An Interview with Holly Delany Cole, The Haas Leadership Initiatives


Holly Delany Cole, Director, Flexible Leadership Awards, The Haas Leadership Initiatives

Empathetic. Direct. Restless.


Tell me about your current role. Holly Delany Cole

I help to shepherd resources to Haas, Jr Fund grantee organizations so they can invest in themselves and build individual and organizational strength and preparedness. These organizations are working to defend and advance the rights and quality of life for immigrants and LGBTQ-identified individuals.  Some are advancing education equity in San Francisco by closing the black-brown student achievement gap. They are in the thick of things.  I do this work in collaboration and partnership with a team of talented organizational development practitioners and a small staff team inside the Haas, Jr. Fund.  (Holly Delany Cole pictured at right.)

 What are some of your career highlights?

I have many: helping Chicago Commons, a Chicago-based settlement house working in the West Town and East Humboldt Park communities to win federal, state and foundation support for their mission.  One of the grants I helped to design and prepare brought in over $1 million for youth and family services. Chicago Commons continues to thrive.

Creating space and resources for the community – both the practitioner/service community and philanthropic community in NYC – to form what would become the NYC Immigration Coalition.  Another organization I helped to establish was the Fund for New Citizens initiative which recognized that the coalition groups would benefit from capacity building support.  I was a young program officer and figured out then that grants mattered, but convening, connection, exchange and trust mattered more. It’s amazing that both organizations still exist to this day. They were formed in 1986 in response to the Immigration Control and Reform Act signed by Reagan; it was a crisis policy dilemma that caused practitioners and philanthropists to come together.

Another highlight frankly was every day at Community Resource Exchange (a nonprofit management support organization based in NYC) where I had the privilege of working directly with leaders and help to make something go easier or work better for them and their teams. Our support was always in service of leaders so that they could focus, and be better positioned to effectively address the variety of social problems affecting the quality of life of the most vulnerable, elevating community voice and power…doing the work that has to be done to get to the kind of community we deserve.  

If there was a headline for your leadership journey throughout your career, what would it be?

It’s possible to find and do work that matters, and do it well, wherever you are, whatever position you hold. That headline comes from feeling a little lucky. I’ve gotten something for myself no matter where I worked. Mostly I’ve been with terrific organizations, however, early in my career I was at a series of organizations with not such strong leaders. I didn’t have work that was filling me or organized in a way that I could have impact. I learned even from that…I learned what not to do.

As just one example, I worked for an economic development corporation with a three or four person staff. The leader was often absent. And when he was present, he offered little direction. A lesson, among many there, was a reflection about what is necessary to bring a team together and what one should do to productively onboard people.

Naturally, I didn’t always enter organizations near, or at, the top. I joined the New York Community Trust as a program assistant and moved up to program officer in part by understanding the goals of the people I was supposed to support and advancing work in ways that met those goals. At every moment I wanted to be my best self and deliver best value. Give me a broom and I will sweep that room. I can learn from any situation.

What are your favorite types of challenges?

I’d rather not have challenges, though they exist at every turn. And I definitely do not have favorite challenges. I am most frustrated by challenges that are caused by people careless with power and protective of their egos. I am least frustrated by the ones that engage our best selves in figuring something out – challenges that require our genius, our persistence, our resourcefulness, craftiness and creativity, our connection with one another. 

What I strive to do wherever I am is be part of noticing or finding the truth of something – the ‘what truly matters’, and getting other people to care about that, and not the attendant bullshit. I aim to light the fires in the right places and snuff them out where they are a distraction.

We are not always in control of every part of our environment or institutional experiences. The most frustrating challenges often relate to being on same team with people who are centering themselves over the work and over everyone else. Early in my career, I endured working in colleagueship with someone who was very narcissistic for six years. So that I could hold the ground in the face of such team members I recall making painful choices – choosing how best to mask myself to get what I needed, and considering what I would have to undergo in order to get done the what I wanted to get done.

