I heard the lead singer for MercyMe, Bart Millard, being interviewed one day on the radio. They were discussing his hit song, “Finally Home,” which was written to his father who has passed away. In the song, he sings about finally getting to Heaven and seeing his father again. He longs to tell him all about his life and how much he has missed him and loves him. He went on to say that many well-intentioned people often say things to him like, “I’m sure your dad is so proud of you,” or “He’s smiling down on you from Heaven.” As much as this is meant to encourage him, he said that he believes his dad has much better things to do than just sit around and watch him all day—like worship almighty God. He said that he had just not found any scripture to support that he’s “watching over me.”
Well, this really got me thinking. I immediately thought about the passage of scripture in Hebrews 12:1 that says, “Therefore, since we are surrounded by such a great cloud of witnesses, let us throw off everything that hinders and the sin that so easily entangles, and let us run with perseverance the race marked out for us.” (NIV) The “witnesses” are all those mentioned in the previous chapter that are commended for their great faith. I have heard this verse interpreted that these “heroes” in the faith are watching and cheering us on in our journey of faith. The Message version reads, “Do you see what this means—all these pioneers who blazed the way, all these veterans cheering us on?” So this intrigued me: do they “watch over us,” cheering us on? I found that as I looked up many commentaries on this verse, most of them disagreed with this interpretation. Here are a few:
The “great… cloud [assembly, mass] of witnesses” was introduced to us in Hebrews 11. They are the heroes of the faith. It is not suggested here that these men and women now in heaven are watching us as we run the race, like people seated in a stadium. The word “witnesses” does not mean “spectators.” Our English word “martyr” comes directly from the Greek word translated “witness.” These people are not witnessing what we are doing; rather, they are bearing witness to us that God can see us through. God bore witness to them (Heb. 11:2, 4–5, 39) and they are bearing witness now to us. 
The picture here is of an arena; the spectators are the heroes of faith listed in the previous chapter; the runners are the believers going through trials. (This image does not necessarily imply that people in heaven watch us or know what is going on here on earth. It is an illustration, not a revelation.) 
The life of faith has been amply attested by this great cloud of Old Testament witnesses. (This does not mean that they watch believers today.) 
They are not witnessing (watching) us, but they are bearing witness (testifying) to the faithfulness of God. But even though those in Heaven may not observe our daily lives, another verse implies that they may be informed of earthly events that have eternal significance: “In the same way, I tell you, there is rejoicing in the presence of the angels of God over one sinner who repents.” (Luke 15:10) Aren’t those who have died in Christ in the presence of God and the angels in Heaven? I would like to think that they are a part of this Heavenly celebration, especially if the “sinner” is a family member or a loved one that has repented. Or maybe their loved one was the person that shared their faith resulting in repentance.
It is a mystery to me what Heaven will actually be like, but I do know that we will be with God and He will be on the foremost of our hearts and minds. John gives us a glimpse of Heaven in the book of Revelation, and it all focuses on Him. He describes four living creatures that never stop saying, “Holy, holy, holy is the Lord God Almighty, who was, and is, and is to come.” And “twenty-four elders fall down before him who sits on the throne, and worship him who lives forever and ever. They lay their crowns before the throne…” Then John “heard the voice of many angels, numbering thousands upon thousands, and ten thousand times ten thousand. They encircled the throne and the living creatures and the elders. In a loud voice they sang: ‘Worthy is the Lamb, who was slain, to receive power and wealth and wisdom and strength and honor and glory and praise!’”(Revelation 4 and 5) Wow! I believe in Heaven we will be completely enthralled with who God is, and we will join the worship and praise of the angels. And I bet the things of this earth will be very far from our minds.
So, even though our loved ones may not watch over us, it is a comfort to know that Almighty God watches over us: “The Lord will keep you from all harm—he will watch over your life; the Lord will watch over your coming and going both now and forevermore.” (Psalm 121:7-8)
Wiersbe, Warren W.: The Bible Exposition Commentary. Wheaton, Ill. : Victor Books, 1996, c1989, S. Heb 12:1
Wiersbe, Warren W.: Wiersbe’s Expository Outlines on the New Testament. Wheaton, Ill. : Victor Books, 1997, c1992, S. 710
Walvoord, John F. ; Zuck, Roy B. ; Dallas Theological Seminary: The Bible Knowledge Commentary : An Exposition of the Scriptures. Wheaton, IL : Victor Books, 1983-c1985, S. 2:809