Leading with vulnerability

Making agreements with Charlotte

Slowly, slowly the barriers come down between two hearts. It is a process of committing to deep vulnerability and humility, to being slow to act on flaring anger or resentment, to let waves of emotion wash through me without needing to respond. Slowly, the vulnerability and calm becomes contagious, and we can begin to connect on a human level over mutual fear and frustration, each able to voice unspoken difficulties to the other with less fear of violent reprisal. Slowly, the body, which starts in a state of heightened anxiety, calms. The voice becomes soft, slow.

In this place, I can meet what arises in myself and the other with tenderness, curiosity. A beginner’s heart. There is space to consider new realities outside of the picture I’ve constructed in judgment or anger or self-righteousness, space for the other voice to arise and exist. And in this spaciousness there is the ability to speak my own truth, in a gentle and tender way, to be heard and acknowledged, even to receive apology for words spoken harshly. There is space for there to be no right answer, just the meeting of two people with different backgrounds. There is space for expectations previously unspoken to be given voice, for agreements to form, and for each to be seen for their needs.

There is space for flower watering to come from an authentic and loving place in my heart, rather than being orchestrated, and for apology to burst forth for things I had not yet seen, hurts that I had caused. Apology that comes from a sincere desire to take ownership of my thoughts and actions, arising out love and a heightened awareness of my impact on the other. The formal ritual of beginning anew comes to life in small steps of vulnerability, hesitantly unveiling. The steps are out of order and jumbled, but exactly right for the moment.

There are no words I could have planned for the occasion, no list of demands that could have eased the sorrow on my heart. The surprise is that it is not more money that I need, but rather presence, care, gentleness, consideration of my needs and time constraints.

I see that I have been looking to Carefree to be my “stable anchor” in a stormy and changing sea, where my home is Jerusalem until it’s somewhere in California, where I carry my dearest papers wherever I go just in case. I see that it may not be possible for Carefree to meet this need, if stability is to mean structure and order and ample support. Carefree cannot afford to hire another engineer, it’s in the long process of finding a product manager, and it doesn’t have the bandwidth to setup organizational process. Charlotte is asking me to play scrappy, to handle booking my own meetings, to help out with project management. To be a leader in the organization without a title, without the pay. Because that is what the organization needs. There is no technical leader because they cannot afford one. My need for stability, unspoken, becomes an expectation that can only result in disappointment, an inability to see the ways I am being supported by Charlotte and the team.

After the conflict between Charlotte and me last year, where she offered then rescinded a promotion to CTO, my anger, hurt, and fear of being fired drove me to a conscious vow: I will not step into a technical leadership position at Carefree without a clear invitation. I’m not being paid to lead, I have no authority, I will not do anything without being asked. I’ll show them how much they’re missing. Why should I take initiative and risk being fired or disciplined for “overstepping my role”? I ceased taking ownership of my work at Carefree, acting as an individual contributor, not a leader. I constantly de-prioritized Carefree work for other activities: family dinners, friend hangouts, dentist or doctor appointments, Tamkeen.

I was able to speak aloud my anger, hurt, and fear to Charlotte today. She was defensive, replying that the company isn’t in a place to offer any technical leadership roles, and that I’m already in a place to lead as a technical strategist. I calmly stated that my contract does not define “technical strategy”, that we can craft any story we want. Let’s not debate this point. She nodded. The point is that Carefree is a startup with $60,000 left in the bank. Funding, though promised, has not materialized. They don’t have the capacity to support me in the way I’m used to. Charlotte pointed to bringing in Jahangir, agreeing to weekly tech meetings, and asking Sarine to help with functional tasks as ways she is trying to support me. But the reality is that I may have to send my own meeting invites, engage in project management, and carry some of the burden of technical leadership.

Today I allow in the thought that Charlotte is doing her best to support me in the ways she is able. She is trying, on a limited budget, to support my needs, while working 90 hour work weeks, and pushing herself past limits of what is comfortable and nourishing. The company is in a critical survival state. It may not be able to meet my needs.

That doesn’t mean my needs are invalid. My need for a stable and collaborative working environment is completely valid, and I welcome it into my awareness. Pausing. Both can be true, my need can exist alongside the reality of working for a startup in existential crisis.

If I choose to continue working here – and it is a choice – I may agree to being a little more scrappy. To doing things beyond the scope of my engineering work because that is what’s needed to keep the team running. It’s also okay to not do this, to want to exercise my unique gifts more fully, and choose to walk away.

Today I was able to meet Charlotte in her fear when she described me as an operational risk. On this I wholeheartedly agree: I am the only engineer with full insight into the technical systems and underlying code. I am too expensive for the organization long-term, and cannot commit to working more than two days per week. My heart broke a little as I saw her loyalty to keeping me and my loyalty to sticking with her: our mutual commitment to each other as a silent desire for reconciliation. I felt fragile and mortal, aware of my own impermanence with the organization.

You don’t have to keep me out of loyalty, Charlotte.
I’ve been so touched by our relationship after the difficulty of last year.
I want to plan based on what’s best for the organization.
If I leave, I want to make sure you’re in a good place without me.

I felt as if I was planning my death. I spoke gently.

