You don’t have to project perfection. I don’t think I ever expected myself to actually be perfect, but I wanted people to think I was, or at the very least, that I wasn’t making mistakes and was above reproach. When my boss gave me what I perceived to be negative feedback, even if constructive, I panicked and bristled. I was afraid of being seen as making mistakes because I didn’t think young women leaders on their first tour of managerial duty would get much slack.
As a part of our series about strong women leaders, I had the pleasure of interviewing Cara Bradshaw.
Cara Bradshaw is a communications and fundraising professional who has worked on teams at international humanitarian organizations, in higher education, and in the media to promote social justice and community engagement. Cara currently serves as Chief Impact Officer at Family Promise, a national non-profit that provides community-based solutions for families at risk of homelessness. With a dedicated team, Cara works to elevate the Family Promise brand, engage stakeholders through powerful storytelling, and deliver long-lasting social change through meaningful philanthropy.
Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
Growing up, I was always drawn to humanitarian and social justice issues. My father was a minister and my family spent weekends on Habitat for Humanity builds and chopping firewood at the local women’s shelter. When I was 15, my parents divorced, my father left the church, and my mother worked two jobs as a school bus driver and teacher’s aide. We experienced financial and housing instability, and it was a time full of anxiety and uncertainty. But I ultimately had a safety net of grandparents that prevented us from falling too far into the cracks. I was able to attend college and graduate school (my parents and I borrowed and paid our way as we could) and made connections to the kinds of organizations I wanted to work for.
So many people do not have any kind of familial or social safety net. Their stories and life experiences are important to me because I see how I could have ended up on another path. I have always believed personal storytelling is one of the most powerful tools to raise awareness and funds for issues I care about, and I’m fortunate to be able to do that through my work.
Can you share the most interesting story that happened to you since you began leading your company?
I took a role directing fundraising as the organization’s founder was retiring and a long-time organizational leader was stepping in as CEO. I would be his “number two.” Around the same time, I became a step-parent to my partner’s two boys. It was a lot of newfound responsibility, all at once.
It seemed in most of my professional meetings in those early days that it helped my credibility as a female leader to say that I was married and had a family. The people I met with usually asked the ages of my step-sons, assuming they were babies because I was in my mid-thirties. When I said they were 13 and 16, they rarely disguised their shock, or sometimes disgust. I cannot tell you how many awkward or inappropriate comments I received about my newfound step-motherhood. People have said: “You’re practically the same age!” even though there’s a two-decade difference and I technically could have been their mother. I’ve been consistently asked why I don’t want “my own” kids. One prominent NYC fundraiser told me in an introductory meeting that I “was the enemy.” It’s been something I’ve had to navigate carefully when people ask “do you have kids?” I have also noticed this is not something as quickly asked of male leaders, and is certainly judged differently.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
I came into my new position from a college setting, with a larger fundraising staff, bigger budget, and more advanced technology. I had become used to things being done a certain way, and felt that I was going “backward” since I had to spend my time on technological challenges, database transitions, and hiring and firing. I was impatient and nervous that I wouldn’t be able to raise enough in the first year to prove myself because I had so many infrastructure projects on my plate. I said too much too early, and should not have made a comparison between a University setting and a lean non-profit. It was, in fact, what drew me to the job — there was so little waste in the organization that I knew I’d be stewarding people’s donations well. I remember one particular moment, fumbling with an old laptop, that I threw my hands up and said something to the effect of “It’s 2015 and I have to use GoToMyPC like an employee of the Stone Age?!” That wasn’t super well-received.
The lesson I learned was to go into any new role as an observer for the first six months. I’d recommend that other new leaders take inventory of what might need to be changed, updated, or upgraded. Make notes, write down ideas, talk to friends and family about what your vision might be. But for the sake of the people who have been working so hard there and who are accustomed to the way things have been, be patient and not critical.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
As cliche as it might be, my partner has been my primary champion in my leadership journey. I think it’s still rare, even in 2020, to have a male spouse or partner put their ambitions or plans on hold to let you explore yours, or who will cook and take care of the many domestic duties that go with modern partnership. I have been fortunate enough to have a listening ear, a co-strategist, and a true egalitarian in the home that allows me to focus on my work and help me problem-solve challenges. I don’t do well with a total separation between home and work. I believe the two are so fused to our identities and it’s energizing for me to have my partner attuned to my professional goals and my day-to-day work life.
