Daron Roberts

Peter: And just to be clear, you were writing the book from 3:30 a.m. to 5:30 a.m.?

Daron: That’s me. My wife and I, we have five kids, so the spare time is at an all-time minimum in our family, and I have a mild sleeping disorder, and so I’m up at 3:15. So I decided … I usually work out at around 5, do that for an hour, come back, and then I take the kids to school, and I said you know, there’s a great 24-hour coffee shop about a mile away from our home. I told my wife, “I’m going to block off two hours a day. I don’t want to interfere with anything going on at home, so I’m going to do that in the morning.” And 3:30 to 5:30, same coffee shop, same seat, same coffee and blueberry muffin, and I intentionally disabled the Wi-Fi and just wrote for two hours and did that for eight months.

Peter: How much sleep do you get a night? I’m just curious.

Daron: I’m about four and a half to five, and I can function well on four and a half to five, so that’s where I am. Our kids are from seven down to five months, so I can help my wife out too, because I’m already up. So I’ll do a little bit of the burping and all that good stuff, but I usually average about four and a half to five.

Peter: Wow. I’m curious about something that you’ve already mentioned, and that you obviously talk about in the book, which is your pivot from Harvard Law. I think there’s a lot of people who think about changes in their lives or think about new directions for their businesses or teams, and it’s scary. Every organization, if they’re lucky, faces a choice sometimes. They’ve got this cash cow and they need to take a risk on a new product, or you see something changing in yourself or in your organization, you need to pivot. And yet, I think that’s very scary. It’s very scary to move from a route in which you are already successful to making a choice that certainly many in society might question and you might question yourself. Tell us a little bit about how you make that kind of a choice and some of the struggle or challenge that you faced in making those kinds of decisions, to leave Harvard Law and go to the NFL.

Daron: This issue of risk is something that I’m actually putting together a research team here at UT and we’re going to start looking at a little more intentionally. I think that first, I’m the son of a Baptist minister. My dad would take me with him to weddings and funerals when I was very young. I’d watch him preside over funerals, is one of the images that really stuck out for me, and so I’ve had this very real sense of mortality from an early age. For me, I have been very wary of putting things into the future tense, so I’ll do this after retirement or I’ll do this in 20 years, I just felt like I don’t know if that’s a given, and so I’m going to do it now.

I think one thing to really think about in terms of when we’re looking at risk is to sort of shift that time scale and to say okay, more than likely you’ve been putting something off for successive years or months. At some point, you have to hit the go button. Also, too, I think we tend to sort of inflate the “no” or the rejection or the bad experience, and so I’ve really been focused on saying, first of all, the answer’s “no” before I ask, so I’m at least going to go from an expected output of 100% “no” to a 50% “yes”.

Then two, I just think life’s more interesting when we put ourselves in really challenging situations. One thing I always tell my kids is stay in the deep end of the pool, and they’re learning how to swim now, which is sort of my metaphor for if you find yourself in a place where you feel like you are at the top of the heap, then get out of there. I mean, you need to be the first person to get out of there, find new friends, find new environments. It’s tough. I was at Harvard Law, and people were going to work for Scalia and the White House and State Department and big firms, but for me, Harvard Law meant that I could take a gamble. I think a lot of my classmates saw Harvard Law as a confining tool, that they had to go into law, but I thought that’s why I wanted to go there. I was waitlisted four years in a row, so I really wanted to get in, but that was because I wanted the flexibility.

Peter: That’s so interesting. You worked so hard to get into Harvard Law and then you made this decision to, in effect, leave it.

Daron: Yes. Yeah, it’s good, yeah.

Peter: I think that’s a hard pivot for people to make. I hear what you’re saying when you say I don’t want to leave for tomorrow what I could do today, and life is risky in and of itself. Still, to work so hard for something, to get there and then decide the future that I worked so hard for is not the one that I actually want, takes a tremendous amount of courage. I’m curious what you can share about how you well up the courage to make that kind of a choice, and what you could offer to people who are in similar situations where they’re in a situation that’s good enough, that has a lot of promise, and yet there’s this inkling of something else, and what advice you can give them and draw from your own experience.

