The Hiring Decision Most Founders Make Too Late
Most service-based founders don’t struggle to come up with ideas. They struggle to know which ones deserve a yes.
Dr. Caroline Adelman built Chicago Psychotherapy from a single caseload into a fifteen-person clinical team, a training program, and a body of work far beyond her original practice. Her story, shared on a recent episode of FoundHer Rising, holds two lessons that apply well past the therapy room: when to hire, and how to filter what you say yes to once you’re growing.
The Cost of Waiting to Hire
Adelman describes reaching a point where she was still handling every intake call for her practice herself, long after that task had outgrown her time. She calls the fix “the avocado rule,” a piece of advice from a mentor: hiring readiness works like an avocado. It isn’t ripe, isn’t ripe, isn’t ripe, and then overnight it’s overripe.
The lesson isn’t to hire recklessly. It’s to notice that the window where hiring feels comfortable rarely lines up with the window where it’s actually needed.
“If I had a redo on that, I would have hired that person six months earlier,” she says. It’s a common admission. Founders rarely regret hiring too soon. They regret waiting.
Why Founders Wait Anyway
The instinct to wait usually isn’t about laziness or denial. It’s about legitimate constraints.
Margins feel too thin. Early-stage revenue rarely has slack for a new salary line, and the fear of overcommitting is reasonable.
Trust feels hard to extend. Handing off work that’s lived entirely in your head, for years, is a real vulnerability, not a small one.
The work itself feels like proof. Doing everything yourself can feel like evidence you’re building something real, even when it’s quietly capping your growth.
Adelman’s practice grew past the point where any of these excuses held up. What changed wasn’t her confidence. It was recognizing that every hour she spent on work someone else could do was an hour she wasn’t spending on the work only she could do.
Systems Come Before Scale
Hiring alone doesn’t solve the bottleneck. Adelman is candid that documenting what lived only in her head was its own project, done alongside a newly hired clinic manager.
Three things had to happen before delegation actually worked:
- She identified what she was doing out of habit rather than necessity.
- She and her clinic manager put that knowledge on paper, turning informal instinct into a repeatable process.
- She let the new systems run without stepping back in to manage them personally.
That third step is the one founders skip most often. Building the system and then continuing to do the work yourself defeats the purpose. The system only pays off once you actually step back.
The Filter for What Comes Next
Hiring and systems solve the capacity problem. They don’t solve the second problem that shows up once a founder has room to grow again: too many good ideas.
Adelman calls this her “yes problem.” As a founder, she’s drawn to new projects. Left unchecked, that pulls her attention in directions that feel exciting in the moment but pull her away from the business she’s actually trying to build.
Her filter borrows a concept from leadership theorist Ronald Heifetz: the balcony and the dance floor. The dance floor is the day-to-day, the exciting thing right in front of you. The balcony is the vantage point where you can see the whole floor, including whether the exciting thing actually fits where the business needs to go.
“Part of my learning edge is forcing myself to stay on the balcony,” she says, “even when there’s cool stuff happening on the dance floor.”
She pairs that with a simple gut check: picture the best version of your business on one end of a spectrum, and the worst version on the other. Before saying yes to something new, ask which direction it moves you. If it’s even a half step toward the worst version, she pauses and sleeps on it before deciding.
The Common Thread
Hiring on time and filtering opportunity well are really the same skill, applied twice. Both require trading the comfort of the familiar for a decision that serves the business you’re actually building, not just the one in front of you today.
Founders who wait to hire are optimizing for short-term comfort. Founders who chase every bright idea are doing the same thing, just with opportunity instead of headcount.
The founders who scale sustainably are the ones who build a habit of checking both.
If you’re sitting on a hiring decision you’ve been putting off, or a growth opportunity you can’t quite tell is a fit, the questions Adelman uses are worth borrowing. Is this a step toward the business you want, or away from it? And if you keep waiting, what is that costing you that you haven’t measured yet?
This episode is part of the FoundHer Rising series, conversations with women founders in wellness, coaching, and consulting who are building businesses on their own terms.
Full Transcript
Christine Hakkola: Welcome to FoundHer Rising, the podcast for women founders in wellness, coaching, and consulting who are ready to build businesses that create freedom, impact, and income. I’m your host, Christine Hakkola, business coach, former psychotherapist, and mentor to women scaling service-based businesses.
Today I’m joined by Caroline Adelman, licensed clinical psychologist and founder of Chicago Psychotherapy. With over 15 years of experience as a leader, public speaker, consultant, and clinician, she specializes in evidence-based wellness and leadership strategies. Caroline, welcome to the show.
Caroline Adelman: Thank you so much for having me. I’m so happy to have you here.
