Project management for freelancers

Retrospectives, And How To Ensure Your Business Doesn’t Fall Apart

By Brennan Dunn

Have you ever received an email or phone call from a client with a subject of, “we need to talk…”, or something as equally foreboding?

Raises hand.

As my company grew beyond myself, I found myself needing to stay on top of a number of projects, most of which I had no direct, daily involvement. As the team scaled, my ability to stay on top of each and every concern diluted. I no longer knew everything that was happening in my company.

And this scared me.

So I did what any fledgling manager of a team of developers and designers would do, and managed without managing. I’d monitor our project management software throughout the day, and make a mental note of what was getting done and what was left to do.

Unfortunately, this only told part of the story.

Project management tools, email threads, and so on that revolve around the particulars of a project fail to track the sentiment. It’s up to you to read between the lines and infer how happy your client is (and some clients are more willing than others to directly express their happiness — or lack thereof).

After having gone through a series of “we need to talk” discussions on projects that, on the surface, looked perfectly fine, I knew I had to do something to keep this from happening again.

The world looks much different at 30,000 feet

Have you ever been in a relationship with someone where you talk all the time (“what’d you do today?,” “what do you want to do about dinner?,” “how’d the kids do at school?”) but you never really talk?

It’s easy to do the usual things that you do in relationships, but it takes practice and persistence to focus on the health of your relationship.

The same is true of the relationship with your clients.

We go about our days working for clients or meeting with clients about their projects. Typically, these meetings are focused on more immediate concerns: What’s getting done, what’s up next, questions about this versus that, and so on.

What’s missing is time set aside to talk about the relationship you have with your clients.

Like with any romantic relationship, what often ends up happening is we keep going about our days — getting work done, reviewing in meetings, etc. — but we don’t take the time to actually talk about the relationship as a whole.

We don’t discuss our feelings or our grievances.

We don’t look at our relationship from 30,000 feet above.

Retrospectives: The best way to gauge the health of your projects and your company

Many years ago, I was working alongside Pivotal Labs on a development project.

About a month or so into the project, they hosted a “Retrospective meeting” and invited me to it. At the meeting was one of the principals at Pivotal, the team who was working on the project (on Pivotal’s side), my client, and me.

On the whiteboard were three columns: Happy, Neutral, and Sad.

For the first 40 or so minutes of the meeting, we all went around and openly commented on the things we were happy with and any issues with the project that we had. We then spent some time reflecting on each point and discussing the ones that had to be discussed. Lastly, we came up with a to-do list that addressed any of the negatives.

I’m about to detail out the specifics of the meeting, but before I do that I want to first mention what effect this had on me and the project.

There were a lot of issues I had with the project:

  • The client was overly attached to the project. (He would regularly hold rule sticks up to his monitor to make sure each design was pixel perfect.)
  • I felt like I was being shortchanged since I didn’t work for Pivotal.
  • It would have felt awkward to express these concerns during a routine planning meeting our on a random phone call with my client.
  • But being able to voice my concerns before they became a problem helped ensure that the project continued to sail smoothly along.

How to host retrospectives with your clients

Afterward, when I decided to grow and start my agency, I included retrospectives on my list of musts.

1. Scheduling

When onboarding a new client, we’d create a shared calendar for their project and had everyone involved subscribe to it.

This calendar had our usual weekly progress meetings, but it also had monthly retrospectives. Many of our projects were multiple months in length, so the interval made sense for us. If you regularly work on short projects, then this might be overkill (the next section of self-retrospectives will be useful).

Attending the monthly retrospectives was a requirement. If you wanted to by a client of ours, you had to come. Otherwise, it exposed ourselves to too much risk — risk I didn’t want to deal with.

Our retrospectives were always scheduled for an hour.

2. Collecting Sentiment

The majority of the meeting was dedicated to data collection.

Every participant in the meeting could say anything they’d like, favorable or not-so-favorable, about the project. Nothing was off limits.

Feedback was grouped into three columns:

  • Happy. This is something good, and something we should take pride in. Let’s keep it up!
  • Neutral. We’re doing this currently, but I don’t feel strongly about it. Let’s maybe figure out how we can make this a “happy” thing by next month.
  • Sad. This is bad and needs to be addressed.

