done. You yourself, you’re someone that I consider to be quite technical. You are legitimately a systems engineer who became a project manager and who is now a team leader. You’ve written code. You’ve migrated databases. You’ve created something sort of like Acquia Site Factory before Site Factory even existed. So I think you’re a pretty technical guy and arguably a lot of digital project managers and a lot of our listeners may have come at it from the other direction. So, from less complex digital projects to increasingly more complex ones, and I suspect that your expectations might be a little higher than the average bear when it comes to technical prowess as you’re sifting through that candidate pool. But it’s also why I’m really keen to get your perspective on how you hire and grow good teams. How would you describe the role of a digital project manager on your team?

Matthew O’Bryant

Yeah, I mean, that’s a great question to boil it down to the basics. I consider them to be the owner. Right?

Matthew O’Bryant

You are the person that owns the project. You need to own all the details of the project. You are not that you’re solely responsible for the success, but I feel like, you know, you shoulder a good amount of that responsibility to help drive and make that project a success. And so, yeah, you definitely use it. You own it. Your client-facing you’re talking to the client. You’re also inward-facing working with the team and you’re working with strategy designed account management, development, engineering. So you’ve really you’ve got to own all those different pieces of the project and kind of bring them all together.

Galen Low

Yeah, that’s a fair point. You are. And so even I kind of framed it as being as technical equals like development savageness, but not necessarily even that like knowing and owning each piece of that lifecycle, whether it’s in design or UX or development or testing or prelaunch.

Galen Low

It’s kind of this that sort of definition of technical and the willingness to become technical. I guess for our conversation, we mean not just code and building stuff, but the whole stick.

Matthew O’Bryant

Yeah, no, absolutely. Because I mean, all of those other pieces, we do use technology to do those things, so. Yeah, yeah.

Matthew O’Bryant

And I mean take design as an example, like you should be familiar with the technical terminology and aspects of design. Right. So to me, that’s important to understand, to understand what are UX and our design team is doing and what they’re talking about and so on and so forth. So yeah.

Galen Low

I like that. I think that maybe brings you to my next question, which is what is the most important thing that in your eyes a good DPM brings in terms of value to clients and also to the teams?

Matthew O’Bryant

So on the client-side, I look at project managers as their professional technology translators.

Matthew O’Bryant

Right. So, again, because you’re both inward and outward-facing, it’s the ability to kind of take the complex and to be able to distill it down into something that is understandable for the clients so that, you know, and then conversely, you’re able to talk with the client and understand their business goals and then help to kind of bubble that up to the technology teams, the design teams, etcetera, and help them to understand what it is that they need to achieve with what the outcomes are that would help to to to make a project successful. I mean, when I used to have a resume, but when I was circulating my resume, I liked to describe myself as someone who thinks in zeros and ones, but speaks English.

Matthew O’Bryant

So that ability to be able to think technically but still be able to explain it to a client in a way that is going to be understandable to them. But to I think, you know, when you understand the technology and just how complex and difficult things are, I think that positions you as a project manager to much better communicate the value that your company is bringing to the client and bringing to the project, you know, to them. They might think that what you’re working on is not all that complex. They just think about the end outcome. But there could be so many things that have to be done to to get to that point. And so if you can help your clients to understand all that goes into it, all the process, all the technology, everything that you do to arrive at that end product, I definitely think you’re helping position them to really see the value that the company as a whole is bringing.

Galen Low

Yeah, I really like that. It’s like a distillation. Like the skill is also is. Yes. Being the messenger. Yes. Being the proverbial Babel fish, but also distilling the important things in a way that they’ll get value out of.

Matthew O’Bryant

Yeah. And then and then back to the team. I think for you when you understand what someone’s doing on a regular basis, how many, how many, how many of us have said to somebody like, why is this taking so long?

Matthew O’Bryant

Right. Well, if you understand why it’s taking so long, that gives you a little bit of an. Right, when your engineer, your developer says like, oh, man, I’m really struggling with my local environment today. And for me, a couple of years ago, I was like, man, I keep hearing this from people over and over again. Why is this so hard?

