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Episode 10: Peer mentoring, building a support group and managing up with Nickolas Means

    Guest Biography

    Nickolas Means is an engineer turned engineering leader who’s been leading teams at companies large and small for the last decade. He’s a student of disasters like airplane crashes and a fantastic storyteller, who I’ve been able to see and hear firsthand at several LeadDev conferences. He’s currently VP of Engineering at Sym, which builds the most developer-friendly way to secure your production infrastructure and has his own podcast called Managing Up.

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    Patrick Kua: Hi everyone. Today we have Nickolas Means and Nickolas Means is an engineer turned engineering leader, who’s been leading teams at companies large and small for the last decade. He’s a student of disasters like airplane crashes and a fantastic storyteller, who I’ve been able to see and hear personally at several LeadDev conferences. He’s currently VP of engineering at Sym, which builds the most developer-friendly way to secure your production infrastructure and has his own podcast called Managing Up. Welcome to the podcast Nick.

    Nickolas Means: Thanks so much for having me on Pat. I’m excited to be here.

    Patrick Kua: Me too. You’ve got such an amazing set of experiences particularly leading other people. So could you give us a bit of a short overview of your leadership journey and maybe also when you started managing other managers?

    Nickolas Means: Yeah, for sure. So I spent about 10 years as an engineer. 6 or 7 of that at a small company where I was the only engineer. Also managed the phone systems and the warehouse systems and all the things. Then in a standard software team environment for a while. And got to see some different management approaches, some different cultures. Got to see some cultures that were pretty typical ten years ago. You know, very much the loudest voice in the room won the arguments. what we would consider tech bro culture now. And at the same time saw or heard a podcast recording featuring Alex Harms on agile communication. In that podcast, she introduced Brene Brown and the power of vulnerability. Brene’s famous TED talk that she did a while back. And all that got mashed together in my head and made me go, there has to be a better way to do this than what I’m seeing right now. There has to be a better way to lead teams than this yell until we reach consensus. So around that time I changed jobs. I intentionally, as I was changing spoke to my soon to be boss and said I really want to try my hand at management. And his response was well there’s only 4 engineers right now, so that doesn’t really make sense but I’ll keep that in mind as we grow. And lo and behold in less than a year I was in that first manager role. Fast forward a year from then our VP of Engineering had left. I’m still in the middle of trying to figure out how to be an engineering manager and I found myself promoted to VP Of Engineering and managing managers for the first time. 

    Patrick Kua: This happens quite frequently. At that point, how many people did you have to manage in terms of managers.

    Nickolas Means: So at that point I had… There were 4 managers that I was managing and the overall dev team was around 20. Everybody was functioning as a tech lead. So all of the managers were in those fifty fifty roles where you’re supposed to do half coding and half leadership that never really quite seemed to work out that way.

    Patrick Kua: Got it. And then in terms of the experience of the managers. Were they similar to you in terms of just working out what this means?

    Nickolas Means: Pretty much. Yeah. I had one that had done a little bit of management before but everybody was similarly green and had been promoted from the ranks.

    Patrick Kua: Got it. And then how long had you been working with them before you transitioned into this role?

    Nickolas Means: Let’s see. I was one of the first 4 engineers hired and they would have all come in. I think the other managers all came in in the second crop of engineers we hired. so I’d been working with them all for at least a year at that point.

    Patrick Kua: Got it. Okay. I think one of those interesting dynamics is when your peers and then you move into managing them. That can sometimes be a bit awkward. How did that turn out for you and those people?

    Nickolas Means: Yeah. That was one of the things I was most concerned about moving into that actually. But one of the reasons I got the managing managers role in the first place was that I had been doing peer mentoring sessions all along with all of the other managers in the company. Selfishly, trying to learn myself. I was more motivated around comparing notes. What’s going well on your team? Here’s what’s going well on my team. But the initiative of setting up those peer mentoring sessions and the way that some of my management philosophy had grown through the organisation. My boss thought that I think you can probably do this role. I think it’s going to feel pretty natural to everybody if you step into it. So I don’t think that’s something you really should be worried about at all and that turned out to be the case.

    Patrick Kua: Great. I love the idea particularly of that peer mentoring idea. What were the mechanics of you running those sessions? What was their cadence and how did you run it? Was it a bit more ad hoc or was it planned?

    Nickolas Means: Yeah I mean I’m a big proponent of anything that you want to happen needs to be on your schedule. So they were all on my schedule on an every other week basis. And it was, I think, I just did 30 minute sessions. It was just really open agenda. What do you want to talk about? What’s going Well? What’s not going well? Here’s what I’m struggling with. Do you have any ideas that could help me? Really no formal format at all. Just peer mentoring and chatting.