Earlier this year, while mountain biking, my partner and I were talking about our professional trajectories. I shared that I was still feeling torn about whether I wanted to try to keep “climbing the ladder.’ I could think about other directions to take instead — my own small business, or something more off the career grid. He looked at me, totally certain in what he was about to say: “I think you will regret it later if you don’t go for it, if you don’t take all of the lessons learned and all of the curiosities and ideas you have about organizational leadership and at least try to make it happen. You’ll have plenty of time to do the other stuff, too. But for now- I think you should go for it. I think you’d be phenomenal. And I’ll be right behind you every step of the way.” How incredible is that?!
In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?
Moving my body and being in nature are hugely helpful for me. The day before a high stakes meeting or presentation I make sure I carve out time to be outside and release. Mountain biking is a perfect mix of movement and focus. If I’m thinking about other things, if I’m distracted, I don’t make it over that rock or log and fall flat on my face. Mountain biking requires me to be present, to be intentional and mindful, and it also releases a great deal of pent-up energy.
I think perhaps one of my most nerve-wracking professional moments was introducing Krista Tippett at a Family Promise national conference in Washington, D.C. My boss knew I was an On Being listener and an admirer of Krista’s and asked me to make the introduction. I worked diligently on it, wanting it to hit all the right notes and also come off as genuine and conversational, not scripted. My entire staff, my boss, the founder of the organization, and my partner — who is an incredible public speaker — were there. I would be sharing a meal with Krista before introducing her. No pressure! I did not have my mountain bike, nor was there time for a ride. So I woke up very early that morning, watched the sun rise, and jogged through Arlington National Cemetery. I still had the jitters — no doubt. But giving myself a few moments to release, to breathe deeply, and to center myself for the day helped tremendously.
As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?
We have been consciously working on diversity and inclusion at our organization and still have much work to do. Having a diverse executive team ensures there are different perspectives, ideas, and life experiences present in the decision-making process. It’s easy to hire people who look like you and whose educational and personal backgrounds are similar to yours. That’s comfortable. And many businesses and organizations get stuck in that pattern. I think it’s important to have external auditors or consultants specializing in DEI look at the organizational culture and highlight implicit biases and impediments in hiring, retaining, and promoting a diverse workforce.
As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.
Diversify philanthropy: For too long white, affluent, mostly men have been the driving force of major philanthropy. We need more grant-making agencies led by women, people of color, and LGBTQ leaders so that they are making decisions about where money is directed and how programs either empower or further marginalize communities. We need more people of color leading all types of nonprofits. The Ford Foundation has clearly made a major shift toward diversity & inclusion in its staffing and funding model, and I am impressed that they recognize nonprofits need money to do what they do, not constantly create new programs to chase foundation dollars at the whim of a few old school decision-makers.
Democratize philanthropy: Social impact campaigns such as Together Rising and Black Lives Matter have made a 5 dollars donor just as important as a 5,000 dollars donor by raising millions of dollars through crowd-sourced campaigns where the average donation is 25 dollars -30 dollars. Some campaigns even put a cap on what you can give, so that it’s not a show of might.
At Family Promise, we’ve been working to engage the next generation of givers and do-ers and inspire them to support the organization at whatever level they can through peer-to-peer campaigns. Families in our shelter program and who have graduated also give. We ran a COVID-19 emergency relief campaign in late March, and a single mom staying in a motel room with her four kids, working to hold down a new job and helping her kids with schoolwork, made a donation. Her gift is priceless, and per capita, it’s actually more impressive than some of the larger gift amounts we received! That’s the future of philanthropy to me.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?
There is so much organizational strategy that goes with the job. Along with the people and project management, there’s a constant tension (even if positive- I personally enjoy it), on the overall strategic direction of the organization. When a team member asks me a question about how to code a donation in our accounting software, for example, and my head is somewhere else, there could be big implications for my answer. We have to be present, listen, and respond carefully.