Matthew O’Bryant

You know, I built websites and all I did was set up like a MAMP or something like that. And I was up and running. So I was like, I’m going to see how hard this is. And then I decided to just, like, clone the repo and try to set my local up running Lando.

Matthew O’Bryant

And I was like, wow, this is actually really complex and hard. And I ran into error after hour after error, but it built empathy for me that, like, yeah, this is not easy stuff. It’s difficult. And yeah. So so I think empathy is an important thing. I also think that when you speak the same language like it just going to increase, it’s going to improve the communication between the entire team. Like if you know what they’re talking about, you’re not going to have this crazy blank stare on your face. And you know, or like somebody says something to you and you’re like, OK, and you walk away and you really don’t get it. Like, if you can communicate better when you’re speaking the same language, you’re apt to have better results and accomplish more together as a group. And then lastly, I feel like for the team, when you’re a little bit more technical, I feel like you can kind of be that first line of defense. Right. And like you’re a tier one support so that you’re kind of knocking things down, answering questions for your clients, and letting your team kind of focus on the more important things that they really should be spending their time on. And I think when you do that for them, I mean, your team is just going to love you and appreciate that they’re not getting interrupted throughout the course of the day. So there’s a lot of good that brings to the table.

Galen Low

That is a lot.

Galen Low

Yes. For anyone out there, there’s a digital project manager and isn’t sure the value that they bring or how to communicate it. That’s probably a good start.

Galen Low

Which maybe brings me to a loaded question? Yeah, it’s a loaded question. And my loaded question is how technical does a DPM on your team need to be? So in other words, what do you expect a DPM to be able to do to drive your projects to successful delivery? So, for example, do they need to know how to write code?

Matthew O’Bryant

Maybe. So is it an absolute requirement to know how to write code? No, of course not.

Matthew O’Bryant

But I do think that it’s important for them to understand a little bit about how code is written. And also, I think I would like them to have some pretty good basic working knowledge of like HTML and CSS. That’s really important because again, you think about that like tier-one support type of thing. I would like you to be able to pull something up in a browser and write, click and inspect element and look at it and be like, oh, this is a little bit off. Or like maybe do a quick in browser mockup to show a client what something might look like and get their buy-in on that general approach. Like, I think that’s really important and I do expect them to know some of that stuff. But do I expect we work with PHP and JavaScript and do I expect them to know how to write code and those languages? No, not at all.

Galen Low

Is there anyone on your team currently who has access to Git to actually commit?

Matthew O’Bryant

Yeah, absolutely.

Matthew O’Bryant

Yeah. Yeah, absolutely.

Matthew O’Bryant

Is that there’s a bunch of us that actually have access to Git and do that. They some even can contribute to the PR process a little bit for simpler PR. It’s like.

Matthew O’Bryant

Yeah, like if it’s a fast change like yeah I have a couple of PMs who have no problem going to get. That’s good approved. Ship it. You know.

Galen Low

Nice. Yeah. I love it. How do you go about coming back to that sort of tier-one model? I’m thinking I’ve seen both. I’ve seen those project managers who think they can do two one, but everyone on the team is like, no, no, no, no, no, don’t speak because you’re going to say the wrong thing versus building that trust. So people are like, oh, yeah, that person knows what they’re talking about. We’ve shown them how the process works.

Galen Low

They’re going to do fine to answer these questions and then they’ll escalate us when necessary. How do you sort of get people on your team to that point where the team trusts them and they trust themselves to, you know, not do something that’s completely, you know, outside of the process?

Matthew O’Bryant

Yeah, that’s a great question. I mean, I think we certainly don’t just throw them into the deep end of the pool and say, figure it out. You know, the way that our organization is structured, we do actually have teams that are dedicated, teams that work together all the time.

