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Purposeful · Probative · Proactive - How to Retain Your Best People - Ep 6

[00:00:00] Emily: Hi, I'm Emily Fries-Kemney, host of Let's Talk, People, where leaders come to bridge humanity and profitability. Informed by a couple decades of work as a head of talent and leadership development, I'm here to amplify leaders so they can exalt everyone and everything they touch. Are you ready? Cause it's about to get real.

Let's talk, people.

In today's episode, we're going to talk about one of the things we struggle with a lot within organizations, which is retention. And I'm not going to make you feel much better about it. We are always at risk of losing our best people. A recent LinkedIn report found that over 60 percent of our employees are considering leaving their jobs at any given time.

And the percentage is even higher for Gen Z and millennials. The problem for us as leaders is we don't often know the real reasons and dynamics that are causing people to look and how to mitigate those retention risks. In today's episode, I'm joined by Heather Dolan, the SVP at Challenger Gray and Christmas, which is a premier outplacement firm.

She has spent over a decade advising and supporting organizations as they move through layoffs, restructurings, and leadership driven change. She is also the founder of the invitation-only Challenger HR Executive Group, which helps HR senior executives when they're going through moments of career transition.

That's where Heather and I met. It was an incredible experience, and it was one of the many windows I had into Heather's wisdom on this really emotional and challenging topic.

[00:01:52] Heather: Thank you. I'm very happy to be here. Thank you for bringing this conversation to light so that we can dig in and figure out how we can support people as they're looking to bring more humanity to work, and figure out at the same time how they can have their top talent stay and thrive.

[00:02:08] Emily: That's exactly right. And this is hard work. I don't think anybody's figured this out. I think we're co-creating a different future, a future that's more aligned to our humanity, our human needs, that actually does drive results. It's not in conflict. We know that when you create the right conditions for people, not only do they stay, but they thrive.

And that's what we're here to unlock. I love it. Let's dig in.

As a way to help us have this conversation about retention, we're going to use a framework. There's actually four different lenses to use to look at retention, and we've organized them into four P's. Purposeful, Probative, Prerogative and Proactive.

So first, Purposeful. When back the hearts and minds of those who are on the fence, how do you help to reconnect them with their why for your organization and their work?

Two, Probative. How do we really understand why people are leaving and not take things at face value? It's about unearthing what's really there to understand how you improve retention.

Three, Prerogative. It's not always the right decision to retain your best people. Sometimes the fit's not right, to the culture, to the role, or the conditions have changed.

And fourth, Proactive. We need to get ahead of our retention risks before people are already starting to walk out the door. We have a reference document with this framework that you can access in the show notes.

There's a link, or you can head over to a r o s e g r o u p. com forward slash resources. Let's get into it. Absolutely.

So let's start with Purposeful. Purposeful is about that connection that you feel to what you do, why you do it, who you do it with. It is the heart and it's the mind. It's the heart because if you don't feel something for your job, retention is going to be more of a risk for the organization. And if you love what the organization does and how it feels to work with your colleagues and the mission, but you don't feel that stimulated or challenged by the work you're doing, you don't have the stickiness either.

So what we really try to do when we think about the purposeful part of retention is it's not necessarily always just about how we sell people on why the work matters, why the mission matters, even though we do do that. And that is a responsibility of leadership and leaders. However, often our work is personal to us.

It's what's our “why”. And sometimes our “why” is very practical, which is to put food on the table and to have benefits, and to be able to one day put our kids through college. And sometimes our “why” is deeply meaningful, that we come to the work because in some cases we're healing something within ourselves.

So it is like deeply, emotionally resonance. And sometimes we do it because it's intellectually stimulating. It's fun. It's challenging. We're achievement oriented. We like to get things done. That's actually a natural part of who we are as human beings. And so this idea is that we actually enjoy to do our work.

However, when it doesn't all line up, it's hard to get people to stay. It's hard to get their best. Let me pause there, though, Heather. Anything you wanted to add or build on from there?

[00:05:33] Heather: Yeah, I think something we've seen in our business and industry, as we're working with individuals who are transitioning out of organizations and trying to figure out what's next for them, purpose comes up a lot.

And I think many times, clients might not use that word.  But I've never heard in my 13 years doing this work and working with thousands and thousands of clients, more clients post-pandemic saying, I want to work for a mission-based organization. Compensation is not the top driver. Of course, culture matters for sure, because it's wrapped up in all of this.