What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?
That we know more than the team members working with us. I firmly believe that the people on my team know as much about fundraising and communications as I do- and sometimes more. I might have more insight into the workings of our board and conversations with our CEO, but in terms of subject matter expertise, I think people too often look to the leader to solve something they intrinsically know or could figure out.
That we’re “authority figures” instead of co-collaborators. There is of course a place for hierarchy and structure. However, my most effective managers/bosses have treated me as a peer, and it inspired me to do my best work. I don’t see anyone on my team as working for me. I see them as working with me to further the organization’s goals.
In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?
We do a lot of the “women’s work” and emotional labor in an organization. We remember birthdays, throw baby showers, and organize staff outings. It’s easy for male leaders to delegate this to female staff. I’ve participated in organizing these events at every job I’ve held. Staff also tend to come to women to air their grievances or talk about personal matters. I’ve also noticed that women are almost always asked to be secretaries in meetings, taking notes for the group, and men are rarely asked to perform this function. I’ve also thought that a male leader in my position would never be asked to take notes or minutes in a meeting.
From my experience, men I’ve worked with over the years have had no reservations in demanding public praise for their accomplishments, and want to make sure the whole team knows what they’ve done. There is also no hesitation to turn that into a request for a raise or promotion. Women, on the other hand, are often sheepish about pointing out their accomplishments and feel guilty about asking for more money, especially when working in a non-profit setting. They often apologize when asking for it. I’ve had to justify myself and my value at every single job I’ve held, even when the responsibilities continue to stack up and I exceed my goals. Over the years, in organizations of various sizes and when interviewing for new positions, I’ve had to fight for increased pay. Not once has it been offered (other than a cost of living raise), in recognition of my performance. I’ve known male counterparts who have been preemptively offered raises as a way to retain them.
What is the most striking difference between your actual job and how you thought the job would be?
It is so much more internally-focused than I imagined. A huge part of a fundraising/PR job is to be external, to network, and to pitch the organization to potential donors and partners. As a new manager in this position, I had so much internal work to do and trust to build. Still, once we got to that place I could be more external, I still spend a fair amount of time on internal management, conversation, and planning. This is not a complaint- I enjoy this work. But to “get out there” requires blocking off time on my calendar to do the work of making connections.
Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?
This may sound so simple but I think it’s the most important: you have to like people and want to listen to them. I mean actually like people and be interested in them as humans and curious about what makes them tick. As a leader, if you like the people you work with, even if you have differences and disagreements, you can figure out how to help them on their professional journeys and set them up for success in your organization and beyond.
In one of my previous jobs, the leader of the organization clearly did not like people. They mistrusted people, thought everyone else was stupid, and it read loud and clear in every interaction. They were not interested in what people had to say, or what their worries or big ideas were. They referred to anyone with a challenge as a “squeaky wheel.” I find this to be incredibly ineffective management (I can’t even call it leadership).
People who are in leadership positions because they crave power and need their ego to constantly be stroked may be “successful” on the outside, but if the people who work for and with them don’t enjoy showing up to work each day (physically or virtually), I don’t believe they’ve succeeded. We spend too many hours a day at this for it to be a total slog. We deserve to enjoy our work. I also believe in humanity over efficiency. If we treat people well, they will be more efficient and the bottom line will improve. If we micromanage, demean, or put them in competition with their peers, the work suffers.
Leaders listen, reflect, and inspire action that serves the employee and the organization.
What advice would you give to other women leaders to help their team to thrive?
Do your best to figure out what each team member needs. Some may need more feedback on their work, others need recognition and praise, and yet others like to be more independent and check in less frequently. I try to find what works for each person and make sure they know that I’m accessible at any time (it’s never been a problem to offer that). I try to be as responsive as possible and not let anyone’s work be delayed by my decision-making.
How have you used your success to make the world a better place?
I sure hope that I have. I am very committed to the work we do at Family Promise and I consider housing as a human right for every family. The most important thing I can do is to take a step back from the strategy from time-to-time and get to know someone who is experiencing housing instability. I bring my own personal experience as I listen to theirs. That person-to-person connection helps me bring compassion, empathy, and non-judgment to my work. It also helps me communicate clearly with our stakeholders who may not understand all of the root causes and systemic injustices that lead to a family’s homelessness.
