In this episode, Anne Jacoby, CEO of Spring Street and author of Born to Create, dives into the importance of Creativity Legal. Together with host Stacy, they explore how creativity can help lawyers rethink traditional practices, overcome common creativity blockers, and handle crises with fresh perspectives. Anne also shares her journey in the legal field, from starting at Axiom to now guiding legal teams to embrace creativity and thrive. Tune in for insights on transforming your legal department’s culture and approach.
—
Listen to the podcast here
Why We Need Creativity In The Legal Department – Anne Jacoby, CEO Of Spring Street And Author Of Born To Create
Introduction And Why Creativity Is Important For Lawyer
On the episode of the show, I’m excited to welcome Anne Jacoby. She is the CEO and Founder of Spring Street, which is a workplace culture consultancy. She’s the author of Born to Create. We’re going to talk about why creativity is important to the legal profession and help lawyers level up. Anne, how are you?
It’s great to be here, Stacy.
I’m really excited. As I was thinking about this episode, I didn’t know that lawyers necessarily realize that creativity is an important ingredient to their practice. I know you’ve worked with lawyers for a very long time and I thought it would be good to give a little bit of the why, how you got to this place, and how it dovetails with the legal profession.
Anne Jacoby’s Career Journey And Working At Axiom
It’s a great place to start for context. I joined Axiom in New York City in the early 2000s. I was the seventh employee. At the time, I didn’t know much about law. I didn’t know much about business. It’s really like learning a whole new language. I started really by empathizing with what the general counsel, what in-house counsel was faced with, and what they were struggling with. At that time, it was really about doing more with less, not dissimilar from where we are now.
My how times are the same.
Isn’t that interesting? Needing to do more with less, we really focused on how we can rethink the traditional ways of consuming legal services. I love that Mark Harris, the CEO and founder, talked about throwing the law firm in a wind tunnel and stripping away all the excess, the overhead, the stuff that isn’t necessary to perform high-quality legal services and reinvent this new model firm. Now, Axiom has created this category. It’s very common to lean on alternative service providers, but it was pretty novel at the time. I think that really got me interested in getting folks to think differently and creatively about how to run their law department like a business.
Maybe some specifics about like, because it’s a great idea. I would be a customer where I cannot afford headcount or big white shoe firms are too expensive and need help with commodity or medium work. How did you help them take that great business idea and turn it into a reality?
It was really about understanding what work needs to get done, how we segment the legal demand into different categories, and then thinking creatively about leaning into different options in different categories of work. Maybe you have a big M&A transaction and you could really use an extra pair of hands to do the due diligence. You’d succumb to a lawyer. Traditionally, you’d bring a lawyer may be from a traditional law firm, but now you have this alternative where you have someone who has the same experience.
The same lawyer from that law firm, but working in a different way. I think that it was really groundbreaking at the time to think differently and creatively. Also, it provided this window into people who are really experienced and really at the top of their game and can choose a different way of working. It’s not uncommon now for folks to say, “I’m only going to work three days a week, or I’m going to work really hard and take my summers off.” That’s more commonplace. At the time, it was extremely novel.
I’m having a little bit of a flashback to that period of time, and I just saw a LinkedIn post with somebody talking about a conversation they were having with a law student who was looking at big law, and this is the next thing. I just remember feeling like this is what you do. You graduate from law school, you work at a really good firm, you have your head down, you become a partner, and you just bill hours. You don’t take the summer off. You don’t go to a different alternate service provider because that’s getting off the track.
The stigma has really been eroded, which is wonderful that there are much many more options now, I think, for really exceptional lawyers in the field.
The stigma of leaving big law has eroded. Exceptional lawyers now have more options to work differently and still thrive. Share on XMaybe you could say how big was the firm when you got out of that.
I was with Axiom for about twelve and a half years and opened up new markets and was the general manager of the Southern California practice. I really rode that rocket ship for a long time. By the time I left, there were thousands of people around the globe. It really did scale.
I want to say that you know about which you speak, which is that you understand lawyers, which is different, I’m sure because I know you had a creative background in theater and performing arts. To get to people who are pretty tightly wound, have super high standards, hypercritical. I’m wondering if you could share a little bit about that experience. What did you learn, and what did you observe about lawyers that fed your work today?