Daron: I think a couple things. The Dean at the time was Elena Kagan, who’s now on the Supreme Court. I talked with her, and she said, “You know, the last thing that you will find on your diploma when I hand it to you will be an expiration date.” Legal problems aren’t going anywhere. I think this speaks to the point of is the opportunity that you’re looking at a rare one. For me, I wrote 32 letters. I wrote letters to every NFL team. I received 31 rejections, and the Kansas City Chiefs were the only team that said yes. The opportunity to even be a training camp intern … and mind you, Peter, no college, obviously no NFL playing experience … the opportunity to enter the NFL coaching ranks, even at the lowest level, was something rare, as opposed to being the thousandth associate at insert law firm here.

So I think really dissecting as someone who’s looking at a opportunity, is this a rare moment? If it’s rare, like can I really replicate this experience in the future, if the answer is probably not, I think you should lean toward the yes column. That’s one piece.

Peter: Let me challenge you, Daron, on that too, because it wasn’t an opportunity that just happened, it’s an opportunity you sought after. You had to write 32 letters, so it was an opportunity that you created. Now yes, luck is involved and yes, you had a receptive ear in one out of 32, but you took the initiative to make a choice to say I’m going to write 32 letters, which in and of itself says I’m dissatisfied enough with what I perceive to be my future, even though it’s kind of really successful-looking, and I’m intrigued enough at this other thing, I’m going to try it. So maybe one of the lessons here, Daron, is you didn’t sit at Harvard and say okay, I’m going to go coach for the NFL, you said I’m going to write 32 letters, which is not the same thing.

Daron: Yeah, and it’s interesting that you mention this, because I think that I always will say that people, you dream in big picture, you need to execute with laser-like focus. A lot of people don’t ever shift from Microsoft Word to Excel, and this is what I mean. We get stuck in the dream phase, and oh, it would be great to be on the sidelines and hobnobbing with Bill Belichick, but for me, more importantly, I needed to open up an Excel file, get the mailing address for every NFL team, go to every NFL website, look at the bios of every coach, find some connection, write the cover letter, craft the first sentence to sort of tweak it for the coach, buy the envelopes. You have to be very intentional about it and say I’m sending six letters to the AFC West and half of the AFC East on November the 1st.

That’s where I think people miss the boat, is that they get stuck in the TV viewing phase, and they don’t move from Microsoft Word to let’s get into Excel and really plan this thing out and be deliberate. Listen, I coach, I teach 300 students a year at the University of Texas, I’m coaching NFL players who’ve left the league and are trying to transition back in. I coach executives at companies. There’s always this difficulty in going from this big idea to the implementation phase, and that’s where I think I’ve really tried to focus most of my effort.

Peter: It sounds like one of the important things here, too, is that you didn’t actually commit to coach in the NFL, even if you got 10 responses that said yes, that you committed to write the letters. I actually applied to law school, and I wasn’t sure that I wanted to go to law school, and once I got in, I made the decision I don’t want to go to law school. When I was applying, I wasn’t making a decision to go to law school, I was interested and engaged enough to want to go the next step, but that didn’t necessarily commit me to saying I’m going to follow through and go to law school if I get in. One of the things that I’m hearing you say is that in your case you took that 32nd letter and you pursued it, and you went to coach, but you weren’t making this huge pivot in your life at the point at which you wrote the letters, you were committing enough to reach out and explore to the next stage.

Daron: Yeah. The mind is a wandering tool, and oftentimes people will get stuck in the “Well, if I get the job then they’re going to put me with the wide receivers, and I don’t know anything about receivers.” We start to create these scenarios that more than likely won’t come to fruition. I always tell people, you can’t vet the opportunity on the front end. At least put it out there. No one’s going to break down my door and say, “You better report to the Chiefs tomorrow” if they offer the position to me. But they’re also not going to break down my door and say, “Hey, will you come and work for the Chiefs?” if I don’t write the letter.

So I’m a firm believer, Peter, that you just need to give yourself as many options as possible at any given time. Cast a wide net. Don’t be limiting on the front end. Cast a wide net, and then make the best decision based on the opportunities that are available to you.

Peter: Great. I want to shoot a bunch of questions at you, Daron, of things that you mentioned in the book, and I’d love to hear some brief answers around them, because I think they’ll be interesting to people. One is you mentioned that you have been allergic to any suggestion that a person keep a journal, and yet you started to keep one. Briefly, what was your experience about that? Why do you think it was important?

