Growing as a startup leader by breaking through my big assumption

People who know me well know that I’m the type of person who likes to suss out and explore new opportunities for professional growth whenever I can. It’s why I came to San Francisco and sought out Executive Assistant opportunities. I wanted to be around smart people who cared about the problem they were solving and were willing to give me a chance to learn and grow while contributing in a meaningful way. I was able to find all of this at Xola as the Executive Assistant to the CEO, and 14 months later I now serve as Xola’s Chief of Staff. I continue to seek out opportunities to fuel my growth, so whether it’s a workshop, conference, podcast, or meetup I find myself nodding vigorously (sometimes literally but usually figuratively) when something strikes a chord. That validation is helpful — it’s always good to remember that crazy thing happening at your startup has happened before, is human, and is part of the wild, messy ride we’ve embarked on.

Enter: Fort Light’s Startup Manager Training program, a professional development workshop aimed specifically at startup managers. This two day experience is run by Stanford-trained executive coaches Anamaria Nino-Murcia and Michael Terrell, as well as Jeff Barrett, the former CTO for Stitch Fix. It’s not your average professional development workshop. The Fort Light Startup Manager Training program provides participants with opportunities engage in personal reflection, explore management concepts and strategies, and, most importantly, to put these new ideas into practice so that we left the two-day training already having begun to apply these new skills. Instead of looking at a never-ending Powerpoint to learn about feedback, we had an interactive conversation about key concepts, problem-solved real issues together with other participants, paired up and practiced, and finally put our learning in motion by taking time to plan for and actually schedule the next steps we wanted to take once we got back to work (people literally sent meeting invites, updated upcoming 1:1 agendas, and send emails to their bosses and direct reports). No more smiling and nodding to say yes we will definitely all do this ASAP when we get back to the hectic day-to-day of our jobs.

As prep for the training, I was asked to gather feedback from my teammates and manager on what I was doing well and what could use improvement in three main areas: setting expectations, giving and receiving feedback, and my support of and advocacy for others. There was also an “anything else” section. Here were some of the things I distilled from the feedback I received:

  • (Support & Advocacy) You’re often a point of contact for people in distress. You act as a great advocate, empathetic colleague, and also a source of optimism/meliorism in finding ways to improve or grow. You also spot areas where people are stagnating and flag those for awareness and potential action.
  • (Feedback) When we have [shared feedback], you’ve always done so in a patient, positive, clear way.
  • (Anything Else) You have a remarkable work ethic and you always see that things get done.
  • (Expectations) [B]e less sensitive if people ask for clarification
  • (Feedback) You sometimes seem to take things personally — even things that from my vantage point have very little to do with you, or anything you can control.
  • (Anything Else) You have your shit together so much — it’s very impressive to see someone so young in age and professional career to be so organized and on top of things. I think if anything you need to learn / grow to not let things get you down. It’s hard to not get emotional at times but I’ve seen a few occasions where it seems that actions of others can really negatively effect you (or is it affect — eh who knows).
  • (Expectations) It would be helpful for you to identify and be aware of your areas of frustration and communicat[e] that.

So that is a taste of what was offered up. I distilled all this and was finally able to name something that had been nagging at me. I put up a defensive/aggressive stance that is off putting and unproductive. Here’s what I wrote as items to work on in my distillation:

  1. Build habits that allow me to respond professionally to frustration.
  2. Work with myself and others to alleviate frustrations.
  3. The big one: Break down my defensive/aggressive response habit.

And a distillation of the more flattering feedback was to continue not being afraid to get my hands dirty and get shit done, continue looking out for and advocating for teammates across the company, and stay curious — keep learning and growing! Woof. The 2-day training hadn’t even begun and already I was feeling the potential to tackle some of these unproductive tendencies and opportunities for growth head on.

Our first day began with us looking at CORE — the stuff that makes me me, that makes me tick, that motivates me, that makes me want to punch a wall (Don’t punch walls — you’ll break your hand. Punch pillows instead). And to set the stage for the remainder of our time, we did an exercise to uncover our big, limiting assumptions — those beliefs or perspectives that get in our way in a variety of contexts without us even knowing it. After a little digging, I uncovered my top assumption: If someone gives negative feedback/constructive criticism, then they don’t think I’m good at my job or valuable to the team. Boom. I said it out loud. My top love language is words of affirmation. I seek external validation. I have a hard time seeing my own worth when others aren’t visibly/audibly appreciative. My compassion for others is stronger than the compassion I offer myself.

