How to Navigate the Delicate Art of Not Knowing Everything as a Technical PM

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Galen Low: SaaS. SOC2. ADA. Jenkins. You thought they were lyrics to a Charlie XCX song. Turns out, they're not. And by the look on your client's face, you probably should have known that — or at least known someone on your team who knows that. But before you hang up your spurs and abandon your dream of becoming a respected leader in technical project management, keep listening.

We're going to be exploring how technical you need to be as a technical PM in 2025 — and how team leaders can support and develop high impact PMs without sending them to get their doctorate in DevOps.

Hey folks, thanks for tuning in. My name is Galen Low with The Digital Project Manager. We're 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 on over to thedpm.com/membership.

Okay, today we are talking about guiding, mentoring, and leading a team of technical project managers to find that right balance between technical skills and people skills and help them advance their professional growth within an environment where they need to know enough but simply can't know everything about the technologies that their teams are working with.

With me today is Kayla Keizer, Team Lead and Senior Technical Project Manager at Plank, a digital agency specializing in web and IT projects for clients in arts and culture, non profit, and education.

Kay, thanks so much for being here today.

Kayla Keizer: Thanks for inviting me.

Galen Low: I narrowly missed your like Costa Rica background. You got back from Costa Rica today, yesterday?

Kayla Keizer: Today, this morning.

Galen Low: I was so excited. I misscheduled this because we could have had, a jungle or a beach in the background.

Kayla Keizer: Yeah, it would have been. It's still green behind me, but it would have been like actual nature behind me, the jungle.

Galen Low: If you're listening to this podcast and not watching it, just imagine wonderful nature behind Kay right now.

I thought maybe we could just dive right in and start with the question that everyone wants to know the answer to, which I think is, can you continue to advance as a technical project manager without having technical training? Or are you going to hit a wall if you're a technical PM who like can't debug Python or like wrangle Git or navigate Laravel or configure a CDN in AWS?

What are your thoughts there?

Kayla Keizer: My thoughts are you are part of a team of technical experts who at the end of the day it is their job to debug. And configure AWS so it definitely doesn't fall on you to do the actual step by step work, but it's always good to understand or have a base knowledge of the concept.

If someone mentions Python to you and you have no idea what it is not great and that's not something that's you have to go to school for, or you need to be specially trained, you can Google and get a good understanding or base. You can ask your team members, Hey, do you mind spending a little bit more time and giving me a bit more context on this so that I'm prepared better when we're talking about this or when we're writing up requirements, I can give you the info we need.

That's really the information you need to know is understanding the concepts and also understanding, okay, what questions do I need to ask in order to give the development team or the designer or the content team, whatever information they need to actually do the thing.

Galen Low: Boom. I love that. I love that it's not, you must know everything and go get formal training for it. But like the art is actually asking the right question, having the wherewithal to ask, and then also asking the right questions so that, you can be that translator, that conduit for some of this information to like transfer between your team and your stakeholders, and I think it's so cool.

I wonder if we could zoom out a bit because Earlier in your career, you found yourself in a technical project management role. And I think, don't let me put words in your mouth, but I think it was at a time when you didn't feel all that technical yourself and it was like serious technical. You and I were talking in the green room.

It was like telecom, which is full of acronyms, full of technologies, full of all these concepts that are pretty specific to that industry. And now you've taken that and you've, let it run its course or you followed that path and you now lead a team of technical project managers at Plank.

What was the first big hurdle that you faced as a non technical project manager leading a project team of like technical specialists and how did you overcome it?

Kayla Keizer: I think you have to overcome yourself a little bit. Like you said, I was in deep, I was working with people who have been in the company for 10, 15, even 20 years.

who had not just the technical expertise, but a history and a background of the foundation of the network. I was a coordinator at that time, and I was also working closely with the director. And so I was helping him a lot. Again, I'm working with the director, 25 year olds. knew what this trying to figure it all out.

But the thing for me that helped me get through it is you can't shy away from stuff. You have to get over yourself a little bit. And yes, it's scary. And yes, you don't. know, but you won't know until you ask the questions, until you dive deep into it and you embrace the challenge. I find when you embrace things, it starts to go a lot more smoothly than when you're like, Oh, this is so crap.

I don't want to do this. And you procrastinate it. And you're like, not sure. And if you put all of that negative energy to it, it's always going to feel tough. And it's always going to feel like you're in the mud trying to get out of it. So I think really it's mindset and it's making sure that you fake the confidence if you have to.

