Quarterly Live Group Demo Watch Now

Sifted logo

Shipping Nightmares, and How to Avoid Them (ft. Jessica Windham)

In this episode, Jessica Windham, CEO of consultancy Solving Work, talks about the burnout logistics professionals face, common causes of workplace terrors, and what shippers can do to work better and feel better.

Leadershipping Podcast
Episode Summary

It’s a scary time of the year for everyone. But with peak season and the GRI around the corner, it’s especially spooky for shippers.

How are they handling stress?

It turns out, not so well. In fact, 69% of logistics pros are unhappy with their work.

In this episode, Jessica Windham, founder and CEO of consultancy Solving Work, joins the show to talk about the burnout logistics professionals face, the most common causes of workplace terrors she sees, and what shippers can do to work better and still sleep at night.

Main Topics:

  • Why logistics roles are primed for burnout
  • The challenges logistics pros face within their own organizations
  • Why poor tech implementations are a common “shipping nightmare”
  • How prioritization can transform a logistics department, especially during peak season

Other resources:



Jessica W, Caleb N


Caleb N  00:10

Hello, welcome back to another episode of LeaderShipping. You know, Halloween is just around the corner I can’t believe it this year has blown by. That also means peak season is right around the corner. The carriers now are calling it it “demand surcharges” instead of “peak season surcharges,” which is kind of interesting. This really is a spooky time of the year for shippers across the country. How are they handling this stress? You know, we’ve talked a lot about relationships with UPS and FedEx and how you might be able to use data to improve both operationally and contractually, we have not turned this conversation too much around to having it be about the logistics professionals themselves. That’s what today’s episode is really going to be about. Sadly, it turns out that a lot of logistics professionals aren’t super happy in their roles. Oddly enough, I think that being in a high stress job, being stuck between a rock and a hard place, what it can feel like sometimes, can result in having it be individuals that aren’t super happy in their role. Today, we’re really excited to welcome a guest that’s working to address this and help shippers work better and work happier. I think that’s going to be the most key part there. Jessica Windham is founder of and CEO of Solving Work. It’s a consultancy that helps shippers transform their people processes, and partners to find, I’d say greater efficiency at work. And as a net result, lower stress and greater job satisfaction. So I think that there’s some really cool things that we can talk about today with Jessica. A little bit of background on Jessica, Jessica spent nearly 20 years in the logistics industry, working for a wide range of consultancy tech style companies, and even some very recognizable names such as Staples, Perry Ellis International and our favorite UPS. So Jessica, welcome to the show.


Jessica W  02:23

Thank you so much for having me. I’m really happy to be here.


Caleb N  02:26

Yeah, well, we are very lucky to have you here, I think this conversation is going to be really worthwhile. And majority of the individuals that listen to this, are those logistics professionals that would say they’re trying to avoid some of those shipping nightmares, and they might not be super happy in their job. So I think there’s gonna be a lot of value for individuals that are listening to this. And, again, thank you for coming on, it’s gonna be great conversation.


Jessica W  02:54

Yeah, I really hope so. And I hope people can find value and maybe take a couple of tips away to have a better peak.


Caleb N  03:01

It’s really right, I think just kind of surviving is where a lot of shippers, mindsets in and switching it. And I’ve been kind of vocal about this, but switching it from stead of just surviving to thriving. There’s a huge difference in waking up and going to your job feeling like you are surviving, versus thriving. And that’s what we’re hoping, you know, individuals get out of this episode. And we get to a point where when the stress is hitting like it’s hitting right now for peak, logistics professionals are able to manage it a little bit better. So here’s my first question for you Jessica: you’ve held a lot of positions and seen a lot of different logistics departments at sea in action. What in your career experience made you realize a need for a company like what you started, Solving Work?


