Here’s a actionable overview of how to handle your founder to help your startup be as productive, happy, and successful as possible.
1. Focus their energy on the task at hand.
Founding CEOs usually get to where they are because they are OK at doing everything and great at doing one thing. You need to help the CEO change his or her behavior to become comfortable with delegating more so s/he can spend more time on the 1 thing s/he does best.
To do this, be a ‘bulldog’ and focus the CEO’s energy on the task at hand, make it time limited, and keep reminding him or her to not go off on tangents: ‘yes, that’s a great idea, but for the next 10 minutes, let’s focus on part B before we go to part C.’
2. Don’t let the perfect be the enemy of the good.
Because the founding CEO puts so much personal energy into their company, it’s like their baby, and they want it to be perfect. To avoid the problem of the ‘perfect being the enemy of the good,’ you want something to be done when it’s at 80%. If it’s only done at 100% then you’re spending too much time on it. Having the authority to say when something is done in a particular area, and holding the CEO to a certain pre-defined number of revisions when s/he is consulted, can help with this.
3. Visioning and ideation.
Sometimes founders don’t know what they think until they see what they say. You may need to go on the journey with them, and even if all you’re doing is listening to them ramble, they will value you for providing even an occasional sentence that gets them to the next level of company strategy. Steve Jobs was famous for taking long walks, so if you find yourself getting stuck at a computer with a blank document, try talking it out and recording the conversation. You can then send that mp3 to a transcriptionist and then give that to a writer to clean up and turn into a one pager.
4. Provide Food.
Founding CEOs often have a day full of back to back meetings, sometimes for 6 hours at a stretch. If you bring them a sandwich they will be super appreciative.
5. On taking care of people.
One thing that keeps startup founders up at night is being able to make payroll. Don’t remind them how many people are depending on the company to feed their family, send the kids to high school, or care for aging parents. It only adds to their stress.
6. Mood swings require emotional jujitsu.
Don’t be fazed if a founder gets annoyed at people for no apparent reason. Founding CEOs are a special breed of visionaries who think that their idea has a better chance than anyone else’s, even though most startups fail within 3 years and have a <5% success rate. So emotionally speaking, they are wired differently. Allow them this space to be cranky and, when possible, do some jujitsu by redirecting their energy in a positive direction.
For example, if your founder is annoyed at an offshore contractor who isn’t doing work that’s up to par, consider the cultural context. Is the person acting OK within their cultural context (e.g. going as far as they can without asking for help, and trying to show progress rather than interim milestones to the supervisor? If you expect someone in a hierarchical culture to treat a manager as a peer, that will feel awkward for them unless you have a training program on cultural sensitivity and how to work with Americans).
Try to turn the founder’s frustration at the person into a checklist of what the founder would count as good work. Then draft that checklist as an email for how you can improve communications with the person the founder is mad at, and run it by your founder. They may thank you for seeing their intentions behind the frustration!
7. Notice what gets your founding CEO frustrated or energized. For example, some founders may find that tasks are easy to plow through but making 3 decisions in a row on the same day is agonizing. If this is the case, prioritize the decisions to be made so that your founder doesn’t feel overwhelmed and stuck.
8. Set focus time on the calendar for top priority things – i.e. spend 1 hour in the same room where you and your founder only work on high priority items. You might think this is babysitting but your founder will thank you for helping keep him or her focused rather than checking email all day. This is particularly important in a company culture where people respect and respond to meeting invitations more than they respond to emails or requests for edits on long documents.
Got any other suggestions? Share them in the comments!
Katharine Bierce has worked with startup founders and executives at tech companies large and small in marketing, project management, recruiting, operations and more. She enjoys turning great ideas into reality and is currently getting technical with email marketing after being a generalist and "full stack marketer." In her free time, she enjoys yoga, singing, hiking, planning and attending “tech for social good” Meetups and advising nonprofits. Katharine graduated Phi Beta Kappa from the University of Chicago with a degree in Psychology.