Matthew O’Bryant

So they’re dedicated, cross-functional teams. So they get used to working with one another and they develop a rapport in a relationship with one another. So I think, you know, much more rather than bouncing around like I’m working with this group for this project and this group for this project, there’s a rapport and a level of trust and comfort that gets developed there over time. But having, you know, having a technical person on a call with you, you know, to be able to kind of see what they’re doing and to be able to be there for support for a while is definitely helpful. But in terms of like getting them comfortable, you know, we strongly encourage that our PMs try to level up, if you will, from a technical ability side of things. So we firmly encourage people to do some training. We encourage them to build, build, build a demo site or something like that, to try to like dive into the coding — not coding, but the technical side of things and really start to learn some of the technology.

Galen Low

I love that sort of learn by doing. And then also what you’re saying about like having a technical person on a call and folks who have worked with me will know that I will always say, “oh, so and so, keep me honest here, but the answer is blah, blah, blah”. And then they’re like, “sort of” then you can to learn for next time.

Matthew O’Bryant

Yeah. Yeah. And to me, one of the things that I always encourage people to do is from the project management side, it’s like ask questions.

Matthew O’Bryant

I’m probably like I’m one of those people who’s really annoying because I ask a lot of questions, you know, don’t tell them to do it. Like do it respectfully.

Matthew O’Bryant

And B, don’t do in front of the client like you don’t want to come across and sounding like you’re questioning the solutions.

Matthew O’Bryant

But, hey, take you know, take ten minutes after the call and kind of ask your engineer, “So like, why did you recommend that? I’m really curious. What’s the benefits to this?” So yeah, definitely be inquisitive and be curious and you want to know why developers and engineers are making the recommendations that they do because you’ll learn a lot from them.

Galen Low

I love that kind of zeroing in on the why. Yeah, because that’s generally speaking, A) what you’ll have to explain to a client or a sponsor or stakeholders. And B) it kind of helps that core understanding for yourself. One of the things we talked about in the past was kind of knowing and understanding technical terms. So like the lingo as well. Yeah. What’s your take on that? And what are some of the expectations you have folks on your team to kind of speak and speak the technical — what am I trying to say — use the technical terms correctly.

Matthew O’Bryant

Yeah, no, I fully expect to do that. Currently, we’re mainly working with Drupal.

Matthew O’Bryant

We have some WordPress clients. We’re starting to get into some decoupled stuff with like API first headless CMS tools. But I hundred percent expect them to know the difference between a module and a plugin. If you say that you’re going to install a plugin in Drupal, I’m like, no, because there’s no plugins in Drupal. It’s you know, if their modules plugins are in WordPress or like content type as a Drupal term, custom post type is a WordPress term. So it’s important. I know it may sound like it’s a little thing, but I think it’s important to to understand the terminology because I just it make it gives me confidence and I’m sure it would give the client a little bit more confidence thing. You do, in fact, know what you’re talking about. So definitely need to learn the lingo, need to learn the terms and not just learning the lingo or you actually need to know what they are.

Galen Low

Yeah. Yeah. Fair. And also, I mean, some of our clients now are savvy. They know what all the terms are. They’ve studied up on Drupal. You know, they probably put on the project because they have that knowledge.

Matthew O’Bryant

So yeah, absolutely. Sometimes you have in-house I mean, sometimes we do like staff augmentation projects. We were working with an in-house dev team. So we go, wow, yeah. You really got to know what you’re talking about.

Galen Low

Is there somewhere that you send someone immediately after they make that mistake and they say, plugin when I go to?

Matthew O’Bryant

No, there’s no like a virtual dunce cap that they have to wear.

Galen Low

Ha, no I mean where to learn or to skill up. Haha, “Go to the corner!”.

Matthew O’Bryant

Exactly. Yeah, no, no, absolutely. We again, for Drupal we have a drupalize.me account.

Matthew O’Bryant

So yeah, we, we absolutely encourage and offer that to new hires to go through that training, it’s fantastic, it’s you know, really there’s a lot like short chapters that you can go through pretty quickly to learn some of the terminology. So that’s a really good resource for Drupal, for WordPress. I mean, there’s a million things out there. So, yeah, we do in some cases, too, you can use like Codecademy, Udemy, or like Lynda.com or like there’s some LinkedIn training, too.

