Tiffany Dufu is founder and CEO of The Cru. Their algorithm matches circles of women who collaborate to meet their personal and professional goals. She’s also the author of the bestselling book Drop the Ball: Achieving More by Doing Less. According to the foreword contributor Gloria Steinem, Drop the Ball is “important, path-breaking, intimate and brave."

Named to Fast Company’s League of Extraordinary Women, Tiffany has raised nearly $20 million toward the cause of women and girls. She was a launch team member to Lean In and was Chief Leadership Officer to Levo, one of the fastest growing millennial professional networks. Prior to that, Tiffany served as President of The White House Project, as a Major Gifts Officer at Simmons University, and as Associate Director of Development at Seattle Girls’ School.

Tiffany is a member of Women’s Forum New York, Delta Sigma Theta, Sorority, Inc. and is a Lifetime Girl Scout. She serves on the board of Girls Who Code and Simmons University and lives in New York City with her husband and two children.

Tiffany will be a Keynote Speaker at SFNet’s virtual Women in Secured Finance conference July 29-30. For more information or to register, please click here.

What are some of the steps that women can take to release the unrealistic expectations of having “to do it all” or getting it all done?

Tiffany Dufu: I think the first strategy to releasing unrealistic expectations is to first get your expectations down.  Part of the challenge is we often have these expectations in our head and they’re overwhelming, but sometimes it’s so overwhelming that we can’t really articulate them.

So, the first thing that I recommend for women who truly are overwhelmed is to just get it out of your head.  I think it’s great to just do one exercise where you literally create a laundry list of all of the things that have got you up at night or all of the things that are on your plate, all of the to do’s, just basically a bit of a brain dump.  Because often, certainly for me sometimes, until I do that, it’s hard to move on to something else.

What are some strategies that you recommend for women to really identify what truly matters to them, and what they should focus on?

Dufu: I think the second piece is really the beginning of a psychological journey, to try to separate out what it is that we truly expect of ourselves versus what we’ve been socialized to expect of ourselves. This is really hard because sometimes we conflate the two, or certainly for an ambitious woman who feels that she’s in the driver’s seat of her own life, it’s hard to come to a realization that you are actually living someone else’s expectations; they’re not your own expectations. 

But one of the exercises I encourage women to do, and I’ll share this because you can’t hear it enough, is to really imagine that each of the roles that you play is an actual job. So, write out the roles that you play in your life.  It could be that you are a manager, it could be that you’re a mother, or a wife, or a daughter. It could be that you’re a student. Whatever those roles are, write them all down. Then go ahead and put the word “good” in front of all of them, because we all aspire to be not just be a daughter, but a really good daughter.

Then imagine that there was a job description for each one of these roles and ask yourself two questions.  The first is, ‘What does a good mom do? What does a good manager do? What does a good student do?’ The second question is, ‘How do I know that that’s what a good mom does? How do I know that that’s what a good manager does? How do I know that that’s what a good student does?’

This exercise triggers you to go back into your experiences. There will likely be childhood experiences or cultural experiences, whether it’s advertising or a television show that you watched, that will really help you uncover and unpack why it is that you feel that cooking a gluten-free vegan meal every night for your family is what it means to be a good mom, and, therefore, it’s on your plate and you’re feeling overwhelmed about it.  It could be anything.  But I think the deconstructing of the overwhelm is really important and a very good first step.

The second piece of that, in terms of the next step strategy, is to really think about what you feel should be on the job description. So, rewriting a new job description for yourself and engaging the other people in your life who you care about along with this job description is really important.  Let’s say you have a boss who you’re managing up to. And you want to know how to be a good leader, and create a new job description, and really get aligned with your manager. You could have a conversation that goes something like, ‘Hey, I really feel like we need to hit it out of the ballpark. And I know that that’s our goal to hit our sales strategy, even in the midst of this viral pandemic, I really feel like I’ll be able to do that, but I’d love to get your insight on what you feel are the top three things that I need to be focused on in order to do that.”

