Hebrews 12:1 (NKJV)

Therefore we also, since we are surrounded by so great a cloud of witnesses, let us lay aside every weight, and the sin which so easily ensnares us, and let us run with endurance the race that is set before us,

Eisegesis: 

You are surrounded by the saints and loved ones in the heaven who are cheering you on to win the race.

Exegesis:   

This verse does not indicate that those in heaven are able to watch us and witness what we are doing. Rather, it means that they are an actual witness / testimony (because of the life they lived and the faith they had) for us to use as an example as we run our daily race. 

Some preachers have used this verse to imply that when believers die they go to heaven and watch over us.

But there is nothing in the scriptures to indicate that when believers die they can / are able to watch over us. There is also nothing to indicate that they are even aware of what is going on here on earth.

In fact, there is ample reason to assume that they know nothing of what is going on here on earth because they would be lost in wonder, love and praise in the presence of God. Heaven is described as a place of perfect joy and worship, disconnected from earthly imperfections (Revelation 21:4).

The scriptures are clear that when we die we go directly to be with the Lord.

2 Corinthians 5:8 (NKJV)

We are confident, yes, well pleased rather to be absent from the body and to be present with the Lord.

Once we leave this earth and enter into the presence of God, there is a total disconnect from this world. Scripture gives no precedent to suggest that saints in heaven are preoccupied with earthly events. Instead, they are fully focused on worshiping God.

In fact, if we were even able to have some sort of idea of the situation on earth it would disrupt the perfect harmon of heaven. Because in heaven you would have the perfect environment not affected with imperfection and sin. The perfect experience of fulfillment would be tethered with thoughts of dissatisfaction or worry for those left behind.

Context:

To understand the great cloud of witness in chapter 12, we need to understand the cloud of witnesses (people / heroes of the faith) mentioned in the previous chapter (11). They are not a cloud of witnesses in the sense that they are sitting around observing us; rather, they are a testament to the power and blessing of a life lived by faith.

Some preachers use an imagery to describe this verse alluding to a big heavenly stadium and we are here on earth running a race while they are cheering us on. This is not the contextual image of this verse. Instead, the focus is on their testimonies as examples of faith for us to follow.

The picture that Hebrews 12 is describing is that the cloud of witnesses are those who lived by faith in that they chose to live by faith over everything.The cloud of witnesses refers to the Old Testament saints who were blessed and benefited because they lived by faith. Their testimonies stand as a powerful encouragement for us to live by faith as we run the race of the Christian life.

The motivation for running “the race” is not in the possibility of receiving praise from “observing” heavenly saints. Rather, the runner (the believer) is inspired by the godly examples these saints set during their lives.

The great crowd is not comprised of spectators but is instead made up of those whose past lives of faith encourage others to live that way (cf. Hebrews 11:2, 4, 5, 33, 39).