Galen Low: I like the idea that, we so often create our own barriers by getting in our own heads. Whereas actually the thing that moves it forward is just like having that mindset of, you know what, I got to do this and yeah, maybe faking it a little, but faking it from a standpoint of being confident enough to ask even right now, just being confident and lying to yourself that you do know this stuff.

But like actually figuring out again, to your point, what to ask.

Kayla Keizer: And confidently asking questions, you're not in the background. You're not timid. You're not coming to whoever you need to ask the question with fear and anxiety, because they're going to pick up on that. If you're in a client meeting, the client is going to zoom in and know that you're not confident about what you're talking about.

So that's what I mean when I say like fake, the confidence is even if you don't know, it's okay, but at least be. upfront, be honest and be confident because people tend to zoom in or they lose confidence if they feel like, Oh, they're not even confident in themselves. So how can I have confidence in them?

So that's what I mean. And I think to circle back to like, how do you get over it? Once you've get over your mental barriers, you have to lean on like your strengths. My strength was. I'm really good at documentation. I'm really good at understanding technical information when it's explained to me and then taking that and turning it to a client or being able to write a ticket or be able to do requirements.

You don't need to be technical in order to document and ask questions.

Galen Low: Now I really like that because like even when you think of it as like a literal translator role, you're like whatever United Nations General Assembly and like you're doing a translation doesn't mean you have to know how to lead a country.

But your skill, right? The thing that you want people to have trust in you about is making that message land in a different language on the other side. And I think that's it's such a strong and valuable role in the tech world and the IT world and the digital world where, that is what you want people to build trust in you for.

Not your ability to code or debug or deploy software, but knowing how it's done and being able to at least drive that conversation and orchestrate everything so that it does get done in a meaningful and competent way.

Kayla Keizer: Yeah.

Galen Low: Can I put you on the spot?

Kayla Keizer: What?

Galen Low: Can I ask you what you feel your scariest "dumb" question was to ask in the world of telecommunications?

Kayla Keizer: I don't know if there was one specific question, but I will admit to not asking enough questions in the beginning. And I maybe over assumed my skills.

Galen Low: Okay, yeah. Faking it real hard.

Kayla Keizer: Yeah, and they asked me for some sort of report. And I went and I made the report to the best of my capabilities, didn't ask any extra questions, didn't ask how they wanted it, what data.

I was just like, yeah, no, I can do that. Did the report, gave it to the director and he was like, no, this is not what I asked for. I was like, oh, and he asked, why didn't you ask me more like qualifying questions if you weren't sure? And I was like, oh. I guess I could have.

Galen Low: First of all, I applaud that because it's pretty bold. And you're coming at it from this mindset of actually, I do know what to do. And yeah, maybe it didn't hit the mark, but I think that's actually, in terms of not getting stuck in your head and like going and doing a thing. Sure. It wasn't perfect, but I think that's actually it's a pretty bold mindset to have.

Entering an industry and being new in that role ish to feel like, yeah, I got this, but in fairness, qualifying questions, clarifying questions, yeah, never a bad thing to ask when you're in that environment where things are done a certain way in some of these industries.

Kayla Keizer: And it was expected to ask questions. People expect you to ask more defining questions. And so for me, it was a huge learning. Like now I'm like ask, ask.

Galen Low: Now it's yeah, now it's the brand actually, and it's yeah, I like that as a cornerstone, like of your approach really is that, not only can you not know everything, But you probably don't know most things in a certain way, shape, or form, right?

I'm not insulting anyone's intelligence who's listening or watching, but there's just so much to know. Like, how can anyone know everything? The value is finding out. I did a film studies major in school. I joke that I like, didn't really learn anything. of value, but I did certainly learn how to deal with people and collaborate and how to find an answer if I didn't know the answer and then how to craft that into a thought that I could mobilize into action.

And, I think not just folks who went to university, but like anyone, right? That's like that skill that is worthwhile to hone in this day and age, just because honestly, there's too much to know.

Kayla Keizer: And you hit on a very important point. I think sometimes we underestimate our soft skills.

And if the organization wanted a technical PM with, an engineering background, they would have hired that person. If you're a non technical project manager in a technical role, it's probably because you have that strong personable skills. You are organized, they see you, the value outside of the technical expertise that you bring, you're able to talk to clients, you're able to talk to the team, you're able to motivate the team, which is super important as a project manager, being able to motivate and lead without having direct managerial authority.

