Ask HN: How much info should founders share with early stage employees?

Demoralized is one thing, but also if enough partnerships are falling through they might get the sense that you’re not a good business person. Which may also be an accurate take away that you as a leader don’t want to hear/realize about yourself.

Without having been the leader of a startup I’d say the best thing to do is treat yourself like anyone else in the team ie the expectation of equal sharing back and forth. Help the team help you find out what your strengths are and what your weaknesses are.

Don’t try to hide your weaknesses or hope to get better at it. Especially if trying to hide/improve weaknesses are taking away from showcasing strengths. Instead get your team to hire in people to fill your weaknesses and learn from them. Meanwhile, double down on your strengths and continue the transparency and working as a team member.

- Share info that enables independent decision making and actions so your team can help recruit new teammates, sell to customers, choose designs, and at a personal level, make personal financial decisions. If not, you're hobbling your team, who are your main shot at success. Just be clear that info is internal.

- Level anything forward looking, good or bad. Relatively few people understand that good sales requires significant loss rates, what a slog fundraising typically is, etc, so when some big lead doesn't convert or a process takes awhile, bigger issue is avoiding unnecessary heartache & whiplash. So share progress good & bad, but always level it. Partnerships, key hires, leads, VCs, talks, releases: celebrate real wins and analyze losses, but it's a marathon, so don't pump people up too much on the barrage of things outside of your control. The sharing is mostly dependent on the experience of the individual receiver.

Sharing things that are in-progress is harder. I'd recommend attaching timelines and probabilities. Basically saying "this should happen in the next X days" and "we're trying this idea, it may not work but we'll know in roughly Y days."

There are two huge upsides to a small, tight team:

a) there are LOTS of decisions made every day in every area. If people know what else is going on, they should be able to make better decisions. aka "This doesn't make sense to do for one customer.. but if there are 4 others in the pipeline, it's way more compelling."

b) people with varying strengths and areas of focus will not have your blindspots and perspectives and will see/understand things that you don't. Lean into that and you'll get a better solution.

Background: I was employee ~25 at Twilio, launched Okta's API security product, and am currently employee ~20 at ngrok.