Delegation Challenge – Days 12-13

The 30-day delegation challenge continues. Here’s another update.

Day 12 – Booking Accommodations

On the first day of our trip, Rachelle and I booked a night in an AirBnb ourselves. But we were heading to a different city on the second day, and I thought it would be interesting to see if Magic could help us find a place to stay for a couple of nights before we returned to Vegas.

I’d never delegated the task of finding a place to stay, so I figured it might take some back and forth. Magic wouldn’t know our likes and dislikes, so I wasn’t sure how this process would unfold. But I figured that this was as good a time as any to get started, and I figured that Magic probably has a lot of experience with travel-related bookings. I assumed this would likely be a strength of theirs.

Rachelle and I often travel spontaneously, knowing that we can always find a place to stay via AirBnb or Expedia, even after we arrive in another city. Our accommodation preferences tend to depend on the situation though. If we just need a place to sleep because we’ll be spending our days out doing various activities, a spare bedroom in an AirBnB works great. If we’ll be spending more time in a place and especially if we’d like to do some work, we may rent a whole apartment or even a small house. We like having a kitchen for longer trips too. When attending conferences or business-related events, I usually prefer hotels (ideally the venue hotel), so we can be close to the action.

Our price range can fluctuate too. Sometimes we’ll stay in an AirBnB for around $50 a night. Sometimes we’ll stay in a 5-star hotel for $300+ per night. It really depends on the situation and what kind of mood we’re in.

As I was leaning into this, I was wondering in the back of my mind how this is going to play out over the long run. How do I get started with delegating travel bookings such that a VA can learn to match our preferences efficiently as they gain experience with us? Will we have to explicitly spell out what we want each time? Or will they get good at predicting our preferences based on the situation?

I figured that the best way to get started was just to start, knowing that there’s going to be a calibration process to go through and that my first experience could be inefficient due to all the back and forth that could be needed. But I was also open to the possibility that maybe it would be faster than I expected. I figured Magic must have a lot of experience making travel arrangements for people. I thought they might even have a well-optimized process or script to follow for the first time someone enlists their help in this area. As it turned out though, I didn’t see much evidence that they had a very refined process for this. It actually felt more random than I expected.

I felt this short trip would be a good time to attempt some travel-related delegation. I knew that if it didn’t work out with Magic, Rachelle and I would still have time to find a place on our own via AirBnb or Expedia. Even though this was a holiday weekend, L.A. is a big city. We’d definitely find a place to stay.

Just before 9am on Friday, I sent Magic this request:

My wife and I are on a road trip in Southern California, and we need a place to stay tonight and tomorrow night in the west side of L.A. Just the two of us.

I used a pretty relaxed opener to get the ball rolling, knowing that Magic would surely have to ask us some follow-up questions regarding our preferences. I could have shared more details about what kinds of accommodations we wanted and more specificity about our location preferences, price range, and so on, but I figured they’d know what to ask for.

They acknowledged my request in less than two minutes, confirming that they’d look for options for two nights on the west side of L.A. They said they’d update me again in 60 minutes.

I found that initial response a little puzzling. Didn’t they need more info to get started? But it was only around 9am, so even if they took several hours to eventually figure out our preferences, we should still have plenty of time. I thought to myself: Okay, let’s see where they take this.

They got back to me 57 minutes later with a single recommendation: The Hampton Inn & Suites in Barstow, California for $122.84.

I wasn’t sure if that was the total price or per night, but the location was nonsensical relative to my request. Barstow is indeed in Southern California, but it’s about halfway between Las Vegas and Los Angeles, about 130 miles driving distance from the location we asked for (i.e. west side of L.A). This is roughly equivalent to asking for a place to stay in Washington DC and being offered a hotel in Philadelphia.

On a galactic scale, we could say they nailed it, but on a human scale, this is a pretty big miss.

This was confusing to say the least. But I also thought that we can only get better from here, so let’s keep trying.

Barstow isn’t the right city. That’s 100+ miles from L.A. We need something in or near Santa Monica.

