The Management Career Path with Tera Simon

"One of the biggest things that you learn being a PM is how to have difficult conversations."

It seems like the natural project management career would lead to people management. But why? Managing projects is a far cry from managing people. And doing both at the same time? That sounds like madness. But people do it every day. In fact, this week’s guest is one of those people. Tera Simon works at Globant where she leads projects and project managers, among other things. In this episode of Time Limit, Tera and Brett discuss:

  • Why people want to be managers
  • The challenges of managing people
  • Resources for new managers
  • What it’s like to manage project managers

Resources mentioned in this episode:

About our guest


Tera Simon
Delivery Director, Globant

Tera is a Delivery Director for Globant, a digitally native company that leverages the latest digital and cognitive technologies and methodologies to transform organizations in every aspect. Along with working at Globant, Tera is a professional speaker who speaks on leadership, confidence/empowerment and technology.

Tera has been recognized for having a passion for discovery and serving as the integrator of operations and client expectations, as well as the true hub for all project-related information within the organization. Tera has helped define, document and implement process within numerous businesses.

When Tera is not sprinting from meeting to meeting, you can find her supporting local breweries, traveling, and educating anyone that will listen on why football is the greatest sport around.

Follow her at @tcaldsimon on Twitter.

Episode Transcript


Brett Harned:       Hey, welcome to Time Limit. Thanks so much for listening.If you're looking at the management career path, or maybe are a new manager, you're really going to like this episode. I asked my friend Tera Simon, who's a delivery director at Globant, a digitally native company in Raleigh, to join me on Time Limit today. Tera oversees a team of PMs. She manages her own projects and then contributes to the organization as a director. Her plate is totally full and she's really good at what she does, which means she's got lots of opinions to share on leveling up from managing projects to managing project managers. Check it out.

Brett Harned:       Hey Tera, thanks so much for joining me Time Limit. How are you doing?

Tera Simon:         I'm good. How are you?

Brett Harned:       Awesome. Thanks for joining me bright and early today. I really appreciate it. For everybody who's listening it's 9 AM.

Brett Harned:       Tera, when we first met I think you were a digital PM in an agency, and now you're a delivery director for Globant, and that means that you're not only managing projects now, you're also managing people, and probably a whole lot of other things, right?

Tera Simon:         Yep. It's sometimes just a little bit of chaos every single day, but you know what, that's makes life exciting, right? Every day, you walk into the office it's something completely different.

Brett Harned:       So true. I like that part of the job. That's definitely part of the project management job.

Brett Harned:       So let's kick it off with a little bit of a challenging question because I want to keep you on your toes bright and early. I kind of have this theory that not all project managers really want to actually be managers, but they kind of feel like they have to at some point. And I'm thinking that you probably did want to be a manager just because I know you, but I'm interested to know why. Like what are the things that drive you, and maybe even other people to want to take on more management responsibility?

Tera Simon:         I definitely agree with the whole fact that I don't think everyone necessarily wants to go into management. Sometimes I think that for project managers, because you have the word manager in your title, you automatically think, "Well that's the path, or the direction that I want to go, or that I'm supposed to go." For me, I have always loved be able to coach and help other project managers, or even just other team members grow into a role, and that's where like ... For me, I thought, "Okay, this makes sense. This is why management seems like something that I would want to do."

Tera Simon:         I also know for me, there was a lot more to it than just like, "Okay, I'm going to be this mentor for this person." Or, "I have the ability to help shape someone else's career." Or, let them know about mistakes that I've made in the same position that they're in and like how I would have done things differently and kind of worked them through that.

Tera Simon:         But, the other side of the management piece that is difficult, and sometimes the stuff that people don't talk about but like I actually love, is when you start to think about the operational side of things. Right? Like you are now the one that's like you have to do all the hiring for the teams that are coming in, and you're in charge of their salary, and their growth. Then, you're also, especially if you work in a smaller company, you're also part of the group that is trying to help bring in new business for the company, and you're kind of responsible for all of these people, and it's a lot of pressure, but it's also a lot of fun at the same time. But maybe I'm just weird.

Brett Harned:       No, I totally agree. And I think ... That's why I said there's probably a whole lot of other things that you're doing because depending on where you work, that title of manager or PMO even, can be kind of a job where a lot of stuff just gets dumped on you because they need your expertise, but your team needs you and sometimes they want you to take on higher profile clients, and things like that.

