Undock: The Artificial Intelligence You Need In Your Calendar With Nash Ahmed

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TBT 140 | Undock

Are you an absentee founder or working for one? Does it feel like there’s a barrier between founder and employee in your company? Is it difficult to have that line of communication? If you are well familiar with these issues, then this episode is perfect for you. Penny Zenker sits down with Nash Ahmed, the founder and CEO of Undock—an artificial intelligence that enables a meeting platform built for the future of work. Here, Nash shares how not to waste your time, whether as founder or employee, by solving availability problems through calendars. He also talks about the systems he put in place to make sure he is keeping people happy while getting work done and more. Join in on this conversation as Nash shows you a tool that can help you take back your time.

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Undock: The Artificial Intelligence You Need In Your Calendar With Nash Ahmed

I’m always looking for people to give us new perspectives, new tools and new ways to approach how we show up for our time because at the end of the day, it’s not just what we do. We need good tips and strategies on making sure we’re doing the right things, but it’s also how we show up for our time. I’m excited to have Nash Ahmed with us. He’s the Founder and CEO of Undock. He’s a serial Telecom Executive. Undock is an artificial intelligence, enabling a meeting platform built for the future of work. We’re going to see how that fits in and how that differentiates. I’m excited because I’m a techie kind of person in the way that I love innovation, new technology, and seeing where we should be one step ahead. That’s what you’re bringing us, Nash.
Thank you for having me, Penny.
Nash, tell us your story. Why are you passionate about the future of booking meetings? It doesn’t sound telecom to me if you come from telecoms.
We got into meetings accidentally. I started Undock a couple of years back and I was trying to solve my issue with availability in a general sense. Mainly, I was running a few companies at the same time and they were all small businesses. I was the bottleneck for everything. Everyone demanded my time, then multiply by three. There was a 5-person company, 18-person company, and another company that started that went quickly from 3 to 21 as well. My employees and associates getting time with me were difficult. That was a complaint they always had. I labeled it earlier in 2020. The term I label it for is called the absentee founder. You’re there and you’re always working, but nobody feels like they can talk to you.
I was in the thick of that and it reached a peak. Earlier in that year, I was running a project and I was getting upwards of 150 phone calls inbound per day. That’s when I started thinking about, “There’s got to be a better way for these 150 calls to happen where I’m not getting seventeen of them at once, and then 30 minutes with no phone calls. Later in 2020, I’m sitting in my office, I’m on a call and I have another call holding, which is a typical situation and then there was a line of employees outside of my door. When you start to see that, you’ve got a process problem and efficiency problem. I’m wasting their time. Everyone and various key users are waiting to talk to me. I need to figure that out. I need to fix that real-time situation.
Also, real fast because that’s a lot of money being thrown out the window.
I started to build a product that was supposed to be a physical product within my office. I called it the presence pod and it was going to show my employees when is a good time to come by my office instead of waiting by the door.
It pops up and says, “Here’s my next availability,” kind of thing?
It’s the same as an on-air light, but a little more tightly integrated with the phone system, the calendar, project management. It’s a big “do not disturb or please disturb me” indication system. I started to do that and I said, “It would be pretty cool if I did this online because then they can do it even if they’re not in the office. It’d be even cooler if I could do it for everyone.” Why doesn’t this system exist for the entire world? It doesn’t mean everybody has access to what you’re doing or where are you going? If I’m about to call you, I should know if you’re busy. I won’t waste my time and I won’t waste your time. We started working on that product and that’s when we landed in the wonderful world of meetings because I see solving your real-time availability is the last mile problem of availability, and then solving your availability in the future, which is calendaring is a slightly easier problem.
I said, “How can I take some of these principles of this product that I’m building for real-time availability and move it into the calendaring space?” Once I did that, light bulbs went off, but lightning sparks everywhere, “This is it. This is the product that people needed.” We’re still going to build the whole stack of availability, but we’re starting in calendaring. What do we do? We show people instantly when you’re free and when the other person is free based off on your preferences, availability, and scheduling behavior. We don’t do calendar sharing and we do have booking pages, but you don’t even need the booking page. It works directly inline in your email like auto-complete. You’re typing and you say, “Penny, let’s meet,” and you’ll see some suggestions that work for both of us. That is Undock in its first instance there.