They apologized for the mistake and later got back to us with three hotel options: a standard room at the Beverly Hills Marriott for $229/night, a 1-bedroom suite at the DoubleTree Suites by Hilton Hotel Santa Monica for $253/night, and a premiere room with a balcony/terrace at the Ambrose Hotel for $279/night. They shared these options in a PowerPoint style document that included 4 photos of each place.

These places looked very nice but seemed more appropriate if we were seeking a resort-like vacation. For our road trip through familiar territory, we really just needed a place to sleep since we’d be out and about during the day. So I thought I’d steer things a bit, but I also thought it would be nice to have Rachelle take over interfacing with Magic from this point, so she could gain some practice too. She texted back:

Thanks. Can you also look into options for AirBnb, within 2 miles of the beach? Between Santa Monica and Manhattan Beach. Entire apartment or Private room, as long as there’s a private bathroom. Thanks!

By this point it’s 11:44am, so we still feel like there’s plenty of time to calibrate and secure a place with Magic’s help.

They followed up at 1:17pm with some AirBnB options: a 2-bedroom apartment in Santa Monica for $315, a 1-bedroom apartment in Venice for $357, a Venice beach house with a private garden/patio for $449, and a family house in Culver City for $305. They included 3-4 photos of each option as well as a pic of the AirBnB map showing the general location of each one. It was nicely presented.

These were all pretty good locations. I’m super familiar with the area since I grew up on the west side of L.A. This was the area where I did a lot of distance running too, especially along the beach through Marina del Rey, Venice, and Santa Monica. So I felt this was a nice way to test Magic because it would be easy to validate what they were coming up with, at least with respect to my knowledge of the general area.

I thought that $300-$350 would be fine for a 2-night stay in the vicinity. Renting a whole apartment was more than we needed for this trip, especially the 2-bedroom option, but I was amenable to the idea, and it looked like they’d found some decent options.

Rachelle and I felt the first or second AirBnB options could work (both within easy walking distance of the beach), so we asked Magic for links to those listings, so we could check them out in more detail. Magic obliged, actually by sending links to all four options. Rachelle checked them out and immediately noticed another problem – we had asked for two nights in our original request, and these listings (and prices) were all for one night. The places that interested us weren’t even available for a second night, so these listings didn’t match what we’d asked for.

While having a whole apartment would be nice, we felt that if the prices were going to be $500+ for two nights, that was overkill for this trip since we just needed a place to sleep and expected to be out all day. Rachelle text again to further calibrate the request:

I checked into these. They’re all actually for 1 night only. Can you please try again? This time see if you can find a place for about $300 (or less) total for the two nights. Remember a private room is okay too, but if we go that route we’d like it to have a private bathroom (not a shared bathroom).

Magic acknowledged this within 4 minutes, and it took them another 90 minutes to get back with some updated listings, now at 3:47pm. At this point we were feeling that the mistakes had slowed the process down too much and that we’re going to need this to converge faster, or we’ll have to abandon the request and research and book something on our own. But we still had enough time to try for one more round.

This time Magic got back with five options: a private room in West L.A. for $284, a private room in a beach house in Pacific Palisades for $305, another private bedroom in West L.A. for $364, a private master bedroom in Marina del Rey for $303, and a private bedroom in Venice for $305. All of these listings had private bathrooms, and the prices were for 2-night stays. This time Magic included direct links to the AirBnB listings as well, so we didn’t have to ask for them.

Initially this looked good… until we checked the actual listings.

Rachelle and I use AirBnB a lot, so we know to look for hosts with solid reviews, preferably 4.5 stars and up. Staying in a newly listed place is okay as long as it’s with a reputable host with a history of strong reviews for their other properties. We especially love booking with “super hosts” since they’re rock solid reliable.

The first listing had a solid 5 stars with 85 reviews, but it wasn’t our preferred location since it was farther inland from the beach. It might have worked, but we ruled it out due to the location.