Brett Harned:       So I'm really interested to kind of dig in on that and talk about like in your experience as a manager, also a project manager, or client services at the same time, what do you see as kind of the biggest differences between being a PM and then being just the manager, or not just the manager, but being a manager?

Tera Simon:         When you're a project manager you're still already kind of doing a little bit, like a very small sliver of being a people manager, right? Because you're the one that's like managing the team and making sure that everyone is kind of staying on task and that you're getting things done the way that it needs to get done.

Tera Simon:         But from a project manager perspective your responsibility is to the project, and to the client that you're working on. And we all know project managers do not have the luxury of only working with one project, and one client at any given time. But, you do know that your day-to-day, even though you may be working on 20 different accounts, or 20 different projects, your day-to-day of the actual task that you're doing, always kind of stays consistent, right? It's always about moving the team forward, moving the project forward, having difficult conversations, keeping up where everything is from a deliverable and from a budget perspective. You kind of get to just hone in on being the best at that when you're a project manager.

Tera Simon:         When you move into more of a leadership role, what you start to realize is that you lose some of that control. Like the control that you're used to having from being a project manager because you know what your timeline is, you know what your project plan is, you are the one that isn't control how that pivots and how that changes.

Tera Simon:         When you're in a leadership position, and by leadership I mean when you're like a people manager, or you're running PMO, you don't have that control. You have other people that are asking you to do different things, and what you may have done that is your opinion of how you think it could actually help better a group, or better a team, will sometimes get overwritten, and you start to lose a little bit of that where you feel like you have a true level of ownership.

Brett Harned:       Yeah. I feel that so hard. I remember managing PMs and thinking, "Oh, I wish I could just be in the room for this conversation because I think it would go a different way." Or, "I wish I could actually hand-hold you through some things to teach you to be a little bit better." But I think there's a point where you kind of ... when you make that transition, you recognize that you're moving onto that kind of coaching position because you're good at what you do.

Brett Harned:       And I say hello to your dog in the background.

Tera Simon:         Sorry. He's saying hi to the mailman.

Brett Harned:       But I think what's cool is that you learn a lot as a PM that allows you to kind of grow up into more of a management role, but what are your thoughts on that. How does being a PM kind of prepare you for management?

Tera Simon:         So I definitely think one of the biggest things that you learn from being a project manager when you're trying to go into people management, is how to have difficult conversations. That is probably, even as a new, like an early PM, that is probably that first moment where you have that feeling of dread when you're like, "Oh goodness, I have to now tell a client that we're not going to hit this deadline." Or, "We completely under scoped something." And they're going to be mad at me. This is not going to be easy to do, but I have to do it.

Tera Simon:         Once you have that first difficult conversation, it just makes it so easy to do ... like going forward. In people management, your difficult conversations come to a whole new level because now it's not just having to have those hard conversations with clients, but it's also having to have those hard conversations with the people that you are directly responsible for.

Brett Harned:       Yeah.

Tera Simon:         So to me, that's like one of the biggest things from a project manager perspective that I feel like you learn going into what makes you ... to have the ability to become a good people manager.

Brett Harned:       Yeah. I mean, I think what you're saying is like as a PM, you basically have to build really good soft skills, and then you use those skills as a manager in different ways, but it's really similar.

Tera Simon:         Yeah. And that's the thing is like you know, no one can teach a person how to have soft skills, right?

Brett Harned:       Right. Right.

Tera Simon:         Like you can ... every day, all day long we can teach hard skills. We can teach the traditional things that you would need to know to like be good at your job, from like a, "Here's how you manage financials." Right?

Brett Harned:       Mm-hmm (affirmative).

Tera Simon:         I can break that down for you. This is what a margin is, and this is what a P&L is, and this is why this can't drop this way, but I can't teach you how to have empathy for someone. That is a soft skill that you have to learn on your own.

Brett Harned:       Totally.

Brett Harned:       What are the things that you kind of wish that you'd known when you took on management role as a people manager?

Tera Simon:         Even ... goodness, there's so many different things. I wish that there was more formal training for people that are going into leadership and going into management. It's one of those things where like a lot of times people aren't really even asked if that's the direction that they want to go, especially if you're a project manager, it's just kind of like assumed that, "Well, you're so good at managing teams, that well here you go. I'm going to move you into this management role." And you have no training around it.