Christine: We just had a big, long conversation before we hit record, and I’m excited to dive in and hear more about your story. Let’s start there. Tell us a little about your practice and how you got started.
Caroline: Sure. I’ve been in business almost 12 years, so there have been at least half a dozen iterations of the practice. I’ll tell it from the beginning and we can go different directions from there. When I started, I was a fairly newly minted psychologist. I’d just moved back to Chicago a year prior and had a newborn at home.
Christine: Wow, that’s a lot.
Caroline: I was also working part time in a school as their wellness director and teaching at a nearby university. That was a very small, part-time thing, because I loved clinical work and didn’t want to give it up, but I needed to rebalance my life. It went along like that for the first few years. I loved that I could do it at the dose I wanted, in the ways I wanted, with the clients I was best suited to support at that point.
Christine: If I can jump in, backing up even further, what made you start the private practice? Because you had some other stuff going on.
Caroline: When I came back to Chicago, I took a very full-time job, and I showed up four months pregnant to that job.
Christine: Wow, okay.
Caroline: I’m not a halfway person. I was filled with an entire caseload, then went on maternity leave, then came back and ramped up quickly. I was helping co-found a clinic. I was also teaching. It was all really great work with really great colleagues, but I was working way too much. It became clear to me, once I had my older daughter, that I needed to redistribute things in a way that gave me more control to toggle my priorities and my schedule.
Christine: I feel like a lot of my guests, and a lot of women business owners I speak with, have a similar thread. It looks different for everyone, but there’s often this sense of misalignment, of things being too much, of wanting a different lifestyle and a different way of showing up to work. Was that true for you?
Caroline: I think that’s right. I also know myself well enough to know I was going to want to keep walking down side paths. I get really excited about new projects and ideas. I’ve always been entrepreneurial. I was nine years old when I started running my first little jewelry stand business.
Christine: My goodness, that’s awesome.
Caroline: So in some ways it was inevitable I’d start a business at some point. But it forced the issue a little earlier than I’d anticipated, needing that flexibility and control.
Christine: Let’s get a bit more granular about your journey, since you’ve mentioned all the different moving pieces. In the first six months, what did practice look like for you? A lot of people listening are at that stage right now.
Caroline: People ask what the first few months were like as a mother and I say, I don’t fully remember, it was the same time for me. What I do remember is thinking I had to take it one step at a time, because there was no other choice. I kept having lunches with other women practice owners who’d been doing this longer, asking, how do you do this piece, how do you set up your LLC, how do you know the answer to all the overwhelming questions that come with starting a business.
Christine: You’re Googling stuff, doing it, hiring the right consultant.
Caroline: Exactly. Being able to remember that for every single person in those early days, you have to bat at something before you get good at it, and you only get good at it by putting in the reps. There’s a lot of messiness. I remember thinking everyone else must have had this figured out before they started, then finding that our struggles and challenges are actually pretty universal. I really benefited from the mentorship of people who had already done this.
Christine: We don’t actually need to learn it the hard way. There are so many people out there happy to give even free advice about getting started. What was the point, maybe not an arrived moment, but a first win or a realization that this was actually happening?
Caroline: I’ve had a few of those at different phases. Early on, I remember thinking, okay, I did it. I fairly quickly built the caseload I wanted, I’m doing good work with these clients, this feels good, and I’ve restored some balance to my life.
Christine: That’s huge. For a lot of folks listening, that’s the dream, having a full career and more balance. And then with any business, you have periods where things feel hard, then you get to ride the wave of what you’ve built, and then you decide whether to push into the next growth phase or stay where you are.
Caroline: Right, and every time you decide to push into something new, you have to anticipate working harder and not being as good at the new thing yet, because you haven’t put the time in. In each of those moments I’ve come to a point where I either thought, okay, we’re doing it, or I thought this was what I wanted but it’s not, and I need to switch gears again.
Christine: If you’re showing up doing the marketing and still not getting consistent clients, you might be trying to fix the wrong problem. That’s exactly why I created a free guide called the six reasons you’re not getting clients. It breaks down the six things that actually block client flow, so you can find the one that’s really in your way instead of wasting time on the wrong fixes. Grab the link in the show notes.
I want to ask about the twists and turns and the challenges, but first, you mentioned that early win of filling your practice. For most women founders, that’s the biggest struggle, client acquisition. How do I get clients, how do I find them, what do I say when they’re in front of me. What contributed to your early success filling your practice?