Jessica W  03:58

That’s an amazing question. And the answer, the brutal truth is it’s just a pattern that I have seen repeated not only in myself, but peers, employees partners, and it didn’t matter which side of the table I sat on. Everybody, well intentioned, competent, like normally engaged individuals all hit that burnout point. Between… you know they just get caught in this kind of like logistics doom-loop where it’s disruption further behind disruption further behind, and no matter and it was just, it was a cycle that I continued to see repeated, and I experienced that myself. In my last two leadership posts, I feel like I was able to help my teams rise above. And that was incredibly fulfilling, and kind of exciting. So I wanted to impact more people. And that’s why I moved out and started Solving Work. It’s like, and you’ve talked about this on the podcast a lot: this can be fun. Work doesn’t have to suck. And you can be fulfilled, get the job done and still be able to sleep at night.


Caleb N  05:08

Yeah, I think that’s such a really, I mean, I love it. With all my heart, I really I really do because I talk to shippers every day where I can tell, and they might not come out and say, “look, I’m just not, this is not super fun for me,” but I can tell they’re not having fun at all. And, you know, I can’t blame them sometimes, given the fact of how stressful that logistics position actually is. And how oftentimes, it’s not really understood. Logistics is one of those things that is kind of a black box, and they tend to put it in into the corner and then assign one or two individuals to manage a massive amount of budget and be expected to do some pretty insane either relationship building with the carrier reps, growth strategies within their own business that help them stay up to up to speed with on time delivery percentage and reaching customers faster for less money. But all that really resides on, you know, a team of logistics professionals who tend to not be super happy in their job I there was one stat that in reviewing your website, I mean, prior to us even chatting, the first time I was blown away by – it was that 69% of logistics professionals are unhappy with their work. So why is that? Why is that 69% of logistics professionals are unhappy with their job


Jessica W  06:47

Logistics is primed for burnout. We are the last ones to touch it. There’s no wiggle room left. We are the unsung heroes in the back of the warehouse with no windows and the old computers and all of that as well. But there’s usually negative time to work with by the time that falls into our laps, and we’re pulling off the impossible doing the herculean day in and day out. And whether that’s recognized or not within an organization, it’s going to take a toll. And people want new problems. We solve the same problem day in and day out. That’s that tactical firefighting, that we’re always doing that really burns us out. Because burnout is hopelessness, and when we are in there, and we’re in the trenches, we’re fighting those fires and leadership doesn’t empower us or give us the agency to make the process changes to make the technology changes, or the partner changes that we need to actually get at the root of what’s going on. We eventually disengage. If the leadership doesn’t care, then we stop caring, and that’s when you no longer can have fun.


Caleb N  07:59

Yeah, I really, that resonates so much with me, I think they’re, you know, in conversations that we’re having on something totally different. But that’s, that’s still, you know, data in the transportation world, I talk to shippers that you know, have these gut feelings inside of like, “Hey, I know we should be doing this, or I know I, if I could just get my upper management to see X, Y, and Z. I know I could get this done and really make an impact that I was asked to make or employed to make, or that’s my job.” And I see that without the proper data to back it up – proper, you know, models that you can run with that data that, you know, Sifted does help out with, there’s other companies that do, but it’s really difficult to communicate what you do as a logistics professional, to others around you, especially in upper management that have no background on transportation, they have no clue, they just know that the shipment should show up at a client’s door on time. So I think it’s one of the things that they just they struggle to communicate that through.


Jessica W  09:11

Well, and one of those things is – we all know FedEx and UPS. We all get packages delivered day in and day out. So everyone’s an armchair expert when it comes to transportation. So that’s where I think one of the big challenges in communicating the complexity, is everyone thinks that they’re an expert, and knows how easy it should be without being – and so that’s where the communication pieces and staying organized and stuff really helps the logistics professional, make the kind of communication internally that they need to. But overall, it’s just a very stressful world and that’s never going to change.


