Confidently Manage Large, Multi-Month Projects

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From custom built-directories in our private community to eCommerce cart migrations, Andrew has tackled some hairy projects with lots of moving parts. In today’s episode he takes us through his chronological approach to tackling things from beginning to end. You’ll learn about the things that have worked well for him, the missteps to avoid and how to walk away from a project without thinking, “You know, I probably could’ve gotten by with half of the features I wanted.”

You’ll learn:

  • Why you should push your project live when it’s 90% done
  • How to set expectations for the roles your employees will have
  • The importance of playing the quality control role

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(With your host Andrew Youderian of

Welcome to “The eCommerceFuel Podcast,” the show dedicated to helping high six and seven-figure entrepreneurs build amazing online companies and incredible lives. I’m your host and fellow ecommerce entrepreneur, Andrew Youderian.

Hey, guys. It’s Andrew here, and welcome to the eCommerceFuel Podcast. Thanks so much for tuning in to the show with me today. And today, I wanna talk about how to manage big, hairy multi-month stressful projects that have a billion moving pieces, because it can be tricky to do. You know, over the last decade or so, I’ve done a bunch of these, three major redesigns, a blog redesign, four live conferences, two major software projects.

I’ve spent years of my life and six figures in project and developer spend, planning and executing on major projects. So, I thought it be something worth just doing a quick episode on it and telling you what I’ve learned, kind of the strategy I employ and hopefully, may be able to save you some agony and anguish in your next major project.

Thanks To Our Sponsors!

But before we dive in, I wanna give a big “Thank you,” to our two sponsors who make the show possible. First, to Liquid Web who offers hands down, the best place to host your WooCommerce store online, which has an incredibly robust, stable and scalable platform for your WooCommerce store to call home.

One cool thing about them, they have a neat integration with Glew, that’s G-L-E-W, that gives you way more from your analytics. So, so many of us logon to our analytics dashboard, probably Google Analytics, look at numbers, don’t get any actual data and go back to life as normal.

But with Glew, you can understand which of your WooCommerce store products are making you the most money versus sales, automatically calculates your customer lifetime value for you, and makes recommendations on what products to bundled together. Really cool stuff, so actionable insights from your analytics with their Glew integration, which is pretty sweet.

So, if you wanna learn more about them, or get your Woo store on Liquid Web, you can do that at

And then secondly, a massive thank you to Klaviyo, who makes email marketing automation for ecommerce incredibly easy and profitable. And Klaviyo just rolled out a new sign-up form builder, which makes it very easy to create beautiful best practice pop ups and embeds, with some neat new options.

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When Project Managing Makes More Sense Than Outsourcing

So, before we jump in, you know, I think some people might be thinking, “Well, why is it important that I do just project management and learn how to do this well? This is something I should outsource.” And for some people, I think that makes sense.

You know, if you can afford a great COO, or a phenomenal project manager, it may make sense for you to do that. But if you’re at the high six, low seven-figure level, this is something that sometimes doesn’t make sense to outsource either on a financial basis or on just an attention to detail basis, depending on the importance of the project. And this is, we’re talking about big projects here, so these are probably pretty mission critical to your business.

And even if you do outsource it, I think it’s important to go through this process a handful of times so you can manage it better if you do bring people on in the future to do it.

So, I’m just gonna start with a few things I’ve learned, and then we’ll get into the chronological, my chronological approach to tackling these big hairy projects from beginning to end. I have found that I often build out unnecessary features, so when you’re sitting at the very beginning and putting together your scope list of what you want done, a lot of times at the end I’ll realize, “You know, I probably could’ve gotten by with half of the features I wanted.”

Ask Your Developer About The Hard Features To Implement Upfront

I think about, you know, a feature in the directory we’ve built at eCommerceFuel where people…you can go to the Shopify page that has all of our members using Shopify in real time, and you can email all of them and ask questions. That’s something that is a cool feature when I thought about it. It’s not something that necessarily gets used that much.

I would also, especially if it’s a software project, which I mean, most of these are gonna be because we’re all online. I talk to your developer and have them when they’re running through your scope, ask them to tell you if there’s any features that are gonna be particularly difficult to implement.

Sometimes we have a feature list, we get it built out, and after the fact, we find out that, you know, this feature that really wasn’t critical ended up taking 50 hours to implement. And knowing that upfront is a really nice, so that’s something I always ask my developers to run by, if there’s something that takes a lot of time.

Spend More Time on UX, Less on Design

I think it’s more important to spend more time on the UX and less on the design, although I feel like that’s kind of something that we oftentimes get backwards, how is the site, you know, how usable is the site versus how pretty does it look. I feel like I have a tendency, all of us do, to make it look pretty at the expense of UX, and that’s something to keep in mind.

