How automation with the human element boosts productivity with Tiffany

Find out about the importance of taking action on customer feedback to automate often-used tasks while keeping the human element in play to enable clients to enjoy a quicker response.

Listen to how Tiffany supported more than 22,000 customers with a team of two. She shares this experience in an award-winning customer support team to show ways of getting in front of your users quickly.

In this productivity podcast, you’ll see how automation, such as chatbots, frequently-asked questions and webinars along with self-service provide a fast, succinct customer experience.

You’ll also get productivity tips for remote work, time blocking using the tried-and-tested Pomodoro method, and how our own calendar scheduling tool helps with multiple tasks, including talking to your team.

Finally, whilst automation is the future for a productive workplace, you’ll get solid reasons why the human element is so important for liaising with customers and for getting to know your team when working in far-flung corners of the world.

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Listen to episode 13:


In the episode, “How Automation With The Human Element Boosts Productivity,” we discuss:

  • Different ways of creating content to answer any questions that customers have 
  • How processes such as Trello boards, Slack and the calendar scheduling tool help save time and improve productivity
  • Pinpointing common issues that customers bring up to build out snippets or save replies to respond faster
  • Being proactive and providing videos or articles in the knowledge base to preempt any inquiries to the customer support team
  • The importance of providing automation with heart, with the human element
  • What makes a successful customer onboarding process
  • The role customer education plays in adopting a new software tool
  • Importance of being on top of product changes
  • Using tools to structure your day so nothing gets missed out
  • Why time blocking using tools like the Pomodoro method is useful to get more done
  • Setting better boundaries for work-life balance as a remote worker

Favorite quotes

 We were receiving around 3,000 emails a month just in 2020. We didn't have a chatbot to automate, so we really had to be focused on what the customer was asking. We were able to pinpoint some common issues. From there we were able to build out some snippets or save replies that helped us to respond to those common issues faster. Of course, we still personalized it so they knew that there was a human behind it. But I think that really helped us to be able to more quickly identify issues and then have a more succinct response to the customer.” - Tiffany Darwish

 No one wants to feel like they're talking to a machine, I think of myself as a customer. I'm not someone who contacts support right away. I wanna self-serve. So I Google my question, whatever app or product I'm using, or I'll go on forums. I'll do anything I can really to avoid contacting support. But if I do have to contact support, it's nice to know there's a human behind it and that I'm being dealt with as a person and not just like a customer or a number. I do think automation is the way, but there definitely needs to be that heart or that human element behind it. I also think self-service will continue to grow.” - Tiffany Darwish

Especially for more of our high-touch accounts, we want them to be successful right away. They've made this big company decision to use our tool, so we want them to see that value right away. Part of that is getting everyone trained who's going to be a day-to-day user. That's where that customer education comes in. Of course, we have the knowledge base where they can go and seek their answers, but we'd like to provide them with a step-by-step guide, so they know exactly what they need to do so that everyone can be successful.” - Tiffany Darwish

People might think our tool is simple because it's a scheduling tool. There are a lot of moving pieces and a lot of customization and people come in sometimes asking like a use case, `How do I set this up?’ Or sometimes it's troubleshooting. It gets into the API and webhooks. There are a lot more technical pieces that have to be considered too.” - Tiffany Darwish

I do think remote work is a way of life. It's not a race. I think it's really important to work with a company that trusts you to get the job done. I've seen some companies out there who put keystrokes on their workers. You wouldn't be that productive in an office. There are natural breaks. Someone comes into your office to talk or in your cubicle. You go get coffee. You go to the bathroom. These things happen. Working at home isn't any different. You should have a dedicated workspace, but you have to make allowances. You're human, not a robot.” - Tiffany Darwish

 It's been a crazy couple of years and I think we all just need to give ourselves a break. I feel we have a really big expectation of ourselves. We set it on ourselves, it's nothing external that I need to be producing at the same level I was before the pandemic. Of course, we still wanna be productive, and finding ways like automations and efficiencies in our life can be really helpful with that. But I think we need not be so hard on ourselves because it's been a really emotional time.” - Tiffany Darwish 

Meet today’s guest, Tiffany Darwish

Tiffany Darwish from

Tiffany is a champion when it comes to customer support and customer experience. Planning is her forte. She's planned big meetings and events; managed social media accounts in French and English; and went on to teach English online. Her teaching skills led her to do voluntary work in Kampala, Uganda, working with adults and children.