Caleb N  09:52

Yeah, I think the logistics burnout really resonates. And the hopelessness that can come from that. On the flip side, and I think this is why I’m so passionate about having fun in transportation is.. if any industry that’s constantly changing, and that is not the same, it’s transportation. And there is something fun about that as much as it’s grueling and difficult to stay on top of, and a challenge, but that challenge to the right person is fun. And as long as you can go about it in the right way, and kind of navigate that through, I think it’s, I think that fun is to be had, and it’s there. So I’m really curious, you’ve got, you know, you mentioned that there’s, there’s the same kind of problems that shippers run into, on a regular basis, just doing firefighting work. What are some of the most common shipping nightmares you’ve encountered when working with some of these departments that you’ve worked with?


Jessica W  10:59

Yeah, so I think my number one is implementing the wrong technology poorly. “These the TMSs that go unused. These are the business intelligence that nobody looks at.” And we spin our wheels, we have a lot of motion in there, we do something, but it’s not the right thing. And then no one ever wants to touch technology, again. And what we needed to have done is invest the time at the front end to really understand the problem that we’re solving, so that we could then like, figure out the problem, sorry, figure out the problem we’re trying to solve, and then find a solution that actually does that, and then invest in the change management to get it over the finish line. And I said the word invest like six times in there, because in order to get the ROI, you have to make that investment on the front end. And what I find is, is because we’re in the tactical firefighting mode, so often we do these big strategic initiatives as like a side project, you know, in the spare time, so they don’t get the attention that they need, and that they deserve, and thus, they’re not successful. And then we’re like, “well, we’re just going to do things the way we’ve always done it.”


Caleb N  12:16

Yeah. And I think that is, the root of the problem that most shippers run into is “we’re just gonna keep doing things the status quo, because nobody gets fired for just doing the things that we’ve always been doing.” And I think it’s those individuals that take a leap on the technology, the worst thing and I’m so happy you said that, because I see that really, as a common thing. When somebody does go outside their comfort zone, they do take a leap into buying technology, thinking “this is really going to make the difference.” They don’t properly vet it, and it’s the wrong tech that they bring in. Oh, man, that is painful. That is super painful. Those shippers have put their neck on the line, they implement a massive TMS with a huge integration. And then it just sits there, or a BI tool that they don’t use, like you mentioned, I think that is such a great call out.


Jessica W  13:11

Yeah, I find it’s, it’s tough, because I know most logistics leaders in the space, they want to do better, they want to move things forward. They really want to make this progress. And it’s difficult. And when they see somebody else, try and fail, like leadership gets, you know, shy of it to move forward. But then, you know, there’s just in tech, it’s the “fail fast and fail forward.” But in logistics, we’re not often given that space. So that’s why we have to take that additional time on the front end, to be more sure to take, to do what we need to do to incorporate those lessons learned but to keep moving forward.


Caleb N  13:58

Yeah, that’s a really powerful soundbite and something I never thought of before, which is, tech fails forward. And you’re totally correct on that they have this kind of reality of fake it till you make it. You can not do that in transportation. You, it doesn’t take you know, much to tick off some of your clientele when you ship product to them. And the idea of experimenting with something especially as important as that final mile delivery. When a client’s saying “where is my product that I ordered from you” and especially when that gap is shorter and shorter means you used to have five to fifteen business days to get product to a client and that client would be okay with that. With Amazon and Prime and this two day window of expectation that when I order a product and it’s not at my doorstep, within two days, you think, “man this company bought this product from his garbage, they can’t get their act together,” which is so stressful for logistics professionals. I mean that Amazon effect is what we call it of clients that are ordering product and are expecting it there within that two day window, which is crazy. That was never a thing before. But I’m really curious, once you discover some of these pain points, whether it’s you know, the root cause of logistics burnout, some technology implementations that didn’t work, etc, you know, what is the process you take, and you actually walk your clients through that process to address and alleviate some of that pain?


