Annie:
Welcome to the whole Assistant podcast. I'm your host, Annie Croner. I'm a former assistant who's passionate about our profession, and I'm also a certified coach who's invested in your success. You've come to the right place if you want to know what it looks like to stand in your power and achieve success as an assistant through overwhelm and burnout. Now on to today's episode. Hello, everyone. Friends. So I have a special treat for you today.
Annie:
Joining me is Jennifer Connelly. Jennifer is one of my good girlfriends. We've worked together in both of our last roles, and we office together, and we just developed a friendship, as you do when you work with somebody closely. Even though we weren't working in the same company, like in close proximity to one another. And I think we also have similar values. So that's kind of another reason that we came together. And so, Jen, I would love it if you'd introduce yourself, let everyone know a bit more about you. Actually, before I have you do that, the topic for today is creating safety and trust in the workplace.
Annie:
And I feel like as executive assistants, we have a lot more influence on safety and trust than we give ourselves credit for. And so I just kind of wanted to flush that out with Jen. And Jen is well qualified to speak on trust and safety in the workplace because she not only was an executive assistant, is a chief of staff right now, but she also has HR experience. So, Jen, will you please introduce yourself and let everyone know a bit about you?
Jennifer Connelly:
Yeah. Well, thank you so much for having me, Annie. It's great to be here with you all and everyone listening to this at some point in the future. My background is interesting. I took a different path than the traditional go to college, get a job, all of those things. I, at 18 years old, really thought I was going to be the next Donna Karen. I wanted to be a fashion designer. And so back at that time, I actually sent physical letters in the mail all over the United States seeking an internship.
Jennifer Connelly:
And I got an internship in Nashville, Tennessee, of all places, at two different design houses. And I worked there, gosh, for almost five years. And I started as an intern, then became a design assistant and worked my way through to brand director, really doing every job well, except for designing. So what I learned from that was that I had really more of an acumen for the operational aspects of things. And in 2008, 2009, the downturn happened, and nobody was buying $80 t shirts anymore. And I found my way to a different path. And that's when I started to really think about what does it look like for me in my future? How do I want to spend my time? And for me, I think being such an integrator, I've always looked for visionary leaders, and I have found myself through a series of paths back in Colorado from the south. And I've worked for just incredible leaders here in Denver in the private equity, real estate and family office circles.
Jennifer Connelly:
So currently a chief of staff at Alder Companies, which is a single family office. And my role really now is more about marrying the strategic objectives to tactical execution and really making sure that everyone understands what their contributions do to get us to our overall outcomes together. And that could mean so many different things in the day. And that's probably a conversation for another time, but that's just a little bit about me. Education background I do have a degree from the University of Denver in organizational leadership. I'm kind of obsessed with educating myself. So I went and got a project management certificate from Cornell. I got the Sherm SP certification.
Jennifer Connelly:
I have a couple of behavioral certifications. Most recently, though, I went and had the opportunity to go to Harvard and take a wealth management course, which was really helpful for me. Kind of balancing out that other side. And probably interesting to your audience is I also took this AI prompting for operations boot camp where I really learned how to start integrating AI into all the micro tasks that I do all day long and making myself more productive. So I'm a lifelong learner. I love the human capital aspect of things, and I'm always trying to learn, seek and develop myself individually as well as the teams and organizations that I work within.
Annie:
So awesome. So I'm going to pick your brain on the AI for operations thing. I think that would be super interesting to have you come back and talk with everyone about that for another day. But today we're talking about there again, how do we create safety on our teams and how can we influence change in our cultures? Which is like the cultural change piece is a piece that I really have been thinking about a lot lately, especially for executive assistance and support staff. I think that often we don't think that we can influence the culture, and so we end up feeding into it in ways that are unintentional. So in an effort to create more intention and really make sure that we are paying attention to how we're showing up, especially when it comes to creating safety, how do you think that executive assistants can influence change and create more safety for their teams? And then how do you think that we can influence the environment to help people to feel safe and expressing their opinions and ideas. I would just love it if you could share your thoughts around that. I know it's a heavy topic, but please.
Jennifer Connelly:
Yeah, that was quite a question. Thank you, Annie. I think I'll start a little bit higher level and talk a little bit more about culture, because I think you're absolutely right. And I think that sometimes people think of culture as perks. Do we have ping pong table? Do we have beer in the office? But actually, culture is your behaviors that are expressed in your company. And the job of culture isn't to make you feel good. It's really to drive the strategy. And so your behaviors are what drives the outcomes of the business.
Jennifer Connelly:
And to your point, I think that there is a disciplined approach to culture, or there is a default approach, which is what it currently is, without really being intentional around it. And I think in our best day, we're probably 51% disciplined and 49% default. But having awareness is the first start. So what is your experience of your culture, and how do you think that you're impacting it? And sometimes you may not realize how these tiny things do impact culture. So when we think about it in terms of psychological safety, an environment where you feel like you have psychological safety feels very collaborative. There's a lot of creativity. There's a lot of ideations. There's also an overall feeling of failure is a good thing, and you want to fail fast, and you want to get back on that horse and try again.