Galen Low

Let’s dive into hiring. So when you’re hiring — when you’re hiring for a digital project manager, specifically — what are some of the things that you’re looking for? Are you usually looking for someone who’s kind of turnkey and can just like plugin? Or do you specifically look for talent that you can foster and sculpt and grow them into what you need them to be?

Matthew O’Bryant

So it depends.

Matthew O’Bryant

Sometimes you are looking for more of that turnkey option, someone who’s got a little bit more experience, get a little bit more techie in them. But in some cases, we may not have the budget for it. So it really does depend. But the one thing that I will say is, again, we’re mostly at this point a Drupal shop. Right? And it’s kind of a more niche area of development. So there’s not a ton of (that I’ve come across anyway) resumes that I’ve received, not a ton of people who are like all I do is manage Drupal projects. So oftentimes they’re not completely turnkey anyway. So for me, it’s it’s not as important. And the other thing to keep in mind, too, is technology changes. When I started, we were mostly at a WordPress shop. So, you know, and like I said, we’re moving in the direction of working with other tools. Tools change. So it you know, as long as you’re a technically savvy individual, I think that’s the key thing. And what I look for is more on the like the quality side, who are you as an individual and a person. And I think that’s the key thing. Are you willing to learn? Do I see kind of like that roll up your sleeves and figure it out mentality. That’s the thing. That’s the most important to me.

Galen Low

I like that, and how that kind of shapes out in a resume — if we’re talking about the process when you’re kind of going through that stack of resumes, is there anything around that kind of jumps out at you that says, yes, I am a roll up my sleeves kind of problem solver?

Matthew O’Bryant

Yeah, I think so.

Matthew O’Bryant

And it’s in it’s less about like the. You know, the million bullet points of your responsibilities that you had on your resume. One of the things that I like to see is more around the accomplishments, you know, that you made as a project manager, you know. So was there some really challenging thing that came in? And you guys, you and your team, you figured out how to how to get it done? It’s less about like I managed 10 clients and I you know, I was blah, blah, blah, blah, like it just a bunch of bullet points of the core responsibilities of things you did. We know what the core responsibilities of project manager are. So I want to see is accomplishments, what are some really big, cool things that you did and that you accomplished to me that’s going to jump out at me way, way more and make me think like, wow, you know, this person can really get stuff done. And I would love to see some variety, too, if possible. If it’s all the same thing, then that doesn’t necessarily tell me that you’re a roll up your sleeves and figure it out kind of person. That means that if maybe you’re just kind of more like a you know, we’re just we’re stamping widgets here, if you like. We’re cranking out the same thing. And it’s more the process that you’re following than you’re thinking ability. That is what’s making things successful.

Galen Low

And when you say variety as in sort of types of projects and maybe scale.

Matthew O’Bryant

Yeah, absolutely. Yep. Can you do big things? Can you do small things? Yeah. Have you worked on different with different tools?

Matthew O’Bryant

And again doesn’t have to be Drupal — I don’t care. But have you worked with a variety of different platforms and tools? Absolutely. That’s I think that’s very, very critical because, again, that shows me your critical thinking skills and your ability to just dive in and figure out a platform.

Galen Low

For the hiring managers listening, I thought I’d ask, do you have like a silver bullet favorite question to ask in an interview that kind of helps you understand whether a candidate will have that roll up their sleeves, get it done, problem-solving mentality?

Matthew O’Bryant

Do I have one — no.