Caroline: A couple of things. Candidly, the place I worked the year prior had a strong local reputation, and I had a full caseload there, so there was already some word-of-mouth benefit before I opened my own practice. And in the course of that year, maybe more important for the long-term referral piece, I built relationships with other providers, pediatricians, psychiatrists, people who trusted the work I was doing and were eager to keep sending clients. That lesson has repeated no matter the size of my practice. It’s the people you build relationships with, who trust you as a person and trust the work you’re doing, who keep your business going.
Christine: More than nine times out of ten, when I talk with women in regulated professional services like therapy, that’s how it starts, through warm referrals and cross-referral relationships. I’d suggest anyone listening not underestimate the power of networking with people who are happy to send folks your way. Most of the time, that can fill a practice.
Caroline: Absolutely. This connects to your earlier question about the moment I thought, okay, we’re doing it. A couple years into having a group, a parent called and said she was ready for her kid to see someone on our team. I asked what she was looking for, and she said, I have to tell you, I was first looking for someone in my insurance network, but my friend told me you guys really helped her kid, and I ignored it for a while, and then my pediatrician told me about you, and then this week our kids’ school told me about you too. That felt different from individual relationships. It felt like being part of a community that trusts you.
Christine: That’s amazing, and it sounds like those referrals benefited both your one-on-one work and your group practice as it grew. Say a bit more about the group practice, because what a lot of group practice owners get surprised by is that what worked for building their one-on-one no longer works the same way for building a group. What were some early surprises or challenges as you shifted?
Caroline: Can I give the backdrop of how I shifted into group, because it’s relevant. I’d been teaching for a number of years at a local university, in a graduate counseling program. One of my former students, who I’d stayed in touch with in a mentorship role, reached out for coffee and essentially said, now that I’m independently licensed, there’s less emphasis on my growth, and I want to keep growing and learning, and she asked if I’d consider hiring her, because she knew I was already invested in her development. I thought, yes, for you, absolutely, she’s amazing.
Christine: You’d already considered her before she approached you.
Caroline: I hadn’t planned to start hiring yet. I probably would have eventually, but she was the right person, and it happened at the right time. She’s still with the practice eight years later. I couldn’t do any of this without her. Part of what’s made it possible to manage the challenges is that from day one of having a group, I really cared about the people in it and felt invested in their growth. The challenge on the other side of that same coin is that I sometimes feel a crushing sense of responsibility to get it right for the people on my team.
Christine: I can imagine that’s a lot of pressure. That’s something I hear from other practice owners too, the fear around that responsibility, knowing people depend on you and their income through your business. How do you handle that? What mindset shifts have helped?
Caroline: A few things. The point where this really came to a head was during the pandemic. Our group had grown substantially by then, and we had really great people on the team, still do, but the pandemic was like drinking from a fire hose for mental health providers. It was exhausting every day, and we couldn’t meet the need, no matter how many people we hired. That kept me up at night, the people we had to say no to that I couldn’t send anywhere, because everyone else I trusted was full too. I got really protective of my team during that time, because you can’t pour from an empty cup. My leadership responsibility in that moment was different than just running a business. I needed to create the protective container to take care of the people who were taking care of everyone else.
Something shifted for me then. I sat down with my husband one night and said I didn’t know how I was going to pull this off, and that I’d need to take a pay cut for a couple of years to increase a bunch of benefits, more paid time off, better healthcare, a retirement plan. I really thought about what it meant to take good care of people, and I wrote my team a note that night that we were a human-centered practice, and that meant humans were always going to be at the center of what we did, including, first and foremost, the humans doing the helping. We learned firsthand that without that, there potentially wasn’t going to be a business left to run, because if your therapists burn out, and even if you technically still have a business, it would feel like everyone was a shell of themselves. We all felt it, broadly, across the clinical world. The why became really clear. If we’re not here to take good care of people, what are we doing any of this for?
Christine: That sounds like a really important lesson that shaped how you approach your practice and your team. Were there any unexpected side effects, good or bad, from putting such a strong emphasis on taking care of your team?
Caroline: One really positive side effect is that people have mostly stayed a long time and have strong relationships with one another. Every time someone’s had a medical issue, a loss, a very human moment, I’m brought to tears by how my team shows up. There’s a culture of what a human-centered practice really means, and yes, we sacrifice for that sometimes, especially me as the leader, but it also means we all benefit from being in a system where our humanity is centered in every interaction and every decision. I think that’s a net benefit to everyone, and it’s been stabilizing for the practice, because people want to be in systems where they’re treated like human beings first.
Christine: I suspect some listeners just had a big aha moment. Sometimes the stuckness as we grow really does go back to how we’re treating the team we already have. In your case, you solved a client demand problem by taking better care of your team, and it had all these unintended benefits, making the business stronger and more stable, able to keep growing off that foundation.
