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Ten(ish) Tips w/ Maureen Calabrese

October 25, 2021
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An Introduction to Maureen

Maureen is the Chief People Officer of Sprout Social, where she pushes her People team to think and lead like product managers. Previously the CPO at Raise and Cision, Maureen began her career in marketing before moving to people leadership.

Our wide-ranging conversation touches on the future evolution of the People function, bad advice and habits in HR, and having difficult conversations with your CEO.

- Joseph Quan | CEO & Founder, Knoetic

What advice would you give someone who’s recently become a Chief People Officer for the first time?

I hope this goes without saying, but it’s still worth calling out. You must understand the business of your company - far beyond the surface level.

When you’re able to step beyond your role, and speak not only about the people side but the business, then you earn the permission and the platform to drive the change you seek. It gives you the credibility to put the right teams, culture, and systems in place.

As a Chief People Officer, you should be able to explain how your business makes money the way your CFO can. When you think about it, wages and benefits, both of which fall underneath the Chief People Officer’s purview, tend to be in the top 3 company expenditures. It’s incredibly important for every CPO to understand the financial equation. It doesn’t stop there - you should be able to speak to customer needs and impact the same way your CRO or CMO can. Or evangelize the vision like the CEO.

But if you don’t come with a solid business foundation you can stand on, then you’re working against all the preconceived notions and biases other people may have about the HR function.

For better or worse, when you’re in the people function, you almost have to work harder to prove yourself.

How do you build trust with colleagues who might have those preconceived notions of leaders in the people/HR space?

For starters, the fact that coming into the people world was a career change for me has been incredibly valuable and is still something that I bring up really early on when I’m meeting people for the first time. I think that them knowing that I’ve been in their shoes, particularly as a manager, and coming at things from where they’re sitting has been really helpful.

When we first introduced the concept of the people business partner at Sprout about two years ago, there was this whole question of, “What is a people business partner? I’m hearing about this, but I’m still not exactly sure what you’re doing here.”

That’s where speaking the language of the business and being able to understand other fields becomes really valuable. There’s a craft to that and being able to articulate our role involves being able to see people patterns and make those connections between disciplines.

Another important part of it is that I use the word systems really deliberately when referring to our work rather than processes. Although they seem to have similar meanings, when you think of systems, that sounds comparatively more like something that’ll successfully support what you’re doing rather than get in the way of it. By equating our work with that of designers, salespeople, or product folks and putting things into terms familiar to them, we can put these strong systems into place and actively partner with them on a business perspective.

To give an example of this idea of seeing patterns, there was one organization where I was working across multiple teams and I noticed that it was really hard to come into that organization as a new leader. But the executive team didn’t really have any insight into that originally, probably due to the fact that each one of them were only dealing with the specifics of their circumstance. However, being in my position where I was working across multiple levels and multiple teams, I was one of the only people with access to notice those kinds of patterns and see that issue play out and in doing so, I was then able to speak to it for the executive team.

They pushed back on me a little bit at first, but that’s where having the data and being able to say, “Here’s how it happened in this team and again over here,” and that discussion ended up changing our entire onboarding process, especially for our senior leaders in terms of adding more specificity to what we expected them to do while recruiting.

What happens most of the time is that we as leaders have an expectation of what we want our new leaders to accomplish, and so they come in really charged to do that, but the team usually has a different impression of the purpose they’re there to serve. Seeing that pattern, we were able to equip our new leaders with the right expectations and be more successful.

So much goes into recruiting a leader and a certain amount has major ripple effects, so the system that came out of those patterns in that case was incredibly valuable.

How do you hope the people function will evolve in the coming decade?

Personally, I’ve always been fascinated by product management. When I was starting my career, product management wasn’t a career choice the way it is now. But I think if it had been and I could turn back time, it might’ve been something I would’ve pursued instead.

I would love for people functions to start thinking about themselves as product organizations. That’s what we do with my team. We follow our product org, for instance, when they’re coming up with a new feature set and they write an approach brief for stakeholders explaining the tradeoffs, reasoning, and concerns with all that they’re working on.

I have everyone on my team, when they’re rolling out something that’s programmatic, write an approach brief like that of our product team. I have them think through the experience of who are our users for this, what data do we need to understand if it’ll be successful, and what are the moments we need to focus on from a user experience perspective. We think frequently about our ‘go-to-market’ approach: how are we going to secure buy-in from the organization, drive adoption and create recurring engagement with our new program?

I ask people to think of HR through that lens and it’s been powerful for us, it’d be really cool to start seeing other organizations do that as well.'

