Getting Comfortable in the Problem
Getting Comfortable in the Problem
Getting Comfortable in the Problem
Share
Mistaking Motion for Progress
We've become very good at solving problems.
I'm not convinced we've become equally good at understanding them.
One of the things I've noticed over the years is that the more responsibility leaders take on, the more pressure they feel to have the answer.
I've felt that pressure myself.
In Product, people come to you because they need a decision. Engineering needs direction. Sales needs clarity. Customers want to know what you are going to do. Making decisions is part of the job, but it can become easy to measure your value by how quickly you make them.
For a long time, momentum felt like progress to me. If we left a meeting with a decision, I assumed we had used the time well.
Over time, I began to notice that reaching an answer and understanding the problem were not always the same thing.
Some of the weakest decisions I've been part of did not happen because the people involved lacked experience or good judgment. They did not happen because anyone cared less about the outcome.
They happened because we thought we understood the problem before we actually did.
We had accepted the way it was first presented and moved straight into discussing what to do about it. The conversation felt productive because it was moving forward, but it was often moving forward at the surface level of the problem.
“The problem someone brings into a conversation is very rarely the full problem they are trying to solve. More often, they are describing it through the solution they have already imagined.”
Mistaking Motion for Progress
We've become very good at solving problems.
I'm not convinced we've become equally good at understanding them.
One of the things I've noticed over the years is that the more responsibility leaders take on, the more pressure they feel to have the answer.
I've felt that pressure myself.
In Product, people come to you because they need a decision. Engineering needs direction. Sales needs clarity. Customers want to know what you are going to do. Making decisions is part of the job, but it can become easy to measure your value by how quickly you make them.
For a long time, momentum felt like progress to me. If we left a meeting with a decision, I assumed we had used the time well.
Over time, I began to notice that reaching an answer and understanding the problem were not always the same thing.
Some of the weakest decisions I've been part of did not happen because the people involved lacked experience or good judgment. They did not happen because anyone cared less about the outcome.
They happened because we thought we understood the problem before we actually did.
We had accepted the way it was first presented and moved straight into discussing what to do about it. The conversation felt productive because it was moving forward, but it was often moving forward at the surface level of the problem.
“The problem someone brings into a conversation is very rarely the full problem they are trying to solve. More often, they are describing it through the solution they have already imagined.”
Mistaking Motion for Progress
We've become very good at solving problems.
I'm not convinced we've become equally good at understanding them.
One of the things I've noticed over the years is that the more responsibility leaders take on, the more pressure they feel to have the answer.
I've felt that pressure myself.
In Product, people come to you because they need a decision. Engineering needs direction. Sales needs clarity. Customers want to know what you are going to do. Making decisions is part of the job, but it can become easy to measure your value by how quickly you make them.
For a long time, momentum felt like progress to me. If we left a meeting with a decision, I assumed we had used the time well.
Over time, I began to notice that reaching an answer and understanding the problem were not always the same thing.
Some of the weakest decisions I've been part of did not happen because the people involved lacked experience or good judgment. They did not happen because anyone cared less about the outcome.
They happened because we thought we understood the problem before we actually did.
We had accepted the way it was first presented and moved straight into discussing what to do about it. The conversation felt productive because it was moving forward, but it was often moving forward at the surface level of the problem.
“The problem someone brings into a conversation is very rarely the full problem they are trying to solve. More often, they are describing it through the solution they have already imagined.”
Solutions Are Easier to Describe Than Problems
That distinction matters more than I understood earlier in my career.
The problem someone brings into a conversation is very rarely the full problem they are trying to solve. More often, they are describing it through the solution they have already imagined.
They ask for a feature, a report, or a new process. That may turn out to be exactly what is needed. But it may also be the first interpretation of a problem that has not yet been fully understood.
I don't think that happens because people are careless. It happens because solutions are easier to describe than problems. A solution gives the conversation shape. It gives everyone something tangible to respond to. It creates a sense that progress has already begun.
The problem itself is usually less tidy.
Solutions Are Easier to Describe Than Problems
That distinction matters more than I understood earlier in my career.
The problem someone brings into a conversation is very rarely the full problem they are trying to solve. More often, they are describing it through the solution they have already imagined.
They ask for a feature, a report, or a new process. That may turn out to be exactly what is needed. But it may also be the first interpretation of a problem that has not yet been fully understood.