Caroline: Yes, and it got me really interested in human-centered leadership, which became a side path, public speaking and consulting around it, because I saw the impact for the whole human system.
Christine: Say more about that. What does your business look like today, if someone came in and saw all the moving parts?
Caroline: There are a few buckets. The primary thing by far is clinical work. We have a team of about 15, give or take, depending on the time of year, because we also run a training program, so we have clinicians and a clinic manager keeping everything going. We have relationships with a few local universities and typically take two or three graduate students, train them in evidence-based practices, and offer low-fee services with them so we can create access for the community. We also have relationships with schools where we do professional development, parent talks, bringing wellness practices into the places where people are working and learning. I also do a fair amount of work with law firms. Someone read a blog I wrote during the pandemic years ago and asked if I could turn it into a one-hour talk, and it grew from there.
Christine: Therapists and lawyers do tend to attract each other, there’s definitely a need there.
Caroline: There’s a sense of lifelong learning infused through everything we do. We run a speaker series and a clinical training series, both for other clinicians and for our own team, plus general public speaking and community events. But the bulk of what we do is clinical work. It’s just not the bulk of what I personally do day to day, I have more of a mix than most people on my team.
Christine: It sounds like there are a lot of supporting branches around that clinical core, some designed to build community relationships, some feeding back into the practice, which is an interesting business model. One thing that doesn’t get talked about enough as a business grows, especially with a larger team, is the need for systems, documented processes so the information required to do a good job doesn’t live only in the heads of fifteen different team members. Talk to us about your learning curve on systems as your business grew.
Caroline: That’s a great question, and I feel like I’m still on this learning curve. One of the best things I ever did was hire a clinic manager. That also happened early in the pandemic, when everyone was running flat out and I literally hit my limit. I couldn’t figure out how to keep it all in the air.
Christine: You’re not meant to.
Caroline: I ran into that wall head first and realized I’d found my limit and needed to hire someone. That person and I worked closely to figure out what lived in my head, how to put it on paper, and how to build systems around it. Some were work management and task flow systems. Others were things like our intake process. Until 2021 I was doing every single intake call for the practice myself, which was totally unnecessary. I also had to figure out what I was doing out of habit rather than because it needed to be me, and start delegating those things.
Christine: Which is absolutely necessary early on, but eventually we have to let go of it, because it isn’t sustainable to keep doing everything yourself. And in the mental health field especially, there’s never really enough margin to feel confident hiring early.
Caroline: I had a marketing mentor once who compared hiring to an avocado. It’s not ripe, it’s not ripe, it’s not ripe, then the next day it’s over. The takeaway is, always hire before you’re ready. It’s hard when profit margins are low, or you don’t have a lot of experience, or you’re worried about fit and timing.
Christine: Absolutely.
Caroline: In some ways it’s a force of habit you have to break. I could have been seeing more clients. There was so much demand, but instead I was doing something I could have handed off to an administrative assistant, and giving more time to clients and to my team instead. If I had a redo, I would have hired that person six months earlier.
Christine: I can’t think of a time I’ve heard someone say I wish I’d waited to hire. It’s almost always I wish I’d hired sooner, because it brings so much relief. Building systems, getting things out of your head, letting go of control, is always a work in progress with a growing business, but you’ve already come a long way, with a clinic manager and real systems in place. What’s possible for you now that wasn’t possible in 2020 or 2021?
Caroline: That’s a great question. I get to go to the balcony a lot more than I used to, to take stock and be strategic. Another major shift happened when I hired the first employee I mentioned earlier, as training director. She took over and ran our training programs beautifully, and other people on my team have stepped into leadership and supervisor roles, taking on pieces that mean I’m not just delegating or offloading, they’re actually doing it better than I could. And that’s possible because they’re doing it and I’m not.
Christine: That’s an added benefit a lot of people don’t anticipate, because the initial hiring phase is really about getting work off your plate. But then a secondary piece often opens up if you do that first piece well, which is what else becomes possible, and how amazing that you now have people delivering things that never would have happened if you’d held too tightly to the reins.
Caroline: Right, and it means I have people to go to the balcony with. I’m an external processor, I like to think in community, to bounce things off people. It’s always a better outcome when I run it by people I trust. Being able to say, here’s what I’m seeing, what am I missing, what are you seeing, where do we want to go with this, given who’s on our team now, what their strengths and interests are, what makes this sustainable for the next five years, lets me keep humans at the center of the strategic process in a way that just wasn’t possible when I was underwater all the time.
Christine: Speaking of the next five years, what’s ahead for the clinic? More continued growth on the current path, or a different vision?