    Patrick Kua: Great. Excellent. A great way of building community and also knowledge sharing across all of you.

    Nickolas Means: Yeah, it was really great. A lot of my early growth as a manager I would attribute to those peer mentoring sessions. Because you shift into that management role for the first time and suddenly you’re feeling pretty alone in a way that you may never have before professionally. You have to go and find that community somewhere. Because we don’t as humans don’t learn very well solitary. We need community to learn.

    Patrick Kua: Absolutely. Stepping into that VP of Engineering role, there’s one of you. So alone again. Where did you go for your support and how did you learn that now that you probably didn’t have a mentoring group around you?

    Nickolas Means: I didn’t at first. That was one of the big struggles. It was easier to find that community when there were other managers in the organisation that I could talk to. It probably meant that I kept that relationship a little bit more peer than I otherwise might have. Because I was still depending on the managers that I had had those peer relationships with all along to continue helping me grow and helping me figure out how to do my job. I was fortunate enough that they were gracious to help me do that. But really, the first time that I found that community was at LeadDev. When I spoke at LeadDev for the first time, suddenly I’m in a room full of people that are all facing the same struggles. None of which work at my company and I started building a good community there.

    Patrick Kua: Great. In terms of connecting to that community, what channels did you use and how often did you reach out to people?

    Nickolas Means: One of the reasons I got into speaking at conferences in the first place is that I’m a fairly hopeless introvert at big events like that. It was a way to conveniently bypass the small talk that introverts don’t really like to do most of the time. Because if you get on stage and you talk then suddenly people want to talk to you about the thing that you talked about on stage and you’re prepared to have that conversation. It’s much less social pressure. So some of the relationships that I formed at that first LeadDev, some of the folks that I met that first time, I would just reach out when I would hit choppy water and need help and try to figure out how to navigate something.

    Patrick Kua: That’s great. Yeah I mean I think we share quite a lot of similarities. That introvert thing. It’s very true, when you’re speaking, it makes it a lot easier for people to come to you around a topic instead of you having to break ice with people. I think a lot of people get surprised that a lot of speakers are actually introverts. Particularly at things like LeadDev where, you know, typical manager conference. People think everyone needs to be an extrovert which is often not the case. 

    Nickolas Means: Yeah, absolutely. I mean I went to so many conferences and couldn’t figure out why people enjoyed conferences so much until I started speaking.

    Patrick Kua: I could definitely relate. Let’s talk a little bit about your first experiences when you were to reflect back on managing other managers. Were there any big surprises for you or what were some unknown unknowns when you went into that role?

    Nickolas Means: I mean I think that the thing that surprised me most was probably the feedback loop. When you step into being a manager for the first time I like to talk to new managers about what I call meta productivity. So this idea that you need to start finding satisfaction in the work that other people are doing. You need to be able to find your professional happiness in watching your team do great work versus typically, as an engineer, being happy with doing the work that you’re doing hands on. Well then you step into a managing manager’s role and suddenly you’re into meta meta productivity. Those feedback loops just grind to an absolute halt. It’s really difficult when you first start, or at least it was for me, when I first started managing managers to figure out, OK, how do I even have an impact in this role? What can I do that’s going to make a difference for anybody?

    Patrick Kua: Yeah, and if you were to maybe guess like time spans of feedback loop comparing maybe individual contributors and managers to managing managers, what were the relative sizes of those feedback loops for you?

    Nickolas Means: I mean I think when you’re managing managers some of it is dependent on the cadence at which your organisation operates. We were on a quarterly planning cycle and that was really the effective feedback loop that I could see for myself is, did we deliver software effectively this quarter? Did we deliver it more effectively than we did last quarter? Which itself is a very subjective measurement. I mean there’s no way to objectively say, oh yes, we absolutely did better this quarter than we did last quarter. So you’re still dealing with squishy stuff that you’re looking at and trying to find some truth in. But at least as a manager your cadence and improvement is 1-1 to 1-1. You can usually see somebody start to apply a little bit of what you say from 1-1 to the next. Managing managers, you’re generally not in planning meetings. You’re generally not in meetings that your managers are leading. I mean sometimes you drop in, but that like a Schrodinger’s thing. It tends to change the meeting when you show up. 

    Patrick Kua: Absolutely.

    Nickolas Means: So if you’re there to observe it, it’s going to be a different meeting than if you weren’t there to observe it. 

    Patrick Kua: Absolutely. Those power dynamics make a big difference.

    Nickolas Means: They do for sure and so it’s tough to get that feedback. Even the same feedback loop you get as a manager.