Another listing had no reviews. The host had reviews for other properties, but some reviews were bad, like this one:

This place is not what is pictured. It’s a dirty cluttered two bedroom apartment with a partition that tries and fails to hide massive amounts of junk. I am sure there has been a cat in the apartment at some point because the smell is obvious.

Or this:

Pictures on site do not match the place. Host specified “utilities extra” in listing but that term is vague. The place did not appear to have been cleaned since last visit and there was no toilet paper or towels. It was not a good experience and I did not stay there much, although I paid for a week.

I’m allergic to cats, and I value cleanliness. So we felt it best to pass on this host. It felt riskier than our normal standards.

Another place was a new listing with no reviews. The host was listed with a 0% response rate and a response time of “a few days or more” – both bad signs if you want to secure a place for the same day. Strong hosts have a 100% response rate and a response time of less than an hour, and these are key factors to look for if you want a same-day booking. This particular host had only four reviews, and two were about canceling reservations that had already been made. So this was an easy no.

Another option Magic listed had only one review – a pretty bad one:

Showed up to the booking and it was apparently occupied. I spent 2 hours outside of the apartment trying to figure out how to get in because the host would not answer messages and calls. Finally after 2 hours he calls back and tells me its occupied and just hung up. I was in standing in the middle of Venice late night with all luggage trying to figure out where to stay. This was absolutely ridiculous. The host did not apologize or seem to care at all. I gave him the benefit of the doubt. The host did not even cancel the reservation. My next Airbnb host was kind enough to contact customer service for me and report the issue.

So that was another easy no. No one wants to deal with a flakey host.

Fortunately the listing in Pacific Palisades looked really nice – 4.5 stars with 23 reviews. It was farther north up the coast from Santa Monica but a very nice area, so we’d have been happy there. In fact, we actually tried to book that one after rejecting the other four options. But as soon as I tried to book it, the host immediately responded that it wasn’t available:

Someone already booked these dates on a different platform I apologize. Have a good weekend

It’s rare when this happens, but we’ve had this happen on a few occasions when hosts use multiple listing sites for their properties and don’t update their AirBnB availability dates. I wouldn’t count this one against Magic since they couldn’t have known this from the listing.

By this point we had already arrived in the area where we now needed a place to stay for the night. We felt this process was taking too long to converge, and at the current rate of progress, we couldn’t expect Magic to bring this across the finish line for us quickly enough. So we went to a Starbucks, looked into AirBnB and Expedia options, and ended up booking a nearby DoubleTree Hilton hotel via Expedia, an option we found independently. We actually ended up going with Expedia’s #1 recommended option for us. I’ve been using Expedia for many years, so perhaps they know my preferences pretty well by now.

As soon as we booked the hotel, I texted Magic to close the request at 5:26pm, almost 8.5 hours after we opened the initial request.

We tried to book the second one but unfortunately someone else had booked it via a different service, so it wasn’t available. A couple others on the list had no reviews or a really bad review for the host. We’re out of time unfortunately, so we just booked a hotel nearby.

The hotel worked out fine. I’m a Hilton Honors member, so they gave us free waters when we got there as well as half-price parking. I was feeling a little frustrated when I arrived, but their friendly clerk put me at ease and helped me feel good about the choice.

So this was a disappointing experience working with Magic. Enlisting their help this time unfortunately didn’t save us any time or trouble – quite the opposite. We spent more time going back and forth with them, including correcting their mistakes and looking at inappropriate or unavailable options, than we would have if we’d just did our own research.

This was my first time doing this particular type of outsourcing, so maybe I could have done things differently, such as by starting with a more focused request. And perhaps it would have been better if we’d been able to give them more lead time. But I felt that starting around 9am should have been okay to get this done without too much time pressure. I also felt this type of request should have played to Magic’s strengths.