She’s a firm advocate for automating repetitive tasks - things that customers are often looking for or asking about - so that they are immediately available whenever they are needed. But she is also keen to keep the human element in play. People need to talk to fellow humans.

Tiffany loves creating how-to tutorials and demos to show people how to get the most of the online scheduling tool. She's also great at troubleshooting and making sure things run smoothly.

Now she uses her planning and teaching skills to support customers. Before she helped customers set up accounts and troubleshoot issues. Now she's proactive in supporting customers with live trainings and educational content so they can use the calendar scheduling tool as quickly as possible.  

As Tiffany says: “I love working on small teams that accomplish big things. A customer-focused problem solver. Forward-thinker. Team-player.”

Productivity resources to explore

“How Automation with the Human Element Boosts Productivity,” full transcript

This transcript has been slightly edited for clarity and readability.

Ben (00:00):

This is Get More Done, a podcast, and I'm Ben your host. Thanks for listening. We hope that you are able to learn how to do more with less and help your team level. Up on this episode, I had a chat with the amazing and multidimensional Tiffany Darwish. Tiffany is's own customer education manager. During our conversation, we discussed the importance of frictionless onboarding and how she was able to support over 22,000 customers with a team of two. Enjoy.

Ben (00:40):

So welcome back to Get More Done, the podcast all about productivity and crushing of goals. Today, I'm sitting down with's own Tiffany Darwish, the customer education manager. So Tiffany, great to see your face. And thanks for being on the podcast. 

Tiffany (00:55):

This is a privilege, a little bit scary, but I'm here.

Ben (00:58):

You got it. To break things up, as you hopefully have heard in some other episodes, we usually start with an icebreaker question. So this one for you, what is the animal who is most similar to your personality?

Tiffany (01:18):

No one would be surprised, but I'm a house cat

Ben (01:22):

Why a house cat?

Tiffany (01:24):

I'm really easy to please. People don't believe that about cats, but I just need food and a good place to sleep and a belly rub. And I'll be fine.  

Ben (01:34):

In that order. Yes, yes. I thought you were gonna go the other way and be like, ‘I like to go in a little box in the corner and just hang out. Not be bothered by anybody.’

Tiffany (01:44):

That's also me.

Ben (01:46):

Yeah. Some days. Right. Awesome. Tell us a little bit about your role as the customer education manager with 

Tiffany (01:56):

It's interesting. It's a newly-created role at the company. I got a chance to create my own role. I'm basically responsible for educating customers and helping them to be successful using our tools. The basis of that is our knowledge base creating written content. And now more of an emphasis on video content as people love video. Then, hopefully next year, introduce some webinars and just being more vocal and again, helping people answer any questions they need to be answered.

Ben (02:33):

Yeah, that sounds great. And how have you found the transition from working more in support, more reactive, to this proactive role?  

Tiffany (02:42):

A little bit was strange. Just because when you're in a reactive role, the work just comes to you. In the first couple of months, the adjustment for me was turning on my computer, and ‘Now what do I do?’ But learning to manage my time, manage projects, decide where the priority lies and be able to fully dive in and focus on that. That's been fun. I've been able to talk to customers too with some training sessions and it's good because you get to see our tool in the eyes of the customer. It helps you see, ‘Oh look, that could be a little bit better. Maybe there's some education that needs to be done around that. Or maybe that's something the product team needs to know about.’ So I think that part has been really refreshing as opposed to just responding to emails all day.

Ben (03:35):

You can mold your day and be more autonomous. Have you built out any processes that help you manage that? There is so much for you to do. Have you built anything that helps you save some time with all of that?

Tiffany (03:49):

We used to have a Slack channel where people would put in requests for things that should be in the knowledge base. Now those come into me personally, but I do keep a Trello board and I've got that pinned to every browser I use. I can open that up and be like, ‘Okay, where am I? What was I working on?’ It's really good when you leave on Friday and come back on Monday and ask ‘What's my job?’ I think the Trello board is really helping me manage my time a lot better.