    Patrick Kua: Yeah, absolutely. One of the things that some managers of managers do are things like skip levels in terms of trying to shortcut some of the feedback loop and get direct stuff. Is that something that you were doing in that role back then and how frequent were you doing skip one to ones?

    Nickolas Means: It was. But I had so many people that I did maybe one a quarter with each of my report’s reports. So I could get a little bit. But you don’t get the longitudinal feedback that way. If I had a manager that was particularly having trouble, I might talk a little more frequently with their team lead and try to figure out what was going on in that situation. But really, I wasn’t doing a whole lot of that at that point. I would develop that skill set a little bit more later on in further managing managers’ roles than I did in that first one.

    Patrick Kua: Got it. Excellent. One other thing I heard you say which I think is what a lot of directors or VPs struggle with, is talking about that productivity and measuring. You often have this relative view of seeing these different teams. For you, what are some signals of things that you look for, knowing that teams are being more productive or how do you go about thinking about that philosophy today?

    Nickolas Means: That’s a great question. Again. It’s so tempting to look at metrics and let metrics guide you on this. They can be helpful but they always only tell part of the story. So anytime you see an anomaly in the metrics you have to dig in to try to figure out why that’s happening. The thing I tend to look for more than anything. I have a very high agency, high autonomy leadership style. That’s the style that I want the leaders that I manage to build as well. And so a lot of what I’m looking for is how fluidly is your team working. Are they getting along? Are they able to do projects together? Or is there this constant chaos bubbling up from the team that you manage because you’re really struggling to get them to work together? That for me has proven to be a pretty reliable leading indicator of how much work a team is going to be able to get done.

    Patrick Kua: Great. Excellent. I love that, how much chaos and how fluid is the team. I think they’re really good indicators as well and maybe how much do you end up getting involved in as well and when things escalate. Let’s talk a little bit about your podcast. So how long have you been running managing up for and why did you start it?

    Nickolas Means: That’s a good question. I think we’ve been going for about 3 years now and I actually didn’t start it. Brandon and Travis had recorded a couple of episodes before they decided they needed a third voice in the conversation and asked me to join in. We joined it. We started it. The funny thing about it is the name’s actually a clever pun. We didn’t even do an episode on managing up for the first couple of years that we had the show. The motivation behind it was all 3 of us have this focus on human centric leadership. Empowering other people to do their best work. And wanted to talk about that. Especially 3 white men in tech who carry some privilege. How can we leverage that privilege to try to change the way that management happens in the world of technology? So we decided the best way to do it was to have a podcast and talk about some things that people don’t ordinarily talk about on software leadership podcasts.

    Patrick Kua: Great. I love the idea. I didn’t realise actually that you didn’t start talking about managing up at the very beginning but more further into the podcast. That’s amazing.

    Nickolas Means: It was one of those things we felt guilty about for a while. It’s like the show is called managing up. We should probably do this episode but we kept having other things we wanted to talk about more.

    Patrick Kua: That’s great. I think it’s nice. You got to go with the flow sometimes right? 

    Nickolas Means: Yeah.

    Patrick Kua: So as somebody who is a manager of managers and when you think about managing up how well do you rate how some EMs do at managing up in general? Do you think people are instinctively good at it or what makes people better at it than others?

    Nickolas Means: I mean I think there’s a funny nugget of truth in the fact that it took us 2 years to record an episode on managing up and it’s that we don’t like to talk about it just in general. It’s not a subject of conversation that comes up very frequently. bBecause it’s a little weird and unpleasant to talk about. Okay, how do you manage your manager? How do you get the most out of your manager as an engineering manager? I think you mentioned power dynamics earlier. I think that is what makes managing up such a tricky subject. Because it is pushing against the power dynamics a little bit. 

    Nickolas Means: I think quality of managing up is all over the map depending on an engineering manager in their orientation to the world. if you’ve got somebody that’s hell-bent on a promotion to director and and really wants to be seen as highly competent, sometimes that will pull them into a place where they’re being very private and very hidden about the work that they’re doing because they want to surprise you with all the good work they’re doing. If you have somebody that’s more focused on just getting the work done and letting the work speak for itself, sometimes there’ll be an open book. Tell you everything and then some that you need to know to be a more effective manager for them. It’s all about as a manager of managers figuring out how to balance that communication. Figuring out how to pull more of the good stuff. For me, a large part of my focus as a manager of managers is never punishing information. 

    Patrick Kua: Yeah.

    Nickolas Means: Sometimes it’s hard when somebody surprises you with bad news that’s delivered later than it should be. I will get around to having that conversation with them at some point but I try really hard never to react negatively in the moment because I’m just so glad they said something to me.