Matthew O’Bryant

I don’t have a silver bullet necessarily, but what we do use from a question perspective, but what we do use is a tool. If I can talk about that for a little bit. Yeah, let’s do it. I cool. So. We use a particular tool in our hiring process called the Predictive Index (PI). And what that is, is a it’s kind of like one of those personality tests that you take. It’s not too different from, like a DiSC profiler or something like that. Meyers Briggs is another one. And so this is a measure of like kind of who you are as a person or like formality. Do I need to follow rules or like can I work in ambiguous situations? Like, you know, am I looking for, you know, am I super outgoing and able to, like, meet new people, or am I kind of reserved and by using a tool like this? What we’ve done is it has something called a pro. And what a pro is, is you say, all right, for this particular position, these are all the qualities that I think would make this person like the ideal candidate. Right. And so then and we did that with a couple of different people in our organization. And then somebody takes their test and then you can kind of you can compare them and say, like, how closely does this person align to our pro, if you will, you know, and will give you a guide like how they might struggle in this area. This is where they’re really going so well. This is how you can help them grow. This is how you can help them get better at their job. And for me, what this does is it takes a little bit of the gut feel out of the hiring process and it uses a little bit more data and science so that that way, if you’ve got like two or three top candidates, they’re all pretty equal, you know, all pretty even this is going to really help kind of make that decision for us.

Galen Low

Whereabouts in the process is this. Is it like a screener, and then please fill out this, you know, the predictive index assignment, and then interviews begin, or is it later?

Matthew O’Bryant

You know, so so it’s we screen a little bit, we’ll do an interview and then we’ll have them fill out the PI. And, you know, but we could do it a little bit earlier because the PI tool can actually give you suggested interview questions as well based off of this person. So, I mean, I think that’s pretty cool. You can use it a little bit earlier, but I typically don’t. I usually just kind of reference it towards the end of the process and that that makes sense.

Galen Low

One thing I had in my head is, are you usually looking for the same thing? Like, is there a mold or is it a mix that you’re looking for or neither?

Matthew O’Bryant

I’m looking for the same thing, honestly. Yeah. I mean, we can all be different people. And again, you don’t have to match that pattern perfectly.

Matthew O’Bryant

We have a lot of great PMs on our team and everybody is a little bit different. Right. But I’m just looking for you to have, like, pieces of those things that, you know, kind of I think you’re going to make you great.

Galen Low

Makes sense. I like that. For our hiring manager listeners: what are some of the things like the big cardinal sins that you’ve seen from DPM candidates that you’re like, OK, no, I’m not going to hire you. You just said that thing and know just from you saying that that you’re not the right fit.

Matthew O’Bryant

Don’t, don’t, don’t fake it. You know, like it. If you haven’t worked on Drupal, don’t say that you have right. Again, going back to like, “Oh yeah. Like I’m super familiar with all the plugins and stuff”. Like it’s like I come on, just say I’ve never worked in it. I’ve worked in, I’ve worked, I’ve worked in this system or that system. But like I have, you know, I understand at its core how systems work. And I’m pretty sure I can figure this one out right. Just be honest. That’s what we’re looking for.

Galen Low

And I think, yeah, I like that honesty. And also, like the person who’s going to fake it is probably the person who’s not going to ask those questions to better understand what the team’s doing because it can be like that. Just fake it. Yeah. Yeah, absolutely. All right. We talked about the predictive index and how you like to add a little bit of science to that once you’ve kind of gotten down to that shortlist of candidates. But when you’re getting to that shortlist of candidates, what are some of the most important things that impact your decision to add them to that shortlist? Like what are the key ingredients that, you know, you can work with? What are the things that makes you think, yeah, this person is made of the right stuff?

Matthew O’Bryant

Yeah. Yeah, definitely. Again, it’s about it’s not so much about the skills, but it’s about like your abilities and your critical thinking skill, your critical thinking abilities.

