Album Review: The Past is Still Alive (Hurray for the Riff Raff)

One of my favorite R.E.M. anecdotes passed on through the years is how Michael Stipe reacted to hearing Patti Smith’s Horses in his formative years. The story goes that he bought a few albums, took them home, had a whole bowl of cherries while listening to them and was so moved by the music that he threw up afterwards – and decided then and there to be a musician. A bowl of cherries will do that.

For me, Hurray for the Riff Raff’s The Past is Still Alive is one of the finest albums I’ve heard in quite some time. No cherries nor vomit, but this is a damn good album.

I’m not new to Alynda Segarra’s music, really. The first song of theirs that hit me was “Living in the City” from 2017’s The Navigator.

The album at large didn’t quite land with me, but there was something very special – if slightly underbaked – about “Living in the City.” Segarra’s writing is so evocative of a place in this song that before I really cared about the video I had gone with them on a voyage. There were a few lovely layers and textures (the backing vocals!) and amazing deliveries on lines like, “I watched the city quiver.”

I’d followed their music off and on since then and dug a few tracks off 2022’s LIFE ON EARTH – “PIERCED ARROWS” is a great power pop song with a soaring chorus; “RHODODENDRON” is a grower that inserts itself into your noggin and lives there, unveiling more and more on each listen. The lushness of LIFE ON EARTH was notable and the whole piece just felt more organic versus the balance of something like The Navigator. Through it all, though, Segarra’s songwriting hit a really nice target. Their lyrics blended the literal and the figurative, stories and fables and the reality of life, with an admirable level of economy – they’re an amazing editor. Their music got more ornate and denser, but not to a fault.

That brings us to 2024’s The Past is Still Alive. The album cover sets the tone and the mood. This is not an album of a trivial nature; this is serious shit, this person has seen some shit, and they’re very present with us here… and yet, it’s a bathtub against the barren landscape.

But barrenness isn’t permanent, and it isn’t how things have always been nor how they will be. In this piece, Segarra turns over the ideas of memory and time and history so like a pebble in their hand as we see their life flash before our eyes in song. “You don’t have to die if you don't wanna die.” “I’m in the back of the pickup most of the time. It’s all in the past, but the past is still alive.” “Return to the rocks and stones.” “These things take time; I know they do.” “Most of our old friends are dead.” “You told me your big secret on the F.D.R.” “Now what do you turn to when all reality’s bending?”

The feel and fabric of the album is just as organic as LIFE ON EARTH, but the spirit of it leans more introspective. This album is, to me, more accessible. Songs are tight – the soaring “Ogallala” earns every one of its five minutes but it’s the longest track here – and we’re in most scenes for just a few minutes. On the road in “Hawkmoon”, meeting Miss Jonathan (“I could have ridden shotgun forever”), being exposed to the bigness and queerness of a person and a city. A poignancy and moment of nostalgia… then it’s gone. Time collapses in on itself in “Vetiver”, the natural world contrasting with a hook up at Stonewall (a rare moment of wit shows up: “She broke my heart, but at least I got a shower in”) and the feeling of missing someone or something and going back to one’s roots. “Buffalo” reaches out after leadoff track “Alibi”, masquerading as a straightforward guitar & vocal track before it deepens to a meditation on extinction and loss. Easy stuff. Through it all The Past is Still Alive builds into a retrospective of one’s life told in vignettes, contrasted against a real struggle with time. This shows up in the functional closer “Ogallala”: “I used to think I was born into the wrong generation, but now I know I made it right on time.” Segarra’s voice is triumphant but not victorious; they belt this line with the emotion of someone who won it all but also lost it all. Just a stunner.

The album ends with “Kiko Forever”. The club is closed, the story told, and we’re left with a jazz ditty haunting the room after hours as voicemails from Segarra’s late father play front and center. The voicemails are what you’d expect from a parent to a child. How the day is going. Making chicken wings. Saying they’re proud of you. Even here, we have those little glimpses into the daily life of someone. And then the track ends abruptly. So does life.