Tera Simon:         So I wish I would have had more formal training. I also wish that someone would have told me how difficult it really can be to manage people. What I mean by that is a lot of times, especially if you are going into a management role when you've been a peer, like you've been on the same team as all the other project managers, and now you're being asked to be their boss. You have to pivot a switch in your mind, right? You're now no longer going to be hanging out gossiping by the water cooler with them all the time, and you're not in the trenches with them anymore.

Tera Simon:         So you kind of feel like you lose a little bit of that friendship that you have built and you're now having to step into a completely different role, and that's really hard.

Brett Harned:       Absolutely. I've seen that. I've seen people, not even in project manager positions, but you know like production positions, like development, someone getting basically elevated to a management level with no training, no preparation. They step into it and they realize, "Wow, this isn't really what I wanted all along. I want the camaraderie and the good vibes between my kind of co-workers. I don't want to have to manage them." Just because you're the best person in the company at that thing, doesn't mean that you're the best person to manage all of them either.

Tera Simon:         Right. Then it's like what do you do? Do you take a step back, or ... for some, and I know I have thought it before too, especially when I first went into people management. I was like, "Am I a quitter? Am I giving up if I take a step back and not want to do this?"

Brett Harned:       Right.

Tera Simon:         And that's a really hard thing to kind of look at for yourself as well is like you've got to do what's best for you and for your career, and if you're not happy in a position that you were placed into, then you have to speak up about it. But at the same time, if it is something that you want to do, and you're not speaking up about that either, then you're not doing yourself any good either. You know?

Brett Harned:       Yeah, that's a really good point. It can be a little bit of a trap because you end up making a little bit more money, you feel like you're a little bit further along in your career, and then you step into it and maybe it's not what you want. I think you're right. You have to do what's going to make you happy. I think that's kind of the best advice that I've received in my career is like follow happiness.

Tera Simon:         Exactly.

Brett Harned:       You mentioned you wished that you had some kind of training before going into that role. I'm wondering if you've done any training since? If there's any books that you've read, or coaching that you've done? Like resources that you found to help other people level up. Do you have any kind of tips there, or recommendations?

Tera Simon:         Yeah. The biggest thing that I kind of found, especially after I started into people management at an earlier stage, there wasn't a lot out there. Sure there's some of those How To Be a Leader for Dummy books, you know what I mean? But like a lot of those are kind of more focused in on a set type of people management. Right? Or like you can also read books on the five languages of love, and trying to understand how to maneuver around different personality types, and this is how you can be a better leader.

Tera Simon:         There's just different like ... I always think of them as more as being like self-help books, and I'm like, "That's not exactly what I was looking for." So, the first thing that I kind of did was I found a mentor. To me, if you don't have a mentor, then find one for yourself. I chose a person that I actually at the time picked, was lucky enough to have the president of our company kind of serve as the mentor for me. That was probably one of the best decisions that I ever made.

Tera Simon:         He had come into, at the time at the tech agency that I was working for, he had come in after having been a CEO for several other companies, and had been in the business for 30 plus years and he had a lot of good just knowledge. And I learned a lot from him, which I think has helped make me a better leader.

Tera Simon:         Two of the biggest things that I still takeaway from meeting and working with him is one, is don't always be the person that is the loudest talker, or that says the most during a meeting. Instead, whenever you find yourself in like these really kind of tough or tense conversations and meetings, whether it be with your direct team, or whether it's with a client, sit back and take time to observe and listen because the person that speaks not as frequently, is the one that's most likely heard. I try and take that with me, especially when I ... as I've grown in my career.

Tera Simon:         The other thing is the first time I ever had to fire someone, which good gracious that was not fun, but the same ... he kind of gave the same type of advice with that, which is when you go and when you're having to let someone go, say as little as possible, just be direct, and then stop talking. That is like the hardest thing for me because I am the type of person that like I hate that weird, awkward silence, and then all I want to do is hug the person. And I'm like, "I can't. I have to just sit here and stare at you and make-"

Brett Harned:       Not appropriate.

Tera Simon:         I can't do anything. So, that like ... Find a mentor that's definitely one like big piece of advice I can give you. I've actually done leadership training since. The company that I work for now, they actually just introduced leadership training, which has been spectacular, and they started from the C-suite level and had everyone from the C-suite actually go through this leadership training first. Then they started to trickle it down to the VPs, and then the directors. Now, they're actually putting all of the ... anyone that's involved in delivery and operations. So they're actually about to put all of the project managers through it at the same time.

Brett Harned:       Oh wow, that's great.