Matthew O’Bryant

Right. And again, those are those bootstrapping, like “I’ll roll up my sleeves, and I’m going to figure it out. I can pivot. I can learn.” One thing that I forgot to mention that I wanted to mention to you was like during the interview process, one way that we can get a good sense for people’s ability. To do this is we actually role-plays in our interviews, which is really fun, and I don’t I tend not to tell people about it in advance, so I just kind of spring it on them because I feel like as a right, like sometimes you have advanced notice as to like difficult situations and you can kind of prep for it like, oh, you want to talk about what you want to talk about. I could only get prepared for that. Sometimes you on a call and like my client, just drop the bomb in your lap and you’ve got to be able to quickly handle that circumstance and figure out like what you’re going to do. Maybe you need to pivot. Maybe you need to figure something out on the fly. And so what we do is we’ve written up these scenarios. They’re real — from circumstances that other PMs on our staff have dealt with in the past. And essentially what they have to do is I let them read the scenario and it may be like, OK, you’re on a call and you have to let the client know that you’re asking for more budget because of X, Y, Z or like you’re on a call. And the client just says, like, hey, you remember that thing that I was supposed to get you, that content? Well, I can’t get it for you for another three weeks because of X, Y, Z, but we still have the launch on time.

Matthew O’Bryant

Right. So they get to read through the scenario.

Matthew O’Bryant

They can ask me questions, which is also, I think, really key. Like if you can read through that and ask me no questions, like, I don’t know. That tells me something about your thought process.

Galen Low

This is before the scenario begins. It’s like, you know, actually “what is what exactly does this mean?”

Matthew O’Bryant

Yeah, exactly. And I tell them that all the time. Read through it, ask me any questions that you have now and then when you’re good to go. What I want you to do is literally, you know, pick your hand up to say, “ring, ring.” Right. And you’re calling me and on the client and you know, sometimes I’m nice and sometimes it can be challenging, but it’s fun to see how they react.

Matthew O’Bryant

Yeah. Because, again, it’s about your ability to kind of think on the fly. And I think that gives me a good indication as to how you’re able to think in difficult circumstances.

Galen Low

And what I like is that part of that sort of quote-unquote test in the role play. Is that asking questions before the scenario starts? I think that’s a really, really cool tip for folks who are, you know, designing their interview process and think of it as, OK, let’s see how this person acts when they have their hand up to the face like it’s a phone versus the prep that they’re doing in advance and how they’re thinking about that. I really like that.

Matthew O’Bryant

Exactly. Exactly.

Galen Low

All right. So let’s move on from hiring. And let’s say, you know, once you’ve made your decision, I imagine there’s always a little bit of sculpting required to make it work for your team or, you know, be just those nuances. So, for example, like you mentioned, you might bring on someone who is familiar with CMS in general, maybe not specifically Drupal, maybe not even WordPress, maybe something proprietary. And, you know, you kind of need to baptize them into the way things work. But also, I think you’re a pretty strong proponent of just continuous improvement, personal growth, you know, iteration over iteration. So I thought I’d ask you about nurturing your team. So, like, how do you help your team grow and expand their knowledge and learn?

Matthew O’Bryant

Yeah, that’s a great question. I mean, I think it starts with monthly one on ones, you know, making sure that we’re touching base on a regular basis with each team member.

Matthew O’Bryant

So, I meet with each project manager just to see how things are going, kind of check-in on some of our goals that we’ve set for them each time we do like an annual or regular performance assessment. We set goals that we want them to achieve and that’s a collaborative process with them. So it just kind of checking in and see how they’re doing on that. What assistance do they need? Another thing that I actually think is interesting is I talked about our kind of like our cross-functional teams right earlier, but we also have like departmental groups that we call guilds.

Matthew O’Bryant

So like, yeah, we got a PM guild. And so our PM guild meets twice a month for an hour to get together and just kind of like talk about different things like, hey, you know, what’s new?

Matthew O’Bryant

What have you learned recently? What are you working on? What challenges have you encountered? And it gives them the ability to kind of just share knowledge with one another and kind of, you know, help each other sharpen their skills a little bit and then. And then the last. Thing that I really like is we have a professional growth program we call PG time, and so everybody gets in a lot of time and it’s similar to PTO, right. So you just like you’re requesting time off for vacation, you request PG time. So we have the tool that you’re going to request the day or whatever it is and say, hey, I want to take a day off because I want to attend this class or this conference. And it’s it then gets sent to your manager. Your manager has to review and approve it and most of you can approve it. But of course, we want to make sure that they’re using that time to grow their skills as a project manager or that it’s dedicated towards something that we think makes the most sense for that individual. But then once that’s approved, I mean, that goes on the calendar. You’re out of office like we treat it like PTO as well. Like you can’t just say like, oh, man. So can you move your PG time? Because why don’t we just tell we don’t and we don’t tell the clients that it’s PG time because then they’re like, well, who cares?