It’s interesting. My sister’s a lawyer. My late aunt is a lawyer. I have many close friends who are lawyers. I get this community. Although I’m an MBA group, I really admire how lawyers, especially those coming out of law school, are taught to think critically. It really helps train the brain to follow logic and make a case. It’s incredible to witness. I think today’s lawyer really does need creative thinking.
Creativity and critical thinking go hand in hand. To navigate today's fast-changing world, lawyers must think creatively to mitigate risk. Share on XWe’re forced to mitigate risk in new ways, business is changing faster than ever. It really does take someone to look around the corners and think creatively about, “How are we going to negotiate this contract? How are we going to mitigate this risk?” Whatever the crisis may be in the moment, it takes creativity to solve that problem. I really like how the lawyers that I admire, the lawyers that I’ve seen really succeed in their craft, and think creatively every day. They may not use the term creativity, but that’s really what’s being applied.
Overcoming Creativity Killers In The Legal Profession
I caught on thinking critically and we’ll talk about your book in a little bit, but you write about creativity killers. I had to observe that many of the creativity killers that you identified are ingrained in lawyers overthinking perfectionism, making early judgments, and having a fixed mindset. I don’t know if this resonates with the audience, but certainly guilty on a couple of these killers. How do you recommend that lawyers reconcile these inherent traits with what’s needed for creativity?
I think it’s not just lawyers. I think it’s anyone who has succeeded, risen in the ranks, and been elevated to this position of leadership. It’s usually because there’s an element of, “I got this right and I know things.” All of a sudden, you’re in this leadership position and it’s actually the opposite that’s going to make you successful. It’s the, “I don’t know the answer to that.” It’s the humility of, “Let’s figure this out together.”
That curiosity, the beginner’s mind, acknowledging that you still have stuff to learn. It really does take a shift in mindset to think more creatively and bring that curiosity to the work that you do. If you think of Adam Grant’s book, Think Again. It’s all about rethinking and unlearning that’s required of leaders today. I work a lot with chief legal officers, general counsel, and chief compliance officers who are really trying to practice those leadership traits.
Let’s talk a little bit specifically about how you work with CLOs and GCs. I assume that there’s a big culture component of this since we let off that your firm is a workplace culture consultancy. How would you assist a leader in a legal department in rethinking how they run things?
Rethinking Legal Department Leadership And Culture
I do think it comes down to the dynamic that’s created within the team. Really understanding how does the team operates? How do they gel as a unit? Where are there opportunities to change behaviors or processes? A lot of times, it’s just that the structure isn’t right. That’s limiting people’s ability to think creatively and do their best work. I work a lot on the strategy of culture and partnering with heads of law departments to try to move in a better direction so that people can feel the joy of co-creating. There’s so much great research and data that points to how fulfilling that is. Let’s enable that.
One of the chapters in the book talks about space, like even having the right space for creativity. Can you talk about that?
There’s physical space and then there’s just time and space. I think both are important. A lot of times, we’re in back-to-back meetings and there’s no time in the day.
By a lot of times, do you mean every day?
Pretty much, right? That’s our reality. There’s really no time to process all of the good stuff that’s happening.
Even to write your to-do list because every meeting and every back-to-back comes with three different pieces of homework for the lawyer on the call.
I’ll share a common term, and it’s overused, but not work harder, but work smarter. That’s really necessary. I think it’s about working more creatively and thinking about, “What work should I not even be doing at all? What processes can we retire? Where should we rethink? We have this recurring meeting, but is it still necessary?” It’s all that process-related stuff that can shift the tide in terms of how much space people have to think creatively.
I would think that even taking a step back and looking at your processes signals to the team that we care about making space for creativity and that we care about your well-being. Look, the US Surgeon General issued a warning about how parents are exhausted and burned out. It’s no joke. That was a little late, I guess. I mean, I’m happy somebody said it.
At least it was acknowledged.
It was acknowledged, yeah.
We really do need to pay attention to these things if we want the best out of our team.
When we talk about the spaces for creativity, both making time in the calendar and a warm space for creativity, I think I had a think back to a conversation I had with Sterling Miller, a longtime general counsel. He’s a thought leader in the in-house space. He shared that when he would get a new project or a new issue that would come from his leadership team, he would bring his GC team to a conference room with a whiteboard. He would just say, “What are ten things we need to do? What are ten things we need to learn?” Just really not moving away from that space of having to know the answer and having to create a process about how to figure out the answer.