Choosing Contract Vs. Hourly Basis

When I’m working with developers, or really anyone on a long term project, I love, love, love going on a contract basis versus an hourly basis. And a lot of times, this is usually what it’s set up, but it can save you thousands of dollars, because if you get really clear upfront with what needs to get done, you’re not paying if the developer is, you know, going more slowly or if they, you know, if they underestimated what was gonna happen. And plus, you just have some certainty in the deal of what it’s gonna cost.

So, I love for anything, you know, that’s gonna over 30, 40, even or 20 hours, I like having a contract. It makes it easier, and I feel like it saves me money.

It really makes sense, in my experience, to build something from scratch. Granted, highly customized, yes, but I wanna think about like the directories.

Building (Mostly) From Scratch

If you don’t know, when I say the directories, in our private community we have something called the eCommerceFuel directories, and it goes and it scans all of our member sites, all of our member stores, builds a text deck around them that can tell, you know, if somebody’s using Shopify or Yappo, or whatever, ask them to review the software so we have a proprietary directory of non-biased reviews about software.

So, when we were building that, we built the whole thing. And we built it around WordPress because WordPress took care of a lot of user management and things like that. It wasn’t 100% how we would have build it from scratch, but we could get there easily 70% of the way, and it saved us tens of thousands of dollars in development.

The same thing for the job board we launched recently. We customized a WordPress plug-in, and we had to customize it, but it was a great base to start from. So, I hear about people sometimes building their own shopping carts from scratch, and that just…I mean, I’m sure there are cases that make sense, that is not the route that I would advise most people to go down. So, anyway, it’s something to think about.

Prioritize Marketing A New Project

I found that the marketing is almost always more important than the features or the design. Myself included, we almost always, I think, tend to overspend and over-focus on how the site looks and feels, and spend less time on the marketing. So, that’s just something I found to be true. And I’m trying to fight that with my future projects, but it’s something to keep in mind too.

Hold Contractors To The Scope of Things

And in terms of contractors, a few things I’ve learned about working with contractors is hold them to the scope that you write. You know, when you sit down and you have that agreement, definitely hold them to that scope of features, but don’t always ask to go beyond. It’s really easy to get in the middle of a project and be like, “Well, we should add this, and add this, and add this.” Do your best to fight that, because not only will it take you longer to launch, but you’re gonna start annoying your developers.

Pay Contractors On Time

Pay your contractors on time. I mean, if you do this, if you pay them quickly, you will always be at the top of their list of people to work with. They’ll prioritize you. And it’s just a good thing to do. It’s an ethical thing to do. So, pay your contractors on time.

Think about, you know, any time you do a big hairy project, there are things that are not gonna come out like you hope, and you have a choice to either really just draw a line in the sand and whittle away the goodwill in that relationship to get every single thing done to, you know, exact vision that you had in mind at the expense, though, of the relationship with your contractors.

Balance Demands With a Long-Term View

So, I’ve got, you know, I have a relationship with my contractor now who we worked on multiple big projects together with, and there’s give and take there. And if I had burned all of our goodwill in that first project by insisting a couple of things that were really hard and almost impossible to know that would have been very difficult to do from the outset, that they do them and spend another 50 hours uncompensated by them, they probably would not have come back around to do good work on my other projects.

So, balance your demands with your long-term relationships with your contractors.

Start Writing Your Wish List

So, that being said, the high level things I learned, here is the way I approach big projects. Number one, the first step for me is pour a beer, grab some coffee, get absolutely every element of the project you can think of out on paper, or well, you know, Asana or Trello or something like that.

So, if I’m thinking about redesign, I don’t even think about it in terms of different stages, I just start brainstorming and dump everything into a huge massive list. I need to set up my four-to-four redirects. I need to bring over my customer data. I need to update my DNS. Or, we’re gonna have a new logo. Or, I need to figure out… All of the things just, bluh, just exploded on to the paper. And this is something that I would do over the course of many, many sessions.

Have Your Team Add To It

And also have people in your team review it. You’re gonna add to this, as you go through, you’ll forget things, but the more you can get every step out on paper or into your system from the get go, the easier it will be.

Prioritize The Steps

Also, identify the stage, the critical aspects of the project, which ones are really important, ones where you need to be super anal at, you know, reviewing and making sure they’re done well, versus the ones that are, you know, you need to get done, but they’re less mission critical. So, for example, if you’re migrating shopping carts, SEO is huge, unless you’re 100% paid traffic right?