Ben (04 :22):

Yeah. Trello boards for the win, as long as you're staying on top of it. Because then it's just all these cards and you're like, ‘I don't wanna do any of that stuff.’

Tiffany (04:29):

Just keep moving things from ‘doing’ to ‘to do. 

Ben (04:33):

Exactly. Then back to ‘backlog’ and then ‘to do.’ Speaking of processes, previously you were part of the award-winning support team for and, for a while, it was a team of two. You and I were working on that. Can you speak a bit about how you were able to do that with serving 20,000 customers with just a team of two people? How you were leveraging automation and doing more with less, with some examples.

Tiffany (05:02): 

I was just thinking that time was such a blur. I was looking in Help Scout, the tool we use. 

Tiffany Darwish quote 1

Also, we used that as an opportunity to be like, ‘If too many people are asking about this, maybe it needs to be like a frequently-asked question or it needs to be some content in the knowledge base.’

Tiffany (06:00):

Then I would start producing those articles or making a quick video to put in the knowledge base. Another thing that was really useful was when Help Scout introduced messages. We could get in front of users a bit quicker and head off some questions they might have. We started when users were onboarding to a trial account with a popup and giving them a guide on how they could set up their account. Where else did we use it? We're using it now. It's right before the holidays and we've put up a message, ‘Hey, this is how you get your account ready for the holidays.’ Those are ways we are, hopefully reducing the burden on support by being more proactive.

Ben (06:55):

Yeah. Being that proactive to stop people from coming in and I think it was a blur, with you and I just heads down doing that for so long. We'll speak in a bit about more support for support coming in. I think the other component we'll talk about later is getting that information to help improve the tool because you're getting all this feedback from customers. Maybe there's an opportunity to make some changes, make some adjustments for sure. How have you seen support evolve over the last few years? We talked about messaging and chatbots and everything, so maybe look into a crystal ball or be an Oracle, where do you see things going in the future?

Tiffany (07:43):

I definitely see it as automation, but it needs to be automation with heart. 

Tiffany Darwish quote 2

Tiffany (08:36):

We users put the content out there, making it accessible and easy to find for users. That way, anytime anyone's searching anything, they find exactly what they need. I know one of the issues we are running into is that we have certain features that are called something, but that's not what the user might call it. So maybe they're searching and they can't find the answer they need. We need to understand if it’s a product issue or an education issue. Taking that feedback from customers, like, ‘I searched your knowledge base and I couldn't find this.’ We thought it was pretty easy to find so that really helps continually to iterate and improve the process.

Ben (09:23):

Those feedback loops are imperative because, as you've experienced working in the knowledge base, if it's not a helpful article, then no one's gonna be finding value in that. Then they're gonna still reach out with their questions. I'm exactly like you too. I'll avoid reaching out to support just because I can figure this out, and try to do things myself. But making it easy to get in touch with people too, I think that's also important with the messaging and everything there.  

Tiffany (09:51):

I think sometimes, even though you've put in this automation to make it easier for your customer, it becomes like friction. I got locked out of an account. I think it was Zoom, I lost my phone, I got a new phone, and my 2FA [two-factor authentication] codes were lost. I was in this endless loop with a bot telling me, ‘just put in your 2FA,’ and I'm like, ‘I can't.’ It took seven tries just to get to somebody. By then I was exhausted. So, like you said, making it easier to talk to somebody in those situations where they really do need to talk to someone.

Ben (10:32):

How frustrating and be like, ‘I just wanna solve this.’ That's everybody running to support, saying ‘I just need some help.’ So getting to that as quick as possible. I think one thing that also helped us out is the speed at which we were able to get through things because, being with a product for so long, you know it inside and out. You mentioned you're working more with customers and them coming in and doing trainings and more on the onboarding. In your opinion, what makes a successful onboarding process for our customers? How would that look?

Tiffany (11:22):

You know, I just want it to be painless and easy. I think every customer wants to be successful in whatever they've committed to using. I think it's the product's responsibility to pave that way - create an account, click here, you're done. I think for us, as we're focusing as a tool for teams, I think the onboarding process - sign up, invite your team, figure out the booking pages your team needs, connect their calendars, boom, start sharing - I think five steps maximum for any product. I shouldn't have to go to the knowledge base to do a standard step in setting up something in my account.

