Oscar Howie's Quick takes

“Chief of Staff” models from a long-time Chief of Staff

I have served in Chief of Staff or CoS-like roles to three leaders of CEA (Zach, Ben and Max), and before joining CEA I was CoS to a member of the UK House of Lords. I wrote up some quick notes on how I think about such roles for some colleagues, and one of them suggested they might be useful to other Forum readers. So here you go:

Chief of Staff means many things to different people in different contexts, but the core of it in my mind is that many executive roles are too big to be done by one person (even allowing for a wider Executive or Leadership team, delegation to department leads, etc). Having (some parts of) the role split/shared between the principal and at least one other person increases the capacity and continuity of the exec function.

Broadly, I think of there being two ways to divide up these responsibilities (using CEO and CoS as stand-ins, but the same applies to other principal/deputy duos regardless of titles):

1. Split the CEO's role into component parts and assign responsibility for each part to CEO or CoS
   1. Example: CEO does fundraising; CoS does budgets
   2. Advantages: focus, accountability
2. Share the CEO's role with both CEO and CoS actively involved in each component part
   1. Example: CEO speaks to funders based on materials prepared by CoS; CEO assigns team budget allocations which are implemented by CoS
   2. Advantages: flex capacity, gatekeeping

Some things to note about these approaches:

• In practice, it’s inevitably some combination of the two, but I think it’s really important to be intentional and explicit about what’s being split and what’s being shared
  • Failure to do this causes confusion, dropped balls, and duplication of effort
  • Sharing is especially valuable during the early phases of your collaboration because it facilitates context-swapping and model-building
  • I don’t think you’d ever want to get all the way or too far towards split, because then you functionally have one more department-lead-equivalent, and you lose a lot of the benefits in terms of flex capacity and especially continuity
• Both approaches depend on trust, and maximising them depends on an unusually high degree of trust
  • CEO trusting CoS to act on their behalf
    • In turn, this depends on trusting their judgement, and in particular trusting their judgement of when it’s appropriate to act unilaterally and when it’s appropriate to get input/approval from CEO
  • Others trusting that CoS is empowered to and capable of acting on CEO’s behalf
    • Doesn’t work if CEO and CoS disagree or undermine each other’s decisions in view of others, or if others expect CoS decisions to be overturned by CEO
    • It being easier to burn credibility than to build it is something close to an iron law, which means CoS should tread carefully while establishing the bounds of their delegated authority
• It’s not a seniority thing: an Executive Assistant having responsibility for scheduling is an example of splitting the role; a Managing Director doing copyedits for the CEO’s op-ed is an example of sharing the role
• I don’t think the title “CoS” matters, but I do think maximising the benefits of both models requires the deputy to have a title that conveys that they both represent and can act unilaterally on behalf of the principal to some meaningful degree
  • Managing Director and Chief of Staff do this; Project Manager and Exec Assistant do not

1. Healthy habits can be good for your wellbeing and productivity, in the short- and long-term
2. Establishing healthy habits is especially hard under conditions of scarcity: time, energy, bandwidth
3. It’s worth putting in effort to establish health habits during the good times

I keep daily yoga and meditation practices, one in the morning and one during the day, and I keep them during busy and stressful periods. I don’t think I would have started or maintained either (or habits related to sleep, food, phone) if I hadn’t entrenched them as fixtures of my routine when I was living an easier life.

This is not an argument for specific habits. Compiling the evidence behind and my experience of my preferred habits would require more scarce time than I currently have. And in any case, I don’t think I’ve found the Correct Combination for myself, let alone anybody else.

It is an argument for acting now, beginning to solidify whatever your preferred habits might be, before you come to really depend on them.