Seeking perspective, through prospective hindsight
I start today’s post with a confession. In the past, I have struggled mightily with new year’s resolutions. Not so much the act of following through on them (though that can be a challenge, for sure!) - but in setting them in the first place. At least with any real conviction.
Over the years, I’ve oscillated in my rationalizations for why they never resonated for me the way they seem to for others, or what other personal failings on my part might be at play. With the benefit of reflection and hindsight, I’ve started to center around a primary explanation. In my observation, new year’s resolutions are often overly anchored on what happened - or didn’t - in the past, more so than what is possible in the future.
Whether it’s adopting a new workout regimen, reading more books, committing to traveling and relaxing more, connecting with friends & family, being more open to new experiences or change - much of the motivation behind these very reasonable and healthy aspirations lie in our sense of FOMO or past follies. We want to lose weight - because we let ourselves go over the holidays. We want to read more - because we’ve over-subscribed ourselves with work & ‘life’. We want to travel and relax more - because we’ve been stressed out recently, etc. Our new year’s resolutions are often just course-corrections or remediations with a different name.
The motivation for these resolutions is well-intentioned & genuine. And if acted upon, they will almost certainly lead us to reach better equilibrium states. But what they miss out on are openness to new opportunities and creative ideas that may present to us in the coming year. New possibilities and paths that are less tethered to what has happened prior, but perhaps more in tune with where we aspire to be in the future. To capture them, we need to be able to tap into the wisdom that comes with past experience & reflection - but with the proactivity that comes with thinking ahead. We need to tap into the concept of prospective hindsight.
Prospective hindsight, in our product work
Similar to how many us as individuals approach new year’s resolutions, I have observed many product teams operate with a well-intentioned, but incremental, approach to product development. An approach that is tethered to improving the current status quo more so than achieving a future, aspirational state. Thus their approach is also likely to be more reactive & limiting in nature.
A canonical example of this approach is the classic product or team retrospective - often using a stop-start-continue or highlights/lowlights/action items format. On the surface, there is nothing wrong with the idea of regular retrospectives - they are based in first principles of agile software development & continuous improvement. But on their own - while they may help you reach a better equilibrium point - retrospectives will not reveal to you the gamut of future possibilities and opportunities you might pursue. Tapping into the latter requires an approach that fosters prospective hindsight, and I believe there are a few common opportunities to do that in your product work:
Product Visioning: great products seek to meaningfully evolve, shift or disrupt the status quo for the better. Crafting and evangelizing a product vision is a key mechanism to crystallize that potential, and make your desired future impact feel real. A compelling product vision reimagines a better future state of your users, customers & business, and articulates how your product & ecosystem around it makes that future state possible. When done well, a product vision can inspire fresher “working backwards” thinking by your team. It can motivate new, creative strategies, decisions & changes to achieve that vision - ones that would not have emerged through incremental execution.
Goal Setting: effective product teams tend to approach goal-setting from both a ‘bottoms-up’ (i.e. what is achievable given our constraints, and evident in front of us?) and ‘top-down’ (i.e. what is bold in aspiration, and meaningful in impact?) perspective. I generally recommend unbundling those two perspectives during goal-setting, and approach them as two distinct exercises. For ‘top-down’ thinking, I’ve often found that asking your team a simple question like “what must be true for us by time X?” (where X is the last day of the time period being planned ex: December 31, 2024) can help unlock more clarity, creativity and impetus to remove limiting constraints.
Stakeholder Mapping: when an organization reaches a non-trivial size & complexity, access to functional expertise & diverse perspectives tends to become diffused through the org. Product teams run into frequent problems & thrash when they can’t anticipate the support and relationships needed with other teams and functions to be successful. This is especially true when you consider not just internal stakeholders, but external stakeholders that need to be involved as well over time. Proactive stakeholder mapping can help teams envision and design their future ‘network’ and ‘community’ before they become critical dependencies.
‘Pre-mortems’: while I am not a fan of the morbid undertones of the term, I have consistently found that conducting ‘pre-mortems’ for major product initiatives or other big changes (ex: a new strategy or large reorg) to be a clarifying & valuable endeavor. Pre-mortems can help you proactively identify preventable failure modes, risk areas & blind spots, and mitigate them well in advance. The original idea of the pre-mortem emerges directly from the prospective hindsight philosophy, and is explained well in this HBR article. Interestingly, in my experience, the “why has X failed?” framing that is typical in pre-mortems (an example of motivation through perspiration) often unlocks sharper thinking & creativity from participants than typical brainstorming exercises.
These are just a few examples of activities that you might lean into to foster prospective hindsight for your team, and reorient your execution towards a better future, not just a better present.
A footnote, on prospective hindsight for product leaders
Every activity mentioned above that can help us gain collective prospective hindsight - visioning, goal-setting, stakeholder mapping, pre-mortems - can also be simulated by you as an individual product leader.
As you enter the new year, it might be useful to conduct a personal thought exercise using similar prompts to what you may use with your teams:
Take a moment to ideate the vision you have for the kind of leader you wish to be for your team in the near and long term. What does that archetype look like, and how is the world around you better if you become that?
What goals do you seek to achieve & impact do you seek to manifest over the coming year? What must be true by December 31, 2024 - for you?
What do you want your network and community to look like in a year’s time? What edges and nodes of your personal social graph are most important to invest into and strengthen over the long-term?
As you ponder ‘success’ at a personal level over the next year - what risks do you foresee in achieving that, that you can mitigate ahead of time? And what blind spots might you be operating with that you can preemptively address, before they limit you?
Wishing you all a successful and fulfilling 2024! 🙏
I love your linking of prospective hindsight to the retrospective process.
Retrospectives are largely tactically focused – "how did the last sprint go?" – and over time can produce a never ending list of meaningless local optimizations
It's crucial to "look up" on a regular cadence to evaluate the strategic, shifting from the question of "how can we improve" to "what can we accomplish"?
The same is true for ourselves. We of course need a daily/weekly retrospective feedback loop. But a new year or other marker introduces an opportunity to evaluate what those feedback loops "mean". Not as a reaction to what's come before, but as an anticipation of what CAN come in the future, with the guidance of our learnings from the past.
David Hoang writes about a similar idea here: https://www.proofofconcept.pub/p/2024-intention "Great goals for the new year should be because you want to accomplish them, not out of obligation."