    Patrick Kua: I love that approach and I think it reminds me of building psychological safety. Of letting people know bad information is good information even though it inherently might have a negative impact or something bad for the business. But as you said, it’s better to know earlier than later and that somebody talked about it versus hiding it away in an uncomfortable drawer somewhere.

    Nickolas Means: And it is a thing where you do as a leader have to intentionally counteract the power dynamics in that relationship. Or encourage people to tell you uncomfortable things. Encourage people to tell you what is their team struggling with right now. The thing about managing up is someone who is managing managers, a VPp or a Director. Somebody in that role has a lot more organisational resources at their disposal than somebody who’s an engineering manager. The only way a manager of managers can bring those resources to bear on a problem is to know about the problem. And so if you’re not managing up effectively if you’re not sharing your wins and your struggles, then your manager doesn’t have the chance to celebrate your wins more widely. Your manager doesn’t have the opportunity to bring their resources to bear to help you solve whatever problem it is to get you more resources to help you move faster. I’ve borrowed people from other teams before to help a project that was struggling or that needed a particular skill set. There’s all sorts of tricks that a manager of managers can do as long as that relationship is open and there’s good feedback going both directions.

    Patrick Kua: Great. One of the archetypes of managers that I heard you talk about was the manager of heads down, the work will speak for itself, which often means that you as a manager or manager don’t have a lot of signals. Have you had to get people to provide more information those sorts of circumstances? How do you get them to give you more information or transparency from that perspective?

    Nickolas Means: Almost always for me that’s been a matter of safety. So somebody that’s in that mentality of I’m not going to tell my manager anything. I’ve got a lid on this pot. Nobody’s going to find anything out. Six months, a year, a year and a half into managing that person, you find out it’s because of previous organisational trauma, they’ve experienced a manager that was terrible to them. That didn’t trust them. That micromanaged them or that that took away responsibilities from them in a way that seemed unfair. And so you have to get past that unsafety to get them to a place where they even feel comfortable sharing and it’s one of the things. You start getting information in bits and bites and every time you get that information, you have to react overwhelmingly positive to thank you for telling me that. And overreact. Make sure that if they’re asking you for help, you better deliver that help. Because that’s how you build that credibility that gets them to feel safe giving you more information and trusting you to help them when they’re having trouble.

    Patrick Kua: Love it. Building the relationship and responding to the signals that they’re giving to you and recognising some of that trauma and trying to help counteract that and to signal that you are not the same as probably what they’ve experienced in the past.

    Nickolas Means: Yeah. I mean the other thing I do is I have a very deliberate focus on 1-1s. I mean there’s the general advice on 1-1s that this is your meeting. Not my meeting. You bring the agenda. I go out of my way to make sure everybody I manage and knows that it’s okay if we don’t even talk about work in our 1-1 because most of what we’re there to do is just to build a relationship as colleagues so that we can work together more effectively. We might spend 30 minutes talking about your kid’s soccer match or whatever before we get around to the important thing that you needed to tell me because it took you 30 minutes to build up the courage to say the thing that you needed to say.

    Nickolas Means: And without that 30 minutes of talking about family or life or whatever happened/happens outside of work, you might never get to that point. So that deliberate focus on building relationship and building friendship beyond just the work relationship has been really important to me in my manager career.

    Patrick Kua: Yeah I think it’s super essential for any effective manager and I think it’s great that you make some time for that. Given your focus on 1-1s have you found that 1-1s with managers are different from 1-1s with individual contributors? And if so what are the differences?

    Nickolas Means: There’s a lot more ground to cover when you have a 1-1 with a manager. When I’m managing individual contributors my default 1-1 is 30 minutes once a week. When I’m managing managers it’s an hour once a week. Which feels like a lot of time but I’ve never had trouble filling that time up. And you can always give time back. I mean if you don’t have the time on the calendar, it’s tough to get it. But if you do have the time on the calendar and you don’t need all that time, it’s easy to give some of it back. 

    Patrick Kua: Got it. What do you mean by cover more ground?

    Nickolas Means: There’s just a lot more to talk about when you’re managing a manager because there’s often, they’ve got six/eight people on their team and you need to go through and check in on all of them on a periodic basis. How is this person doing? Hey, I remember three months ago you told me that this person was really struggling. Is that turning around any? Maybe you’ve got an improvement plan for somebody on their team that you’re managing on an ongoing basis and you need to be managing that up to your VP or whoever is going to have to deal with the outcome of that PIP (Performance Improvement Plan) at the end of the day. There’s just a lot to talk about and then on top of that you’ve got the work to talk about. How’s the project going? Are you ahead? Are you behind? Are we going to hit this critical date? Oh no, we’re not. What help do you need to hit that date? Is this a thing that we can speed up by adding more people to it? Is that just going to slow you down? Yeah, there’s just there’s so much to cover that if you want any time to cover any relationship and personal stuff in addition to work stuff it just takes an hour in my opinion.