I definitely saw a thread to my favorite R.E.M. album, 1992’s Automatic for the People. That piece is more straight on about death and mourning and loss. But I loved putting a track like “Find the River” (“None of this is going my way”, and the shout-out to vetiver and the natural world) in the same sphere as this album; R.E.M. goes for the oblique, as is typical, while Hurray for the Riff Raff goes for the literal. But while The Past is Still Alive isn’t “about” death and the passing of Segarra’s father it opens more doors than R.E.M.’s album via the stories and the vignettes. Stipe and crew are there to emote with us and commiserate, while Segarra is here to honor and tell the stories of those who are with us and those who are not. Automatic is the immediate balm for massive loss and The Past is Still Alive is a reflection and renewal of what life was in the first place. It’s how we celebrate and remember people when they’re gone, and should be what we do when they’re here, too.

The Past is Still Alive is one of the best things I’ve ever heard. I’m eager to see what Segarra does next of course, but in the meantime they’ve given us something very special and very real.

Further reading: Matt Mitchell's great piece on this album at Paste.

It’s in the Bag: The 2024 Mostly Everyday Carry Update

When we last spoke I was searching for a new bag (or everyday carry or EDC) to handle my commute to work. While I primarily drove to work back then I also needed a bag that would handle client trips. The bag that won was the Topo Designs Y-Pack – a very simple, not-too-large bag. The Y-Pack, at that time, cost me a whopping $57.00.

Coming up on eight years later – eight years! – things are a bit different. I never commute to an office; my home office is my office. And while as of the writing of the start of this post I still owned and used the Y-Pack, after this long a time its mild negative qualities have worn on me. Truth be told, eight years is a great run for anything of this nature – it was used full-time daily for four of those eight years – but my needs have now changed.

Let’s talk about the Y-Pack for a moment in this context. This is an OG Topo Y-Pack, with no external water bottle pockets. It’s a big flap pocket on top, and outside of a laptop area inside, just a big space in the main compartment. No comfy straps, no suspended laptop space, no organization, no frame, no frills. That’s it! Early on while using it I kept with the “bags in bags” model that works for so many people only to find that I really got tired of it.

The size of the bag is still pretty great. It’s not a monster and fits very easily under an airplane seat. (Getting it out from the seat is a little hard – the top handle often gets smooshed underneath, so it’s a tough stretch for me to access the bag during a flight without using my foot to slide the bag out first.)

One thing that is critical about this bag, and one major reason I’m looking for a replacement: the straps. They are very cool, in the style of old-fashioned seatbelt straps, but they offer no support at all. (The current Y-Pack does have padded straps.) I had moved to a backpack to help out my shoulders in the first place and while the form of a backpack is totally what I need to stick with, I need something that has a little more give and softness. The handle atop it is also pretty uncomfortable as it, too, is just a simple strap with no padding; when I have even a light load in this, that strap hurts my hand.

In my last update post, I had noted the professionalism factor. The Y-Pack is absolutely not a professional bag in the bright turquoise color I have; it is a casual one. I strutted in that post a bit with a “I can rock it” attitude and, listen, I certainly can – but I am wanting something that can go both ways. A solid color, but a unique one, that is a bit more muted is in my current style wheelhouse.

The overall state of the bag is good. It is showing wear in a few places, and a stitch in the bottom of the laptop compartment is coming undone. There are a few small stains on the outer fabric that haven’t come off with (basic) cleaning, and the fabric around the main cinch cord is looking a bit ratty. Still the value of this bag, especially at its purchase price, is ridiculous. It’s well-made and gives me confidence in Topo's stuff.

A couple of my prior bags – the Timbuk2 Eula and Blogger 2.0 – are still completely usable, but don’t align with what I need these days. The Eula is a purse, good for when I don’t need a computer and just want to have a notebook and a lunch, or random things. The Blogger is on reserve as a standby backpack but I haven’t used it in a decade now; it’s partially the form factor and partially the color/aesthetic. Kudos to Timbuk2 from the 2000s for making good stuff.

Fine Tuning the Needs

Nowadays I need a laptop bag primarily for airport and similar travel. I’m traveling more than I did in the past, so a bag needs to be comfortable and manageable for walking around the concourse and hopping through TSA & customs. When I am local and head out to work at a coffee shop or coworking space, the bag still needs to do its job – but utility will be more important there. And of course it needs a presence at client meetings and workshops as well.