I don't think that happens because people are careless. It happens because solutions are easier to describe than problems. A solution gives the conversation shape. It gives everyone something tangible to respond to. It creates a sense that progress has already begun.
The problem itself is usually less tidy.
The Discipline of Digging Deeper
Today, when someone brings me a request, I spend more time asking about the use case.
What are they trying to achieve?
What is getting in the way?
Why does it matter now?
What would actually change if we solved it?
Then I keep digging.
Not because I assume the first answer is wrong. It is usually based on a real need and given with the best intentions. I keep digging because experience has taught me that it is rarely the whole story.
Sometimes the functionality already exists, and the real problem is awareness or adoption. Sometimes the proposed solution would address one part of the issue while leaving the underlying workflow untouched. Sometimes the conversation uncovers product work that is far more important than the original request suggested.
The first request is not necessarily wrong. It is simply where the conversation begins.
“I used to place more value on being able to move people towards an answer. Now I place far more value on facilitating the conversation that helps us understand what we are actually trying to solve.”
The Discipline of Digging Deeper
Today, when someone brings me a request, I spend more time asking about the use case.
What are they trying to achieve?
What is getting in the way?
Why does it matter now?
What would actually change if we solved it?
Then I keep digging.
Not because I assume the first answer is wrong. It is usually based on a real need and given with the best intentions. I keep digging because experience has taught me that it is rarely the whole story.
Sometimes the functionality already exists, and the real problem is awareness or adoption. Sometimes the proposed solution would address one part of the issue while leaving the underlying workflow untouched. Sometimes the conversation uncovers product work that is far more important than the original request suggested.
The first request is not necessarily wrong. It is simply where the conversation begins.
“I used to place more value on being able to move people towards an answer. Now I place far more value on facilitating the conversation that helps us understand what we are actually trying to solve.”
The Discipline of Digging Deeper
Today, when someone brings me a request, I spend more time asking about the use case.
What are they trying to achieve?
What is getting in the way?
Why does it matter now?
What would actually change if we solved it?
Then I keep digging.
Not because I assume the first answer is wrong. It is usually based on a real need and given with the best intentions. I keep digging because experience has taught me that it is rarely the whole story.
Sometimes the functionality already exists, and the real problem is awareness or adoption. Sometimes the proposed solution would address one part of the issue while leaving the underlying workflow untouched. Sometimes the conversation uncovers product work that is far more important than the original request suggested.
The first request is not necessarily wrong. It is simply where the conversation begins.
“I used to place more value on being able to move people towards an answer. Now I place far more value on facilitating the conversation that helps us understand what we are actually trying to solve.”
Redefining What Leadership Means
That has changed the way I think about leadership.
I used to place more value on being able to move people towards an answer. Now I place far more value on facilitating the conversation that helps us understand what we are actually trying to solve.
That requires conversations where people can question the framing instead of immediately defending a solution. Where different perspectives are brought into the room before the direction feels fixed. Where curiosity is allowed to last a little longer than certainty.
I've learnt that staying in the problem is not delaying the decision.
It is improving the decision.
Redefining What Leadership Means
That has changed the way I think about leadership.
I used to place more value on being able to move people towards an answer. Now I place far more value on facilitating the conversation that helps us understand what we are actually trying to solve.
That requires conversations where people can question the framing instead of immediately defending a solution. Where different perspectives are brought into the room before the direction feels fixed. Where curiosity is allowed to last a little longer than certainty.
I've learnt that staying in the problem is not delaying the decision.
It is improving the decision.
The Uncomfortable Cost of Certainty
Sometimes that means staying in the problem space a little longer, even when people are waiting for direction, and the pressure to move is real.
That can be uncomfortable, particularly for leaders. Responsibility creates an expectation of certainty. People look to you for confidence, and it can feel as though leaving a meeting without an answer means you have failed to provide it.
I don't believe that anymore.
Sometimes the most responsible thing a leader can do is admit that the answer is not clear yet.
That does not mean avoiding decisions or allowing conversations to continue indefinitely. It means recognizing when the room is debating solutions without sharing the same understanding of the problem.
I sometimes wonder if we have become uncomfortable with that uncertainty.
We celebrate speed. Fast decisions. Rapid delivery. Shorter cycles.
Those things matter. I still believe they matter.
But speed does not create understanding. It simply amplifies whatever understanding already exists.
If we have understood the problem deeply, speed becomes an incredible advantage. Teams can move with confidence because the direction is clear and the trade-offs make sense.