    Patrick Kua: Totally agree. And thank you for providing some of those concrete examples. Let’s go to the other archetype that you were talking about which is the engineering manager that is maybe very over communicating because they’re looking for that fast track to director. How do you handle those situations as a manager or manager?

    Nickolas Means: It’s interesting. When someone is communicating in an almost inappropriate level of detail to you, to the point that you can’t understand what they’re telling you, that’s feedback that you have to figure out how to give them. You have to tell them we’ve only got an hour here. I need you to summarise this a little bit more so we can cover a little bit more ground. A lot of it is helping them understand the agency and authority that they have to solve problems on their own. Because sometimes those conversations happen because somebody’s looking for permission. Or affirmation. That they don’t necessarily need. Just because they haven’t had. Maybe it’s a first time manager that hasn’t had the authority that they’re carrying now. They don’t know what to do with the formal authority yet. Maybe it’s somebody that’s used to being micromanaged and you have to wean them off of micromanagement a little bit and get them more comfortable managing themselves.

    Nickolas Means: So again. I think with all of these things that are anomalous. You have to start from a place of curiosity. if you treat the symptom you may make the symptom go away. But it’ll come back because anytime we’re in crisis these things, these natural tendencies tend to come back. Unless you’ve done the curious work to ask the questions to figure out. Okay, why? Why are you communicating with me like this in the first place? Okay, let’s solve that problem and then trust that the downstream symptoms of that problem are going to sort themselves out. 

    Patrick Kua: Great that requires quite a lot of observation and reflection on what are the needs that this person is having and how can you get them to talk about those needs and maybe be a bit more direct around that. So I love that approach that you talk about. One thing I notice about your style is, I think you’re very deliberate around the style of management that you’re looking for. High agency. High autonomy. I’m sure over your past, you’ve probably had managers, maybe inherited managers who didn’t fit that mold. How do you go about reshaping their approach to management?

    Nickolas Means: So the interesting thing about that is you don’t always have to reshape it. If you take a manager who is more directive. Uses more formal authority to get the work done is used to having a finer point on the work that’s happening on their team. They’ve constructed their team in such a way that that’s the style of management their team generally wants. If you change their management style dramatically. If you force them to shift management styles, suddenly you’ve made their team incredibly ineffective.

    Nickolas Means: So it’s not always a good idea to go in. Just because somebody doesn’t practise the management style that I prefer and that I prefer to see from people that I manage, doesn’t mean I need to change it. So I tend to start from an outputs perspective. Like are there things, are there ways that this team could be operating more effectively if their manager gave them more agency and autonomy? Are there things that we could do to get them operating more fluidly? Are they haemorrhaging people? Are people constantly leaving their team? Okay, well, that’s probably a sign that they’re maybe a little overbearing as a manager and something here needs to change. But if there’s not a problem oftentimes it doesn’t make sense to try to fix it, even if it’s not a management style that I love or would thrive under because there’s people of all sorts that thrive under all sorts of different management styles.

    Patrick Kua: Great. I mean that is a huge testament to your maturity of recognising those different styles and understanding where they’re appropriate and the fit and that dynamic of what you describe as the team and the manager and how well do they work with each other. One of the things that I heard you say there was around this output. So what other examples of outputs are you thinking about? One thing I heard was around attrition of people. What are other symptoms or outputs you would look for?

    Nickolas Means: I mean if you build a safety relationship with your skip levels. You’ll hear about their manager in those conversations. Sometimes it takes a few conversations to get to the point that they’re comfortable talking to their boss’s boss and sharing real information. But if they’re in crisis, it usually won’t. If they’re in crisis, they usually want something to change quickly. And you’ll quickly pick up on a theme in the skip levels that you do with the folks that report to this manager if they’re really struggling. If that manager’s management style is not resonating with the team. So that’s one of the ones that I look at. Another is just constantly missed deadlines. If they’re setting goals constantly and then not getting there. Sometimes that’s a symptom of, especially if a manager that I feel is a little overbearing anyway, that the team has outsourced too much of the responsibility for hitting deadlines to their manager and they’re not doing enough thinking on their own. And we need to rebalance that a little bit so that the whole team is oriented together around hitting those deadlines rather than trusting the manager to keep the trains running on time the whole time.

