Excellence in Action

The Crucial Role of Product Leaders with Matt Kaplan

Insights and perspectives for product leaders from expert Chief Product Officer Matt Kaplan

One of the most challenging aspects of being a product leader is bringing clarity to our organization while operating in a constant state of extreme uncertainty. Nearly every day, we navigate ambiguity to find product-market fit, discover new customer needs, and adapt to changing technologies, macro conditions, and competitive threats.

As product leaders, we’re naturally comfortable with uncertainty; it is our one true constant, and the endless possibility that it creates is actually our happy place. Yet, the rest of our organization craves the exact opposite: certainty. They want to know what’s on the roadmap, when products will ship, how customers will react, and the payback for every product investment.

In this article, I’ll share some proven strategies for resolving this tension and bringing greater clarity to your organization while maintaining your intellectual integrity. Having worked in both early and late-stage product-led companies, I’ve learned that our greatest strengths as product leaders are:

1) Acting on intuition: making decisions with limited data

2) Adaptability: a willingness to change when new data is presented

We draw on deep personal experiences and observations of the world around us to adapt to the challenges and uncertainties of the moment. While we do this innately and coach our teams to embrace this as well, within a company, we don’t operate in isolation. A critical aspect of our role as product leaders is bringing the entire organization along our journey from obscurity to clarity and helping them to navigate uncertainty as well.

This was no more apparent than during the pandemic when the world as we knew it had literally changed overnight. At Toast, our mission was always to enable the restaurant community to thrive, but during the pandemic, that focus shifted to helping restaurants survive.

In March 2020, we ripped up our newly minted roadmap and focused on the only thing that mattered—keeping restaurant doors open. We quickly launched a stand-alone online ordering service, accelerated the launch of a low-cost delivery product, promoted the sale of gift cards to help with cash flow, and automated the application process for SBA loans. Heading into the year, none of these capabilities were on our near-term roadmap, but they were all critical to helping restaurants stay open for business. We pivoted quickly, and for good reason—our customers were in dire need of help, and everyone at Toast hopped on board.

Our experience during the pandemic was a good example of seeking certainty amidst ambiguity, clarity amidst confusion, and focus amidst constant (and worrying) distractions. It can be more challenging to achieve that level of clarity during “normal” periods of uncertainty—not extreme uncertainty. Without an urgent need to act, there’s more time to reflect, analyze, debate, and wallow in ambiguity.

Despite operating within a constant state of change, product leaders are expected to establish a well-defined product strategy and vision, build a comprehensive plan and roadmap, motivate and lead a high-functioning team, and deliver successful products (on time) that customers love, and that drive meaningful impact to the business.

In essence, a key part of a product leader’s job is to bring clarity and certainty to the rest of the organization who need it. Think back to the many clarity-defining questions you’ve likely been asked by your peers. Do any of these sound familiar?

  • Chief Technology Officer: What are your criteria for prioritizing initiatives?
  • Chief Marketing Officer: What is the short-term roadmap, and when are we shipping?
  • Chief Financial Officer: What is the ROI for each product investment?
  • Chief Customer Officer: How do you plan to raise customer NPS?
  • Chief People Officer: How will you measure and improve the performance of your team?

The answers to many of these questions are imprecise at best. The truth is, we’re never really sure when the roadmap will need to change, what the exact return on investment will be, or what will move the needle on customer NPS.

As product leaders, we’re comfortable operating in shades of gray, although our peers often feel otherwise. To product leaders, uncertainty signals an opportunity to be explored and exploited. However, for other parts of the organization, it gets in the way of doing their jobs. They crave clarity, and answering these questions helps them do their jobs more effectively. 

Often, one potential reaction I’ve seen from product leaders (me included) is to avoid answering these questions for as long as possible. We defensively ask, “Why do they need this information? Don’t they know that roadmaps are out of date the minute they’re published? Don’t they understand how hard it is to quantify the impact? Why can’t we just be trusted to do our jobs?” This is not a great strategy as it ignores the fundamental needs of your peers and likely your boss. As my CEO Bob once told me, the roadmap is the “heartbeat of the organization,” so it’s our job to keep the beat strong and steady to the best of our ability, despite the occasional arrhythmia that we may cause due to changes.

An alternate approach is to be highly transparent and answer these questions with great detail, knowing full well that there’s an incredible amount of false precision in what we say and do. But I’ve seen how inviting other functional leaders into our fuzzy world can backfire due to a lack of context or their inability to operate well with any sort of ambiguity.

In fact, it makes some people extremely uncomfortable. This may lead to the demand for more research, experimentation, a second opinion, and fact-checking—a stone-cold killer of rapid innovation.

Either way, your reaction to your peers may make them less confident in you and your intuition-based leadership style.

You may begin to doubt yourself, your team, and even your career choice. This can feel overwhelming at times and, in extreme cases, can lead to imposter syndrome.

My advice? Don’t let it.

