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I had someone like that, and what helped was framing stretch assignments as experiments, not tests. We broke projects into smaller milestones so it felt less risky. Sometimes reducing the fear of failure opens up space for growth.
For me, I really struggle with new things, which is normal to a degree. You have to muddle your way through sometimes if you’ll ever get better at it. Definitely relate to the fear of not being perfect. I try to give people a space where they can do big or hard things and make mistakes and learn, but it is up to them to go for it.
Does this employee understand the difference between low stake vs the higher impact tasks? For example: the two of you looking at the past week’s work and then have the employee identifying what was low stake/high impact. Looking at wins and strategy to identify the high impact while this person is in the weeds?
Does this employee have someone to delegate the lower stake tasks? In the employee’s eyes, that work still needs to be done and that is where they are getting their annual review metrics graded.
One thing that helped me switch my mindset was assigning fictitious salaries to the work that I do. For example, running reports on financials and getting them ready to analyze is a $10 task. Analyzing the report is a $20 task. Delivering a presentation to senior leadership about the report is a $100 task. Designing the presentation is a $20 task.
Something to consider when working with this employee. Returning to “safe” is a natural reaction to something that is new is introduced. Instead of focusing on how much time this person is staying in “safe”, try shifting your conversation to how much time is increasing into this new territory of high impact.
Yessss this works for me too - I completely forgot about this, but I started looking at tasks based on my hourly rate and whether that's worth paying me to do or better off delegating/automating.
The downside though is that you need to keep your ego in check. Balance between that and the humble mindset that no task is beneath you. That mindset needs to be adjusted depending on the role, the business, and the task.
I’m a Career/Leadership Coach. Have you considered having her tag along with you for a day to show her how you would approach some of the work you’d like her to do? Is there another co-worker you could pair her with to get her up to speed on owning bigger projects? Maybe there is a checklist or other tool that you could use that would help “nudge” her to be more proactive? She retreats to the low-stakes tasks because she’s absolutely terrified of the new challenges where much could go wrong. However, this is an excellent opportuntiy to be a mentor or rally around her a bit more. When she knows she has the support, she’ll likely feel more at ease. You also mentioned the word perfection (something I struggle with too). Well all know what pefection means, but when you offer a word like “impact,” that can mean a lot of different things. Consider defining what impact would look like or how it could be attained. Maybe even a list like:
I - important phone calls first
M- managing expectations
P- proactively call....
You get the point. I hope this helps. I’m curious to know, what industry. are you in? And if you ever need anything, www.mikedoriacoaching.com
This is me. Thank you for posting this question and trying to help your employee.