Tera Simon:         Which is ... it's really cool. Then after ... so it's about like three full days of training. Right? But then afterward you get ... everyday you get additional information and different material for like 30 days after the training, then they regroup us six months later just to make sure like do we have any other questions. Things like that.

Tera Simon:         So, if your company offers any type of training like that, absolutely go and do it.

Brett Harned:       Yeah, I agree.

Brett Harned:       I want to kind of circle back to something that we mentioned earlier, which was kind of around managing PMs and I mentioned that I've managed them in the past so I kind of know what it's like. But, I'd love for you to kind of share some of the challenges that someone might experience when managing PMs, because PMs are the people who seemingly have it all together, right? So they shouldn't ... it almost feels like they shouldn't need a manager, but they clearly do. So what are the things that have been challenges for you in that realm?

Tera Simon:         I think if you run into the exact same challenges when you're managing PMs as you do as a PM managing a team. Because as a project manager, you naturally don't want to let anyone down, and you are constantly like ... you have like 10,000 plates that are all spinning at different times, and you're just trying to keep them all moving, right? And that is the biggest fault that we have as project managers because we're going ... everything something is going to drop, right?

Brett Harned:       Mm-hmm (affirmative).

Tera Simon:         But you don't want your manager to be disappointed in you because you dropped one of those plates. So that is one of the biggest challenges that I have found like from managing project managers, is that you almost have to like pull the information out of them to get them to admit them that they need help on something. Because you constantly, as a PM, want to feel like you have everything in control, and you sometimes just get blindsided by the bad, or the fallout that's going to happen.

Tera Simon:         So from a manager perspective, you have to be able to kind of see beyond the tree line for them and be like, "Okay well, I'm noticing this," and try and help get that information out of them. It's been one of the biggest challenges that I've found from like managing a project manager.

Brett Harned:       Yeah. I think that makes a ton of sense because you feel like you know something could wrong, they know what's going on, but you don't want to be blindsided, right?

Brett Harned:       What are the kind of like steps, or tactics, or do you do meetings, what are the types of things that you do to help to kind of manage your team to contain that, and to kind of get ahead of things, but also make the team on an individual level, but also on a team level, like make them feel supported by you?

Tera Simon:         Some of the things that we've implemented is we do a every other week team meeting, where the entire group gets together. They talk through where things are, just like a high level status of their projects, any hiccups that they're running into, or any advice that they need from the team. It gives me a chance to kind of go through like, "Here's some new things that I've seen." Or, "Has anyone tried this? Has anyone thought about that?"

Tera Simon:         From there, we also do ... I took three of our senior project managers and had them ... we basically created coaching circles. So, they each have three or four team members that are a part of their coaching circle. So they have the chance ... and they meet ... it's at the frequency of which they are able to do, but they typically try and get together once a week. Sometimes it's every other week, but they have those small coaching circles, then the leads from those will bring back any information to me.

Tera Simon:         That they'll like, "Hey ... " we'll regroup once a month and be like, "Hey, what are some of the trends that you're hearing in your coaching circles?" And something will come up of like, "You know, it seems like as a whole the team is struggling on like what's the best way that we could really be utilizing JIRA for our customers and like getting them in there?" So then we arrange a training for the entire group around here's JIRA and how can we be utilizing it better because that seems to be a trend that's happening.

Tera Simon:         I also do one-on-ones with every one of my team members, and I do those every other week as well. The biggest thing that I try and do when I'm doing a one-on-one is not always make it be directly about work. Spend enough time to just like get to know your team. Because I feel like when they start to have that level of trust with you, they're more open to be honest with you about where things are going in the project. Right?

Tera Simon:         What's helpful when you're in a management position, like you're talking to other directors that are within the company that are dealing with other team members that are on their team. So we as directors are always constantly talking as well, and so we're able to get a little bit more of that insider information that your direct report might not be telling you, but you can bring that back to them. Like, "Hey, I've heard that ... it sounds like our designer that's working with you right now might be struggling a little bit. Have you noticed anything?" That kind of helps steer the conversation that way as well.

Brett Harned:       That's awesome. Yeah, I think context is key, right? When you're managing PMs knowing a little bit about their projects, knowing about what they're working on, how much availability they have, what they're juggling. At what level are you involved in their actual project work?