And that's what would create the potential mission-based organization, and be a draw for individuals. But it really is. I want to work for a company that's doing something good in the world. I want to feel good about what I'm doing at work. And I hear that. Every single day, which to me is really inspiring.

I think this is how we're going to change how we continue to figure out how we work, the types of companies we want to work for and work with and be a partner, no matter what level you're at.

[00:06:40] Emily: That's great. That makes so much sense. Let's keep going from here. So the other one is Probative. So Probative is we sometimes take the reasons that people say they're leaving at face value.

I think there's two reasons for that. I think one reason is people can be very convincing, and they'll say things that are emotionally resonant, which is need more flexibility, childcare, we're moving Like they're usually tied to a personal reason. And when people say personal reasons, we like to take it at face value, and there is often some truth in it.

But I can tell you, as somebody who did at a certain point, take a break and was at home with my children, that wasn't the only reason. When you love what you do, you figure out a way to make certain factors in your life work. So we all have our own circumstances, but I think we sometimes don't go beyond the surface of what people say. And, really probe at - is there more there?

The other reason I think we don't always probe - is there more there? - is because we're scared to hear what they're going to say. I think that none of us want to do a bad job as leaders and all of us are imperfect. None of us want to create the conditions where somebody feels like they can't be successful or their career can't grow.

And it happens. And I think sometimes it's our fear of the truth that holds us back from asking. But when we don't know the truth, we can't work with it. And I think there is a way, and this is a lot of the work that we do, and I did when I was in organizations during my career, and now on the outside working with clients,  is how do you gather those insights in a way that not only makes the people who are sharing it, both the people who have left or are exiting, and the people who are still there who you want to proactively retain, is how do you ask it in a way that makes them feel safe? And how do you share that data in a way where nobody feels shamed? I don't think there is learning that comes from shaming people. We know that with our children and our own lived experiences, like when you feel shamed, it shuts you down.

It doesn't create the conditions to problem-solve and to create different ways. So I think it's a way of gathering data that is both. Going for what's really their part and wanting to know that, and to deeply know that and then to be extremely respectful, and how that's then summarized, articulated, and shared so that it creates the conditions to want to work with it versus to want to push up against it, and either reject it or gets offensive.

Some of the ways to do this is through one-to-ones, focus groups, as long as the focus groups have people who are the same level, and there's no reporting relationship or kind of power dynamics amongst those groups, you can do focus groups. And then this idea of quarterly connections.

So we know we've moved in most organizations towards more frequent performance conversations, but this is not exactly the same. It can be in that same window, like in that same meeting, you can do this, but a connection is different. A connection is just like talking to somebody as a human being, not as like the work that needs to get done or how they're doing the work.  It's more of the, like, how are you doing? How are things going? Heather, anything you want to add there?

[00:09:51] Heather: Yeah, I think probably hand in hand with shame, is the fear as well. If you really want to get to what's going on, how are people feeling for those that are within the organization is having a big trust factor, and understanding that if someone is brave enough to share what's going on. 

It could be with their direct manager, it could be about their direct manager and they're coming to HR or trusted confidant to be able to create that safe space where they can share so that way they're not in fear of sharing their truth.  But also they're not going to just leave because they feel nothing's gonna be done, I don't have a place to go and share, and so it's easier for me just to leave, unfortunately.

[00:10:33] Emily: Yeah, I'll never forget really early on in my HR career. In the business that I worked with, two, maybe three, I think it was three members of the same team, including the boss, all came up and resigned. We had no idea.

It happened out of nowhere. We thought they were happy. It was a trading floor environment, so you could really kind of see the dynamics. We thought they were super engaged. They were like the life of the party, and they were amazing at what they did. We had no idea it was coming, and that is one of the worst feelings.

The people are gone. You cannot get them back. They've already made a decision. Hearts and minds are out the door.

[00:11:07] Heather: Agreed, because it feels like there's a lot of conversations going on that you are not privy to. That there's a lot of things going on in the background. You think everything's kind of moving in the right direction.

Meanwhile, people are plotting their next opportunity, and most of the time it's going to be a moving somewhere else.

[00:11:24] Emily: Yeah. And I think that this is a little bit harder with hybrid and remote work, but not impossible. But I think you start to feel shifts in people in terms of their engagement, their energy, even like how much they even contribute to a conversation, how much they ask to be involved in things proactively.

I think that if you really tune in and notice interpersonal dynamics at work, you can find some of the little breadcrumbs of where you may have issues. I don't even think it's the more obvious things like people unexpectedly having something that they need to deal with and like, Oh, they must be interviewing, right?