Caroline: I’m right in the middle of thinking through that, so good timing. The clinical work will stay and stay the bulk of our practice. I love walking into a room, giving a talk, and having people say it shifted how they think about leadership or the small things they can do to care for themselves. I’d love to do more of that, it feels values-aligned and high impact. I also just submitted a children’s book manuscript with a co-author last week.
Christine: So cool, exciting stuff on the horizon. Reflecting back on our conversation, with growth comes a choice about whether to grow at all, and then, if you choose to, a next learning curve. You’ve been through at least half a dozen of those already. As you look ahead, what challenges or learning edges do you imagine you’ll come up against next?
Caroline: The learning edge I’m bumping up against right now, and will probably continue to, is being able to make decisions that are strategic and aligned with a larger vision, instead of just individually exciting. I love chasing an exciting idea, and there are a lot of ideas that excite me. But I have a yes problem, and that’s my biggest burnout trend, saying yes to everything until I have too much on my plate. Part of my learning edge is forcing myself to stay on the balcony, even when there’s cool stuff happening on the dance floor.
Christine: I love that metaphor, the balcony and the dance floor.
Caroline: Ron Heifetz talks about that a lot with adaptive challenges. The other piece is staying aware, having guardrails, to notice when something is an adaptive challenge, meaning something more fundamental has to shift and the stakeholders have to be involved, rather than falling into the trap of treating it as a technical challenge you can just throw a solution at.
Christine: I appreciate you saying that, and I want to reflect back that what you’re describing is really common. I don’t think I’ve met a business owner who didn’t have a yes problem. I relate that to a phrase I use regularly in my work, bright shiny object syndrome. Founders are founders for a reason, most are visionaries, and we have no shortage of ideas. Ideas aren’t usually the issue. What we sometimes unconsciously pursue are the bright shiny objects, and those are what distract us from the things that actually grow the business, and often what stretches us thin, burns us out, and bottlenecks us. I see it from the very beginning, new practice owners saying yes to every opportunity and sometimes regretting it. There’s a balance in the early stages between growing the business and earning money, and having a clear yes or no for the work we take on, because there are consequences either way. What I’m hearing from you is that this doesn’t change with the stage of business. I’d add that for owners in the one to three million range, it often gets even harder, because the necessity to focus on what you’re actually building is what gets you through to the next stage. That bright shiny object syndrome, or the yes syndrome, is what keeps us stuck even though it was necessary for some of the earlier growth.
Caroline: I think that’s right. I really experienced that during the early pandemic years, when we grew too quickly. We had three sites and twenty-something therapists. It was the first time I felt like a manager instead of a leader or partner. I realized I’m a relational leader and that wasn’t the kind of growth I actually wanted. Every yes I was saying was a no to something else my time, energy, and resources could go to. That forced me to zoom out and say, just because I can build something doesn’t mean I want to build that thing, and if it comes at the cost of my why, I’m losing the plot. It’s been a helpful, if expensive, way to learn that lesson.
Christine: That feels like such a good note to close on. I want to reflect back your metaphor of the balcony, and add that what’s been helpful for me, and it sounds like part of your process too, is when we’re faced with those decision points, the choice of pursuing the next bright shiny object, coming back to why am I doing this, is this in alignment with our values, and knowing we can say no to things that aren’t keeping us on the path we actually want to be on.
Caroline: Exactly, I totally agree. Can I share one more quick exercise? There’s an exercise I used to do with clients that I now do with myself. You draw a spectrum. On one side is the very best version of whatever you’re evaluating, your business, your marriage, how you show up as a friend. On the other side is the very worst version. For my business, the best would be, we’re caring for each other, we’re rooted in our values, we’re taking good care of people, we’re following through, we’re accountable. The worst would be frenzied, burnt out, not strategic. When I’m making a decision, I ask, is this a step in that direction, or that one. If it’s even a half step in the wrong direction, I pause and at least sleep on it.
Christine: I love that. Thank you so much for sharing it, and for sharing your journey. There are so many wonderful nuggets in what you’ve shared today. It’s been such a pleasure speaking with you. If listeners want to learn more or reach out, where’s the best place to find you?
Caroline: Thank you for asking. Our website, chicagopsychotherapy.com.
Christine: Amazing, thank you so much, have a wonderful day.
Caroline: Thank you, you too.
Christine: Thank you, listener, for tuning in to FoundHer Rising. If today’s episode resonated with you, follow the show, share it with another founder, and leave a quick review, it helps more women find these conversations. You can connect with me on LinkedIn or learn more at HakkolaHorizons.com. Until next time, keep rising, and keep building the business that gives you freedom to live, lead, and create on your terms.