You can begin to build priorities for yourself around expectations that are not just rooted in the overwhelmed and what you think should happen, but what people in your life also think should happen. And, by the way, this works well in our personal lives and we rarely do it.  When I speak to mothers, rarely has a mother, even if her kids are older, engaged her kids in a conversation about what they think it means to be a good mom and what their expectations are of her. It’s an important exercise to do within your personal and professional life because what you will often discover is that the people who want you to succeed and be your best have much lower expectations of you than you often have of yourself.

Those are some of the first steps I would take. And then third is a little more existential, but I think it’s important for you to just get clear about what matters most to you in your life, overall. That’s one of the first questions I ask women when I sit down with them. I say ‘What matters most to you?’  Most people rattle off different aspects of their lives where they’ll say, ‘My career matters to me, my family matters to me.’ What I try to coach people toward is what do you hope to achieve in relationship to this thing that matters to you? Your career matters to you, but what are you hoping to achieve in relationship to your career? What are you hoping to achieve in relationship with your kids or your relationship with your partner or spouse? That provokes a different kind of thinking and exploration that allows you to come up with really clear statements so that when you are overwhelmed, you ultimately have to ask yourself the drop the ball question, which is, ‘Is doing X, Y or Z my highest and best use in achieving what matters most?’ You can think about that and reflect on that because you know what matters most, as opposed to just kind of going through the motions each day. So, there is a bit of intentionality that I think is important for us to adopt in our lives for us to really be able to drop the ball.

But step one is getting it out of our heads. If you can’t even write it down, contact somebody who truly cares about you and loves you and send them a text message.  Like if you’re just on the bathroom floor, asking ‘What am I going to do?’, just start with sending a text message that says, ‘I’m on the bathroom floor, I’m very overwhelmed, I need help.’

Have you found women tend to dwell on feeling guilty that they didn’t get everything they needed to get done, which then only distracts or derails them further? If so, how can they break this mindset?

Dufu:  Yes, and I think the first thing is to really understand what guilt is.  Guilt is a feeling that you’ve committed a moral transgression, that you’ve done something terribly wrong. It surfaces when we have this feeling that our values, the things that really matter to us, isn’t in alignment with our behavior, with the way that we’re actually showing up or what we’re actually doing.

For example, you might have a value around having an incredible work ethic, and that might be conventionally important to you. And the behavior that you associate with having an incredible work ethic is being able to work many, many, many hours, but you feel like being able to work a lot of hours is reflective of what it means to have a stellar work ethic. You might be in the midst of COVID-19 right now and be the parent of small children and not be able to devote the hours that you previously thought you could devote and might be feeling this sense of guilt. You may think, I’m letting my team down, I’m not a good worker, I’m not a good manager, I’m not a good team player because I have this value around work ethic, and the behavior I associated with demonstrating that work ethic is working a ton of hours, and I can’t work a ton of hours because I’m homeschooling my kids.

The key to eliminating guilt is recreating that job description so that you are being proactive about the behaviors you’re going to associate with your values at any given time, and it can change.  It may be that, previously, a work ethic was demonstrated through working a bunch of hours. It may be that today having an amazing work ethic is doing what you say you’re going to do. When you overcommit and you’re not able to follow through, then that is a terrible work ethic. So, you’re going to divorce being an amazing worker from working a ton of hours and you’re going to attach it to being really clear about your boundaries and about what you are able to achieve.  When you do that, you can fulfill your responsibility as a worker or as a team player and you can be in alignment with your integrity and your values, and your behavior can match.  Does that make sense?

Yes, it does. So, once women have established their focus and what really matters, what are some steps they can take to help empower other women?

