Why We Built Ask Maz: Helping Leaders Build Stronger Companies

Most of us don’t wake up wishing we had more information about the company we're building. We already have plenty coming at us from every direction: weekly numbers, team updates, customer conversations, follow-ups from meetings. And that's just the beginning.

The harder part is pulling all those pieces into a clearer view of what’s really going on inside the business, then using that context to make the next right decision.

The longer I work with AI, the more I deeply believe it can help leadership teams understand their business better so they can build stronger, healthier companies and lead with more clarity.

For a decade now at Ninety, we’ve walked alongside founders, CEOs, and leadership teams working to bring more structure to the way their companies operate. We’ve built tools to help them clarify their vision, strengthen accountability, run better meetings, and execute with more confidence.

But once you have a system in place, the hard work isn't over. Every commitment, number, decision, and responsibility carries information about how your company is actually operating. As leaders, we need to learn how to connect those pieces, understand what they mean, and decide where our attention will create the most value.

Are we measuring outcomes or activity? Are our priorities still the right priorities? Are the same conversations coming back because we haven’t solved the right issue yet? Those are the kinds of questions that help high-performing teams move forward.

That’s the heart of why we built Ask Maz.

Ask Maz is our AI companion inside Ninety. It’s not meant to remove humans from the work or to replace our experience or judgment. We built it to help leaders make sense of what they’re seeing inside the business and get to clearer next steps faster.

That’s where Ask Maz begins: with the belief that better questions, grounded in the reality of your business, can help you lead with greater focus and build a company that lasts.

Asking Better Questions

A business operating system does a lot of important things. It creates shared language, clarifies goals, defines who owns what, and makes priorities visible. It gives teams a place to identify issues getting in the way of execution, track commitments, and stay aligned around the things that deserve attention right now.

But once all of that is in motion, leadership teams still have to interpret what the system is telling them. This is where leadership gets harder. A Rock can be off track for ten different reasons. A Scorecard can look healthy while hiding a weaker outcome underneath. An issue can appear tactical, then connect to a deeper accountability gap. A team can have plenty of activity and still not be getting the right things done.

That’s why leaders need a better way to understand what they’re seeing, not just another way to report on it.

We designed Ask Maz around that belief. Instead of asking people to hunt down context from different tools before every major conversation, Ask Maz lets them start with a simple question, like:

• How are our company Rocks looking before our Quarterly Planning Meeting?

• What Scorecard data deserves our attention right now?

• What recurring issues have shown up across leadership meetings over the last 90 days?

• Which Rocks are least connected to our 1-year goals?

• Where should our leadership team focus before the next meeting?

These are the kinds of questions experienced leaders already ask. Ask Maz gives you a faster, more grounded way to explore the answers so you can walk into the next leadership conversation with more context and a clearer sense of the decisions in front of you.

Why Ask Maz Belongs Inside the Operating System

Ask Maz has been part of our thinking for a long time. We began shaping the vision for it years before this launch because we believed AI grounded in a business operating system could help founders and leadership teams build stronger companies.

AI has always been interesting, but it wasn’t reliable enough for the way leadership teams do their most important thinking. That’s changing. We’re now at a point where AI can help leaders do more than summarize, draft, or brainstorm. Used well, it can help connect ideas, commitments, numbers, and ownership in ways that are both difficult and time consuming to do on your own.

Ask Maz isn't a generic chatbot with a Ninety label on top. It was designed around how leadership teams actually use Ninety to run their companies.

Ninety already helps teams manage the essential parts of operating their business: running meetings, setting Rocks, tracking Scorecard data, solving issues, and so much more. Ask Maz sits inside that environment, which means leaders can ask questions connected to their real operating data.

Yes, generic AI tools can absolutely be useful. I use AI every day, and I strongly believe founders should become more familiar, comfortable, and competent with it. But the problem with generic tools is that they require you to feed them all of the context and explanation before they can help with company-specific questions.

Ask Maz starts closer to the work. It understands EOS® concepts. It understands Ninety’s tools. It answers your questions using your information already inside the platform. And when you get answers, you can create issues, To-Dos, and Headlines from the conversation. That means you can move from insight to action faster.

One of our clients shared, “What made the experience especially powerful is that Ask Maz already understood our business context. I could get relevant, thoughtful guidance without having to explain everything first.” That’s the experience we were after. The best answers come faster when you don’t have to rebuild context from scratch.

Ask Maz is also designed to respect the way healthy companies already work. It draws from the information your Seat is meant to see so the answers stay aligned with your roles and responsibilities. A founder or admin may need a broader company view, while a team leader usually needs context connected to their team, their commitments, and the work they’re accountable for.

AI is most useful when it helps leaders see what they need to see, while still honoring the responsibilities and accountabilities inside the company. The goal isn’t to give everyone the same view. It's to help each leader ask better questions from the right Seat, with human judgment still guiding the decisions.

What Ask Maz Helps Leadership Teams Do

Ask Maz is most useful when leaders bring it the questions they’re already carrying into planning, meetings, and weekly execution.

This isn’t just about finding information faster (though that matters). It’s about helping leaders interpret what they’re seeing, test assumptions, and prepare for better conversations before the team is sitting together trying to decide what comes next.