People like that have shown up in almost every place I have been. I don’t always choose to work around them – I also try to influence them, change them or get them to exit…However, I have not always been in position to get them out of the organization; sometimes these people have been my boss. When I have had more formal power and agency, I’ve been able to employ strategies that are more in line with how I want to be in the world and show up for others in the world, for example, by calling the difficult teammate into learning with me, or easing their way out of the organization.

That sounds exhausting. What toll does all that contorting take?

When I was younger and had a smaller support network, I went to see a therapist. I wasn’t sure how to navigate the complications at work and my reaction to them and wanted to talk it through with someone who didn’t have a stake in my world. The therapist was helpful. In the end, I learned a lot from this early experience with a negative supervisor. I understood that continued association with that kind of person would take a personal toll on me, as would working in an organization with such severe power imbalances. Going forward, I committed to make more intentional choices about where, and with whom, to put my energy and time.

I spent more time clarifying expectations and asking questions about culture to better discern what I was signing up for!  The experience mostly taught me that I should not tolerate such behavior from anyone – it wasn’t my responsibility to mask myself or do the contortions. That’s something I didn’t know as a young woman. I didn’t have as much experience, have the support, or know how to navigate.  I rapidly learned that it’s too painful to do all the work. It’s an outrageous notion; it’s an injustice. This isn’t how people should be with each other.

Later in my career when came up against this type of person again, I did no cloaking and was more in their face. Over time, I became a better advocate for myself and less tolerant of negative behavior from difficult colleagues.

What is one book that was meaningful or influential in your development as a leader?

There isn’t one book. Any book that offers a way for me to come fully into my humanity has helped me reflect about what sort of leader I want to be. Langston Hughes’ poetry, the biographies of Thurgood Marshall, John Lewis and Paul Robeson, the writings of many, many deep thinkers including Toni Morrison, Brené Brown, James Baldwin, Octavia Butler, and Daniel Kahneman. Recently, I have appreciated emergent strategy by adrienne maree brown.

Work in the social sector can be very personal and linked to one’s values.  Can you think of a time when your values were in tension during your career and how you reconciled that tension or not?

Yes, I led an organization for four years, one that I had been with for many years in various roles, including in senior leadership. Once in leadership, I did not act on as many of the best principles and practices about board partnership as I should have. I did not have courageous conversations with my board, which they needed, and which I needed, at various points. And this led them into, following my departure, to a series of unfortunate decisions that have harmed the organization. Not irreparably thankfully. But I could have helped them be a different kind of Board. I see this more clearly in hindsight.  

Related to this, and complicating it, was that I was a Co-Director, and by the end of our four years together, I was no longer having brave conversations with my Co-Director. I was not operating with my values of regularly telling my truth and deeply listening. I fell into wanting to protect my colleague’s personal feelings. I did not reconcile the tension. I withdrew instead of stepping up more forcefully. Some of this was because I was not confident in my views – I could have invited more conversation or sought help of an outside coach. This was not my strongest leadership moment.

I have always been bothered by misalignment of values between thought and action, and one of my regular habits is to consider questions about ‘am I working in alignment with my values’ as a touchstone. I give room for evolution – I ask myself, has a deeper analysis of this kind of thing caused you to shift in your sense of this? The consideration of how am I working to advance, and in alignment with my values, is daily work. 

For a lot of Black women, their chance at leadership will come by rising up through the ranks. If I were called to do this work now, I would know to ‘re-contract’ as I take up the new role – engage with the board and staff to reset agreements about our practice, our culture as well as vision. I paid attention to the vision part, but not to key aspects of practice or culture! My reflection on why — I had been at the organization for 14 years in various roles before I was invited to step up as co-director.

The board had an experience with me, positive, and highly familiar, and there was a ‘family’ dynamic at play. Challenging family about behaviors you endured before when you were not the leader, may be a ‘harder lift’ when you ascend to that position internally. How do you re-contract skillfully as you are promoted within? How do you help people who thought you were fine with the way things were, hear you when you say things need to be different?