Dufu: Well, the most important thing that they can do to empower other women is to model what it means to be clear about what matters most to them, articulating their boundaries and saying no. I can say no quite gracefully, but definitely saying no.  There is nothing more important to advancing women than women who model the behavior. I can’t tell you the number of times someone has asked me to do something and I respond with a four-step process. First is starting with gratitude and saying, ‘Thank you so much for thinking of me,’ then saying what I’m doing with my time, ‘Right now I am head down raising another round of capital for The Cru.’ Then, telling them that you will not do what it is they’re asking you to do and don’t apologize for it, ‘I’m unable to be there.’ And then, finally, the fourth step is expressing gratitude again, ‘But I so appreciate you thinking of me.’

You would be surprised the number of women for whom I say no to in that way whose response is, ‘We can do that?’  And I say, ‘Yeah, you can totally do that.’ They’re like, ‘How did you do that, can you teach me how to do that?’ I think it’s particularly important with our girls, to set up setting boundaries and being clear. 

You mentioned The Cru, and that was my next topic. The Cru seems to really rely on accountability to achieve goals. While all women have the best intentions for themselves, accountability seems a necessity. Why is this so important?

Dufu:  It’s incredibly important. All of us have set goals that we want to achieve, and the number one reason why we don’t achieve goals that we’ve set isn’t because we don’t know how to achieve them, it isn’t because we don’t have access to the resources, and it isn’t because we don’t care about the goals, it’s simply because there is this thing called life that often gets in the way. 

So, The Cru is there to whisper in your ear, to remind you about the ambitions you have for yourself.  The reason why accountability is so important is because for many women, we spend most of our time holding other people accountable. This is especially true if we’re busy working women. It’s important that we all have a group of people, whether it’s like my Cru, my company, or whether it’s just having a crew, because a lot of us have networks, a group of people that really can provide three things. One is a level of objectivity. The value of our Crus is that they are a curated group of people that care about you, but are not invested in your decision making.

Let’s say you want to get a promotion and that might mean moving to another city. It’s not your partner, who doesn’t want to get another job in another city, it’s not your child, who doesn’t want to go to another school and doesn’t want to move away from their friends.  It’s not a best friend from high school who isn’t quite sure about what that means for the evolution of your friendship, that you’re evolving in a way that they may not be?  It’s not your co-worker, who might be vying for the same promotion that you are. Your Cru is not invested, they don’t have a stake, and so there’s a level of freedom and objectivity that they can provide that I think is really important and I think all of us need that group of people.

The other aspect of The Cru is that it’s a group of people who you would not have otherwise met if you had had left it up to your social group or your workplace. It’s a truly diverse group of people, and I think in this polarized world the more that we can connect with people who have different lenses and perspectives on our challenges, the better all of us will be able to generate more innovative solutions to them.

The third piece is accountability. If you’re going to have drinks with your friend group or you’re having a Zoom with your girlfriends and you’re really excited about it, but you’re not nervous because you committed to doing something and you know they’re going to ask you about it, that’s not a good crew.  There really does need to be this level of, ‘Oh, I said I was going to work on that book proposal or, oh, I said I was going to ask my manager for that raise and I haven’t done it.’ There’s got to be a little bit of this in a group of people for whom I feel as if I need to be moving forward and they’re going to ask me about it and hold me accountable to it. I think this is really important for all of us.

And you’re matched up with women across the country, or does it go by geographic area?

Dufu:  Well, the two things that you and your Cru would have in common are your time zone for scheduling purposes. And then your life stage is probably the best way to describe it, it’s supposed to be a peer group, it’s not a mentorship group. So, even though they’re in different industries, you’ll likely be with people that are at the same level as you are. Outside of that, your Cru is beautifully different from you by design, the algorithm is matching for diversity.

I’ve watched some of your TED Talks and videos and you often mention “Tiffany’s epiphanies.” So, I wanted to know:

What would you say have been some of your greatest epiphanies over the years?

Dufu:  Oh, there are so many. One is that my parents really inspire me and have said, “If you want something you've never had before, you'll have to do something you've never done before in order to get it.” And I think that, at least for women, the willingness to take risks and really push ourselves out of our comfort zone is really important.