You’re the bottleneck. Let’s back up and talk about the entrepreneur’s challenges, some of your challenges, what it solves and what it doesn’t solve. Sometimes people think, “There’s a tool and it’s going to solve all my problems. I make my breakfast.” The truth is it’s going to solve a piece of that. What problem is it not solving that you had? If you had people out the line, you had telephone calls coming in, what problem was it not yet solving that you still needed to solve?
It’s not removing me from being the bottleneck. I’m still the bottleneck. It’s taking that 15, 20, 30 minutes to an hour per day of this ambiguity about when they’re going to have a chance to meet with me and removing it from everyone’s mind. We call it the logistical nightmare is gone.
Artificial intelligence in the calendar to help you better schedule meetings based on priority. Genius! Share on X It saves people time, they’re not waiting in line for you. They’re not waiting on hold for you.
They are not sending emails back and forth, or pinging me on various Slack channels saying, “When can you?” That whole “when are you free?” deliberation is minimized severely with Undock, especially when you’re talking about something that’s later today, tomorrow or a week into the future.
Let’s think about into that. I need to make a meeting with you. I say, “When is a good time?” The system goes away and it doesn’t contact you. It coordinates with your calendar, comes back and says, “Unfortunately, Nash isn’t available for the next week.” If you’re that busy, do you have to allocate some specific times and say, “These are my open-door hours, fill in time according to this block?”
You are a little bit psychic because that is the next portion of our product that’s launching in January 2021. It’s an office hours portion of scheduling. The idea is you have a schedule and you’re either going to keep it, which most people in positions like mine have to do, or you’re going to bust it in one way. If there are slots that work for whoever is trying to meet with me, they can take them. We prioritize these slots based off of my preferences and schedule. I’ll say, “I’m willing to take meetings from 8:00 AM to 7:00 PM.” That’s real. I prefer to have my meetings between 10:00 AM and 1:00 PM or 10:00 AM and 4:00 PM is what I put on there because I like the focus in the morning. I’m not very good conversationally later on in the day. I start to lose my wits.
What the algorithm will do is it’ll find the best suggestion based off of both of your availabilities. Now, if you’re both not available at any time overlapping in the week, what we can do with the magic of Undock is I can go in and say, “Nash has a meeting with David who’s also in the company today at 2:00 PM, but Penny is also free today at 2:00 PM. Let me move that internal meeting to another slot because I know it’s a low priority meeting and then let Penny have her meeting at this time.” This is the key about our product. It’s not a replacement calendaring tools like, “Here’s a booking page. You go do that,” or there’s a bot that’s like, “Go talk to my bot and go figure that out.”
That’s not what this is. This is giving you as much information as possible to reduce that back-and-forth time that you were going or about to partake in with the 1, 2, 3, 4, 5, 7, 8, 9, 10 people that you’re trying to meet with. You’re always in control of this tool, and it’s surfacing as much powerful data to tell you, “Your likely best bet for this meeting time is tomorrow 2:00 PM. If that doesn’t work, there’s Thursday at 10:00 AM. If that doesn’t work, there’s Friday at 11:00.”
I like the fact that you’re telling me that there’s a priority system built-in. I can go in and I can say, “This is a low priority. This is a high priority.” If it’s the client, it’s nonmovable. That’s cool.
We can do that algorithmically before you even make this hard code suggestions yourself. It’s powerful what it can do.
I like that because that’s where the challenge comes in. What I’m understanding is that the calendar tools that you go on and you say, “I’m going to book a call with Penny and she has times available at 10:00 or 11:00.” They might say if it’s a match or not, but it doesn’t take some action to prioritize and move things around so that meetings can take place. That’s a huge advantage to you because otherwise, you wouldn’t be available.
Even with that, the existing pages aren’t dynamic. If I have a busy day tomorrow and on Wednesday, and I have next to nothing on Thursday, when you land on our booking page, just for you guys to have a fifteen-minute slot tomorrow, which is my only slot. It doesn’t mean I want to take that meeting. It takes those things into account, and it’s constantly doing it. These are the things that you are already doing, or particularly this is not a replacement for an assistant. It’s all the things that your assistant is factoring in as well, but they have to keep it all in their mind or in spreadsheets, or they start putting holds and rules directly on the calendar. It’s hard to manage it that way. That’s why we implement a smart AI in our scheduling.
I’m not 100% sure that I understand it. I love that this is the AI that’s integrating. You’re saying it doesn’t replace the admin assistant or the calendar pages. Are you saying it fits in with them? Do you still use them?

TBT 140 | Undock

Undock: With Undock, AI is not there to be that nuance and understand everything to be able to remove a human from the loop.