I love that. That is just classic brainstorming and creating the space for that. What I love about that is that Stacy is a lawyer, I think, who is often in the position of needing to say no, maybe in a gentle way, but it’s about managing risk. I think if we shift the mindset to what the possible paths are to yes, it really is. You start to seek out the possibilities, and all of a sudden, you start to see more possibilities because your mindset is oriented that way.
On the mindset topic, I just interviewed Kate Dugan, who’s the general counsel of Energizer. She said that their team approach is not to say no and ask how, which I thought was a great creative nugget.
Absolutely. I always borrow from the improv world and say yes and so what could it look like to build on each other’s ideas?
I want to go back to the creativity killers and I’m thinking in particular about perfectionism, especially from that law firm training. I don’t know if this was that way at Axiom or if it was more practical, but in the law firm, if you had a comma out of place on client communication, it was not good. You got conditioned that the work product is perfect, which is actually a good thing, except in a real company that can be a business stopper in addition to be a creativity killer. Do you have a specific exercise or ideas on how to work through the perfectionism killer?
I think just supplying the 80-20 rule and just understanding that the speed of business requires done is better than perfect. It’s just you got to keep moving. I think little exercises like that can help us to move through. Celebrating those movements, you want to reinforce the positive and the good that’s happening in your team. If you’re noticing that there is a perfectionism issue, how can you celebrate and reinforce all of the times that you just move through it, even if it wasn’t perfect? Then people start to recognize that, “It’s okay.”
I don’t know if I’ve observed this at the time as perfectionism, but when things were taking longer, if someone on my team had something for a long time, I would check in and try to peel back like, “What is it? Are we overthinking this?” Sometimes, that would come out to like, “I really don’t want to make a mistake.”
Yeah, or I just don’t know the how. I don’t know how to move through it. I don’t know who needs to be at the table here. That can be a source of inertia. Just get stalled out.
One other thing I wanted to relate to is that you talked about how critical-thinking lawyers are trained to be an issue spotting mode. I don’t know. You go to a new staff meeting or a product launch, and the lawyer needs to sit there in their hands and not say anything because a million bad ideas are going to come out. Do you have advice for lawyers on how to manage that instinct to just rain on the parade and point out the flaws in new ideas?
I do think the yes and really works well and really taking it to crazy places like, “What if we built this product on the moon?” Just thinking really big and just allowing yourself to go there can loosen up that more constricted sense of, “It’s got to fit into this box,” but it’s probably not going to fit into the box. Let’s just get out of the box and then we’ll make it work. We’ll make sure that we’re managing risk in a healthy way because businesses are going to have to take on some risk. It’s all about what risks are tolerable for a given time.
I think that’s probably one of the biggest challenges that people have when they move to an in-house environment and even to be able to progress in an in-house environment because there is just so much training to avoid risk and let’s come up with this perfect solution. Really at the end of the day, that’s going to be like, don’t do anything.
Isn’t that risky? I think that the funny thing is that people think, “We’ll just retreat to what’s been done before the status quo.” That’s our safety zone. Actually, in reality, that could be the biggest risk of all is not changing and not adapting, not trying something new. I think that we constantly have to think about is that really the safest option, especially in today’s environment.
I think I shared when we were prepping for this. I had a conversation with a friend recently where I talked to a lot of people through the podcast, I do a lot of reading, and I’ve had this idea r to write about an issue that happened in my career. She just said, “You could never write about that because of the attorney-client privilege.” It was like, “That is such a bummer. Way to take my energy and joy away for this passion project.”
Dream killer.
Yeah. Not even just creativity but dream killer. What about advice for the folks leading departments to get over that kind of let’s not call it dream killer, but that instincts to reign on the parade?
I really like the imagination of the story, getting folks in a room, and really imagining what this department could look like. Let’s think big. Getting people in that space of possibility to imagine, “Our team is this size right now and doing this type of work. Let’s reimagine five years from now, what could it look like?” When you leap forward into the realm of possibility, some really interesting stuff can happen and emerge, and all of a sudden, you can coalesce around a new future vision and start to move in that direction. Maybe you’re not there yet. Maybe it is five years down the road, but living in that state of possibility can be really energizing for the team.