My loadout is much smaller than it was back in 2016, accordingly. My typical carry includes my 14” MBP, headphones, notebook, a book or two, pens, sundries, power bricks & cables, and a slim Kleen Kanteen water bottle. I may toss in a knit cap or a scarf and some snacks but nothing physically large. I am not a terribly tall person so having a backpack that is large (either tall or deep or both) is not great for a lot of reasons. And, well, weight is important too. My shoulders should only get cooked when I’m lifting weights. A bag needs to go easy on me, and not be heavy or overwrought on its own.

I do want some structure and not a floppy thing. Organization is now important to me; I like a bag that has some spots for things. I definitely need exterior water bottle access or something similarly fast. I also want a minimum of fuss to get into the main area (especially the laptop area) of the bag. The cinch drawstring of the Y-Pack is certainly not bad, and it is fast, but it is not terribly elegant.

Lastly it’d be nice if a bag could go on top of a carry-on’s handles but I’m largely on Team Always Check a Bag these days so this is less of a concern.

As far as budget goes, I’m planning to stay well south of $300, but $200 is far more comfortable and anything less is a bonus. Price is a factor, obviously, but I will admit I mostly want to be *done* buying bags. If this thing lasts 20 years I’ll be thrilled.

Contenders: The Brands

First, yes, I looked at a mix of brands without trying to get too wild. Mystery Ranch was probably the name I saw the most whose bags just didn’t hit with me. Timbuk2’s quality, as I understand it, did not stay the same in the past decade or so. Peak Design has lovely stuff but universally people said their bags were heavy. There are others but, again, I wanted to dig into this but not spend months in analysis.

I had originally gravitated towards Tom Bihn due to their reputation for quality, thoughtful goods that last forever. Tom Bihn recently got an investment round (Tom retired) so I had a small concern that the quality and the like could take a hit; based on reviews it’s unclear if that’s the case. The aesthetic of Bihn is a little busy and doesn’t play to fashion at all, but they offer some great colorways and I’m certainly not mad about that. However, the Synik and Synapse models I looked at ranged from $250 to $350, and the requirement to buy a laptop holster for several models ($50, and out of stock lately) just wasn’t great to think about. I set aside Bihn for the time being.

Evergoods is a little shop out of Bozeman that I caught wind of on a Tom Bihn forum. They have a limited line of products but are well known in the nerdier portions of the EDC and bag communities. I like a lot of their things and like that they’re a small company, designing and making things very carefully. Their product line for backpacks is very limited so it’s a “love it or leave it” type of offering. Everything comes in black, with an occasional second color. Some of their collabs have beautiful waxed canvas fabrics and colorways but aren’t returnable, and run way more expensive than the standard options.

Aer is another brand clearly going for the post-hipster tech aesthetic – simple, clean, understated looks. They have a nice variety of bags that look very high-quality and completely professional. The company itself is small, so you can sense a theme here, but there are zero names on their About page (with only four peeps on LinkedIn) and that makes it feel like a plug-and-play startup that could be gone after a bad quarter or two. That gives me a little pause. Colorways are sad and depressing – I’d look for something that’s olive or grey versus black.

Lastly, Topo is still very much in the mix! They’re a local company and obviously I can check out their bags easily in person at their flagship. There’s a joy and spirit in their stuff that makes me happy and that’s not worth nothing. They have a couple of offerings that lean a bit more subtle.

Contender 1: Topo Rover Pack Tech (RPT)

So yes, I first went to Topo’s flagship and checked things out. Topo’s entry in this category is the Rover Pack Tech. Based on the Rover Pack, this includes a bit more cushioning for a laptop - and both an internal laptop spot as well as an externally-accessible sleeve. The build quality of the RPT is very good, and this is the most subtle Topo bag design yet – everything is monochrome, down to the zipper pulls and drawstring. The only exception is the liner, which remains a daylight florescent yellow. The design is definitely not minimalist; there are a lot of buckles and straps and loops on this thing and I felt decidedly mixed about that.

The bag is stiffer and more structured than my Y-Pack. The RPT is several inches taller than the Y-Pack but not wider – this is a big rectangle. There’s a flap (with a pocket) secured by two buckles, and the top is a drawstring cincher just like the Y-Pack. Straps are nice and thick. There’s an external water bottle spot on either side, and both fit my Kleen Kanteen (but it’s snug.) When wearing it, this bag feels fine. When loaded with my regular stuff it’s not terrible. It sits higher up on the shoulders for me than the Y-Pack does. Loosening a strap and sliding it around to my front is a no go here, so accessing things quickly really isn’t an option.

