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How do you CEO? / Duncan Anderson @ Edrolo
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.
If you want to come along the CEO journey - hit subscribe 💥
#11 Duncan Anderson / Co-CEO @ Edrolo
How do you CEO?
Ben, Jeremy and I split the job.
“If you are pointed in the right direction then it doesn’t matter how slow you are going you are making progress. If you are pointed in the wrong direction then it doesn’t matter how fast you are going you are not making progress.”
When trying to level up the direction you are pointing in, 3 people done well allow a positive sum outcome. So done well, three people are better than one.
You have to plan and execute.
Planning is better if you can discuss it with people.
Even if after the discussion the plan is only 1% better it is time well spent if you have more than 100 people in the company. I normally find that the plan (direction) is 50-500% better after discussing it with Ben and Jeremy.
You want to have a discussion with people who can help you upgrade the plan.
Also, they help you find your blind spots.
Good people make you find them faster.
The core job of a CEO is to find the direction.
But nobody is almighty.
How do you set strategy?
It is iterative.
I would argue that the vision we have today was unimaginable a couple of years ago.
The vision has to change.
It is essential that it changes. If you are not upgrading the vision constantly then I think something is off.
At a minimum, I try to write out an updated vision document once a year. But normally it happens organically throughout the year.
It is essential to do a good review.
It is a cycle.
Then you loop back to the start again.
I write a blog.
I send it to some people.
I have a discussion - a free-form conversation.
You want to set the expectation for the meeting.
The free form allows you to course correct.
It is not about Batko (the CEO) writing and sitting down to set the strategy.
You might have already figured out half the strategy and have some answers, but others don’t know that.
They are not you.
In the team, the further you’re away from the founder the more you don’t know when things shift, you need to bring them on the journey.
How do you communicate the strategy?
What most of us do on a daily basis is knowledge work.
The cycle of knowledge workers looks like this:
Reading thinking writing talking building.
I find writing to be the most important component.
I write once a week about product and once a week about the business.
Writing is like going to the gym for your mind.
You get good at strategy by doing strategy.
You get good at vision by doing vision.
The best way I know of to get good at strategy and vision is by writing about them regularly.
It is about professional self-development.
How do you do something? Go figure it out!
You get more responsibility if you teach yourself how to do new things AKA figure out things on your own.
If you can’t figure it out, then you get minimal responsibility and no autonomy.
Some people won’t don’t like opportunity, some love it.
But one person’s anxiety is another person’s liberation.
For me, there are roughly 10 people who are part of the core strategy process at Edrolo.
It is not a democracy, ultimately the 10 people make a decision and we have to move.
We listen, but we’re not doing a vote.
We try not to allow people to be unreasonable.
You get the behaviour you allow.
If you want input, you write a doc on vision and we have that discussion.
Trust is earned, faith is given.
You have to earn your spot to do strategy.
How do you set goals?
Each team is different.
Easiest goals are a deadline.
On the 1st of Feb school starts we have you have to get a feature out by then.
You have 10 weeks, that’s the resourcing - can you figure it out? How? That’s on you.
There’s almost always a boundary. Make it explicit - ie deadline, resourcing.
OKRs often don’t have a deliverable with a deadline.
We can’t just release a feature and the next time around it screws up.
For teachers changing something, every year is a bug, not a feature!
We have to shape our goals to solve that.
We try to have everything we do be the best thing we have ever done.
There is no point in building something worse than already exists.
We have hard deadlines that are not up for debate.
It is almost always intense close to the deadline, no matter how well we plan, so we always have a final sprint, a period of craziness before the deadline.
How do you communicate sensitive information?
We don’t always do it well. There is no set formula I’m aware of. Basically, for the most sensitive information, you have a waterfall release and ‘read in’ people as it makes sense before entire company-wide comms.
Do you have any other advice for me?
Write all the time!
Write for communication and then have free-form exploration writing.
Do 1 hour of writing, not 10 mins not 3 hours.
Send each other the writing and discuss it for an hour each week, 15mins per person.
The cumulative outcome of that is INSANE.
We’re all knowledge workers.
So, knowledge creation is likely the most important skill. I find writing to be improving at ‘knowledge creation’.
If you show more initiative, you should get more opportunities. If you write more you should get more opportunities.
I’d make writing optional, you are not forced to do anything. But those who opt in should get more opportunity if their writing is high quality.
Create a culture of writing that everyone wants to get on board.
Show initiative yourself.
Create scarcity that others want to be part of.