Daron: A couple of things. One, I think it was, for me, to have a phone in meetings would not have gone over well, so I had to really go back to good old paper and pen, and also it was interesting, because I think I was more thoughtful about what I recorded. So I’m a fan now. That experience changed the way that I look at journaling. I do think it’s important for people who want to be more intentional about recording their thoughts.

Peter: You talk about creating tendency files on your competition, understanding why and when they do what they do. That seems like it could be very, very useful for leaders in organizations. Can you explain more about it?

Daron: Yeah. I watched NFL games yesterday on Sunday, and you find in the league that certain coaches, they have tendencies. They’ll go for it on fourth down more than other coaches. They’re going to kick a field goal more than other coaches. I think aside from the sports context, really looking at who your competitors are, even people in your organization, and saying okay, can I start to map out how Cindy or Sam will react to a certain set of circumstances. That helps a leader to really think through okay, what would my response be if this is what we see on the other end.

Peter: It’s this great alternative to personality assessments in organizations, but to really be thoughtful and say, for your colleagues and for your clients and maybe for competitors, I love this idea of saying what are their tendencies. What do they tend to do? How do they tend to operate? And I love the word “tendency”, because you’re not putting them in a box, and you’re not saying this is who this person is. I’m noticing a pattern, and what are the patterns that you notice of the people around you, and then how can you use those in order to build stronger relationships, in order to collaborate more effectively, in order to communicate in a way that gets received? I think it’s such an interesting approach, and I could see why it could be very, very useful for people and organizations.

Daron: Yeah, and I will say this. With my coaching clients, I will say, “Hey, listen, I see you’re going down this road. It looks like this is the way that you’ve responded in the past.” So you can couch it in nice language, so that it comes off as endearing. Let’s think about this as an option, whereas you would probably want to lean here, let’s think about this as another option for you.

Peter: Yes, and I can imagine that you don’t even have to tell them what you’ve observed, but you could integrate it into what you’re saying, meaning if you’re communicating with someone, what you reflect is that you see them. And people want to be seen, so you see them, and you could address the communications in a way in which you have a higher likelihood that they will hear you or work effectively with you, because you’ve been able to see something about them that kind of helps you learn what they respond and react to.
Daron: Yeah, absolutely.

Peter: Here’s a hard one. You talk about staying even, not getting too high, not dipping too low, not showing your disappointment. It makes a tremendous amount of sense, and it’s a great concept. The hard part about it is in practice, which is somebody does something, and how do you not get triggered, and how do you not respond. Just this morning I had a situation where I was with my wife and somebody came up to us. We gave a donation to an organization and the person spoke entirely to my wife and thanked her and completely dismissed me, didn’t even look at me. Now, it’s not a big thing, but I found myself triggered. I found myself thinking, “Huh, I’m very invisible here, and that doesn’t feel good.”

But I noticed that, and the challenge in those situations is not to blow them out of proportion, is not to make a big deal about them, but to stay even, and it’s hard to do. It’s hard to do when you feel something. It’s hard to not respond or react to it. So my question to you is not about the concept or the idea, but in practice, how do you do this?

Daron: It all comes back to breathing. This is something that’s not in the book. I’ve really embraced breathing and inserting pauses as the two techniques to do this, because what happens is that the heart rate starts going up, you’re upset, and already your mind is thinking through what are the verbal responses. At that point, I just have to shut myself down and really put myself in time out and say I’m going to intentionally breathe, and then I’m going to think about how to respond in a better way. This is something that really, to be honest with you, in the NFL or coaching, no one was coming and talking to us about breathing. And this is not something that I was good at, but in practice, and it’s something that I work on with my students, really stopping, breathing and thinking through and pausing does a lot to sort of quell that storm.

Peter: That’s great. I don’t know if you know, but I wrote a book called “Four Seconds”, which is all about that pause, It’s all about that breath and that pause, so that feels really important. You say that if you want to advance, you have to overreach, to become the ultimate party crasher. That seems to come with a risk that you end up getting dismissed. So how do you balance the goal of overreaching with the risk of being rejected?

Daron: I think that for me, it goes back to that calculus that the answer is “no” anyway, so I’m always thinking through, and I’m always encouraging people, you need to be applying for jobs for which you are not qualified. If you can check all the boxes, if you meet all the requirements, this probably isn’t a position that’s going to challenge you. I think at the micro level within an organization, you need to constantly be putting yourself in a position that’s stretching your mental limits. So if you’re on the marketing team, is there a way for me to jump on another project that’s going to really stretch what I know about marketing?