Ben (12:07):

How are you working with the product team there at to make those changes into the app and get some improvements set up.

Tiffany (12:22):

That's been an exciting part of my role that I really love. I’m like the support now for the product team. I go through the customer feedback that we're getting in the support queue, not just complaints, but people asking, ‘How does this work?’ or ‘How can I accomplish this use case?’ and pinpointing those as points of friction that can be solved directly in the app. I'm giving that feedback directly to the product team. I talk with the head of product TJ on Tuesdays, and then we have a UX debt call with our UX researcher. We use that time to talk about common struggles that users have. They can't find a setting or it was an expectation on how something should work and quick wins on things that can be resolved.

Tiffany (13:21):

For example, we use Markdown for formatting on our booking pages. For the longest time, even when I started, when you clicked on a link, it opened in the same browser. Tat's just not a great experience for the booker because they've filled out a whole booking form of questions. Now they need to read the terms of booking, click on it and Iose all the work. So like surfacing that to the product team and talking about how hard would that be to fix, we were able to get a fix in and we see no problems with that in the support queue now. That's a great result of being that liaison between the two departments.

Ben (14:06):

That collaboration can’t be understated because oftentimes product teams are heads down working on features, or working on functionality. Then them having the opportunity to pull you in and ask your questions and just say, ‘Hey, this is the friction that we're seeing’ and getting light to that is very important. And excited to see what's coming further with that because as that gets tighter and that feedback gets more represented, I think it'll be some awesome changes.  

Tiffany (14:34):

The feedback we get is like a fire hose. So there are so many factors to consider and, of course, we have our own vision of where the product is going, but we're not anything without our customers. Having that conduit of feedback directly from the customer's mouth is so important in informing future decisions.

Ben (15:10):

Let's talk a bit about the customer education piece because you mentioned that frictionless onboarding is the goal. What do you think customer education plays in the adoption of a new software tool?

Tiffany (15:24):

Tiffany Darwish quote 3

That's where our focus is. It's not really like an onboarding role, but it's like, ‘Here are the tools that you need.’ You don't have to go searching for anything. You know, if you follow these steps, then everything is set up. Of course, we're always happy to offer additional training for our segmented customers. There are also times when people are new to the company, it's an existing customer, but someone's taking over as the YouCanBook-me advocate or admin in the company. So of course we wanna get them trained and onboard, using the tool and continuing to be an advocate for us.

Ben (16:38):

Yeah, absolutely. You mentioned earlier about some things you're looking to try out with office hours or some webinars. I think that could play a powerful role in educating more people because, you're only one person, but if you could reach out to more people.

Tiffany (16:56):

I'd love to talk to everybody, but I don't have that much time.  

Tiffany (17:08):

We've been a tool for 10-years strong and no one really knows who we are. So we're getting a chance to develop our personality now and the face behind our tool. I think it's a really big differentiator and people know who is.

Ben (17:27):

I mean that difference between a family-run company, a small group of remote-dedicated people, compared to maybe a larger monolithic, you're just a number, you're part of the bottom line.

Tiffany (17:39):

Exactly. That human element again.

Ben (17:42):

Exactly. It all comes back to that person-to-person connection. Speaking of people and, I guess, partners on the support side, you have outsourced your support and you work with a partner there. Let's speak a bit about that relationship and how that's changed things at

Tiffany (18:01):

I think it's gonna take us to the next level. Working with PartnerHero they've provided us with really quality humans, and they're so eager to learn and they're so eager to help people. They have that love of people and love of customers that is essential when you're working in a support role. I've been really impressed and blown away by them. 


Tiffany Darwish quote 4


The fact that they've been with us just six months so far and the quality of their answers and the speed, I'm just really impressed. I'm excited for the future because I know it's gonna open us up to more avenues of being where our customers want to reach us.

Tiffany (19:04):

I think the future is going to be really bright with PartnerHero honing our support

Ben (19:11):

And potentially expanding to chat support, and more avenues for that. That's really exciting to see. One big question I had for you is what goes into creating and maintaining a good support knowledge base? I know that's your baby and it's now almost at 400 pages, 400 articles, now.