Do you have it? Can you share any examples of leading a legal department through that exercise?
I have several clients who are at a point of transformation and who have gone through major growth phases. We’ve definitely had a chance to lock arms around what this future potentially looks like. What are the initiatives that will support the vision and mission of this team? I always like to start with that vision and mission. Obviously, core values, how we’re going to get there, how we’re going to partner together. That really helps people to imagine that path forward. I do like starting with that big-picture thinking.
I’ve got to say, in my experience, law departments don’t always take the time to do that. Kudos to your clients who have, and I’m sure they’re thrilled to have somebody who’s led other teams through that work. You can almost see the people twitching when I’ve done retreats or focused team development. They want to look at their phone and get to those emails. It’s a hard thing many times for lawyers to step back and look at the bigger picture.
It’s a new muscle and maybe an underdeveloped one.
Earlier, you mentioned how creativity is important in a crisis, and you wrote about a couple of examples in your book. If you could, I’d like you to share some stories about and why you think creativity is really crucial in a crisis.
Creativity During Crisis Management
I think when you’re at that point of crisis, again, I talked a little bit about retreating to the status quo. When our amygdala is fired up and we’re in that fight or flight zone, it’s really easy to think, “I’m just going to go to safety. I’m going to retreat.” That’s often the time to reimagine how could we move through this in a new way. What hasn’t been explored yet? In the book, I talk a lot about how you can reinvent, especially as it relates to culture, a path forward that maybe has never been done before or is a new initiative or is bringing people together in new ways. It’s that reimagining zone that I think can help move teams through a crisis healthily and get people in that generative state of co-creating a better path.
There is that old adage, don’t waste a crisis. I had Jen Brewer of Activision Blizzard on the show several months ago. We talked about ways to play heroes, and that’s actually how you and I connected. I know you supported Activision and Jen in developing that program. You want to talk a little bit about that because that’s a great example of exactly what you’re talking about.
Jen is the master at this kind of thinking and new ways of building a speak-up culture. In that case, it really brings together ethics ambassadors from around the globe from all different parts of the business to advocate for doing the right thing. She did it in really novel ways, with new programming, training, and engaging employees. It’s really been an honor to be a part of that journey and bring it to life.
I know that she’s won some awards for the program. I would just say, I’m sure this is preaching to the choir, but crisis management is just a core accountability, a core function of the legal department. Usually, if there’s a crisis, an employee issue, media, core regulatory action, or something that is a threat to the company, Being prepared and able to use all your skills, including your creativity, is essential.
It is a lot of putting out fires, but like you said, “Don’t waste a crisis.” I love that.
That’s overused, but it’s true. I want to talk a little bit. You had some good examples and good exercises in the book for looking at your work, for individuals to look at what they are doing. How are they spending time? I’m wondering if we could talk a little bit about how you had the pie chart about current and preferred times and then also charting work categories. Can you share about each of those examples?
There’s such a great opportunity, especially since more technology is entering our flow of work. A great opportunity to do our own segmentation of how we’re spending our time. What’s the highest and best use of it? When do I feel creatively energized? That’s going to be different for each person, but really getting curious about how do I spend my day. Is that the right application of my talents and my abilities?
If there’s any chance to reshape it, you need to look at what work needs to get done and what resources you have at your disposal. There’s a lot of opportunity when we think more strategically about doing the best work that suits us and our talents. I love exercises like this. I do my own probably once a quarter, just to make sure that I’m not over-indexing in areas that is kind of an easy fallback, but maybe not the best use of my time.
You do it even though you’re self-employed.
Absolutely.
You’re in charge. No one’s telling you, right?
Again, we slip into old habits and we slip into those comfort zones. I’m one of those people that I got to get uncomfortable because I know that’s the only way that I’m going to grow. If we can do that in a way that challenges us and helps us grow in the right ways, I think it’s a healthy exercise to do.
Just on the pie chart, walk me through that example. What is the pie chart exercise?