You can use them if you’d like, but you don’t need to. An administrative assistant, if they’re spending ten hours per week for scheduling his or her boss’ calendar, they’ll probably do it in an hour with that.
They can be freed up to do other more important things as well.
That’s where a lot of other applications fell down to promising that. AI is not there to be that nuance and understand everything to be able to remove a human from the loop. We’re not trying to do that. This is a tool that you can use all the time, and it’s a tool that your assistant can use all the time in all scenarios.
Managing several companies at once is one of those things if you ever want to get something done, you give it to somebody who’s busy. You’ve got to be good at managing your time and whatever, and you spoke about fifteen minutes slots. I’m picking your brain a little bit. This is called Take Back Time. We want to hear about your tool, but we also want to hear about some of your time management practices. I know Elon Musk and a lot of people talk about looking at their day in minutes versus in hours. Is that how you approach your day?
It used to be. Even dating back to college, which I don’t know why I thought I needed to make a spreadsheet. Calendar wasn’t powerful enough, so I made a spreadsheet for my day. I would break it down into blocks. I want to know how much time of my day I was devoting to a certain category of activity and spreadsheets were good for that. My calendar was completely a messages in terms of the quantity of meetings, not in how long it took me to schedule. I haven’t thought about scheduling meetings in a year and a half. No matter which way they’re coming from, if somebody is asking me or if I’m presenting to someone, somebody sends me but it doesn’t matter. I have Undock for that. Now I’m in the mode.
I had a coach told me that, “Whatever it is you’re trying to do for the quarter, make sure your calendar reflects that and do calendar audits.” This quarter I am heads down in product. I’m trying to have fewer better meetings. As soon as I finished fundraising, I went into Undock, turned my dials all the way down. While I was fundraising, I had meetings from 8:00 AM to 8:00 PM. I had Saturday slots and Sunday slots. If an investor wants to meet, I am free. I’m past that phase now. Now I turned the dial down and I kept some of the same windows, but then I blocked out some spaces like Monday morning is game room time. No meetings Monday morning. Friday afternoon is recap time. I have no meetings Friday after 2:00 PM. I took out a little block of Wednesday towards the end of the day.
I set my max meetings to four hours per day. I don’t have to think about this at all, either when I’m using the tool or when somebody else is using the tool to meet with me. All I know is that it will never suggest a meeting if I already have four hours of meetings on that day. Even if I have 3.5 hours it’ll say, “You have 3.5 hours.” It’s not going to tell me this. It’s going to show me a suggestion for the next day. I can schedule meetings with as many people as I want, which I’m trying to keep down, and they’ll still keep it under the four hours. For me, it’s more about the total volume of time taken away from deep work, than it is about whether there are 15 or 30 or 60-minute increments. However, my preference is shorter meetings. Most of my meetings, I’m like, “After fifteen minutes, we don’t need to be here anymore.”
It’s the Parkinson’s Law. You’ll use whatever time is allotted. If you have 15 minutes for a 30-minute meeting, you’ll accomplish what you need to with a lot less chitchat.
There’s a lot more in the platform that helps you with that. There’s meeting agenda, discussion topics, and all those things so you can power through your meetings. If you’re done just move on. I do prefer shorter meetings but in general, I’m on the fewer better meetings kick. There’s not a day on my calendar with more than four hours of meetings.
That’s an important thing for the readers. It’s about the tool, but it’s about the principles that you set. That’s why I asked you about minutes. It’s shorter and fewer meetings so that you can stay focused on what’s most important. I suggest that people go into a meeting audit and see we have far too many meetings that don’t accomplish anything, or we could accomplish the same thing with a status email to everybody, or a quick video to give everyone an update.
That is something that we need to take a look at. I love the fact that you can say, “This is how many meetings and how many hours I’m willing to take away from the other focus work that I need to do.” It takes it out of your head. You don’t need to think about it anymore. You’ve set a rule. I have this thing called gatekeepers and one of the gatekeepers of the rules that we set. That’s a rule that you set and then you don’t have to come back to it. You can let it do its thing. You can do and focus your time and attention everywhere else. I like that.
The beauty of it is I end up with less than four hours of meetings. If I propose a meeting to someone and we ended up taking on another day, so if I propose meetings across three days, it’s not going to tell me to propose that same time again. That meeting slot was reserved for someone else. They chose another day. That’s fine. I’m having less than four hours every single day without thinking about it. I know a CEOs job. They take meetings. It’s also forced me functionally running the business to choose and decide. I’ve taken no meetings from an outside party, even from investors. Few and far between, I step out of my zone to have a meeting even with an investor, because it’s not my focus for this quarter. It’s been helpful to have that. I don’t even think about it. I just know that on the first week of September 2020, fundraising done, turned the dial down, and since then I look at my calendar. I’m like, “This is light. I love it.” I wake up every morning like, “I’ve got six meetings today. It’s cool. Let’s go.”
Undock solves the last mile issue of scheduling and availability. Get Undock for free https://bit.ly/pzundock Share on X How do you deal with the people who can’t get on your calendar?
That’s tough.
These could be your employees that are like, “You’re never available. I can’t get on your calendar.”
Most of my meetings are now internal. They can all get on there. Occasionally, they’ll say, “I couldn’t get in for now. I’m not sure if you’re free or not.” For the most part, I’m like, “The calendar is the Bible here. Book it tomorrow. Is it urgent?” No? Book it tomorrow.”
What if they can’t move forward? It sounds like you were saying you were the bottleneck. The reason I’m asking you this is because this happens for a lot of entrepreneurs. Their team feels like they can’t continue working until they get that answer. They’re there. They were standing outside your door. Now, they’re sitting at their desk and they’re twiddling their thumbs. They’re like, “I can’t meet with him tomorrow. I’ll play some more whatever we can play today.”
It’s Minecraft or something. That’s not the game they’re playing. They’re playing Among Us.
Whatever the game is. I’m not a gamer. That could happen. How do you deal with that outside of the tool? The tool has protected your time. The question is, how do you deal and what do you put in place to make sure that you’re still keeping people happy and getting work done?
It’s important you say that because a lot of things happen. Number one, they become accustomed to not being able to get time, which is a bad thing. They’re like, “I’m back.” At this company, we do not have that problem. I can pull my employees and I’m available enough for them, but they can get used to that.
It happened at one point and it happens to other people.
For me, the hardest part of that was I know that it’s not inefficiency for the time like the business is going to struggle. If everybody is waiting for me to do something or answer something, then there’s so much momentum that’s being lost in that time that it’s not happening.
Culturally, they might feel unimportant. It’s important that we realize as leaders how could that be impacting our culture, and how do you deal with that? How did you deal with it at the time that it was a challenge until you got Undock working?