That all sounds pretty not ideal, but we were encouraged in looking at our big assumption to think of all the ways it has served us over the years. After all, these things help us get to where we are today. As I’ve strived to be appreciated, I’ve become a tremendous reader of people’s emotions. I’ve pushed myself to extremes to achieve. I’ve consistently shown others gratitude and sought to build them up in the ways I hope to be built up. I care about building relationships and am fiercely loyal. It is, in large part, what has propelled me to where I am today. But in all that looking out for others and learning what makes others tick I fell short in looking out for myself. And I need to tackle this assumption so that I can draw back my defensiveness, strengthen relationships, and build my self-confidence and sense of self-worth from within.

We carried our awareness of that big assumption with us the rest of the program as we tackled the topics that I had gotten feedback from my team on: Expectations, Feedback, and Support & Advocacy. One exercise from the Expectations section has really stuck with me: the idea of a “social contract” (the set of implicit and explicit expectations for how people will work together that exists in any working relationship regardless of if it has been discussed or not). After being introduced to the concept, we were given prompts to draft our own social contract in the form of a personal user manual that allows those you work with to understand your values, working preferences, feedback style, quirks and/or pet peeves, and how to maintain a positive, productive relationship based on these expectations. How amazing is that? I’d gotten feedback indicating it would be helpful for my manager if I could identify my triggers/frustrations so we could talk about them and work on improving our relationship. And now I had the opportunity, and prompts to guide me through figuring this out. In addition to completing the exercise of writing our contracts, we paired up and shared them, getting feedback from our partner on how they understood what we said so we could make sure we were effectively communicating these preferences and expectations. I loved that the program provided us with skills and strategies as well as a practice field so that we left having already started the process of implementing changes. For me this is crucial in making a difference in how I show up at work. If I let the chaos of startupland dominate, and fail to practice new skills, to try out new techniques, I know I’ll miss out on opportunities to develop.

On my first day back in the office, I sat down with our CEO (my manager) to share my social contract. I talked about how people being late makes me feel they don’t value my time. I’d rather be emailed important items instead of getting them on slack. It frustrates me when people come to me last minute needing my help and their poor planning becomes my emergency (This feels mostly preventable, be proactive!). Or if someone does need to come to me and the clock is ticking, own up to the fact that you’re asking to draw on my time and energy for something that you should have brought up sooner. Another big one: if you’re giving me feedback and I don’t seem to be taking it well, remind me of your intentions, your desire to help me learn and grow — because more likely than not, my pained reaction is the result of my big assumption beating its drum in my head.

My boss took the opportunity to ask questions, to comment on ways these had played out previously, and we made “check-in on working relationship” an item for weekly 1:1s. I went on to share my social contract with the teammates with whom I work most closely. I asked for their questions/comments/concerns on the content as well as some meta feedback on introducing the concept of social contracting to others. The feedback all pointed to the name social contracting being far more intimidating and off-putting than the exercise itself. One of my teammates put it beautifully; the social contract is a “resource not a requirement.” There is no punishment for breaking the legal sounding contract. Rather there is an open invitation to revisit and redefine as expectations are or are not met as set out in the social contract. Moving forward I’m calling it a Personal User Manual, and referring to it as an expectation setting exercise.

Shortly after participating in Fort Light’s Startup Manager Training program I went to Houston to facilitate our new hire orientation. The Personal User Manual (Social Contracting) exercise had been so powerful to me that I baked it into our orientation. When I first introduced the idea, people were generally open to it, but a few also said, “I’m so easy going. I’ll have nothing to say.” When it came time to share — lo and behold — they had a lot to say. The compelling prompts and introspective nature of the exercise helped them better understand their preferences and assumptions. And then once people got a chance to share with their manager and teammates, it opened a door for stronger and healthier relationships. At the end of the week, they commented on how valuable it had been to do this so early in their time at the company. With such a positive response the first time around I’ve included this in each subsequent new hire training and seen similar success.

Fort Light’s Startup Manager Training program provided me a mindset shift while equipping me with tools to be better at my job. And it did this in a way that had me consistently practicing what I learned both in our sessions and back in the “real world” after the close of our two days together. The lasting nature of this training is in part that for the 10 weeks after the sessions ended, we had regular check-ins with an accountability buddy (aka accountabilibuddy). Each Sunday we’d get an email from Anamaria or Michael with a prompt for our next check-in conversation. Maintaining a relationship with someone who has also been through this training has been so helpful. I get to witness the successes of a peer in her own domain; have someone to help me troubleshoot the challenges I face, remind me of what we learned, and spitball ways to apply it; and have someone with whom I can continue to learn and grow. We’ve attended meetups and conferences together, and continue to support each other to this day.

Thank you Anamaria, Michael, and Jeff for bringing this offering to startupland. I draw on the learning from the program on a regular basis, learning from both my wins and losses. As you said at the end of the program: “You’re not screwing it up. You’re figuring it out. Begin again.” So here’s to getting messy, trying new things, and beginning again when needed. Smells like growth to me.