Q: We recently hired someone who came highly recommended, but he seems unable to make a decision without asking me about every little detail. He seems to doubt himself and his abilities. How do I encourage my new employee?

A: Take stock in four factors and act accordingly. 

1. Competence. Does he have the skills needed to fulfill his job requirements? He may have come highly recommended, but that doesn’t mean he has what it takes. Does he need training or mentoring in this new job? Has he had sufficient orientation? Has he demonstrated the needed competencies in past employment? Without competence, he can’t succeed. “In every thing a prudent man acts with knowledge.” (Proverbs 13:16)

2. Clarity. Does he clearly know what’s expected of him and his scope of decision-making? Fuzziness breeds uncertainty. He needs boundaries. What matters are in his circle of responsibility and what aren’t? What kind of initiatives and decisions come with his job description? You want him to “own” his job and his tasks. “The wisdom of a prudent man is to discern his way.” (Proverbs 14:8)

3. Confidence. How can you encourage him? That’s exactly the question you posed. Confidence naturally follows competence and clarity. But encouragement from the boss is a big boost. Build him up with expressions of your faith in him. Include two phrases. First, “I trust you.” Look him in the eye and let him know you believe in him. Then set him free to be fallible: “I’d rather you ask for forgiveness than permission.” He won’t get clobbered for reasonable risk-taking. “Anxiety weighs one down, but a good word makes one glad.” (Proverbs 12:25)

4. Culture. Is your work culture promoting achievement and initiative? Culture is a powerful, invisible force that shapes everyone’s behaviors. Does your atmosphere lean more toward people pleasing and dependency than accomplishment and initiative? Does the tone tend to breed independent thinking and creativity, or conventionality and avoidance? Make sure your culture rewards achievement and initiative, and you’ll get more of the same.