[Joseph’s note: For another take on the future of HR leaders as innovators and creators, check out our interview with Gainsight CPO Carol Mahoney]

I would love for people functions to start thinking about themselves as product organizations. That’s what we do with my team. We follow our product org, for instance, when they’re coming up with a new feature set and they write an approach brief for stakeholders explaining the tradeoffs, reasoning, and concerns with all that they’re working on.

What is the best investment you’ve ever made in your life (time, money, etc.)? Why?

I thought about this question, and I’d love to give you a really philosophical answer, but I’m going to be straight up with you: it’s my Peloton bike. And I’ll tell you why.

I debated for close to two years with myself and with my husband thinking, “Is this really worth it?”, and ended up purchasing it in January. Since then it’s completely impacted my life in so many ways, certainly from a health standpoint, but also just in overall wellness.

They have meditation, they have yoga; I sound like a commercial and I don’t mean to, but having this holistic approach to wellness, especially now, was never something I really did before. But now that I have access to these things in my home and they’re convenient, they’re served up in a way that’s really compelling and are a lot easier to build into my life.

The data geek in me also really loves the ability to download my activity spreadsheet every month so that I can look at the graph and see where I can improve, so that’s been fun for me as well.

What’s a small change in your life that made a big difference?

Breathing. Before I started meditation, people would always tell me, “Just take a deep breath” and I would be frustrated with that, feeling like it was just an easy answer to give. But now, I’ve sort of incorporated that when things get overwhelming and have this cue to myself to take a deep breath, which has become really important for how I go about my work and also how I’ve been coaching my people business partners who are on the forefront of all that’s happening.

People come to them and they’re emotional, they’re stressed, and anxiety levels are high, and my team feels compelled to want to solve their issues and make things better.

I’ve been teaching them and myself as well: just take a breath. The best solutions come with space and there are moments where the urgency is immediate, but recognizing the breath, both physically and metaphorically, allows you to take a moment and get the space you need to come back to the situation better than before.

There’s no playbook for what’s happening right now, so that time and space is really essential to be able to deliver.

I’ve been teaching them and myself as well: just take a breath. The best solutions come with space and there are moments where the urgency is immediate, but recognizing the breath, both physically and metaphorically, allows you to take a moment and get the space you need to come back to the situation better than before.

What was a failure that actually set you up for success later in life?

I would say my failure to speak up earlier in my career. I was in a situation where I really believed that the organization I was a part of was headed down the wrong path. It involved a situation I was uncomfortable with, but I felt too new in my role and didn’t have enough confidence in my own perspective to speak up and say, “I don’t think this is right”.

In the end, I didn’t say anything, and the approach kind of went down the path I’d expected, and it was never something I felt comfortable with.

Later on in my career, I was fortunate enough to have a really great mentor and I talked to her about that incident. She was a very direct person, which I appreciated, and she said, “You know, if you’re afraid of getting fired in a senior people role, then you aren’t going to be able to be effective at your job. That’s something you have to be able to open yourself up to”, and I really took that to heart.

I’ve had to remind myself that many times and as I’ve gotten more confident in my career, I’ve learned to stand up and say things that have been in opposition to others. I still haven’t gotten fired, so that’s a testament to the leadership teams I’ve worked with.

With any executive role, the situations aren’t straight forward. But in people teams especially, there’s so much gray area in our work and we have to be willing to speak those hard truths and take what comes with that.

What are the best books, resources that have really shaped you as an individual?

So You Want To Talk About Race was a book we were actually reading as an organization at the end of last year. The way that it speaks to systemic racism through so many different lenses really broke through to me, especially as someone that has privilege and wasn’t thinking in these ways originally.

The Hard Things About Hard Things by Ben Horowitz is a great tool for coaching your CEO. Many of my CPO friends have read it on their own too, but the ones that haven’t, I always recommend it to them and it gives us something to talk about.

I’m a massive fan of Brené Brown and all of her research. All of her books are great. Dare to Lead is really specific to the workplace and is a compilation of all of her research, so if I could only recommend one, I would say that.

I follow her “clear is kind” mantra and sometimes it’s hard for me. Even though I mentioned I’m getting better at speaking up and saying the hard truths, sometimes in those moments, it can still be really hard to get that courage. That “clear is kind” idea is something that I use as my own personal pep talk when I have to have a hard conversation.

The last one I’ll say is Powerful by Patty McCord. I don’t know that I fully agree with everything she writes, but what I love about her and her work after Netflix is that she is very precise. She mentions how she pushed Netflix to be really precise in defining who they were and what their philosophy was going to be and, going back to systems, what systems were going to help reinforce those ideas throughout everything they did. It’s given me a more holistic way of viewing things.