Matthew O’Bryant

Get them back on the project. We just like that person is they’re not available.

Matthew O’Bryant

They’re off today. So and that ensures that they’re able to get the give it the time and attention and focus that it truly deserves.

Galen Low

In terms of just professional growth and personal growth, I guess.

Galen Low

Is there anything that you if they come to you with asking for recommendations, is there something that you recommend to your team members, especially those who want to take on more complex projects and they really want to scale up in digital?

Matthew O’Bryant

Yeah, I mean, take advantage of the community, right.

Matthew O’Bryant

You know, thedigitalprojectmanager.com, there’s also local groups. As you mentioned earlier, I helped organize and run the Boston DPM Meetup Group, and we meet once a month, second Tuesday of the month. And we’ve had so many amazing visiting speakers. And the thing that I love about it is this. We’re not like we’re not always just talking about project management. We’ve covered a number of different topics. We had a great talk on Web accessibility. We had a really cool talk on, you know, analytics and measurement. And this the woman who presented she showed us all of these really cool, like Google’s data studio dashboards that she creates and like why she’s choosing these metrics for measuring success. So, like, there’s a really good opportunity there to learn about, like, again, all things digital, all things technology and to to help scale yourself up. So, like, if it’s the Boston group or if it’s some other Meetup group or maybe it’s like, I don’t know, you want to join a Drupal Meetup group or something like that so you can learn a little bit about the tools and the platforms that your team is using on a day to day basis. And I think that’s a great opportunity to kind of skill up.

Galen Low

I really like that sort of notion of getting outside your comfort zone to kind of immerse yourself in some of the peripheral things that we need to know as digital project managers, like a Drupal Meetup group like I think that’s a fantastic idea.

Galen Low

You know, one sort of last and final question. When do you know it’s just not the right fit? You know, you’ve made a bit of a mis-hire. How do you know and what kind of drives your decision to part ways with team members?

Matthew O’Bryant

It is not an easy thing. And it’s a good question.

Matthew O’Bryant

I mean, I feel like I was probably I wait too long on this one because, you know, we’re all trying to be the eternal optimist. But honestly, just when I see somebody not able to to to to grow somebody who is not kind of leveling up on a skills from a skills perspective on the technology side of things, you know, we want people to be a little bit more technical on the PM side. Right. And so it made me think of this really great post I read from Patrice Embry about being the one who being the one who takes, you know, are you a note-taker, basically. And you know what? What I got out of it was that you don’t as a PM, you’re more than that, right? Is she compared like a project manager with like an admin or an administrative assistant? Right. You know, the admin is there’s nothing wrong with being an admin. Right. But setting meetings, you know, sending out agendas, taking notes, distributing meeting notes, and so on. And so. We’re looking for more than just happens, right, so be more than that. Just don’t just be the one who takes the notes, be somebody who drives and leads the conversation. And if you’re unable to do that within a reasonable amount of time and you’re probably not the right fit at all, and that’s OK, just you’re just not the right fit for us. And so we’re going to have to let you go. It’s a challenge now more than ever because in the past, most of our organization was improvidence. We’ve since started hiring and become more of a distributed company. But in the past, it was easy to just, like, pop into a computer and be like, I’m auditing your class today. Right. Like, I’m just going to sit down and listen to you and see how you do. I can’t do that anymore unless I just like very conspicuously show up on a Zoom meeting. And then people are like, who’s this guy that we’ve never met before? Right. In which case, it’s difficult to see how the PM’s are doing. So that’s where I need to rely upon feedback from other people, because, again, I’m not working on these projects or I literally do need to just schedule sometimes to just be like, hey, I just jumping in and just wanted to say hi and introduce myself to you, clients, for no reason in particular.