So, you need to make sure that even if you outsource the process of doing all your redirects from one URL to the other, that you are double-checking those, and you feel solid that they’re in a great place.

Write a Features List for Software Work

If you’re doing a lot of software work, this is also the stage where you need to sit down and write a very clear feature set of what you want. It’s easy to skip at this stage because it’s hard, and to just write a few things down and think you can change them later. Don’t do it.

Invest the time upfront to get really clear on what you want, and describe the functionality that you need. It’s even really important because it can save you thousands of dollars. What you put on this list, you can come back to a contractor at the end and say, “Hey, this isn’t done, please go do it.” If you don’t think through everything upfront and you have to add a bunch of other things, you’re gonna be paying on an hourly basis, and it can cost you a lot of money.

After It’s Written Out, Set Timelines

So, step one, get everything out on paper and document it. Step two, set your timelines. So, at this point, I like to go through and create stages. Take everything you’ve created in your massive mind dump and put it into four or five stages. You can create those, you know, those sections, start reorganizing things, and you start to see the project get a lot more shape.

So, you’re also starting to organize based on dependencies, so if you’ve got the, you know, migrating all the products, you can think through, “Well, we need to migrate…,” let’s say someone needs to create the product listing before I have my VA come in and fill in the copy and the images. So, you can start prioritizing at this stage as well.

And at this point, start assigning rough dates for the stages, not necessarily for the individual projects, but for the stages you want, you know, where you wanna set those. Once you’ve done that, look at the, you know, the time, how long do you think it’s gonna take you, and increase that time by anywhere from 50% to double it.

I have almost never, this recent job board project is one exception, but 80% of the projects that I’m on, the big hairy projects I’m on that, you know, we’re talking like three to six to nine months of work time, they almost always go over by 50% to 2X. That’s just the nature of life. And if you’re banking on things going smoothly and on time and faster than you expect, you are living in an alternate universe.

So, 50% to double, to give yourself a realistic idea so that you’re not getting frustrated, so that, you know…That’s the way I go into it. And usually, that ends up being what the reality ends up being like. So, you’ve got your timeline. You’ve got your stages. You’ve got prioritized lists of items. At this point, now you go through and assign every task to a team member. This is fairly straightforward.

Assign The Right Tasks To The Right People

A couple of thoughts, though. Try not to have people with a high skill set doing really menial things. For example, you know, Laura, she’s our community manager, very skilled woman, has a lot of, you know, she’s a stateside employee. I’m not gonna have her…when we did a big migration, I did not have her going through and doing data entry.

That would be a waste of her time. So, that was something that I had, you know, someone on Upwork, or I had a VA take care of, and I had her focus on the high value activities. If you have someone doing something that is much below their pay grade, figure out a way to upgrade them to have them do something else. Focus on the specialties.

Create a Bank of Screencasts for Handing Over Work

This is a great step too, I love this, to think through a lot of the tasks that take up a lot of time, and in a two or three-day stretch, especially if they’re confusing, create a screencast for all the people doing things that aren’t intuitive on how to do this.

So, if that’s data entry for bringing over metadata for a bunch of products, I’ll do a quick screen cast on that and then put it into the task in Asana, and so when I assign it to a VA, bam, it’s right there. They don’t need anything.

All the instructions are there. And if you front load a lot of that work, then you can really streamline, keeping things moving along really nicely.

Add Contractors Into Your Task Management System

And then finally, I try to get my contractors into my task management system as well. So, if you can get them into Asana or Trello, whatever you’re doing, it’s nice to have one place where you can do everything. So, number three, make sure every task is assigned to your team and you’ve got clear instructions how to perform that task if it’s not, you know, already obvious.

Embrace Being Quality Control

Number four, embrace your role as the quality control man or woman. I like to live by the mantra, “Unless you’ve seen something work properly, assume it’s broken.” And this is hard to do because it takes time, right? It takes time to go through and test things. But more often than not, our things are not working the first time.

And this isn’t a issue of people necessarily being lazy or not doing their job right, but there’s a lot of variables. If you’re in software, there’s a lot of debugging that’s, you know, that’s just part of the beast, which there’s a lot of moving parts in any big project.

So, unless you’ve seen it work properly, assume it’s broken. And so the extent that you care and are willing to go through and stress test the project is really gonna determine the final outcome of that project. Have high standards. Your biggest role, apart from setting the vision, assigning priorities and, you know, keeping those things running, is doing quality control especially when your critical features.

So, go back, look at those high level features that are most important, spend 70% to 80% of your time on that, but also, you know, do some spot checks on the other things as well. Quality control is your role when managing this kind of stuff.