What’s some bad advice you frequently hear in the people or HR function?

That the people team’s job is to make people happy.

This certainly wasn’t unique to my company [Sprout Social], but I first recognized this while at Sprout. We have such a people-first culture, and when I first joined, we had a strategic planning session as a team to articulate our mission. Everyone spoke about making employees happy.

It’s not that I don’t think it’s important for people to be happy - of course I want that. But if that’s your overarching goal as a people leader, you’re going to fail. You can’t make 100% of people happy 100% of the time. It’s a mission that’s doomed from the start.

We’ve since reframed our mission. Our role is to give people an opportunity to be and feel successful by having an impact on the business. I believe in my core that there is a human need for those two things: to feel successful and to feel like you’re having an impact.

So when we build systems, we have to take that into account, making sure that we have the right leaders in place and taking out any type of bureaucracy that might get in the way of people doing their best work. We also need ways to recognize that impact. Sometimes that means recognizing that they have a human need to be successful and have impact and that’s not going to happen here. Being able to make those hard decisions, sometimes people will make them for themselves.

People will leave our organization. They’re not going to work at Sprout their entire life, so in the time that we do have them, the goal isn’t necessarily making them happy all the time, but rather being a part of their career story and giving a great experience to talk about.

It takes a shift in mindset to get the team thinking like this. You have to start by having a direct conversation and saying, “That’s not it, and here’s why”. In terms of practical things we did, it helps to get specific at each department level, asking what success looks like. Reviewing career bands and rolling those out as well. That was a big thing for employees who wanted more transparency in terms of how to develop within their careers so in doing that, that naturally opens up the conversation to a lot more feedback.

As a result, we started setting up more systems for effectively giving feedback. We brought in LifeLabs, for instance, which is one of my favorite training providers and did incredible work with our teams. Feedback doesn’t make people happy most of the time, in fact, it often makes them uncomfortable. But while you may not be happy hearing these things, you have to realize how it can better your career.

The team then started to see that having your goal not necessarily be making people happy isn’t equivalent to making people miserable, in fact, it’s making people successful. So once they realized that, then they were able to get onboard.

[Joseph’s note: I found this particularly insightful. It speaks to the value that a CPO like Maureen brings when joining a new company - a fresh perspective that can have a transformational impact on the culture of the organization.]

It’s not that I don’t think it’s important for people to be happy - of course I want that. But if that’s your overarching goal as a people leader, you’re going to fail. You can’t make 100% of people happy 100% of the time. It’s a mission that’s doomed from the start.

Are there any resources specifically around giving feedback that you would recommend for the broader community?

The obvious one that comes to mind is Radical Candor. I’ve incorporated a few things from it, but I wouldn’t say it was as impactful as maybe the other books I’ve talked about.

What I would highly recommend is LifeLabs, which I briefly mentioned earlier. They’ve done an especially great job since COVID hit, offering complimentary, free sessions for CPOs and teaching lessons related to giving this kind of feedback as part of it.

Can you remember an epiphany, experience, or revelation you had at any point in your life, that changed the way you approached life or work?

Back in 2012, around when my first son was really young, I was an avid reader of Glennon Doyle, who was, at the time, a “mommy blogger.” She’s since emerged as a major figure in the D&I space.

She had written this one essay on the concept of time that has always stuck with me. At the time, it felt particularly relevant to me as I was raising an 18-month-old and when raising kids, most people will remind you to “cherish the days since they grow up so fast”, but in the moment, it’s a lot harder when you’re just wishing they’d finally fall asleep.

In her essay, she mentions these two concepts of time: chronos time and kairos time, coming from two different Greek words for time. Chronos time, she explains, is literal in its definition. It refers to that feeling of getting through the day minute-by-minute, the natural passing of time. But kairos time, on the other hand, represents those special moments when you realize you’re having a moment in the moment.

These moments don’t happen very often, and if you don’t intentionally look for them or make yourself open to them, then they don’t happen at all. For instance, this past weekend, the weather was beautiful, we had just moved into a new house, we finally had a backyard we could enjoy, and we were just sitting on our porch outside. On the surface, it sounds like such a mundane moment, and yet, it was so beautiful. This was kairos time.

Being able to actively recognize those kinds of moments and take a second to capture those mental snapshots can be powerful, especially in times like these. When COVID first hit, it was really stressful—making the switch to remote work, figuring out what to tell all our employees, questioning whether we were reacting too soon or too late. It felt like I was tasked with solving problems the world hadn’t even figured out yet.