So I’m not sure what to make of this one, but I’d have to call it a miss. The way this request was handled felt pretty amateurish to me. In another sense though, I still regard this delegation attempt as a success. I’d never tried delegating finding a place to stay while traveling, and now I’ve at least made the attempt. I still see some good potential here, but I think it will require much better calibration than what I experienced this first time. This experience also helps me better understand what I value, especially when using AirBnB: reliable hosts with solid reviews (4.5 stars or higher), cleanliness, and responsiveness. Rachelle and I have had great all-around experiences with AirBnB, including staying in one AirBnB for 30 days straight, partly because we know how to avoid the bad hosts. Social proof goes a long way.

At this point I’m also wondering how much this process could have been improved if I had pre-shared some of my preferences with Magic in advance. I know they maintain an internal wiki for each client, so perhaps if I helped them fill in more details, it would make them more efficient with certain requests. But then I’m also wondering if this is pulling me back towards algorithmic thinking too much.

This is an odd situation because with a service like Magic, I could be working with different people across a single request, and I never really know when a request changes hands due to a shift change or for some other reason. If I’d made this request on a different day, or if it had been assigned to someone else, this could have gone completely differently. I imagine that the consistency of service is probably a considerable challenge for Magic. I’m just not exactly sure how to best approach helping them calibrate for new types of requests. I am, however, hopeful that such a service could learn and adapt as we continue working together.

I like that I can get a request going with a simple text message, and the details can be worked out as we go. Sometimes I feel like I can trust Magic to do a good job of steering on their own, such as they did with finding someone to pick up my old weight training set. But other times I still feel responsible for steering the request to make sure we converge on a decent solution.

This unusual day eventually transitioned into a dinner with my friend Rich Litvin, whose articles I shared in the previous post. Rich, Rachelle, and I met up at a nice vegan restaurant near Venice Beach. We talked about many topics, including delegation and team building. I hadn’t seen Rich in person since 2013, so it was nice to catch up.

After dinner Rachelle and I went for a walk along Venice beach. Then on an intuitive feeling, I decided to stop by my old Tae Kwon Do studio just to see it again. I knew that no one would be there since this was around 11pm. But as it turned out, while I peered into the window and recalled some fond memories of the place, Rachelle noted that there was someone still inside – the instructor/owner. I knocked on the glass and greeted him when he came to the door. He invited us in, and we had a nice catch-up chat. I hadn’t trained at that studio in about 19 years. But he remembered me, my brother, and my sister since we all used to train there. I recalled so many memories when I stood at the edge of the mat. We even talked a bit about delegation. Almost every conversation I have now can include some talk about delegation and teamwork; everyone seems to have a unique take on it.

This was a fairly short trip, but it was a good learning experience trying to delegate and manage some things from the road.

Day 13 – More Reading

All I did delegation-wise this day was read through some additional PDFs on team building that Rich had sent me. I took some notes on how I might apply the ideas he shared, especially with respect to the types of people I’ll need to have on my team.

I seem to be experiencing cycles of ebb and flow with respect to this experiment. When I do a lot of delegation, I sometimes feel a need to back off and have a more introspective day. And then after a day or two of that, I feel ready to push myself again, get more energy flowing, and start assigning more tasks. I feel this is a good way to ease into delegation with action and not feel overwhelmed. With each new round of action, I try to push the edge of my comfort zone in a different way. Presently that’s pretty easy since there are lots of things I still haven’t tried yet.

I realize that in the 30-day span of this experiment, which is nearly half over now, I’m only going to make a modest dent in the vastness of delegation-related skill-building. But I think it’s a pretty meaningful dent. I’ve learned a lot already, my mindset has shifted a good bit, and I’m making mistakes shamelessly and recovering from them. I’m very pleased with the progress I’ve made on this path in the past two weeks.


The contrast between a delegation request that goes really well and one that doesn’t is also helping me calibrate in a different way. I’m learning more about how to leverage delegation effectively.

I enjoy delegating when I feel like I’m working with someone who has my back, and I can trust them to make reasonably good decisions along the way.

