Episode: How to Deliver on Deadline

Season 1, Episode 47

Megan Hyatt Miller: Robert Samuelson is a long-time, multiple-award-winning columnist for the Washington Post. He writes on economics, and he has forgotten more numbers and statistics than most of us will ever know. He’s a valuable observer of economics precisely because of the way he always digs a little deeper. He goes beneath the numbers to understand what they mean. He wants to know not just how things work but how people work. So today we turn to Robert Samuelson for advice on the subject of deadlines: why they’re important and how to use them.

Michael Hyatt: Most of us hate deadlines because of the pressure they produce. Who hasn’t complained about a deadline at some point or ignored it or begged to get out of it or stayed up late to meet it? Deadlines seem, well, unfair, arbitrary, a needless obligation in an already jam-packed schedule, but Samuelson knows better.

“Deadlines are essential,” he says. “Because work can be endlessly elastic, nothing would ever get done without deadlines.” He goes on to say, “If this column were not due today, I would be writing it tomorrow. And the next day, and the next. I would write it forever, because there would be forever to write it.” He concludes by saying, “Deadlines may inspire superficial thought, but without deadlines there would be no thought at all.”

Megan: We dread deadlines and even mock them. Douglas Adams, author of the wildly popular book The Hitchhiker’s Guide to the Galaxy said this about deadlines: “I love deadlines. I love the whooshing noise they make as they go by.”

Michael: He wasn’t kidding. At one point, Adams was so far behind on writing a novel that his agent had to lock the two of them in a room for several weeks. That was the only way he could focus on getting the work done. When Adams died at the age of 49, he hadn’t published a novel in almost a decade. His final work was published as a fragment.

Megan: Because he had no deadline, Adams just kept pushing words around until he ran out of time, just as Robert Samuelson might have predicted. Deadlines. Yes, they produce pressure, but they also prompt us to take action. So maybe Samuelson was right. Everyone needs a deadline.

Michael: Hi, I’m Michael Hyatt.

Megan: And I’m Megan Hyatt Miller.

Michael:  And this is Lead to Win, our weekly podcast to help you win at work, succeed at life, and lead with confidence. In this episode, we’re going to show you three foolproof strategies that enable you to deliver your best results on time, every time.

Megan: As leaders, we all have to deliver the goods, whether that’s a big project or a new product. Too often, though, these major initiatives get bogged down in a morass of minutiae.

Michael: Did you just say that?

Megan: I mean, it’s in the script, so I just read it.

Michael: All right.

Megan: Over the years we’ve honed our ability to deliver big results on a tight timeline, and today we’ll share three foolproof actions that virtually guarantee on-time delivery of a product or project. When we’re through, you’ll avoid being stuck in collaboration mode while another delivery date rolls by, and you’ll gain a knack for delivering results that move your business forward.

Michael: I’m excited about the topic of delivering results, particularly deadlines, although I’m a little less excited about the deadline part of it, but I know we need it. I want to come back to that idea of the morass of minutiae. It affects us too. Every business has a million, maybe a gazillion details to manage, and major projects come on top of that. So I think we have to acknowledge up front that producing a major deliverable, whether it’s a project, a new product, or some company-wide initiative, really is tough. From your perspective, Meg, what makes it tough?

Megan: Well, first of all, these things come on top of our regular jobs. Most of us have day-to-day responsibilities that take up all of our time, whether that’s our personnel efforts or finance or operations, and most executives are already putting in at least 55 hours or more, from our research.

Michael: We talked about this last week, this very point of why it’s difficult to create new products, because it comes on top of our existing job. The same thing here about deadlines. The second thing I think we have to say is that collaboration takes longer than you think.

Megan: Oh my gosh. Totally.

Michael: To quote you, things take longer than they do. One of my favorite quotes.

Megan: It’s not original to me, but when I heard it years and years ago I was like, “Man! That is so true.”

Michael: Who said it?

Megan: Just some little old lady I met out in the country one time.

Michael: I think you should take credit for it. No need to cite that reference.

Megan: Well, it was her, so I’ll cite her.