What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)
- You don’t have to project perfection. I don’t think I ever expected myself to actually be perfect, but I wanted people to think I was, or at the very least, that I wasn’t making mistakes and was above reproach. When my boss gave me what I perceived to be negative feedback, even if constructive, I panicked and bristled. I was afraid of being seen as making mistakes because I didn’t think young women leaders on their first tour of managerial duty would get much slack.
- You will not impress everyone. When I started in my position, there were some legacy employees who were suspicious of me and I think now I may have put too much energy into trying to win them over. If you get in the trenches, do the work, and are fair to people, that should be enough. If they still are resentful of you or don’t back you up, it might be time for a hard conversation.
- You are going to have to do hard things. I had never fired anyone when I got to this job. And I had certainly never fired anyone I’d hired. I had to do both within the first year of this role and I lost sleep, confidence, and almost decided organizational leadership was not for me. I’m glad I kept going.
- Draw emotional boundaries. I don’t mean not talking about your personal life at work (I think there’s value to vulnerability in the workplace), but draw boundaries for yourself about what you let upset you, or what you react to. I’ve had to learn to be more patient and less reactionary and it has served me much better.
- You can “be the change.” If you bring positive energy and a can-do attitude to an organization, you can be an example of what you want the work culture to be. If you don’t appreciate people gossiping about other colleagues in your office, don’t let it happen, and certainly don’t do it. If you want people to have a good work-life balance, model that and be sure to leave the office at a reasonable hour, disconnect from email, and use your vacation time.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
We have a serious affordable housing crisis in this country and we’re saddling the next generation with tremendous student loan debt. Since COVID-19 is shutting down on-campus living and likely will be doing so for the foreseeable future, I’d see colleges and universities using their empty dorms to shelter people on an emergency or transitional basis. Some of our Affiliates have worked with schools to use their dorm space this way in the past, and I think we could scale it through our footprint. Small liberal arts colleges will be hardest hit as international students will not attend and parents will reconsider paying hefty tuition bills for their students to have the “college experience” at home. I’m not sure how you justify upwards of 60K dollars in tuition to live with your parents and take courses online.
It would be an admissions incentive and possibly a revenue-maker if certain for-profit entities sponsored the idea (startup biotech firms could use vacant campus laboratories and offices, for example, and that rent could subsidize the affordable housing component). Nonprofits working with the populations being housed on campus could provide experiential learning opportunities, internship experience, and credit for students. Undergraduate students could be virtual mentors/companions to high school students; they could help with storytelling projects, marketing, data projects… the possibilities are endless. And graduate students in programs like social work could get hands-on case management experience. With unemployment soaring, parents are going to be most concerned with their kids obtaining real-world skills and workplace connections during their college years.
My dream would be to see fewer children experience homelessness, colleges and universities use their space and their community resources to serve housing-insecure populations, and young people not graduate with the burden of student loan debt, which greatly affects their economic mobility.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
“Tell me, what is it you plan to do with your one wild and precious life?” -Mary Oliver
I don’t believe these words intended to pressure people into pursuing high-powered public lives (unless that’s what truly makes them tick). Mary Oliver spent most of her life sitting in nature, watching geese, observing flowers grow, and writing in solitude. To me, this quote is about giving our life experience all we have, whatever that means for each of us.
We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.
I’m sure most everyone would say the Obamas. I greatly admire them individually and as a couple.
I’d also love to share a meal with Abby Wambach and Glennon Doyle. Their commitment to women’s equality, LGBTQ issues, and racial inclusion, and to love, is inspiring. Coming from a blended family and creating one as an adult, I really appreciate the tenderness and openness they bring to it. I also respect people who tell the honest truth about their lives, even if it sets them up for criticism. Which brings me to another favorite quote/question by Muriel Rukeyser: “What would happen if one women told the truth about her life? The whole world would split open.”
Thank you for these fantastic insights. We greatly appreciate the time you spent on this.