Episode 3 — We Are Lovable Hardasses

“Fig 1. — A Lovable Hardass” by Greg Storey
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Show Notes

Digital project managers walk the line between servant and leader caring equally about numbers and people. It’s a challenge that requires much thought and consideration in the way we behave. While we are not managers with direct reports we work hard to build relationships with our team members to serve as confidants, councilors, and friends who have their work and best interest in mind at all times. At the same time we challenge bullshit when we see it, stand up for our clients and our teams when it’s easier to stay quiet, speak up and save our projects, and work damn hard to keep our teams motivated, our clients happy, and our projects on target.

In this episode of Sprints & Milestones, Brett and Greg explore what it means to be a “loveable hardass” and how difficult that can actually be. Some topics and scenarios discussed include:

  • Does the PM have to be the B.A. Baracus of their project team?
  • Will you ever succeed in leading teams if you play the role of “the enforcer”?
  • Building trust and good relationships on projects
  • Setting expectations for how teams work together
  • The “Trust Battery” and mutual work agreements
  • Safe words for teams

Links Mentioned in This Episode


Thank you to our program sponsor TeamGantt.

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Transcript: Episode 3 — We Are Lovable Hardasses

Announcer: Welcome to Sprint and Milestones, a podcast where Brett Harned and Greg Storey share war stories, tips, tactics, and anecdotes on navigating the sometimes rough waters of getting digital projects done. If you're leading projects and want some help and reassurance that you're doing the right things, you've downloaded the right podcast. Enjoy the show.
Brett Harned: This episode is sponsored by TeamGantt, a company I've been lucky enough to collaborate with for some time now. TeamGantt is an online project management platform that helps you to create intuitive and beautiful project plans. For more information and a free account visit TeamGantt.com. On with the show.
On the last episode we talked about being multilingual communicators, which led us to a conversation about knowing your role as a PM, boosting your confidence, and setting the right expectation for great project communications. On this episode we are talking about how PM's are lovable hard asses. Here's an excerpt from the book.
Digital project managers walk the line between servant and leader caring equally about numbers and people. It's a challenge that requires much thought and consideration in the way we behave. While we are not managers with direct reports we work hard to build relationships with our team members to serve as confidants, councilors, and friends who have their work and best interest in mind at all times.
At the same time we challenge bullshit when we see it, stand up for our clients and our teams when it's easier to stay quiet, speak up and save our projects, and work damn hard to keep our teams motivated, our clients happy, and our projects on target.
Greg Storey: So Brett, I've been thinking about this because you and I have had some issues around this kind of topic in the past with folks kind of what I feel is misinterpret what this means, and I feel like there's two different types of hard asses. There's a good PM like yourself who can be strict at times, or enforce what is needed to be done, while also being lovable, and/or relatable right?
Brett: Right.
Greg: But there's a different tact that I've seen people take and I believe that they take this permission of being a hard ass and instead they end up being just a really big jerk, and that of course doesn't bode well for anybody.
Brett: No. I mean, that's the PM that nobody wants to work with. That's the PM who gives all PM's a bad name right?
Greg: Yeah, exactly. It's kind of also why PM's have to struggle in some cases, maybe even a lot of cases, to get the respect that they deserve on the team.
Brett: Right. Definitely. Yeah, I think we're talking about, the reason that I call it "lovable hard asses", and I have to say I didn't come up with this term, Rachel Gertz from Louder Than Ten said this in some conversation we had and I really picked up on it because I really do think it's true. You have to balance right? You have to balance trust, and confidence in doing the job with soft skills and empathy and knowing that you've got to be the boss, but you also have to be the friend because if you're not the friend and understanding what it takes to get work done then it's going to be hard to motivate people to get the job done.
And it's weird because you won't always send the right impression to your team or clients if you're overly confident, meaning that you're always kind of the hard ass that's saying "We're doing it this way." You can't be rigid, and we've talked about that. You need to be able to also understand personalities, read a room, see if what you're talking about, and a lot of times what we're talking about is really kind of mundane but very important stuff like timelines and budgets, things that people care about that you do kind of have to be a little bit rigid about, but if you're not really landing a message or the message is not landing well with some people then you've got to be able to shift that conversation to the personalities that you're talking to and talk about those things in a way that will land well.