Michael: The bottom line is you have to get input, you have to get buy-in, you have to get multiple approvals, and gaining consensus takes time. Driving alignment takes time. One key player could get distracted and bog everything down. If somebody else is on another project and they’re under deadline, that can impact your deadline because you didn’t factor that at the beginning.

Megan: Well, also we’re generally really bad at estimating how long things take.

Michael: You think?

Megan: Don’t ask me how I know this. We are professional at underestimating how long things take.

Michael: Greg McKeown says in his book Essentialism that you should take everything you estimate a time for and multiply it times 1.5. I think he’s too conservative.

Megan: I know. I do too.

Michael: It’s like double the time.

Megan: Also, the higher the stakes, the more we procrastinate. We know that a big project is really important to our company, so we don’t want to put our reputation or the company’s reputation on the line, and oftentimes our perfectionism or just the weightiness of it really gets in the way of making progress.

Michael: Have you noticed that for some people this is particularly hard? I think this may be related to a personality type. People who just don’t want to commit. They’re hesitant. We used to have a certain web developer, if you remember, who had a very, very difficult time committing to a deadline. I can remember one particular project we were trying to launch out of the gate.

It came right up to the day that we had announced, and he said, “I don’t think I can do it.” I said, “Let me tell you something. We’re going to launch this. I don’t care what shape it’s in, but we’re going to launch this today, no matter what.” Well, he got it in gear and finally, I think, took me seriously on it, and we got it out the door. Hard deadlines motivate a lot of great action, but for some people it’s difficult to commit.

The first strategy is commit to a deadline. This seems intuitively obvious, like, “Well, of course,” but like I said, some people have difficulty with this. We use our SMARTER goal framework, which has built into it that there has to be a deadline. We talk about the outcome, and it’s easy to forget the time-bound part, which is the T in SMARTER. We move into action or development mode without a clear timeline, and that’s a problem.

Sometimes we’re intentionally vague. We say something like, “Yeah, we’ll get it out in the spring or later this year” or “That’s coming out next year.” The problem without a hard deadline is that it just drifts. You take forever. Like we had a hard time when we launched Platform University because that’s what we said: “We’re going to get it out sometime this fall.”

Megan: That was back in 2011.

Michael: Then it drifted into the spring. That’s the problem of not setting a hard deadline.

Megan: I also think the fear of failure is at the root of this, especially if you’re inexperienced or you’re a perfectionist or, like we said earlier, the stakes are high. You just don’t want to commit because you know that it’s possible you’ll fall short, and that, for some people, is an intolerable feeling.

Michael: How do you handle that in your own life? Sort of that balance between setting a hard deadline and making yourself accountable to that, on the one hand, but realizing that you don’t really know what you’re signing up for on the front end, because you don’t know what’s involved in the project, and it’s a little bit arbitrary. How do you think about that?

Megan: Well, I’ve done this a lot at this point professionally, and I have to say, I love deadlines. They’re my friends, I have learned. That’s probably a little bit unique to my personality. On the Kolbe Index that we talk about a lot I lead with my “Quick Start.” Those are people who like to take action first, and not everybody is like that. But I love deadlines. I have found that the resources show up once you commit to a deadline in almost every case.

There are certainly cases where we adjust deadlines when unforeseen things come up, and there’s nothing wrong with that, but more often than not we hit our deadlines because we commit to them, and people just innovate and have breakthroughs and all kinds of things happen that would never happen without the deadline. I’ve just seen this happen so many times that I don’t want to cheat us out of that experience.

Michael: Okay. I want to ask you a question, and I want you to give me a really honest answer. What percentage of your own personal deadlines…? Forget the company for a second, but you. When you have a deadline, what percentage of your personal deadlines do you actually hit?

Megan: I’m laughing because that’s higher. Me on my own without the team is not as effective as me with a team. When I have the team I’m great at leading to deadlines. Myself, I would say, I’m probably like 50 to 60 percent I hit my own deadlines.

Michael: That’s better than I am. I was going to say about 30 percent. I’m almost always late. The thing that saves me is a publicly proclaimed deadline.

Megan: Totally. Those I would say are almost 100 percent.