Or like their hair is fully styled today. Like, I don't think it's usually those obvious signs that are the most important ones. It is the slight shifts. And in engagement behavior and almost what I would call closeness, you can feel when people are starting to emotionally pull away from you as a colleague or for you as a leader.

We just often ignore it because we're busy or we just make excuses that they're just tired, the work's intense, they're just caught up in other things. But usually there's a sign there, I would say.

[00:12:35] Heather: I agree. And I think we have to have enough space and time to be able to have that interaction. And I think that's what's missing a lot of times. Especially in this hybrid and remote work, we're all just so busy doing, doing, doing that that time for connection is not there.

And so how can you really understand what's going on in someone's life if you're never connecting one-on-one? I also would say people not wanting to have those conversations, and pulling away from anything outside of, kind of, let me just show up and get my work done and sign off. They're probably not engaged in both their role with the organization, what the mission is of the company.

So, agreed. I think there's a lot of ways, but we do have to invest time to be able to see them.

[00:13:20] Emily: Yeah. And it's an interesting correlation with overwork, overwhelm, exhaustion, obviously, buzzy word, burnout. There's a correlation, but they're not the same. I think the correlation to where you were going, Heather, is that can be a sign that their attachment to the organization is lessening.

However, I think equally, people sometimes stay and stay for the wrong reasons when they're experiencing being overworked, overwhelmed, exhausted, because they're literally too tired to go get another job, which is not good either. So it's almost like two ends to the same sword: is that when they start to leave or is that when they stay, and as a former mentor and colleague used to call it, they resign on the job like they're there, but their hearts and minds are not there.

Regardless of which one it is, because we often are not going to know what it is exactly that's going on that is causing that bit of a shift in them, it still is the same solution, which is to take the pause and to spend the time there, and not to just push through it. Absolutely. Agreed.

All right. Let's keep it going.

Prerogative. So with Prerogative.  This is an interesting one because you might think at the surface level, why would you ever want to let your top performers go? I mean, it seems counterintuitive. I have seen over and over again that sometimes our top people also can get frustrated and cynical. Just because they're a top performer doesn't mean they're thriving and happy.

There's this thing, where sometimes when the work starts to feel repetitive —  the same challenges, the same issues — people start to lose their edge of wanting to solve them. For those of you who remember the movie Groundhog's Day, it feels like that, like as if you wake up and “I feel like I just am doing this over and over again”, and people just lose their will to find new creative solutions to problems. I think that's not healthy for that person, and I don't think it's healthy for the organization. Sometimes the environment is no longer the type that that person thrives in or wants to work in, and there's just a mismatch.

Some people love growth. They love chaos. They like the build. Some people love to like, refine and make things better. And some people are like, “I just want to like, keep this thing going and like, keep the steadiness”. Those are different conditions. And so if there's a mismatch, that's okay. We need different talent at different times. And clearly some of our biggest mistakes have been where we hire people and we got the fit wrong.

Like either, we sold them on something that really wasn't honest. And I think that happens a lot. I've personally had that in my career. I took a job and it's because of the stage of life that I was at, where like they said, they have such a nice culture. It was not the most progressive and innovative, but it was nice and soulful, and good mission, and had all the good feels.

And the culture turned out to be so different than what I expected, because often it's about like expectations and reality and when there's a disconnect between expectations and reality, it's really hard. So I almost feel like it's almost better to tell people the real reality of what it's like to work there, and you again,you don't have to say it in a negative way, because the conditions are only negative to some people. For other people, it's like, — “Oh, like that's what I do really well and in those conditions feel really comfy for me”. But I think it's about like, what is it really like to work there? That is important.

[00:16:45] Heather: And one thing I would add in here is I'm working with a lot of those individuals that are impacted by job loss.

And so many times they come back and say, “I should have left, I should have left a long time ago, but I didn't”. And we have to remember that most people don't raise their hand and say, “Hey, I want to go, give me a package. I want to jump into job search”. It just doesn't happen. Changes can be scary and certainly job search can be intimidating.

And I feel really passionate about this because I feel like sometimes people are really dying on the vine. They have so much to give and so much more to contribute, but just as you mentioned, the conditions aren't right. Maybe the leadership's not right for them anymore.

And so being able to be brave also and go to someone and say, “it just seems like you're not happy”, to be able to have that conversation, and for someone to then feel safe again, going back to the safety to say, “I'm not. This job isn't what I thought it was, or the culture.  I just feel like I'm not fitting in”, or whatever that might be.

