Failure and Premortems (7-29-26)

This week I want to kick off a new series focused on failure, and we will start by thinking about why we will fail and premortems.

I have a lot on my plate. (Does that sound familiar?) In order to try to manage this, I keep a Word document with all my key workstreams and anything that requires a significant part of my time. I then prioritize those workstreams and update them on a regular basis.

This week I took an additional step. I fed my priority sheet to Claude, and asked it to deliver the top 10 reasons why I would fail delivering these things based on what Claude knew about my workload and me. It pulled out some great reasons why I might fail including things like, “I will become the connection point and bottleneck for too many things simultaneously.” “The important non-urgent thinking tasks will be put in the background to deal with urgent feeling fires.” “You don’t protect enough unstructured thinking time.” From there, I asked it to give me 3 tangible things I could action on to prevent this and did those.

Let’s make some connections. Most of the time, when we analyze failure, we analyze it once it has already happened. This is useful, however, it’s too late. Instead of doing a postmortem, I did a premortem. I realized I was overwhelmed and the chances of failure were higher than usual. Instead of letting this happen, I attacked it. I asked what would cause me to fail. I defined the problem and then started acting on it. I can’t guarantee this will eliminate failure, but I can say it will increase my chances of success.

The challenge: Will you conduct premortems to identify failure points before they happen?

Bonus- This is the grid I fill out with my workstreams. It’s been pretty helpful.

Workstream	Biz Impact (H,M,L)	Deliverable Grade	Effort Needed (H, M, L)	Priority (A, B, C)	Notes
Insert project/workstream	What is the business impact?	What “grade” does this have to be?	How much effort do you need to put in?	What is the final priority	Insert any relevant notes to explain what this workstream is about and why it might be high priority or why it might take a certain amount of effort

Have a jolly good day,

Andrew Embry

Blog 700! Trade-offs and Rethinking Outcomes

This is blog number 700! Thanks so much to all of you for reading throughout the years. You comments and compliments always make my heart smile. If you ever want to look at old blogs, they are all here Striking Matches – Igniting new ideas and expanding the way we think about things. With all that said, this week is about trade-offs and broadening how we think about outcomes.

A few weeks ago, I was asked to create content for a breakout room during our Marketing Summit (shout out to Todd and Sam for a great job). I had a trade-off to make, because I could have approached this in a couple of ways. Option A, I could have let it be the typical presentation. It would have worked, but it would have been relatively boring and unengaging. Option B, I could turn it into an experience, but I would have to invest more time and energy.

I chose Option B. I invested a significantamount of my time designing and partnering to build an experience focused on driving decisions with AI. I wove a movie theme throughout everything, creating movie posters, scene briefings, scripts, intentionally choosing props, and so many other things to pull this altogether. Most importantly, I found people to work the stations who absolutely KILLED IT with their stories of driving decisions with AI. (The Lilly Market Research crew is pretty special in case you didn’t already know)

Let’s make a few connections. We live in a world where we often think of trade-offs solely focused on the easily measured things like efficiency or ROI. I’m not saying those things are wrong. I’m saying that at times they can be incomplete. At times, overly focusing only on the easily measurable things will cause you to miss out on greater opportunities.

If you only focus on outcomes that can easily be measured, then nothing I did makes sense. Option A would have cost me less time and less resources. Option A would have freed up more time so I could do other things. However, if you broaden your views on what a positive outcome is, then it becomes a different story. Option B and the experience we built created more energy and engagement than Option A could have dreamed of. Additionally, all this time I invested in Option B filled my bucket. It brought joy and unlocked more creativity that is spilling into everything else I touch. Option B took a lot of my energy, but is still one of the best trade-offs I’ve made in a long time.

The challenge: How will you broaden your view on outcomes as you make trade-off decisions?

Bonus- If you want to get meta with this, if you only focus on easily quantifiable outcomes, then it doesn’t make sense for me to write blogs. I can’t quantify if the blogs save time or do anything for the bottom line. I’d like to think that they give people a smile, motivation, and a pick me up when they need it. I like to think they give folks new ways of looking of things. I also know that the writing makes my heart happy, and that counts for something. Combined, those reasons are more than enough to make the corresponding trade-offs to keep writing.

