Help Scout vs Outlook

We use Help Scout for sales, customer support, admin, receipts (e.g. we forward all of our receipts into an inbox), invoicing, and even recruitment. We've been using Help Scout for over 5 years and we love it!

Help Scout can be best described as a customer-centric tool. They have done an incredible job at building somewhat of a community around their software. For example, when I see a company is using Help Scout (on either the website chat or email response), I have an immediate reaction of feeling that they care deeply about customer support and will have equally caring support reps.

I'm also part of their "Support Driven" Slack community as well and am regularly seeing teams of all sizes (big and small) actually switching over to Help Scout from Zendesk, Intercom, and Front, amongst others.

They have a nice implementation of live chat in their product, as it's actually thoughtful (and further customer-focused). How you might ask? Expectations matching. For one, you have to mindfully to mark yourself as "available", and if you aren't actively in Help Scout for a long enough period of time, it will automatically mark you as "away" (wait that's a feature...? hold on, let me explain).

There's nothing worse than having a "live chat" on your website that gives the impression that you'll get an immediate response, but in reality, you just get a bot that asks for your email address because "the team is away". It's a bad expectation mismatch. Help Scout doesn't allow this to happen.

They have more of an "email first" approach, with a "we might be live though" as a secondary. So when the live chat shows on your website, you can be sure that there's actually a human on the other end. Great expectation matching, which as a small team, I appreciate a lot. Now take that, versus Intercom, which simply upon seeing the logo, you and everyone else expects to speak to someone immediately, and if you aren't on the other end, they get frustrated - you're set up to lose versus surprise and delight (which is what Help Scout constantly allows for). If you're a small or mid-size team, why not set yourself up for success and delight out of the box?

One of the areas that got me obsessed with Help Scout many years back was their robust workflows functionality. You can set up either automatic or manual workflows. Automatic is great when you can set up some type of consistent trigger, like when a due date is today and the conversation is active or pending, then mark it active, set the priority custom field to P1, and add the tag "due":

Pair this with the API and you can trigger some pretty powerful workflows both inside and outside of Help Scout.

Help Scout has gone a human-centric approach to AI (unsurprisingly, as it's true to brand). What they've done is things like, automatic summarization of chat threads. So if you're jumping in and out of threads and collaborating with team members on a daily basis, it'll help you get back up to speed, without having to read the entire conversation thread:

We for one appreciate how Help Scout has handled their approach to AI, as when comparing Help Scout to Intercom for example, Intercom tries to rope in AI at every corner, in chat, and trying to automate conversation threads. While this is cool in theory, it does feel a bit like we're back in the "you must first talk to a bot before talking to a human" time period, which still is a bit frustrating. I'm sure Help Scout will do more in this area as AI continues to evolve in time.

Help Scout also has some pretty cool AI assist features coming to the actual compose window, pulling the likes of ChatGPT directly where you're actually responding to messages:

The thing is, the app is a bit buggy from time to time. You can accomplish most of what you'd like to do on-the-go, the thing is, it's missing some core features like the "workflows" functionality. This means, if you rely heavily on workflows when using Help Scout, you're going to be a bit frustrated when on mobile. I'll admit, I've definitely visited the desktop app on my phone every now-and-again to run a quick workflow 😅

On the plus side, the have an iOS and Android app, and both have similar feature-parity. It really just needs that final 20% added to the mobile app to make it great.

If you're a larger enterprise, you're likely using Outlook instead of Gmail (Google Workspace) to manage your email and calendar for work.

That said, most startups and quickly growing companies use Google Workspace, so if you're looking into Gmail vs Outlook, we believe Gmail is the clear winner here. It just has a more user-friendly experience all-around, and has significantly more integrated tools ( most modern tools integrate with Gmail over Outlook).

If you're "stuck" with Outlook and want to make your email experience 10X better, using Outlook in addition to a platform like Superhuman email is the way to go.

• All-in-one email and calendar solution within Microsoft 365
• Tight integration with other Microsoft tools
• Familiar interface for long-time enterprise users
• Standard choice for companies already committed to Microsoft

• Clunkier user experience compared to modern email clients
• Fewer modern integrations compared to Google Workspace
• Limited “Sign in with Microsoft” support across newer SaaS tools
• Most modern startups and tools prioritize Google compatibility
• Rarely a proactive choice for small business owners

Outlook combines your inbox and calendar into a single interface. Giving you the ability to respond to your emails, check calendar availability, schedule a meeting, and send out invites, without switching tools.

For companies already using Microsoft 365, you know it works and that it’s functional. You also know it lacks that modern feel that places importance on speed and focus.

Outlook connects directly with the rest of the Microsoft ecosystem (Word, Excel, Teams, SharePoint, and OneDrive). And that's great if 365 is what you're committed to, but when you're looking to create a tech stack outside of their system, it suddenly becomes a lot less compelling.

Large enterprises rely on the level of oversight that Microsoft provides. It provides strong security, compliance features, and centralized admin controls, but this is a great example of just because flagship companies are using it doesn't mean it's what's best for you and your team.

If your team is a smaller and fast-moving team, this level of complexity will probably feel like overkill.

Outlook itself is included with Microsoft 365, and pricing varies depending on features and region. Most Microsoft 365 plans start around:

• Business Basic: ~$6/user/month
• Business Standard: ~$12.50/user/month
• Business Premium: ~$22/user/month