Chief of Staff
Chief of Staff
Chief of Staff
Ask Who, not How
Ask Who, not How
Ask Who, not How
16 February 2023
16 February 2023
16 February 2023


As far as childhoods go, I haven't had a typical one. Living in 1990s Nigeria meant being well cut off from the rest of the world, reachable only by letters that arrived, if at all, salt-stained and warped six months after they were posted. That also meant self-reliance was one of the first lessons I was ever taught. I was brought up to be independent, trust in my intuition, and generally figure things out for myself, by myself, before even thinking about asking for help.
For a long time, even up until a few years ago, this worked out for me. But there were times when being self-reliant was more of a hindrance than a blessing. It made me take the long route instead of the shortcut, even if the destination was the same and there was no penalty for cutting through the grass.
When I began transitioning from an IC to the Chief of Staff role, I realised the nature of both roles is to get things done. But that's where they diverge. An IC does it themselves. The CoS does it by guiding others, setting up the compass, and providing support exclusively through giving feedback and setting benchmarks.
It checks out, then, that in this strange no man's land, this liminal space, I began to flounder. I had grown too comfortable in my Zone of Excellence, which is writing. I had more on my plate than I could possibly handle on my own without letting a thing or ten fall through the cracks. I was running out of opportunities and needed to move along into my Zone of Genius: what I am uniquely good at, love to do and find sufficiently challenging. And I would need to do that by relying on others' Zones of Excellence.
Instead of asking 'How?', I'd need to ask 'Who'.
As a high achiever who wants to control what I can control (myself, usually), it's been hard to give up the How. I've found that this demands a higher level of vulnerability and trust. I'm accepting that someone else might be way better, smarter or faster at achieving a how than I would be, and then I'm trusting them to do it.
In many cases, asking How is slow and linear, because my time and efforts might be better utilised in a Zone of Genius task. I am not always the best person to finish a task, especially if the expected outcome is just to cross that finish line in whatever way works best. Asking Who, on the other hand, is exponential. Possibilities are no longer constrained by my potential alone — as long as I find the right who, the possibilities are endless.
All of this looks good on paper, but the simple truth took me many months to reconcile (months that were filled with self-doubt and imposter syndrome, naturally). I could hear the gears grating against each other, protesting when I tried to shift from How to Who. So what greased the system?
As far as childhoods go, I haven't had a typical one. Living in 1990s Nigeria meant being well cut off from the rest of the world, reachable only by letters that arrived, if at all, salt-stained and warped six months after they were posted. That also meant self-reliance was one of the first lessons I was ever taught. I was brought up to be independent, trust in my intuition, and generally figure things out for myself, by myself, before even thinking about asking for help.
For a long time, even up until a few years ago, this worked out for me. But there were times when being self-reliant was more of a hindrance than a blessing. It made me take the long route instead of the shortcut, even if the destination was the same and there was no penalty for cutting through the grass.
When I began transitioning from an IC to the Chief of Staff role, I realised the nature of both roles is to get things done. But that's where they diverge. An IC does it themselves. The CoS does it by guiding others, setting up the compass, and providing support exclusively through giving feedback and setting benchmarks.
It checks out, then, that in this strange no man's land, this liminal space, I began to flounder. I had grown too comfortable in my Zone of Excellence, which is writing. I had more on my plate than I could possibly handle on my own without letting a thing or ten fall through the cracks. I was running out of opportunities and needed to move along into my Zone of Genius: what I am uniquely good at, love to do and find sufficiently challenging. And I would need to do that by relying on others' Zones of Excellence.
Instead of asking 'How?', I'd need to ask 'Who'.
As a high achiever who wants to control what I can control (myself, usually), it's been hard to give up the How. I've found that this demands a higher level of vulnerability and trust. I'm accepting that someone else might be way better, smarter or faster at achieving a how than I would be, and then I'm trusting them to do it.
In many cases, asking How is slow and linear, because my time and efforts might be better utilised in a Zone of Genius task. I am not always the best person to finish a task, especially if the expected outcome is just to cross that finish line in whatever way works best. Asking Who, on the other hand, is exponential. Possibilities are no longer constrained by my potential alone — as long as I find the right who, the possibilities are endless.
All of this looks good on paper, but the simple truth took me many months to reconcile (months that were filled with self-doubt and imposter syndrome, naturally). I could hear the gears grating against each other, protesting when I tried to shift from How to Who. So what greased the system?
As far as childhoods go, I haven't had a typical one. Living in 1990s Nigeria meant being well cut off from the rest of the world, reachable only by letters that arrived, if at all, salt-stained and warped six months after they were posted. That also meant self-reliance was one of the first lessons I was ever taught. I was brought up to be independent, trust in my intuition, and generally figure things out for myself, by myself, before even thinking about asking for help.
For a long time, even up until a few years ago, this worked out for me. But there were times when being self-reliant was more of a hindrance than a blessing. It made me take the long route instead of the shortcut, even if the destination was the same and there was no penalty for cutting through the grass.
When I began transitioning from an IC to the Chief of Staff role, I realised the nature of both roles is to get things done. But that's where they diverge. An IC does it themselves. The CoS does it by guiding others, setting up the compass, and providing support exclusively through giving feedback and setting benchmarks.