Michael: Yeah, I’m almost 100 percent, because it’s show time. I have to show up and deliver the goods. Here’s another crazy thing I do with deadlines. I don’t know if you do this. I procrastinate up until the last minute.

Megan: Yeah, me too.

Michael: I used to feel really guilty about this. Like preparing a speech, for example. I just had to speak this last Sunday, because I do a weekly Sunday school class. I keep thinking to myself, “If I could just get a week ahead, if I could prepare this a week in advance, it would be so much better,” but here’s what happens. I’m telling the truth, and I hate to admit this. I’m a little bit embarrassed by this.

I don’t actually start preparing… I might do some reading on Saturday night, but, honestly, it’s not until Sunday morning. I get up at 4:30 in the morning and start working on it. I used to feel terribly guilty, ashamed about that, but one of my coaches said to me that that’s exactly how he functions, and he said, “That’s just how you’re wired, so let it work for you.”

Megan: This is where you have to have self-awareness and leverage the parts of you that work in certain ways for your benefit. The trick is, though, you have to know that you do that and then make space for it. That would be a real problem if you had your calendar solidly booked until right before that happened, but if you know that about yourself you can make sure you block out some time that morning or whatever is your “unpredictable pattern,” which is actually very predictable because you keep doing it over and over. You can make space for that. It can be really helpful.

Michael: Fortunately for me in that example there’s not a lot competing for my time on Sunday morning at 4:30 in the morning.

Megan: Right. So that works out pretty well.

Michael: So I’m able to pull it off. I think it’s important to recognize that, but at the same time you have to build that in. So talk a little bit about how we accommodate me in that with our team.

Megan: For example, we know that before a live event we need to leave space on the content team for iteration. Very often, you’re going to have your best ideas in the few days leading up to that. Now there is a hard deadline. At some point we have to print materials, and then you have to stop; you can’t iterate anymore. We would never want to shut that off and just say, “Well, if you haven’t thought of your best ideas a month out, then we’re not going to incorporate them,” because we would be missing out on your best thinking. That’s kind of how we’ve approached it. Again, your coach has given us some insight that he’s used successfully, so that has been helpful.

So that’s one side of it, and that’s great for individual work you’re doing. If you’re working with a team, it is important when you’re committing to a deadline that you take into account the real constraints of the process. For example, there may be production constraints. There may be content development constraints. There may be other things that take a certain amount of time to do. If you set and commit to a wildly unrealistic deadline, your team is going to hate you after a while. So it’s important that you get input from your team before you commit to a deadline, and that’s part of alignment, which is something you talk a lot about.

Michael: Another thing about deadlines is that sometimes it helps to set a shorter deadline than you think you need.

Megan: Agreed. This is all kind of in tension there together. These things sound contradictory, but they’re not.

Michael: I know. For example, I was trying to solicit endorsements for my new book Free to Focus. I’ve learned this over the years. If you give potential endorsers too much time, they procrastinate and never get to it, but if I create a short deadline, like, “This is due two weeks from now,” amazingly, people get it on their calendar because they feel a sense of urgency, and that urgency drives action. That’s the value of a deadline: it drives urgency. Sometimes shorter deadlines work better than longer deadlines. So, the first strategy is to commit to a deadline. Let’s move to the second strategy.

Megan: The second strategy is make swift decisions. Decision-making is often where projects get bogged down, because each approval or weigh-in can take more and more time, and before you know it, your project is delayed because you’re waiting for somebody to get back to you. This is where bureaucracy can hamper your ability to succeed.

Michael: It’s so true, but it’s not just the external things like bureaucracy; it’s also the internal things. I want to loop back to our personality. Let’s look at it through the lens of the Kolbe.

Megan: By the way, this is called the Kolbe Index. You can look this up and check it out for yourself. It’s a great tool.

Michael: It’s a major tool that we use before we hire people, and we use it in managing our leadership inside the company as well. The Kolbe basically measures how we initiate work. Sometimes people call it striving, how you strive at work, where your energy goes when you’re working. For a lot of people, they initiate work through fact-finding. They have to do their research first. You and I are pretty high on Fact Finder. We score a 7 out of 10 on that, so that’s a part of it, but we are higher on something called Quick Start, which means we initiate action by just getting into the game and doing something…anything…even if it’s a wrong thing.

