Lesson Eighteen

How to be a good project manager

Because you were the one who wanted to build your website, app, or online business, you’ve naturally inherited the duties of a project ‘manager’.

Whether you like it or not, and no matter how good the professional you hired is, you will still need to do some level of management to communicate your idea along with priorities and goals so your project stays on track.

While a good professional will naturally help do a lot of this, project management can’t fall solely in their hands. For you to create a strong product in the end, you will need to be involved.

The most important thing you can do as a Project Manager is to communicate like a pro. If you don’t understand something 100 percent, that misunderstanding will only multiply when you communicate it to someone else.

You need to do the work upfront to be clear about what you want. This doesn’t mean you need to get all the way down to defining what features will look like. But you should define what you want your product to accomplish.

No matter how you go about building your product, the main responsibilities of a project manager are to communicate goals, document progress, oversee deadlines, and offer feedback so that a quality product can be built on time and on budget.

You’re also going to have to be malleable enough to communicate with different types of personalities. Not everyone communicates in the same way and you need to be able to connect and be clear with each individual member of your team.

One of the biggest misconceptions is that small teams don’t need a process, but I can tell you every project we’ve run without a process—even if there was only 2-3 people on it—we were either late or over budget.

An ideal process is one that establishes clear guidelines for communication, how feedback will be given (over email or in a project management tool), and what the overall expectations are for the project, while leaving enough space to allow the team to be creative and fluid.

Keeping your project on track

So what do these processes and structures look like?

Status, or update meetings, are a great place to start.

Having clear check-in points sets expectations for the team and encourages them to have progress to report. Typically, status or project reports are done on a weekly basis, so pick a day of the week that works for everyone. I used to like scheduling reports on Wednesdays so we had some time to prep each week for the meeting and some time after the meeting to dig into the items discussed.

Inside Crew, we have weekly meetings with members of each department (i.e. Marketing, Design, Development, Ops) that are scheduled for 30 minutes. We also have a full team meeting once a month. This is helpful for keeping the entire team updated on what people are working on and gives us a forum to discuss roadblocks, address questions, and make strategic plans.

Here’s an example of weekly discussion notes you can send to your team:

Date: Oct 23rd 2015
On Call: Adam, Mark, and Cynthia
Topics: Weekly check-in to discuss design developments
Recap: We went over the designs that Cynthia created in the last week of the mobile app. We also discussed when we can kickoff development, which looks like it will happen in the next couple weeks.
Action items:
  • Cynthia will make modifications to the designs by Friday (feedback in Basecamp)
  • Adam will begin setting up his development environment and will be working off the wireframes to set up the app’s backend
  • Mark will research marketing the application once it’s finalized

Even though we’re a bigger company now, we usually work in small teams of 2-3 people. It might seem like these weekly meetings are overkill but they help everyone on each team get a moment to think about all the moving parts of a project. We’re in build mode so often that it can be helpful to take even just 30 minutes a week to pick our heads up and make sure we’re still headed the right way.

Setting up a time each week where you can touch base on the phone or in person will help uncover deeper questions that are important to producing a quality product.

If you’re not a fan of having consistent meetings, a weekly status report is a great way to keep up to date. Then, if there are any issues that need to be discussed, a call can be scheduled.

However, each team will be different, and your specific schedule isn’t all that important. What is important is that you set aside regular time to discuss progress and resolve any issues that have come up.

What tools are there to make this easier?

There are countless tools to help your team communicate so it’s important to discuss what your new teammates are currently using and what they’re comfortable with.

At Crew we use:

  • Slack for everyday messages and conversations
  • Trello to keep track of our tasks and overall project developments
  • Redpen for feedback on designs
  • Invision for product designs that include multiple pages

If you’re looking for some more recommendations, here are some great products to help you streamline communication on your project.

Team communication


A robust chat application. Perfect for general team communication, quick responses and exchanging project files. Find out why we landed on Slack for Crew.
Recommended For: Projects of all sizes. It’s also complementary to most other tools you use.


A multiplatform chat application. Good for general team communication, quick responses and exchanging project files.
Recommended For: Projects of all sizes.

Project Management

Pivotal Tracker

​A project manager built for agile development. Ideal for running and measuring sprints and keeping track of deadlines, milestones, and weekly tasks.
Recommended For: Agile project management. Ideal for teams of any size.


Streamlines team communication and keeps everything for your project in one place; allows for setting milestones and deadlines.
Recommended For: Larger projects with many moving parts. Typically a project that involves a design and development phase with a team of 2+ professionals.


A project management tool based around managing agile ‘sprints’ — great for keeping track of progress, planning tasks, and milestones.
Recommended For: Agile development projects of all sizes. Works great for keeping larger teams (4+) communicating.


A project management tool that’s extremely flexible and can be adapted for a wide variety of use cases.
Recommended For: Projects of all sizes.

Design Feedback


Allows you to annotate designs and create click-through mockups all within a robust project management workflow.
Recommended For: Larger design projects that also involve an element of prototyping.