I think it’s just easy for us to always revert to the mean, and we get into this … we’re chasing homeostasis, and we want everything to remain normal. For me, the most rewarding experiences are ones which are tense at times, are challenging, but I come out on the other end and think wow, I really grew because this forced me to think in different directions.

Peter: I can imagine someone might say, “I want a job as the leader of the organization, but I’m totally unqualified to be the leader, so let me actually apply for a lesser job, a job that can get me in the organization, and then I can work my way up.” How do you assess the amount of overreach that’s appropriate or that makes sense versus completely shooting for the stars and missing every single time?

Daron: So for me, I think it’s a matter of is the industry new or not. For me, I’m going from law to coaching, no playing experience, I need to go in at the ground level. No one was going to hire me to be a defensive coordinator of any high school team in America. No industry experience. Different, though, now if I am looking … I’m in academia, I teach, I run a center for sports leadership and innovation, I could probably make a very good case to a company like Nike to bring me in at a leadership position, because I’ve had experience, NFL, University of Texas.

So I think it’s a matter of are you breaking into an industry for which you have no prior experience. You’re probably going to have to humble yourself and take a position lower than you think you should have. Or do I have some bullet points in the resume that fit with the new position? If the answer is yes, then I think you probably have some legitimacy to kind of overreach and go for a position that may not match up with your background.

Peter: That’s great. You make a point, put yourself in a position to make a play, then make a play. Tell me more about that.

Daron: One thing I found was that I walked into this organization, the Kansas City Chiefs, and we had employees everywhere. There weren’t that many people who were just willing to do the work. Everyone likes the idea of the work getting done. Few people like the idea of doing the work, and so I constantly put myself in a position to go from office to office and ask, “Hey, is there anything that I can do? Can I help you out with a project? Do you need me to scout this opponent?” So I think that having that willingness to constantly ask how you can add value is important.

I listen to Gary Vee. He rubs people the wrong way sometimes, and some people love him, but one thing he talks about is adding value. That has to be the focus, and I don’t care if you are a partner in a law firm and you’re 55, or you’re fresh out of college and you’re 21, people who can add value and do it intentionally and with a smile, those people tend to get what they want in an organization. I think you have to constantly ask to add value, and then once you get that job, your focus has to be on delivering.

Peter: Any last pieces of advice you have for listeners, after all of your experience so far of moving from qualified to unqualified to then qualified, learning and developing and kind of getting in there? Any sort of parting words of advice?

Daron: Couple things. People always ask me how do I find my purpose? I don’t have great answers for that. I do think you need to take an assessment of what do you do when you don’t have to do anything. What kind of readings are you consuming? What are you watching? What kind of podcasts are you listening to? There may be a thread there that will give you a sense of what you think you want to do.

The second thing I will say is that you’ve got to be intentional. People talk about it, but you have to get into Microsoft Outlook or Google Calendar and color code different parts of your week, and do an assessment on the front end and the back end as to hey, here are my top three projects. Did I allot the amount of time for those to become successful? So I think being intentional is key.

Last thing, just to reiterate, I just think breathing. I think we don’t breathe enough. We’re scrolling on our iPhones, and we don’t take the time to stop and pause and really reflect. So that would be my third piece of advice. And live life now. It’s not happening tomorrow for sure, so make sure you’re living it today.

Peter: So everybody, as I give these last notes, take a deep breath, maybe take two deep breaths as you listen to me. It’ll be the first step in taking Daron’s advice and putting it into practice. Daron Roberts has been with us. His book is “Call an Audible: Let My Pivot from Harvard Law to NFL Coach Inspire Your Transition”. Daron, thank you so much for being on the Bregman Leadership Podcast.

Daron: Peter, thank you for having me.

Peter: I hope you enjoyed this episode of the Bregman Leadership Podcast. If you did, it would really help us if you subscribe on iTunes and leave a review. A common problem that I see in companies is a lot of busyness, a lot of hard work that fails to move the organization as a whole forward. That’s the problem that we solve with our Big Arrow process. For more information about that or to access all of my articles, videos and podcasts, visit PeterBregman.com. Thank you, Clare Marshall, for producing this episode, and thank you for listening.