Megan: Ready, fire, aim.

Michael: So I think your personality comes into play, because people who are high on Fact Finder, that’s their highest thing… I think of Danielle on our team or I think of your mom. They can tend to put off a decision, not make a decision. This is something internal to them. They want to explore all of their options.

If you look at Myers-Briggs, which is another lens, one of the components of that is something they call judging. For me, I’m an INFJ, and the J means I’m high on judging versus something called perceiving. It means I like to make decisions fast, and I like to get them in the rearview mirror, as opposed to… Like your mom. I’ll use her as an example. She wants to have all of the decisions in front of her. She doesn’t want to make a decision, because there’s probably one more option she hasn’t explored.

I think this is where, as leaders, we come back to this idea (in fact, I think this was the very first episode we did of Lead to Win) of the importance of being self-aware. You have to be aware. If you have a tendency to procrastinate because you need some more research, here’s the issue: the point of absolute certainty is never going to come. You’re never going to be able to do enough research to take the risk out of the decision.

Most decisions you can recover from. They’re not so final. Maybe if you’re a hang glider or a base jumper… Jumping off a cliff can feel pretty terminal. You want to get that decision right. But for most run-of-the-mill decisions we make, they’re recoverable. We just need to make a decision and not hamper the process or slow it down.

Megan: Another way we get in our own way of making these swift decisions, which is so critical for meeting deadlines, is that we over-collaborate.

Michael: That’s a great way to phrase it.

Megan: We’re using consensus building or something like that to keep us from having to make a decision, and it just becomes slower and slower and slower. What we’re not saying is that you shouldn’t incorporate the input or feedback from your team, because that’s a critical component of making good decisions, but you need to do it in such a way that it’s in a defined period and you’re able to move on to a decision. It’s good to have a smaller group of decision-makers instead of decision by committee. That almost never goes well.

Michael: I want to come back to something you kind of said but went over pretty quickly. That is, this can be a subtle way of transferring accountability. I’m no longer accountable for the result; I’ve transferred that to the committee, and they bear the responsibility. You can’t do that as a leader.

Megan: Absolutely not. Okay, let’s talk about how you can speed up your decision-making. Some of this is in our book No Fail Meetings. For every meeting ask, “Is this meeting necessary?” There are often way too many meetings when you’re pursuing a deadline. “Who has to be included and who doesn’t? Whose approval is needed versus desirable?” By the way, it’s good to differentiate between approval and alignment. Getting approval is like permission, but getting alignment is getting everybody on the same page. I think sometimes we confuse those things. Where alignment would do we seek approval from everybody, and it can really slow down the process.

Michael: It can definitely slow it down. Another important aspect of this is set deadlines on the review process. Never ask for a review with an open timeline, like, “Whenever you can get to this.”

Megan: “Can you take a look at this?”

Michael: One of the tricks I’ve learned to use is what I used to call in writing direct-response copy the negative option. This is basically like you subscribe to a program, and unless you intervene and stop the subscription you’re going to keep getting this for the rest of your life. Basically, what I like to say is, “Here’s the deadline. If I don’t hear from you by that deadline, here’s what we’re going to do.” Now all of a sudden you’ve said to them up front this is the course of action you’re going to take if they don’t respond. That’s a great way to promote action or get permission implicitly to take action if they don’t respond.

Megan: Another thing I like to think about when I’m considering decisions is “What’s the best and worst-case scenario if I make this decision?” In other words, I’m looking at what the trade-offs are. If I make no decision, if I procrastinate the decision, what’s the best and worst case of that, and then what’s the best and worst case if I go ahead and move forward with the decision I think I want to make? That usually helps to bring some clarity.

Another thing I love is something I learned from Martha Beck: to project yourself into the future and ask the question, “If I go ahead and make this decision I’m contemplating, do I feel relief that I’ve made it or do I feel regret?” What’s the feeling I have when I stand in the future and look back? If I feel relief, then the tension I feel around making the decision in the present is probably just the uncomfortable feelings or the hassle or whatever is in the way, but it’s not really ultimate. The decision is still good. If, however, I feel regret, then that’s something to pay attention to, because that’s not what you’re going for.

