🤸 Sh*tty is not just okay - it's necessary, 8 traits of high-performers, & 3 things we’re NOT doing

Hey — it’s Cristina & Jenni.

Each week, we share leadership reflections, resources, and laughs to help you excel in your role (+ have fun along the way).

As two tech leaders, we’re here to “lead in public” by sharing what we’re learning in our day-to-day roles, encouraging others to do the same, and learning and growing as leaders together.

Enjoy!

What we’re reflecting on this week

Sh*tty is not just okay - it's necessary.

It took me quite a while to get my head around this concept.

And I’m not talking about quality or performance here.

What I mean is that as leaders working in dynamic and fast-paced environments, we will always be surrounded by challenges, imperfections, and things that are outside our control.

And yes, I know that things are not always going to be “perfect.” But actually accepting this discomfort so it doesn’t paralyze you is hard.

Still, it’s super important.

It’s how you grow into a better leader, a better teammate, and a better person.

As a natural problem-solver, my eyes are trained to find areas needing improvement. This strength, however, also has its fair share of drawbacks:

• When the problems stack up and resources are scarce, I can become fixated, overwhelmed, and frustrated.

• I spot the gaps and potential pitfalls in a project, idea, or proposal. And while this is beneficial, it can inadvertently paint me as a “Negative Nancy” or as not exuding enough enthusiasm.

When I worked as a consultant, this wasn't such a big deal as there were often plenty of hands on deck, endless scope reviews, and risk mitigation plans.

However, in a startup environment, you can see why this trait can sometimes be counterproductive.

Startup journeys are like rollercoaster rides, with new challenges showing up almost daily, at every turn.

These are businesses built to tackle tough problems, all while building their product in real time.

And it’s not just startups - this is true for work environments with frequent change, high standards, and limited resources.

Maintaining optimism is hard at times when trying to fix every issue that pops up or working on a project you believe is doomed to fall short of expectations.

So, what's the solution? How do we have a bias to action despite all the difficulties and challenges we are facing or may face at work, with our teams, and with our boss and peers?

We’ve come up with a 3-step guide to help you not only accept, but also expect the sh*tty, allowing you to choose the most impactful battles that are within your control.

Step 1 - Adopt a “pragmatic optimist” mindset

Pragmatic optimism isn’t about maintaining a positive attitude or being optimistic but instead about how you approach different situations.

Pragmatic optimists:

• Remain optimistic in challenging situations because they’re confident in their abilities to tackle any challenge.

• Assume accountability for their actions, which helps them feel better about themselves.

• Try new things and embrace challenges when they arise by seeing them as growth opportunities, instead of worrying about what could go wrong.

• Expect and not just accept that things can be sh*tty sometimes - and that it’s perfectly ok and part of the journey.

Adopting this mindset speeds up our bounce-back rate when we do encounter challenges.

And it prevents us from wasting precious time obsessing over problems, overthinking, or complaining, which can make issues appear bigger than they are - draining our energy and motivation along the way.

Step 2 - Pick and choose your battles wisely (this isn’t just relationship advice!)

The issues and challenges will never go away, but as leaders, we have to choose to focus on the most impactful problems.

In doing so, we can carve a path forward with purpose and clarity. Work with your team or do this exercise on your own to prioritize relentlessly:

• Identify the issues requiring immediate intervention: Which issues need urgent attention?

• Establish priority order: Which ones should we tackle first, based on their impact and urgency?

• Recognize what can be intentionally deferred: What issues, although present, can be parked for the time being without significantly hindering progress? Which things don’t really need to be addressed at all and are more nit-picky/preference-based?

Step 3 - Take small steps & regularly measure them

Start by testing 1-3 solutions that are feasible in the short term, think low-hanging fruit. Then, create a routine to consistently track progress and make necessary adjustments.

Not every challenge needs a fancy new process or a formal meeting. 

Often, it's best to kick things off with one person, make small tweaks, and build incrementally from there.

Let me share an example to bring this to life:

• At my workplace, we have a great writing culture. When we come up with a new idea or project that we want to discuss and implement, the first step is to write a proposal.

• Our proposal format includes several elements: the problem we’re addressing, our proposed solution, our target audience, an implementation plan, resources needed, and potential risks.

• But what it didn’t include was a final decision deadline. This meant we ended up spending hours (sometimes days), going back and forth over the proposal, without reaching a concrete decision. This slowed us down and got in the way of trying out new things.

• Recognizing this bottleneck, I started asking my peers to add a ‘decision deadline’ date in their proposals and eventually incorporated it into our standard template.

• Then, I worked with the CEO to set an ideal timeframe from proposal to decision - we landed on one week. And now I’m keeping track of how our proposals stack up against this benchmark, and what else we could do to speed things up.

So, instead of just venting about this to a colleague and doing nada, I tapped into my pragmatic optimism and took small steps forward, resulting in the change we needed.

To sum it all up, embracing sh*tty sometimes is a prerequisite to achieving “better.” 

Or as Voltaire once said, “Perfect is the enemy of the good.”

Accepting this truth allows us to let go of the pursuit of perfection and instead helps us to prioritize challenges and make progress, however small or imperfect.

As leaders, we’re here to tackle the right problems at the right time, not every problem at once.

As we recognize the extent of our potential and step into our roles with pragmatic optimism, we empower not just ourselves but also those around us.

→ What’s one 'battle' you’re currently trying to fight that could be put on the back burner without significantly impacting progress? What is holding you back from letting it go?

What we’re learning this week

• 🧵 Thread: Discover the 8 Traits of high-performers - Founder Matt Gray has successfully hired over 90 high-performers in the past 3 years. In this thread, he breaks down the 8 key characteristics common to all of them.

• 📚 Book: “Fast like a girl” by Dr. Mindy Pelz - While not directly related to leadership, this book offers incredible insights for women on areas traditionally under-discussed and under-taught. If you want to learn about the healing powers of fasting and how you can build a fasting lifestyle unique to your hormonal and menstrual cycle - this book is for you. We think it’s an essential read for all women seeking to take charge of their health and wellness and for the men out there - share it with your partners!

• ✍️ Tweet: Dave Perrell breaks down the 3 pillars of building a high-performing company - Guided by insights from Frank Slootman - author of “Amp it Up”. Frank has led 3 companies to their IPOs: Data Domain, Service Now, and Snowflake. We enjoyed learning about the philosophy he used to turn these companies around.

What we’re enjoying this week

This post is a great reminder of the importance of creating boundaries at work and finding what we can - and should - say no to. While aimed at Customer Success leaders, it applies across all functions.

That’s it for this week — thanks for reading.

See you next Thursday! 🤸‍♀️