Encourage your candidate to take ‘small’ initiatives such as opening a meeting or offering an opinion, and to be alert to potential needs his team may have (coffee, fresh air, a flip-over et cetera).
Set goals together with your candidate. In what situations would he like to take more initiative? Make sure the goals are SMART (Specific, Measurable, Attainable, Realistic, Timely).
Encourage your candidate to ask others for 360º feedback regarding his initiative. What goes well and what could be improved? Discuss the results with the candidate.
Evaluate with your candidate in what situations he finds it hard to take initiative and in what he does.
Give your candidate an assignment to think about future opportunities for himself, for the department, products, or services. Which initiatives and responsibilities could he personally take in order to succeed?