Have a jolly good day,

Andrew Embry

Enabling Trade-offs (7-15-26)

Last week was about making trade-offs in order to avoid burnout. This week is about enabling trade-offs.

The other day my boss did something that was very simple and very effective. I was on an email chain with my boss and someone else. My boss wrote something along the lines of, “You should connect with Andrew on this. Andrew will be wrapped up this week and next week on X.” It was a simple two sentences. It drove home that this was important. It also gave me air cover that he didn’t expect me to move on it right away. He was enabling me to make a trade-off to focus on X, and get to this at a later date. It was a simple two sentences that were powerful and appreciated. Have you ever had a leader give you air cover? How did it feel?

Let’s connect the dots. How often do you hear leaders talk about how we need to make trade-off decisions? I feel this is a constant talking point at most townhalls. Now, how often do leaders enable you to actually make trade-off decisions? How often do they proactively give you the air cover to not do all the things all the time at the same time? This is where things tend to fall apart. It’s easy to say the right things, and much harder to do the right things.

Something I’m trying to do a better job of is ensuring there is more comfort, clarity, and alignment around what can move slow in comparison. The conversation usually goes like this, “The top priorities are A, B, and C. I see you are also trying to move X, Y, and Z. If X, Y, and Z ever threaten A, B, and C, then I want you to know I’m okay with X, Y, and Z moving slower. I’m comfortable with you pausing that work and making that trade-off, so we can nail A, B, and C.” You can have conversations like this if you are officially in a leadership position and even if you are an individual contributor partnering with cross-functional teams.

The challenges: How are you giving your people air cover to make trade-off decisions?

Have a jolly good day,

Andrew Embry

Trade Offs and Burn Out (7-7-26)

This week I want us to pause for a moment to think about the rest of the year, trade-offs, and burn out.

I was off last week, enjoying our summer shutdown. During this time, I made a few decisions about things that would be non-negotiable for the week. For example, I decided that I would get 7k-10k steps in every day. Nothing was going to get in the way of this. Maybe I would trade off sleeping in, so I could wake up and walk first thing. Maybe I’d trade off sitting on the coach relaxing for walking. I was intentional about my decision, and I was intentional about making trade-offs to reach that goal.

Then, work started up again. We are basically 1 week into the back half of the year. Over the past few days I’ve heard people say things like, “We’re already back to the races,” “Back on the treadmill,” “It’s already so busy.” Do you feel this way? I know I do. All of a sudden, achieving those goals became more complicated, because a lot more was on my plate.

Let’s connect some dots. In my time away, I was able and willing to do things for the house, my family, and myself. This filled my cup and made me a better human. As we start up the second half of the year, I can already see that there is more work than I’ll ever be able to do. If I try to do it all, I know I’ll burn myself out. When I burn myself out, I won’t be good for my family, myself, or my work colleagues.

I’m realizing that if I’m not intentional about my goals and the trade-offs I’m willing to make I won’t be successful. If I’m not intentional, I might spend too much time on X project and not enough on Y, when Y is what really counts. If I’m not intentional, I might trade-off my health or my time with my family for getting lost in the daily grind.

Have a jolly good day,

Andrew Embry

How are you communicating your priorities and workload to others? (1-21-26)

Happy Wednesday,

Last week was asked ourselves the challenging question, “How broken am I willing to be to achieve my goals?” This week I want us to explore a question that should help us avoid being broken, and that question is, “How am I communicating my priorities and workload to others?”