I struggled with the RPT. The buckle & drawstring keeps things much more secure, but the fabric itself that cinches is far more sturdy and thick than that of the Y-Pack. This makes loud and crinkly in a not-good way. Second, the RPT remains a “you’ve got a big space, have fun” type of bag, so it doesn’t quite provide enough organization. The height of the interior is also pretty tall, honestly, and accessing stuff in it – already a struggle in the Y-Pack – is worse in the RPT.

The overall feel and quality of the RPT is there, but for what I need it’s not quite a fit. At the time of writing, Topo Designs had a few colorways on a deep discount ($65), but even at that price, I feel I’d be compromising too much.

Contender 2: Evergoods Panel Loader Classic (PLC) 20L

I appreciate that Evergoods offers the PLC in sage green. It’s a really nice color – almost green-grey – and it stands out really nicely against the sea of boring bags out there. The overall look of the PLC is understated: just a big front pocket, a little easy-access top pocket, and the main clamshell area. There’s a laptop spot and a couple of interior pockets, for various & sundry. I really like the look of the PLC and the quality and handfeel of the whole thing is just exceptional.

My challenge with the PLC was, well, the fact that the Civic Half Zip exists. It’s been a minute since I had a full clamshell setup and I have to say that it’s not really my favorite. I really do love the organizational spots built in to the PLC – there’s a laptop sleeve, as noted, along with a spot for a notebook and a pen right in front of that. Unfortunately, and very very sadly, my Appointed notebook of choice is just too big for this spot! And no, this model of bag doesn’t have an exterior water bottle pocket. I lived without it for a long time and the PLC helped me verify that yes, I’m done with that and I definitely want a pocket.

Wearing the bag was good, but it was almost a touch too small looking on my frame (and I’m not a tall person) and it was ever so slightly less comfortable when compared to the CHZ. I would hazard to say that if the PLC was slightly larger and had an outer pocket I’d strongly consider it in part due to the color and versatility. But thankfully, Evergoods has another few options, and I came to really like one of them. The PLC is a charmer but not quite the answer for me.

Contender 3: Evergoods Civic Half Zip (CHZ) 22L

That leads me to the CHZ. This is a really lovely bag. I first tried it in black – yawn – but it nails the understated aesthetic that Evergoods clearly has locked up. As the name implies the main compartment of the CHZ zips, uh, halfway down the bag so the front just flaps open. And honestly? It’s a pretty great way to access things. The exterior has a top pocket (it’s bigger than on the PLC – this is where I’ll pop my pocket contents when going through security), and two water bottle pockets. That’s all she wrote. The main compartment has two more zipper pockets, along with the laptop spot. Pretty simple stuff, but there’s enough in terms of pockets to make me question my need for any separate little bags and that is a very good thing.

The size of the CHZ is noticeably “just a bit” more than the PLC which makes sense on paper, but I noticed it most when doing a trial loadout. The CHZ simply has a bit more room to tuck things in, and I can more easily see using the half-zip when keeping this under an airplane seat. Honestly, too, the water bottle holders are something I really missed. I can’t quite access them when wearing it – a trick I could pull off with my old Blogger and its single strap – but swiping the CHZ off to access it is pretty simple. The zippers, both interior & exterior, are of course top-notch; I felt like they were just a bit smoother on the CHZ versus the PLC out of the box. When wearing this bag it also feels a bit better on my shoulders than the PLC, as if things are better distributed. The handles atop this and the PLC are both beefy and very good.

The handfeel and quality of the CHZ are exceptional. This (along with the PLC) feels and looks like a really quality product. The CHZ isn’t soft but it sits in that “not rough but tough” spot. I would extend this to say that it felt like the PLC would need “breaking in”, and – for some reason – I don’t see that being the case with the CHZ. It feels like it’s just ready to go.

I’m honestly wondering if I could go with the limited edition Burnt Orange color, though. Orange is a real commitment, but it looks incredible in photos. Honestly though, when I’m already past “yeah, this is the bag” and just thinking colorways, I think I’ve got my new pick.

The CHZ22 in Action: Initial Thoughts

I went with Burnt Orange. Late in 2023 Evergoods had a closeout sale on this color so I had less to lose at a very reasonable $129. It’s an uncommon, great color. Shortly thereafter the bag came with me on a couple of work trips. Here are my observations.