I typically just draw a big circle in the middle of the page and I portion out, what are all of the sections of work or even free time, and how am I applying that time? Is that the right percentage of the time? I break it down in my mind what I’m currently doing. I’ll do another pie chart and another circle, where I think this is how optimally I’d really like to be spending my time. Maybe it’s more time with my family, or I need more exercise, or more time in that white space zone of writing, imagining, and just creating. Really trying to shift from the current state to the future state, and then what small tweaks or changes would I need to make to create that future state as a reality?
The future state being, I think you call it a preferred state in the future. It’s like, what are you doing now versus what would you like to be doing?
Exactly, and maybe it’s less time crafting emails, and maybe you can bring in AI for that. Who knows? There’s a lot of, I think, opportunity now to disrupt how we’re doing our work. Baby steps forward.
I don’t know anybody who’s like, “I really want to spend more time on that email.” Get a lot of joy out of that.
You never know.
That’s true. You never know. What about work categories? I’ve never heard that expressed that way. What’s a work category?
Really thinking about, I’ve got a chunk of work that’s more administrative in nature, or I’ve got a chunk of work that is deep work. I’m in the zone. I’m in my flow state. That would be my deep work. Really thinking through what those different categories of work are? If I prefer to be in that deep workspace, that category of work, how can I optimize my day to protect that time? I think a lot of times we feel like our calendars are a free-for-all and anyone can claim the time but how can we protect it?
How can we really be conditioned to say, “No, this is 8 to 10. This is my deep work time because that’s when I work best.” I also think there’s something to knowing when we have our peak levels of energy when we feel more focused and optimizing for that time. For me, I know in the afternoon, I hit a lull. I’m done by 4:00. I might do more of my administrative tasks at the end of the day, because it doesn’t take as much brain power or creativity. Optimizing for the time of day also really helps.
No, that’s a great idea. I would just observe that one of the takeaways is just for people to be aware and paying attention about what do they like and when they should be doing the things that they like basically. On the calendar example, I had a big project recently and I had blocked out a couple of hours throughout the week on my calendar, which was going to be this deep workspace. No joke, people physically lined up during that time and it was like a revolving door. I don’t know if you have any advice for me on starting that deep work at 5:00 in the morning so no one’s up.
I think it can become a cultural norm. If everyone on the team knows, “If I have deep work on my calendar, that is no joke. I don’t want to be disturbed.” That becomes the norm of the group. Easier said than done, perhaps.
When the CEO’s there, “Sorry, sir, I’m in deep work time.”
If the CEO adopts that behavior, I think it is possible. Again, easier said than done.
I appreciate the coaching around making an intentional decision on running the calendar and not letting it get overrun with other people’s priorities. I had a conversation again with Sterling Miller recently and we talked a lot about that. His book on in-house productivity has a lot of tips for that. The other thing I wanted to talk about, which you referenced throughout the book is how connection is important to creativity. I think you and I share a core value of connection. Can you talk about how and why are connection important to creativity?
I think creativity starts with connection, whether that’s connecting to yourself, what’s important to you, what inspires you, or connecting to those around you as co-creators. I’ve never seen a creative team not have a sense of connection. A sense of safety, a sense that it’s okay to make a mistake or maybe look silly in front of my colleagues. That safety is so important to generate ideas because we know the ideas aren’t all going to be good. There’s going to be some junk in there, but you got to get it out to get to the good stuff. I really do like starting with that sense of connection, starting with relationships and feeling safe playing together as co-creators as a starting point to creativity.
We talked about creativity killers, but you also write about creativity boosters. Let’s give people some concrete ways that they can not worry about killing it, but how can they boost their creativity?
Creativity Boosters And How To Maintain It
This is, again, a really personal thing. What inspires you? What lights you up? What’s your boost of creative energy for the day? It might be playing with Lego with your kid for a while or just taking a walk around the block and counting how many red flowers you see. I think anything that gets you out of the monotony of the work schedule and breaks that cycle can be really helpful as a disruptor and a brief intervention. That’s really what a creativity booster is all about. It’s just a short interval of time that takes you out of that rut.
Boost your creativity by taking short breaks. Whether it’s a walk or a chat with a friend, anything that disrupts the monotony can be a creativity booster. Share on XIt’s personal. People need to think about what is something that would give them that break.
Absolutely. For some, it’s social. It’s picking up the phone, calling an old friend, and having a quick conversation. For others, it might be more introspective. It’s just journaling for five minutes. Whatever suits you can work.