I like my boss. He’s a cool dude and pretty smart. However, he can’t read minds. #bebetter Since I know he can’t read minds, this shapes how I talk to him about priorities and workload. Here was our conversation last week as we discussed goals for the year. I started by explaining the major workstreams and the ones I felt would provide the most value. I explained that in our current state I couldn’t do all of them justice. My boss asked me what my top 3 were. I explained, “Project A and B provide the most value and will take the most effort for X, Y, and Z reasons. I need high quality deliverables for A and B. That basically eats up my Q1. I won’t be able to do Project C justice unless I give up sleep and run myself into the ground, or I get some help. Help looks like this…” My boss tells me he agrees with my rankings and that if we can’t get help in that way we will have to push C until later in the year. We established priorities, trade-offs, and now I have the air support to not burn myself out. It was a 5 minute convo, but all we needed to ensure alignment.

Let’s connect dots. As good as my boss is, I can’t expect him to know everything on my plate. #slacker I can’t expect him to understand how long and how much effort everything takes. If my boss would play in radioactive waste, he might develop mind reading powers, but since that likely won’t happen I need to verbalize these things to him. Once I talk about these things, we can shift into problem solving mode where we can make actual trade-offs where we focus on some things and let others go.

Gut check. How often do you give an HONEST assessment of your workload and capacity? For many years in my career I just sucked it up and ran myself into the ground. I was scared to ask for help. I was scared to say that I had too much. I paid the price for this with my health, and it’s not a price I want to pay anytime soon. We can only address a problem if we know it exists.

The challenge: How will you communicate your priorities and workload to others?

Bonus for the leaders: Are you creating the environment to have these conversations? If your people come to you and discuss legitimate constraints and your default response as a leader is “Just figure it out” you’re likely doing more harm than you realize. I hope as leaders we are creating the environment to have these conversations where we can acknowledge legitimate barriers AND be problem solvers.

Have a jolly good day,

Andrew Embry

How broken am I willing to be to achieve my goals? (1-14-26)

Last week we kicked off a series about questions to ask ourselves as we start the year. Our first question was “What one word/phrase will be our north star?” The question this week might be a bit intense and provocative. The intent is to help us think about protecting our mental health by asking this challenging question, “How broken am I willing to be to achieve my goals?”

Over the past few years, I have watched as more individuals have struggled with mental health challenges than ever before. I’ve seen more people go on leave from work because of stress and its negative impact. I’ve heard more people talk about how they were exhausted, beat down, limping, and feeling overall broken. I have also been that person. Last year was the first year in a long time that I didn’t feel I went past the breaking point. I think part of this is because I began the year by asking myself, “How broken am I willing to be to achieve my goals?” and forcing myself to contend with this answer.

How does this apply to work? While the question is admittedly intense, asking how broken I was willing to be was a wake-up call that forced me to contend with the impact of feeling broken and how that affects my role as a husband, dad, friend, and human. While I had allowed myself to go past the breaking point in the past, I realized it wasn’t worth it. If this meant not doing everything or missing out on something, so be it. I would rather be whole and be better for myself and family than be the super stressed hurting version of myself. As a result, I didn’t work myself into the ground. I was more intentional about where I put my energy. I made trade-offs and said no to things. This also led to conversations with my boss where I had to say, “I can’t do X, Y, and Z without sacrificing my heath and family, and I don’t want to do that. Can we align that X and Y are the most important and I can let Z go?” Here’s the other thing that happened, since I said no to other things, I was able to dedicate time and do X and Y extremely well, and in the grand scheme of things that’s what truly mattered. Overall, I managed to have a solid year, deliver a lot of value, and I did this while being whole. I wish this for all of us.

The challenge: We are still early in the year, before you get lost in the shuffle, I’d encourage you to ask yourself, “How broken am I willing to be to achieve my goals?”

Bonus thought/challenge for leaders- I firmly believe that leaders have a responsibility for protecting the health of their teams. The choices we make as leaders can enable people to be healthier versions of themselves OR bury them in impossible work and standards that have detrimental effects. With that in mind, here is the difficult question I’d pose to anyone leading people, “How far are you willing to break people to achieve your goals and/or the team’s goals?”

Have a jolly good day,

Andrew Embry

Leadership and Outside vs Inside Temperature (7-29-25)

Last week was about patching holes vs installing a new HVAC system. This week is about leadership and the temperature outside vs creating the temperature inside.