Galen Low: I think it's a hugely good point because in a lot of the conversations I have with folks in my community. It's almost the framing is what don't I have, what skills don't I have that like I need to get to become a technical project manager and not enough emphasis on okay, if you're even considering that role, yeah, there's some of these soft skills that you'd likely have and could probably still hone further, that's actually the meaty bit of the role, that leadership role, that communication role.

Kayla Keizer: Yeah. And I have to say, I just finished hiring. And one of the things that I was looking for is people who were able to explain how they went about finding information and who were able to explain how they were able to, because I asked, I was looking for a technical leaning project manager and I asked the question What's your methodology to approach learning new concepts and they were able to respond and say that how they were going to find the information and that is valuable like you don't need to know but if you have a method, and you're able to explain your method of finding the information.

That's like gold.

Galen Low: What is your sort of favorite response to that? And or maybe even just your approach to like finding answers, especially when like you and your team, you deal with like projects that relate to cyber security and data and privacy accessibility. What is a good answer to that question in terms of like, how do you approach finding out an answer to something you don't know?

Kayla Keizer: I always am very curious and I always try to do my own research myself as a first step just to get definitions at the very least. Be able to know the terms, right? And then I'm a very in person, so I'll figure out who's the expert on the team, and then I'll ask that person, Hey, do you want to sit down with me for 30 minutes just to run through a couple of things and maybe can you help me so that when we're in the next client meeting or when I'm writing the next task for you, I know exactly what you're looking for.

And of course, they're going to want to take time because you're positioning it as how can I be better so I help you in the end, right? That's the value prop for them. For me, that's what's worked is, do a little bit of research yourself and get the experts to help you out. And you don't need to watch 30 hours of YouTube videos.

Galen Low: That's what's nice, right? Because I know some folks who are like, I need to learn, whatever, cybersecurity, as an example. And they're like borderline, like they could probably do a SOC2 compliance audit. And I was like, I think you went too far, right? Whereas I think like your model, what I really like is a, it's very practical, right?

Like in terms of a case by case basis, as a project person, you haven't got 30 hours to sit down and watch YouTube, but it is that sort of a very powerful educational model where it's yeah, read some stuff on your own, be curious on your own and talk to somebody who knows. And then I love that nuance of and there's something in it for them, right?

It's not just you can use it strategically as well to build trust with your team because you're curious about what they do. And frankly, project managers. Even technical ones, I have a bad reputation of being like, just, cracking the whip. I don't care what has to get done, you have to get it done by this date.

Don't talk to me about all these acronyms. To come in and be like, can you tell me what this acronym is? Because it's gonna help me. And then, it's gonna help you. I think it's a very powerful sort of value proposition as well.

Kayla Keizer: Yeah, because it's not just building relationships with clients, but it's building relationship with the team too. Spot on that.

Galen Low: It's yeah, it's feed two birds with one scone, to use a PETA metaphor.

You said something earlier that I thought we could dive into. It was just not just offline with your team to prepare for a meeting, but sometimes In real time, in a meeting with the client, and I'm just curious you're leading a team of technical PMs, what do you advise them to do if they get asked a technical question by a client or a team member, but like in that real time situation and they don't know the answer to it?

Kayla Keizer: I always tell them it's okay to say you don't know the answer. But I make sure that they know who has the answer. So it's important, and this comes back to understanding the concepts and understanding who does what on the team, what's a front end issue, what's a back end issue, what's an SEO issue.

So when the client asks something and you might not know, you can say, you know what, I don't know. My X, Y, and Z person on my team has the information. I'll take that down right now, and probably in the next 24 hours, I'll get you an answer. Don't worry, that shows a lot of confidence. They have a time frame of when they're going to get the information and they know who has the information.

So why would they get butthurt that you don't have the answer right in that moment?

Galen Low: And highlights the value of your role, actually, which is a, again, you can use it as this like combo punch, right? You're like. I don't know the answer, but I know how everything works here. Cause I know the team and I know who to ask because I did understand your question.

I just don't know the answer to it. And then my job is to actually plug you into that answer. That's part of what I'm doing here is translating that for you. So let me go, and get that and also not perpetuate. Any preconceived notions that you are more technical or are the Oracle for all the things?