Conduct Regular Check-In Calls

Number five, have regular check-in calls. So, I like to…this is something I always do for my businesses. I have a couple of standing calls per week with my team. But when you’re doing a project, have a, you know, have a regular weekly call where you talk about a lot of things at once. You can batch them. So, for small things that are really easy, you can kind of go maybe once a day into your task management software, Asana, Trello, and, you know, give people the quick answers they need to be able to move forward.

If there’s things that require more work, don’t send emails back and forth, you know, where you’re writing huge paragraphs. Consolidate those into a once or twice a week call where you can talk with your team on the phone to really hash those out in a much more efficient manager, or manner, rather. And that’s how I like to do it. Don’t put yourself to death by paper cuts. That’s the way I like to manage those, with regular check-in calls.

Push Your Project Live When It’s 90% There

So, finally, number six is push your project live when you’re 90% ready, because you are never gonna get to 100%. And I don’t know if this is just the nature of massive projects, but it always feels like at the very end of a project you have this list of things that you think you’re done and then it keeps growing, and growing.

And usually, these aren’t mission critical things, right? I’m not saying, you know, launch something with your SEO or redirect is not working properly, or with the course offer not working. But the little things, the aesthetic things, the smaller, less consequential details, just launch it when you’re 90% there, because once you do push it live, chances are a lot of those things will be noticed. If they are a big deal, then you can fix them after the fact.

But at some point, you just have to push it live. So, this is something that, you know, my developers have encouraged me to do, and I’ve come to really believe in it after launching a number of projects.

When you get to 90%, push it live, and the things that are really important, you know, or the small things you think are important, you’ll fix after the fact. If not, there’s a good chance that they’re not mission critical. Plus, those other things, you can fix those along the way. Anyway, try to be good about pushing something into the world when you’re 90%, otherwise, it will double your project time with very little benefit, I feel like, to the end results for your customers.


So, that’s it. So, again, just quickly to summarize: number one, get everything out on paper or in your project management software. Two, set your timelines and then make sure to increase the actual time by 50% to 100% for a reality check. Three, make sure all of your tasks are assigned to your right team members, and make sure you don’t have people doing tasks that are way below their abilities.

Number four, embrace your role as the quality control person, and understand that that is what is gonna make or break a project. Five, use check-in calls versus death by email. And number six, push it live when you’re at 90% ready to rock. So, I hope that helps, love to hear your thoughts on project management, big audacious things that you have built out. You can comment on this at I’d be curious to hear what you have to say.

So, thanks so much, and I appreciate you listening.

That’s gonna do it for this week’s episode, but if you enjoyed what you heard and are interested in getting plugged into a dynamic community of experienced store owners, check us out at eCommerceFuel is the private vetted community for ecommerce entrepreneurs, and what makes us different is that we really heavily vet everyone that is a member to make sure that there are a great fit, that they can add value to a broader community.

Everyone that joins has to be doing at least a quarter of a million dollars in sales via their store, and our average member does over seven figures in sales annually. So, if you’d like to learn more, if that sounds interesting, you can learn more and apply for membership at

And also, I have to thank our two sponsors that make this show possible. Liquid Web, if you’re onto WooCommerce or you’re thinking about getting on to WooCommerce, Liquid Web is who you should have host your store, particularly with their managed WooCommerce hosting. It’s highly elastic and scalable, it’s got built-in tools to performance test your store so you can be confident it’s gonna work well, and it’s built from the ground up for WooCommerce.

And you can learn more about their offering at

And finally, Klaviyo. For email marketing, they make email segmentation easy and powerful. They integrate with just about every cart out there, and help you build incredibly automated powerful segments that make you money on autopilot. You can check them out and get started for free at Thanks so much for listening, and I’m looking forward to seeing you again next Friday.

Want to connect with and learn from other proven ecommerce entrepreneurs? Join us in the eCommerceFuel private community. It’s our tight-knit, vetted group for store owners with at least a quarter of a million dollars in annual sales. You can learn more and apply for membership at Thanks so much for listening, and I’m looking forward to seeing you again next time.

What Was Mentioned

Flickr: Andy Bright

Posted on: August 17th, 2018

Andrew is the founder of eCommerceFuel and has been building eCommerce businesses ever since gleefully leaving the corporate world in 2008.  Join him and 1,000 vetted 6 and 7-figure store owners inside the eCommerceFuel Community.

Double Your eCommerce Business in the Next Year requesting the most effective growth and profitability strategies we've unearthed from 5+ years of studying successful stores.

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