• The half-zip format is dope. I love it. When in a chair, the front flap can just kind of be open and it’s no big deal; things are highly accessible.

• Fits under an airline seat no problem.

• The top compartment is perfectly sized. It’s smaller than the Y-Pack’s, but – you know – less stuff is less clutter.

• As noted by many, putting stuff in that top compartment does mean the laptop sits “under” what’s in there. That means a slight adjustment is needed to get a laptop in and out. This is not a big deal at the moment.

• The inner mesh pocket is fucking tiny and shallow, but good for a power brick and a couple cables and no more. (I was able to get a MacBook Pro brick, a tiny Anker USB-C brick, and a couple cables in there.)

• Water bottle pockets are excellent and make it easy to get a bottle in and out – one-handed, even for putting back in.

• My standard move to get the bag off is to just loosen the shoulder strap ripcords. Easy and quick.

• When the bag isn’t completely stuffed, the items in the top pockets can kinda hang out over what’s in the bottom, causing a “waist” in the middle. (You can see it in the photo up just a bit.) This isn’t a big deal to me, but it sure could be to some.

• Great weight distribution with the straps and sternum strap. My shoulders felt fine after hours of use.

• Two tiny QC concerns I’ll watch. First, the zipper for the top compartment looks like it’s “pulling” towards the zippers for the main compartment. This doesn’t affect usage, but it looks a little strained. Second, the main compartment zippers do stick just a bit. I’ll drop Evergoods a note on this if things go awry.

• The color is fantastic and unique. Super glad I went with it over black.

All told, the CHZ is an amazing bag and I think it’s a fantastic travel companion. (As of this writing, the orange CHZ22 is still on sale for $129 – but I expect quantities to be limited.)

Workshopping Failure

As with any project worth its salt, the first place to start is to define the vision, goals, and metrics for the effort. This is especially salient for companies taking on product and experience for the first time at scale – we’ve got to have a clear sense of what’s happening before we do it. I recently wrote about roadmaps but want to step back a bit and talk about the work before the roadmap: the strategic goals.

The vision is something that my former colleague Seth Dobbs talked extensively about on an episode of his excellent podcast, Principle Driven Leadership. “Why Vision Matters” is the episode and basically everything I would say about it he would, too, so just go listen and then come back. I’ll be here. https://www.pdlpodcast.com/podcast/why-vision-matters/

One critical part of defining vision and goals is talking openly about failure. I’ve had the pleasure of exploring this space with multiple clients over the years but wanted to share how it helped a healthcare client. I facilitated and led a 2-day workshop that  included people across marketing, IT, design, and patient experience, including C-suite folks; we had a great cross-section. After we got our intros out of the way on the first day I plunged into two big questions: what does success look like on this project, and what does failure look like? The way I positioned this was: “We’ll know we’re successful if, one year from now, we…” and the same for failure.

Everyone got 10 minutes to write down their thoughts on Post-Its. Once the team had written things down, we put them up on a board; I did a brief clustering to see the emerging themes.

The success stuff was solid. Improved NPS. Happier patients. Happier providers. More efficiency. Less IT time updating content. But being in the failure space space with them was fascinating. The biggest fear in the room was: we’ll spend all this time and money on this and be in the same place. No change. Stuck.

I wanted to learn more – I asked why this was a concern and a fear. At the C-suite level it was simple: we know we need to do better. We need to do it and show it. We need to deliver results. Pretty straightforward and understandable. But for the VPs and SVPs in the room, it was about following through with promises; the team had been burned by high-profile projects before that promised the world (digital transformation!) and delivered, well, a few interesting web components at best.

The criticality of this discussion informed the activities in the rest of the workshop and the project itself. We didn’t use the failure fears as a motivator, but we always kept them around – showing up as a refresher in every presentation, in every critique – so we could always ground ourselves in why we were there. And for success metrics, this framework gave the whole team ways to pull in quant and qual to determine how we were performing, looking at the extremes of failure and success to guide how we measured the work we did.

Ultimately, the web strategy was a success. The organization scaled and grew, and the core marketing and IT teams developed new processes and designs with us.

So when it comes to failure and fear, I’m absolutely good to dive into it with people. It’s an important part of collaboration and leading with heart.