    Patrick Kua: Got it. Makes sense. We’ve talked a little bit about managing managers directly, different styles. One of the things that you’ve probably done over your career is also having to spot new managers and to think about that next pipeline of management talent. What’s been your experience of how do you go about spotting those people and how do you support them in that transition to being a first-time manager?

    Nickolas Means: The people that I’ve seen most successfully transition into management are the people that bring problems. So when I’m managing, either in skip levels or if I manage a team directly and am looking for someone to hand that team over to, so that I can uplevel myself, I’m always looking for the one who’s observing the team. Who’s pointing out problems with the people dynamics. Pointing out problems with the process. And not just pointing out problems. Having ideas for how to fix those things. Changes that they would like to see. It’s the person that’s observant of the system and the way that the system is behaving and operating. As far as how do you help them transition in? I think the most important thing is to give people a taste of management before you give them the title. So let them lead a project or two. Give them some formal authority. Managers of managers often find themselves in this situation where they’ve got the L-shaped organisation, where they’re managing a couple of leaders and then managing one team directly. Well find somebody on that team that you can start offloading some of the management responsibilities to. Somebody hopefully that wants to transition into management. Because it’s a great way to give somebody a taste of it before they get the formal title and then find out they don’t like it and have to navigate the transition back to IC. It’s a whole lot easier to find that out before you step into the role.

    Patrick Kua: I love that. Giving people that taste but also that optionality or the reversibility of this is definitely not what I was expecting. Or maybe I don’t want to do more of this and then choose to go back to an individual contributor.

    Nickolas Means: It’s a whole lot less threatening that way. And you get a much better take of is this a thing I might enjoy or not. Because then you get the formal title and it’s always going to be harder than you expect it to be. There’s always going to be more adjustment than you expect there to be. But if you’ve gotten a positive taste of it before you go into that then it’s easier to get through some of those early speed bumps and get to a point where you find your groove as a manager.

    Patrick Kua: Great. In terms of the support that you give people, giving people the opportunity to try stuff to experiment. To have that formal authority and that reversibility is there anything else that you do to help support new managers or potential new managers?

    Nickolas Means: Yeah I mean I encourage them to pick a book and read it. Sarah Drasmer’s book is really good. Lara Hogan’s book is really good. If they’re interested more in what’s the overall career arc, what is the multi-year journey I’m signing up for here, Camille Fournier’s book is really good. so I encourage them to pick a book and read it. Don’t pick all the books. Don’t try to read every book on management out there. Just pick one. And then I also encourage every new manager to read Turn the Ship Around by David Marquet. That’s my favourite leadership book of all time. Itd does a really good job of dissuading new leaders from thinking that they need to be directive all the time. Which I think is often a thing that you need to take care of upfront with new leaders. Making them understand that, no, you don’t have to dictate everything that happens on your team. Your job is to create the conditions for success. Not to create the success.

    Patrick Kua: Love it. I can see that reflected in your own leadership philosophy as well. So great book picks and we’ll make sure that they end up in those show notes as well. Let’s talk a little bit about differences because we’ve talked about your first VP Engineering and experience managing managers but you’ve been a manager of managers in other companies as well. So if you contrast them what would you say are similarities or differences across organisations or scopes of managers that you’ve had to manage?

    Nickolas Means: I mean I think probably the biggest difference I’ve noticed is my first manager of manager’s role was in  a startup that was growing, so there wasn’t a lot of politics involved there. Another one of my manager of manager’s roles was in a large organisation and there was more organisational politics there. I like to joke that if you look at the talks that I’ve written over time you can tell what I’m learning at any given moment. I wrote my talk on the Eiffel Tower as I was joining that large organisation and dealing with a lot more organisational politics for the first time. And that talk is very much about the idea that politics aren’t bad actually. They’re just how humans share power and they can certainly get toxic. There is certainly bad politics. But in general, if you want to be a leader, especially higher than engineering manager in an organisation, it’s a thing that you have to learn to navigate and to negotiate. So I spent more time on that in that organisation, and learned the hard lessons about if you’re trying to be a shit umbrella, you’re going to burn yourself out because you just cannot bear that weight all the time. And it’s not healthy for the managers that you manage either because if they’re going to grow their careers, they need to see some of that stuff. They need to understand that’s how organisations work in the real world and so as a manager your job is to expose them safely to some of those things. Help them see how the sausage actually gets made. But not in a way that’s going to be overwhelming. Or instantly burn them out or turn them off on the idea of a career in leadership. There’s much more of that focus in a larger organisation because there’s just much much more of that stuff to deal with in a larger organisation.

    Patrick Kua: Yeah I love that. If I remember I think this is where you were talking about the difference between being the umbrella and that heat shield.