Tiffany (19:32):

Yeah. It's a chubby toddler who needs to go on a diet.

Ben (19:35):

What makes a good knowledge base?

Tiffany (19:43):

Blood, sweat and tears. I think you cannot be satisfied to have a good knowledge base. You can't rest on your laurels. Things are always changing in our product features or even just the look of it is changing. Being on top of those product changes so that our knowledge base is moving in the same direction that our app is. You never wanna go to a knowledge base looking for support. You're like, ‘Well, my account doesn't look anything like that.’ So I think it does require that agility and also the knowledge of the tool and how it works. Creating more specific use case type articles that someone might find and be like, ‘Okay, well now I know works with the hybrid schedule. So let me just follow these steps and I can do that.’ Knowing the ins and outs of the product and then just staying on top of Slack in Jira so that I'm like, ‘This change is about to go out. I can put that on my Trello board. Be ready to change the article too.

Ben (20:56):

How do you manage all of that? You have all of these alerts coming in. How do you structure your day to make sure you're not missing anything? 

Tiffany (21:05):

Well as a calendar scheduling tool, I rely on my calendar. I block out time on my calendar. Because we work with a European team, I try to schedule out some time to actually talk to my team in the mornings. But then I have blocks of time in the afternoon that I can really focus on work. I've discovered that really works for me. So when Slacks come in I add them to my Trello board. Then in the afternoon I'm, ‘Okay, these are the five I'm working on today.’

Ben (21:40):

And when we're done with this call, maybe I'll help you get some automation set up to make it even easier for me.  

Tiffany (21:51):

Yes, please. You automate my life then.

Ben (21:54):

One section at a time. When you are doing this deep work, do you ever just bump to music? Do you do music or anything?

Tiffany (22:03):

I'm not gonna tell you  I'm just playing Adele all day, every day.

Tiffany (22:11):

Actually there's some music from a Turkish TV show that I watch. It's very instrumental and sometimes it just makes you very emotional, but I will play that low in the background sometimes.  

Ben (22:28):

I found that I can't even listen to a podcast while I'm doing something else because then I'm, ‘Oh, that's interesting. Let me go look that up.’ Then it's, ‘No, you need to focus and do this thing.’ Any other productivity tips or hacks or anything that you abide by that's really made a big impact on you?

Tiffany (22:51):

At the suggestion of Danita, one of our colleagues, I've gotten a Pomodoro browser extension. First of all, 25 or 45 minutes go by so fast when you turn off all your notifications. That is really helpful too. If you set a time and you mute everything, and you just really have that time to focus. I feel really inspired. I have a chance to be creative and really do some deep thinking or planning. For me, just turning off notifications - and I think I heard that in Bridget's podcast - is, ‘Just turn it off and nothing's on fire, it will be fine.’

Ben (23:44):

The Pomodoro method, which maybe some people aren't familiar with, is basically time blocking.  

Tiffany (23:53):

You're saying, ‘I'm doing this one task for a certain amount of time’ and you say 20 minutes to 45 minutes, that's like your sweet spot. That's been working for you. I'll do this task, updating these docs is gonna take me 45 minutes. I'll set the timer. Maybe it takes me longer. Maybe the timer goes off and I wasn't finished. Then I have a chance to set it again or take a break, stand up, walk around my house, which sometimes I forget to do. Then I'm ready for another 20-minute block. Having that time measurement instead of just saying, ‘Okay, today I'm gonna work on that.’ If you don't carve out the time, it will never come.  

Ben (24:37):

Then it just starts piling up and then you don't wanna do any of that. I'll have to check out that browser. I had one that somebody else recommended. It alerts you when it's been an hour, so stand up and stretch your legs. You've been working remotely for a while now. What are some tips for people who may be new to this remote work or getting a bit tired of working remotely, if they were working in an office before?

Tiffany (25:15):

Tiffany Darwish quote 5


And I think for me, one of the most important things was creating an office space for myself. When I lived with my parents at home, I worked in my bedroom. I had a desk, but it was right next to my bed. The lines between the bedroom and office got very blurred. I think having a separate space where I can close the computer, close the door and I'm off work now. That has helped me set a lot of better boundaries for my work-life balance.