Because it sets a weird expectation in terms of what your role is. Don't get me wrong. I don't know. Do you have anyone on your team who like was an engineer developer or someone who was actually came more from that technical background into project management instead of the opposite?

Kayla Keizer: Not really. We do have some that dabble, but they're very headstrong into their lane of being a developer and technical experience. But I feel like if you're the opposite and you come from an engineering background and you come into the project manager realm, you could get into the trap of not asking enough questions and assuming the requirements because you have too much knowledge, almost right, and so you inadvertently steer the client or you steer the project in a direction that maybe it shouldn't have gone. Because you've made an assumption instead of asking a question. So I do think there can be challenges and pitfalls having that technical background and trying to transition into the project management role.

I sometimes catch myself doing it because I'm at a point now I know enough to be dangerous. And so sometimes I'll even try and without even realizing asking a question that's steering in a direction and then, one of the teammates there on the call and they'll be like, Oh no, we shouldn't be saying it like that.

This is how we should ask. And I was like, Oh, okay. Yeah. All right.

Galen Low: That's such an interesting spin on it though, because that's where the rabbit hole goes, or at least. The typical path coming from project management side into sort of a more technical project manager role is you start knowing basically nothing and feeling Like you're an imposter, you don't have the confidence, or feel like you're missing something.

And then journeying to the point where you're like, actually, I've learned a lot. And yeah, I think I know the answer now. And sometimes that might not be the right way to approach it. Knowing enough to be dangerous, it actually ends up being a problem in some ways.

Kayla Keizer: Yeah.

Galen Low: How do you approach catching yourself on that? Where you're like, I think I know the answer, but I probably shouldn't answer because I think this person should answer or I should get the answer from them.

Kayla Keizer: For me, it's when I need to give more of a description or more of a detailed answer. So all, no, okay, no, what you're asking for is bad UX.

I can't tell you why it's bad UX, but I know that it's bad UX. So in that moment, I'm like, okay, I need to ask or get one of the team members involved. Cause I can't give it more than a yes or no answer at this point.

Galen Low: I love that approach. It's I have an opinion. I can give you a yes and no answer, but I can't explain why. Okay. Yeah. I'm going to hand that one off.

Kayla Keizer: Exactly.

Galen Low: We've been covering some of this in terms of like soft skills, but I thought it, maybe I just posed a question anyways, just in your opinion, is a technically trained project manager possibly better at the technical PM role than a non technical PM in terms of coming at it that direction?

But mostly, I think what I need to ask is like, when a project manager is not technical, what is the value that they are bringing to the table? And maybe we do a reframe, because I know we've been talking about soft skills and things like that, but like, how would you frame that if you were trying to get a job as a technical project manager, but you don't have all of these platform certifications and know all the acronyms and, and.

Kayla Keizer: I think if you are in an interview, I think you have to do your due diligence and understand the industry and the technology that company is working with. So that even if you don't have a deep understanding, again, you've done your due diligence, you've gone and done a little bit of research and prepared, and you're able to talk at least high level about certain concepts.

And you can talk again about how you'd be able to. go deeper or how you would be able to approach learning more so that you could help facilitate the team even more than that. I know for myself, it's also been helpful being able to follow process, like we were talking about soft skills and whatnot, but Being a project manager, you're bringing also structure to the project.

We see it all of the time. There are no project managers involved and everything goes everywhere and nothing gets done. So being a champion of process and understanding the different gates to get from A to B to the end of the project and be able to launch, that is a huge quality that we forget that we have.

We are the driver of the project. Even if we're not technical, we're still able to move the project forward.

Galen Low: I love that. Yeah, like the value is we give structure and you raise a good point. Like earlier on, it's if you're in an interview for a technical PM role. They would have just called it a PM role if they didn't expect some level of understanding.

So do your homework. Don't just assume that you can be like, I'm good with people. And that's probably perfect for this role because there is some intent behind it to actually give it that title of technical project manager. There is a level of expectation. It's good practice to do that due diligence going into an interview, because guess what?

That's probably what you'll be doing like in your job too, right? Like doing a bit of, the K approach, just like reading up, getting smart, talking to somebody who's smarter, then off to the races.

Kayla Keizer: Yeah.

Galen Low: Maybe I'll round out with this. We've been talking about technical project management, and I think we've landed in a zone where.

