How to engage and motivate agents: A Q&A with Dutchie’s Senior WFM
Ashley Pinales (she/they) is a Senior Workforce Manager at Dutchie. Like many who find themselves in workforce management, Ashley got her start as an agent. In this interview, Ashley shares why vulnerability is key to creating a positive work environment, how to create a culture of honest communication, and what role learning plays in employee engagement (spoiler alert: it’s not just for agents). Their answers have been edited for clarity and concision.
Q. Ashley, what personal experiences have shaped your approach to workforce management?
A. Having been an agent in the past, it’s not lost on me what those folks are doing. And it’s important for me to remember what it was like as an agent now that I’m the one in charge of forecasting contacts, scheduling agents, and analyzing queues in real time. As a WFM analyst or manager, or even as a department head, it's easy to get removed from the job you're asking people to do. I still have journals from when I was in the role, filled with memories of difficult customers or moments when I helped someone surprise their loved ones. I have very specific memories of being on the phone, troubleshooting an order that was significant to a customer. As a WFM analyst, you can forget the relationship your agents have with customers — and the relationship you need to have with agents.
Q. What’s your personal philosophy on keeping agents engaged and motivated?
A. For me, it’s first and foremost about being human. A lot of times, we default to more routine, process-type responses when interacting with teams. There's definitely a time and place for that, but when you can be yourself and show your personality, people really respond to it. The other part is asking and understanding what folks are interested in. Here at Dutchie, we offer agents a lot of development time with their manager. We received feedback that agents wanted more time to develop skills that don't necessarily pertain to their current role but are relevant to the roles they're aiming for. So, we developed an apprenticeship program where they can shadow our more technical teams or customer-facing roles like Customer Success Managers or Implementation Managers. This really helps hone their skills. From the WFM side, this also means going to bat for the teams and advocating for the shrinkage numbers we need to meet both the agents' needs and the fiscal goals of the business.
Q. Have you seen any impact on retention and career development from the apprenticeship program?
A. Absolutely. With the program, we've been able to create a pipeline for internal promotions. It’s not like the apprenticeship program guarantees a role right after, but it prepares agents for when roles open up. We've seen multiple scenarios where agents have applied for and gotten roles, even outside of the apprenticeship program, thanks to the skills and interactions they've had with other teams. It's been really cool to watch them flourish.
Q. Are there any unique or creative methods you use for training and development?
A. In our support leadership structure, we have team managers as well as CX coaches or team leads. Agents meet with them on a biweekly basis, usually alternating weeks. Within that framework, we've added more time for independent learning, so agents can focus on things they're genuinely interested in — even outside the apprenticeship program. We had a less structured form of this before, but it wasn't as effective because there was no plan behind it. Now, CX coaches interact with their teams more consistently and can tailor the experience — whether it’s watching a LinkedIn Learning course, focusing on a particular skill, or setting up a coffee chat with someone from another team. We make sure that time is utilized effectively and aligns with the agent's goals.
Q. How do you create a culture of open and honest communication?
A. Truthfully, this is an area I think I can improve on. I've always had an open-door policy — you can message me, DM me, send a carrier pigeon, whatever. I'm always open, and you can always ask questions. But my team recently reminded me that it’s one thing to ask for feedback and another to provide a platform for it. A lot of our team culture is shaped by the managers and coaches — they interact with the team more than I do, and they've established an environment where people feel comfortable speaking up. If something doesn’t feel fair, agents know they can ask questions or provide feedback. This open dialogue benefits the whole team. Now, it's up to me to provide a space for my own team to receive that feedback more consistently.
In WFM, there's often a perception that you're not going to be liked because you're holding managers accountable to certain metrics or sometimes saying no. It's easy to put your guard up and avoid live feedback, fearing it might not be constructive. But what I've been trying to do, especially over the last six months, is lean into the dissent and negative commentary rather than taking an egotistical approach of "that’s on them, not on me." Ignoring issues only makes them build up. Letting go of the idea that everything is perfect and recognizing the need for improvement fosters a culture of understanding. And I’d be shocked if any WFM manager or analyst said their processes don’t need improvement — business changes, and we have to change with it.
Q. How do you ensure feedback is constructive?
A. Rather than having a completely open forum, I believe it's about asking specific questions and sticking to key themes. A lot of WFM managers fall into the trap of thinking that if they open themselves to feedback, it has to be an open forum — but it doesn’t. I’m currently hosting feedback sessions with managers and coaches to identify the key themes that come up most often and then tailoring my questions to those themes. This way, we’re addressing what agents care about, not just the feedback I want to receive.
Q. How do you infuse fun and creativity into the workplace?
A. Our team has a lot of fun Slack channels within support and the company as a whole — including a meme channel and a dogs channel. I try to show a part of my life, whether it’s my dog, who occasionally shows up in meetings looking like she wants to eat me because I haven’t fed her yet, or other things going on in my life. I think it's really fun, and it helps build connections. Memes are also a huge thing on our team. When it came time to develop WFM training a couple of years ago, it was suggested that we include memes, so I did — and I made them all Ted Lasso-themed. It’s a bit vulnerable to share what you’re interested in or what you do outside of work, but our leadership team is really good about it. We have someone in a band who shares their music, and that encouraged me to start sharing my work as a wedding photographer.
Q. What role does technology play in enhancing your agents’ experience?
A. Technology plays a huge role. In the past, I’ve used tools that were very manual and caused a lot of wait time for us to review and approve requests. Assembled has been such a good change from the previous software our team was using. The Google integration is something we rely on heavily, and managers use it to schedule their one-on-ones, helping them be more accountable for their off-queue time. We also utilize the vacation request feature, and it’s so easy for my scheduling analyst to review requests and determine who requested time off first. Features like these give agents more ownership over their schedules. That and they’re not constantly waiting on action from my team.
Q. How do you define success in terms of agent engagement and satisfaction?
A. The easiest way to define success is through employee engagement metrics. While my team doesn’t have sole ownership of these goals and metrics, we definitely play a huge part in whether people want to work here. I’ve seen drastic improvements from where we started to where we are now, and it’s about keeping that momentum going. Another measure of success is how many agents participate in the engagement process. We have employee resource groups for different communities, like API or Latinx, and a Pride ERG. These groups allow people to get involved and meet new people outside of their daily work. Success, to me, is whether people who want to participate can do so and if they know these opportunities exist. It’s about making sure the important policies are front of mind and encouraging participation.
Q. What advice would you give to other workforce managers looking to find their unique approach to keeping the team engaged?
A. It’s easy to fall into the trap of thinking, “This worked at my previous company, so it will work here,” but that’s not always the case. You constantly have to keep developing yourself and taking feedback from the team. You don’t know what the team needs if you don’t ask. I also think it’s really important to continue your own self-development. Sometimes, if I feel disconnected from the team, I’ll take the same training they’re doing, whether it’s product training or something related to a recent launch. For example, when Ohio recreational use launched, I made sure to go over that process and understand what we’re asking from the agents. There are constant ways to evolve — whether through engagement, product knowledge, or understanding where more training is needed. It really boils down to putting yourself out there and trying.
