It’s become a bit of a cliche that leaders need to let their reports make mistakes. When you let your reports make mistakes, the common wisdom goes, it shows you trust them, and allows them to learn from their errors. Most importantly, if your employees are afraid of making mistakes, they will be afraid to take risks, or voice their opinions, and, in the worst cases, creativity can be stifled as learned helplessness sets in.
While I agree with this wisdom (so much so that I’ve included some links below to support the idea), there are times when leader must head-off mistakes. Here are a few examples:
- Starting a project that likely won’t ship, or won’t benefit the company.
- Believing a pet project will get them outsized recognition.
- Making a decision that will commit the company to something that isn’t a good long-term fit.
- Over-emphasizing long-term or abstract benefits to the detriment of shipping.
- Diving in too quickly to make changes to a system, resulting in unforeseen or unpleasant consequences for other teams.
These examples all represent significant time wasted on efforts that don’t contribute to the company goals.
Preventing big mistakes

Two things should generally prevent big mistakes from happening. First, managers should be in the weeds enough to see the mistakes coming and be able to stop them. Even managers who are checking in regularly, and reviewing PRs and so on can miss this, however, if they are focused too much on now, and not enough on the future. This is a mistake I’ve made, as I tend to focus too much time in 1:1s solving problems and getting status updates, and not enough time asking about upcoming projects and planning. This has sometimes caused me to be late to the party when it comes to projects that should be stopped, and I’ve learned the hard way that the more momentum a project has, the harder it is to stop.
Second, the company and team goals should be clear enough to everyone that people should be able to steer themselves away from big mistakes. If teams or individuals are going off the rails frequently, it may be a sign that they are losing touch with the company goals. The solution might be as simple as having more frequent all-hands1, or improving or better-communicating the company strategy. Leadership is responsible for ensuring a genuine understanding of the company goals are and how each person contributes to them.
It’s worth pointing out that even with good management and good processes, you will always encounter some people who push away from company goals. Some give and take here is not a bad thing: Engineers should be naturally curious, and you never want to stifle that curiosity. However, some engineers can become overly focused on the shiny new thing, or a theoretical optimization they read about. Sometimes, engineers push hard for “doing things right” even if the practical value of doing so is minimal and the cost is high. These are the people who need the most coaching.
Bottom line
As a leader, it’s your job to prevent big mistakes from happening. You should provide guidance about how decisions should be made, and you should check in with reports while they are planning to make sure they are going in the right direction.
When mistakes do happen, you should work with your report to make sure they understand the mistake, the impact it has, and how to resolve the issue. You should also help them correct their mistakes and reinforce the notion that you still trust them and are on their side – after all, it was your mistake, too.
If you find yourself correcting your employees a lot, it may be a sign that you have not laid out the right strategy for them to follow, or have not communicated it correctly.
Links
Here are some of the many management articles arguing to let your employees make mistakes. The important thing is not to stifle positive curiosity and energy.
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http://www.amyreesanderson.com/blog/good-employees-make-mistakes-great-leaders-allow-them-to/
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https://www.uschamber.com/co/run/human-resources/how-to-handle-employee-mistakes
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https://www.forbes.com/sites/amyanderson/2013/04/17/good-employees-make-mistakes-great-leaders-allow-them-to/
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https://www.rewardgateway.com/blog/why-letting-your-employees-make-mistake-can-ultimately-lead-to-a-more-engaged-workforce
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https://tandemhr.com/allowing-employees-to-make-mistakes/
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https://www.recruiter.com/recruiting/why-you-should-let-your-employees-make-mistakes/
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https://www.linkedin.com/pulse/why-letting-your-team-make-mistakes-good-idea-wendy-scott/
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https://www.linkedin.com/pulse/your-best-employees-make-mistakes-jacob-jenne-dgsqc/
Notes
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Of course, no meeting is more expensive than an all-hands, so you must balance the value of additional focus with time it takes to have these meetings. In my experience, it’s helpful to tie Engineering all-hands meetings with major company changes, but to have them about every half or quarter. ↩