Tera Simon:         What's interesting is at my current company I serve this like weird hybrid role, right? So, I work as a delivery director, and what that means is I have certain key accounts, like certain key clients that I'm responsible for the overall success of that account. So, from everything that kind of trickles in through it from a project side, from a revenue side, and from a client satisfaction side.

Tera Simon:         So, a couple of my project managers who work and report directly to me also work for me on those accounts. And so we have this weird ... there can almost be like this weird dynamic about that. So, for those accounts where they are like my accounts, I'm very heavily involved because I have to know where things are from a delivery perspective. But for me, that is also to the point you made earlier, like it makes it kind of difficult for you when you see things are not going the way you would necessarily run something in a meeting, and you want to jump in and interrupt, but you know that's not your role anymore, so you're like, "Oh God. I just have to sit here. We'll talk about that later."

Tera Simon:         So for those accounts, I'm very heavily involved. For those that are being run by other delivery directors, I have like a high level knowledge of what's going on, but I'm not sitting in on their demos, and I'm not joining in on those conversations unless I have a PM that specifically requests me to. Like they're saying, "Look, I've got a really difficult client right now, and I'm concerned about where this conversation could go. I just need support in the room." So I will go and sit in for things like that.

Brett Harned:       Nice. That's a good place to be.

Brett Harned:       All right, you've been giving us so much. I've got one final question for you. So you know the name of the podcast is Time Limit because we kind of are nodding to the fact that most people are trying to do the most that they can with serious constraints, and it sounds like you're absolutely one of those people. I'm positive that as a manager whose responsible for working directly with clients, and on projects, but also managing people and doing sales and other things, you're pulled in a lot of different directions.

Brett Harned:       So, how do you manage your time between working projects, and managing your team? What are the things that you do that help you get through days and not work like all the time?

Tera Simon:         Take it every 15 minutes at a time. But it's ... For me, the first thing I do is I get up and just glance at my calendar because you know when you leave the office, your calendar will say one thing, then for whatever reason the next morning it's completely different.

Tera Simon:         So I always just ... first thing I do is just kind of check and see where my calendar is. If I notice that I have like a two hour window where there's like nothing has been scheduled, I immediately block that for myself because I know that's going to allow me to have desk time and be able to do the things that I need to do.

Tera Simon:         I try also, for me, shut it down. You're not ... if you are starting to find yourself working 10, 12 hours a day, you're not doing yourself a due diligence, and it's not healthy. So I put restraints on myself of like I know that I'm going to try and leave the office by this time every day, and if I'm not done then I'll take maybe half an hour of work home with me, but that's it.

Tera Simon:         So put restraints on yourself that way because there's nothing ... like there's usually hardly anything that can't wait until the next morning. We're not all saving lives here, so if we can take a break and actually wait and handle something in the morning, but I'm also ... I'm still true to myself on the project manager side. I have Post-it notes all over my desk with little like to-do's and check marks, and I feel so good at the end of the day when I look at those little Post-its and I can throw one away because I did everything on it, or I can cross things off.

Tera Simon:         So, that's kind of how I manage my time. Like literally it really is take every 15 minutes by like however I can. Also, the biggest thing I have found, if you use Google for your calendar, take advantage of the fact that you can do like the quick meetings where they will book only 25 or 50 minutes and use that extra five or 10 minutes after those meetings because it gives you almost the sense of like calm before you have to go into the next thing.

Brett Harned:       Yeah. Love that. That's a really good point. I think we're the same person. I'm doing the same thing with Post-its. My to-do is like all over the place, but I get it done.

Tera Simon:         Exactly.

Brett Harned:       So that's what matters, right? It's like you can use any method that you want as long as you're getting the work done and you're feeling good about yourself.

Tera Simon:         Absolutely.

Brett Harned:       Awesome. Well thank you so much for joining me today Tera. I really appreciate it.

Tera Simon:         No problem. This was a lot of fun.

Brett Harned:       Awesome. Pet that puppy for me.

Tera Simon:         I will. I'll talk to you soon.

Brett Harned:       All right, thanks.

Tera Simon:         Bye.

Brett Harned:       Okay, I loved the appearance by Tera's dog, Dexter. Working from home is the best, and it's totally full of those unexpected communications, especially if you have pets.

Brett Harned:       Furry friends aside, I hope you enjoyed the conversation, whether you're a PM, a manager, or none of those things. I think Tera offered some really awesome advice.

Brett Harned:       All right, so this is the part where I ask you to rate the show on your favorite podcast platform, and goodbye. Thanks so much for listening.

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