Jennifer Connelly:
Conversely, when you're in an environment that doesn't have a lot of psychological safeties, it's sometimes even hard to speak up and even just state facts versus having these creative ideas. And if you think about it from a personal, individual perspective, what I've really kind of experienced and witnessed, even this week, is that really, it starts with yourself, and you really have to go internal and say, what psychological safety do I have within my own self? How am I showing up every day? And do I feel confident to speak my truth and say my opinion, regardless of if I'm at home, work, or in the community? It really starts with you. And I think that you'd find if you look back at your old past selves and I'm thinking of my own self, included is the times that I've had the least psychological safety was really more self imposed than environmentally imposed, and that I can have a confidence in my thoughts or confidence in my ability to express myself. And I could blame that on any external thing in the world, but really, it did start with me. And having that confidence in myself that no matter what, even if I'm looked at crazy or let go for my opinion, that having that first foundational piece of confidence is really critical. No matter the environment you could be in, if you don't have that, you certainly aren't going to feel that safety to have that creativity and innovation. I also think it does depend on your own temperament. So when you're thinking about that, I know instantly you think of like, oh, if I'm very introverted and I'm in this large meeting, even though I'm confident in myself, maybe that's not the environment where I feel comfortable.
Jennifer Connelly:
And so what I would say to that is, yes, but then it's on your responsibility to circle back after the meeting and have a second meeting with a smaller group and share your opinion or send an email around with something along the lines of, hey, during the meeting, I didn't get a chance to say this, but I wanted to follow up and express myself. So I think it's really something that foundationally starts with you. Your environment definitely has an impact on, I think, your outward expression of it, but you really have to get good within your own inner world with your ability to feel confident in yourself and your ideas.
Annie:
Yeah, I like that. And I also feel like for a lot of us, we don't speak up because we fear failure and because we fear looking stupid and so getting over those fears and then having your own back and realizing that if you do end up looking stupid in someone's eyes, that that's really not about you, it's more about them. Now they're interpreting you right and then trusting yourself to actually put it out there. And even if it doesn't come out 100% as you planned or in the perfect. I'm using air quotes for those listening on the podcast in the perfect way that it's still valuable and it still can help affect company culture. I feel like we're the drops in the bucket when it comes to and actually using your voice can be a drop in the bucket towards cultural change as well and towards creating that safety for others to speak up and towards forging the way for others to be able to utilize their voice and setting the example and setting the standard. So, Jen, in your opinion, just curious, how would you handle a situation where trust within the team has been compromised?
Jennifer Connelly:
I think it starts with transparency. When you have a break in trust, it usually comes from somebody withholding information or blatantly just disregarding what the instructions are. And I think that you have to come and first of all, lay that out in the open and go over. What is it that broke the trust? What are you actually talking about? So transparency is key. So I think you just have to talk about it and I think that can be very uncomfortable at times. But if you don't do that, you get further and further and further and it's harder and harder to bridge that trust gap, and it's also much harder to get results out of your team. Once that trust is broken, it can be unsustainable, I think, after a while.
Annie:
Yeah. Do you have any tips for executive assistants if they weren't the ones breaking the trust and how they can play a role in mending those dynamics? Especially because for most executive assistants, they are the sounding boards for their teams. So they're the person that people are going to come and complain to. They're the person that people are going to come and bring their things to. It's not like the higher ups, but it's like the executive assistant. So do you have any tips for someone in that seat?
Jennifer Connelly:
Yeah, I think you just have to hold the standard, and it is an interesting role where you have to have trust up the chain and down the chain and you really are seen as this confidant for every level of a company. So I think you need to hold the same standard. And if there's something for you that doesn't sit right and you're feeling that trust has been broken, I think your first step is always to give the person the opportunity to address it themselves. But at some level, depending on the situation and who it is and who's involved, at some point you're also going to have to be accountable for that transparency. And if someone's not holding themselves accountable and coming and being open about whatever trust was broken and you know about it and you know how it will impact the culture or the business or your executive, there is a little responsibility on you to figure out how to get that information shared. But it's tricky not to break trust and confidences that are a long time built and quickly tattered. So it's a tricky one. I think that you, but you have to really hold a standard within yourself and say, I want to hold your confidence, but if it crosses this barrier or line, I have my own responsibility to share that information.
Jennifer Connelly:
But I think the best thing you can always do is set the example. So when you yourself, because we're all human, have made a mistake letting people know, holding yourself accountable and showing that standard I think is the best way to approach it. But you are in a tricky situation where you're having to really air traffic control the way that you want those relationships to play out over time, and you have to really understand what is the priority and where your boundaries lie. That's really key.
Annie:
Yeah. And a lot of us haven't really considered our boundaries because most of us kind of override them on a daily basis.
Jennifer Connelly:
Yeah. Boundaries are a whole struggle, and I think that's also part of the safety that's created. If you're constantly just having to reinforce your boundaries day after day after day, there's not really a lot of safety that's built for you because you're just waiting for somebody to come. And whatever the case may be, call you after hours, email you at 04:00 a.m. Whatever that boundary for you is that if you're constantly, always having to reinforce and hold that line, there's not really a lot of safety built around that for you because you don't trust that person not to just constantly try to run over you.