The first day that our air conditioning stopped working, the temperature only went up a couple of degrees. It wasn’t too bad. Then, as the temperature shot up outside, the temperature inside kept getting hotter and hotter. Throughout this, we tried to do the same things around the house we would normally do like clean, cook, etc. However, we struggled as the environment around us became hotter and we became more tired and irritable. Once the new AC unit was installed it took time, but eventually the inside of the house became cooler even though the outside was hot as ever. Once things were cooler, it was just a bit easier to do all our normal things around the house.

You might be wondering where this is going. Air conditioning does not stop heat. Instead, it creates a space where it’s just a little bit cooler. That cooler space is more manageable, a little more comfortable. It makes it a little bit easier to do the things you need to do. Similarly, good leaders don’t stop the heat. Good leaders don’t have the ability to wave a magical wand and remove all environmental obstacles, internal hurdles, etc. Good leaders do create a space that is a little more comfortable. It’s a space that makes it a little bit easier to do the things you need to do. Maybe they do this by bringing clarity to the situation. Maybe they do this by bringing in compassion. Maybe they do this by making clear trade-offs. If you’re lucky your leader does all these and more. The bottom line is that the best leaders create the spaces where it’s a bit easier to have success.

The challenge: As a leader, how are you creating a “cool” space for people to flourish?

Bonus observation: I see a fair amount of people getting burnt out from always being in the heat. It’s easy to say it’s their fault, because they didn’t prioritize their work, they didn’t make trade-off decisions, they didn’t handle the stress well, etc. I understand there is some accountability on the individual. I would also argue that this is actually more reflective of a leadership failure within the organization/system. If the leader is clear on the vision and makes clear trade-offs concerning what will and won’t be worked on by their team, then this creates a “cooler” environment where it is easier for employees to stay focused on the right things. It’s easier for employees to focus on the value add work and not burn out. If the leader doesn’t make these calls, then they are letting all the heat in from outside, which contributes a lot to stress, burnout, and more.

Positive real world example. I went to my boss a couple of weeks ago and talked about how I was drowning in work, and how I wanted to make sure he and I were aligned on what matters most. His response was, “What are the 3 most important things you need to execute to provide value to the organization?” I told him, and we aligned on those 3 things. Most importantly, he acknowledged the trade-offs. I’d go all in on those 3 things and we’d be okay if everything else was either slow and/or did not get done. Included in the “don’t worry about it pile” were the emails and asks he had sent me about things not related to those 3 key focus areas. When he aligned on the trade-offs, he stuck by that even when some of his requests were now going to be ignored 😉 That’s what prioritization and making trade-offs looks like. That 5 minute conversation and alignment quickly made the temperature cooler. It made it easier for me to focus and do the things I needed to do.

Have a jolly good day,

Andrew Embry

My Mid-Year Reflection (6-25-25)

This entry is focused on a few key lessons I’ve learned from reflecting at the mid-year point. As I reflect, I truly believe this is one of the best quarters I’ve had in life in a hot minute. If you want you can read the attachments, where I noodle on the different aspects of my life. Between the attachment and the lessons below, I hope something inspires you.

Give yourself permission to focus on 1 or 2 key things– This can be really scary, because if you truly focus on 1 or 2 key things, then this ultimately means there are dozens of things you won’t pay as much attention to. Inevitably, those dozens of things will not be done perfectly. This is the scary part. The realistic part is that those dozens of things likely don’t need to be perfect anyway. At work, my main focus was the rollout and adoption of our synthetic respondent tool. I truly believe that giving it the attention it deserved has already led to a lot of great things. Outside of work, my main focus was on my physical health and more specifically lifting/working out on a more regular basis. I was willing to forgo everything else, and my focus on that one area helped me physically get stronger and mentally feel better.
Stop tinkering and just be consistent– This connects to number 1. Even when you’re focused on something, it’s so easy to feel you have to constantly optimize. The issue is that all the effort spent constantly trying to optimize is effort you don’t spend executing. I had to learn to stop tinkering, so I could go execute.
People and vibes matter, so surround yourself with good ones– It’s amazing what the right people and energy can do. I’m so blessed to be surrounded by some incredible leaders and colleagues right now There is no fear here, just excitement to explore and shape a new future. This is my fuel. I’m soaking it in and using it to propel myself forward.