It’s at this moment that I took a step back and thought to myself, “This is a career defining moment”. And not in a scary way, but in one that 5 years, 10 years from now, I’m going to look back on and really understand how much impact I was able to have and how much I’m going to learn through this experience. That’s where the power of recognizing the moment came in. It helped to take a scary time and put it into perspective, and I think perspective, right now, is the most important thing we can have.

[Joseph’s note: to find more of Glennon Doyle’s work, click here.]

What are your favorite questions to ask other people to get to know them?

I’m not a great small talker, so I find the most successful questions to be the ones that get the other person talking, particularly by asking them about topics they genuinely enjoy discussing.

Things like their children or their favorite vacations or a place they would really love to travel to are a few great examples. No one doesn’t want to talk about the great times they’ve had on a vacation, so as someone who is more of an introvert, I love asking questions that really engage the person you’re speaking with to keep sharing more about themselves.

If there were a Maureen Calabrese playbook for building a great relationship with your CEO, what would be in that playbook?

I’d say most of it depends on the individual. What I’ve found most valuable is coming from a place of understanding and empathy, which sounds odd, but remembering how much pressure CEOs are constantly under is incredibly important for effectively helping them.

I always try to create a mutual understanding between the both of us that my role as their CPO is to act as that safe space where they don’t need to have all the answers and where they can comfortably talk through their issues in a way that they maybe can’t with others. Kind of connecting back to the whole lesson of speaking up, part of my commitment to them is that I will always be the one to tell them the hard truths. Especially when an organization continues to get larger and larger, as the CEO, you become removed and people become more reluctant to be as straightforward or honest with you. I let my CEOs know that I’ll tell them what stings, and as a result, I’ve had to have some really hard conversations with people. Some have taken it really well, some have not, but once the moment’s passed and they’ve taken some time to reflect on what’s been said, they almost always come back grateful for it.

When you root yourself in that place of understanding and demonstrate that their success and wellbeing along with the organization’s success and wellbeing are at the core of your intentions, then you can continue to play that role and honestly commit to saying those hard things.

What’s an area where you’re still trying to grow and improve yourself in?

Presently, I’ve been really focused on understanding the hundreds and hundreds of years of history surrounding systemic racism and racial injustice. Diversity, equity, and inclusion at Sprout sits in my realm of work, and prior to all the recent events, I considered us to be further along the curve than maybe other people in understanding the concepts behind equity and inclusion. But in the last several months, I’ve certainly had to confront that I was wrong about that. That I really have no understanding in many ways of how pervasive systemic racism is and the ways that I’ve benefited from it, which has been hard to hear, but very important for me to do so.

It’s caused me to reexamine everything in my life. For example, I’ve realized that while I’ve done well in my professional life of showing up as an ally, I haven’t done it in my personal life in the way that I think I should. The way I parent has changed dramatically in three weeks and the conversations I’m having with my children.

I have a 10, an 8, and a 5-year-old, and to have my 10-year-old come up to me and say, “Oh, we learned about this in school, there was Rosa Parks and Martin Luther King. But it’s better now right?”, and realizing that’s what we have been—and are still—teaching our children, and that now I have to be the one to tell them that, “No, it’s not better at all”.  

That’s how I’ve been processing it from a deeper level, I’m proud of the work we’ve done but now, it’s about how we can drive that forward in our organization even further.

From a parenting perspective, do you have any advice for handling these difficult situations?

There’s two levels to it. The first is having those conversations that go beyond the history of it, and the second is really emphasizing the role they can play as allies.

Trying to find a way to make that age appropriate has been difficult. In June, CNN did a segment on how to talk to your kids about racism, and they brought in a few characters and experts to keep the kids engaged. This got me thinking about finding better ways to communicate these lessons in a more age-appropriate manner.

I’ve also been reflecting on how the choices we’ve made in our personal life have influenced those important lessons. We live in an area north of Chicago that is financially, a lot more stable than any of the surrounding areas. And we chose this area because of the great schools, which we could afford to do, and I’ve been seriously contemplating on how to grapple with that, and how that might also affect the children from a parenting standpoint. It’s something that’s bothered me for a long time, but what I now realize is that it’s not enough to be bothered by or feel guilty about it. It’s time to move past that to action. We’ve been having many more conversations with our children about privilege and how we can be using our resources to help lift other communities and schools. Watching all my children, even my 5 year old, understand that they have the power to drive change gives me hope going forward.

Joseph Quan, Founder & CEO, Knoetic | CPOHQ

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