Jessica W  15:49

Yeah. So in logistics, I think sometimes, or a lot of the times, it feels like we’re sailing this boat, or ship that has a hole in it. So we’re spending all our time bailing the water out, trying to stay on course. And then also, you know, making sure none of our people drown. And if you’ve ever read the book Atomic Habits, there’s this motion versus action. And so in logistics, we are in motion constantly. And it felt like we’re doing work that doesn’t need to be done. But we’re definitely not doing work that’s moving things forward, that’s getting us those new problems that people want those new problems that are the result of personal, professional, and departmental growth that lead to thriving and engaged, fulfilled teams. So my process starts by plugging the hole. The hole needs to be plugged that is your personal bandwidth, the bandwidth of your team and re engaging them before we go and make these big strategic initiatives, we’ve got to address some of the fundamentals and set this foundation so that you have… you can return the joy and sleep at night and engage in these technology, in these process, in these partner discussions with bandwidth, with joy, from a place of abundance, something like that. And I know that sounds a little too good to be true. But like, it’s about setting that intentionality. And rather than being a Band-Aid, you know, bring in a tool that you actually have time to use. So after we plug the hole, we think about where we want to go, we start to dig in to where the problems are looking at the SOPs, looking at the KPIs looking at where the money is being spent, identifying the gaps when balls drop, like, find a “why” that we can fix. Sometimes, when we’re doing our post mortems or root cause analysis, we find the first “why” that’s external, and move on, you know, really dialing that back and finding the “why” that we can actually fix. And then figuring out what we need to do now that we know where we need to go. So that’s the process. That’s the technology, that’s the partners, filling those gaps with the right solutions. And you know, this is logistics, things are going to continue to go wrong. It’s always going to be stormy waters, but maybe the next time the big supply chain disruption hits, you know, your vote doesn’t have a freaking hole in it. So that’s the methodology with which I like to approach getting better.


Caleb N  18:29

Yeah. And I think getting better starts exactly what you mentioned, plugging that hole. There’s a lot of people that will look externally as shipping managers to be like, “Oh, if I only have this program, or if I only had this software, if I only have this this external solution.” They oftentimes look at it like kind of, “okay, where’s the silver bullet? There’s some magic piece that I’m not doing that if I go to the market and look for it, that I can find it,” where, when it’s really starts with the team that you have, and getting your head above water, I think is so critical. And there’s a lot of people that we talked to that say, “Look, I’m happy to do all this, but right now I’m just trying to keep my head above water on a daily basis.” Solving that first so that they can you know, stop putting buckets in their in their boats to bail out that water, I think is super, super critical. And I think that’s so valuable for anybody that’s listening to this right now. If you’re in logistics and you feel overwhelmed, plug that hole. I think that’s such a great call out. I love that Jessica I think that’s awesome.


Jessica W  19:55

I think that I just saw this on LinkedIn earlier this week that all problems are people problems. Somebody famous probably said that. And I think when we go to implement technology, we think technology will fix the problem. But people fix problems using the technology, the technology is not going to solve a single problem. And, and like when people are looking for the silver bullet, they, they forget that piece or they lose sight of that piece.


Caleb N  20:27

I love that. I think some of the concern that I keep hearing is… it starts about October timeframe, and it goes until January, and that is peak season. And then right on top of that it’s sandwiched with the GRI or the General Rate Increase. And when you’re telling a logistics professional that his or her budget is going to go up 10%, 15%, whatever it is, and you’re starting a brand new year, and oh, by the way, you’re probably getting into your busy season. That is a lot to take on in a short amount of period of time. What is your final advice to shippers to stay sane, and thrive and move forward during I would say as you know, hell quarter, which is Q4.