Remember your superpower of acting on intuition and your ability to rapidly adapt to change even though others may not like or appreciate it. You’re in the product leadership role because you have the skills to turn vague ideas into new realities with limited information, like taking an impressionist painting and bringing it to life in full HD resolution before AI even existed. 

So, how might you harness your superpower to address the needs of your peers and create the “heartbeat” needed by the organization? How might you build their confidence in you as a well-informed and polished leader who does more than just “go with their gut?”

Here are five strategies that I’ve found to be effective at navigating through ambiguity and bringing greater clarity to organizations while increasing confidence in you and your team:

Get closer to customers and their problems:

The voices of our customers are powerful antidotes to fear and uncertainty. We can quell doubts about ourselves and others by actively listening to customer feedback. There’s nothing more powerful than saying, “I spoke with 10 customers, 8 of whom told me this is a real problem.” Of course, there are always the contrarians who quote Henry Ford and customers who just want faster horses, but if you stay focused on their problems and not solutions, you’ll likely avoid this debate.

To prevent analysis paralysis, you can stop when the conversations become overly repetitive and you fail to learn new things. In a startup or early-stage product, you’ll need to talk to prospective customers daily. In a larger company, you’ll have more resources to invest in programmatic listening posts, including a UX research team, voice of customer program, or customer advisory board.

Shift focus toward product strategy and outcomes:

Everyone knows product roadmaps are impossible to remember and always changing, so instead, focus the organization on a durable product strategy and higher-level themes that drive clear business outcomes. A well-articulated product strategy is an opinionated story of how your product vision solves your customer’s most difficult problems, albeit missing many details that will get filled in over time. It’s a clear and compelling narrative that’s memorable and motivating to customers, employees, and investors alike.

And most importantly, it’s your story, so you can imagine it as you wish. When filling in the details, stick to a more thematic roadmap that outlines the “big rocks” and major outcomes you’ll drive rather than the features you’ll ship. This provides the team with clear goals but preserves flexibility to alter exactly how they accomplish them. A good thematic roadmap lists a few outcome-oriented objectives like “Double the adoption rate,” “Reduce onboarding time by 30%”, or “Lower tickets per customer by 10%.”

Enlist your peers and model your bets:

As a product leader, you’re naturally comfortable with the unknown, but remember, not everyone is, so you need to be empathetic. When socializing your ideas with others, help them by separating facts––what you know, from assumptions––what you believe. By calling these initiatives “bets,” you acknowledge there is uncertainty at play and open the door to failure, as not all bets will pay off.

Develop and share the model you will use to evaluate each bet and the criteria for declaring success. This structured and methodical approach to validating your assumptions will be appreciated and understood by your peers, leading to greater credibility and trust.

Make progress and learnings visible:

My old boss, Andrew, would say he likes to “drive by the construction site and hear the sound of hammering,” so he feels the work getting done. You must manufacture that feeling in software since it’s hard to see visible progress (especially with remote work). One good way is to create a bi-weekly show-and-tell forum to demo features and celebrate wins, but be sure to avoid “success theater,” where everything is claimed as a win, no matter how small or insignificant the result.

It’s equally important to share what you learned when you failed to hit the stated goals and how you plan to adapt your approach going forward. Sharing progress transparently with the broader organization boosts team morale and reinforces your credibility as a capable leader. Inviting the whole company to a monthly product showcase will bring the product strategy to life and excite everyone about what’s coming next. It’s also a great way to gather internal feedback and recruit other employees passionate about a product career.

Don’t invent everything; learn from others:

Solving customer needs and building great products is difficult enough; there’s no need to introduce more uncertainty by inventing new methods or unproven techniques. It’s best to save time and energy innovating on things that matter to your customers. As a result, look to well-established approaches to formulating strategy, prioritizing initiatives, and organizing teams.

Create a learning culture by sharing related books, blogs, podcasts, and articles with your team on an ongoing basis. You can establish greater credibility with your peers by referencing these proven frameworks, but use this technique sparingly as you could appear at times to be “too academic.” Seek guidance and support from others who have dealt with similar problems and situations. Better yet, consider forming a network of trusted advisors who can provide valuable perspectives and help you address key challenges more confidently. 


Successful product leadership requires a strong sense of curiosity and empathy, resilience in the face of adversity, and a knack for embracing ambiguity. Remember that while acting on intuition and being adaptable are your greatest assets, your company's success will ultimately depend on your ability to bring the rest of the organization along for the ride.

Special thanks to John Cutler and Craig Daniel for their contributions to this piece! 

Matt Kaplan

Chief Product Officer

May 2024

The information presented in this post is for illustrative purposes only and is not an offer to sell or the solicitation of an offer to purchase an interest in any private fund managed or sponsored by Tidemark or any of the securities of any company discussed. Tidemark portfolio companies identified above are not necessarily representative of all Tidemark investments, and no assumption should be made that the investments identified were or will be profitable. For additional important disclaimers regarding this post, please see “ Purpose of the Site; Not Investment Advice; No Recommendations” and “Regulatory Disclosures” in the Terms of Use for Tidemark’s website, available at Terms of Use (tidemarkcap.com).

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