TBT 140 | Undock

Undock: If everybody’s waiting for you to do or answer something, then there’s so much momentum that’s being lost in that time that it’s not happening.

I did not do it very well. Some employees would come to you and say like, “I feel like I can’t get twenty minutes of your time today.” I was like, “No, I was free from 1:10 to 1:30. How come you didn’t reach out to me?” I never solved it at the company mainly because I didn’t think the velocity of my day was insane. I looked at other software and applications like, “This isn’t going to fix it.” If there was any solution that I could think of either procedurally or through software, then I would have done that. I’ve used every software app before I ever built something like Undock. If there was an extreme case like three different companies, three different conversations, all small companies, no hierarchy, everything is up to you, I don’t know how you do that.
I’m going to throw my coaching hat in the rain here for the readers, and maybe you’ll say, “Yes, that’s what I did.” Sometimes we do things and we don’t know what we did. The first thing you did is you stepped back and you recognized that you had a problem. For the readers, you have to recognize first that you have a problem. You have to understand what are the costs and impact of the problem. It’s not just recognizing it, and then allowing it to continue to happen, but we identify what the cause were. You saw that this was wasting a lot of time and so forth.
One of the things is you looked for a solution. It’s to problem solve what are different areas. You saw, “I was available. Why didn’t you come at that time?” That matching was super important because then you could at least cover that piece of it to get the matching of time. That was one way to solve it. The other thing that a lot of people forget about as leaders and don’t realize how important it is, and you did this, is to have an open discussion with your team. You let your team know altogether that you know this is a problem, even if you don’t have an answer. A lot of people feel like, “I can’t go and talk about it unless I have an answer,” but it’s perfectly okay. You can tell me whether you did this or not. You go to the team and say, “I’m sorry. I see that this is a challenge. I’m working on a solution.”
That lets them know that you recognize it and you’re owning it. You want them to own their stuff. We got to own our stuff. It helps them to also feel like they matter, instead of pushing it under the carpet and being like, “You’ll have to meet me next week or find a time anywhere.” If we can have these open discussions and say, “I know things are insane and I’m trying to work this out, bear with me.” I found that that authenticity and openness goes a long way with people. Did you do that?
I did do that and I took it a step further. I say, “I was trying to have more structured meeting times to answer some questions there. That way you don’t have to individually all chase me.” I took it one step further and I opened the floor. I said, “Can you also tell me what else am I doing wrong? How can I empower you? Where could your skillset be better?” This is a few years back. I can’t remember the exact things that I put to the table for me, but that was the first time I had done that. I don’t know how effective it was the first time, but I’m extremely open to feedback and criticism directly from the team. It’s tough to engender that environment where they feel safe to do that. They’re like, “If I tell you, you suck at this, then you are going to fire me.” I don’t think they ever felt that way. I even pointed out like, “I don’t do that. You know I don’t do that. I know you need to do it.”
That’s how you do it. You didn’t realize it, but that’s how you build that trust. You know, “This isn’t my forte.” They then feel comfortable when you invite them to share some constructive feedback if you’re comfortable to do that.
I still struggled with it throughout until 2019 when I was able to start using Undocks. This is not a product plug, it’s just that I’m not the most efficient manager of people’s time. I’m a great manager of my own time, but other people, I’ve got a lot of work to do.
It’s a challenge to add everyone else’s time on top of your time. It’s hard enough to manage ourselves. I have not yet used the tool, but I’m super excited to get it installed and get it working for me because I think that’s a cool option. With all the entrepreneurs and CEOs that I work with, I’m going to put it to the test.