The co-director and I remain friends; I love and adore her. Before taking on our new roles, we had the usual conversations about how we wanted to be with each other. We decided to share an office to facilitate communication. Many things we did well and it seemed great for the first couple of years, but when analysis of what needed to happen for the organization began to shift based on our roles (I was more external facing), our visions began to diverge and I didn’t do enough about it. I didn’t call a coach and I didn’t want to go the board and say ‘choose’. Why didn’t I ask for help? Those were not outstanding leadership moves. Some of it was about caring for her; some of it was also became, my not wanting to do the work anymore. I lost interest in fighting for it.

Summer 2017, Democratic Representative Maxine Waters coined the phrase, “reclaiming my time,” as she thwarted Treasury Secretary Steven Mnuchin’s attempts to waste her time with nonsense.  Can you share an experience in the workplace where you have had to reclaim your time?  What was the context? How did you navigate it? What was the outcome?

Yes, as a new staff lead in an organization, I inherited a team. The previous director of this team (now in a different role) had strong negative opinions about a couple of the people with whom I would now work. She attempted in various ways to influence my thinking about what should happen with those individuals in MY team. I had to push back hard at her and very explicitly say, you’ve got to let me have my own experience of these individuals and also be okay with it if my sense of them is different than your own. It created distance between me and this colleague, which only increased over time, and that was okay by me. In fact, I did have a different experience of the team members that she focused on as well as of the team in general. You have to trust yourself.

What’s your approach to self-care? Are there any rituals you use to survive and thrive?

Taking care of body and mind: yoga and other physical exertion are on the calendar of things that must happen each week, as well as mindful eating.

To nourish my mind: my book group community (I’m in two currently), and my bid-whist community. Saying yes often to invitations to be in creative spaces, outdoor spaces, to new opportunities…being with family and routinely connecting young people of color with opportunity.

Taking action as a citizen and serving outside of work: I serve on two boards whose missions align with my view of the world. I have often maintained roles on boards, but not volunteered in other ways. Now I have more time since I am not leading a nonprofit, raising $4m, relating to a board of directors, etc. I have abundant energy and time in this moment.

I believe the carceral state is the most pernicious manifestation of racism, so I am working with other volunteer citizen activists to de-incarcerate Alameda County and achieve true liberation of people at the human or policy level. Action is self-care for me. And wine.

What advice would you offer other Black women trying to develop or amplify their voice and become self-advocates?

  1. Explore self, get to know yourself deeply and listen to that inner voice that tells you who and what is good for you, in your true interest, and who and what is not.
  2. Value yourself. Value yourself. Value yourself. Acknowledge your genius. Surround yourself with people who value you and acknowledge your genius. Get yourself into communities that love you…that appreciate you. This is not the same as surrounding yourself with people who only praise you and never offer critical insights.
  3. Use feedback to grow. Ask for it from trusted partners. Roll it around in your mind and act on the things that make sense to you.
  4. Listen deeply to others.
  5. Ask for help when you need it. You don’t have to know it all.
  6. When you meet people who you’d like to get to know, ask for a meeting, a coffee, a conversation. Actively expand your network, and don’t worry about the ‘no’s’. Find the yeses.
  7. Learn and continually deepen your analysis. Learn and grow. 
  8. Kindness in speaking creates confidence. Kindness in thinking creates profoundness. Kindness in feeling creates love. Not an original thought, but sentiments that I have seen roll out well in practice. Sometimes attributed to Lao Tzu; others say no.

If you could change the social sector in a way that would benefit, lift up, or affirm Black women, what would that change be?

Deep racial equity work, transformation, organizational change work begins with curiosity on the part of sector leaders, and includes listening to Black women in the sector, in the organization, in the community about their experiences and their ideas for solutions.

Have organizations interrogate the way they are organized. Invite them to get closer to purpose and mission and rid themselves of the practices, policies and habits of culture that shut Black women down and out.

Reconsider habits and practices that do not invite in, build people up, and broaden community.

Question regularly. What’s a preference? What’s a requirement? What’s a tradition? Why are things done this way and not some other ways?

The sector is informed by a culture advanced by organizations in it, organizations which are in turn composed of people who form and lead micro-cultures. Got to start with the people.

Commit to hiring Black women.

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