https://michaeldehaan.substack.com/p/encouraging-self-doubt Michael DeHaan LLC :: Speaking Tech SubscribeSign in Share this post Encouraging Self-Doubt michaeldehaan.substack.com Copy link Twitter Facebook Email Encouraging Self-Doubt Michael DeHaan 1 [https] Apr 11 In many ways this blog is me working through past workplace trauma as I effectively subtweet past situations from long ago, so thanks for putting up with it. I wanted to talk a bit about character values in leadership -- what we sometimes get vs what I value. I'm also trying to not "preach to the choir" here, so I'm also going to try to not say a lot of obvious things or share advice that isn't really actionable. The internet has enough of that already. I think self-doubt is probably the most undervalued virtue if you want to be successful with a project, company product idea. Perhaps the most valuable virtue. One my first really good managers used to say "Seek first to understand", which is apparently also from "Seven Habits of Highly Effective People", which I have't really paid attention to. Anyway! Excessive confidence seems to work to impress some people early on, but total belief in your own abilities and eventual world domination is going to make you think you can do anything, and that gets in the way of making good decisions. You may find that you're suddenly not that successful, and then won't be able to see why. Being around that confidence for others is also frankly, exhausting. Instead, with the proper degrees of self-doubt, you will hopefully know the areas you need to improve, be able to shore them up, get help, and pounce on the right ideas and moments, not just the first ideas that come along that matched your original logic. You'll realize good ideas can come from anywhere, and feel better knowing it's ok to change things at any time, rather than worry about being proven wrong. Being wrong doesn't have a consequence, it's just a result of learning. Especially in startup terms, time and efforts are limited and everything has a clock. That's how much the funding lasts (or you become too well funded to purchase) and when a competitor comes along and the whole paradigm of tech fashion has shifted the winds in a different direction. Confidence works against you as you are watching that clock tick. As a simple example, for a developer, knowing what you are good at and not good at will give you a better idea of where you should use a library or service for something rather than doing it yourself. When running a business, it will also help you better gauge your success from the opinions of others - whether you are solving their problems, whether your customers love you - and what you need to do to win them. Are there parts of your product they don't like or that is difficult to them? Maybe it's not them being wrong or stupid but something you should change. (If you ever start to see your business developing contempt for the customer, root it out, that is the source of 1000 bad product decisions coming down the pipe) Cultivating the feeling of "We're awesome and we're going to kill it" is the wrong place to start if you want to make great products. It's the wrong feeling to give a team. A better feeling to cultivate is "we're going to work really hard to make sure we do a good job and make great products that really help our customer". Often I've seen posts on that orange-colored message board where people are just out of school and rushing to "find a technical co-founder" (shudder) and "have a startup", and pretty sure that no matter what they do, they think they are going to get acquired. They should instead know that their chance of failure is in fact extremely high, and any previous weird cultural "glorification of failure" is a completely backwards cult-like thinking process. These folks will end up burning a year's worth of money and probably still won't learn anything from their overconfidence. They need much more domain experience to be able to hit a good target. They should realize they don't know all the things they don't know and get that experience first. An overconfident company also comes across as arrogant when talking with customers, they over-promise and under-deliver. They make claims that are too large and maybe even build something too big to ever release their largest plans. A better company will describe what they do and don't do, while working to get better at areas they aren't so good at - and the customer will appreciate the honesty, efforts, and service provided, because it will really be a partnership. They will be able to learn from the customer, and realize that in many cases, the customer knows way more about the domain than them. Another main reason to encourage self-doubt is to always be able to revisit your assumptions and to have humble attainable goals. Maybe I've just worked at too many places that felt to be run by narcissists, but facts change. To keep on against a goal without evidence that there's a reason to be pursuing it is a wasted effort. Some of the hardest work conversations I've had were with people that project absolute confidence, because you can never provide advice or ask a question - you can never pause to say "what do you think?" or say "I don't know" and just sit there and think about it for 10 minutes, together, throwing out random ideas and talking as friends. You don't have conversations, you either provide the answer they want or need, or you're a problem. They expect you to read their mind. They don't benefit in getting more data. There's a feeling of strata and subservience always in the conversation. They don't value the outside perspective or other ways of thinking. Without ability to question yourself, things can't improve. When people have too much self-confidence, they also tend to doubt others rather than themselves. This can create an atmosphere of mistrust, which I've seen happen a few times. Often there are multiple answers to a question, and averaging all the possible answers to question makes it look like everyone is wrong, and you choose a mediocre solution and a result. Much of the corporate world does that all too often. Great things are often made with unique perspectives. Doubt yourself so you always want to do better, but trust your people so they feel like they want to help you become better also. Just asking yourself "is this the right path?" and "am I sure about this?" about your own ideas and so on is a good step. The future is completely fluid, don't tie yourself to make future decisions based on past decisions and beliefs. I'm a big fan of meetings where people can stop talking for 3 minutes and just think about things. Of corporate cultures where people can throw out ideas without thinking they need to be perfect or be judged from saying something wrong. The world of overconfidence and always wanting to look perfect holds us back from improvement. When we feel we cannot show our own doubts and the things we don't know to others, and we act on incomplete information and do suboptimal work as a result. Doubt is good. 1 Share [https] [ ] Create your profile [ ] Your name[ ]Your bio[ ] [ ][ ] Subscribe to the newsletter 0 subscriptions will be displayed on your profile (edit) Skip for now Save & Post Comment Only paid subscribers can comment on this post Already a paid subscriber? Sign in Check your email For your security, we need to re-authenticate you. Click the link we sent to , or click here to sign in. Aseem Dua Apr 11 This reminded me of something cited by Stephen Fry in a totally different context, (Munk Debates, opening) a statement from Bertrand Russell [1], "The fundamental cause of the trouble in the modern world today is that the stupid are cocksure while the intelligent are full of doubt." [https] Personally, I've found allowing myself to be wrong as a major burden lifted off me. Professionally, I feel it's very important to cultivate an environment where being wrong is not a catastrophe, but treated with a sense of ok-ness and learning. [1] https://quoteinvestigator.com/2015/03/04/self-doubt/# more-10737 Expand full comment Reply TopNewCommunity No posts Ready for more? [ ]Subscribe (c) 2022 laserllama Privacy [?] Terms [?] Collection notice Publish on Substack Get the app Substack is the home for great writing This site requires JavaScript to run correctly. Please turn on JavaScript or unblock scripts