Other participants could “upvote” submissions. When retrospectives resulted in dozens (and sometimes even hundreds) of data points, we had to address the most heavily weighted items first. Usually, we’d just add a + (plus sign) next to a submission if someone upvoted it.


Here are a few common examples of Happy items:

  • The client is reviewing work delivered quickly, usually within 24 hours.
  • We’re on track to solve Problem X within the budget.
  • The team is sending over work that needs few revisions.
  • Our project management software is keeping me up to date with everything that’s happening.
  • I think the design is going to really delight the users of the website.

Here are a few common examples of Neutral items:

  • The way we’re onboarding new users is OK, but I think it could be improved.
  • The team is doing a good job at creating, but I’m still not seeing how what I was promised in the proposal I received is being accomplished yet.
  • We want the client to be more active during our weekly meetings.

Here are a few common examples of Sad items:

  • I don’t see how we can get this done within the budget we have left.
  • We have 30 tasks that need reviewing, and many have been in review for weeks. We’re worried that we’re building the wrong thing.
  • The work you’re doing isn’t what I wanted.

You’d expect many of these, especially the Sad, would be brought up sometime during the engagement.

But, often times, they’re left to sit. And over time, they become more of a thorn in the side of whoever has the problem. And they often lead to the 11th-hour “we need to talk” requests.

You want to diffuse any problems as quickly as possible.

3. Analyses

After capturing as much sentiment as you can, it’s now time to analyze.

I usually like to start with the Happy — we want to preempt the “bad” with all the positive elements of the project. There isn’t much to say about the Happy, outside of wanting to make sure that, next month, those same items stay in the Happy column.

But the real work begins when you move to the Neutral column.

Now you’re talking about things that should be improved, and soon things that must be improved.

You want to figure out what prompted the issue. Why does your client think there’s no way you can get everything done in budget? Why do you think that your client could do a little better at reviewing your work?

Everyone needs to be on the same page. The reason the problem is a problem to begin with is usually due to some disconnect; your client thinks one thing, you think another.

Use Socratic Questioning to try to pry out the actual problem if you need to. Sometimes, the presented problem isn’t the actual problem — it’s just a proxy.

4. Act

Finally, you want to end the meeting with a list of to-dos.

Each Sad item should be converted to an action item that somebody — ideally, whoever brought it up — takes ownership of.

If the client is worried about budget, rather than waiting for him or her to actually run out of budget prematurely (and have heads roll), what can you do now to help put that fear to rest?

If you think that your client has their head in the sand and isn’t as involved as they need to be, educate them on what they should be doing different. And get them to stick to it.

Almost all project problems ultimately boil down to poor communication. And there typically isn’t a formal way to actually diffuse these problems. Sometimes, you’ll have a client who will proactively bring up any issues they face before they’re problematic; and other times, you’re too intimidated to voice your complaints.

But your projects are built off of relationshipsAnd like with any relationship, you need to work on it, rather than just live in it. I think retrospectives are a great way of doing that.

Internal retrospectives

You can also use retrospectives to fix your own problems.

My team hosted retrospectives to solve whatever issues we all had with each other. They were a great way to course correct, especially as we grew and I no longer worked from “the floor” but instead had a private office. It wasn’t always easy for some of my employees to approach me directly, but it became a lot easier during retrospectives.

But I don’t have a team. I’m just… me.

Then all the more reason to map out what’s going well and not-so-well in your business!

Try to take some time each month to focus on analyzing your business. What’s Happy? What’s Neutral? And what’s Sad?

Take a sheet of paper and draw three columns, and group each item you come up with into one.

And once you’ve captured these sentiments, analyze and then act on each negative item.

This is YOUR business. It’s vital to make sure that you’re happy, and there’s no excuse in keeping around anything that’s causing you to be otherwise.

Your homework:

Open up your calendar app of choice and add a recurring event, that starts next week. Set the interval to monthly and title it “Company Retrospective.”.

Once you have a retrospective under your belt, come back and leave a comment here with how it went.