I feel like to our earlier part of our conversation about space, I liked your idea of getting up and just taking a quick walk. For me, and this is personal, but it’s very hard to feel creative when you’re in your exact same workspace in front of that computer with the email dings popping up.
It might be taking a walk, shifting the energy in some way. I’ve even heard of folks who take their laptop and just sit under their desk. They’re in a different physical space.
George Costanza style.
Absolutely, but it’s a new perspective, and it’s a new way of shifting the energy.
Let’s just talk a little bit. We sprinkled in here about the book. I don’t know if it was a COVID project, but you decided to write a book during COVID and then really ran the marathon over the last few years. Can you talk about what was your inspiration for writing Born to Create?
I do have an unconventional path to business. As a former professional actor, singer, and dancer, when I made the leap into business, my big aha was how creativity was essential to building that company and that culture. We just don’t talk about it in those terms, but all of a sudden, all of these practices that I had been honing for years really did apply. I wanted to get more of those practices and those principles out into the world. The book draws on artists, entrepreneurs, and business leaders, many of whom are lawyers, who use creativity and apply it every day in their work as leaders and professionals. Those are stories that I really wanted to get told.
Did the pandemic have a role in you writing it, or do you think that you would have picked this up anyway?
The pandemic was an interesting time with two little ones running around.
Then you started your business during COVID, too, right?
Yes. I started in February 2020 and then the whole world changed. The business idea was actually to bring people together in a room and co-create in a workshop. There was a lot of that happening, but you have to pivot, and we’re all going to have to reinvent ourselves and our strategies at some point. That was a good test case.
As we’re wrapping up here, talk a little bit about Spring Street and what services you provide. It sounds like the legal community is one of your main markets. Tell us what you do.
It usually falls into one of three categories, sometimes all three. I do a lot of culture assessment and strategy work. Really taking a look at how the team is gelling and where we could improve. I also work on specific learning opportunities, so develop workshops and custom leadership training and facilitate off sites. Then I do executive coaching, sometimes one-on-one and sometimes with an entire team. Usually, a combination of those things helps to move the culture forward in a positive way. That’s the goal.
I’m guessing since you launched it during COVID, it’s both virtual and in-person.
It sure is. Yes. Absolutely.
Great. Anne, where can people find out more about you and more about Spring Street and where can they get the book?
The book is wherever books are sold. Amazon works. Feel free to connect with me on LinkedIn, just Ann Jacoby, and I’m at SpringStreetCo.com. Would love to hear from you.
Great. Thank you so much. I’ve taken a lot of notes about things that I’m going to take back to my team about getting us out of our creativity rut. I try to incorporate some creativity into this show and ask all guests a creative question that gives the lawyers a lot of stress as you can imagine, but what is your pump-up song?
No question. I’ve got to go with Titanium featuring Sia. She has quite the voice.
I love that. Anne Jacoby, thank you for being in the show.
Thank you, Stacy. It’s great to be here.
—
Anne Jacoby’s baseball stats.
My name is Anne Jacoby and I’m the CEO of the culture consultancy Spring Street and the author of Born to Create. A fun fact about me. When I was a teenager, I was in a Disneyland commercial and got to ride Big Thunder Mountain Railroad about 20 times and say into the camera, “I got into Disneyland for only $22.” If that doesn’t date me, I don’t know what will.
Important Links
About Anne Jacoby
Anne Jacoby is founder of the culture consultancy Spring Street, dedicated to cultivating creativity at work. Through culture assessments, workplace strategy, leadership programs, and coaching, Anne partners with leaders who crave more connection, innovation, and inclusion across their teams. By combining her early career experience as a performer, an MBA from NYU’s Stern School of Business, and 20+ years as a business leader, Anne sparks creativity in teams to find more joy and drive business results.
Prior to running her own firm, she was the 7th employee of the legal disruptor Axiom, where she served as General Manager of the Southern California practice for 5 years. Her bestselling book, Born to Create, features artists, business leaders, and entrepreneurs, and was a #1 new release on Amazon. She is a repeat guest lecturer at leading universities around the globe, including USC Marshall School of Business, Pepperdine, and HEC Paris. More at springstreetco.com.