Trust the process

Once I was told, “Gosh, you talk about process a lot.”

It’s true. In the absence of clear processes and rationale, I’ll absolutely work to define them.

My work has broadened well beyond “just” design, content, and strategy work to include the work about the work. This initially showed up in business development (BD) or me, when I quickly learned the ropes on how to define offerings and sell them well. It’s a skill I picked up quickly and loved.

When I started in BD my employer at the time was just starting to scale, but didn’t have a lot of repeatable processes in place. I had a lot of questions. When did we follow up with people? How did we prioritize pitches? Did we do spec work? Who was the point of contact? Do we have a standard set of slides we use? Some of these things were answered and some weren’t. So, I worked with my boss at the time to define them. We developed a strong, end-to-end BD process that helped us focus on the important stuff.

And that’s why I talk process so much: the important stuff. Yes, the process is important. But should a designer be spending her time rewriting the way we talk about our work every time we do a pitch? Probably not. Should a strategist change the format of a case study every single time? I doubt it. Do we need to do things like assign a pitch lead? Yes. Do we need to use a few standard credential deck pieces? Yes. We do this because it removes doubt, reduces confusion, and keeps us all focused.

My love of this concept grew as I established and scaled practices and teams. Do we need to redefine how we do a content inventory every time we do it? No. Do we need to redefine our strategic deck format every time? No. How about the way we run a messaging workshop? No. In those cases I worked hard to research and build out the infrastructure, process, and plumbing so we can spend time on more interesting stuff.

In lieu of a content inventory rethink, should we explore and define the bigger audience-driven opportunities for content? Yes! Instead of redoing the deck again, can we just come up with a great story? Absolutely!

Don’t get me wrong: there is immense value in process and repeatability. Immense. That’s why I love it so – the value shows up when the team is focused on the right challenges and the right questions and the right problems.

When to give feedback

When is the right time to give feedback?

My core belief in leading with heart means I build and grow honest, clear working relationships with people. I’m not a huge fan of bottling things up and keeping them in, but there is a real nuance to identifying when to give feedback to someone.

First, what I’ve seen not work: sitting on feedback for weeks or months at a time. It’s a highly detrimental technique. It erodes trust on both sides of the conversation, and it introduces an element of surprise. I once received feedback on a particular client engagement nearly a year after it happened. During that engagement, I worked closely with lead researchers and executives, but heard not a single negative thing about my work. Imagine my surprise 10 months later when I was involved in a discussion about something that had happened so long ago! I wasn’t prepared, but the person giving me the feedback sure was.

Identifying when to give feedback should be led by the type of feedback being given. If it’s hot off of a presentation, for example, and I have feedback about someone’s presentation style… I’ll likely set that up pretty quickly so we can talk through it. (“You did a great job – nice work! Is it okay with you if I share a few pieces of feedback based on what I noticed?” “I’d like to set up time to go over some feedback from that presentation.”) If it’s not heavy feedback, I’ll typically get that scheduled the same day or pretty quickly behind it.

If it’s a larger piece of feedback – say, the strategic direction for a track of work is seemingly off – I balance the urgency of the request with my readiness to give said feedback. If we’re knee-deep in a project and we need to course correct, that’s going to happen quickly. If we’re planning something out in the early days, but I have real concerns about things being missed or not handled within our shared values, I’ll want to do more homework for that conversation. But, because I often work well with deadlines, I’ll get that scheduled with the person in question and work backwards from the date.

As you can see, there’s a real balance and art to determining when to give some types of feedback.

Lastly, if it’s positive feedback? Make that happen IMMEDIATELY. As quickly as possible! When my team has done well with work, or a client call, or a pitch… I’m absolutely right there cheering them on for the work they did.

Roadmappin'

What goes into a good roadmap?

A roadmap needs to answer a few key questions:

1. What are we doing?

2. Why are we doing it?

3. When are we doing it?

A team must rally and center around a roadmap, and stay focused on the work at hand. Referring back to the roadmap, a foundational piece of work, frames a program or project. Let me break down how I address the questions above in a typical roadmap in a typical redesign and replatforming effort.

