An Eigenquestion for leaders, to help widen your aperture

"What is something I should know, to help me be a better leader, for us?"

Over the past few months, I have been reflecting on the nuances behind effective change management, and the concept of organizations as complex systems. It turns out I am not alone in this. Many product leaders that I speak with these days are also operating in environments undergoing rapid change - and are trying to figure out how best to lead their teams through that.

Change of course comes in many forms - opportunistic vs. challenging, intentional vs. induced or forced, local vs. global. Nowadays, you may be shaping your product strategy & portfolio to optimize for new growth & profitability guardrails, exploring creative new possibilities to serve your users through the power of generative AI & LLMs, navigating a tricky personal or personnel conflict or stabilizing and galvanizing a team after a difficult round of layoffs. Change runs the gamut. And the ability to effectively and empathetically lead others through change can be seen as an essential leadership skill.

Meanwhile, even in a stable state, leading an organization of any meaningful size, scope & heterogeneity is a complex job. A central premise and promise of organizations are that the whole (in terms of value created) is greater than the sum of its individual parts & interactions. But that premise introduces an implicit constraint - if your aperture is limited to a few parts, it’s challenging to perceive & comprehend the whole value being created. Furthermore, as organizations evolve in terms of size, scope or heterogeneity - their complexity grows, but your aperture as an individual leader may not.

There is an important implication of all this for leaders: if you wish to drive an impactful change through a complex organization, you need to widen your aperture. This is necessary for a few reasons:

• To inform and influence the change widely through the organization.

• To understand the ground realities, constraints & tradeoffs that make change hard to implement.

• To evaluate if the change is resonating or not.

• To validate that the change is having its desired impact, or surfacing the need to course-correct.

In general, every organization has some set of structured rhythms & systems for its steady-state operations. But in times of major or rapid change, these standard operating procedures (SOPs) can be inefficient or lack the context & nuance needed for leaders and teams to converge well. Change management goes beyond just one-way communication or reporting back. Instead, to lead an organization through impactful change, you must design rich, diverse & high-bandwidth feedback loops between you and your teams.

You need to widen your aperture.

An Eigenquestion, to help widen your aperture

“What is something I should know, to help me be a better leader, for us?”

A few months ago, I asked this question in a 1:1 with a key cross-functional team-member. This is someone who works very closely as a peer to many folks on my team, across multiple important priorities. And also someone who I am fortunate to have a high-trust relationship with. It was one of those rare 1:1s where we were bereft of a typical meeting agenda chock-full of execution, team and block-and-tackle topics.

I will leave it to your imagination as to whether this question came from a moment of creative inspiration, or a sense of temporary desperation to fill our time :) Nonetheless, this simple prompt ended up sparking - by far - our richest & deepest 1:1 ever. We blew through our normal 30 minutes, and went into depth on a variety of topics relating to product vision & strategy, challenges in our team & organizational dynamics and constructive feedback to help us deepen our working relationship in the future. Coming out of it, we both felt energized and impressed that we’d covered a surface area so vast that it would’ve taken us multiple months of 1:1s to get into otherwise. We had both widened our apertures.

Reflecting back on that session, I felt the prompt was useful for a few reasons:

1. It invited candor and vulnerability: it’s not always easy to share candid feedback (and critique) directly with a leader - but it is far easier to do so when one is invited to do so, and knows that the leader in question is genuinely curious. By reinforcing the “us” in the equation, it lowered the barrier-to-entry for a more honest conversation. And it helped to break the invisible 4th wall that can exist in such relationships, even if unintentional.

2. It reinforced how essential ‘ground truth’ is: as a leader, it’s worth frequently reminding yourself and others around you that “you don’t know what you don’t know”. Your ability to lead effectively and have sound judgement relies on having rich, accurate context from your teams. Being self-aware, humble and transparent about this information asymmetry can help unlock more fluid, natural context-sharing from your teams.

3. It allowed us to go deeper than our typical SOPs: in this example, it is likely that our standard operating procedures for strategy, execution, etc. would have surfaced many of the challenges that we discussed 1:1 - but at a surface level. Instead we were able to diagnose the symptoms deeper, identify broader patterns & themes for us to address, and holistically understand the impact of these challenges. I exited the session with more empathy for my partner, and they exited with more understanding of the tradeoffs and constraints our teams were working under.

Scaling up, and out

Since that 1:1, I have experimented with a few variations of that question in other touch-points with my team-members, partners and stakeholders. Over time, as we have navigated a variety of big changes together, I’ve found the feedback loops that this question unlocks to be essential to my leadership approach and judgement. For me, it has acted as a form of Eigenquestion (h/t

Shishir Mehrotra

) - a question that rapidly cuts to the core of what I need to understand, assess and act upon. And a mechanism for creating a collective consciousness with my teams to work through strategies, opportunities and problems together.

If you are in a similar position as a leader - I recommend making it a priority to design your own rich, diverse & high-bandwidth feedback loops with your teams. You can start doing this by:

1. Experimenting with your own form of an Eigenquestion such as the one above in your next set of 1:1s, beginning with those folks that you have high-trust relationships with.

2. Evaluating if the touch-points you have with your team and other partners are sufficiently rich and go beyond the surface level. Are you getting the depth of context and feedback you really need? If not, you might be able to improve that with fairly subtle tweaks.

3. Mapping out the relationships that you have today with your team, leadership, partners and other stakeholders. Determine if you have enough coverage and heterogenous connections in place to effectively widen your aperture.