Some Days Just Suck

Building a great company isn’t complicated, but it is hard. Hard because it takes discipline (a lot of it). Because it requires making tough, often painful, decisions. And because it demands relentless, sometimes uncomfortable honesty about where we are, what’s working, and — perhaps most importantly — what’s not.

As I shared in a previous blog, Ninety’s Senior Leadership Team recently committed to an intense quarter-long review as part of our new annual discipline of zero-based budgeting. Despite the name, this process isn’t just about budgeting. It’s about evolving as a company. When done well, it surfaces the hard truths we often avoid and gives us the chance to:

1. Take an honest look at which Seats we need to fulfill our goals and which we don’t.
2. Reevaluate structure to arrive at the most productive arrangement.
3. Determine where there’s been too much or too little investment based on the goals we’ve set out to achieve.
4. Take a more objective position on ideal structure without making the exercise about the people.

None of this is easy by any means, but if you follow the process through, you’ll walk away with the clarity to make the right decisions, even when they’re the hardest ones to make.

Make the Right Decisions, Not the Easy Ones

As valuable as this process can be for shaping the future of an organization, the reality is people do occupy the existing Seats. And people are the most precious and valuable assets any company has. That’s what makes this work so hard. Because when you reevaluate everything based solely on what’s needed to achieve your vision, you almost always find a handful of Seats that no longer serve the future you’re building toward — and just as often, you identify new Seats you need that didn’t exist before. Unfortunately, the people whose Seats are no longer needed rarely have the skill set or desire to sit in the new Seats you do need.

As leaders, we want to make the right decisions — decisions that not only set our company up for long-term success but also give our team members the best chance to thrive in their roles and grow in their careers. That’s much easier said than done because as humans, we form emotional connections that supersede logic when those bonds are threatened. This is one of the main reasons so many leaders shy away from doing this work. Because the decisions we have to make touch the lives of the very people who have helped us get to where we are. And at the end of our structural review at Ninety, we faced a hard truth: Several Seats no longer made sense.

Throughout the review process, we also took an in-depth look at our company-wide performance standards. This was a lot to take on, but new leaders had started working for us over the course of the last several quarters. Many of those individuals, coming in with fresh eyes, found there were a few people on their teams who were either sitting in Seats that weren't the right fit for them or who were struggling with the change that comes with a rapidly growing business. They also found that the stronger performers on their teams wanted to work with other strong performers. With this in mind, we decided now was the time to reinforce our A-Players Framework, which I’ll share more about in an upcoming blog.

At the end of the day, this is what it means to lead. To do the hard but necessary work of aligning all the parts of your company with your vision — even when it disrupts relationships you care deeply about. Making the right decisions doesn’t mean they’re painless, but they ultimately give your company — and your people — the best possible chance to grow into what comes next.

Hard Decisions, Honest Conversations

After taking an honest look at both our structure and our people, we were faced with a painful but necessary decision, one of the hardest decisions many leaders have to make. We had to say goodbye to people we care deeply about. I say care (not “cared”) because we do still care about them, regardless of whether they’re working at our company or not. They were part of our tribe, and they matter to us a great deal. These people will always be a part of our company’s legacy, and we wouldn’t be where we are without them.

Getting to this point was a long and difficult process we didn’t take lightly, and it included the brutal day we had to say goodbye. We did everything possible to ensure a humane process, including:

• Personal support and discussions with each person
• Severance packages with interim healthcare
• Outplacement support to help them land on their feet
• The option to share their contact information to stay in touch with colleagues who had now become friends

Letting go of good people sucks. There’s no other way to put it. Losing colleagues, especially those we care about, is painful. But in the end, I truly believe it was the right decision for everyone involved. This wasn’t about finances — we still have plenty of cash. And it wasn’t about losing faith in our vision. If anything, our belief in what we’re building has never been stronger. This was about making sure we have the best structure in place to execute our next stage of growth. And for that, we need the right people in the right structure who want to play the game at a high level.

Simply put, we needed the best team on the field.

A Big Lesson Learned

This process forced me to confront my own assumptions. For years, I’ve said we’ll do everything to avoid layoffs — that they’re a sign of poor leadership. But I’ve come to realize layoffs aren’t just about financial necessity. They also happen when Seats no longer make sense, even when the people in them are great.

My disdain for layoffs and my vow to avoid them whenever possible remains. But I’m not perfect, and more deeply appreciating the nature of a layoff has been a humbling realization.

Beyond the structural changes, another revelation emerged: We had people struggling in their Seats, and those struggles weren’t being addressed. Some team members privately shared they had known about certain issues for months, even years, but didn’t feel like they could raise them.

That’s on me. As a founder sitting in the CEO Seat, hearing this was deeply disappointing. As a result, we’re introducing a new leadership standard at Ninety: Succeed or escalate.

I’ve discussed the succeed or escalate mindset in a recent blog, and while it isn’t new, the reason we chose to embrace it now, in this way, bears some explanation.

At Ninety, we’ve always said we’re a learning hospital — a place where we embrace growth, mistakes, and learning. That applies to everyone, myself included. If we’re anything, we’re transparent and humble (if you’re not a bit embarrassed by who you were three years ago, you’re likely not growing).

But one of the biggest lessons from this experience was realizing we needed to say out loud something I'd assumed was already clear: If you’re struggling with something — whether it’s your own responsibility or a systemic issue — you need to escalate.

Escalation isn’t failure. It’s a responsibility. If you’re facing a challenge you can’t overcome, you escalate. If you see something broken that’s not being addressed, you escalate. If you feel like your concerns are being dismissed, you escalate.

This is now a guiding principle at Ninety. Failing to escalate is the real failure.

If we'd reinforced this principle earlier, some of the struggles we uncovered could have been addressed before they became reasons for restructuring. I'm super focused on making sure this doesn’t happen again.

The Bigger Picture

We’re not here to build just another company. Ninety is a mission-driven organization. We exist to help leaders confidently navigate the challenges of building, running, and scaling great organizations — companies that are extraordinarily productive, humane, and resilient. That means we have to practice what we preach, which includes:

• Always aligning structure to strategy: If the company evolves, so must its structure.
• Holding high performance standards: We consistently reinforce our A-Players Framework.
• Creating a culture where escalation is the norm: If something is broken, speak up.
• Leading with transparency and humility: We’re not perfect. But we’re committed to learning, adapting, and improving.

This is part of the Work we collectively do, and this is what it takes to build something that lasts.

A Call to Action

If you’re a founder, leader, or team member reading this, I challenge you to ask yourself:

• Am I proactively reviewing my organization’s structure or just reacting to problems?
• Am I holding high standards, or am I tolerating mediocrity?
• Am I creating a culture where people speak up or one where problems are buried?

If you haven’t made escalation a guiding principle, start today. The best teams aren’t the ones that avoid problems. They’re the ones that identify and address them early.

At Ninety, we’re committed to being that kind of company.

I love this game. I love this company. And I deeply believe we’re exactly where we’re supposed to be, learning the lessons we need to learn. This process was painful, but it made us stronger. And that’s what companies that aspire to be great do. They learn. They evolve. They get better.

Even when some days just suck.