Annie:
Yeah, for sure. And I also think that kind of comes back to the whole want match thing that I talk about a lot on this podcast is like, clearly there's some misalignment in your role and what you actually want out of your role and the demands of the role, because for another person, being called at 04:00 a.m. Is no big deal. I'm always surprised by that. But it's true. People will work around the clock and have no problem with it. And I think for me, in my past, I can think of a period of time where that was totally me. I had really not a whole lot going on.
Annie:
And then now I'm married, I've got babies. That is just a no for me. Yeah, that's a value shift in myself. Right. So you really actually have to know what that line is for you. And then also, there again, create the safety for yourself. And if your role isn't a watt match, maybe just know that and look elsewhere for those better values, alignment with your position. So how do you balance the need for accountability with creating safe space for your team members to take risks and make mistakes? Because you mentioned just a minute ago, you want to fail and you want to fail fast and you want to fail forward, and how do you do that and still hold your team accountable? What is a line there?
Jennifer Connelly:
Yeah. So I think it's really simple that you have an outcome that you've agreed upon. And I think the way that you start with building that foundation of safety is you know what the outcome is, but you know it's not going to be a straight line to get there and having that expectation up front, I think even just saying the words, this is going to be an iterative process, setting that expectation. I think using phrases like perfection is the enemy of good. And there's a certain way of using language, I think, that sets the table for how that process is going to unfold over time. And if you have that at the beginning, then you are really easily falling into this pattern of, what about this? Let's try it this way. Oh, it's working. Okay, let's see if we can make this better.
Jennifer Connelly:
Let's tweak that. And the other part about that that is on the flip side of that is you also have to have an end date in mind because you can iterate forever and you can also lose the locker room that way as well. So having an iterative process, but also having the confidence and I guess safety in your own self to say, okay, we're going to have to implement this, and then we can iterate in a quarter or a month or whatever the case may be. So I think having clear expectations, having an expectation that it will be iterative and then also knowing that at some point it's going to have to be good enough and you can come back and iterate again is also pretty critical. But I think that it just comes down to good, clear communication, the example setting, and then really, really just letting people know that this is a time to be creative and iterative. And I think that having that experience and getting those reps when that's an expected experience can really set a shared language and shared understanding for when times. And it's a little more gray. And maybe you need to get it done quickly and get it done now.
Jennifer Connelly:
There's not that much time to be iterative. People are probably not that open to ideas when things need to be happening quickly. But I think that if you already have that process built and that language, you could say, I hear what you said, let me try one more iteration and then we'll execute and come back to it and tweak a little bit. So I really think it just comes down to really knowing what it is, how to have a shared language, and also how to set expectations for what the actual timeline and urgency of things are.
Annie:
Yeah, and I think so many of us get entrenched in our perfectionism or in a way that we've done it in the past, that having those conversations can be difficult for us. Right. And trusting that process of iteration and collaboration. I know for me in the past, it's not that I don't want to be collaborative. It's just that I want to own my piece, and I don't want to spend a lot of time talking about it. I don't want to be in meetings every day, all day talking about it. I'd rather go and work on it and bring it back to the group and, like, my piece of the puzzle. And so I think it's also kind of knowing how you work best and then knowing how others on your team work and then meeting in the middle for that collaborative process to be successful and then also letting go of your perfectionism.
Annie:
Because a lot of us want everything to be perfect from the beginning. If it's not perfect from the beginning, then we beat ourselves up, or then we feel like it's not worthy or we're not worthy, and we can attach so much of our worthiness to our work. Parsing those two things out and separating those things so that you can have more collaboration and you can have iteration is really important as well.
Jennifer Connelly:
I totally agree.
Annie:
Yeah. Okay. Well, Jen, this has been super helpful for my audience. Can you guys see why we're, like, some of the language we use? You've heard me say similar things on the podcast before. Like, this is why Jen and I are.
Jennifer Connelly:
Interesting. To that point. Annie, I think for you, what I learned the most from you is that it does start with yourself. It really starts with that inner dialogue. Everything, whether it's psychological safety, your work ethic, your want match, all of those things really start with knowing yourself and giving yourself that honor of boundaries. And I can't tell you how much you've helped me with that personally. And I'm sure your audience also feels the same way. So thank you, Annie, for being who you are and such a strong leader in this space.
Annie:
Thank you so much, Jen. I really, really appreciate that. So, yeah, where can people find you if they want to connect with you?
Jennifer Connelly:
I'm on LinkedIn. Jennifer Connelly. You'll notice I'm not the famous actress, so I'm the other one in Denver. Feel free to send me a message anytime.
Annie:
Okay. Thank you so much for joining us, Jen. Bye bye for now, everyone. I help assistants apply the concepts I share on this podcast. If you're ready to take your growth deeper and you're curious whether working with me in a coaching capacity is right for you, please email me at Annie at whole assistant.com to schedule your complimentary discovery call.