And then how can we then help that person be their best self somewhere else? And what a gift to be able to give that person. But also, reflecting back on the organization to say what a gift was given to me, and what a great ambassador that person will probably be for that organization to say, “wow, they were able to support me in exiting”.  Maybe I wouldn't have pushed myself out of the nest.

But hey, it got me to this point, and I don't think I've really ever had a client who, once I landed a new role, said “Oh my gosh, I wish I was still in that job”. Most of the time it's like, I needed to go”.  This happened, but I do think it's not an easy decision, but that trust has to be the transparency.

Everyone wants to be successful and bring value. So I think it can be positive on both sides. But it takes work and it takes conversation.

[00:18:36] Emily: I love this so much, Heather. I think when we talk about humanity at work, that can be almost as conceptual as the idea of trust. You know, those words, it's like we throw these words around, like, what do they really mean?

I mean, the idea that you would care about a human being and how they're doing and their happiness, their well being, their best life outcomes and professional outcomes, more than your need for them and more than your desire to just have them keep showing up and getting the work done. Because it makes your life easier.

That is powerful medicine. Like what a gift to be able to be that human being and that leader, that you can overlook how it's going to impact you, which will obviously be very tough if they do decide to leave. But to see their heart, to see their needs over your own, is the ultimate goal we should all have as human beings for one another, and how we treat each other.

So, that to me is something for us to all meditate and think on is: just what conditions do we create in organizations and in the world by seeing people, and really seeing them in their needs? 

I think that's beautiful.  And then bringing it home: Proactive. So this is kind of the fourth element, Proactive.

How do you get ahead of retention risks? Three things here: role crafting, rewards crafting, and team crafting. As somebody who does org design, you're going to laugh that I say this, but I actually do think more often than not, for your most important people, your most valuable players, I do think there's something to be said for designing roles for them. I really do.

I think that if they are that incredible and you want to keep them, you can fill in around them. Because what I believe is that everybody likes different parts of the work. It's about putting the right team together. It's about the mosaic that we create together. So I do think that there are circumstances where the perfect idealistic org structure, org chart is less important than keeping the right people and giving them the responsibilities that allow them to enjoy what they're doing, and to continue to grow through learning and through impact.

So I do believe in role crafting for people, again, not in a way that means you can't get your work done and achieve your goals, like that's not efficient. But I do think there's ways to work around that by how you compose the team.

Rewards crafting. I think this is another thing that I see tremendous rigidity on in organizations, is that for ease of management, for ease of process, we try to create a way of doing rewards and everybody needs to fit into, when different things matter to different people. For some people, the benefits are the most important thing to them because of life circumstances, financial stability, family dynamics. For other people, it's that base salary even over a bonus and the fluctuating comp for others.

It's all about like “the more I crush it, the more I want to get paid, and I want to be able to be the driver of my own destiny”, even down to rewards being exposure projects. Some people are like, “don't give me any more. I can barely handle what I'm doing and I need the work life balance.  Others are like, and I was this employee back in the day of like, “put me on every special project that comes up”. The more diversity of the work, the more newness, the happier I'm going to be. So I think even how we think about rewards is in dialogue. I think we have too much rigidity around this, and I think that impacts retention.

And then also team crafting. Do not underestimate how much the team composition and who is on the team, impacts your ability to retain your top performers the closeness of that team, the collaboration, the support.  And I hate to say it, one of the primary reasons that top performers leave is if you put them with a bunch of duds or a bunch of underperformers, that is so demotivating to your top talent.

They want to be with people who are going to challenge them, stimulate them, uplift them, and who are playing at their level. It's like being on a sports team. Think about our children. They don't want to be the star playing on a team with kids who are still learning. They want to be with people of equal caliber. So I think that the team can often be the source of retention, or it can be the reason that somebody leaves because they're not with their caliber people.  And so holding on to your mediocre performers, low performers hurts your ability to retain your top performers, because they are not going to respect that.  And they're going to take on more work as well, which will then cause them to be resentful and burnt out and overwhelmed, because they're picking up the load for other people who are not performing.

[00:22:55] Heather: Absolutely.

[00:22:56] Emily: So these are just some other examples of ways to retain people proactively, give people exposure, promote and pay people before they ask. I can't tell you how many people have to advocate for themselves. Do you know how powerful it is when somebody's boss advocates for them before they even ask for it?

I mean, that is wow moments for retention. We talked about this idea of managing our low performers, and then the other is to make work fun and creative. I don't know when this happened in our history as a society that we thought having fun, laughter, joy equates to not driving high performance and getting a lot of impact and results.

