Falling Back in Love With Start-Ups

sarah caliendo
May 23 · 6 min read

Life is a bunch of iterations that take you in exciting places if you slow down to explore them. I used to think there was a destination, with one path to get there…then ta-dah — life would be figured out! Wrong. There’s a lot to be said about working on anchored goals, but they can also become restricting. Eventually I realized departing from a set path can be illuminating as long as the deviation is methodical.

Jess and I were getting traction on our women’s leadership focused start-up, but we were also running out of cash. I shared my exasperation with my partner at breakfast, went into amygdala hijack, and finished with a pity party — a la “I’ll die before going back to work in house.”. I was convinced we’d lose momentum on our business, that I’d failed, and worst of all —that I’d lose the newest version of myself I’d worked tirelessly to cultivate.

I wrote, and that’s when I landed on my intense romance with start-ups. I’d been working with them as a coach, but it had been a few years since I was on the inside experiencing their glorious ups and downs. The obvious aspects I loved surfaced, and then I got to the meat after asking myself questions:

  • What inspired me about my current “unrelated” roles like coaching, and where are the connection points to tech?
  • What am I missing, and how would closing those gaps serve our long term business?
  • What are the unsexy, albeit important things companies need done that I love and do well?

None of the things I was telling myself are true. In fact, going back in house would be positive, because I’d work on things that make my heart sing, and sharpen my abilities while we bootstrap our venture. Also, a company would be getting me at my best during a crucial time for them.

What excites me and what I do well, revolves around People. I build high performing teams for companies primed for growth, during some of their most exhilarating and tumultuous times. Here are some aspects I got clear about when reminiscing. They help me articulate my value to prospective companies, and to myself.

I’d own people strategy

Grit, agility, creativity, and a strong operational foundation are crucial for an early stage company, but you only get these with a deep leadership bench. Founders won’t raise money or progress without more than the few experienced leaders building their business. Yet, People strategy falls short due to lack of resources and raw skill, among other things. When People get resourced, it’s often for the bare minimum like recruiting, which is scary because People is so much more. I’ve never had a formal HR role, but I’ve spent my entire career navigating the complexities of People, and to me there’s nothing more fun or necessary than that.

Thoughtful, objective hiring

The hiring process is broken for a number of reasons. A key, yet ignored aspect is knowing exactly what one needs in a person, then fairly assessing them based on those needs. Companies miss out on diverse perspectives needed to innovate, and make costly hiring mistakes from their lack of investment in the process. While this is maddening it’s also gratifying, because I’m passionate about taking it on. Owning it all doesn’t scale, but no matter — because in pre-growth, you’re setting a foundation; if you hire the right people, together you create frameworks and hire more that do.

I also get to craft a sound candidate experience. The war for talent is brutal, and when you’re a lean company, you need to compete on dimensions other than compensation. I’m passionate about treating candidates with transparency and care during the interview process so they want to work with us. When they start, then comes development and support so they stay and grow along with the company.

Making myself obsolete

In my roles, I spend a lot of time fixing structural issues that increase efficiency and effectiveness. My goal is always to build an organization so strong, it runs autonomously — and after awhile, if my team needs me, I’ve failed. People will only stay and grow if they’re happy and connected to their manager and work, and so engaging and growing leaders starts with building authentic relationships with them. I’m an operator so I have a method, but it’s also an art (we can sense a leader being disingenuous or just going through a linear list of to dos, and it feels gross.). This is a messy and challenging process I adore.

  • Cultivating trust — Listening/learning about peeps, as well as creating a safe space to destress, discuss what’s really going on, and what we should do about it. If this falls flat, you and your cause are lost.
  • Consistent communication — Anticipative, direct, responsive, and catered to audience and context. Providing feedback is a big component.
  • Operating as a team— Doing what they do evolves into a cocktail of delegating, shepherding and finally, self-sufficient collaboration.
  • Stretching — Providing opportunities for exposure/expansion at the company, and backing what nourishes them beyond their role/business
  • Empowering ownership — Giving clear expectations/support for success, allowing mistakes, course correcting, then becoming independent.

Communication mine fields abound

I’ve always been a pretty good communicator, but I took great communication for granted until my career in tech — then, I really understood its value. Bad communication is everywhere even at senior levels with brilliant people, and even in the early days when it’s “easiest” to manage. If you can’t communicate well, you can’t develop trust, and without that you’re done for. I mentioned some tenets of good communication, but let’s focus on a couple of the bad ones I enjoy.

Conversations everyone avoids

I love the classics around feedback (positive and critical), performance, and of the general interpersonal nature. Now, if I had a dime for each time a client told me they hadn’t spoken to a person(s) they had an issue with, I would be funded, and wouldn’t be writing this post. People avoid having crucial conversations because they’re difficult! They evoke fears like:

  • I don’t know what I’m doing, I screwed up and I’m a bad person causing someone to suffer
  • This will be emotionally charged and exhausting, I will be uncomfortable, and I won’t know what to say, or how to solve this
  • I don’t want to face the consequences of saying this, and I can’t predict the outcome — so I may be disappointed

I’ve experienced them all, along with palpitations and procrastination. So why do I love them? There’s an immediate sense of relief I get when I’ve said my piece, and hear theirs. I’m fascinated with people. I feel accomplished after I’ve diffused emotional tension and addressed what no one wants to touch. I also dig process, and there are concrete ways of addressing fears that yield productive conversations that solve business needs — which at the end of the day, is why we’re all there.

Quenching information droughts

In the absence of data, we always make up stories.” I grew up with anxiety, and without information laid out for me, my mind created tall tales. I did this more than the average person, but this is a process we all endure. So even if our intentions are good, without reliable “give and take” information, people lose trust, and are rendered powerless to achieve goals, and manage pitfalls. The absence of communication can be distilled into three types (or a mix):

There’s a lack of understanding; its importance, impacts, and audience(s). Getting a grip on these can set you up for success in a number of ways, but not doing so can have dire consequences for a company gearing up to expand. An understanding of them is vital when pivoting, or reorganizing teams to accomplish new or more aggressive goals. Reorganizing can result in lay offs, intense stress, new responsibilities, lost productivity, service drops, and bad morale, but good communication allows you mitigate them all.

There’s also a belief in little or no transparency, but I won’t spend time on that, because if that’s your stance at at a company, we wouldn’t be working together. That aside, inadequate resources/desire are attributed to lack of understanding and just not having enough time as you grow.

This all said, establishing solid communication is a core reason I’m brought on, and it’s a fundamental value I instill in my team. I fill in these gaps. I take great care to understand people, and this is an area where my empathy shines. I love connecting the dots between teams and customers, giving them a voice, and meeting their needs.

Starting fresh

Even the best companies have these problems to fix, and are able to fix them with or without my help. And while I’m not sure which company or role I’ll land in, I feel great knowing the wealth of positives in them, and that I can contribute to improving them. Oh — and there’s the exploration of yet another Sarah iteration to look forward to.

sarah caliendo

Written by

Bringing humanity into business. Executive Coach. Startup ex pat. Instructor at CycleBar. Creative. Passionate about people. https://www.sarahcaliendo.com/

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