The Messenger of Allah ﷺ asked Abu Bakr, "When do you perform the witr prayer?"Abu Bakr replied, "At the beginning of the night, after the evening prayer."The Prophet ﷺ then asked, "And you, Umar?"Umar answered, "At the end of the night."The Prophet ﷺ said, "As for you, Abu Bakr, you have taken the cautious approach. And as for you, Umar, you have taken the strong approach."
قال عبد الله وجدت في كتاب أبي حدثنا أبو سعيد مولى بني هاشم حدثنا زائدة حدثنا عبد الله بن محمد
أن رسول الله ﷺ قال لأبي بكر متى توتر قال أول الليل بعد العتمة قال فأنت يا عمر قال آخر الليل قال أما أنت يا أبا بكر فأخذت بالثقة وأما أنت يا عمر فأخذت بالقوة
Its isnad is hasan, because of Abdullah bin Muhammad bin Aqeel. Ibn Majah and Abu Dawud narrated it through a sahih route, 2/67, no. 1434, in the chapter on Witr, Witr before sleeping, from the route of Hammad, from Thabit, from Abdullah bin Rabah, from Abu Qatada. It is likewise found in Ibn Abu Shayba, 2/282, Abdul-Razzaq, 467, Tabarani in Al-Kabir, 17/303, Ibn Khuzayma, 185 and 1084, and Hakim, 1/301, who graded it sahih, and Dhahabi agreed with him.