​ Used for annotating mockups as well as turning sketches into prototypes for easily communicating your ideas.
Recommended For: Creating realistic web and mobile prototypes.


Provides easy annotation and sketching on mockups. Integrates directly with Evernote for easy organization.
Recommended For: Static mockups that need quick feedback.

Red Pen

Perfect, lightweight tool for easy annotation on mockups. Great for simple workflows and landing pages.
Recommended For: Static mockups and marketing websites.

Code Repositories


The most popular code repository for storing and keeping track of changes in your codebase.
Recommended For: All development projects where you want to control who has access to your codebase and visualize individual contributions.


A robust code repository perfect for storing and keeping track of who’s contributing to your project.
Recommended For: All development projects. The advantage of BitBucket is its free private repos and integrations with other Atlassian products (Jira, HipChat, etc…).

How to leave good feedback

With your process and tools in order, your next main responsibility will be to give regular feedback in order to keep your project moving in the right direction. This is an important facet of project management, and one that can often get lost or overlooked when things don’t go as planned right away.

If something looks bad to you it can be tempting to instantly reply with “I don’t like this”. However, this approach usually doesn’t help move the product in the right direction.

Take the time to step back and try to understand why you’re unhappy with the work.

Perhaps there was something in the original project scope that led the designer to go in a direction you don’t agree with? For instance, maybe you said you liked the design of a certain site but the designer incorporated different elements than the ones you meant.

This situation is so common in product development. Here are several ways you can try to give more effective feedback:

  1. Tell the truth

    If something is not good don’t dance around it. However, there are ways to express your dissatisfaction without being rude. Being abrasive and rude can quickly demotivate your team. You’re not Don Draper. Speaking to your team with respect and treating them as peers goes a long way in keeping your project on track and moving forward.

    Sometimes starting with a question can be helpful. For instance, asking the designer you’re working with, “why did you decide to go in that direction?” might provide a reason behind why the design looks the way it does.

    A good designer or developer will never make something intentionally bad. Their livelihood and reputation depends on quality work. By asking questions, you can unpack the reasoning behind why something was done the way it was and move forward.

  2. Give them the good and the bad

    A common tactic in business is to use what’s called a compliment sandwich when communicating something negative. This is where you start with something good about the work, then express what you didn’t like, then finish with another good comment.

    I’ve used the compliment sandwich before and it’s a good formula when the situation actually warrants it. However, this method shouldn’t be used if it’s only to shy away from confrontation. The success of your project always relies on honesty.

  3. Use tenses to your advantage

    Another way to communicate your unhappiness with the work without coming across as attacking the professional you’ve hired personally is to anchor positive attributes in the present tense and negative attributes (what you’d like to change) in the past tense.

    Positive in present tense: You are a great designer, keep up the great work.

    Negative in past tense: I didn’t feel that was a great design.

    If we had said “That is a bad design,” that would have felt much worse than “that wasn’t a great design.” Anchoring what we’d like changed in the past tense makes us perceive it as if we are already moving forward from it.

  4. Use ‘I feel’

    Ultimately, you’re giving your opinion on the work that was done. Prefacing your feedback with ‘I feel’ allows you to express this opinion without presenting it as fact.

    Even just a simple statement like ‘It could be better’, is more palatable when presented as ‘I feel it could be better’. The later opens up the conversation. The former comes off as harsh and judgy.

Here’s an example of a piece of feedback that is saying the same thing, but one is communicated with more tact than the other:

Good feedback

I really liked how the navigation came together on this version of the design, let’s move forward with it. Can you give me some insight into why you designed the hero section the way you did? I feel like we can do a better job communicating our value in the section below the hero. Let’s jump on a quick call this week and make sure we’re on the same page. After that, would you mind seeing if we can come up with another version of this section? I’m really happy with the work so far, keep it up, we’re getting close to a fantastic website!

Poor feedback

I hate the hero section. I don’t know why but it doesn’t work for me. Can you do a couple more versions until we find something we like? I’m disappointed we didn’t nail it the first time, let’s do a better job this round.

The ‘Good Feedback’ example above uses the compliment sandwich, making the feedback ‘easier to swallow’ while also providing clear direction and defining the next steps while keeping everyone encouraged and acknowledging their achievements.

Realizing when you use each method is a learning process, but nothing you won’t be able to pick up on the job.

You are the coach, organiser, and cheerleader

In order for your project to succeed, at times you’ll need to be a coach (overseeing product decisions), an organizer (defining processes), and a cheerleader (who encourages and excites the team to keep pushing forward).

Remember, this is a journey.

You should celebrate the wins and guide your team through the lows at each step of the way. Hold on tightly to your vision and enforce the processes necessary to get there. No one else will do this if you don’t, so be diligent.

In the end, this will show your team that you’re serious about this project, engaged in the process, and willing to put in the effort it takes to make it a success.