Human-Machine Cooperations (HMCs) can balance the advantages and disadvantages of human computation (accurate but costly) and machine computation (cheap but inaccurate). This paper studies HMCs in agglomerative hierarchical clusterings, where the machine can ask the human some questions. The human will return the answers to the machine, and the machine will use these answers to correct errors in its current clustering results. We are interested in the machine's strategy on handling the question operations, in terms of three problems: (1) Which question should the machine ask? (2) When should the machine ask the question (early or late)? (3) How does the machine adjust the clustering result, if the machine's mistake is found by the human? Based on the insights of these problems, an efficient algorithm is proposed with five implementation variations. Experiments on image clusterings show that the proposed algorithm can improve the clustering accuracy with few question operations.