The challenge: Will you set aside the time to reflect? What lessons will ring true for you?

Have a jolly good day,

Andrew Embry

My Q2 Quarterly Review

Rebuild (Q1B+, Q2A)- This is my word/theme for the year. I wanted to make repairs AND extensive changes. I’m giving myself an A for Q2. I built up some positive momentum in Q1 and have continued to capitalize on that. Hopefully, a lot of these things will become engrained as habits.
Mental Health (Q1A, Q2A)- The goal is to feel like I’m in a good, strong, solid mental state. I’m feeling great. I’ve focused in on a few key things that are helping me improve all aspects of my life. There’s a lot to love and celebrate in life right now, and I’m making sure I take the time to celebrate.
Physical Health (Q1B-, Q2B+)- The goal is to build strength, aiming for increasing strength by around 15%. I might have to adjust my strength goals, because I had a bit of a leg injury that will sideline me from heavy lifts for awhile. However, I’ve been more consistent than I have been in YEARS and I’m feeling the positive results. I’ve completed 2 obstacles course races and have a strong lineup of future races!
Family (Q1B+, Q2A-)– My son is 11 and my daughter is now 13. There are A LOT of big emotions every day. I’m proud of how well my wife and I are handling those things. It’s hard to give space to a dragon as it breathes fire, but there is strength in knowing you can stand in the fire and not get burned. The real strength is in walking through the fire to give the dragon a hug. I’m getting better at that each day.
Career (Q1B+, Q2 A+)- The goal is to feel like I’m delivering magic. If this isn’t the best quarter I’ve had at work in a while, it’s definitely been one of the most enjoyable. I told my boss the other day that I’m actively trying to dial my energy down a few notches because I got so much swagger right now it could hurt someone. Lol. In this quarter I watched things that had been over a year in the making come to life and become successful in such a short time frame. That was awesome to experience. The crucial thing is that it’s not just that I’m delivering magic as an individual. It’s that I’m so blessed to be working with different crews who believe in and are all delivering the impossible right now. That kind of stuff fills my bucket. I need to keep surrounding myself with these people and prioritizing what matters most.
Financial (Q1B, Q2B)- The goal is to ensure we are saving/investing money in the right way. I think I’m doing a bit better than Q1, but not better enough to warrant a higher grade. I think that’s okay. We are enjoying life right now.

Electric Currents, Parenting, Leadership, and Burn Out (1-10-24)

As we start off the year and begin to dive back into the craziness, I think we can all agree that we want to make sure that throughout the year we are taking care of each other in order to avoid exhaustion and burn out. With this in mind, I want us to reflect on electrical current, parenting, leadership, and burn out. If you’re in an official leadership position, I hope you read this and seriously consider the themes and implications. Side note, I’m in an official leadership position, and I’m writing this as a reminder to myself more than anything.

Let’s pretend for a minute that I took a lot of heavy power using appliances and plugged all of them into the same surge protector. It might look something like this picture. I’d assume that you’re thinking, “Why would you do that? That is not smart at all. Even though it’s a surge protector, it is not designed to handle that amount of electrical current. You’re going to burn something down.”

Now let’s think of parenting. Imagine that I have an overwhelming list of demands for my kids, and I expect everything on my to-do list to be done perfectly, and this occurs over months. My kids struggle with this workload. When I notice them struggling, I tell them, “You just need to practice some self-care. Take a rest.” However, the workload and expectations stay the same. At this point, I’d assume/hope you’re thinking something like, “You’re being a bad dad. You’re giving them an impossible task that is beating them down, and instead of doing something that could help them you are telling them to fix it themselves. They don’t have the power to fix it themselves, because they don’t control the expectations you are putting on them. You need to do something.”