I am going to leave Carefree at some point, you know. I won’t stay forever.
I might leave within five months. You know I may move to a monastery (really, Melanie?) and I can’t exactly keep a tech job there.

At this, she smiled and softened, congratulating me for that step (is it a step?).

Much of my anxiety stems from the burden of my being a very tangible operational risk. If I walk away right now, Carefree will lose valuable time and need to hire an agency or use Leandro’s team. I don’t feel like I can leave without abandoning them. I have repeatedly urged Charlotte to hire a junior engineer I can mentor and onboard, so that I can ease the transition if and when I leave.

They don’t have the means to hire another engineer. She wants to re-evaluate once we finish the technical strategy at the end of February. Am I willing to wait until then to discuss? Yes, I am – and actually, I have another idea while I’m writing.

Maybe I can mentor a Palestinian engineer friend to work for Carefree out of my own salary, giving me the ability to mentor someone, share knowledge, and have fun collaborating. This person will keep me accountable, further my own goals in Palestine, and take some of the manual work off of my plate. After the technical strategy work ends in February, I may ask about the possibility, should we need to spin up processes that require engineering talent (we almost certainly will!). There’s energy in my body to doing this path, which is delightful and surprising.

The other deep anxiety I have is that I’m not set up for success. Our digital trustee, Jahangir Khan, is proposing rapid iteration and decision-making which at first glance require a larger time commitment from me than I am willing to give. This conflict is ongoing, but today I saw Charlotte’s willingness to respect my limit of two working days per week. She invested three hours in our conversation and proposed a plan of next steps that may enable us to meet Jahangir’s requests on time. She allowed for flexibility on pieces of work that were not essential and said she’d push back on the deadline to allow for two extra weeks of work. In being met in my needs, my heart is softening to meet the company where it is, to meet Charlotte in her striving where she is.

I see Charlotte’s frustration at the output of technical strategy over these past months. My analysis has been mostly completed in silos, one system at a time, when she’s been asking me to reimagine the entire map. I just couldn’t wrap my mind around the top-down perspective, capturing high-level business processes and user stories and letting that drive a technical systems view. That lack of clarity manifested as avoidance to doing the work.

I know how to evaluate potential systems when the other pieces are fixed, but I’m new to mapping entire systems when three or four pieces are in flux. Trying to imagine this map and coming up with darkness is scary, as if I’m on shaky ground, trying to find something stable to hold when none is available. Jahangir has been critical in guiding me out of the dark, adding a framework for analysis that is efficient, focused, and encompassing of business and technical needs.

I see my frustration in attempting to offer quality work and not having that effort appreciated and seen, the difficulty of aligning tech and business goals across continents. I see Charlotte’s frustration, the pressing budget concerns, the fear that if tech doesn’t come through, the whole company will collapse. My job here is to look into an uncertain architecture map and propose something new, in a company whose future is uncertain. Part of the work is managing my fear of uncertainty.

I see that I wasn’t able to fully listen to her. I was attached to a view of Carefree centered on caregiver bookings as the central transaction, while Charlotte shifted to a view that centers on delivering CSR value to accommodation partners. Out of ignorance, flashes of arrogance, and perhaps genuine confusion, I did not fully incorporate her vision into the burgeoning tech architecture. Today I was able to speak to this confusion, asking Charlotte for patience as she repeated her ideas again.

In this place of vulnerability and humility, my mind settled and body calm, I got to apologize for completely missing her and for not delivering what she had been hoping for. Over the last two months, she didn’t feel heard, and today I could finally hear her. While I am not responsible for her fear, I am responsible for how I show up. I can do better at deep listening and patience with our gaps in perspective.

During our talk, I saw that I was not registering everything Charlotte was saying. I spoke aloud that auditory learning is difficult for me, and writing helps me to concentrate and process. I began detailed, almost word-for-word notes to drive towards full understanding and concentration. I see that sometimes in technical conversations with non-technical people, listening is a challenge for me. Sometimes I gloss over pieces I disagree with or don’t understand fully, perhaps stemming from arrogance or impatience. I will try to listen with more rigor.

In this conversation, I participated in the delicate act of revealing my heart, slowly, and then more fully. My vulnerability was a gift, enabling Charlotte to touch into her stored anger and to release. So too was her ability to meet me in my earnestness.

I plan to adopt the following agreements in my work with Carefree:

• I agree to taking ownership of my work and doing more project management when needed.
• I agree to recognizing that Carefree is a startup with extremely limited resources, and I may not always get full project or product support that I would at a bigger, more established organization.
• I agree to working 2 days per week.
• I agree to take notes when Charlotte is talking and to send her notes when our call is completed, to make sure I am hearing her clearly.
• I agree to be open about my plans to leave Carefree, to give at least one month’s notice, and to devise a transition plan for future engineers.
• I agree to recognize that if I want true support and collaboration, I must also see my work as a collaboration, rather than an agreement with unequal distributions of power (where my needs as an engineer are valued more than the needs of the business).
• I agree to keep my heart and mind open to leaving, and to the possibility that my needs can be better served in another job opportunity.

That’s it for now. I’m arriving to Paris in a few minutes on the train from London, ready to be inspired tomorrow. I’m already inspired by the power of vulnerability today.