Personalizing the System Issues: A Startup Lesson

I’m a fan of accountability. Always have been. It plays directly into my pillar around “fairness” and into my pulse line of meritocracy. I very much believe we can all do better…every second, of every day. Every failure is a moment for learning, and every misstep is an opportunity to stand up and truly stretch into a taller, stronger version of yourself.

With such a strong sense of accountability and yearning to make every day better than the last comes the shadows of that – the self-criticizing, the self-doubt, the internalizing of everything so deeply that you are constantly shaking yourself at the core. I believe this has made me a great fit for startups. This ecosystem is built on over-achievers and life long learners.

Today, over coffee with a friend, I had talked for about an hour on challenges that have been on my mind. I walked through team dynamics, miscommunications, and the outcomes that  have left me pretty confused. “What am I doing wrong?” … “How can I communicate better?”…”What’s going on with me?”…were all questions that came up.

I then quickly spoke to other, seemingly unrelated challenges I’m seeing around the office. I easily dismissed them with the appropriate startup dismissals – “people are stressed given how hard everyone is working” and “this is a critical season” and “everyone is feeling it.” She quickly pointed out to me that maybe this was all related…

Maybe “my” issues were also a result of “system” issues.

Whattttt. Synapse fires. Boom. Bam. Maybe they are?

I think in startups there is such a focus on being “all in” and that has huge implications on our bar setting. It directly correlates with a promise to always do your best, to always do better. The flip side of that is if things seem hard you quickly assume “you aren’t doing your best” or even worse “you are failing at everything” [enter dramatic music here.]

This sort of either/or is paralyzing. It’s exhausting. The more likely truth is the both/and scenario – I could be doing better in areas and the system itself could be doing better in areas. It’s a shared weight of challenges that are feeding each other in a flywheel capacity.

Now I don’t want to go making excuses for anyone, especially myself. I still very much believe every challenge presents a lesson, that if we internalize, can make us better. But I do want to call out – that it’s our responsibilities as leaders to take a step back every so often and call out the systematic issues that are causing the ripples which build into waves and compound into tsunamis. Perhaps it’s organizational structure, or communication models, or old habits that need to evolve to fit your companies next season. Perhaps it’s organizational debt that has accumulated after so long of moving fast and pushing hard. At Porch, we have grown faster than most companies, and with all of that momentum comes systematic debt. It’s up to the team to parse that debt for what we need to improve, what we need to let go of, and what we need to replace.  It is much easier to personalize the challenges than to dig into the systems that may be causing them.

But are you asking yourself, “what could we as a company be doing better?”

I, myself, have always been a fan of retrospectives. They are the perfect mix of self accountability and systematic evaluation. See an issue that keeps popping up? Get the group in a room, shine a bright light on it, and leave the retro with a list of improvements – both personal and systematic ones. Look for trends, consider every habit, every assumption and every value – up for evaluation. Crazy I know.

It’s these sorts of parallel and often systematic improvements that make great companies. Companies that can commit to becoming better organizations as well as empower their employees to stretch everyday – win. They win in every way.

Not to mention – all that learning that takes place. The older I get and the more startups I build, I have begun to realize that stretching yourself every day is pretty much the point. It’s the motion we’re all addicted to. Whether it be forward, sideways, or otherwise, we’re not a stagnant species. Startup lovers are addicted to motion.

Afterall, if we aren’t pushing, stretching, growing, and improving…how else would we change the world? Impact demands momentum. 






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