    Nickolas Means: The heat shield. Yep.

    Patrick Kua: Of making sure that some things come through but not completely protected from all of that.

    Nickolas Means: Yep, exactly.

    Patrick Kua: Great. So I guess organisation size and the complexity of that shifts your experience as a person who managers manages. Are there any other differences that you can think of across your different experiences?

    Nickolas Means: I mean the other thing is in a larger organisation, you have a larger pool of engineers to draw from. So when you get in one of those situations where a team needs help or is being asked to do a project they’re not fully staffed for, you learn how to go and borrow engineers from across the organisation for a period of time. Especially in a large organisation where you’ve got Principal Engineers to deploy. Oftentimes, even as a Director of Engineering that Principal Engineer is still going to report up into a VP, so part of the managing up you do as a director in a large organisation is going to make your case for why you need this Principal Engineer for a certain period of time to make this project successful. So figuring out all of the resources that you have available to you and all of the ways that you can make your team successful in the large organisation. There’s just a lot more options available to you and you have to learn how to play all of those different cards.

    Patrick Kua: I find that really fascinating. I’d like to follow that a little bit because I can visualise this large organisation and more options. How do you start discovering those options and how do you start to learn about what else is in the organisation?

    Nickolas Means: I mean a lot of it is dependent on your relationship with your manager. So the VP of Engineering that large organisation. SVP of Engineering. Presumably, you’re having regular 1-1s with that person talking about what’s going tough, what you’re worried about. Oftentimes when you start talking about this is the thing that’s worrying me. This is the thing that’s causing me to not sleep as well at night. Do you have any thoughts on how we can de-risk this? That’s when they start going through their mental rolodex and going, okay, we could do this. We could do this. We could do this. These are the things that we could do to try to reduce the risk of that project.

    Nickolas Means: Or you find out this thing that’s maybe a huge priority to you that you’re incredibly worried about is not as big, an organisational priority and you can afford to turn the heat down a little bit on that project and let it take a little bit longer to develop. So there’s a bunch of different things that happen but it all starts with having that open line of communication with your manager. The other thing that you have to do in a large organisation is spend time networking. If you’re not talking to sales reps, if you’re not talking to marketing, if you’re not talking to product and product leadership on a regular basis, then you’re missing out on a whole world of input that you could be having that would make your work more effective. And again bring more resources to bear. I mean maybe a product marketing person can give you some great insight on, okay, you’ve got this this punch list of 10 things you think this feature needs to do. These top 3 are the only thing our customers care about.

    Patrick Kua: No, I absolutely agree. And that networking thing seems to be very common theme for a lot of people in managing managers. Of A) discovering who’s out there and then B) spending time with them. Do you have any heuristics for yourself in terms of like how much time you spend with say engineering versus other departments or teams?

    Nickolas Means: I don’t and I probably should. It tends to be more happenstance based on who I meet and who I enjoy talking to. I’m probably a little bit too oriented and around what I enjoy and who I enjoy talking to in that situation. But yeah I mean again, it’s the sort of thing that I’ll have a conversation with somebody that’s on a specific topic and I’ll really enjoy the conversation. Get a lot out of it. At the end of the conversation, hey, do you mind if we catch up once a quarter or so? I really enjoyed this conversation and I’ve gotten a lot from it and I hope you have too. And 99 times out of a 100, that person is just as happy to have that quarterly meeting on their calendar.

    Patrick Kua: Great. I mean I don’t think there is a need for heuristics in general. Some of it will also probably depend on the product or the thing that your team is working on because as you say, it’s what’s the reason or something to talk about and to reconnect with people. Absolutely. In terms of managing upwards to your manager, do you have any tips that you like to consciously use or draw upon?

    Nickolas Means: I try to think about the thing that scares me most to say to my manager on a regular basis as a forcing function to make sure it’s not something I should be saying. A lot of times it’s not. A lot of times it does fall into that bucket of, okay this is a problem that I need to manage myself, and not something that I need to loop my manager in on just yet. But sometimes when I go down that road, it’s, okay, it’s time for me to swallow my pride and have this conversation. This is a way that I’m really struggling and need some help and I need to care more about getting this project done than my own ego in this situation. So a lot of it’s just self-management. A lot of it’s staying on top of, okay, I feel the urge to hide this thing. That’s probably a good signal that I shouldn’t hide this thing.

    Patrick Kua: Got it. Make sense. In terms of where you go for support, what does that look like today versus when you first started out?

