Episode 199: OKRs, Pancake Sprints, & The Power of a 30-60-90 Day Plan: Vanessa Monsequeira (VP of People, Gorilla)

Watch our recent episode with Vanessa Monsequeira, VP of People at Gorilla.

We talked about "Process Debt", the power of having a 30-60-90 day plan as the new People Leader, and mastering OKRs with "Pancake Sprints".

If you don't have time to check it out, read the highlights below. ??

?? "Process Debt" on the People Team

Scaling a company is a wild ride, but it comes with a hidden cost: process debt.

She shared one of her biggest lessons from her time at Miro growing from 350 to 1,000 employees in just one year. When you’re scaling that fast, she says that everything becomes reactive—you’re hiring in overdrive, cramming in HR systems, and slapping on solutions left and right.

She calls it “process debt.” It’s like that cartoon where cavemen are running with a wheelbarrow full of square wheels, while someone’s trying to hand them a round wheel.

The problem? You’re so caught up in the chaos, you don’t stop to notice you’re optimizing square wheels.

Vanessa’s biggest fail wasn’t just a bad hire or a botched solution—it was not stepping back to lay the tracks for the train to move faster. And that’s the real lesson: It’s not about fixing every individual issue; it’s about making sure you’re building the right foundation for speed.

If you’re in hyper-growth mode, take a step back. Is your team running on square wheels, or is it time to switch to round?

?? The power of a 30-60-90 day plan

Walking into a new people leadership role is tough. Now imagine starting your second week by presenting strategies to the entire company.

That’s exactly what Vanessa faced when she joined. So, how did she prepare? A bold 30-60-90 day plan before she even got the job.

During the interview process, the CEO laid out her strengths and weaknesses. Instead of shying away, Vanessa leaned in. She crafted a plan that acknowledged her blind spots (using the Johari's window method) and detailed how she would close the gaps. Her approach? Total ownership.

She broke the 30-60-90 plan into three key parts:

1. People level: Direct interactions with the team and leadership.
2. People solutions: Building the right tools and processes.
3. Company level: Understanding and aligning with the broader business strategy.

Once in the role, she realized the tension between going fast and taking it slow. Within her first week, she dove into setting a vision—but soon learned the hard way. She moved too quickly and had to own up to her team.

The lesson? Slow is smooth, and smooth is fast. Take the time to listen, understand the business strategy, and align people solutions to drive that forward. It’s not about launching the perfect strategy on day one; it’s about building the right foundation.

Thinking of stepping into a new role? Craft your 30-60-90 day plan before you start. It helps you visualize the journey and shows the company you're already thinking like a leader.

?? MPL Live Miami is coming on December 10th! ??

Join us for MPL Live Miami on December 10th.

Get ready for a day packed with insights, inspiration, and networking with HR leaders.

What to expect:

??? Live Podcast (120-150 mins) – Unfiltered conversations with top HR pros

?? Networking (90 mins) – Connect with like-minded leaders and peers

This is an event you don’t want to miss. Grab your tickets now and secure your spot! ??

?? The OODA Loop

Unlearning isn’t easy—it’s hard work. Vanessa breaks it down with a simple truth: “It’s not like you have a plan to unlearn, and boom, it’s done.” Our brains don’t work that way.

So, how do you tackle the unlearning process, especially when it’s ingrained in your habits and environment? For Vanessa, it’s all about awareness and intention. It's like breaking any habit—first, you recognize it, then you commit to changing it.

Here’s a practical framework Vanessa uses: the OODA Loop (Observe, Orient, Decide, Act). This approach, borrowed from the military, is used in agile ways of working. When she steps into a new organization, she starts by making a list of observations. Then, she shares them with her team, orienting the group towards a shared understanding. From there, they decide and act on how to learn or unlearn together.

It’s not just a solo journey—it’s a team process. Every Monday, she uses something called "Monday Mesh," where she sends out a Loom video to her team, sharing observations and updates. This keeps the unlearning process open, structured, and accountable.

The takeaway? Unlearning isn’t just about ditching old habits; it’s about actively creating a new way forward. And using a tool like the OODA Loop can give you a solid framework to guide the process.

?? Mastering OKRs with "Pancake Sprints"

OKRs can be messy—especially when you’re just starting out. Vanessa shared her approach to mastering OKRs: pancake sprints. ??

Here’s how she explains it: When you make pancakes, the first few are always a bit of a flop. The pan’s not hot enough, they’re misshapen, and look kind of rough. But as the pan heats up, the pancakes get rounder and more consistent. Same goes for OKRs.

When Vanessa joined Gorilla, the People team had just two KPIs: recruitment and payroll accuracy. There was no OKR structure. So, she brought in a method inspired by John Doerr's book—it's all about learning to write good objectives and key results, which takes practice.

Vanessa started with some prep: a video to the team on how to write solid objectives, followed by a collaborative process to craft OKRs. She didn’t expect perfection; she knew the first few sprints would be "floppy pancakes." The focus was on building the foundation, or as she puts it, “laying the train tracks.”

They even used "decision poker" to decide on key results. Is the leader making the final call? Do we all decide together? The key is psychological safety. If some OKRs end up misshaped, that’s okay. The goal is to avoid vanity metrics and learn from each sprint.

Pro tip from Vanessa: After every quarter, do a retro on your OKRs. What went well? What didn’t? Inspect, adapt, and move forward.

?? The career advice Vanessa would give to her 22-year-old self

"Reflecting on the concepts of slow and fast we discussed earlier, I would tell 22-year-old Ness: Trust the pace you're at in each phase. If it's going slow, trust that. If it's going fast, trust that. And trust that you have the tenacity to make the next right step."

?? What Vanessa would fix about HR if she had a magic wand

"I would fix bias. Bias exists in all our processes—performance, recruitment, everything. Even just the slow unlearning and raising awareness could solve so much."

Go listen to the full episode: Apple | Spotify | YouTube

See you next week!

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