17 Things a CEO Does — When Not Microdosing

Recently, I self-administered some CEO therapy.

The efforts of any leader are delivered in 3 distinct buckets. Pexels

As part of my process — which may have appeared like awkward day-dreaming or a potential micro-dose day — I realized the efforts of any leader are delivered in 3 distinct buckets: Foundations, Constants and Ruddering.

You can read about how those work here.

What I’ve been told (by myself) is that a critique of my activities — nay, the opportunity to be subject to potential declarations of my ignorance, simple-mindedness and short-sightedness — will invariably aid me in becoming a better leader.

So, as part of my therapeutic regiment (which I’ve prescribed), I‘m posting the results of my reflections.

While I’m vain and totally self-conscious, I do hope you provide me your perspective.

My inside voice swears I can bear it.

Dave Balter’s 17 activities as CEO of Mylestone

FOUNDATIONS: The processes you plan in advance, which become the basis by which you manage.

Here are a few things that I consider critical to producing a high performing team:

1. Develop the Company Playbook. “Why do we exist?” and “How do we get there?” are more than existential debates. You can’t bake the cake if you don’t know the ingredients.

2. Plan & lead strategic offsites. Aim for once a quarter, but the rhythm is often dictated by major forks in the road, and when there are additions (or subtractions) on the team. People come and go, teams change, and a good offsite can recrystallize the group.

3. Measure spend on a weekly basis. “We have 14 months of cash remaining,” hides a basic fact: every single decision impacts how long you exist. Clarifying to, “we have 56 weeks of cash to go, and next week will be 55” trains the individual to act with great consideration.

4. Individual management and mentorship. Even when you chat dozens of times a day, weekly one-on-ones suss out the real dirt. Stay connected, help individuals know where to focus, and unblock anything standing in their way.

5. Generate culture. Culture doesn’t happen on its own, it needs to be constantly massaged, managed and maintained. Set and discuss values early and often; make sure there’s something unique, freaky or fun — and most importantly, teach the entire team to be accountable to one another.

Setting your foundation. Pexels

CONSTANTS: Your personal unfair advantages you deliver on every day.

Putting these on paper reminds me every day what I have to do tomorrow:

6. Sell something. Opening deals is fun, but closing deals is thrilling. And, no company starves when there are clients around.

7. Network with Amazon / Alexa. Gotta kiss the ring. Especially when the hand it’s on can feed you — or crush you.

8. Connect with Current Investors. You cannot “get it and forget it.” These people have a vested interest in your outcome; more importantly the good ones will cheer-lead when you’re too far down — and tell you the truth when you’re too far up.

9. Raise Capital. You. Yes, You. You are raising capital right now. You just didn’t know it yet.

10. Engage the Press. They tell the story you can’t. They’re often friendly, but the majority aren’t your friends — don’t get confused by that.

11. Write, right? Like this. Or this or this.

12. Fraternize with Frenemies. Rising tides lift all boats, so stop being so stand-offish. Generate good will and karma will take care of itself.

13. Recruit Talent. The entire team should be trained to attract and engage top talent — but at startup stage, obtaining the best has to be the CEOs job. And, for heaven’s sake, make job posts fun.

RUDDERING: your opportunity (and ability) to fix challenges, as they arise.

Here are a few activities that unblocked problems and set guideposts where they were needed.

14. KPI reminder session. Team stumbles on product update, and the latest release doesn’t align with KPIs. Pull the fire alarm, call an immediate team meeting to make sure everyone is aligned on objectives. This will happen only, say, 1,000 more times over the course of your business.

15. Answer Daily Questions on Strategy. “Should we redo the homepage?” “How do we evaluate which segments to focus on?” “Why are there no forks?” Answer fast and often. Nothing kills momentum like individuals who are guessing.

16. Massage the culture. In an age of digital nomadity and Slack-as-your-core-communication tool — and, hell, the rise of millennial — reinforcing “how we behave” with vigilance is the key to a high performing team. Rapidly extinguish any cultural flames before they become fires.

17. Manage Hire-to-Start Window. The time between hiring a new employee and the day they start is a magic window. The team must be prepared for change. For the new hire: continue building the personal relationship, and provide them a continuous flow of inspiration. For your team: activate them to build their own relationship, prepare them for any transition of management, and clarify how the new role will fit in with daily activities.


+18. Personal Primping: Get your ‘doo trimmed, your teeth crowned — and cough for the doc’ once a year.

+19. When not doing these things, read Ayalet Waldman’s A Really Good Day.

Dave Balter is CEO of Mylestone, a company that transforms photos into stories you can listen to on Alexa devices, and a Venture Partner at Boston Seed Capital.

17 Things a CEO Does — When Not Microdosing