    Nickolas Means: I mean when I first started out I didn’t have a ton of support until I started getting into the LeadDev community. I would have periodic conversations with those folks. My support network now, my closest network is Brandon and Travis, that I do Managing Up (the podcast) with. We have not been as consistent recording lately as any of us would like to be. But we still talk every Thursday. And the reason that we haven’t recorded anything is that we’re often talking about things that we can’t record. So pulling ourselves back from that conversation, that peer mentoring, to actually record an episode has been a struggle of late. And has been since the start of COVID. It was really the primary support group that all 3 of us found to get us through the pandemic and the changes in leadership that happened during the pandemic. I also still have a bunch of folks from the LeadDev community that I’m close to and really enjoy talking with. That I’ll reach out in a Board of Directors style sometimes when I’m trying to make a career decision and just get advice on that thing.

    Patrick Kua: Great. I’m really happy that you have a stronger, broader support network from when you first started. I think a lot of people end up in a place where they do everything solo and they feel like they always have to do everything solo. So it’s really great to hear that you have that. And it’s grown and supported you throughout those difficult times.

    Nickolas Means: Yeah I mean in shifting back to what resources what I point new managers to, I come back to Lara Hogan’s manager voltron a lot. Because you do have to build that support network consciously or you will find yourself in that position where you’re very alone and you don’t have anybody to talk to and the job is just way less fun if you don’t have anybody to talk to. If you’re trying to bear all that load yourself. And it’s a hard job. You need the support.

    Patrick Kua: Absolutely. In terms of support for managing managers, are there any resources or things you would point people to?

    Nickolas Means: I’ve really enjoyed Herb Cohen’s books on negotiation. I think that tends to be a pretty critical skill because often as a manager of managers you’re looking to get something out of a team. A manager of a team is looking to get something out of their team as well and sometimes they don’t line up. Sometimes you need to get them to push the team a little bit harder to hit a really important business deadline. You have to figure out how to get that to happen in a way that’s mutually beneficial. So how do I get you, as a manager that I manage, to push your team a little bit harder? Well I can offer a few different things. I can offer, maybe we can send your team to a conference. Maybe we can give your team some extra time off after this push is over. I can give you the reassurance that once you hit this deadline, there will be time to rest and recover. So it’s just a matter of learning what everybody’s coming into a situation with and what their motives are in that situation. Yeah, there’s a lot of books out there on playing professional poker that are good in this way as well. Annie Duke’s Thinking in Bets comes to mind along those lines.

    Patrick Kua: Yeah, that’s a really good book. I really enjoyed reading that one actually. Changed my thoughts on decisions.

    Nickolas Means: Yeah. I mean it’s often the thing that you’re trying to figure out is what motives is everybody coming to the table with and that includes yourself?

    Patrick Kua: Yeah.

    Nickolas Means: Because we’re often not very good at being honest with ourselves about what our motives in a situation are.

    Patrick Kua: Absolutely. I totally agree. And then in terms of final words of advice for people who are currently managing a team, thinking about stepping into a managing manager’s world. What advice would you provide to them or tips?

    Nickolas Means: Be patient with yourself because it takes a really long time to figure out if you’re being successful in the role and if you like the role. You need to be committed to, when you step into that role, doing it for a year to figure out if you like it or not. Because the feedback loop is so much slower. Because so much of it is just systems thinking where you’re purely going, okay if I give this input to the system, let me follow the line through and see if I can figure out what outputs that input led to. That takes a really long time to do. If you go into that role and you think you’re going to change a bunch of things and you’re going to turn the world upside down and everybody’s going to be happier and more effective, you’re in for a bad time. It’s not going to go the way you think it is.

    Patrick Kua: Surprise.

    Nickolas Means: You got to get in the role and you have to spend some time observing. You have to spend some time trying to figure out, okay, what things are not going as well as I would like them to? And then you got to pick your battles. You got to pick which one or two things you actually want to change because that’s really probably all you can affect at a given time with the levers that you have available to you as a manager of managers.

    Patrick Kua: That’s some really amazing advice and I’m sure some of our listeners will really appreciate that. So thank you very much for sharing. 

    Nickolas Means: Yeah.

    Patrick Kua: In terms of where can people find out more about you or follow you online?

    Nickolas Means: I’m nmeans on pretty much all the social networks and I maintain a blog sporadically at I’ve also done a lot of writing for the folks at LeadDev so you can find a lot of my writings and talks on the LeadDev website.

    Patrick Kua: Great. Amazing! Thank you very much for your time on this podcast. I wish you all the luck for the Managing Up podcast. I’ve really enjoyed the insights and stories that you shared with us today. So thanks very much Nick.

    Nickolas Means: Yeah, thanks so much for having me on Pat. It’s been a fun conversation.

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