Matthew O’Bryant

So that has made this a bit more challenging.

Matthew O’Bryant

So note to people, if you work at Zoom, please find a way to allow people to do anonymous listening.

Matthew O’Bryant

I know that sounds terrible. It sounds horrible, but you’re killing my ability to manage people remotely.

Galen Low

One of the things that’s missing from that virtual experience, which is in and of itself a whole nother topic for sure. Listen, Matt, these insights, these insights on hiring strong victims that can grow into becoming great project leaders are all really, really super valuable. What advice would you give to a hiring manager who’s just starting to write a job description for a role?

Matthew O’Bryant

Know what’s most important to you and to your team? You know, I mean, is it a platform like is that the most important thing? I mean, is it not the platform? Is it more about your notetaking skills? You know, just. No, no. What’s most important to you and what’s going to be most important to the other team members know maybe ask them like talk to your developers, talk to your designers, you know, ask them what are the things that would make their lives easier? Not that like that’s our job to make people’s lives easier kind of is, I guess. Right? I mean, just get their feedback, get their buy in. And the other thing that I would say is, if possible, try to involve them in the hiring process, if you can, you know, like even not saying that, like, you have to have them beyond the screenings or like in the interviews or whatnot. But like, if you think you might make a higher and it’s going to be somebody that people are working with, why not just let them talk to this person, do a quick intro and just ask them, hey, what do you think of that person? You know, I don’t know. I just think that’s it’s a way to show respect for your other team members and stuff. Yeah.

Galen Low

100 percent. I mean, yeah, they’re going to be working with them. How about for job seekers?

Galen Low

So for job seekers looking for digital project management roles, what’s the most important thing to remember when you’re positioning your skills, technical or otherwise?

Matthew O’Bryant

Yeah, if you don’t know it, don’t make it up. Definitely.

Matthew O’Bryant

And it again, like, I think it don’t just again if you cannot, not just say that you do things, but show that you’ve been able to do things, those accomplishments, statements that we talked about, you know, I think that is really going to help the hiring managers see you as somebody that stands out as different. Like don’t just say that you worked on a WordPress project. Don’t just say that you built the project and some details in there that are going to make it seem like it’s a little bit impressive, like somebody so that somebody is going to say, OK, well, yeah, that’s pretty complex. Like, that’s really cool. You must have to be fairly technical and skilled to have been able to manage a project like that. So, yeah, I think I think that’s what I would say.

Galen Low

Listen, Matt, thanks so much for joining us today.

Galen Low

It’s been great having you on the show. I really appreciate it.

Matthew O’Bryant

It’s been awesome being with you. Thank you so much for having me and chatting. And if anybody hears this and they want to connect and chat me up a little bit more, reach out to me and I’d love to talk more about this topic.

Galen Low

So what do you guys think? What are your hack’s tips and tricks for seeking out good talent? What works? What doesn’t? If you’re a job seeker, what do you wish hiring managers would say that they never, ever say?

Tell us a story. What was the impact of hiring the wrong candidate for a technical? What jobs have you interviewed for that really put you through the ringer when it came to technical knowledge?

Let us know in the comments below. And if you want to learn more and get ahead in your work, come and join our tribe with DPM Membership head to thedigitalprojectmanager.com/membership to get access to our expert’s forum, mastermind mentorship groups, workshops, live mentorship sessions, templates, and more. And if you like what you heard today, please describe or stay in touch at thedigitalprojectmanager.com. And until next time. Thanks for listening.

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Galen Low

Galen Low

I am a Client Services Professional and Agile Delivery Specialist with progressive experience driving human-centered digital transformation in government, healthcare, transit, and retail verticals. I manage large, cross-functional teams and executive-level relationships within boutique agencies and large consultancies to drive tangible business outcomes and strategic growth. A few of my specialties: digital strategy, agile web application development, project management, human-centered design, design thinking, innovation & growth, digital government, career coaching, professional development.

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