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How I will become a productive generalist in 2020

In the past six months, my job changed from a specialist role to a generalist role, and it is totally different. Context switching has taken on a whole new meaning, and I need a new way to get organized. 

In July, I was in marketing, You might call marketing a specialist role. All I did was marketing. While it's true that I worked in content marketing, then social media marketing, then brand marketing, then redesigning the website, each a specialty in-and-off itself, I still specialized in marketing. It was the only thing I really had to think about at work. 

At the end of July, my job changed to a general manager of a business unit within ServiceRocket. A general manager is a generalist by definition. Now, I need to think about marketing and sales and customer success and support and product and engineering and budgeting and financial planning and organizational structure and team culture and that’s just getting started. 

A general manager is ultimately responsible for running the over all business, very much like the CEO does for the entire company. 

Of course, there are team leaders for each of these domains: product managers and customer success managers and engineering managers and support managers, etc. I don’t have to do it all, but I have to help and spend time on each. 

If there is one thing I knew, going into this job, is that I needed to stop being a marketing person, and start being a general manager. I could not spend most of my time on marketing, even though that would be my natural tendency. 

I needed to get organized and prevent myself from defaulting to marketing, so I: 

  1. Defined the functional domains of work i need to spend time on.
  2. Assigned a single day of the week to focus on that functional domain
  3. Set up Jira (Cloud) with swimlanes and labels to organize my tasks by functional domain. 

Here’s how I am doing it.

Naming each domain

The hardest part of any new job is not learning the new skills needed, but forgetting the old habits you are used to, especially when you have been a specialist. I was a specialist. Marketing. So my instinct is to do marketing. Schedule marketing meetings. Solve problems with marketing. 

To break this habit, I knew I needed to deliberately spend time on other areas of the business. I sat down to define them, and here is what I came up with.

  • Go To Market: This is marketing & sales
  • Customer Success: Everything about the customer, including support.
  • Product & Engineering: Defining, making, building, and monitoring the product
  • Team & Culture: This is org charts, job descriptions, recognition, performance reviews, 1:1s, and all team and people related discussion.
  • Planning & Finance: Budgeting, forecasting, P&L reviews, negotiating subscription renewals for things we buy, head count requests, updating the forecast, updating the forecast, updating the forecast, and more updating the forecast.

Assign a domain to a day for focus

I learned (and quickly accepted) that I cannot multitask. I learned that from from John Medina in his book Brain Rules: 12 Principles for Surviving and Thriving and Work, Home, and School. We switch between tasks. We don’t actually multi-task. When we switch, we lose momentum and productivity falls.  And looking at the above list of domains, it’s obvious I would be switching.

A lot. 

Then I learned about theming my days from two highly productive generalists. Pete Carrollwhen he coached a USC, had themes for practices. For example: 

  • Tell the Truth Monday
  • Competition Tuesday
  • Turnover Wednesday. 

The second source came from Jack Dorsey, CEO of Twitter and Square, who also themes his days. Dorsey's themes: 

  • Monday: Management meetings and "running the company" work 
  • Tuesday: Product development
  • Wednesday: Marketing, communications, and growth
  • Thursday: Developers and partnerships
  • Friday: The company and its culture

So I decided to do the same with my domains. 

  • Monday - Go To Market
  • Tuesday - Product and Engineering
  • Wednesday - Team & Culture
  • Thursday - Customers and Customer Success
  • Friday - Finance & Planning

The question of course now is, "How do I put this into practice?” 

Most of the things I work on have a Jira issue associated with them. And there are many. I knew I wanted to organize my issues in such a way that I could look at all issues for a domain together and make progress on those issues on that day. As you can related, my issues are across multiple projects and teams, and it's hard to keep them all straight. 

Then it hit me.


Swimlanes are my friends

I created a kanban board, which I called uncreatively: Bill’s Master Board. I won’t go into kanban boards or swimlanes more than to say this. I created five swimlanes named for each of my domains, which created a row on my kanban board and displays only the issues for that domain that I want to show up in that swimlane. 

Then, I used labels to define which issues go into which swimlane. I chose labels (instead of components) because labels are simpler and more flexible, and since I wanted to start quickly, labels take seconds to implement. 



Since I am a generalist, many things I work on are cross-functional and not everything I work on even fits in one of these domains, so labels allow me to “label” any issue I want or not label an issue. I try only to put the big important tasks for each domain on this board. 

It’s not perfect, but...

The one thing this helps me with most is reminding me to spend time deliberately on an individual domain for a set period of time. It reminds me that I am not a marketer. I am a general manager. “Today is Thursday. I am working on customer issues and working with our customer teams today.” 

This is not to say I only work on customer issues on Thursdays, but I am getting there. 

My next move

I am going to start only (well mostly) accepting meetings for domains on days I deal with those domains. Sometimes I still take a product meeting (Tuesday domain) on a Friday (Planning & Finance) because that is the best available time for that meeting. This is a slippery slope into ruining the theme for the day. 

I use Calendly to make scheduling meetings simpler. I plan to set up a Calendly event for each domain. If someone wants to schedule a meeting with me about engineering, I will have them book it using the Calendly link for that domain. If the next available time isn’t until the third Tuesday in March, I might have to say, “So be it.” 

I am a little nervous about doing that. But this is a real life example of a kink to work out. 

Being a generalist is hard.

Jira makes it a little easier. 



Nice outline of using Jira for handling all the different kinds of work. Did you consider using Trello at all?

p.s. Just for old time's sake: "over all" should be "overall". Say hi to Rob! 

@Matt Doar__ LinkedIn I have only dabbled with Trello. What prevents me from using Trello, mostly, is the inability to filter multiple projects into one board (or filter, for that matter). I feel like I have a need to see my work across projects without having to go into one and a time. Of course, now that I write this I realize this violates my "I don't multi-task" attitude. 

But that is the main reason. There are others. 

And as for "over all" versus "overall." I would respond with two question: 1) Should? and 2) Who said?

Alison Atlassian Team Jan 30, 2020

Hey Bill, congrats on the new role! Thanks for sharing how you're making your transition easier with Jira. 

Ditto to the comments above - I wonder if you could do a test run with both Jira and Trello and evaluate the pros and cons of each for your use case.

@Alison I think that would be interesting. I might just do that. Though, my Jira skills outweigh my Trello chop. So it will take me some time to think about how'd I'd do it. 

Alison Atlassian Team Jan 31, 2020

@Bill Cushard , Trello has a bunch of templates to help you get started. Their Productivity boards would be good to cheeck out: 

If you hit it off on Trello you might even want to submit your board to become a template to guide others learning multiple domains :) 

Jessica Atlassian Team Jan 31, 2020

@Bill Cushard congrats on the new role and appreciate you sharing this!

I especially loved this sentence. Great insight.

The hardest part of any new job is not learning the new skills needed, but forgetting the old habits you are used to, especially when you have been a specialist

Taranjeet Singh Community Leader Mar 06, 2020

nice article, thanks for sharing!

@Jessica and @Taranjeet Singh Thank you for commenting. Glad you found this interesting.  


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