Jessica W  21:23

if I could only give one piece of advice, it would be adopt a process and I don’t care what it is, today, that helps you manage your inputs of emails, text messages, phone calls, meetings, Slack channel notes, teams things, post it notes, water cooler chat: you need to have all of your inputs so that you can properly prioritize because this is the season of making business decisions about what gets done. And what doesn’t get done. If you don’t have the universe of what you need to be prioritizing, your prioritization is going to get thrown off and it’s going to send you into firefighting mode, way more than maybe needs to happen. So you’re winning, if you set the ball down, instead of dropping the ball, if you’re not organized, you’re going to ride a wave of additional stress for the next three months. Not only you but your whole team as well, because you set the tone. And if I could add maybe a one be it would be let’s decide right now what we’re going to stop doing during peak season, you need more bandwidth. Unless your UPS and FedEx and Amazon and you get to hire peak season staff, you’re gonna have more work than you normally do. So let’s set something down today, let’s decide “this doesn’t need to be done during peak season, it’s not as critical as the other things that are going to come in that we don’t normally deal with.” And then in January, maybe you decide whether you can set it down forever. But at least right now let’s see what we can set down.


Caleb N  22:56

Yeah, control what you can control, right and prioritize that. I think that’s a great call out. I think this has been truly one of the most valuable conversations I’ve had from a logistics professional point of view. And I think anybody who’s listening to this has experienced logistics, burnout, and what that feels like. But yet we are professionals that are looked upon to identify ways to improve to move the organization forward that we work for, to make smarter decisions. And as you put it, Jessica it’s really up to you, us and your team, that supporting you to get some of that work done. I think that is so valuable. And I can’t thank you enough for being on the show. I think this has just been such a great conversation.


Jessica W  23:57

I appreciate it. I really loved being here. This is something I’m so passionate about. So these conversations, they fulfill me and they help me have joy in what I’m doing and and keep moving my boat forward.


Caleb N  24:10

I love it. Well tell our listeners the best place they can get in touch with you how you want them to interact with you and where they can reach out.


Jessica W  24:20

Find me on LinkedIn, I’m super active there. I love to meet new people, especially logistics leaders that are fired up about getting better and moving their teams forward. So check out my content and give me a follow give me a connection. Let’s talk in the direct messages. And also, I have a webinar coming up on October 27. And we’re going to talk all about prepping your personal peak processes. So my advice that I had here, we’re going to spend 45 minutes diving deep into what you could actually do tactically to make that reality.


Caleb N  24:57

I can’t wait to attend that October. 27th Right?


Jessica W  25:01



Caleb N  25:02

Awesome. Yeah, I think it’s gonna be extremely valuable. I am super appreciative of you being on the show. And I think that your insight, and just your communication style is spot on. I think there are so many individuals that are nodding their heads along with what you’re saying, because they have felt that it felt it themselves. So thank you again.  You can find LeaderShipping on all major podcast platforms, Spotify, Apple Podcasts, the rest, be sure you subscribe so you never miss out on a new episode. I think one thing that’s really important is to interact with us. Leave us a rating, a review, if you’d like of what you’ve heard. I think that’s a great way about making sure that if you’ve gotten value from listening to this podcast or other podcasts of LeaderShipping, tell us what you think making sure that you communicate with us. We want to keep providing this or change things if you need us to. You can also view this episode on Sifted’s Youtube channel. I think that’s a great resource as well to see other clips and videos that we have there. If you’re interested in learning more about Sifted, visit https://sifted.com. Thanks again for listening and we’ll catch you on the next one.


Jessica W  25:27

Thank you.

Shipping Insights & Alerts
Get updates and track the things impacting your business most

Decision Support
See how supply chain adjustments pay off before you pay out

Carrier Management
Streamline how you manage your carrier operations and contracts

Business Automation
Let software do what it does better than people can

Discover news, tips, and industry best practices

DIM Weight Calculator
See how DIM is impacting you

Hear from industry experts on LeaderShipping

Case Studies
Learn how other brands use
Logistics Intelligence

Carbon Calculator
Calculate your CO2 Emissions

Download free reports and
expert how-tos

Get a personalized tour of our software

About Sifted
Get to know Logistics Intelligence

Logistics Intelligence
For parcel shippers

Let's get you to the right place!

For parcel shippers

Redirect to Valence Intelligence Login

Not sure if you have an account? Email [email protected].