It boggles my mind that that perception exists. I'll never forget many years ago, an email going around amongst a group of very senior executives, basically poking fun at the whole happiness movement. That's a bunch of, you know what, right? And I felt ashamed because I felt, well, I actually do believe in that, but I guess that's embarrassing and cheesy that I believe in happiness.

And now I'm like, “Screw them”.  Like that's why people leave organizations. I think fun is what frees up your mind to be creative, and to problem-solve, and to find new solutions, and to get unlocked. It's what makes you want to come to work. I think we need to work over index on finding connection and joy at work.

And that can be done on zoom. It can be done in person. It can be done through asynchronous chats and communities and collaboration.  And it gets done through doing work together and having a sense of humor about yourself and about the challenges you're facing versus the heaviness we often bring to it — heaviness and intensity. It's a way people do it, but I think joy gives you more energy and more life.

[00:24:41] Heather: Absolutely. I agree. I think we've just been in this space of we've got to get work done… there's so much work to do…. got to get it done, got to get it done. And we have forgotten that.  I know one of my first jobs, there was an annual picnic where all the families came, and it was a way to get to know not only the individuals, but have all the families come and have fun, and they then increased to doing quarterly events to get everyone engaged.

And it was just, we weren't hiding that we had children. We weren't pretending like we didn't have a spouse at home,  or other things going on in our lives. You could bring it all. And I think COVID did remind us a bit of that, of seeing our kids running around. I know I had many children in the background, sometimes not clothed properly and having to apologize.

And everyone said, we get it. It's the times now. And so I'm hopeful at least that I think we're trying to bring a lot of that back, where we can bring our humanity.

[00:25:35] Emily: Yeah, I agree. And once you feel like you understand people more and who they are and what their family is like and where they come from, I think it's easier to trust them.

I think it's easier to have more difficult conversations. I think it is part of the work to know each other and to take that interest, and to have those more human experiences of knowing one another more fully than just the bits that we get to see through getting the work done.

[00:25:59] Heather: And it also helps us have perspective too of what's going on.

Everyone who knows me or is listening to this conversation later knows I put most of it out there. If I'm having a day before I start facilitating, I just want to get it out. So everyone knows I might not be bringing, quote-unquote, my best self to the conversation, but I am always bringing my real self.

And I get a lot of notes that say, thank you for sharing that. And I'll get notes. “How's your son? I'm sorry. You had to run off to the doctor, or I'm sorry about this or that, or how can I help?” And that just makes me feel so seen and heard and valued. And like, I can continue to be authentic. And I think it also allows more importantly, people to feel they can be that way with me.

And that's how we open up to trust and bring in that type of relationship to work.

[00:26:43] Emily: And I think it goes all the way back to where we started, which is the number one factor in wellbeing is relationships. And that work is one of the most important sources of that. We join an organization for community. We do.

There's a lot of other reasons, but otherwise we would work by ourselves or we would do more gig work. But that need for community is such an essential human need. And I don't think we can underestimate how much connection matters and is a part of the work, is the key to retention and creating that stickiness.

[00:27:14] Heather: Absolutely.

[00:27:16] Emily: All right. We'll call it a wrap.

[00:27:18] Heather: Thank you. Thanks for this conversation today.

[00:27:20] Emily: Oh, Heather. I love sharing space with you, always. And I know I can speak for everyone who will listen to this that your wisdom is priceless and your heart shines through in your words always.

[00:27:36] Heather: Thank you.

[00:27:41] Emily: It was such a pleasure to have this conversation with Heather Dolan, someone who brings such heart and pragmatic action to this work of helping people through transitions. We encourage you to use this framework of the four Ps of retention with your team so that you can diagnose what are the things that you can do to improve retention of your top talent.

So again, it's Purposeful - winning back the hearts and minds of those on the fence.

Probative - how do you really understand the true reasons people are leaving?

Prerogative - it isn't always the right decision to retain people. There are times where it makes sense for people to go, and that's good for them and good for your organization.

And fourth, Proactive - how do you get ahead so that the retention risks don't own you?

Again, we have a reference document that we've provided that lays all of this out and questions that you can use

Thanks for joining today's episode of Let's Talk, People. For more info and insights, visit, and find me Emily Fries-Kemeny on LinkedIn and Instagram. If you're enjoying the show, please follow, share on social and leave a rating or review in your podcast app. It helps other listeners to discover us.

Well, that's a wrap, friends. Until next time, when we come together to talk people.

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