On discovery, generosity & winning teams
For a while now, I have a ritual of writing down a handful of what I refer to as new year intentions over the holidays. Rather than hard goals or specific resolutions, these intentions are a bit more broad. They are essentially principles that motivate me to show up a certain way and guide my approach to my priorities in the new year.
In the last couple of years, I’ve gone a step further by sharing these intentions with my direct team & close colleagues. I’ve done this partly as inspiration, and partly as a way to hold me accountable too. It is always fun & insightful to learn when a specific intention resonates with someone, based on where they are in their journey and current headspace. This time around, one of my colleagues suggested that I share them even more broadly, in the form of a public essay here. After some hemming & hawing on my part, I settled on the observation that their good reasons to share publicly far outweighed my bad excuses not to! And, more importantly, it would be an early opportunity for me to live up to one of my intentions in 2025 - to connect with generosity.
So with that, here is a bit of a different essay for you, relative to the regular fare. My hope is that each of you finds at least one intent here that resonates, and can shape your approach too. Or better yet - they inspire you to come up with your own unique intentions that speak most to you.
1. Embrace discovery
We often refer to the idea of “being comfortable with ambiguity” as both a skill and a reflection of maturity as a product leader. In my experience, there are a few shades to this - from battling the anxiety that comes with the new or unfamiliar, to being willing to act in the face of imperfect/incomplete information, to being the one that creates clarity for others in the midst of chaos. The idea behind embracing discovery is to act purposefully & dutifully - and consistently - to learn & uncover what is true. Especially when what is in front of us is unknown, different, ambiguous or even scary.
Some examples for how we may embrace discovery…
Ensuring at least a subset of our strategy and goals are dedicated specifically towards learning something new.
Designing our team’s operating model to create space for newer, diverse and/or contrarian perspectives to shape product strategy & execution.
Embracing continuous discovery habits & methods to better understand the world of our users on an ongoing basis.
Experimenting with building and researching AI - as opposed to worrying it will replace you, or ignoring its rapid emergence.
2. Connect with generosity
As a PM or product leader, we are often the ‘hub’ for the many ‘spokes’ of cross-functional teammates, leaders, stakeholders, partner teams, etc. that make up our product org. We need these connections to ensure that product strategy is coherently aligned through the organization, and our collective actions are coordinated towards creating better product outcomes.
In establishing this connective tissue, it is often tempting to operate from a scarcity mindset, whether intentionally or not. Sometimes this comes in the form of us being selective in terms of our stakeholder engagement or the amount of information/context sharing. Or us approaching prioritization & resource allocation discussions with a zero-sum assumption. Or being territorial & defensive about the scope & surface areas that come under our purview.
The idea behind connecting with generosity is to choose a better way, and to operate instead from an abundance mindset. To build more bridges, to proactively think about ways you can be useful or helpful to others and to push on constraints that prevent you from doing so. Or to be creative about finding positive-sum outcomes in zero-sum games. And to seek to extend that generosity out as far as you can, beyond just your immediate proximity (ex: your direct team).
Some examples for how we may connect with generosity…
Find time with teams or colleagues in parts of the org that you don’t interface with regularly to share what you’re doing & why it matters. See if you can help with something that makes their jobs easier or more productive.
Approach prioritization or resourcing conversations with the goal to find ‘win-win’ decisions for everyone involved. Even if it takes some creativity to get there.
Create space and time for connecting with external peers, support & prop-up people in your network looking for new opportunities, or lean into mentoring and advising opportunities.
Write and share regularly. (Ok, I am biased about this one!)
The last intention here - broken out into two parts - speaks more to leading teams, not just myself individually. I encourage you to interpret “team” broadly as a group of folks with shared purpose or goals. Your relationships, families, communities, etc. can all be loosely seen as “teams” in this regard.
3. Winning teams…
…win one day at a time
If any of you are sports fans like me, you will undoubtedly have come across the concept of “building a winning habit”. The idea here is that championship teams don’t win the big games or big moments in games because they raise the level of their performance. It’s that (unlike most teams) they are most likely to perform at their normal levels in those times - because they are used to winning all moments, big or small. They benefit from having a muscle memory of winning, built up from the way they tackle all facets of their sport. They seek to win at everything - from fitness & conditioning, to training & practice, to game strategy & prep, to winning many smaller games and moments over time. This all builds and compounds internal confidence that shows up when it matters the most.
So, what would it mean to build a winning habit in our product work? To answer this requires us to decompose what we see as winning the big prize (ex: impact on our users and the business, gaining market share, hitting product goals, etc. ) into its constituent practices, rituals, intermediary milestones and requisite crafts that go into it. By doing so, it allows us to win at everything we do, and win “one day at a time”.
Some examples for how we may win one day at a time…
Making excellent product decisions, and building better judgement over time by reflecting on good & bad decisions you made in the past.
Winning by building intermediary capabilities or landing key milestones in our products and teams, ones that will be the foundation of bigger wins later.
Winning by sharing or getting tough feedback that raises the bar of our performance level on an ongoing basis. And having the hard convos with each other before they impact us in “big moments”.
Taking a course or investing time to develop a new skill that increases the odd of you succeeding in your craft.
…want it more
I believe that teams that care more, win more. And to care more about what matters to our users is hard, because it requires us to be more humble about ourselves (our goals, our personal successes, our favorite solutions..).
Winning teams & market leaders tend to either benefit from meaningful product differentiation (i.e. superior in how they solve valuable user problems) or distribution advantages (i.e. superior at meeting users where they are) - or some combination of the two (ex: network effects). These winning strategies require teams to operate with a depth of empathy, creativity and insight that is unique to them. And for them to then move fast & first in the direction that will set them apart from others. To me, this depth is only attainable if you have an insatiable, internal desire to be the best in the business. To see your goals and success metrics as purely stepping stones on an infinite journey to succeed in your ultimate mission. And to compete with yourself, not just your competition.
Some examples for how we may want it more…
Self-scout your strategy and tear-down your product regularly, looking for weaknesses to mitigate and gaps to fill. Envision ways that you might disrupt yourself, if you were an outsider.
Create space in your roadmap for concepts and solutions that are perhaps more exploratory or even risky - but have the potential for hard-to-measure and/or asymmetric upside for your users.
Understand the full ecosystem that your users exist in, to determine the best ways for your marketing and product to reach them and impact them.
If anything in particular here resonated for you, I’d love to hear. Feel free to shoot me a quick note at waqas.sheikh@gmail.com.
And if you know anyone who would benefit from my writings, I’d appreciate you sharing it with them using the button below! 🙏
For fun, and to embrace some discovery, I asked NotebookLM to make an audio discussion / overview of this essay. Check it out below!
Beyond consistency, one aspect of “winning one day at a time” that’s beneficial is more accurate goal setting.
When planning the future, it’s very easy to wildly overestimate what’s possible (or underestimate, although I see that less often with ambitious people and teams).
On a daily basis, though, it’s much easier to ask “how can I make today a win?” You know exactly what’s possible and can right size your daily goals for all sorts of external conditions.
Little wins every day stack up to big wins over time.