It checks out, then, that in this strange no man's land, this liminal space, I began to flounder. I had grown too comfortable in my Zone of Excellence, which is writing. I had more on my plate than I could possibly handle on my own without letting a thing or ten fall through the cracks. I was running out of opportunities and needed to move along into my Zone of Genius: what I am uniquely good at, love to do and find sufficiently challenging. And I would need to do that by relying on others' Zones of Excellence.
Instead of asking 'How?', I'd need to ask 'Who'.
As a high achiever who wants to control what I can control (myself, usually), it's been hard to give up the How. I've found that this demands a higher level of vulnerability and trust. I'm accepting that someone else might be way better, smarter or faster at achieving a how than I would be, and then I'm trusting them to do it.
In many cases, asking How is slow and linear, because my time and efforts might be better utilised in a Zone of Genius task. I am not always the best person to finish a task, especially if the expected outcome is just to cross that finish line in whatever way works best. Asking Who, on the other hand, is exponential. Possibilities are no longer constrained by my potential alone — as long as I find the right who, the possibilities are endless.
All of this looks good on paper, but the simple truth took me many months to reconcile (months that were filled with self-doubt and imposter syndrome, naturally). I could hear the gears grating against each other, protesting when I tried to shift from How to Who. So what greased the system?
One drop of oil, if you will, was reframing the orientation of my commitment. As a creative IC in an experimental learning-driven role, I was more committed to the process than the outcome. It meant learning the ropes and familiarising myself with a new skill, which would then compound. But as Chief of Staff, I have to be committed to the outcome — and that means taking the shortest, most efficient route to it. More often than not, that involves asking who, not how.
"How do I increase our reach on Twitter?" leads to research, then experiments, then forming a strategy, then execution, then measurement. "Who can increase our reach on Twitter?" leads to a social media expert who can do all this in half the time I can and have double the results to show for it. And in the time they take to do that, I'd have directed the energy I've saved in the direction of things I'm uniquely good at.
I'll be the first to admit that I'm still not very good at cutting through the grass like this. It demands patience and constant reminders to myself (and from others) that it's okay—nay, important— to ask for help and admit that I don't have all the answers. But I hope there'll come a day when I can comfortably delegate everything I'm good at to people who are great at them, so I can be great at a couple of things, too.
One drop of oil, if you will, was reframing the orientation of my commitment. As a creative IC in an experimental learning-driven role, I was more committed to the process than the outcome. It meant learning the ropes and familiarising myself with a new skill, which would then compound. But as Chief of Staff, I have to be committed to the outcome — and that means taking the shortest, most efficient route to it. More often than not, that involves asking who, not how.
"How do I increase our reach on Twitter?" leads to research, then experiments, then forming a strategy, then execution, then measurement. "Who can increase our reach on Twitter?" leads to a social media expert who can do all this in half the time I can and have double the results to show for it. And in the time they take to do that, I'd have directed the energy I've saved in the direction of things I'm uniquely good at.
I'll be the first to admit that I'm still not very good at cutting through the grass like this. It demands patience and constant reminders to myself (and from others) that it's okay—nay, important— to ask for help and admit that I don't have all the answers. But I hope there'll come a day when I can comfortably delegate everything I'm good at to people who are great at them, so I can be great at a couple of things, too.
One drop of oil, if you will, was reframing the orientation of my commitment. As a creative IC in an experimental learning-driven role, I was more committed to the process than the outcome. It meant learning the ropes and familiarising myself with a new skill, which would then compound. But as Chief of Staff, I have to be committed to the outcome — and that means taking the shortest, most efficient route to it. More often than not, that involves asking who, not how.
"How do I increase our reach on Twitter?" leads to research, then experiments, then forming a strategy, then execution, then measurement. "Who can increase our reach on Twitter?" leads to a social media expert who can do all this in half the time I can and have double the results to show for it. And in the time they take to do that, I'd have directed the energy I've saved in the direction of things I'm uniquely good at.
I'll be the first to admit that I'm still not very good at cutting through the grass like this. It demands patience and constant reminders to myself (and from others) that it's okay—nay, important— to ask for help and admit that I don't have all the answers. But I hope there'll come a day when I can comfortably delegate everything I'm good at to people who are great at them, so I can be great at a couple of things, too.
Hat tip to Dhruv Saxena for using this phrase on me in one of our check-ins and sparking this entire process of reflection.
Another hat tip to Dan Sullivan and Dr Ben Hardy for writing Who Not How, the book that helped me shape my otherwise incoherent thoughts about Whos, Whys and Hows.
Hat tip to Dhruv Saxena for using this phrase on me in one of our check-ins and sparking this entire process of reflection.
Another hat tip to Dan Sullivan and Dr Ben Hardy for writing Who Not How, the book that helped me shape my otherwise incoherent thoughts about Whos, Whys and Hows.
Hat tip to Dhruv Saxena for using this phrase on me in one of our check-ins and sparking this entire process of reflection.
Another hat tip to Dan Sullivan and Dr Ben Hardy for writing Who Not How, the book that helped me shape my otherwise incoherent thoughts about Whos, Whys and Hows.
© Sindhu Shivaprasad 2022
© Sindhu Shivaprasad 2022
© Sindhu Shivaprasad 2022