But I think in that kind of balance of trust, confidence, and soft skills that the biggest thing is building trust with teams and stakeholders, and understanding personalities and motivations because I think without trust at the core you're never going to be a really great project manager.
Greg: No. You'll be rolled over quickly and many, many, many times.
Brett: Yeah.
Greg: So, something just occurred to me, and this is going to date myself here just a bit.
Brett: Gramps.
Greg: I know. It's the A-Team right? And if you think about it the A-Team had four different personalities. Now, together they all worked, they were the A-Team, but in different times, different situations different personalities had to be used to achieve the goal.
Brett: Sure.
Greg: And again I go back to the bad ass, one of the personalities on the A-Team B.A. Baracus, the grumpy, grouchy, big muscle guy, kind of rigid in his thinking.
Brett: "Step off fool!"
Greg: Yeah. Black and white, yeah. And there are times where he was needed, but he wasn't the team right?
Brett: Mm-hmm (affirmative).
Greg: And I think it's the PM's that kind of gravitate towards that. You know the, "I've got to be the tough one. I can't be friendly. I've got to be the terse person. I've got to even speak louder than most people." How many times has that happened?
Brett: Yeah. Talking about me for sure.
Greg: Oh my gosh, and that thought just kind of occurred to me is that if you've taken it that far where you feel like you are embodying the enforcer label then you've got to step back because you're never going to be effective.
Brett: Right. And I would even take that another level and say if you actually think of yourself as the enforcer you've got a problem because it's a team effort right? Just like the A-Team, everything happened with them because they had four people doing a job right? It's not like you pull one person out and they get everything done, that's just not how it works, and as a PM you need the team to get the job done because you can't do it on your own so you better fit in well and understand what makes you a good fit.
Greg: Yeah. You and I, we've actually kicked PM's off of projects before.
Brett: Yeah.
Greg: Or had to swap a PM out because that person just was not, you know, going back to what you were talking about of building trust, having confidence, but doing all of this with grace and some soft skills, we should probably talk about that. You know, what happens when that's not gelling? How do you avoid that from happening?
Brett: Yeah. I think ideally you would always try to avoid it from happening and set some really good expectations, again, for what the PM would do on the project with the client and with the team. I think what it comes down to is the client doesn't have to like the PM and the PM doesn't have to like the client, but there does have to be mutual respect because without that respect nobody is going to really take the lead or the role where they are enforcing, and they're leading the team, and facilitating, and helping to make really good decisions.
So, I think setting that expectation has to happen very early in a relationship, almost immediately. So, a lot of times in my work what I'll recommend with agency teams is that as soon as a project scope is signed and you're aligning teams and getting ready to kick off I would have a call where the person who has sold the project to the client sits down with the client and the assigned project manager and they have a conversation about what the role of the project manager is and how they're going to help the project. Then, the project manager gets to step in, introduce themselves, start to build a relationship with the client, talk to them about important things like, "This is the scope of the project, I want to make sure that we're both on the same page about what we're doing here." So that you're level setting right away and it shows that the PM is really focused on the scope, and talking about things like budgets and timelines becomes very transparent early on.
Then you start talking about, "So, this is how we communicate as a team. This is how we work with clients. Is that going to work with you?" Then, you start talking about the organization, and the hierarchy, and the types of personalities, and the types of projects that they're working on, and then eventually you're building a relationship just out of the fact that you're sharing information and that you're showing that you actually know what you do as a PM, and you're starting to build trust immediately with stakeholders, and to me that's really important.
Having that conversation before the whole team gets to the table and positioning the PM as the leader can really help a relationship, and I think if you're not doing that, and I go think Greg in that situation we weren't doing that, I think it's easy for the PM to step in, be frazzled because they don't have all of the background, they haven't met the stakeholders. I think level setting can help, it can calm people down, and make people feel more comfortable in the role that they're in.
Greg: Yeah. You know, leading with empathy is always a good first step with that too.
Brett: Absolutely.
Greg: We should talk about trust. I feel like very week I see another article coming out about the need for trust right? That a lot of the problems come down to a lack of trust, whether it's the trust in not so much an individual, but more of a "I don't trust that you're going to get the job done, or that you're going to get the job done to my level of satisfaction, or you're going to get it done on time." Whatever that is, but a lack of trust can, as you said, lead to problems and actually put a severe dent into a project.