It even has the thing you were talking about for doing your updates or recording little videos instead of having the meetings. You can do all of that right inside of your calendar.
Is there anything else you wanted to share about any additional things that are up and coming? Something that the AI does that we didn’t talk about or anything else before we sign off?
There’s a lot that we didn’t talk about.
What’s your favorite feature?
With Undock, no one ever has to worry about scheduling ever again. Share on X The favorite feature is that you can be scheduling it. Working with autocomplete is fantastic. You don’t have to do anything. You don’t have to go to another app. You don’t have to go copy and paste anything. You keep typing on Undock and you’ll see your suggestions. You hit the tab like autocomplete. That’s great. My favorite new thing, we built it in April 2020 and then prototyping a stronger and more powerful version. Let’s say somebody were to say, “I’m flexible. You pick a time. Here’s my Undock calendar link or my booking link.” You can hover over that. Without leaving your email, you can click a time that works for both of you.
What if that person doesn’t have Undock and that person has Calendly or x.ai or HubSpot or Outreach, and they’re using all these tools that are tightly built into their workflows or whatever it may be? They’re like, “I’m not going to sit back and forth with you. Here’s a link. You can do the same thing with our tools.” Our AI is able to understand those calendar links, extract that person’s availability, compare it with your availability preferences and schedule behavior, and make a suggestion in one click.
What that does is it’s helping the entire ecosystem. It’s making it so your calendar can talk to my calendar like that. There’s no debate about, “You go do the work. No, I go do the work. It trades times back and forth. No, let’s use a bot.” There’s none of that. It’s like, “Here’s my calendar automation tool. Here are the three times that work for all of you.” We’re excited about that. It blowing some minds and it’s about to get powerful in January 2021 when we launch version two of the product.
Nash, thank you for being here and sharing your tools and some of your challenges. I’m excited for the readers to get that work in and provide some feedback to us.
Go to Undock.com. Sign up, it’s free.
Is the tool planning to stay free or is that going to change?
Everything that I’ve discussed is free. The way the scheduling works is free. We’re trying to get a billion users on the platform. No one ever has to worry about scheduling ever again, but we are releasing a full calendar, which will have some paid features, premium features on that. The scheduling portion of this wildly omnipresent and proliferating scheduling experience will be everywhere and will be free.
What are you doing? You better already be on that site. It’s free. You’ve got no reasons, no excuses why you can’t be using this tool.
There’s so much more coming.
I love how excited you are about it. You’re beaming smile shows that you’re passionate about this and excited to get it out to everybody.
Thank you for the time, Penny.
Thank you all for being here. We’ll see you in the next episode.

Important Links:

About Nash Ahmed

TBT 140 | UndockNash Ahmed, Founder and CEO of Undock Nash Ahmed is a serial telecom executive and the Founder and CEO of Undock, an artificial intelligence-enabled meeting platform built for the future of work. Nash and his team graduated from Entrepreneurs Roundtable Accelerator (ERA) in May 2020 and raised a $1.6M seed from Lightship Capital, Bessemer Venture Partners, Lerer Hippeau, and other notable investors. Prior to Undock, Nash ran a company that started providing telephony solutions to enterprise clients and evolved into a full suite of technology services. That path led to his interest in communication tools and particularly video. Nash’s unique expertise includes product building from a design and engineering perspective. He holds a bachelor’s degree in computer science and business management from Drew University, but the design has always been a personal passion that manifested itself in projects ranging from graphics and photography to interiors and audio production.
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