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⚙️ The Ops Playbook #20
Automating Proposals, Macromanagers, and AI to fix Churn

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Read Time: 5.1 Minutes
Good Morning Operators ⚙️
Welcome everyone to another edition of The Bottleneck.
I’m currently writing this with my newborn in my lap.
Being a first-time dad has been an insane experience. Running from appointment to appointment, buying things last minute (she came early so we weren’t 100% ready!), and trying to get in a few hours of sleep has made for a crazy week.
However, that didn’t stop me from making today’s issue. A few bumps on the journey don't deter people like you and me. We live for the rockiness.
Having said that, we have a doozy of an issue today. Hope you are ready. Here's what we are talking about today:
Automating Client Proposals
How to fix being a macromanager
Using AI to identify why customer churn
Let’s do this.

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1. Automate Client Proposals
Insight from Innovating with AI
While building my fuel logistics business, clients would request I send a proposal to begin working with them. (Respond with HELL YA if you wanna hear about this venture).
Naturally, that led me to be elbow-deep in crafting client proposals.
Each proposal was roughly 80% standard stuff with a 20% twist to tailor it to each client.
Now, imagine if I could feed a few client-specific nuggets into a magic machine, and poof – out comes a customized section of the proposal.
After talking to a few friends, I've learned that I could have automated this whole process with Qwilr and Zapier.
Let's dive into an example sheet. The goal is to generate a project summary with ChatGPT based on the easy-to-input data you add to each column.
First, we're going to create a new Zap. This little setup will dynamically grab the values from each column and feed them to ChatGPT.
Be sure to set up to use Zapier to kick off your workflow only when something specific happens.
Say you have a “Status” column. You can set things up so that Zapier springs into action only when “Status” changes to “Ready for Automation.”
This way, you're not setting off alarms whenever a minor change happens in the spreadsheet.
Here is our starting data:
Now, we need a three-paragraph cover letter.
Try using this prompt:
Write a three-paragraph cover letter addressed to [Contact Person]. Express your excitement for starting the new website project for [Client Company] and mention your firm’s experience in the [Company Type] sector.
Then, summarize the project, which include design and development of a new website on the [CMS] content management system, with [Number of Templates] unique page templates and the following extra features: [Extra Features]
Ta da - Now you should have an automated proposal creator!
P.S. If you want the cover letter template too, respond to this email with gimme gimme.
2. Macromanagers
Insight from Dan Hock
Have you ever had a team that you gave the leeway to do whatever you wanted?
Feels great, right? The team feels happy, things seem to be moving, and then bam!
The end-of-quarter review happens, and it turns out that you had terrible results.
But you say, hey let's ignore this quarter. Everyone's happy, so we'll for sure be able to fix this.
Over time though, your team doesn’t improve. You become known for being poor performers because you aren't able to meet metrics.
You might be macromanaging yourself to failure.
While everyone knows of micromanagers, macromanagers, can be silent organization killers.
Macromanagers are managers who provide poor guidance to their direct reports, delay making changes until a crisis arises, or have poor prep levels.
If you consider yourself a macromanagers, consider these steps to adjust your management approach:
Identify Your Fears
The initial step is acknowledging your fears. Understanding the underlying fears is crucial to avoid reverting to old habits.
Micromanagers typically fear their team's inability to produce results. This concern is more pronounced for those who were effective individual contributors and worry that their skills may not translate well into management roles.
Macromanagers often worry about being disliked or facing resistance from their team, particularly when they've been promoted early and are managing a team of peers or those with similar experience levels, potentially leading to feelings of being an imposter.
Understand Your Team
Fundamental to you being a great leader is being able to understand the capabilities of your team.
Considered the best management book ever, "High Output Management," Andy Grove introduced the concept of "task-relevant maturity":
Your monitoring frequency should depend not on your general perception of an employee's abilities, but on their experience with a specific task and past performance on it.
In my experience, it's often evident that a team member is not just capable of a particular task but may excel beyond my own abilities. When you realize this, it is a clear indicator to step back.
Implement an Intervention Framework

Consider the severity of the consequences if a decision goes wrong and your confidence in the correct solution. These two factors together guide your intervention strategy.
Using this framework, be sure to
allow the team to make mistakes, especially in low-risk decisions.
Delegate fully if you're unsure.
If you're confident, let the team explore, providing guidance as needed.
For high-stakes decisions, the approach varies. If you're confident and the team is off track, step in. If unsure, collaborate with the team to gather more information until a clear path emerges.
3. Using AI to Fix Churn
Insight from Eli Weiss
In a previous role, customer retention was a major problem for one of our ancillary products.
If we could figure out how to stem the bleeding, we could increase revenue to meet OKR goals.
Understanding the root causes of customer churn was akin to deciphering a complex puzzle. It's not just about 'fixing' retention; it's about comprehending the layers beneath it.
Take NPS (Net Promoter Score), for instance.
It was our initial compass, yet its limitations soon became clear. Low response rates and its nature as a lagging indicator often left us chasing shadows rather than addressing current issues.
But it wasn't all gloom.
NPS, while basic, offered us a glimpse into our customer's pulse.
I recall a significant revelation: many detractors rated us poorly due to our customer response time. This insight led us to introduce expanding staffing, gradually reducing dissatisfaction.
Then there were the endless hours I spent combing through customer conversations in Zendesk. The tool held a treasure trove of insights, but I only knew one way to review these tickets.
Enter AI and Natural Language Processing (NLP). Imagine a tool that could sift through the chaotic sea of customer feedback, extracting pearls of wisdom with precision and speed.
It's like teaching a computer to decode the intricacies of human language - a task as complex as it sounds.
Tools now can allow you to dive deep into the emotional states, pain points, and areas needing improvement.
We prioritized these insights. We ensured they were not just confined to reports but were a catalyst for cross-departmental collaboration. Regular meetings with the product, operations, and marketing teams became forums for brainstorming.
Collaboration was key.
We broke down silos, encouraging a free flow of information and ideas. Our approach was iterative; we refined our strategies based on ongoing customer feedback.
By combing through our customer tickets, we reduced churn enough to reach a healthy MRR for the rest of the quarter!
4. Organizing Board Meetings
Insight from Michael Girdley
Michael Girdley always has great advice, especially on building your own company. When I read his advice on organizing update meetings, the content hit home.
At Firstbase.io, I used to have to own many different departments. At some point in my tenure there, I was overseeing:
Product
Engineering
CX
Business Operations
Finance
People Ops
Compliance
Growth
Once a week, I would receive semi-organized updates from my teams. Girdleys system is way better.
Girdley will do the following to make sure he has productive meetings:
The department head/CEO will distribute the agenda and slide deck 72 hours before the meeting.
At the meeting, ask if anyone has issues to discuss after talking through housekeeping. Those get added to the Issue Processing part of the agenda.
The slide deck owner will then walk through the deck. Be sure to realize that this deck has already been reviewed. Just need to add color. The slide deck included a goal review for the current and future quarters, financial metrics, and wins for the quarter.
The biggest part of the meeting is discussing issues that must be resolved.
Finally once the meeting is over, the meeting gets rated by each person to understand where the meeting can improve.

Tool of the Week
As I dove into how to consolidate the insights in my Zendesk customer tickets, Syncly stood out to me as a winner.
Tablestakes with a tool like this is being able to categorize and analzye customer feedback with AI automatically.
To me, what I was impressed by was the the customer segmentation analysis that the tool can provide. Imagine being able to tell if one set of customers was upset by a new launch while another group loved it!
Check them out below. They aren’t a sponsor; I just thought the tool was cool.

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