Now, the end goal of this type of work is usually, “Move us off of our old platform and on to this new one that lets us do cool things.” There are activities and dependencies that need to happen to hit that goal in the “back of house” and “front of house”. In the back of house, it’s things like deciding on a technical platform after – again, AFTER – the business goals, KPIs, and metrics are identified. It also means evaluating the teams doing the work today, ensuring we have the skills and talent and processes to operationalize our design, content, and technical work. It also means inventorying and auditing what we’ve got from a content and experience perspective. These are all very, very important answers to “what are we doing” to set us up for success… so we call them out together.

Coming out of a discovery process, I’ve typically worked with BAs and the team to identify features and functionality that a project needs. That work gets mapped out in a spreadsheet, and – yes – is the backbone of requirements.

The why, as you can see, is intertwined with the above. Before we prioritize our work, we must have research and context to drive decision-making; we want to be able to say why we’re doing something with good data and evidence. My approach on this couples qualitative research on audiences and their needs with identification of all the things we could do from a feature perspective, balanced with an assessment on how difficult each item is and what it means to the business. That drives the working team to a shared understanding of: we’re creating [this] feature, which has [this] user value, which has [that] business value, and it’s [this] hard to do.

This is often where I trot out a foursquare to show the things that are easy with high value (rare, but it happens!) and the things that are hard with low value (always shows up).

That prioritization then informs the sequencing and the actual roadmap. It’s an evaluation of the team we have to do the work, the value of the work, and getting rough estimates on dependencies and levels of effort. For instance we shouldn’t migrate content before a new taxonomy is in place – although I’ve seen the opposite happen and it is dreadful – so the taxonomy creation needs to happen first. Some dependencies like that are clear and simply required. Others are thornier and require discussion and more collaboration. It can help the whole team see what’s ahead and how much work it will be.

The roadmap, at this point, clearly identifies how much time and effort things are going to take as a clear path forward. And, the farther out we go, the murkier it will be. That’s okay; in my own experience, things get weird after 12-18 months. But – critically – we will come back to it and revise it, because the roadmap is not a thing that just goes on a wall or in a deck and is done. It needs to be actively managed.

Starting with the key questions of what we’re doing, why we’re doing it, and when we’re doing it gives a team the power to be flexible in the future.

Open mode & closed mode

Years ago, comedian John Cleese gave a talk on managing and creativity. It’s something I shared with the whole creative team at Gogo when I first uncovered it as it had a big impact on my work at the time. Cleese’s recent stances on many things are very problematic and retrograde, so in lieu of a direct link, I’d like to surface a key point and talk about how it has influenced me.

When it comes to creativity he proposes a clear delineation between “open mode” and “closed mode”. In open mode, no idea is bad or weird. We’re coming together as a team, shaping what we’ll make. Nothing is off limits and no concept too radical to bring into the fold. It’s a highly stimulating and creative space to play in… and yes, it’s play.

“Closed mode”, on the other hand, snaps in once the team has agreed on the way to go. We may introduce new things along the way, but the time to entertain and explore brand new ideas is over. Closed mode is when we do the work. We take the necessary time to drive towards what we’re creating and we keep focused on the win. This all roughly equates with a discovery phase followed on by an execution phase: “What should we do? Great. Now, let’s plan how to do it and go ahead and do it.”

When we’re done with the work we can and should return to an open mode… because that’s the mindset for receiving feedback, making improvements, and viewing our work and others’ in a new light.

It’s a terribly simple framework but I really love it.

I’ve led projects where we’ve had amazing open modes – often coming in the form of discovery workshops and explorations based on data – and it’s a collaborative and exciting time. This mimics the writers’ room philosophy that Michael Schur, creator of _The Good Place_, espouses: best idea wins. I love that, too, because it fosters the idea of openness, of play, of creativity.

Once a project enters closed mode, it’s time to knock it out. As with anything we’re going to make tweaks and adjustments and improvements along the way but we’re continuing on towards those great ideas we started with, and we’re going to do our best work to see them through. Give people the space and time to do the work, and see it through.

In contrast, when I’ve been involved in projects over my career that jump back and forth between open and closed mode I’ve seen team morale and output plummet. One moment we’re agreed on something; the next, we’re obtaining new requirements and questioning our ideas without a plan on how to evaluate them. This can happen for any number of reasons but it is ultimately detrimental to what we’re working on.

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One last note: time is an essential element of all of this. One of the joys of working in a creative-aligned field is that moment when everything just clicks. You have the data, you see the big picture, you get it… and your brain goes, “Oh! OOOOOH.” That’s the beautiful thing we’re looking for. Having time to think, to consider, to work – because it is work – in the open mode gets us there.

