Putting Siri AI to the Test
A couple of years ago, Apple promised us a lot. They showed how powerful Siri could be. Siri would understand you, know what was on your phone, and help you get things done. Then that promise went unfulfilled for two years. This past June, Apple announced iOS 27 and promised again that Siri would be much better.
The new Siri AI has now been out for a little over a month. Plenty of reviewers and YouTubers are saying the same thing: Siri doesn't suck anymore.
So I put that to the test. How does it compare, and is it really useful now?
Here is the short answer. Siri is absolutely better. It understands you in the context of what is on your phone. Ask about something in your email, and it finds it. Ask what is on your calendar, and it helps you make sense of your day. Ask, "What was that conversation I had with Charlie the other day?" and it pulls it up. General knowledge questions are far better than they used to be, too. That is helpful, and it is fun. But can the new Siri help you be more productive? I think the answer is yes. A lot depends on how you use your devices and what your work looks like.
The Windows Problem
Many leaders, especially in retail, carry an iPhone for email and texts. But much of their real work happens on a Windows laptop the company provides. Those two worlds don't connect well. Siri can't see what you do on your Windows machine.
Email is a good example. If your Outlook email is set up in the Apple Mail app, Siri can see it. If your company makes you use the Outlook app on your phone, Siri probably won't see that information. You lose some of the value, so look at your own setup before you decide.
Siri Is No Longer the Only Option
Two years ago, an assistant that pulled all your information together was new. Most people had never seen it at scale. Today, it is much easier to connect tools like Google Gemini, Claude, or ChatGPT to your email, calendar, and notes. These tools are very good at pulling that information together when you give them access. So what Siri offers is no longer unique. It is one more good option. Where Apple stands apart is privacy and security. Apple keeps putting privacy and data protection at the center of its AI work. For many leaders, that should weigh heavily in the decision.
Those are good to know starting points, but I really wanted to understand how it works in real-world use cases. To see how Siri holds up in real life, I tested a few common things a leader might use AI for.
What I Tested
1 - Finding Past Emails
I asked Siri, "When was the last time I emailed Bobby?" It found the emails, told me when they were sent, and summed up what we talked about. This is great when you know you emailed someone a week or two ago but can't find the message. One catch: your email accounts need to be set up in Apple Mail.
2 - Dictating Emails in the Car
Driving between stores is a good time to get ahead of email. Siri is one of the better tools I've used for this. Talk the way you want the email to read, then ask Siri to clean it up and fix the grammar. It can add the recipient and the subject line, then save it to your drafts folder.
When you get to your desk or your next store, read it one more time, make small edits, and send. You skip the retyping and save a lot of time. You can start setting up a meeting this way, too. Siri can't see other people's calendars, especially in an Outlook setup, but you can line up the details for when you're back at your computer.
3 - Tracking Who Replied
Let’s say you send an email your team, or a group of stores (as a District Manager). You can ask Siri who has replied and who hasn't. In my limited testing, it kept track well. There is some risk. If you've sent several similar emails over time, Siri may mix up which reply goes with which email. The clearer your request, the better your results. You can also ask Siri to turn the results into a list. If you use another AI tool, you could take that list and build a spreadsheet to track replies over time.
4 - Pulling Photos by Location
Siri did this very well. Ask it to find pictures from a place you visited weeks or even months ago, and it pulls them up. You can be as specific as you need, using a city or an address. A district manager might even teach it which store numbers match which locations.
Then it can take the next step. I asked Siri to pull the pictures from my time in Cleveland and email them to someone with a short note. It found the photos, attached them, addressed the email, and drafted the message. You can send it right away or save it as a draft to review later.
5 - Voice Notes to Reminders and Calendar
Record a quick voice note and have Siri add it to Apple Reminders or your calendar. Siri is much better now at putting items on the right list. The more specific you are with list names, the better it works.
6 - Recalling Text Conversations
Apple showed this one in its keynote. Ask Siri about a text conversation with someone, and it finds the messages. It tells you when you last texted, sums up the conversation, and points out what you need to follow up on. This helps when you promised someone something but can't remember what.
7 - An End-of-Day Summary
Ask Siri for an end-of-day update. What are the most important emails I need to get to? What's on my calendar tomorrow? What do I need to prepare for? Siri pulls it all together. You can take this further. Ask Siri to help you build a Shortcut that runs this summary. Then just say, "Run my end-of-day shortcut." It's a one-time setup with a long-term payoff.
Where Siri Stands Today
Siri now does all of these things, and does them well and consistently. That is a big improvement. It isn't as groundbreaking as it would have been two years ago. But Apple has stepped up its game, and Siri is now on par with many other tools.
It still has a ways to go. Because Siri lives on your device, it will see more over time. As Apple and other developers work together, Siri will be able to look across more apps, including third-party calendar, email, and social media apps. That gives it more context about who you work with and what you're doing.
One tip: like other AI tools, Siri works better when it knows you. Take some time to tell it who you are, what you do, and who the key people in your life are. If your contacts list your spouse and children, Siri already knows them. Just say, "Text my wife," and it knows who you mean.
The Verdict…
So, is Siri AI good? Yes. It's a useful tool that leaders should consider, especially if you haven't set up another AI tool to do this work for you. You can get real work done. You can update calendar invites. You can set reminders about people you need to call. You can pull up information stored on your phone when you need it. One of the most useful things I found was pulling photos from a specific location and attaching them to an email, all through a voice conversation with my phone.
Think about the places in your day where that kind of help adds up. Siri can work in the background while you focus on other things. It can make you more productive at the start of your day, at the end of your day, and in the open moments in between.
Have you used the new Siri? How is it working for you?
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