We're already hearing this from teams running on Ninety. They're using Ask Maz to analyze their Scorecards, strengthen Rocks, prepare for meetings, support Quarterly Planning, create issues, answer platform questions, and review accountability across teams.

Here are a few practical ways founders and leadership teams can put Ask Maz to use:

• Analyze the business without manual digging: Pull together what’s happening across Scorecards, Rocks, issues, and meeting history so you can get a clearer view of the business before the next leadership conversation.

• Monitor progress before surprises show up: See what’s on track, where follow-through needs support, and which conversations need to happen now.

• Detect patterns across teams: Identify recurring issues, emerging risks, ownership gaps, and opportunities that may be hard to see when each team is looking only at its own meetings, priorities, and metrics.

• Prepare for planning before the meeting starts: Review current Rocks, compare priorities to the vision, identify what needs attention, and suggest questions the leadership team should discuss at Quarterly or Annual Planning.

• Strengthen your Org Chart as the company grows: Review Seats, responsibilities, accountabilities, and reporting relationships so leaders can see where the current structure supports the work, where it may be getting in the way, and what updates may be needed as the company continues to grow.

• Move from insight to follow-through inside Ninety: Easily create To-Dos, issues, or Headlines from a conversation with Maz so the team can capture next steps while the thinking is still fresh.

Leaders are using Ask Maz to better understand where their business is today, bring more context into leadership conversations, and leave those conversations with clearer commitments.

One leader asked Maz for a company-wide view of how their teams were operating inside Ninety, and Maz turned activity across 37 teams and 159 active users into a useful leadership summary. Another leader asked Maz to assess Rock alignment across 13 teams and 89 Rocks before Quarterly Planning. A third asked Maz to audit a Finance Scorecard and discovered the team was tracking Sales and Marketing metrics instead of the financial and operational KPIs the Finance team truly owned.

Those are the kinds of questions founders, Integrators, and leadership teams have always needed to answer. Ask Maz helps them do it with more speed, more context, and a clearer view of the work that's already in motion.

AI Should Raise the Quality of Leadership

I don’t believe every founder or CEO needs to become an AI expert. But we should understand AI well enough to use it, challenge it, and guide it. We should know where it can help, where it needs review, and where human judgment must remain central.

That’s why I keep coming back to questions.

The quality of the questions we ask shapes the quality of our leadership conversations. Better questions increase the odds of seeing what deserves attention. Shallow questions, even with powerful tools, will only produce shallow answers.

Ask Maz gives leaders a better way to ask questions inside the context of their business.

A founder/CEO can ask, “Which Rocks are most at risk this quarter, and why?” An Integrator can ask, “Which issues keep coming back across leadership meetings?” A department leader can ask, “Does our Scorecard reflect the outcomes we actually own?” A coach can ask, “What should this leadership team discuss before its next quarterly session?”

Those questions aren’t just requests to gather information. They help leaders move from knowing more to leading better.

In a recent webinar, I shared a framework I like called: Crawl, Walk, Run, Fly. That’s how I’d encourage most companies to think about AI adoption. Don’t try to automate the entire organization at once. Don’t chase every new capability just because it exists. Start with one useful question, one recurring pain point, or one team that’s ready to learn.

Ask Maz gives you a practical starting place because it’s already connected to the operating data inside Ninety.

Start by asking it to help with your next leadership meeting. Ask it to review your Rocks before Quarterly Planning. Ask it to find gaps in a Scorecard. Ask it to help turn an unclear priority into a SMART Rock. Ask it to create an issue that will lead to the conversation your team needs to have. Then bring your judgment to the answer.

Remember, Ask Maz can help you and your leadership team see more, but your people still own the call. AI can support the thinking, but leadership still carries the responsibility for what happens next.

It's Still Early, But The Direction Is Clear

We’re already seeing Ask Maz change how teams prepare, make decisions, and execute. It’s helping teams ask questions, analyze Rocks and Scorecards, prepare for meetings, strengthen planning, create issues and To-Dos, and understand how different parts of their business connect.

As capable as Ask Maz already is, this is only the beginning of a much larger journey. With time, it will become even more useful, more connected, and more proactive in helping leadership teams run their business better.

I believe that, and I also believe the current version already points toward where leadership is going. The future of AI for business leaders isn’t about removing humans from our companies. It’s about helping us see across the business with more clarity. It's about giving us a better way to prepare, decide, and act. It's about using the systems we already trust to help us build companies that are more productive, humane, and resilient.

That’s why we built Ask Maz.

We built it for the founder/CEO preparing for Quarterly Planning who wants to understand which commitments need deeper review. We built it for the Integrator trying to connect Rocks, Scorecards, issues, and ownership before the next leadership meeting. We built it for the leadership team that wants to spend less time gathering context and more time making strong decisions.

Great companies aren’t built by accident. They’re built by leaders who ask better questions, strengthen their systems, and keep getting smarter about how work gets done. Ask Maz is just one more way we’re helping leadership teams do exactly that.

If you’re already running on Ninety, open Ask Maz before your next leadership conversation and bring it a question you’ve been carrying. And if you’re not on Ninety yet, take a look at what we’ve been building. Ask Maz is an early look at where we believe leadership is headed: better questions, better context, and people still at the center of the work.