Amy Porterfield: Hi there. My name is Amy Porterfield, and I’m the host of Online Marketing Made Easy. The way you know you have enough to launch, that minimal viable product you can run with, typically happens when you’ve done some research with your audience. What I mean by that is I always encourage my students to do phone calls, and not just on your cell phone, but get on Zoom or Skype and talk to your ideal customer avatar, because so much is said with the nonverbal as well.

You get on a call with them, and you can see their face and they can see yours, and you ask questions. You really start to listen to…What have they tried before? What have they done? What hasn’t worked for them? What have they paid for? What would they be willing to pay for? What do they need? You have to ask the questions that help you understand where they are now and where they want to go. This helps so much knowing if you’re on the right track and you can launch or if you might need to go back to the drawing board and do a little bit of work.

Megan: Amy Porterfield just talked about minimum viable products, which is a great setup for the third strategy.

Michael: The third strategy is to ship in beta. This idea comes from the world of software development. Alpha is the first version, and that’s basically what you do to test in-house. You build the software and test it with your team, try to ferret out as many bugs as you can. Then beta is the next generation. The software has all of the complete features. It has survived your internal beating it up. This version is the one that’s often used in demonstrations, and sometimes it’s released to a limited group for real-world testing. It’s complete, but it’s probably going to have some bugs.

We do this with our products. We don’t develop software (at least we don’t do it anymore; we had one software product way back when), but we do this with our products, and that’s how we think about it. If you think about shipping something in beta, it doesn’t have to be perfect. This is where perfect gets so many people hung up. I like what somebody once said: “Done is better than perfect.” Getting it out the door is better than perfect.

The problem is that if we don’t get it out the door we’re going to miss opportunities, and the most important opportunity we’re going to miss is the opportunity to make it better. We can sit in our ivory towers and alpha test with our team forever and never get it right, because we need user feedback. We need people who aren’t us, who don’t have our set of assumptions, who don’t have our worldview to actually test the product and get a sense of it.

Megan: Do you know what’s interesting about this that I was just thinking? We believed this and practiced this for a long time when we were only producing digital products, and that’s really easy to say, because if you have a typo or something doesn’t work you can just log into the website, make the change, upload a new video, or whatever. It’s low cost. There’s no risk.

But we’ve actually done this also with our physical products, which is an area where most people would consider it to be far more expensive and riskier to launch or to ship at a beta state instead of a perfect state. For example, the Full Focus Planner is now in its third iteration. Small changes at this point are being made. It’s probably not ultimately its last one. As we continue to learn and hear from our customers we’ll continue to tweak. That’s true for LeaderBox. That’s just something we have begun practicing with physical products.

Michael: Even live events.

Megan: Definitely with live events. It’s just important to say that you may have some limiting beliefs around this, that you can only apply this principle to things that are cheap and easy to iterate on, and in fact, I can’t think of anything where this isn’t true.

Michael: Well, an example is that certainly in the world of physical products and back when I was in the publishing world… You really worked hard. You had different layers of proofreaders reading stuff, because once it’s in print it’s hard to change, but get this. Thomas Nelson, when I was there as the CEO, was the world’s largest Bible publisher, and if there’s any book you want to get absolutely, positively right it’s the Bible, because a lot of people are counting on it to be right.

I’ll never forget one particular product we published. I don’t know how it ended up in the product, but I think it was in John, chapter 10, and I think it was supposed to say something about “Jesus taught,” and somehow (this doesn’t even make sense) it said, “Jesus slopped.” I didn’t see it.

Megan: Oh my gosh! Face palm.

Michael: We were doing this with a partner organization. I was actually unveiling this product at this partner organization, and I got a call from our managing editor. He said, “I don’t know how to tell you this, but in John, chapter 10…” I was like, “Are you kidding me?” So I had to admit this, but guess what: it wasn’t the end of the world.

