If you send out contracts, NDAs, or any document that needs a signature, you know the pain of waiting for people to sign. Sometimes it feels like your documents have fallen into a black hole. If you're using Hellosign (now called Dropbox Sign, but most folks still call it Hellosign), this guide is for you. I’ll walk you through tracking document status and nudging those slow signers—without overcomplicating things or wasting your time.
No fluff, no sales pitch. Just clear steps and a few honest takes on what actually helps.
Why Tracking and Reminders Matter
Before we dive in, here’s the hard truth: most delays in getting things signed come down to two things—people forgetting or not realizing it’s urgent. Tracking and reminders don’t solve everything, but they do cut down on the “Oh, I missed that email” excuses.
If you’re dealing with sensitive timelines, contracts, or just trying to keep business moving, learning to use the Hellosign dashboard well is a real time-saver.
Step 1: Log Into Your Hellosign Dashboard
This part’s obvious, but let's get it out of the way:
- Go to the Hellosign website and sign in.
- If your company uses SSO, use that. Otherwise, just email and password.
- You’ll land on your main dashboard. If not, click “Documents” in the sidebar.
Pro tip: Bookmark the dashboard. You’ll come back here more than you think.
Step 2: Understand the Document Statuses
Once you’re in, you’ll see a list of your documents. Hellosign uses simple labels that actually mean something (for once):
- Awaiting Signature: Someone still needs to sign. This is your main focus.
- Signed: All done. You can download or archive these.
- Declined: Someone rejected the request. Time for a phone call, probably.
- Expired: The signing window closed. You’ll need to resend.
- Draft: You started, but didn’t send it yet.
Don’t waste time tracking “Draft” or “Signed” docs unless you’re chasing up records. Focus on “Awaiting Signature” and “Expired.”
Step 3: Find the Documents That Need Attention
Here’s how to zero in on what matters:
- Filter by Status: Use the filters at the top or side of your dashboard. Set it to “Awaiting Signature.”
- Sort by Date: Click the “Date Sent” or “Last Updated” column. Oldest pending docs should be at the top.
- Search by Name or Email: If you’ve got a lot of documents, use the search bar. Type the signer’s name, email, or doc title.
What to ignore: Don’t get distracted by the analytics or “completion time” metrics for now. Focus on what still needs action.
Step 4: Drill Into Each Document’s Details
Click any document in the “Awaiting Signature” list. You’ll see a breakdown:
- Who’s signed, who hasn’t: Each signer gets a status (signed, viewed, not opened).
- Timestamps: You can see exactly when each action happened.
- Signer’s email: Double-check for typos if someone claims they never got it.
This view tells you if someone’s opened but not signed (they’re procrastinating), or never opened it (maybe your email got spammed).
Honest take: Don’t overthink if someone’s “viewed” but not “signed.” People get busy, or maybe they’re waiting for legal to review. But if the doc is untouched for days, it’s nudge time.
Step 5: Send a Reminder to Slow Signers
Here’s the part that actually moves things along. Hellosign lets you send reminders, and it’s dead simple:
- Open the document’s details as above.
- Find the signer who hasn’t signed yet.
- Click the “Remind” button next to their name.
You can usually customize the message (but honestly, keep it short and polite—nobody likes a nag). Hellosign sends the reminder email right away.
Pro tips: - Don’t spam reminders. Once every couple days is fine. Any more, and people start ignoring you. - If someone’s ignoring multiple reminders, pick up the phone or send a direct email. Sometimes automated emails land in spam or get tuned out. - If you’re dealing with a big group, prioritize the bottleneck. Hellosign follows the signing order: if Signer 1 hasn’t signed, Signer 2 can’t.
Step 6: Set Up Automatic Reminders (If You Want)
If you’re in this for the long haul, you can automate reminders:
- When sending a document: There’s usually an option to “Automatically remind signers.”
- You can set the frequency (e.g., every 3 days).
- This is an account or document-level setting—double-check your defaults.
Reality check: Automatic reminders are handy, but not foolproof. Some people tune out anything automated. It’s a set-and-forget feature, but don’t expect miracles.
Step 7: Deal with Expired or Problem Documents
Sometimes, a document expires before everyone signs. When that happens:
- The status will change to “Expired.”
- You can’t revive it—just duplicate the document and resend.
- When you resend, check the signer’s email address and maybe give them a heads-up first.
If someone declines to sign, you’ll get a “Declined” status and usually a reason (not always helpful). At that point, you need to talk to them directly.
Step 8: Download Audit Trails and Records
For compliance, audits, or just good recordkeeping, you might need a paper trail.
- Download the signed document: Click into any “Signed” doc and look for the download button.
- Download the audit trail/certificate: Hellosign attaches a log showing who signed when, IP addresses, etc. This is your proof if anyone challenges the signature.
Honest take: Most people don’t need the audit trail unless you’re in legal, HR, or finance. But it’s there if you ever get pushback.
What Works, What Doesn’t, and What to Ignore
What works: - Checking the dashboard every few days. It’s a good habit. - Sending reminders politely and sparingly. - Following up personally if a doc is stuck.
What doesn’t: - Assuming automated reminders will solve everything. Some folks just need a human nudge. - Chasing down every analytic in the dashboard. Focus on what’s unsigned. - Blaming Hellosign for delays—most of the time, it’s people, not tech.
What to ignore: - Fancy analytics unless your boss needs a report. - Unused features. There are a lot, but most people just need send, track, and remind.
Quick Troubleshooting
- Signer says they didn’t get the email: Double-check their address, ask them to look in spam, or resend.
- Document is stuck for days: Call or email the signer directly.
- Need to resend: Duplicate the document and try again.
- Can’t find a document: Use the search bar—sometimes it’s just a typo in the title.
Keep It Simple and Iterate
You don’t need to master every feature to get your documents signed and tracked. Bookmark your dashboard, check it regularly, and send reminders politely. If something’s not working, adjust your reminder timing or follow up personally.
Remember: the tool’s only as good as the habits you build around it. Start simple, and tweak as you go. You’ll spend less time chasing signatures and more time getting actual work done.