As I gain more practice working with Magic, I think that my success in leveraging their service will largely depend on the experience and skill of the person handling my request at any given time – and also their skill in assigning my request to a qualified team member. As I worked with them on the WiFi request, I got the distinct impression that at some point my request may have changed hands, shifting from someone who wasn’t qualified to handle it to someone who clearly was. I’m left wondering if there’s anything I can do to increase the likelihood that my requests are assigned to someone who’s a good match for handling them. So far it feels like a bit of a coin toss as to whether my request is being handled by Hermione Granger or Ronald Weasley, and I’m wondering if there’s anything I can do to increase the chances that my requests get assigned to Hermione each time.

I really like Magic’s flexibility. It’s great that I can assign them a wide variety of tasks and see how they do. I think it’s best if I’m willing to take a chance and see if they’re able to come up with a good solution. I can accept that I may sometimes have to steer the request to get what I need, and on some occasions I might have to abandon a request if I conclude it would require an excessive effort to achieve convergence in a reasonable period of time. I actually find this less-than-perfect experience empowering because it helps me get past potential worries about perfectionism when delegating. I can throw lots of darts at the dartboard, knowing that sometimes I’ll hit a bullseye, and sometimes I’ll hit a window, but on balance I can still come out ahead just for making the effort enough times. I actually find this comforting in a Forest Gumpian “life is like a box of chocolates” sort of way.

Maybe for some people, this realization doesn’t seem particularly profound. But coming from a programming background where a single error can prevent a program from even compiling, it’s a pretty big deal to approach delegation in such a forgiving, fault-tolerant manner.

I suppose another aspect of calibration that I still need to figure out is how to balance maintaining high standards with flexibility and forgiveness.

Proactive vs. Reactive

One thing Rich helped me clarify is that I could use an implementor on my team, i.e. someone proactive who gets things done without having to be told what to do. This idea strongly resonates with me.

Having a team of VAs helping me is a nice step, but I still have to figure out which tasks to assign them and then handle the back-and-forth as they work through each item. I’d be more productive if someone else handled all the VA delegation by chunking down bigger projects. I’d rather work at a higher level of abstraction by helping to identify which projects need doing and defining the desired outcomes. I’d rather not delve into so many implementation details like I’m doing now.

What I really need is my own version of Commander Riker from Star Trek: The Next Generation. I need a First Officer. I need someone who understands the ship’s overall mission, who feels personally aligned with that mission, and who can keep the ship running smoothly, so we can do a better job of exploring the galaxy (of personal growth) together.

I want to be able to say to someone, “Let’s do a 5-day live event in Vegas in the Fall of 2019, the first 2 days exclusively for CGC members, and the other 3 days as a public workshop.” And this person will figure out what needs to be done, including delegating work to VAs if necessary. Then after the event, we’d sit down and go over the details of what worked and what can be improved for next time.

Even better would be to have someone who will say to me, “It’s been a while since we’ve done a live event. I think we should do one in 2019, and I’d like to get the process started. Let’s pick some dates.”

This would be good too: “CGC members are clamoring to meet in person. I suggest we begin hosting two live events per year on a regular schedule, like one in the Spring and one in the Fall. I can get the ball rolling on that if you’d like.”

I could probably even go for this: “Steve, we’re doing another workshop in the Savoy room at the Flamingo Hotel in October. You’ll be doing half of the content, and we’ve invited several CGC members to contribute other segments, so they can get some stage time too.” I rather like the notion of having someone who could steer the ship independently of what I’m doing, and then plug me into the system as a resource.

This kind of delegation sounds almost too good to be true, but I have to believe it’s possible because I have friends who already have team members like this. I think this would be a powerful direction to go, certainly more powerful than working with VAs directly for every little thing. I’m not sure how to go about finding someone for such a role yet, but I have some ideas to get started, and I have many friends that I can ask about this as well.

That said, I feel like my current virtual assistant phase of delegation is a good one to go through. I’m still learning a lot from it. Even if I had a great First Officer, I think there would still be situations where I may want to delegate directly to a VA or team of VAs, especially for personal tasks. But I do feel that finding a really strong First Officer would be a huge step forward. If I could name the one thing that would make the biggest difference here, that would probably be it.