If we have not, speed only helps us commit more quickly. We can build well, deliver on time, and still find ourselves back in the same conversation months later.
We simply arrive at the wrong destination faster.
“A poorly understood problem can consume months of work from capable people. Strong execution cannot compensate for weak understanding. It can only make the consequences more expensive.”
The Uncomfortable Cost of Certainty
Sometimes that means staying in the problem space a little longer, even when people are waiting for direction, and the pressure to move is real.
That can be uncomfortable, particularly for leaders. Responsibility creates an expectation of certainty. People look to you for confidence, and it can feel as though leaving a meeting without an answer means you have failed to provide it.
I don't believe that anymore.
Sometimes the most responsible thing a leader can do is admit that the answer is not clear yet.
That does not mean avoiding decisions or allowing conversations to continue indefinitely. It means recognizing when the room is debating solutions without sharing the same understanding of the problem.
I sometimes wonder if we have become uncomfortable with that uncertainty.
We celebrate speed. Fast decisions. Rapid delivery. Shorter cycles.
Those things matter. I still believe they matter.
But speed does not create understanding. It simply amplifies whatever understanding already exists.
If we have understood the problem deeply, speed becomes an incredible advantage. Teams can move with confidence because the direction is clear and the trade-offs make sense.
If we have not, speed only helps us commit more quickly. We can build well, deliver on time, and still find ourselves back in the same conversation months later.
We simply arrive at the wrong destination faster.
“A poorly understood problem can consume months of work from capable people. Strong execution cannot compensate for weak understanding. It can only make the consequences more expensive.”
The Uncomfortable Cost of Certainty
Sometimes that means staying in the problem space a little longer, even when people are waiting for direction, and the pressure to move is real.
That can be uncomfortable, particularly for leaders. Responsibility creates an expectation of certainty. People look to you for confidence, and it can feel as though leaving a meeting without an answer means you have failed to provide it.
I don't believe that anymore.
Sometimes the most responsible thing a leader can do is admit that the answer is not clear yet.
That does not mean avoiding decisions or allowing conversations to continue indefinitely. It means recognizing when the room is debating solutions without sharing the same understanding of the problem.
I sometimes wonder if we have become uncomfortable with that uncertainty.
We celebrate speed. Fast decisions. Rapid delivery. Shorter cycles.
Those things matter. I still believe they matter.
But speed does not create understanding. It simply amplifies whatever understanding already exists.
If we have understood the problem deeply, speed becomes an incredible advantage. Teams can move with confidence because the direction is clear and the trade-offs make sense.
If we have not, speed only helps us commit more quickly. We can build well, deliver on time, and still find ourselves back in the same conversation months later.
We simply arrive at the wrong destination faster.
“A poorly understood problem can consume months of work from capable people. Strong execution cannot compensate for weak understanding. It can only make the consequences more expensive.”
Understanding Is the Real Multiplier
That is where the stakes become much larger than a single product decision. Leaders shape more than the decisions an organization makes. We also shape which problems people spend their time and energy trying to solve.
A poorly understood problem can consume months of work from capable people. Strong execution cannot compensate for weak understanding. It can only make the consequences more expensive.
The biggest shift in my leadership was not learning how to make better decisions.
It was learning that better decisions usually begin with better conversations.
The longer I lead teams, the less I think my responsibility is to be the first person in the room with the answer. More often, it is to help the room stay curious, challenge the assumptions underneath the request, and understand the problem well enough that the right answer becomes clearer.
That work can look slower at first.
In my experience, it is usually what allows the team to move with real speed later.
The quality of our solutions is almost always limited by the quality of our understanding.
Understanding Is the Real Multiplier
That is where the stakes become much larger than a single product decision. Leaders shape more than the decisions an organization makes. We also shape which problems people spend their time and energy trying to solve.
A poorly understood problem can consume months of work from capable people. Strong execution cannot compensate for weak understanding. It can only make the consequences more expensive.
The biggest shift in my leadership was not learning how to make better decisions.
It was learning that better decisions usually begin with better conversations.
The longer I lead teams, the less I think my responsibility is to be the first person in the room with the answer. More often, it is to help the room stay curious, challenge the assumptions underneath the request, and understand the problem well enough that the right answer becomes clearer.
That work can look slower at first.
In my experience, it is usually what allows the team to move with real speed later.
The quality of our solutions is almost always limited by the quality of our understanding.
Leadership
Load More
Load More