Yeah, you have to be curious, but you don't have to be necessarily a developer. You don't necessarily have to be deeply technical yourself. But if you had someone on your team, or if you knew someone who was a project manager, debating whether to deepen their specialization as a technical project manager.

In other words, they're actually hungry to learn more. What advice would you give to them? Would you advise that maybe they pursue some of these certifications like AWS or maybe take that web development course? Or would you view it as maybe sending them down the wrong path?

Kayla Keizer: I think if they are evaluating that, I think they should evaluate where they want to take their career and in what alley.

For example, if you are really into security, then definitely get some web security certificates, really brush up on that so that you're able to talk to that and understand the concepts. If you're really into accessibility and championing accessibility, understand what the core principles are about accessibility and how to go about it.

We don't code. At least I don't know any project managers that code, so you don't need to code. But if you are looking to go into a specific industry, there might be certificates that you can get for a specific industry to be able to brush up on so that you can bring that into an interview.

Galen Low: Yeah, I love that because also sometimes I forget we're talking about specialization is about specificity. Do you know what I mean? And I think as you're talking to Oh yeah, like maybe the wrong thing to do would be to have a hundred specializations because then you're like, what is it that you do? But whereas if you like had one deep niche that you were deeply passionate about that you're interested in, like cybersecurity is the thing that I enjoy, I am passionate about project management and cybersecurity.

And yeah, when you would ever hire me or promote me into a role, this is what you're getting, because I have both versus just like specializing in too many things. To look too much like a Jack of all trades and quote unquote, that overqualified sort of response that you get, yeah, you look a bit, I don't know, overqualified and really what they mean is it doesn't look like you can decide what it is you do or communicate to me what it is that you do that makes you special and different.

Kayla Keizer: And I think people don't realize how many directions you can go with the web with internet and technology this day and age. I was in telecom, there's people who are project managers in telecom and that's what they do and they understand the hardware and they understand how to set up a network and that's their specialization.

So if you're looking to specialize, figure out what industry you want to be in cyber security, telecom, web development, there's so many different niches, and there's a lot of opportunity.

Galen Low: I love that.

Maybe I'll tie it all the way back to the beginning because we're talking about like leading and mentoring a team of technical PMs. And a lot of this kind of each individual team member will learn some of these things on the fly. Do you have a mechanism at Plank or like a community to practice where you can share some of the learnings on the go between project managers?

Kayla Keizer: Yeah, so I meet with my team like once a week and we review stuff, but I also have like once a month we meet all of us.

And we talk about challenges and we talk about like project progress, we talk about process. And we also have, a private Slack channel where we can air our grievances. But that's how we communicate together. I actually been using a lot of the DPM. I've been going along through it with one of my employees, just to give them a more base or more information in a different way.

You do the PMP certification or the CMPM certification and then especially in digital, you get to web development and you don't even understand how it translates. So having that extra bit of content to be able to translate basically principles into actionable items. Is very value.

Galen Low: So glad that you're using it. Thank you for that. But you're right. There's so many places to go in the web. And it's it would be unreasonable in some ways to like, Assume that an organization like the project management Institute could create the perfect thing. That's going to answer all the world's questions.

We started this as, you can't know everything. And I think that's actually a lovely poetic place to land where it's like. Cool. Yeah, deepen where you have passion, where you have interest, where you have curiosity, understand the world that you operate within and, ask questions, stay curious.

Kayla Keizer: And I think it's important to acknowledge where you are too, right? If you're just starting out. You're just starting out. No one is expecting you to be 10 years in day one, and it's okay. Don't feel like an imposter. Don't have that nervousness. Acknowledge where you are and people will meet you where you are.

I think that's one of the things that I remind my team multiple times when they feel like they should have known something. You are where you are today. And in 10 years or in five years, you're going to be in a different space and the expectations are going to be different.

Galen Low: I love that. That's such solid advice.

Kay, thank you so much for spending the time with me today. I've had so much fun.

Kayla Keizer: Awesome. Thanks for inviting me.

Galen Low: Yeah, it's a pleasure. It's a pleasure.

All right folks, there you have it. As always, if you'd like to join the conversation with over a thousand like-minded project management champions, come join our collective! Head on over to thedpm.com/membership to learn more. And if you like what you heard today, please subscribe and stay in touch on thedigitalprojectmanager.com. Until next time, thanks for listening.