What does this have to do with anything? The overloaded surge protector that would start a fire was MY responsibility because I chose to route too much power through it. When my kids were struggling and couldn’t fix it by practicing self-care, it was MY responsibility, because I controlled the list of demands and expectations. Why don’t we more consistently apply this same thinking when we think about employee burn out? Most things I read and hear about burn out put the responsibility on the individual employee. We tell them to practice self-care, go for a walk, and get plenty of rest. Why don’t we more consistently look at the leader and hold them responsible for creating an environment that is a huge contributing factor to burnout? The fact is, even if the individual practices the best self-care ever, it doesn’t matter if their work environment is always crushing them into the ground. The individual can have some responsibility, but not all. Leaders have a large portion of responsibility with regards to burn out, because their actions or inactions are the ones that create environments where burn out has a higher or lower chance of being a negative force for employees.

Think about it for a minute. If a leader doesn’t have a clear vision, then all the additional energy trying to navigate the swirl is extra burden on the team. If the leader doesn’t have clear priorities about what work needs to be done, the quality it needs to be delivered in, and the effort it should require, then all of the extra work done on things that isn’t needed puts extra burden on the team. If the leader is not actively driving a culture where people feel heard and valued, then all the extra energy people put in to survive that culture is extra burden on the team. Have you ever been on the receiving ends of any of those situations? I have. I’ve found that once you add up all that extra burden ON TOP of already largely out of reach goals and expectations, you have the perfect recipe for burnout. Have you ever been the leader who hasn’t done those things well? I have. What did you notice? I notice when I don’t do those things well, it puts a tremendous burden on folks that shouldn’t be there, and it sucks their souls.

The challenge: As a leader, what are you doing to create an environment that minimizes the potential of burnout? Asked another way, as a leader are your actions increasing or decreasing the chances of people experiencing burn out?

Have a jolly good day,

Andrew Embry

Stress Fractures and Taking Time to Heal (9-13-22)

Happy Tuesday,

Breaking the rule and sending my blog out on Tuesday. Our topic is taking time to heal.

Last week I mentioned that when the doctor diagnosed me with a stress fracture that he then shared a plan to help me get back to doing what I wanted to do. The first part of that plan was REST. He looked me in the eye and said, “If you continue training and doing what you’re currently doing, you are going to cause more damage. Damage that will be longer lasting. You need to rest. If you need crutches or something we can do that.” He then outlined what I could and couldn’t do for my health. Eventually he gave me a plan to ease into running. It felt weird resting. It felt like I was doing nothing. However, it was the best training move I made, and now I feel better than I have in a long time.

What does this have to do with anything? Think about work for a minute, how often do you give yourself time to recover? How often do you truly unplug and do what you need to heal from a day, a week, a month, a quarter, a year of running HARD? This rest is essential if we want to keep performing at a high level. Now I want you to think of the doctor. He came into this situation and did a few great things. He saw me and my pain. He took things off my plate (no impact on the leg). He offered resources (crutches). Even as I returned to running, he gave me clear parameters on what I should focus on and how long I should run in order to avoid reinjuring the leg. Now think of work. As a leader, are you doing what this doctor did? Are you acknowledging where your people are mentally/physically/socially? Are you seeing their struggle and pain? From there, are you putting a plan in place with clear priorities that removes things from their plate? Are you giving people the appropriate resources and support to do what they are being asked to do? We need these all these things, not only to do our jobs, but to give us the space, freedom, and opportunity to heal and recover.

The challenge: Are you taking the time to heal? If you are an official leader, are you creating the space/culture and are you putting in the support, so people have time to heal and recover?

Bonus: Even if you’re not a leader, as we work on projects, we could all do a better job of finding places and spaces where we can encourage folks to slow down and work at a more suitable pace vs. sprinting on fractured legs. I’m proud of myself, because I recently told a person, “Don’t do any more work. This will wait, and we will be fine with waiting even though it’s late.” I gave them permission and space to recover. I’m also disappointed in myself, because I’ve also ran colleagues into the ground lately with some projects that were overwhelming fires that consumed so much time at work and beyond.

Have a jolly good day,

Andrew Embry