How do you CEO? / Rory San Miguel @ Propeller Aero
A learning journey of how startup CEOs work.
Over the past 6 six months, I've interviewed 10+ CEOs to learn how to do my job better.
It was one of the best things I’ve ever done for my own professional development and I hated the idea of keeping all the insights to myself. They all kindly agreed to share our candid conversations so that we can all learn from each other.
I’ll be posting the conversations every Monday and a summary of my own insights at the end of the series.
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#8 Rory San Miguel / CEO @ Propeller Aero
How do you CEO?
I do it through people by building great relationships and keeping connected with all parts of our team and our customers.
I prioritise getting to know people and will gladly pick up the phone to nut out a topic with someone 1on1, even if it's not the most efficient way to solve a problem.
I’m fairly organised.
It is really important as I work between Denver and Sydney and don’t have a co-founder anymore.
I don't miss much, I’m all over slack, email, lists and systems.
But I don’t have it all planned out and am bad at blocking out to get big things done.
I’m reactionary. This is one thing I’m working on and my calendar lately has looked a lot more open - and as a result, I'm starting to think about 2023 already and rehashing our vision.
During the day I’m all there for the team.
In the evenings, I’m there for the business doing deep work.
I err on the side of being fast-paced and hustle over stopping and making processes.
I surround myself with people to do things that I am not great at doing. We’ve just promoted Margaret into COO who is the complete opposite of me, an incredible, hyper-organised execution machine. I can focus on the what - Margaret will be focusing on the how.
I used to try to fix my weaknesses (and am still trying to a degree), but now I’m more about playing to my strengths instead.
Onboarding new leaders isn’t my favourite thing - I get impatient and just want to get back to building the business. This is another thing Margaret will own going forward :).
I prioritise talking to customers, even though at our scale others do that full time.
Because I often talk to customers, everyone knows that I deeply care about what we are building, and for who… and I really try to make sure I have enough context all the time to make the best decisions for the team, business and customers.
Unblocking the team is a key part of the role:
Customer success, sales and marketing challenges often get escalated to me as I am across our product, our customers' needs and propeller’s unique approach.
On the sales side, I get involved in roughly one deal every week.
And then I always enjoy diving into product brainstorming - but it’s more of a rare pleasure to get back to my roots rather than something more structural than that… the team is awesome.
How do you set strategy?
Not me, but WE set the strategy. Potential strategic directions are discussed during 1on1s which help me cover blind spots and make sure we’re pointing at the right thing. I’ll do some reading about other companies/blogs that have done similar things before and then bring it together in a document that then the leadership team will attack. This is the iterative process of achieving clarity and at some point, we’ll all be on the same page and go forward.
One of the most important bits (which I am really just starting to properly incorporate) is knowing what things we are actively deprioritising and having the composure to stick to our priorities despite on any given day many other directions popping up for consideration.
I do have a definition of strategy.
I wrote a strategy doc about projects at propeller so that we can use the same vocabulary.
I see the company as a restaurant.
It exists with the goal to feed people.
The ingredients are all the things we can use/do to solve the goal.
Strategy is the recipe we use, what’s the best way we can assemble what we have to hit the goal.
We have restaurant principles that always apply, like cleaning as you go and using fresh ingredients.
We can hypothesise what the best way is to hit the goal.
How do we know whether the recipe is good or bad? Our customers will tell us.
Figuring out what failure looks like and how to measure is a critical part of delivering on the goal.
Then we come up with what we need to do in 12 months and distil it to the next 6 months.
How do you communicate the strategy?
We have annual and biannual goals.
Often it starts with the question: what are 3-5 things we must accomplish this year?
I generally kick off the discussion with some ideas and we whittle the list down together.
Then we do a big brainstorm across the company.
Everyone participates in how we can hit the company goals.
We cluster solutions and how we can achieve them.
It is not democratic but everyone is heard.
How do you set goals?
We assemble cross-functional project teams that are responsible for resource allocation.
Each initiative has a project lead.
They take info as input, and figure out the goals.
They come up with the ingredients and recipe.
BAU is the remainder.
The goal is the objective.
The key result is a guide post, so the teams are more or less metric-driven.
The project teams are assembled and come back to the full team and present their approach.
The best project leads come up with a great strategy (aka choose a good recipe)
Then come back with high-quality reporting and project performance.
We have the projects as Google Slide to lay out all the projects.
They include the company goals and all initiatives.
I refer to that frequently.
The team will use that to ladder up to the goals.
We do weekly all-hands with updates.
We do a monthly demo day with deep dives.
The board pack itself the leadership team (and project leads) contribute.
As always, goals and processes around goals are a never-ending game of iteration and improvement and Margaret is bringing a tonne of energy and thought (and a track record) to this and will be revamping it all coming into 2023.
How do you communicate sensitive information?
Quit >> they send an email to their team.
Let go >> manager will send an email that the person is wrapping.
You always want to be clear from the start to avoid lots of conversations.
When leaders leave we usually talk to the team so it is not surprising and so we’re grounded in what we’re looking for in our next hire. I will send an email to the whole company.
We have a distributed leadership team - which doesn’t make it easy.
Margaret is going to be owning this going forward and we’re together going to be enhancing our relationships as well as starting to develop our 2023 plans and ideas which is really exciting.
The team are all experts in their field and I would say everyone is very autonomous day to day - so generally we are set up to manage issues by exception as I think it’s more efficient when you are so dispersed - with infrequent strategic check-ins (loosely timed around the 6-month planning cadence).