Brett: Yeah. I think for a PM it's not easy to build trust but it is really important. So, I look at it on a couple of kind of layers so to speak. So, organizationally, in the organization, in your role how do other people in the organization trust or even look at project managers? What is the role and do they trust that the role is there for a very important, specific job to be done, right? So, does the organization trust project management? And I've found that a lot don't, and there is kind of like level setting and expectations that need to be set from the top down in that case.
And then if you look at the project setting and if you're an organization where it's not like a smaller agency where you're working with 30 people and everyone knows each other, but in a larger organization and you're being staffed to projects and you might be working with people for the first time, and this is certainly how it was for me when I worked at Razorfish in Philadelphia, you know, there were hundreds of people, and I'd work with different people on every project, and different types of projects.
So, for me I wanted to not only have the team trust me, but also get to know me so that they could come to me with problems, and I guess that is trust, but it's also just knowing that there is a level of openness and transparency in the work that I do that I want to be your confidant. We don't have to be friends, we don't have to go out for coffee, we don't have to go to happy hour, but I just want you to know that you can come to me, and that's the harder thing to do because all humans behave differently, especially in the workplace.
Some people don't want to take that extra time for me to stop by and say, "Hey, how are things going? Do you have any concerns about the work that's happening? Do you have any questions?" Some people just want to be heads down, getting their work done, putting their time in, and leaving, and that I've found definitely happens in that bigger organization, and you might know a little bit more about this too given your recent experience too, but I think it's really important for the PM to try to crack that nut. I have to at least try to get to know these people so that they understand how I can help them so that I can give them an entry to come and talk to me whenever they need it, but also vice versa. Like, I need to feel comfortable in the fact that if I stop by to talk to you, or if I reach out to you even by email, or Slack, or whatever it is, you'll know that I'm not just a box checker sitting behind the scenes making sure you get the work done and reporting that back to your boss. I'm looking out for you, I'm looking out for the project, I'm looking out for the client, and that really kind of gets back to what the expectation of what the role is.
So, I think it's really complicated, obviously people are complicated, but you kind of have to be a little bit flexible, and that's where the lovable side of this comes in right? I'm flexible in the way that I communicate with a lot of different people because I know not everyone likes to be communicated to in the same way.
Greg: Yeah. Shopify, they've got a metaphor for trust and how you build that up, and it's the trust battery. So, their observation is, and this use this metaphor especially for new folks who come in, and this can just be new people coming in, but even new relationships starting, so a PM meeting stakeholder's for the first time. Using Shopify's kind of way of thinking about both of your batteries are at 50% and every time that you interact with your stakeholders, or even other people on the team, your battery is either going to charge or discharge on essentially accountability and integrity. You know, did you deliver on the things that you said that you would? Did you communicate? Did you followup? Did you reply? Any time that's a positive the trust between you and that other person goes up.
Once you have trust you build confidence right? Then so many things just kind of melt away. You don't have to over communicate perse. You don't have to meet with the person as much. You know, working with them is a lot easier and more seamless. You start to develop shorthand language just because you've got the trust and ideally you've been working together for a long enough period of time.
Brett: Right. Like there's a mutual agreement on how you work together, and how you behave, and how you communicate, and I think that takes a little bit of time for teams to really figure that out.
Greg: It does, but the lovable part, you know, referencing what you said earlier in the episode of being lovable and what that means of the balance of trust and confidence with soft skills. So, I feel like the people that are able to go into new relationships with better soft skills than others, they're probably coming into that relationship with their trust battery at 60%, or maybe they go in at 50 but it charges very quickly to 60 or 70%. That lovable part is so important. If you can get to that situation or that mode of operating, I think as a project manager you're just going to have a lot easier time with your role and you're going to love it even more.
Brett: I agree. And can I just say I think that sitting here thinking about this I think it comes back to not being intimidated by people, and knowing that everyone is there for a common goal, so just figuring out the best way to work together really benefits everyone, but particularly a PM. Just knowing that you have to be a hard ass sometimes doesn't mean that it gives you an excuse to be a jerk all of the time right?
Greg: Right.
Brett: Be the human that you want to interact with and I think you'll get that back.