In fact, we published an errata sheet with that Bible, and the guy who was the chairman of that board at the time said, “This is going to be a collector’s item.” It’s all about reframing it. I think the important thing here is to shift our focus. If we want products that are truly excellent, that truly meet the needs of the marketplace, and particularly if we want to hit deadlines, we have to be willing to ship in beta.

Megan: So true. When you were talking about that, it reminded me of some research our team shared with me that was done by the Marriott which shows that responsiveness is more important than perfection. They identified three groups of guests. Group A: nothing bad happened during their stay. Group B: something bad happened, but Marriott fixed the problem. Group C: something bad happened, but Marriott did not fix the problem.

The percentage of these three groups that said they would return to stay at the Marriott were as follows. Group A (nothing bad happened in their stay): 89 percent. Group B (something bad happened, but Marriott fixed it): 94 percent. So, more people would come back if something bad happened and Marriott fixed it than if nothing went wrong. Then Group C (something bad happened, but Marriott did not fix the problem): 69 percent of those people would come back.

Michael: I think I know why that is. I have a theory. The way you create wow is you exceed people’s expectations. If you lower their expectations with something that doesn’t go right, now all of a sudden you have an opportunity to exceed their expectations by fixing it. That creates wow. What that really means… Let me see if I get this straight. What that really means is we need to engineer something that’s a mistake or something that’s a problem into the product so we can fix it.

Megan: No, I think you’re missing the point.

Michael: You’re saying that’s going to happen anyway?

Megan: Yeah. But think about all of the times you’ve had a negative experience as a customer and the person who could have fixed it failed to do that, but you could think of a thousand ways they could blow your mind with their amazing solution, and if they had, you’d be a customer for life.

Michael: So true.

Megan: So this feels true to me.

Michael: I want to talk again about personality types and where they get stuck. We’ve talked about Kolbe. We’ve talked about Myers-Briggs. Another test we use and love is the Enneagram test.

Megan: Can you tell, by the way, that we’re a little geeky about this?

Michael: I know. We’re a little bit geeky about this.

Megan: All the tests.

Michael: The Enneagram basically profiles people according to nine different personality types. For people who aren’t into the Enneagram, they can just gloss over this, fast-forward, but for those who are… It’s a super popular thing now. It’s blowing up all over the world. What types of personalities might really struggle with this idea of beta, shipping something that’s not quite…?

Megan: Well, the Type Ones who are the perfectionists.

Michael: Right. That’s kind of obvious.

Megan: They don’t want to be wrong. That’s really difficult. And Type Threes who are the performers. Those people really care about what other people think. They get a lot of their self-esteem and value from the thoughts of others or the opinions of others, so to put something out into the world that might be less than perfect and risk ridicule can be a really difficult thing.

Michael: I am a Type Three, and my worst emotion I could ever experience is embarrassment. I would rather be flogged than be embarrassed. Being embarrassed is really something that drives me. This is why I work much better with a team, because left to my own devices I’m going to make sure that the thing is as perfect as I can make it, because I don’t want to be embarrassed. I think if you know this about yourself (again, it goes back to self-awareness), then you can use a team and rely less on yourself to meet your deadlines.

Megan: Absolutely. To bring this back to shipping in beta, the point with this Marriott story is that we don’t have to be afraid of imperfection. There are opportunities in imperfection to pursue greater excellence for our customers and our clients.

Michael: There’s value in it for us and for our customers.

Megan: Absolutely. So I think we can move forward without fear.

Today we’ve learned that you really can deliver on a big project or product by following three simple strategies: commit to a deadline, make swift decisions, and ship in beta. As we wrap up for today, I just want to remind you that, as a leader, you’re responsible for results. Don’t be afraid to put yourself on the hook. You really can deliver. Okay, Dad. Any final thoughts for today?

Michael: I think we should embrace deadlines and not think of them as the enemy. They really are our friends. They create a sense of urgency for us. They can make sure we finish what we start and that our organization moves forward and we continue to grow.

Megan: If you’ve enjoyed today’s episode, you can get the show notes, including a full transcript, online at

Michael: Thanks again for joining us on Lead to Win. Please subscribe on iTunes or wherever you listen. We invite you to join us next week when we’ll talk about a surprising competitive advantage for any leader: gratitude. Until then, lead to win.