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Retaining talent through The Great Resignation: A conversation with Desy Osunsade

by Imani Doyle (she/her)

Amidst the COVID-19 pandemic, Americans across sectors have been leaving their jobs in record numbers in what many are calling “The Great Resignation.” In November of 2021, the US “quit rate” reached a 20-year high.

To that end, On-Ramps Search Consultant Imani Doyle recently caught up with human resources expert and the Global Head of People and Culture at Imaginable Futures, Desy Osunsade, to discuss why this is happening and what employers can do to retain and attract talent during this tumultuous time.


Imani Doyle: Desy, thank you so much for speaking with me today. Can you share a little bit about who you are and what your role is at Imaginable Futures?

Desy Osunsade: Yes, I am the Global Head of People and Culture at Imaginable Futures, an impact-first global philanthropic investment firm driven by the belief that learning is key to creating equitable, healthy systems. I started in October of 2020, so I’ve been in this role for about a year and a half. I was actually placed here by On-Ramps, so shout out to On-Ramps. The “people” aspect of my role encompasses supporting the organization with everything from recruiting to benefits, payroll, and employee relations. I also have the honor of serving as a resource to our portfolio partners when needed. Like many HR professionals, I wear many hats in my support of the team, which has been especially interesting with the pandemic and everything else that’s happening in the world right now. 

Culture is a huge part of my role too, which has been central to Imaginable Future’s COVID response because we, like many organizations, had to go remote pretty quickly. So, we’ve really had to think through how we continue to build the culture and the connections that we all need to thrive.

Imani: There've been a lot of articles and podcasts about the idea of The Great Resignation—or as some call it, The Great Opportunity—during the pandemic. Have you seen that affect Imaginable Futures either in terms of hiring new employees or retaining current employees? 

Desy: Although I personally know many people who have been involved in “The Great Resignation,” we have been very fortunate at Imaginable Futures to have retained all of our employees during this time, perhaps because we're such a small organization, and we really do feel a lot like family. It's just an incredibly generous and caring place to work. 

Imani: Is there anything in particular—a secret sauce if you will—that has helped you retain employees?

Desy: Yes. The first thing is that employers need to show that they really care about their employees as people, especially now. I was interviewing for my role at Imaginable Futures in the Fall of 2020, right after the start of the pandemic and the murder of George Floyd, so it was a really hard time for a lot of people and there was a lot of energy around social justice. The questions that I asked—and that I encourage all people to ask when they’re interviewing now—were: First, how have you supported your employees during the pandemic? And second, what did you do when George Floyd was murdered? How did you support your employees? How did you navigate that?

To me, the answers to those questions really say a lot about an organization’s priorities and culture. At Imaginable Futures, while we certainly didn't get everything right, there's a lot that we did get right with our response. I think our employees saw our response and felt validated that they were in the right place. That's certainly how I felt when I joined. Our staff survey data showed overwhelming satisfaction with how we handled both the pandemic, and the social and political events of 2020 and 2021. Those are incredible results!

Imani: You mentioned checking in with employees and receiving feedback surveys. Was that something you were already doing before the pandemic? How would you recommend other organizations collect and respond to employee feedback? 

Desy: Well, Imaginable Futures’ launch coincided with the start of the pandemic.  As a result, we’ve done engagement surveys from the beginning. Then, last year, we realized we needed to touch base with staff more frequently, so we added in a shorter, more frequent  pulse survey to check in on the well-being of our team. So yes, getting  a sense of how the team is doing via surveys is critical, as is what you do with that information.

One advantage we have is that we’re a small team. We have less than 25 team members globally, which makes it much easier to check in with everyone. I try to have one-on-one check-ins every month with every employee. 

But, one-on-one check-ins are still possible—and important—at larger organizations. I actually started doing one-on-one check-ins when the pandemic started at my previous organization, which had many more employees. To accommodate the number of employees, I couldn’t do an individual check-in with every person every month, but I carved out time to make those one-on-ones a priority. 

I call these check-ins our “nothing time” because what I'm trying to do is recreate the water cooler, break room conversations we would have if we were in person. So the format is very loose. If there's work stuff to talk about, great. But oftentimes we’ll just talk about how they’re doing or what they’re binge watching. Sometimes I’ll literally pull up their calendar and just say, "I don't see a break for you for lunch, what's up with that?"

And so, that's certainly something that I think has helped—staying connected with the team, knowing how people are feeling, where people are struggling, and listening to people. Sometimes people will say, "I really appreciate having this time where it's not work focused”. We're just talking about Housewives of Atlanta or something like that, but people really appreciate that break in the monotony.

Imani: That really resonates. I never thought I'd be the person to say I'm ready to go back to the office, but I really miss having those conversations with folks. Zooming out a bit, why do you think The Great Resignation is happening now?

Desy: I think a lot of it has to do with the pandemic. Early on, all you saw on the news was the number of cases and the number of deaths. When you're confronted with that—especially if you're someone who had one or more family members or friends pass away—it really wakes you up. You start to reflect on your life and think more deeply about your career: ‘Am I at an organization without a growth path, inadequate compensation, terrible hours, or a boss who doesn't seem to care about me?’.