Let's talk risk

Let’s talk risk.

A significant part of the work we do as strategists and leaders is risk identification and mitigation. Here’s an example.

As experts we know what happens when, say, we push off content creation & operations work until the tail end of a website replatforming project, after design and development is done. It harkens back to the old way of doing things: make a container for the content and then “just” put the content in… with a mad blitz during QA when content creation and authoring is happening, and no plan to evolve and change things after launch.

It’s a pickle.

So what happens? In my experience, lots of questions about why decisions were made, the constraints, the message and framework, how existing campaigns tie in… lots of basic, essential questions. But also: surprise. We may hear of new, very necessary requirements. We may learn why things were the way they were, too late to do anything about it. There are true risks introduced there centered around rework, increasing risk to the timeline (“Can we still get this done on time?” “What do we need to do in phase 2, which will never happen?”) and budget (“Why do we now need 5 more people to get this done?”) It also brings risk into the team’s morale, which never feels great!

Sounds bad. So how would I mitigate risk in this example?

I would empower the content team to be informed and involved right up front, with strategy, tech, and creative, in defining requirements for the design system. In my experience this approach has been very successful: content working closely with these experts to map out what’s needed and what’s possible. Risk shifts away from getting work done (“Will we have time to do all of this?”) into ensuring people are collaborating well (“When can we talk about achieving our mutual goals?”), which *tends* to be much more manageable.

This framing and positioning allows us to ask better questions. And I like better questions since they get us to better outcomes. So in the end, I view risk identification and mitigation as a path to stronger understanding. It’s essential to doing great work.

Leadership with Heart

I describe my style of leading as “leadership with heart.” Other than a good excuse to use emoji, what does it mean? These are the foundational pillars to the way I lead, manage, and grow people.

First, clear expectations. People deserve respect, and with respect comes a high degree of transparency and accountability. I would never task someone with doing something if we didn’t first talk about what we wanted the outcomes (more on that later) to be. My expectations for quality, timelines, effort, and goals should be clear. If they aren’t, I work to make them clear. This is something that I’ve worked hard to improve on over the course of my career – it’s very important.

Second, building an honest, clear feedback culture. Giving and receiving feedback is a real, great skill to develop. Keeping things close to the vest, or holding on to feedback for a long period of time, festers and erodes trust. Being open to constructive feedback, and being able to give it, is (again) respectful and leads to growth.

Lastly, not giving in to fear. It’s easy to do; fear is a monster. There will be times in a project, in an economy, in a meeting when we are faced and dealing with fear. (It usually shows up as overcompensating, or pulling back – interesting contrasts.) And I am not ashamed nor afraid to call out when we are starting from a place of fear. We name it so we, as a team, can confirm it – and then collectively decide if that’s a good place to start. Starting our work from a place of boldness, of care, of humanity… that’s always going to be stronger.

All of these pillars have grown and changed over time and, of course, there are times when I’m personally hitting the mark better with some than others. But the common threads of respect and care are there, and they’ll always be foundational for the way I lead my teams.

A Brief Note on Analysis

I’ve written before about how the deliverable isn’t the work (although it is work) – getting to understanding is the work. So context is essential as we work through analysis.

So, uh. How do we do that?

For me getting there starts with inputs. What are all the things we need to take into account? Stakeholder thoughts, goals, feelings… sure. Our own lived experiences and professional experiences. Research on customers. Capabilities of the team we’re working with. The broader market and economy and trends. Analytics on site flows, click paths, and performance. Known, existing research on interactions and designs and flows and behaviors. We need to pull all of this together, as a team. That's a first step.

Critically, it is not the last step.

For example, “80% of people from March through May dropped off on this page” is not information – it is data. What makes this interesting? Is this number good? Is it bad? Who the hell knows? Sharing this directly, as is, in any kind of a final context is – from my perspective – incomplete. It is the job of the team to not only absorb this type of input but, critically, state what it means and provide enough detail for someone to take action on it.

That’s where the analysis comes in – inputs and context are essential to doing quality work. Chasing down “why” is foundational to understanding, and when conducting analysis, it’s something I implore my colleagues and teams to do.

In brief, I view analysis as taking data and turning it into usable information.