Greg: Yeah. Totally. Well, you also mentioned how you develop all of this and you kind of do that at kick off right?
Brett: Mm-hmm (affirmative).
Greg: When I was at IBM and running multiple teams of designers in short cohorts it was my job to ensure that the work got done in a six week time frame. When I got my designers I didn't know any of them, and in most cases they didn't know each other. So, we had to come up with a way to quickly get the team comfortable with one another, start trusting each other as soon as possible so that they could actually start working on the problem that was in front of them, not working on, "Well, why is that person doing this work when that's what I wanted to do?"
After going through a cohort and seeing people bump into each other for about a week and a half until they didn't feel threatened by one another we developed an exercise where they would spend about an hour to two hours coming up with how they were going to govern themselves.
Well, I should step back. One is we had them do quick five minute presentations to introduce one another, or introduce themselves to one another to say like, "Here's who I am. Here's where I came from. Here's where I went to college. Here's why I got into design." They basically spent some time being vulnerable to a degree in front of the rest of their team so that they all kind of went through a vulnerability exercise together by having to do a little bit of public speaking, and kind of showing people what's kind of behind them as a person.
And then the second half of that was they would go into a governance exercise where they would come up with guiding principles for their team, and it could be everything from not talking over one another, to we're going to have donuts every Tuesday. There was a mixed array of rules and principles that they were going to live by, but for the most part after they were done with those two exercises I didn't have to worry if the team was going to gel with one another or not, and all of the problems I had in the beginning just kind of went away once we started doing those two things.
Brett: Yeah, there's a lot to be said for giving time and space for people to become comfortable with one another to figure out how best they can work together because that's where you find the most efficiency right? And most companies are looking for that.
Greg: Yeah. Another group that I worked with speaking of trust, they were kind of put together in an ad hoc fashion. They all four of them shared some personality traits in that they all liked to talk. When needed, or necessary they could speak to you very plainly, but when you got the four of them together they would talk over each other, they would talk nonstop, and nobody could speak plainly, nobody could say something simply, and so inevitably their hour long meetings, even in times when they were grooming their backlog of their Kanban board, an hour long session was taking four hours, and so-
Brett: Wow.
Greg: The trust in the team just went away right? They avoided, they didn't want to go in that meeting, they knew inevitably that something so simple as grooming a backlog was going to take an entire afternoon. It just got to the point where they all had to come together and basically admit that this wasn't working, and they came up with a pretty simple rule, or a simple rule for the team rather, which is they had a code word, they had a safe word, and it was cinnamon.
And so, what they would use this is if somebody was ... One, they agreed to stop talking over one another, that helped a lot, but then their propensity of speaking in long winded, so simply if someone was talking long and started to ramble a team member could just say, "Cinnamon." And that would immediately tell you that not so much that they disagreed with what you're saying, or that you're wrong, or anything like that, it's just we get it, let's move on, and it worked right? They went back from their four hour meeting back down to a one hour and the team gelled better together, they communicated better with one another.
So, that's all to say some of these things may sound complex, but some of those tools that you use to help run a team can be pretty simple and very effective.
Brett: Yeah. Absolutely. I think working in a team environment and building the trust with a team to actually create those rules for how you operate together I think can be really powerful and then you end up with people who want to continually approach projects with the same group and that can be pretty exciting.
Greg: Mm-hmm (affirmative).
Brett: Well I'm going to call cinnamon on this episode. Its been really interesting. Thanks everyone for listening today. We've talk a lot about what's referenced in chapter eight, which is about navigating difficult conversations.
Greg: Yeah, and I also think that this has something to do with chapter nine which is setting and managing expectations as well.
Brett: Absolutely. Well, I'm excited for our next episode where we will cover the topic of education and the next principle in the series which is we are consonant learners.
Brett: So, thanks again Greg and we'll see everyone next time.
Greg: Thanks.
Announcer: You've sprinted to the end of this episode. Milestone complete. Thank you for listening. If you're looking for more resources on digital project management, check out Project Management for Humans, by Brett Harned, which is available on amazon.com or through Rosenfeld Media. And of course, don't forget to subscribe on iTunes. And check out our show notes and more at sprintsandmilestones.com.

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