The Difference of a Letter

From CEO to COO and Everything in Between

I suppose it’s weird to see a CEO request a COO position after six years at the same company.

I haven’t actually searched to see if this is common, but then again, Happy Hive is not exactly known for doing things normally. I’m sure for most people, it’s a demotion. For me, though, after all we’ve been through, it felt more like finally finding the right puzzle piece to complete the first half of the puzzle. Satisfaction and a sigh of relief.

So what happened?

From the start, the setup of Happy Hive was based around the idea that we really didn’t want to experience toxic work environments, miscommunications, and internal politics AGAIN. I still shudder when I remember the traumatic times, BHH (Before Happy Hive). We were adamant about setting a work culture based on communication, creativity, and open-mindedness (not that kind you’re thinking, but we do have unlimited coffee in our coworking space, so drop by!). We did output-based work since we hated counting time. We encouraged questioning the management because we wanted to improve and correct things. We did not count leaves because we KNOW it’s not just vacation or personal sickness—there’s taking care of family, mental health, and even just time for yourself. The core of all this is trust and really being able to foster an environment where everyone is comfortable enough to be open about what’s happening personally so that others may understand that these things affect work output. I think we did a pretty darn good job with this, if I may say so myself. The other parts, well, were experimental.

If there’s one word to describe how we organized management, that’s ORGANIC. We just initially randomly assigned things to each other even though we were not really experts (who is, really?), and besides, we’ll just learn on the job. The one thing that we agreed to, though, is that titles don’t matter, that our way will be democratic, and that we will ALL decide and agree on important matters. So I was assigned the CEO role; Reena was the COO; Iris was the CCO; and Ate Lei was an Administrative Consultant. There was no ego; we were equal and had equal shares, and we all received the same level of respect—that is what I thought. Oh, Cheska, you sweet summer child.

Last September 2022, I attended a workshop entitled “Drafting a Founders Agreement” by Carlo P. Valencia of Startup PH Training, an established speaker and mentor in the startup community. Before the actual workshop, he invited attendees to have a one-on-one session to get to know you and your company, which I availed of. I found it interestingly uplifting and jarring—explaining what you do and the culture you’ve set to an outsider is nerve-wracking. I remember him lauding the work culture and environment that we were able to create for our team. He was very interested in the fact that we were able to integrate empathy very well and acknowledge the human side of the business. He was, however, straightforward about one thing when I was discussing our ORGANIC management, which struck me to the core: “Really? That kind of democracy is working for you?”

Yes! Yes? Shouldn’t it?

There is a reason why CEO means Chief Executive Officer. That person should form partnerships, network, and ultimately make the final decisions for the company. If it’s working for you to have a democratic system like that internally, that’s well and good. That can also be part of the role of the CEO—to orchestrate internal decisions. Democracies have active leaders, you know. You have to take into account, though, how the outside world sees you and who really represents the company. The CEO should be the leader and should be present.

Okay, that was heavily paraphrased since I didn’t record it or anything.

Needless to say, I couldn’t sleep after that. I felt like my brain was rewinding the past 5 years of my role and suddenly picking up nuances that I hadn’t picked up before: the management team waiting for my decision on some important matter; me DREADING or outright DECLINING networking events; the difference in the effect of something being said when it’s coming from me vs. coming from another executive, etc. It’s true—the title maketh the man. Or at least has some effect because no, contrary to my naïve previous statement, we co-founders were NOT equal. No wonder it’s a title that many aspire to, but for me, I’ve realized it’s been a burden. More than imposter’s syndrome, I really can’t live up to it because I’m just not a good fit, personality-wise. It felt like everyone was humoring or enabling me in this role as well, even though I wasn’t doing anything CEO-ish. And more importantly, was I hindering someone more fit for the role because I’m there? Hello, life crisis 2022!

In true introvert fashion, it took me a while to gather my thoughts and really figure out what I thought fit me and what I wanted to contribute. What am I really good at? What am I bad at? I had to SWOT myself. In the end, I realized I like planning and organizing internal processes. I was already doing that anyway. I observed my co-founders’ work. Since we were “democratic” and constantly blurred our responsibilities, we gravitated towards what we wanted to do and/or were good at. Instinctively, I knew who would easily fit the role of CEO: Reena. She who befriends everyone in her path, resulting in a battalion of friends and contacts. She with her barrage of ideas for the company, bedamned the risks. She with the multi-tasking superpower of being able to be on top of everything at once. We were complete opposites in our working styles but jived so well in our values and worldview. I had to talk to her one-on-one. I wanted to swap letters.

The discussion was a blur. I remember opening up and saying that the workshop triggered it and that I started having doubts about myself as a leader. Reena was kind and assured me I was doing a good job, even though not in the traditional CEO sense. I was resolved to push this, though, and offered the position to her, to think about it, that with our growth and all we’ve been through, the roles would fit better. She said she would seriously think about it.

Talking about it led to the heavy (and actually pretty obvious) realization that, no, this will not only affect the two of us but the whole company. If I realized this, maybe the opportunity could also be given to the rest of my co-founders. Maybe they want a different role. Maybe they feel like they would fit better somewhere else. What are their goals? How does Happy Hive fit in there? It’s funny that we’ve been asking all of these questions of our employees but not ourselves. So we started a series of founders’ sessions with the intention of figuring this out. In the past years, we were so into the hustle of the business that we got lost in it and got sucked in. We forgot that we were the owners and that we should be the ones dictating the business, not the other way around. We apparently mostly felt stuck in our current roles and were pretty much miserable. What should the business do FOR us? More importantly, how can we be happy here?

It took months.

Concurrently, we had our strategy plan for 2023 after having none in 2022. Reviewing the previous year, I became more convinced that the role was not for me and that things would not have happened if I had had a vision and directed the company as I should have as a CEO. Earth, swallow me now. Reena had yet to give a reply, and I was talking myself into accepting the idea that she wouldn’t accept it. Hey, I know better now, right? I should make an effort to attend external events. I should practice thinking of new ideas for the company. Is there training on how to be a CEO, or at least how to act like one?

Finally, Reena put me out of my misery by accepting the offer. GAWD. What a relief.

And I was suddenly flooded with excitement about the new role. I had SO MANY IDEAS that I wanted to plan and execute. This felt right. This was as it should be.

But this was only the beginning. The transition will be difficult and will take some time, but it can be done. We needed to train people so we could let go of some roles. We needed to improve our data and figures. Most of all, we needed to continue doing what we do best: communicate. Keep discussing, keep talking with each other, keep being open about the plans to everyone in the company, and keep listening to what they have to say.

We’re still in the transition phase, and it’s been INTENSE. Monthly board meetings are back, and that’s our internal pressure to have progress every month. There are internal deadlines every week, and there’s more work than ever. There are uncomfortable discussions happening that need to happen. This is tough love, company style. The silver lining is that we are all now at least working towards a goal that we’ve all set for ourselves and for the company, and we know it will die down in a couple of months. Yes, it’s difficult, but growth always is. Throughout all these, I am absolutely grateful for the team who keeps pushing themselves to adjust to everything that’s happening, and especially for my co-founders who helped me foster this culture that reminded me that yes, it’s okay and it’s a MUST to ask for change for the better. Always.

Totally didn't edit someone into this

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