Ben (26:36):

Having that separate space where you can shut things down and not have them bleed into the rest of your life. Before this, we talked a bit about when you're working remotely, people don't think that you're actually working and they wanna interrupt you. How do you try to limit those types of interruptions?

Tiffany (26:54):

I usually put, ‘Do not disturb’ on my phone, especially during meetings or video calls so that I'm not distracted by outside things. And it's been years of training. I've been remote, I think, for seven years. And so training my parents that just because I'm home doesn't mean I'm not at work.  

Ben (27:22):

Anything else that you wanna talk about or you wanna highlight anything that you think our listeners would want to hear? 

Tiffany (27:48):

Tiffany Darwish quote 6


I know people who are really excited to be with family this year and now a new variance is coming along and knocking us for a loop once again. So yeah. Be kind to yourself.  

Ben (28:38):

Exactly. And be patient as well. That's the thing I'm starting to learn about this productivity world is that doing less even could be doing more and going slower to go faster. All of that and avoiding meetings too, and not just saying, ‘I'm booked solid.’ You need time for yourself. Taking care of yourself is important too because that's the foundation of everything. It all comes full circle and everybody needs to take their hand, put it over and give a nice pat on the back, we're all doing great, we're all gonna make it.

Tiffany (29:10):

One of the things we did this year as a company was this booking page for all of the team members where you could book a 15-minute chat just to say, ‘Hey,’ because we haven't had a chance to meet together in person. At the beginning, I felt a little guilty. This is not a call about work but sometimes productivity is not about work, but feeling comfortable in work, knowing who you are, who you work with, and who your colleagues are. We've hired a bunch of people this year and I realize, because we haven't met in person, I haven't had a chance to even say ‘Hi.’ You get busy on Slack and there are so many notifications, so being able to just jump on Zoom and say, ‘Hey, how are you? Tell me about where you live? What's your village like? What do you like to do for fun?’ All of those things have been fun.

Ben (30:07):

That ‘anything but work’ page is really great. And it's a nice way to connect because I think we lose that in a remote environment. In an office there are spontaneous coffee visits or spontaneous lunches, or a chat whereas in the remote side you almost feel like you're barging in on somebody because they're focused and their head is down doing their thing. You're like, ‘I just wanna talk and hang out.’ Now you have the excuse to do that. I don't know about your calls, but mine are never 15 minutes. They always bleed over. You don't want the call to end. Which is a good sign that we're working with some great people.

Tiffany (30:42):

We really are. I can't wait until one day when we finally get back in person.

Ben (30:45):

One day. It'll be great to see everybody. The last question for you. You talked about the new trainings you're gonna be doing and the virtual stuff, what's next outside of that for you? What are you excited about? 

Tiffany (31:03):

I'm excited for the future of our product. For a tool that's been around 10 years, I feel like we're just getting started. I'm really excited to strengthen this relationship between customer and product. Working more closely with the US researcher and honing all of this feedback - taking it from a fire hose to a garden hose - and letting that really inform the future of our tool so we are making a tool we're proud of, but also like that our customers are proud of. So I'm really looking forward to 2020. I think it's gonna be the year of product.

Ben (31:45):

Yes. 2022 would be an amazing year. 2021 was an amazing year. It's all gonna be amazing. I love that focus on removing that friction and prioritizing that, and making product improvements. I'm excited for that too. I'm a little biased, but super awesome. Tiffany Darwish, it was a pleasure to speak with you.

Tiffany (32:10):

Thank you for having me. This was really fun.

Ben (32:13):

Thank you so much for being on Get More Done. I hope you have a good rest of the month. Take care. Thank you.

Tiffany (32:22):

See you.

Ben (32:23):

All right. Bye. We appreciate you listening to Get More Done. Be sure to subscribe on your favorite platform and feel free to leave a review. Also share this episode with anyone in your network that may benefit from the conversation. If you or someone you know, would like to be a guest, please reach out to, visit, reach out to us on Twitter @YouCanBookMe or visit us on the forum I'd love to hear your feedback, catch you on the next episode.


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