These are all things that at one point we were just muddling through because that's what we thought we had to do. But with the pandemic, I think a lot of people had a moment where they realized that life is short and they want to maximize the time they have left on earth. I really think that’s what it comes down to, particularly for the people who resigned intentionally without a job lined up. Some people resigned for a better job, but many people resigned and had nothing. 

The American workforce, and even the global workforce, is prioritizing themselves above career. People are moving back home, taking up hobbies or trying to turn hobbies into careers. They’re willing to forgo some security and try things outside the norm. In response, all these organizations are realizing that they have to work harder to retain their talent.

For instance, Target raised its hourly wage. In general, retail jobs and service jobs have never paid more. And it's not because these companies are generous. It's because they need talent and it's hard to find.

Imani: What impact, if any, do you think The Great Resignation will have on the future of talent management and human resources? 

Desy: One thing, that is really a reaction to all of the events of the past two years, has been organizations ramping up their diversity efforts, some of which are real and some of which are rubber stamping. In addition, as I said, compensation is going up because it has to in order for organizations to attract and retain talent. 

The other big thing is investment in well-being. I was talking to a colleague the other day about how most benefit plans have an employee assistance provision. We call it an EAP, employee assistance program. It’s usually at the bottom of any benefits package and people rarely used it or even realized it was there. But now, more people are taking advantage of EAP’s because they offer things like mental health resources and other life resources like nutrition help, parenting resources, etc. Now, as mental health is starting, for the first time, to be a priority in the workplace, these benefits are becoming key parts of benefits packages. It’s something that I believe people will actively look for in a benefits package going forward. 

At Imaginable Futures, we started offering a lot of these benefits early in the pandemic. In the first year of COVID, we recognized that our staff needed time to disconnect. We started offering what we call “rejuvenation time,” where we just shut down. We're one of the first organizations to shut down for an entire week. We have long weekends. We're off this Friday, actually. And we did that because we heard from staff that even when they’re on PTO, they can’t really disconnect as long as they’re still getting Slacks or emails on their phones. So we decided that we needed to just shut down the whole office periodically to let people have that time off without having work in the back of their minds. So we have a couple of long weekends where we shut down on Friday. And then we have a whole week off at the end of June.

And we encourage staff to find outlets that will bring them rejuvenation and joy. In the beginning we actually gave staff funds towards that, which I think is another trend. I was reading about a really big company, I think it was Ernst and Young, who started budgeting funds for staff to spend on things that bring them joy and give them peace. I predict we're going to see more and more companies prioritizing well-being efforts in a way that only the top 5% of companies, primarily in the tech sector because it was so competitive, were doing previously. But now every industry is competitive. And I think you're going to start seeing more of that to the betterment of the company and the employee.

Imani: You’ve shared a bit about what Imaginable Futures and other organizations are doing, but what would you say are the best practices around employee retention more broadly? What advice would you give employers?

Desy: If you want to keep your employees, you have to make them want to stay. And the way that you make them want to stay is make them feel valued. Where possible, provide them with a career path or provide them with growth opportunities. Certainly treat them well as people. It goes back to what I was saying earlier about questions that prospective employees should be asking during interviews, "How are you treating your employees?"

My advice: pay well and offer great benefits. I think that any organization that takes that perspective, as we do at Imaginable Futures, truly cares about their employees as people.

These are some key things that, frankly, employers should have always been doing. But it's the perfect example of supply and demand. When the demand for talent is high and the supply is low, you really have to get creative. And so, I hope that this is here to stay because this is how it should have always been.

Imani: It seems that a lot of the concepts that you’re talking about require buy-in from the entire organization starting with leadership. How do you get that buy-in and why does it matter?

Desy: Nothing really permeates an organization without leadership and buy-in. And certainly, at Imaginable Futures, we're very fortunate that our leadership and board are very people-driven and care about us as individuals. But I think it’s not only about getting leaders to buy in ideologically. It’s not even only about where you’re budgeting your money and what policies you’re setting. The biggest issue that many organizations face with their leadership is making them understand how their actions set the precedent for other employees. 

And I'm talking specifically about cultivating work-life balance. Leaders can say “we want you to rest more and really make sure you have a work life balance”. They can even create policies encouraging that for their employees. But if the leader is the one sending out emails at 10:00 PM or working on the weekends, then they’re undermining those policies and their words. It's not what you say as a leader, it's what you do.

Imani: Is there any other advice you’d give to organizations who are concerned about retaining their employees? 

Desy: The biggest thing is listening to your staff and involving them in finding solutions. Not to say that you have to do everything your employees say. Sometimes you just can't. But you never know what great ideas might come up that you hadn't even considered. Use engagement surveys, ask for suggestions, and keep communications open, and coach managers to make listening a priority.

There's never been a more challenging time for leadership. There's never been a more challenging time for human resources professionals. There's never been a more challenging time for managers. We all need support from one another.These times are unprecedented in our lifetime; it can all be overwhelming. A great place to start is from a place of open communication and empathy.