I would like to suggest an interpretation of Heb. 13:17 which takes the context fully into account. As in any exposition of Scripture, the context is absolutely key. The first context of a verse is the clauses of the verse itself, then the surrounding verses and chapter, and then the book in which it is located. And, finally, no verse can be properly interpreted without the context of all of Scripture and its teachings.
Here are some various translations of the verse:
You can see how different the first clause appears in these different translations. “Yielding to a guide” has a much different flavor than “obedience to one who rules over you.” When someone receives guidance (from a respected source), he considers it, and if the guidance seems sound, then he follows it. But, obeying a ruler means unquestioning obedience. The difference here only demonstrates the difficulty in translation work, which is often prejudiced by theological traditions.
Let us first consider the meaning of the verb translated “obey” (at the beginning of the verse) by many translations. The Greek verb here is peitho (Strong’s #3982). The Greek scholar W. E. Vine states that it means “’to persuade, to win over,’ in the passive and middle voices, ‘to be persuaded, to listen to, to obey... The ‘obedience’ suggested is not by submission to authority, but resulting from persuasion.” 
Dr. Ray C. Stedman, in his commentary on Hebrews, wrote the following on this matter of “obey” in Heb. 13:17, which also includes important observations on the ones leading here and the nature of the “submission”:
Several things should be noted about Hebrews 13:17 and 1Thess 5:12. The word "obey" comes from the Greek peitho, "to persuade." The present imperative middle form, used here, means "permit oneself to be persuaded," "yield to persuasion." It definitely does not mean to blindly follow orders. The phrase those who are over you in the Lord should simply be "your leaders in the Lord." There is no thought of being "over" anyone, or others being "under" a leader. The authority of a Christian leader is not command authority but servant leadership. A servant has authority, as Jesus said he had, because he awakens by his loving service a desire to comply. Or he is persuasive because of his logic or knowledge. 
Since the verb here is in the middle voice, it implies a willing cooperation on the part of the one instructed. He must be “willing to be persuaded” and then, if persuaded, yield to the persuasion. A brother named Leighton Tebay has well said: “The key difference between obedience to authority and obedience to persuasion is that the person doing the obeying still has the right and the obligation to be discerning.”
Now, to what matters does the persuasion refer here in Hebrews 13:17? The next clause in the verse gives the key: “for they keep watch over your souls as those who will give an account.” The matters here must pertain directly to the spiritual health and growth of the saint since those who are trying to persuade them (the leaders) will give an account to God of their care of the sheep. Most likely these leaders are elders, certainly, although there could be others involved, such as teachers who are not elders. The elders are to be shepherds, charged with the oversight - the activity of watching over the flock for the welfare of the sheep. Their reward is based upon this responsibility and care (1 Pet. 5:1-4). The matters of persuasion here would certainly seem to be key matters of faith and truth which are needed for the spiritual well-being of the souls of the saints. I think we could rule out that the persuasion here, in context, means persuasion concerning decisions like, “should we build a new building,” or “should we start a soup kitchen for the poor.” It would certainly not pertain to personal things in the saints’ lives, unless some clear point of truth and sanctification is definitely involved.
Now, let us look at the slightly broader context of the verse. In Heb. 13:7 we see another reference to the leaders and their guidance to the saints:
(Heb 13:7) Remember those who led you, who spoke the word of God to you; and considering the result of their conduct, imitate their faith.
Clearly here the leading is connected to instruction in the truth and the living of the Christian life. This verse, prior to verse 17, sets the tone for what is the subject of persuasion referred to in verse 17. The subject seems likely to do with the truth and the effect of the truth upon our lives. In fact, the majority of the verses between verse 7 and 17 touch on matters of truth connected to Jesus and the New Covenant way. This brings us to the context of the book of Hebrews. Any good commentary will tell us that this book was written to Jews who had converted to Christianity, accepting Christ as their Messiah. Further, the letter was written to encourage them to be faithful, standing firm in their belief and in their practice of living unto Christ. The background is one where, due to persecution and the pressure from false teachers, these believers were wavering in their new faith and being tempted to going back to the Jewish sacrifices and traditions. The following commentary fits this background into the interpretation of Heb. 13:17:
Apparently the followers, not the leaders (possibly house-church leaders), were wavering in faith and being tempted to withdraw from the worshipping community. The author urges them to be submissive to their leaders. God has raised them up that they might watch out for your souls. This exhortation implies that a certain tension had developed between the two parties, and in light of the preceding context (note v. 9) this would most likely be the readers' allurement to false teaching and legalism (and specifically false teaching that rejected Jesus as Messiah and called for adherence to the Old Covenant). The readers should remember the responsibility that these leaders carry as those who must give account to God. Hence their followers should not make their task more difficult, but should faithfully endure and thus bring joy to the leaders rather than grief! 
The call then to “be persuaded” in context is to be persuaded concerning what the leaders have been teaching concerning Jesus as the promised Messiah, and what accepting that truth means for the living of the believer (no longer being under OT regulations, but going out to Him, outside the camp bearing His reproach).
Another observation would concern the matter of submission in this verse. Some versions show “submit to them,” meaning submit to the elders. Actually the Greek text simply says “submit.” It seems best to me to take the submission as a submission to the persuasion – the truths presented by the leaders. The leaders are certainly interested in the congregation submitting their lives to the truth, but they should not have an expectation of others being under their personal authority, but rather under the authority of Christ (Matt. 20:20-28; 23:8-12; Mk. 10: 35-45; Lk. 22:24-27).
If we can see that this interpretation means being persuaded by leaders as to the truth of God’s word and its direction for our lives, then we should realize that it would be wrong to take this verse and “apply” it to other matters. That is, this verse should not be used as leverage to convince the sheep that they should obey leaders for some matters other than obedience to the truth. It would be wrong, for instance, for someone to use this verse to tell others they should be persuaded by the leaders to adopt a building program or support some other non-truth proposal.
This interpretation does not take away the respect and appreciation we should show true leaders of the assembly (1 Thess. 5:12-13). It should not take away the importance of their counsel to us on any matter. God-given leaders, who should be ahead of us in knowing the Lord and the truth, and who are watching out for our welfare, are important for the church. Yet, this view of Heb. 13:17 should also give us the freedom we have in Christ to live directly unto Him alone as our head, not to any human person (1 Cor. 11:3; 2 Cor. 11:2-3; Eph. 1:22). The honoring of Christ as our direct head is actually supported by this verse. This is true because as we remain teachable in our interaction with godly leaders, willing to be persuaded by them concerning the truth of God’s word and its meaning for our lives, then when we see and accept God’s truth over our lives we actually honor Christ Himself as our head.